10-Q

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

_________________________

FORM 10-Q

(Mark One)
x	QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934
For Quarterly Period Ended June 30, 2019
or
o	TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the Transition Period from _____ to _____

Commission File Number: 001-15204

Kingsway Financial Services Inc.

(Exact name of registrant as specified in its charter)

_________________________

Delaware (State or other jurisdiction of incorporation or organization) 98-0475673                                                                                  (I.R.S. Employer Identification No.)

150 E. Pierce Road, Itasca, IL 60143

(Address of principal executive offices and zip code)

1-416-848-1171

(Registrant's telephone number, including area code)

_________________________

Indicate by checkmark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15 (d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period the registrant was required to file such reports) and (2) has been subject to such filing requirements for the past 90 days. Yes o No x

Indicate by check mark whether the registrant has submitted electronically and posted on its corporate Web site, if any, every Interactive Data File required to be submitted and posted pursuant to Rule 405 of Regulation S-T ( 232.405 of this chapter) during the preceding 12 months (or for such shorter period the registrant was required to submit and post such files). Yes x No o

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, or a smaller reporting company. See definitions of "large accelerated filer," "accelerated filer," and "smaller reporting company" and "emerging growth company" in Rule 12b-2 of the Exchange Act.

Large accelerated filer o Accelerated filer o Non-accelerated filer o (Do not check if a smaller reporting company) Smaller Reporting Company x Emerging Growth Company o

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. o

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Act). Yes o No x

The number of shares, including restricted common shares, outstanding of the registrant's common stock as of April 10, 2020 was 22,958,519.

KINGSWAY FINANCIAL SERVICES INC.

Table Of Contents
PART I - FINANCIAL INFORMATION	3
ITEM 1. FINANCIAL STATEMENTS	3
Consolidated Balance Sheets as of June 30, 2019 (unaudited) and December 31, 2018	3
Consolidated Statements of Operations for the Three and Six Months Ended June 30, 2019 and 2018 (unaudited)	4
Consolidated Statements of Comprehensive (Loss) Income for the Three and Six Months Ended June 30, 2019 and 2018 (unaudited)	5
Consolidated Statements of Cash Flows for the Six Months Ended June 30, 2019 and 2018 (unaudited)	8
Notes to Consolidated Financial Statements (unaudited)	9
ITEM 2. MANAGEMENT'S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS	52
ITEM 3. QUANTITATIVE AND QUALITATIVE DISCLOSURES ABOUT MARKET RISK	64
ITEM 4. CONTROLS AND PROCEDURES	66
PART II - OTHER INFORMATION	68
ITEM 1. LEGAL PROCEEDINGS	68
ITEM 1A. RISK FACTORS	68
ITEM 2. UNREGISTERED SALES OF EQUITY SECURITIES AND USE OF PROCEEDS	69
ITEM 3. DEFAULTS UPON SENIOR SECURITIES	69
ITEM 4. MINE SAFETY DISCLOSURES	69
ITEM 5. OTHER INFORMATION	69
ITEM 6. EXHIBITS	70
SIGNATURES	71

2

KINGSWAY FINANCIAL SERVICES INC.

PART I. FINANCIAL INFORMATION

Item 1. Financial Statements

Consolidated Balance Sheets

(in thousands, except share data)

	June 30, 2019			December 31, 2018
	(unaudited)
Assets
Investments:
Fixed maturities, at fair value (amortized cost of $20,771 and $12,432, respectively)	$	20,787		$	12,260
Equity investments, at fair value (cost of $1,506 and $2,274, respectively)	202			856
Limited liability investments	3,891			4,790
Limited liability investments, at fair value	33,047			26,015
Investments in private companies, at adjusted cost	2,661			3,090
Real estate investments, at fair value (cost of $10,225 and $10,225, respectively)	10,662			10,662
Other investments, at cost which approximates fair value	895			2,079
Short-term investments, at cost which approximates fair value	154			152
Total investments	72,299			59,904
Cash and cash equivalents	10,899			14,619
Restricted cash	17,320			16,959
Investment in investee	1,119			951
Accrued investment income	417			420
Service fee receivable, net of allowance for doubtful accounts of $324 and $191, respectively	5,246			3,434
Other receivables, net of allowance for doubtful accounts of $201 and $184, respectively	10,554			9,523
Deferred acquisition costs, net	7,724			6,904
Property and equipment, net of accumulated depreciation of $18,310 and $15,958, respectively	101,178			103,142
Right-of-use asset	2,265			—
Goodwill	82,104			74,659
Intangible assets, net of accumulated amortization of $11,791 and $10,594, respectively	87,775			83,266
Other assets	5,394			4,459
Total Assets	$	404,294		$	378,240
Liabilities and Shareholders' Equity
Liabilities:
Accrued expenses and other liabilities	16,518			14,786
Income taxes payable	2,482			2,400
Deferred service fees	61,522			47,130
Unpaid loss and loss adjustment expenses	1,937			2,073
Bank loans	11,674			3,917
Notes payable	197,039			199,316
Subordinated debt, at fair value	50,224			50,023
Lease liability	2,410			—
Net deferred income tax liabilities	28,984			28,537
Total Liabilities	372,790			348,182
Redeemable Class A preferred stock, no par value; 1,000,000 and unlimited number authorized at June 30, 2019 and December 31, 2018, respectively; 222,876 and 222,876 issued and outstanding at June 30, 2019 and December 31, 2018, respectively; redemption amount of $7,485 and $7,278 at June 30, 2019 and December 31, 2018, respectively	6,297			5,800
Shareholders' Equity:
Common stock, no par value; 50,000,000 and unlimited number authorized at June 30, 2019 and December 31, 2018, respectively; 21,866,959 and 21,787,728 issued and outstanding at June 30, 2019 and December 31, 2018, respectively	—			—
Additional paid-in capital	353,778			353,890
Accumulated deficit	(379,872		)	(382,196		)
Accumulated other comprehensive income	39,325			40,768
Shareholders' equity attributable to common shareholders	13,231			12,462
Noncontrolling interests in consolidated subsidiaries	11,976			11,796
Total Shareholders' Equity	25,207			24,258
Total Liabilities, Class A preferred stock and Shareholders' Equity	$	404,294		$	378,240

See accompanying notes to unaudited consolidated financial statements.

3

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Operations

(in thousands, except per share data)

(Unaudited)

	Three months ended June 30,							Six months ended June 30,
	2019				2018			2019			2018
Revenues:
Service fee and commission income	$	11,772			$	8,860		$	21,587		$	18,511
Rental income	3,341				3,345			6,682			6,693
Other income	113				108			258			321
Total revenues	15,226				12,313			28,527			25,525
Operating expenses:
Claims authorized on vehicle service agreements	2,506				1,392			4,393			2,764
Loss and loss adjustment expenses	601				1,301			708			1,647
Commissions	1,103				834			2,021			1,747
Cost of services sold	1,160				1,464			2,519			3,716
General and administrative expenses	9,164				7,295			17,566			14,771
Leased real estate segment interest expense	1,520				1,546			3,047			3,098
Total operating expenses	16,054				13,832			30,254			27,743
Operating loss	(828		)		(1,519		)	(1,727		)	(2,218		)
Other revenues (expenses), net:
Net investment income	749			—	1,010			1,448			1,648
Net realized (losses) gains	(556		)	—	132			(241		)	397
(Loss) gain on change in fair value of equity investments	(63		)	—	(421		)	15			744
Gain (loss) on change in fair value of limited liability investments, at fair value	2,347				(525		)	6,612			(1,461		)
Net change in unrealized gain (loss) on private company investments	—				(155		)	19			(155		)
Other-than-temporary impairment loss	—			—	—			(75		)	—
Non-operating other income	19			—	14			173			21
Interest expense not allocated to segments	(2,339		)		(1,844		)	(4,441		)	(3,561		)
Amortization of intangible assets	(676		)		(254		)	(1,197		)	(509		)
Gain (loss) on change in fair value of debt	918				(142		)	1,494			(1,061		)
Gain on disposal of subsidiary	—				17			—			17
Equity in net income (loss) of investee	201				(385		)	168			(284		)
Total other revenues (expenses), net	600				(2,553		)	3,975			(4,204		)
(Loss) income from continuing operations before income tax expense (benefit)	(228		)		(4,072		)	2,248			(6,422		)
Income tax expense (benefit)	168				190			(545		)	444
(Loss) income from continuing operations	(396		)		(4,262		)	2,793			(6,866		)
Income from discontinued operations, net of taxes	—				594			—			980
Loss on disposal of discontinued operations, net of taxes	—				(6,628		)	—			(6,628		)
Net (loss) income	(396		)		(10,296		)	2,793			(12,514		)
Less: net income attributable to noncontrolling interests in consolidated subsidiaries	258				158			469			517
Less: dividends on preferred stock, net of tax	252				259			498			512
Net (loss) income attributable to common shareholders	$	(906	)		$	(10,713	)	$	1,826		$	(13,543	)
(Loss) earnings per share - continuing operations:
Basic:	$	(0.04	)		$	(0.22	)	$	0.08		$	(0.36	)
Diluted:	$	(0.04	)		$	(0.22	)	$	0.08		$	(0.36	)
Loss per share - discontinued operations:
Basic:	$	—			$	(0.28	)	$	—		$	(0.26	)
Diluted:	$	—			$	(0.28	)	$	—		$	(0.26	)
(Loss) earnings per share – net (loss) income attributable to common shareholders:
Basic:	$	(0.04	)		$	(0.49	)	$	0.08		$	(0.62	)
Diluted:	$	(0.04	)		$	(0.49	)	$	0.08		$	(0.62	)
Weighted-average shares outstanding (in ‘000s):
Basic:	21,867				21,708			21,854			21,708
Diluted:	21,867				21,708			21,854			21,708

See accompanying notes to unaudited consolidated financial statements.

4

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Comprehensive (Loss) Income

(in thousands)

(Unaudited)

	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Net (loss) income	$	(396	)	$	(10,296	)	$	2,793		$	(12,514	)
Other comprehensive (loss) income, net of taxes(1):
Unrealized gains (losses) on available-for-sale investments:
Unrealized gains (losses) arising during the period	121			(72		)	232			(437		)
Reclassification adjustment for amounts included in net (loss) income	(7		)	(4		)	(13		)	(11		)
Change in fair value of debt attributable to instrument-specific credit risk	(750		)	778			(1,695		)	344
Equity in other comprehensive income of limited liability investment	45			—			45			—
Other comprehensive (loss) income	(591		)	702			(1,431		)	(104		)
Comprehensive (loss) income	(987		)	(9,594		)	1,362			(12,618		)
Less: comprehensive income attributable to noncontrolling interests in consolidated subsidiaries	264			158			481			511
Comprehensive (loss) income attributable to common shareholders	$	(1,251	)	$	(9,752	)	$	881		$	(13,129	)
(1) Net of income tax expense (benefit) of $0 and $0 for the three and six months ended June 30, 2019 and June 30, 2018, respectively.

See accompanying notes to unaudited consolidated financial statements

5

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Shareholders' Equity

(in thousands, except share data)

	Three Months Ended June 30, 2019
	Common Stock			Additional Paid-in Capital			Accumulated Deficit			Accumulated Other Comprehensive Income (Loss)			Shareholders' Equity Attributable to Common Shareholders			Noncontrolling Interests in Consolidated Subsidiaries			Total Shareholders' Equity
	Shares	Amount
Balance, April 1, 2019	21,866,959	$	—	$	353,886		$	(379,218	)	$	39,922		$	14,590		$	12,013		$	26,603
Net (loss) income		—		—			(654		)	—			(654		)	258			(396		)
Preferred stock dividends	—	—		(252		)	—			—			(252		)	—			(252		)
Deconsolidation of noncontrolling interest	—	—		—			—			—			—			(301		)	(301		)
Other comprehensive (loss) income	—	—		—			—			(597		)	(597		)	6			(591		)
Stock-based compensation	—	—		144			—			—			144			—			144
Balance, June 30, 2019	21,866,959	$	—	$	353,778		$	(379,872	)	$	39,325		$	13,231		$	11,976		$	25,207

	Three Months Ended June 30, 2018
	Common Stock			Additional Paid-in Capital			Accumulated Deficit			Accumulated Other Comprehensive Income		Shareholders' Equity Attributable to Common Shareholders			Noncontrolling Interests in Consolidated Subsidiaries		Total Shareholders' Equity
	Shares	Amount
Balance, April 1, 2018	21,708,190	$	—	$	356,211		$	(354,672	)	$	35,844	$	37,383		$	10,131	$	47,514
Net (loss) income	—	—		—			(10,454		)	—		(10,454		)	158		(10,296		)
Preferred stock dividends, net of tax	—	—		(259		)	—			—		(259		)	—		(259		)
Other comprehensive income	—	—		—			—			702		702			—		702
Stock-based compensation	—	—		295			—			—		295			—		295
Balance, June 30, 2018	21,708,190	$	—	$	356,247		$	(365,126	)	$	36,546	$	27,667		$	10,289	$	37,956

6

KINGSWAY FINANCIAL SERVICES INC.

	Six Months Ended June 30, 2019
	Common Stock			Additional Paid-in Capital			Accumulated Deficit			Accumulated Other Comprehensive Income (Loss)			Shareholders' Equity Attributable to Common Shareholders			Noncontrolling Interests in Consolidated Subsidiaries			Total Shareholders' Equity
	Shares	Amount
Balance, December 31, 2018	21,787,728	$	—	$	353,890		$	(382,196	)	$	40,768		$	12,462		$	11,796		$	24,258
Vesting of restricted stock awards, net of share settlements for tax withholdings	79,231	—		—			—			—			—			—			—
Net income	—	—		—			2,324			—			2,324			469			2,793
Preferred stock dividends	—	—		(498		)	—			—			(498		)	—			(498		)
Deconsolidation of noncontrolling interest	—	—		—			—			—			—			(301		)	(301		)
Other comprehensive (loss) income	—	—		—			—			(1,443		)	(1,443		)	12			(1,431		)
Stock-based compensation	—	—		386			—			—			386			—			386
Balance, June 30, 2019	21,866,959	$	—	$	353,778		$	(379,872	)	$	39,325		$	13,231		$	11,976		$	25,207

	Six Months Ended June 30, 2018
	Common Stock			Additional Paid-in Capital			Accumulated Deficit			Accumulated Other Comprehensive Income (Loss)			Shareholders' Equity Attributable to Common Shareholders			Noncontrolling Interests in Consolidated Subsidiaries			Total Shareholders' Equity
	Shares	Amount
Balance, December 31, 2017	21,708,190	$	—	$	356,171		$	(310,953	)	$	(3,852	)	$	41,366		$	9,361		$	50,727
Cumulative effect of adoption of ASU 2014-09	—	—		—			(647		)	—			(647		)	(7		)	(654		)
Cumulative effect of adoption of ASU 2016-01	—	—		—			(40,495		)	40,495			—			—			—
Balance at January 1, 2018, as adjusted	21,708,190	—		356,171			(352,095		)	36,643			40,719			9,354			50,073
Net (loss) income	—	—		—			(13,031		)	—			(13,031		)	517			(12,514		)
Contributions from noncontrolling interest holders	—	—		—			—			—			—			425			425
Preferred stock dividends, net of tax	—	—		(512		)	—			—			(512		)	—			(512		)
Other comprehensive loss	—	—		—			—			(97		)	(97		)	(7		)	(104		)
Stock-based compensation	—	—		588			—			—			588			—			588
Balance, June 30, 2018	21,708,190	$	—	$	356,247		$	(365,126	)	$	36,546		$	27,667		$	10,289		$	37,956

See accompanying notes to unaudited consolidated financial statements

7

KINGSWAY FINANCIAL SERVICES INC.

Consolidated Statements of Cash Flows

(in thousands)

(Unaudited)

	Six months ended June 30,
	2019			2018
Cash provided by (used in):
Operating activities:
Net income (loss)	$	2,793		$	(12,514	)
Adjustments to reconcile net income (loss) to net cash used in operating activities:
Income from discontinued operations, net of taxes	—			(980		)
Loss on disposal of discontinued operations, net of taxes	—			6,628
Equity in net (income) loss of investee	(168		)	284
Equity in net income of limited liability investments	(14		)	(181		)
Depreciation and amortization expense	3,373			2,678
Stock-based compensation expense, net of forfeitures	386			588
Net realized losses (gains)	241			(397		)
Gain on change in fair value of equity investments	(15		)	(744		)
(Gain) loss on change in fair value of limited liability investments, at fair value	(6,612		)	1,461
Net change in unrealized (gain) loss on private company investments	(19		)	155
(Gain) loss on change in fair value of debt	(1,494		)	1,061
Deferred income taxes, adjusted for Geminus liabilities assumed	(816		)	56
Other-than-temporary impairment loss	75			—
Amortization of fixed maturities premiums and discounts	(7		)	32
Amortization of note payable premium	(461		)	(473		)
Gain on disposal of subsidiary	—			(17		)
Changes in operating assets and liabilities:
Service fee receivable, net, adjusted for Geminus assets acquired	(1,299		)	(787		)
Other receivables, net, adjusted for Geminus assets acquired	(1,019		)	(1,617		)
Deferred acquisition costs, net	(820		)	(337		)
Unpaid loss and loss adjustment expenses	(136		)	1,265
Deferred service fees, adjusted for Geminus liabilities assumed	3,828			3,255
Other, net, adjusted for Geminus assets acquired and liabilities assumed	(270		)	(3,566		)
Cash used in operating activities - continuing operations	(2,454		)	(4,150		)
Cash used in operating activities - discontinued operations	—			(1,909		)
Net cash used in operating activities	(2,454		)	(6,059		)
Investing activities:
Proceeds from sales and maturities of fixed maturities	5,887			4,965
Proceeds from sales of equity investments	675			3,704
Purchases of fixed maturities	(9,794		)	(1,885		)
Purchases of equity investments	—			(806		)
Net proceeds from limited liability investments	282			2,199
Net purchases of limited liability investments, at fair value	(336		)	(666		)
Net proceeds from investments in private companies	249			95
Net proceeds from other investments	1,239			405
Net proceeds from short-term investments	30			—
Proceeds from disposal of subsidiary	—			565
Net proceeds from sale of discontinued operations	—			1,129
Acquisition of business, net of cash acquired	(4,792		)	—
Net disposals of property and equipment, adjusted for Geminus assets acquired	(134		)	593
Cash (used in) provided by investing activities - continuing operations	(6,694		)	10,298
Cash used in investing activities - discontinued operations	—			(3,086		)
Net cash (used in) provided by investing activities	(6,694		)	7,212
Financing activities:
Taxes paid related to net share settlements of restricted stock awards	(89		)	—
Principal proceeds from bank loan, net of debt issuance costs of $981	9,019			—
Principal payments on bank loans	(1,325		)	(500		)
Principal payments on notes payable	(1,816		)	(1,632		)
Cash provided by (used in) financing activities - continuing operations	5,789			(2,132		)
Cash used in financing activities - discontinued operations	—			—
Net cash provided by (used in) financing activities	5,789			(2,132		)
Net (decrease) increase in cash and cash equivalents and restricted cash from continuing operations	(3,359		)	4,016
Cash and cash equivalents and restricted cash at beginning of period	31,578			43,874
Less: cash and cash equivalents and restricted cash of discontinued operations at beginning of period	—			23,512
Cash and cash equivalents and restricted cash of continuing operations at beginning of period	31,578			20,362
Cash and cash equivalents and restricted cash of continuing operations at end of period	$	28,219		$	24,378

See accompanying notes to unaudited consolidated financial statements.

8

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

NOTE 1 BUSINESS

Kingsway Financial Services Inc. (the "Company" or "Kingsway") was incorporated under the Business Corporations Act (Ontario) on September 19, 1989. Effective December 31, 2018, the Company changed its jurisdiction of incorporation from the province of Ontario, Canada, to the State of Delaware. Kingsway is a holding company with operating subsidiaries located in the United States. The Company owns or controls subsidiaries primarily in the extended warranty, asset management and real estate industries.

NOTE 2 BASIS OF PRESENTATION

The accompanying unaudited consolidated interim financial statements have been prepared in accordance with accounting principles generally accepted in the United States of America ("U.S. GAAP") for interim financial information and with the instructions to Form 10-Q and Article 10 of Regulation S-X. Accordingly, they do not include all of the information and notes required by U.S. GAAP for complete financial statements of the Company. In the opinion of management, all adjustments necessary for a fair presentation have been included and are of a normal recurring nature. Interim results are not necessarily indicative of the results that may be expected for the year.

Certain prior year amounts have been reclassified to conform to current year presentation. Such reclassifications had no impact on previously reported net loss or total shareholders' equity.

The accompanying unaudited consolidated interim financial statements and footnotes should be read in conjunction with the audited consolidated financial statements and footnotes included within our Annual Report on Form 10-K ("2018 Annual Report") for the year ended December 31, 2018.

The unaudited consolidated interim financial statements include the accounts of the Company and its subsidiaries, as well as certain variable interest entities as further described in Note 7, "Variable Interest Entities," to the consolidated financial statements in the 2018 Annual Report. All material intercompany transactions and balances have been eliminated in consolidation.

The preparation of consolidated financial statements in conformity with U.S. GAAP requires management to make estimates and assumptions that affect the reported amounts and classifications of assets and liabilities, revenues and expenses, and the related disclosures of contingent assets and liabilities in the consolidated financial statements and accompanying notes. Actual results could differ from these estimates. Estimates and their underlying assumptions are reviewed on an ongoing basis. Changes in estimates are recorded in the accounting period in which they are determined. The critical accounting estimates and assumptions in the accompanying unaudited consolidated interim financial statements include the provision for unpaid loss and loss adjustment expenses; valuation of fixed maturities and equity investments; impairment assessment of investments; valuation of limited liability investments, at fair value; valuation of real estate investments; valuation of deferred income taxes; valuation of mandatorily redeemable preferred stock; valuation and impairment assessment of intangible assets; goodwill recoverability; deferred acquisition costs; fair value assumptions for subordinated debt obligations; and revenue recognition.

The fair values of the Company's investments in fixed maturities and equity investments, limited liability investments, at fair value, real estate investments, subordinated debt and warrant liability are estimated using a fair value hierarchy to categorize the inputs it uses in valuation techniques. The fair value of the Company's investment in investee is based on quoted market prices. Fair values for other investments approximate their unpaid principal balance. The carrying amounts reported in the consolidated balance sheets approximate fair values for cash and cash equivalents, restricted cash, short-term investments and certain other assets and other liabilities because of their short-term nature.

The Company's financial results contained herein are reported in U.S. dollars unless otherwise indicated.

NOTE 3 SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

Except as set forth below and as discussed in Note 4, "Recently Issued Accounting Standards," related to the Company's adoption of ASU 2016-02 effective January 1, 2019, there have been no material changes to our significant accounting policies as reported in our 2018 Annual Report.

Holding Company Liquidity

The Company's Extended Warranty subsidiaries fund their obligations primarily through service fee and commission income. The Company's Leased Real Estate subsidiary funds its obligations through rental income. The Company's insurance subsidiaries fund their obligations primarily through investment income and maturities in the investments portfolios.

9

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

The liquidity of the holding company is managed separately from its subsidiaries. The obligations of the holding company primarily consist of holding company operating expenses; transaction-related expenses; investments; and any other extraordinary demands on the holding company.

Actions available to the holding company to increase liquidity in order to meet its obligations include the sale of passive investments; sale of subsidiaries; issuance of debt or equity securities; distributions from the Company’s Extended Warranty subsidiaries, subject to certain restrictions; and giving notice to its Trust Preferred trustees of its intention to exercise its voluntary right to defer interest payments for up to 20 quarters on the six subsidiary trusts of the Company’s subordinated debt, which right the Company exercised during the third quarter of 2018.

Dividends from the Leased Real Estate segment are not generally considered a source of liquidity for the holding company, except upon the occurrence of certain events that would trigger payment of service fees. There can be no assurance as to the timing of the occurrence, or the resulting outcome, from one of these events.

The holding company’s liquidity, defined as the amount of cash in the bank accounts of Kingsway Financial Services Inc. and Kingsway America Inc., was $1.8 million and $1.9 million at June 30, 2019 and December 31, 2018, respectively, which excludes future actions available to the holding company that could be taken to increase liquidity and reflects approximately four months of operating cash. These amounts are reflected in the cash and cash equivalents of $10.9 million and $14.6 million reported at June 30, 2019 and December 31, 2018, respectively, on the Company’s consolidated balance sheets. The cash and cash equivalents and restricted cash other than the holding company’s liquidity represent restricted and unrestricted cash held by Kingsway Amigo Insurance Company ("Amigo"), Kingsway Reinsurance Corporation and the Company’s Extended Warranty and Leased Real Estate segments.

As of March 31, 2020, there are 182,876 shares of the Company’s Class A Preferred Stock (the "Preferred Shares"), issued and outstanding. Any outstanding Preferred Shares would be required to be redeemed by the Company on April 1, 2021 ("Redemption Date") at a redemption value of $6.7 million (assuming all current outstanding Preferred Shares would be redeemed), if the Company has sufficient legally available funds to do so. Additionally, the Company has exercised its right to defer payment of interest on its outstanding subordinated debt ("trust preferred securities") and, because of the deferral which totaled $10.5 million at March 31, 2020, the Company is prohibited from redeeming any shares of its capital stock while payment of interest on the trust preferred securities is being deferred. If, as of April 1, 2021, the Company was required to pay both the deferred interest on the trust preferred securities and redeem all the Preferred Shares currently outstanding, then the Company currently projects that it would not have sufficient legally available funds to do so. However, the Company would be prohibited from doing so under Delaware law and, as such, (a) the interest estimated to be $14.9 million on March 31, 2021 on the trust preferred securities would remain on deferral as permitted under the indentures and (b) in accordance with Delaware law the Preferred Shares would not be redeemed on the Redemption Date (with a redemption value of $6.7 million) and would instead remain outstanding and continue to accrue dividends until such time as the Company has sufficient legally available funds to redeem the Preferred Shares and is not otherwise prohibited from doing so. In such a situation, the Company would continue to operate in the ordinary course.

The Company notes there are several variables to consider in such a situation, and management is currently exploring the following opportunities: negotiating with the holders of the Preferred Shares with respect to the Redemption Date and/or other key provisions, raising additional funds through capital market transactions, as well as the Company’s continued strategy of working to monetize its non-core investments while attempting to maximize the tradeoff between liquidity and value received. The Company also notes that the conversion of any Preferred Shares that might occur prior to April 1, 2021 would impact its analysis as of April 1, 2021.

Based on the Company’s current business plan and revenue prospects, existing cash, cash equivalents, investment balances and anticipated cash flows from operations are expected to be sufficient to meet the Company’s working capital and operating expenditure requirements, excluding the cash that may be required to redeem the Preferred Shares and deferred interest on its trust preferred securities, for the next twelve months. However, the Company’s assessment could also be affected by various risks and uncertainties, including, but not limited to, the effects of the COVID-19 pandemic.

10

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

NOTE 4 RECENTLY ISSUED ACCOUNTING STANDARDS

(a)    Adoption of New Accounting Standards:

Effective January 1, 2018, the Company adopted Accounting Standards Update ("ASU") 2014-09, Revenue from Contracts with Customers ("ASU 2014-09"), and the related amendments, utilizing the modified retrospective approach, which created a new comprehensive revenue recognition standard that serves as the single source of revenue guidance for all contracts with customers to transfer goods or services or contracts for the transfer of nonfinancial assets, unless those contracts are within the scope of other standards. The core principle of ASU 2014-09 is that an entity recognizes revenue to depict the transfer of promised goods or services to customers in an amount that reflects the consideration to which the entity expects to be entitled in exchange for those goods or services. Insurance contracts, lease contracts and investments are not within the scope of ASU 2014-09. ASU 2014-09 is applicable to the Company's service fee and commission income. Service fee and commission income represents vehicle service agreement fees, GAP commissions, maintenance support service fees, warranty product commissions, homebuilder warranty service fees and homebuilder warranty commissions based on terms of various agreements with credit unions, consumers, businesses and homebuilders. With the exception of GAP commissions and homebuilder warranty service fees, the adoption of ASU 2014-09 did not change the way the Company recognized revenue for the year ended December 31, 2018. The new guidance affects IWS' GAP commissions and PWSC's homebuilder warranty service fees, which will be recognized more slowly as compared to the historic revenue recognition pattern prior to the Company’s adoption of ASU 2014-09. As a result of the adoption of ASU 2014-09, the Company also recorded a cumulative effect adjustment to increase accumulated deficit by $0.6 million and increase deferred service fees by $0.6 million. Prior periods have not been restated to conform to the current presentation. Refer to Note 15, "Revenue from Contracts with Customers," for further details.

Effective January 1, 2018, the Company adopted ASU 2016-01, Financial Instruments-Overall (Subtopic 825-10): Recognition and Measurement of Financial Assets and Financial Liabilities ("ASU 2016-01").The amendments in ASU 2016-01 address certain aspects of recognition, measurement, presentation, and disclosure of financial instruments. Most significantly, ASU 2016-01 requires (1) equity investments (except those accounted for under the equity method of accounting or those that result in consolidation of an investee) to be measured at fair value with changes in fair value recognized in net income (loss); however, an entity may choose to measure equity investments that do not have readily determinable fair values at cost, adjusted for observable price changes and impairments; and (2) an entity to present separately in other comprehensive income (loss) the portion of the total change in the fair value of a liability resulting from a change in the instrument-specific credit risk when the entity has elected to measure the liability at fair value in accordance with the fair value option for financial instruments. The Companyhas electedto measure its investments in private companies at cost, adjusted for observable price changes and impairments. Previously, the Company recorded its equity investments at fair value with net unrealized gains or losses reported in accumulated other comprehensive income (loss) and its subordinated debt at fair value with the total change in fair value reported in net income (loss). As a result of the adoption of ASU 2016-01, at January 1, 2018 cumulative net unrealized losses on equity investments of $0.0 million were reclassified from accumulated other comprehensive income (loss) into accumulated deficit and a cumulative $40.5 million change in fair value of subordinated debt attributable to instrument-specific credit risk was reclassified from accumulated deficit to accumulated other comprehensive income (loss). Prior periods have not been restated to conform to the current presentation.

Effective January 1, 2018, the Company adopted ASU 2016-15, Classification of Certain Cash Receipts and Cash Payments ("ASU 2016-15"). The objective of ASU 2016-15 is to reduce diversity in the classification of cash receipts and payments for specific cash flow issues, including debt prepayment or debt extinguishment costs, contingent consideration payments made after a business combination and proceeds from the settlement of insurance claims. The adoption of the standard did not affect the Company's consolidated statements of cash flows.

Effective January 1, 2018, the Company adopted ASU 2016-18, Statement of Cash Flows (Topic 230) Restricted Cash ("ASU 2016-18"). The objective of ASU 2016-18 is to explain the change during the period in the total cash, cash equivalents and amounts generally described as restricted cash or restricted cash equivalents.  Amounts generally described as restricted cash and cash equivalents should be included with the cash and cash equivalents when reconciling the beginning of period and end of period total amounts shown on the statement of cash flows.  As a result of the adoption of the standard, the change in restricted cash is included in the consolidated statements of cash flows.

Effective July 1, 2018, the Company adopted ASU 2018-07, Compensation-Stock Compensation (Topic 718): Improvements to Nonemployee Share-Based Payment Accounting ("ASU 2018-07"). ASU 2018-07 was issued to simplify the accounting for share-based transactions by expanding the scope of Topic 718 from only being applicable to share-based payments to employees to also include share-based payment transactions for acquiring goods and services from nonemployees. During the third quarter of 2018,

11

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

the Company granted restricted common stock awards to a nonemployee. Refer to Note 18, "Stock-Based Compensation," for further details.

Effective January 1, 2019, the Company adopted ASU 2016-02, Leases ("ASU 2016-02").ASU 2016-02 was issued to improve the financial reporting of leasing transactions. Under current guidance for lessees, leases are only included on the balance sheet if certain criteria, classifying the agreement as a capital lease, are met. This update requires the recognition of a right-of-use asset and a corresponding lease liability, discounted to the present value, for all leases that extend beyond 12 months. For operating leases, the asset and liability will be amortized over the lease term on a straight-line basis, with all cash flows included within operating activities in the statement of cash flows. The accounting treatment for lessors will remain relatively unchanged. The Company adopted ASU 2016-02 using the modified retrospective transition method and did not restate comparative periods. The adoption had a significant effect on the Company's consolidated balance sheet. Refer to Note 14, "Leases," for further information regarding the adoption of ASU 2016-02.

(b)    Accounting Standards Not Yet Adopted:

In June 2016, the FASB issued ASU 2016-13, Financial Instruments-Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments ("ASU 2016-13"). ASU 2016-13 replaces the current incurred loss model used to measure impairment losses with an expected loss model for trade, reinsurance, and other receivables as well as financial instruments measured at amortized cost. ASU 2016-13 will require a financial asset measured at amortized cost, including reinsurance balances recoverable, to be presented at the net amount expected to be collected by means of an allowance for credit losses that runs through net loss. Credit losses relating to available-for-sale debt securities will also be recorded through an allowance for credit losses. However, the amendments would limit the amount of the allowance to the amount by which fair value is below amortized cost. The measurement of credit losses on available-for-sale investments is similar under current GAAP, but the update requires the use of the allowance account through which amounts can be reversed, rather than through irreversible write-downs. On November 15, 2019, the FASB issued ASU 2019-10, which (1) provides a framework to stagger effective dates for future major accounting standards and (2) amends the effective dates for certain major new accounting standards to give implementation relief to certain types of entities. Specifically, per ASU 2019-10 the Company would adopt ASU 2016-13 beginning January 1, 2023, as the Company is considered to be a smaller reporting company. The Company is currently evaluating ASU 2016-13 to determine the potential impact that adopting this standard will have on its consolidated financial statements.

In January 2017, the FASB issued ASU 2017-04, Intangibles - Goodwill and Other (Topic 350): Simplifying the Test for Goodwill Impairment ("ASU 2017-04"). ASU 2017-04 was issued to simplify the subsequent measurement of goodwill. This update changes the impairment test by requiring an entity to compare the fair value of a reporting unit with its carrying amount as opposed to comparing the carrying amount of goodwill with its implied fair value. ASU 2017-04 is effective for annual and interim reporting periods beginning after December 15, 2019. Early adoption is permitted. The Company does not believe the adoption of ASU 2017-04 will have a material effect on its consolidated financial statements.

In October 2018, the FASB issued ASU 2018-17, Consolidation (Topic 810): Targeted Improvements to Related Party Guidance for Variable Interest Entities ("ASU 2018-17"). Among other things, ASU 2018-17 changes how all entities that apply the variable interest entity ("VIE") guidance evaluate decision making fees. Under ASU 2018-17, when an entity determines whether a decision-making fee is a variable interest, it considers indirect interests held through related parties under common control on a proportionate basis rather than in their entirety. The new approach is consistent with how indirect interests held by related parties under common control are evaluated when determining whether a reporting entity is the primary beneficiary of a VIE. ASU 2018-17 is effective for annual and interim reporting periods beginning after December 15, 2019. Early adoption is permitted. The Company is currently evaluating ASU 2018-17 to determine the potential impact that adopting this standard will have on its consolidated financial statements.

NOTE 5 ACQUISITION AND DISCONTINUED OPERATIONS

(a)     Acquisition

Geminus Holdings Company, Inc.:

On March 1, 2019, the Company acquired 100% of the outstanding shares of Geminus Holding Company, Inc. ("Geminus") for total consideration of $8.4 million, comprised of $7.7 million of cash and an installment payable to the seller of $0.7 million due February 15, 2020. The payable to seller was paid in full by February 15, 2020. At June 30, 2019, the balance of the payable to seller was $0.2 million. As further discussed in Note 20, "Segmented Information," Geminus is included in the Extended Warranty segment. Geminus is a specialty, full-service provider of vehicle service agreements and other finance and insurance products to used car buyers around the country. Geminus, headquartered in Wilkes-Barre, Pennsylvania, has been creating, marketing and

12

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

administering these products on high-mileage used cars through its subsidiaries, The Penn Warranty Corporation ("Penn") and Prime Auto Care, Inc. ("Prime"), since 1988. Penn and Prime distribute these products via independent used car dealerships and franchised car dealerships, respectively. This acquisition allows the Company to grow its portfolio of warranty companies and further expand into the vehicle service agreement business.

This acquisition was accounted for as a business combination using the acquisition method of accounting. The purchase price was allocated to the assets acquired and liabilities assumed based upon their estimated fair values at the date of acquisition. Goodwill of $7.4 million was recognized, and $5.7 million of separately identifiable intangible assets were recognized resulting from the valuations of acquired customer relationships and trade names. Refer to Note 9, "Intangible Assets," for further disclosure of the intangible assets related to this acquisition. The goodwill represents the premium paid over the fair value of the net tangible and intangible assets acquired, which the Company paid to grow its portfolio of warranty companies and acquire an assembled workforce. The goodwill is not deductible for tax purposes. During the three months ended June 30, 2019 and June 30, 2018, the Company incurred acquisition-related expenses of zero and $0.0 million, respectively, ($0.0 million year to date compared to $0.0 million prior year to date), which are included in general and administrative expensesin the consolidated statements of operations.

The following table summarizes the estimated fair values of the assets acquired and liabilities assumed at the date of acquisition:

(in thousands)
	March 1, 2019
Investments	$	4,405
Cash and cash equivalents	755
Restricted cash	2,650
Accrued investment income	32
Service fee receivable	513
Other receivables	12
Property and equipment, net	79
Goodwill	7,445
Intangible assets not subject to amortization - trade names	1,974
Intangible asset subject to amortization - customer relationships	3,732
Other assets	620
Total assets	$	22,217
Accrued expenses and other liabilities	$	2,018
Income taxes payable	1
Deferred service fees	10,564
Net deferred income tax liabilities	1,263
Total liabilities	$	13,846
Purchase price	$	8,371

The consolidated statements of operations include the earnings of Geminus from the date of acquisition. From the date of acquisition through June 30, 2019, Geminus earned revenue of $3.7 million and net income of $0.6 million. The following unaudited pro forma summary presents the Company's consolidated financial statements for the three and six months ended June 30, 2019 and June 30, 2018 as if Geminus had been acquired on January 1, 2018. The pro forma summary is presented for illustrative purposes only and does not purport to represent the results of our operations that would have actually occurred had the acquisition occurred on January 1, 2018 or project our results of operations as of any future date or for any future period, as applicable.

13

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

(in thousands, except per share data)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019		2018
Revenues	$	15,226		$	15,218		$	30,491	$	30,982
(Loss) income from continuing operations attributable to common shareholders	$	(906	)	$	(5,357	)	$	676	$	(8,874	)
Basic (loss) earnings per share - continuing operations	$	(0.04	)	$	(0.25	)	$	0.03	$	(0.41	)
Diluted (loss) earnings per share - continuing operations	$	(0.04	)	$	(0.25	)	$	0.03	$	(0.41	)

(b)     Discontinued Operations

Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company:

On July 16, 2018, the Company announced it had entered into a definitive agreement to sell its non-standard automobile insurance companies Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company (collectively "Mendota"). On October 18, 2018, the Company completed the previously announced sale of Mendota. As a result of this announcement, Mendota, which was previously disclosed as part of the Insurance Underwriting segment, has been classified as a discontinued operation, and the results of their operations are reported separately for all periods presented. The Company recognized a loss on disposal of Mendota of $8.0 million in the second quarter of 2018 as a result of adjusting the net carrying value of Mendota to be equal to the estimated purchase price. For the year ended December 31, 2018, the Company recognized a loss on disposal of Mendota of $8.5 million.

The final aggregate purchase price of $28.6 million was redeployed primarily to acquire equity investments, limited liability investments, limited liability investment, at fair value and other investments, which were owned by Mendota at the time of the closing, and to fund $5.0 million into an escrow account to be used to satisfy potential indemnity obligations under the definitive stock purchase agreement. As part of the transaction, the Company will indemnify the buyer for any loss and loss adjustment expenses with respect to open claims and certain specified claims in excess of Mendota's carried unpaid loss and loss adjustment expenses at June 30, 2018. The maximum obligation to the Company with respect to the open claims is $2.5 million. There is no maximum obligation to the Company with respect to the specified claims. During the first quarter of 2019, Mendota settled one of the two specified claims for $0.5 million, resulting in no loss to the Company. During the fourth quarter of 2019, Mendota notified the Company that Mendota had entered into an agreement to settle the remaining specified claim. The Company estimates it will incur a net loss of approximately $1.6 million related to the settlement of the remaining specified claim, which the Company will report in its consolidated statement of operations for the year ended December 31, 2019. The $1.6 million settlement was funded from the $5.0 million escrow account, and the $3.4 million remaining in the escrow account was released to the Company during the first quarter of 2020 consistent with the terms of the escrow agreement.

Assigned Risk Solutions Ltd:

On April 1, 2015, the Company closed on the sale of its subsidiary, Assigned Risk Solutions Ltd. ("ARS").  The terms of the sale provided for receipt by the Company of future earnout payments equal to 1.25% of ARS' written premium and fee income during the earnout periods. The earnout payments were payable in three annual installments beginning in April 2016 through April 2018. During the second quarter of 2018, the Company received cash consideration, before expenses, of $1.7 million for the third annual installment earnout payment. Net of expenses, the Company recorded an additional gain on disposal of ARS of $1.3 million for the three and six months ended June 30, 2018, respectively. As a result of the sale, ARS, previously disclosed as part of the Extended Warranty segment, has been classified as a discontinued operation.

Summary financial information for Mendota and ARS included in income from discontinued operations, net of taxes in the statements of operations for the three and six months ended June 30, 2018 is presented below:

14

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

(in thousands)	Three months ended June 30,			Six months ended June 30,
	2018			2018
Income (loss) from discontinued operations, net of taxes:
Revenues:
Net premiums earned	$	22,956		$	51,592
Total revenues	22,956			51,592
Other revenues (expenses), net:
Loss and loss adjustment expenses	(18,927		)	(41,728		)
Commissions and premium taxes	(2,225		)	(6,388		)
General and administrative expenses	(3,825		)	(7,778		)
Net investment income	208			434
Net realized losses	(134		)	(134		)
Gain on change in fair value of equity investments	96			106
Other income	2,445			4,876
Total other revenue (expenses), net	(22,362		)	(50,612		)
Income from discontinued operations before income tax benefit	594			980
Income tax benefit	—			—
Income from discontinued operations, net of taxes	594			980
Loss on disposal of discontinued operations before income tax expense	(6,628		)	(6,628		)
Income tax expense	—			—
Loss on disposal of discontinued operations, net of taxes	(6,628		)	(6,628		)
Total loss from discontinued operations, net of taxes	$	(6,034	)	$	(5,648	)

NOTE 6 INVESTMENTS

The amortized cost, gross unrealized gains and losses, and estimated fair value of the Company's available-for-sale investments at June 30, 2019 and December 31, 2018 are summarized in the tables shown below:

(in thousands)	June 30, 2019
	Amortized Cost		Gross Unrealized Gains		Gross Unrealized Losses		Estimated  Fair Value
Fixed maturities:
U.S. government, government agencies and authorities	$	15,007	$	52	$	13	$	15,046
States, municipalities and political subdivisions	604		1		4		601
Mortgage-backed	2,474		2		22		2,454
Corporate	2,686		9		9		2,686
Total fixed maturities	$	20,771	$	64	$	48	$	20,787

15

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

(in thousands)	December 31, 2018
	Amortized Cost		Gross Unrealized Gains		Gross Unrealized Losses		Estimated  Fair Value
Fixed maturities:
U.S. government, government agencies and authorities	$	5,594	$	1	$	48	$	5,547
States, municipalities and political subdivisions	621		—		14		607
Mortgage-backed	3,256		—		70		3,186
Corporate	2,961		—		41		2,920
Total fixed maturities	12,432		1		173		12,260

The table below summarizes the Company's fixed maturities at June 30, 2019 by contractual maturity periods. Actual results may differ as issuers may have the right to call or prepay obligations, with or without penalties, prior to the contractual maturity of these obligations.

(in thousands)	June 30, 2019
	Amortized Cost		Estimated Fair Value
Due in one year or less	$	11,652	$	11,672
Due after one year through five years	7,641		7,650
Due after five years through ten years	194		192
Due after ten years	1,284		1,273
Total	$	20,771	$	20,787

The following tables highlight the aggregate unrealized loss position, by security type, of available-for-sale investments in unrealized loss positions as of June 30, 2019 and December 31, 2018. The tables segregate the holdings based on the period of time the investments have been continuously held in unrealized loss positions.

(in thousands)									June 30, 2019
	Less than 12 Months				Greater than 12 Months				Total
	Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss
Fixed maturities:
U.S. government, government agencies and authorities	$	2,497	$	2	$	1,950	$	11	$	4,447	$	13
States, municipalities and political subdivisions	75		—		453		4		528		4
Mortgage-backed	150		—		1,698		22		1,848		22
Corporate	121		—		1,123		9		1,244		9
Total fixed maturities	$	2,843	$	2	$	5,224	$	46	$	8,067	$	48

16

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

(in thousands)									December 31, 2018
	Less than 12 Months				Greater than 12 Months				Total
	Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss
Fixed maturities:
U.S. government, government agencies and authorities	$	1,497	$	1	$	2,609	$	47	$	4,106	$	48
States, municipalities and political subdivisions	—		—		606		14		606		14
Mortgage-backed	800		1		2,134		69		2,934		70
Corporate	595		1		2,151		40		2,746		41
Total fixed maturities	$	2,892	$	3	$	7,500	$	170	$	10,392	$	173

There are approximately 44 and 64 individual available-for-sale investments that were in unrealized loss positions as of June 30, 2019 and December 31, 2018, respectively. 

The establishment of an other-than-temporary impairment on an investment requires a number of judgments and estimates. The Company performs a quarterly analysis of the individual investments to determine if declines in market value are other-than-temporary. The analysis includes some or all of the following procedures as deemed appropriate by the Company:

• identifying all unrealized loss positions that have existed for at least six months;

• identifying other circumstances management believes may affect the recoverability of the unrealized loss positions;

• obtaining a valuation analysis from third-party investment managers regarding the intrinsic value of these investments based on their knowledge and experience together with market-based valuation techniques;

• reviewing the trading range of certain investments over the preceding calendar period;

• assessing if declines in market value are other-than-temporary for debt instruments based on the investment grade credit ratings from third-party rating agencies;

• assessing if declines in market value are other-than-temporary for any debt instrument with a non-investment grade credit rating based on the continuity of its debt service record;

• determining the necessary provision for declines in market value that are considered other-than-temporary based on the analyses performed; and

• assessing the Company's ability and intent to hold these investments at least until any potential investment impairment is recovered.

The risks and uncertainties inherent in the assessment methodology used to determine declines in market value that are other-than-temporary include, but may not be limited to, the following:

• the opinions of professional investment managers could be incorrect;

• the past trading patterns of individual investments may not reflect future valuation trends;

• the credit ratings assigned by independent credit rating agencies may be incorrect due to unforeseen or unknown facts related to a company's financial situation; and

• the debt service pattern of non-investment grade instruments may not reflect future debt service capabilities and may not reflect a company's unknown underlying financial problems.

As a result of the analysis performed by the Company to determine declines in market value that are other-than-temporary, the Company recorded no write-downs for other-than-temporary impairment related to limited liability investments for the three months ended June 30, 2019 and June 30, 2018, respectively ($0.1 million year to date compared to zero prior year to date). There were no write-downs recorded for other-than-temporary impairments related to available-for sale investments for the three and six months ended June 30, 2019 and June 30, 2018, respectively.

The Company has reviewed currently available information regarding investments with estimated fair values less than their carrying amounts and believes these unrealized losses are not other-than-temporary and are primarily due to temporary market and sector-related factors rather than to issuer-specific factors. The Company does not intend to sell those investments, and it is not likely it will be required to sell those investments before recovery of its amortized cost.

17

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

The Company does not have any exposure to subprime mortgage-backed investments.

Limited liability investments include investments in limited liability companies and limited partnerships. The Company's interests in these investments are not deemed minor and, therefore, are accounted for under the equity method of accounting. The most recently available financial statements are used in applying the equity method. The difference between the end of the reporting period of the limited liability entities and that of the Company is no more than three months. As of June 30, 2019 and December 31, 2018, the carrying value of limited liability investments totaled $3.9 million and $4.8 million, respectively. Income or loss from limited liability investments is recognized based on the Company's share of the earnings of the limited liability entities and is included in net investment income in the consolidated statements of operations. At June 30, 2019, the Company has no unfunded commitments related to limited liability investments.

Limited liability investments, at fair value represents the Company's investment in 26.7% of the outstanding units of 1347 Investors LLC ("1347 Investors") as well as the underlying investments of the Company’s consolidated entities Net Lease Investment Grade Portfolio LLC ("Net Lease") and Argo Holdings Fund I, LLC ("Argo Holdings").

The fair value of the Company's investment in 1347 Investors is calculated based on a model that distributes the net equity of 1347 Investors to all classes of membership interests. The model uses quoted market prices and significant market observable inputs. The most significant input to the model is the observed stock price of Limbach Holdings, Inc. ("Limbach") common stock.

During the fourth quarter of 2019, the Company’s investment in 1347 Investors was dissolved, which resulted in the Company holding shares of Limbach common stock directly.  During the third and fourth quarters of 2019 and through the first quarter of 2020, the Limbach common stock price has declined, which has resulted in the Company recording loss on change in fair value related to its investment in 1347 Investors and Limbach of $2.7 million, $0.7 million and $0.6 million, respectively.

As of June 30, 2019 and December 31, 2018, the carrying value of the Company's limited liability investments, at fair value was $33.0 million and $26.0 million, respectively. The Company recorded impairments related to limited liability investments, at fair value of $0.0 million and zero for the three months ended June 30, 2019 and June 30, 2018, respectively, ($0.0 million and $0.0 million for the six months ended June 30, 2019 and June 30, 2018, respectively), which are included in (loss) gain on change in fair value of limited liability investments, at fair value in the consolidated statements of operations. At June 30, 2019, the Company has unfunded commitments totaling $0.6 million to fund limited liability investments, at fair value, all of which related to the Company’s commitment to Argo Holdings. On December 4, 2019, Argo Management informed members of Argo Holdings that no more requests for funds are planned.

Investments in private companies consist of convertible preferred stocks and notes in privately owned companies and investments in limited liability companies in which the Company’s interests are deemed minor. The Company's investments in private companies do not have readily determinable fair values. The Company has elected to record investments in private companies at cost, adjusted for observable price changes and impairments. As of June 30, 2019 and December 31, 2018, the carrying value of the Company's investments in private companies totaled $2.7 million and $3.1 million, respectively. For the three months ended June 30, 2019 and June 30, 2018, the Company recorded adjustments of zero and $0.2 million, respectively, ($0.0 million and $0.2 million for the six months ended June 30, 2019 and June 30, 2018, respectively), to adjust the fair value of certain investments in private companies for observable price changes, which are included in net change in unrealized gain (loss) on private company investments in the consolidated statements of operations.

The Company performs a quarterly impairment analysis of its investments in private companies. The analysis includes some or all of the following procedures as deemed appropriate by the Company:

• the opinions of external investment and portfolio managers;

• the financial condition and prospects of the investee;

• recent operating trends and forecasted performance of the investee;

• current market conditions in the geographic area or industry in which the investee operates;

• changes in credit ratings; and

• changes in the regulatory environment.

As a result of the analysis performed, the Company recorded no write-downs for other-than-temporary impairments related to investments in private companies for the three and six months ended June 30, 2019 and June 30, 2018.

Real estate investments are reported at fair value. As of June 30, 2019 and December 31, 2018, the carrying value of the Company's real estate investments totaled $10.7 million and $10.7 million, respectively.

18

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

Other investments include collateral loans and are reported at their unpaid principal balance. As of June 30, 2019 and December 31, 2018, the carrying value of other investments totaled $0.9 million and $2.1 million, respectively.

The Company had previously entered into two separate performance share grant agreements with 1347 Property Insurance Holdings, Inc. ("PIH"), whereby the Company will be entitled to receive up to an aggregate of 475,000 shares of PIH common stock upon achievement of certain milestones for PIH’s stock price. Pursuant to the performance share grant agreements, if at any time the last sales price of PIH’s common stock equals or exceeds: (i) $10.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 100,000 shares of PIH common stock; (ii) $12.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 100,000 shares of common stock earned pursuant to clause (i) herein); (iii) $15.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 225,000 shares of common stock earned pursuant to clauses (i) and (ii) herein); and (iv) $18.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 350,000 shares of common stock earned pursuant to clauses (i), (ii) and (iii) herein). To the extent shares of PIH common stock are granted to the Company under either of the performance share grant agreements, they will be recorded at the time the shares are granted and will have a valuation equal to the last sales price of PIH common stock on the day prior to such grant.

On January 2, 2018, the Company entered into an agreement with PIH to cancel the $10.00 per share performance shares grant agreement in exchange for cash consideration of $0.3 million. For the six months ended June 30, 2018, the Company recorded a gain, included in (loss) gain on change in fair value of equity investments in the consolidated statements of operations, of $0.3 million related to this transaction. No shares were received by the Company under either of the performance share grant agreements as of June 30, 2019.

Net investment income for the three and six months ended June 30, 2019 and June 30, 2018 is comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Investment income:
Interest from fixed maturities	$	122		$	57		$	195		$	90
Dividends	70			82			128			156
Income from limited liability investments	32			189			14			181
Income from limited liability investments, at fair value	232			482			467			701
Income from real estate investments	200			200			400			400
Other	112			9			290			137
Gross investment income	768			1,019			1,494			1,665
Investment expenses	(19		)	(9		)	(46		)	(17		)
Net investment income	$	749		$	1,010		$	1,448		$	1,648

Gross realized gains and losses on available-for-sale investments and limited liability investments for the three and six months ended June 30, 2019 and June 30, 2018 are comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Gross realized gains	$	44		$	133		$	359		$	398
Gross realized losses	(600		)	(1		)	(600		)	(1		)
Net realized (losses) gains	$	(556	)	$	132		$	(241	)	$	397

19

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

(Loss) gain on change in fair value of equity investments for the three and six months ended June 30, 2019 and June 30, 2018 is comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Net (losses) gains recognized on equity investments sold during the period	$	(101	)	$	(10	)	$	(101	)	$	545
Change in unrealized gains (losses) on equity investments held at end of the period	38			(411		)	116			199
(Loss) gain on change in fair value of equity investments	$	(63	)	$	(421	)	$	15		$	744

Short-term investments and fixed maturities with an estimated fair value of $0.2 million and $0.2 million at June 30, 2019 and December 31, 2018, respectively, were on deposit with state and provincial regulatory authorities. The Company also has restricted cash of $17.3 million and $17.0 million at June 30, 2019 and December 31, 2018, respectively. Included in restricted cash are (i) $5.1 million and $5.0 million at June 30, 2019 and December 31, 2018, respectively, held in escrow as part of the transaction to sell Mendota; (ii) $10.0 million and $10.0 million at June 30, 2019 and December 31, 2018, respectively, held as deposits by IWS Acquisition Corporation ("IWS"), Professional Warranty Service Corporation ("PWSC"), and Geminus; (iii) $1.9 million and $1.9 million at June 30, 2019 and December 31, 2018, respectively, on deposit with state and provincial regulatory authorities; and (iv) $0.3 million and $0.1 million at June 30, 2019 and December 31, 2018, respectively, pledged to third-parties as deposits or to collateralize liabilities. Collateral pledging transactions are conducted under terms that are common and customary to standard collateral pledging and are subject to the Company's standard risk management controls.

Impact of COVID-19 on Investments

As discussed in Note 24, "Subsequent Event," in March 2020 the outbreak of COVID-19 caused by a novel strain of the coronavirus was recognized as a pandemic by the World Health Organization, and the outbreak has become increasingly widespread in the United States, including in the markets in which we operate. The COVID-19 outbreak has had a notable impact on general economic conditions, including but not limited to the temporary closures of many businesses; "shelter in place" and other governmental regulations; and reduced consumer spending due to both job losses and other effects attributable to COVID-19. There remain many unknowns.

As part of the Company’s March 31, 2020 quarterly impairment analysis of its investments in private companies, the Company determined that it should write-down one of its investments by 90%, or $0.7 million, for other-than-temporary impairments as a result of the impacts of COVID-19 on the investment's underlying business. The Company continues to assess the impact that the COVID-19 pandemic may have on the value of its various investments, which could result in future material decreases in the underlying investment value. Such decreases may be considered temporary or could be deemed to be other-than-temporary and management may be required to record write-downs of the related investments in future reporting periods.

NOTE 7 INVESTMENT IN INVESTEE

Investment in investee includes the Company's investment in the common stock of Itasca Capital Ltd. ("ICL"). The carrying value of the Company’s investment in investee is accounted for under the equity method, calculated using ICL’s reported financial statements. The carrying value, estimated fair value and approximate equity percentage for the Company's investment in investee at June 30, 2019 and December 31, 2018 were as follows:

(in thousands, except for percentages)
	June 30, 2019						December 31, 2018
	Equity Percentage		Estimated Fair Value		Carrying Value		Equity Percentage		Estimated Fair Value		Carrying Value
ICL	22.9	%	$	1,542	$	1,119	22.9	%	$	951	$	951

The estimated fair value of the Company's investment in ICL at June 30, 2019 in the table above is calculated based on the published closing price of ICL at June 30, 2019.

20

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

The carrying value of the Company's investment in investee at December 31, 2018, using ICL’s financial statements reported as of and for the period ended September 30, 2018, was calculated to be $2.7 million. The Company performed an analysis to determine whether its $2.7 million carrying value calculated under the equity method is recoverable. As part of its analysis, the Company considered that the estimated fair value of the Company's investment in investee at December 31, 2018, as presented in the table above and as calculated based on the published closing price of ICL common stock at December 31, 2018, was $1.0 million. The Company concluded that the $2.7 million carrying value of its investment in investee, as calculated under the equity method, had an other-than-temporary impairment as of December 31, 2018. As a result, the Company wrote down the carrying value of its investment in investee as of December 31, 2018, as presented in the table above, by $1.7 million such that its carrying value equaled the $1.0 million estimated fair value of the Company's investment in investee as calculated based on the published closing price of ICL common stock at December 31, 2018.

For the three months ended June 30, 2019 and June 30, 2018, equity in net income (loss) of investee was income of $0.2 million and loss of $0.4 million, respectively (income of $0.2 million and loss of $0.3 million for the six months ended June 30, 2019 and June 30, 2018, respectively). During the fourth quarter of 2019, the Company sold its remaining investment in the common stock of ICL. See Note 22(c), "Related Parties," for more information.

NOTE 8 DEFERRED ACQUISITION COSTS

Deferred acquisition costs consist primarily of commissions and agency expenses incurred related to successful efforts to acquire vehicle service agreements and are amortized over the period in which the related revenues are earned in accordance with ASC 606.

The components of deferred acquisition costs and the related amortization expense for the three and six months ended June 30, 2019 and June 30, 2018 are comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Beginning balance, net	$	7,220		$	6,428		$	6,904		$	6,325
Additions	1,500			1,256			2,701			2,498
Amortization	(996		)	(1,022		)	(1,881		)	(2,161		)
Balance at June 30, net	$	7,724		$	6,662		$	7,724		$	6,662

NOTE 9 INTANGIBLE ASSETS

Intangible assets at June 30, 2019 and December 31, 2018 are comprised as follows:

(in thousands)			June 30, 2019
	Gross Carrying Value			Accumulated Amortization		Net Carrying Value
Intangible assets subject to amortization:
Database	$	4,918		$	3,259	$	1,659
Vehicle service agreements in-force	3,680			3,675		5
Customer relationships	12,646			4,580		8,066
In-place lease	1,125			186		939
Non-compete	266			91		175
Intangible assets not subject to amortization:
Tenant relationship	73,667			—		73,667
Trade names	3,264			—		3,264
Total	$	99,566		$	11,791	$	87,775

21

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

(in thousands)			December 31, 2018
	Gross Carrying Value			Accumulated Amortization		Net Carrying Value
Intangible assets subject to amortization:
Database	$	4,918		$	3,013	$	1,905
Vehicle service agreements in-force	3,680			3,671		9
Customer relationships	8,914			3,691		5,223
In-place lease	1,125			155		970
Non-compete	266			64		202
Intangible assets not subject to amortization:
Tenant relationship	73,667			—		73,667
Trade names	1,290			—		1,290
Total	$	93,860		$	10,594	$	83,266

As further discussed in Note 5, "Acquisition and Discontinued Operations," during the first quarter of 2019, the Company recorded $5.7 million of separately identifiable intangible assets, related to acquired customer relationships and trade names, as part of the acquisition of Geminus. The customer relationships intangible asset of $3.7 million is being amortized over ten years based on the pattern in which the economic benefits of the intangible asset are expected to be consumed. The trade name intangible assets of $2.0 million are deemed to have indefinite useful lives and are not amortized.

The Company's other intangible assets with definite useful lives are amortized either based on the patterns in which the economic benefits of the intangible assets are expected to be consumed or using the straight-line method over their estimated useful lives, which range from seven to eighteen years. Amortization of intangible assets was $0.7 million and $0.3 million for the three months ended June 30, 2019 and June 30, 2018, respectively ($1.2 million and $0.5 million for the six months ended June 30, 2019 and June 30, 2018, respectively).

The tenant relationship and trade name intangible assets have indefinite useful lives and are not amortized. No impairment charges were taken on intangible assets during the three and six months ended June 30, 2019 and June 30, 2018.

NOTE 10 PROPERTY AND EQUIPMENT

Property and equipment at June 30, 2019 and December 31, 2018 are comprised as follows:

(in thousands)					June 30, 2019
	Total Property and Equipment							Property leased to others under operating leases included in property and equipment
	Cost		Accumulated Depreciation			Carrying Value		Cost		Accumulated Depreciation		Carrying Value
Land	$	21,120	$	—		$	21,120	$	21,120	$	—	$	21,120
Site improvements	91,308		12,228			79,080		91,308		12,228		79,080
Buildings	580		43			537		580		43		537
Leasehold improvements	149		103			46		—		—		—
Furniture and equipment	1,042		953			89		—		—		—
Computer hardware	5,289		4,983			306		—		—		—
Total	$	119,488	$	18,310		$	101,178	$	113,008	$	12,271	$	100,737

22

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

(in thousands)			December 31, 2018
	Total Property and Equipment							Property leased to others under operating leases included in property and equipment
	Cost			Accumulated Depreciation		Carrying Value		Cost		Accumulated Depreciation		Carrying Value
Land	$	21,120		$	—	$	21,120	$	21,120	$	—	$	21,120
Site improvements	91,308			10,161		81,147		91,308		10,161		81,147
Buildings	580			36		544		580		36		544
Leasehold improvements	104			102		2		—		—		—
Furniture and equipment	993			901		92		—		—		—
Computer hardware	4,995			4,758		237		—		—		—
Total	$	119,100		$	15,958	$	103,142	$	113,008	$	10,197	$	102,811

NOTE 11 VEHICLE SERVICE AGREEMENT LIABILITY

Vehicle service agreement fees include the fees collected to cover the costs of future automobile mechanical breakdown claims and the associated administration of those claims. Vehicle service agreement fees are initially recorded as deferred service fees. On a quarterly basis, the Company compares the remaining deferred service fees balance to the estimated amount of expected future claims under the vehicle service agreement contracts and records an additional accrual when the deferred service fees balance is less than expected future claims costs.

In certain jurisdictions the Company is required to refund to a customer a pro-rata share of the vehicle service agreement fees if a customer cancels the agreement prior to the end of the term. Depending on the jurisdiction, the Company may be entitled to deduct from the refund a cancellation fee and/or amounts for claims incurred prior to cancellation. While refunds vary depending on the term and type of product offered, historically refunds have averaged 9% to 13% of the original amount of the vehicle service agreement fee. Revenues recorded by the Company are net of refunds and the associated refund liability is included in deferred service fees.

A reconciliation of the changes in the vehicle service agreement liability, including deferred service fees related to vehicle service agreements, as of June 30, 2019 and June 30, 2018 were as follows:

(in thousands)	June 30, 2019			June 30, 2018
Balance at January 1, net	$	43,734		$	40,794
Vehicle service agreement liability acquired during the year related to the purchase of Geminus	10,792			—
Gross service fees for vehicle service agreements sold	14,549			11,166
Recognition of service fees on vehicle service agreements	(12,703		)	(9,588		)
Liability for claims authorized on vehicle service agreements	4,393			2,764
Payments of claims authorized on vehicle service agreements	(2,678		)	(2,950		)
Re-estimation of deferred service fees	(321		)	(165		)
Balance at June 30, net	$	57,766		$	42,021

The vehicle service agreement liability is presented as components of deferred services fees and accrued expenses and other liabilities in the consolidated balance sheets as follows:

(in thousands)	June 30,		December 31,
	2019		2018
Deferred service fees	$	57,182	$	43,495
Accrued expenses and other liabilities	584		239
Balance at end of period, net	$	57,766	$	43,734

23

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

NOTE 12 UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES

The establishment of the provision for unpaid loss and loss adjustment expenses is based on known facts and interpretation of circumstances and is, therefore, a complex and dynamic process influenced by a large variety of factors. These factors include the Company's experience with similar cases and historical trends involving loss payment patterns, pending levels of unpaid loss and loss adjustment expenses, product mix or concentration, loss severity and loss frequency patterns.

Other factors include the continually evolving and changing regulatory and legal environment; actuarial studies; professional experience and expertise of the Company's claims departments' personnel and independent adjusters retained to handle individual claims; the quality of the data used for projection purposes; existing claims management practices including claims-handling and settlement practices; the effect of inflationary trends on future loss settlement costs; court decisions; economic conditions; and public attitudes.

Consequently, the process of determining the provision for unpaid loss and loss adjustment expenses necessarily involves risks that the actual loss and loss adjustment expenses incurred by the Company will deviate, perhaps materially, from the estimates recorded.

The Company's evaluation of the adequacy of unpaid loss and loss adjustment expenses includes a re-estimation of the liability for unpaid loss and loss adjustment expenses relating to each preceding financial year compared to the liability that was previously established.

The results of this comparison and the changes in the provision for unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of June 30, 2019 and June 30, 2018 were as follows:

(in thousands)	June 30, 2019			June 30, 2018
Balance at beginning of period, gross	$	2,073		$	1,329
Less reinsurance recoverable related to unpaid loss and loss adjustment expenses	—			72
Balance at beginning of period, net	2,073			1,257
Incurred related to:
Current year	—			—
Prior years	708			1,647
Paid related to:
Current year	—			—
Prior years	(844		)	(410		)
Balance at end of period, net	1,937			2,494
Plus reinsurance recoverable related to unpaid loss and loss adjustment expenses	—			100
Balance at end of period, gross	$	1,937		$	2,594

The Company reported unfavorable development on unpaid loss and loss adjustment expenses of $0.7 million and $1.6 million for the six months ended June 30, 2019 and June 30, 2018, respectively. The unfavorable development for the six months ended June 30, 2019 and June 30, 2018 was primarily related to an increase in loss and loss adjustment expenses at Amigo.

24

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

NOTE 13 DEBT

Debt consists of the following instruments at June 30, 2019 and December 31, 2018:

(in thousands)	June 30, 2019						December 31, 2018
	Principal		Carrying Value		Fair Value		Principal		Carrying Value		Fair Value
Bank loans:
PWSC Loan	$	2,717	$	2,717	$	2,656	$	3,917	$	3,917	$	3,829
KWH Loan	9,875		8,957		12,246		—		—		—
	12,592		11,674		14,902		3,917		3,917		3,829
Notes payable:
Mortgage	171,551		180,484		181,042		173,155		182,548		174,265
Flower Note	7,555		7,555		8,322		7,768		7,768		8,565
Net Lease Note	9,000		9,000		9,151		9,000		9,000		9,409
	188,106		197,039		198,515		189,923		199,316		192,239
Subordinated debt	90,500		50,224		50,224		90,500		50,023		50,023
Total	$	291,198	$	258,937	$	263,641	$	284,340	$	253,256	$	246,091

(a)          Bank loans:

As part of the acquisition of PWSC on October 12, 2017, the Company borrowed a principal amount of $5.0 million from a bank at a fixed interest rate of 5.0% (the "PWSC Loan"). The carrying value of the PWSC Loan represents its unpaid principal balance. The fair value of the PWSC Loan disclosed in the table above is derived from quoted market prices of B and B minus rated industrial bonds with similar maturities. The PWSC Loan was scheduled to mature on October 12, 2022; however, the principal totaling $0.3 million was fully repaid on January 30, 2020.

As part of the acquisition of Geminus on March 1, 2019, the Company formed Kingsway Warranty Holdings LLC ("KWH") and contributed IWS and Trinity to KWH, which then borrowed a principal amount of $10.0 million from a bank at an annual interest rate equal to LIBOR plus 9.25% (the "KWH Loan"), using most of the proceeds to acquire Geminus. The KWH Loan matures on March 1, 2024. As part of the KWH Loan, KWH also issued warrants (the "KWH Warrants") to the lender exercisable to purchase an aggregate 1.25% membership interest in KWH. The Company allocated $0.4 million of the KWH loan proceeds to a liability, recorded as part of accrued expenses and other liabilities in the consolidated balance sheets, to reflect the estimated fair value of the KWH Warrants, as the warrants contain a put right exercisable by the holder. Changes in the estimated fair value of the KWH Warrants are recorded in the consolidated statements of operations. The Company also recorded as a discount to the carrying value of the KWH Loan issuance costs of $1.0 million specifically related to the KWH Loan. The KWH Loan is carried in the consolidated balance sheets at its amortized cost, which reflects the quarterly pay-down of principal as well as the amortization of the discount using the effective interest rate method. The fair value of the KWH Loan disclosed in the table above is derived from quoted market prices of B and BB minus rated industrial bonds with similar maturities. The KWH Loan is secured by certain of the equity interests and assets of KWH and its subsidiaries.

(b)          Notes payable:

As part of the acquisition of CMC Industries, Inc. ("CMC") in July 2016, the Company assumed a mortgage, which is recorded as note payable in the consolidated balance sheets ("the Mortgage"). The Mortgage is nonrecourse indebtedness with respect to CMC and its subsidiaries, and the Mortgage is not, nor will it be, guaranteed by Kingsway or its affiliates. The Mortgage was recorded at its estimated fair value of $191.7 million, which included the unpaid principal amount of $180.0 million as of the date of acquisition plus a premium of $11.7 million. The Mortgage matures on May 15, 2034 and has a fixed interest rate of 4.07%. The Mortgage is carried in the consolidated balance sheets at its amortized cost, which reflects the monthly pay-down of principal as well as the amortization of the premium using the effective interest rate method. The fair value of the Mortgage disclosed in the table above is derived from quoted market prices of A-rated industrial bonds with similar maturities.

On January 5, 2015, Flower Portfolio 001, LLC ("Flower") assumed a $9.2 million mortgage in conjunction with the purchase of investment real estate properties, which is recorded as note payable in the consolidated balance sheets ("the Flower Note"). The Flower Note requires monthly payments of principal and interest and is secured by certain investments of Flower. The Flower Note matures on December 10, 2031 and has a fixed interest rate of 4.81%. The carrying value of the Flower Note at June 30, 2019 of $7.6 million represents its unpaid principal balance. The fair value of the Flower Note disclosed in the table above is derived from quoted market prices of A and B rated industrial bonds with similar maturities.

25

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

On October 15, 2015, Net Lease assumed a $9.0 million mezzanine debt in conjunction with the purchase of investment real estate properties, which is recorded as note payable in the consolidated balance sheets ("the Net Lease Note"). The Net Lease Note requires monthly payments of interest and is secured by certain investments of Net Lease. The Net Lease Note matures on November 1, 2020 and has a fixed interest rate of 10.25%. The carrying value of the Net Lease Note at June 30, 2019 of $9.0 million represents its unpaid principal balance. The fair value of the Net Lease Note disclosed in the table above is derived from quoted market prices of B and B minus rated industrial bonds with similar maturities.

(c)          Subordinated debt:

The subordinated debt is carried in the consolidated balance sheets at fair value. See Note 21, "Fair Value of Financial Instruments," for further discussion of the subordinated debt. Of the $0.2 million increase in fair value of the Company’s subordinated debt between December 31, 2018 and June 30, 2019, $1.7 million is reported as change in fair value of debt attributable to instrument-specific credit risk in the Company's consolidated statements of comprehensive (loss) income, partially offset by $1.5 million reported as gain on change in fair value of debt in the Company’s consolidated statements of operations.

During the third quarter of 2018, the Company gave notice to its Trust Preferred trustees of its intention to exercise its voluntary right to defer interest payments for up to 20 quarters, pursuant to the contractual terms of its outstanding Trust Preferred indentures, which permit interest deferral. This action does not constitute a default under the Company's Trust Preferred indentures or any of its other debt indentures. At June 30, 2019, deferred interest payable of $5.7 million is included in accrued expenses and other liabilities in the consolidated balance sheets.

Subordinated debt consists of the following trust preferred debt instruments:

Issuer	Principal (in thousands)		Issue date	Interest	Redemption date
Kingsway CT Statutory Trust I	$	15,000	12/4/2002	annual interest rate equal to LIBOR, plus 4.00% payable quarterly	12/4/2032
Kingsway CT Statutory Trust II	$	17,500	5/15/2003	annual interest rate equal to LIBOR, plus 4.10% payable quarterly	5/15/2033
Kingsway CT Statutory Trust III	$	20,000	10/29/2003	annual interest rate equal to LIBOR, plus 3.95% payable quarterly	10/29/2033
Kingsway DE Statutory Trust III	$	15,000	5/22/2003	annual interest rate equal to LIBOR, plus 4.20% payable quarterly	5/22/2033
Kingsway DE Statutory Trust IV	$	10,000	9/30/2003	annual interest rate equal to LIBOR, plus 3.85% payable quarterly	9/30/2033
Kingsway DE Statutory Trust VI	$	13,000	12/16/2003	annual interest rate equal to LIBOR, plus 4.00% payable quarterly	1/8/2034

NOTE 14 LEASES

Financial Statement Impact of Adopting Accounting Standards Update No. 2016-02 "Leases (Topic 842)" ("ASU 2016-02" or "ASC 842")

The Company adopted ASU 2016-02 on January 1, 2019 using the modified retrospective adoption method. The reported results for 2019 reflect the adoption of ASC 842 guidance while the reported results for 2018 were prepared and continue to be reported under the guidance of ASC 840, Leases, referred to herein as "previous guidance."

ASC 842 provides guidance for both lessees and lessors. The Company is the lessee where it leases certain office properties from lessors. The Company is the lessor when it leases certain property to lessees.

The guidance requires lessees to recognize right-of-use assets and lease liabilities in the balance sheet and disclose key information about leasing arrangements, such as information about variable lease payments and options to renew and terminate leases. The amended guidance will require both operating and finance leases to be recognized in the balance sheet. A lessee should recognize in the statement of financial position a liability to make lease payments (the lease liability) and a right-of-use asset ("ROU") representing its right to use the underlying asset for the lease term.

The guidance requires lessors to classify leases as a sales-type, direct financing, or operating lease. A lease is classified as a sales-type lease if any one of five criteria are met, each of which indicate that the lease, in effect, transfers control of the underlying asset to the lessee. If none of those five criteria are met, but two additional criteria are both met, indicating that the lessor has transferred substantially all the risks and benefits of the underlying asset to the lessee and a third party, the lease is classified as a direct financing lease. All leases that are not classified as sales-type or direct financing leases are classified as operating leases.

26

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

The Company elected certain of the practical expedients that are permitted under the transition guidance which allowed the Company to carryforward the historical lease classification, not reassess initial direct costs for any existing leases as of January 1, 2019 or reassess whether any expired or existing contracts are or contain leases. In addition, the Company elected to adopt the “hindsight” practical expedient to determine the reasonably certain lease term for existing leases. The Company has revised its relevant policies and procedures, as applicable, to meet the new accounting, reporting and disclosure requirements of ASC 842 and have updated internal controls accordingly.

The main difference between the guidance in ASU 2016-02 and prior guidance for lessees is the recognition of right-of-use assets and lease liabilities for those leases classified as operating leases. Recognition of the right-of-use assets and liabilities had a material impact to the Company’s consolidated balance sheet upon adoption. However, since all its leases are operating leases under ASC 840 and the Company will carryforward the historical lease classification, the new standard did not have a material impact on the Company’s consolidated statements of operations, consolidated statements of shareholder’s equity, or consolidated statements of cash flows.

The adoption resulted in an increase of the ROU assets of approximately $2.7 million and lease liabilities of $2.9 million. The difference of $0.2 million relates to straight-line rent accruals and lease incentive liabilities that were reclassified to ROU assets for operating leases.

The main difference between the guidance in ASU 2016-02 and prior guidance for lessors is a modification of what qualifies as a sales-type and direct financing lease. All the Company’s lessor leases are classified as operating leases.

Lease Accounting Policy

The Company determines lease classification at commencement date. Leases not classified as sales-type (lessor) or financing leases (lessor and lessee) are classified as operating leases. The primary accounting criteria the Company uses that results in operating lease classification are: (a) the lease does not transfer ownership of the underlying asset to the lessee by the end of the lease term, (b) the lease does not grant the lessee a purchase option that the lessee is reasonably certain to exercise, (c) using a seventy-five percent or more threshold, the lease term is not for a major part of the remaining economic life of the underlying asset, (d) using a ninety percent or more threshold, the present value of the sum of the lease payments and residual value guarantee from the lessee does not equal or substantially exceeds all of the fair value of the underlying asset.

Rental income from operating leases is recognized on a straight-line basis, based on contractual lease terms with fixed and determinable increases over the non-cancellable term of the related lease when collectability is reasonably assured. Rental expense for operating leases is recognized on a straight-line basis over the lease term, net of any applicable lease incentive amortization.

Lessee Leases

The Company has operating leases for office space which include fixed base rent payments, as well as variable rent payments to reimburse the landlord for operating expenses and taxes. The Company’s variable lease payments do not depend on a published index or rate, and therefore, are expensed as incurred. The Company includes only fixed payments for lease components in the measurement of the right-of-use asset and lease liability. There are no residual value guarantees. The Company does not currently have leases that meet the finance lease classification as defined under ASC 842.

The Company treats contracts as a lease when the contract: (1) conveys the right to use a physically distinct asset for a period of time in exchange for consideration, (2) the Company directs the use of the asset and (3) the Company obtains substantially all the economic benefits of the asset. Right-of-use assets and lease liabilities are measured and recognized based on the present value of the future minimum lease payments over the lease term at the commencement date. As the Company’s leases are office leases, the Company is unable to determine an implicit rate; therefore, the Company uses its incremental borrowing rate based on the information available at the lease commencement date in determining the present value of future payments for those leases. The Company includes options to extend or terminate the lease in the measurement of the right-of-use asset and lease liability when it is reasonably certain that such options will be exercised. Lease expense for minimum lease payments is recognized on a straight-line basis over the lease term.

As an accounting policy, the Company has elected not to apply the recognition requirements in ASC 842 to short-term leases (generally those with terms of twelve months or less). Instead, the Company recognizes the lease payments as expense on a straight-line basis over the lease term and any variable lease payments in the period in which the obligation for those payments is incurred.

The ROU assets and lease liability are presented as separate line items on the face of the Company’s consolidated balance sheet as of June 30, 2019.

27

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

Operating lease costs and variable lease costs included in selling and administrative costs for the three months ended June 30, 2019 were $0.2 million and de minimis, respectively. Operating lease costs and variable lease costs included in selling and administrative costs for the six months ended June 30, 2019 were $0.5 million and de minimis, respectively.

The annual maturities of lease liabilities as of June 30, 2019 were as follows:

(in thousands)	Lease Commitments
2019	$	463
2020	377
2021	388
2022	399
2023	422
2024 and thereafter	859
Total undiscounted lease payments	2,908
Imputed interest	498
Total lease liabilities	$	2,410

The weighted-average remaining lease term for our operating leases was 6.40 years as of June 30, 2019. The weighted average discount rate of our operating leases was 5.69% as of June 30, 2019. Cash paid for amounts included in the measurement of lease liabilities was $0.5 million for the six months ended June 30, 2019.

Lessor Leases

The Company owns a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property") that is subject to a long-term triple net lease agreement with an unrelated third-party. The lease provides for future rent escalations and renewal options. The initial lease term ends in May 2034. The lessee bears the cost of maintenance and property taxes. Rental income from operating leases is recognized on a straight-line basis, based on contractual lease terms with fixed and determinable increases over the non-cancellable term of the related lease when collectability is reasonably assured. Rental income includes a de minimus amount of amortization of below market lease liabilities for the three and six months ended June 30, 2019 and June 30, 2018. The estimated aggregate future amortization of below market lease liabilities is $0.1 million for 2019, $0.1 million for 2020, $0.1 million for 2021, $0.1 million for 2022 and $0.1 million for 2023. Realization of the residual values of the assets under lease is dependent on the future ability to market the assets under prevailing market conditions. The lease is classified as an operating lease and the underlying leased assets are included in Property and Equipment (Note 10, "Property and Equipment").

Lease income related to operating leases for the three months ended June 30, 2019 and June 30, 2018 was $3.3 million and $3.3 million, respectively ($6.7 million year to date compared to $6.7 million prior year to date).

The following table provides the net book value of operating lease property included in property and equipment in the consolidated balance sheets:

(in thousands)	As of June 30, 2019
Property leased to lessees	113,008
Accumulation depreciation	(12,271		)
Net property and equipment leased	$	100,737

As of June 30, 2019, future undiscounted cash flows to be received in each of the next five years and thereafter, on non-cancelable operating leases are as follows:

(in thousands)
2019	$	5,840
2020	11,832
2021	12,099
2022	12,371
2023	12,649
Thereafter	149,896

NOTE 15 REVENUE FROM CONTRACTS WITH CUSTOMERS

Revenue from contracts with customers relates to Extended Warranty segment service fee and commission income. Service fee and commission income represents vehicle service agreement fees, GAP commissions, maintenance support service fees, warranty product commissions, homebuilder warranty service fees and homebuilder warranty commissions based on terms of various agreements with credit unions, consumers, businesses and homebuilders. Customers either pay in full at the inception of a warranty contract or commission product sale, or on terms subject to the Company’s customary credit reviews.

The following table disaggregates revenues from contracts with customers by revenue type:

(in thousands)	Three months ended June 30,				Six months ended June 30,
	2019		2018		2019		2018
Vehicle service agreement fees - IWS	$	4,551	$	4,226	$	9,030	$	8,615
GAP commissions - IWS	226		200		484		392
Maintenance support service fees - Trinity	1,732		1,962		3,700		4,935
Warranty product commissions - Trinity	817		736		1,399		1,232
Homebuilder warranty service fees - PWSC	1,475		1,548		2,898		2,975
Homebuilder warranty commissions - PWSC	198		188		409		362
Vehicle service agreement fees - Geminus	2,757		—		3,644		—
GAP commissions - Geminus	16		—		23		—
Service fee and commission income	$	11,772	$	8,860	$	21,587	$	18,511

IWS' vehicle service agreement fees include the fees collected to cover the costs of future automobile mechanical breakdown claims and the associated administration of those claims. Vehicle service agreement contract fees are earned over the duration of the vehicle service agreement contracts as the single performance obligation is satisfied.

IWS' GAP commissions include fees collected from the sale of GAP contracts. IWS acts as an agent on behalf of the third-party insurance company that underwrites and guaranties these GAP contracts. IWS does not assume any insurance risk from the sale of GAP contracts. IWS receives a single commission fee as its transaction price at the time it sells a GAP contract to a customer. Each GAP contract contains two separate performance obligations - sale of a GAP contract and GAP claims administration. The first performance obligation is related to the sale of a GAP contract and is satisfied upon closing the sale. The second performance obligation is related to the administration of claims during the GAP contract period, generally four years.

Standalone selling prices are not directly observable in the GAP contract for each of the separate performance obligations. As a result, IWS has applied the expected cost plus a margin approach to develop models to estimate the standalone selling price for each of its performance obligations in order to allocate the transaction price to the two separate performance obligations identified.

For the model related to the sale of a GAP contract performance obligation, IWS makes judgments about which of its actual costs are associated with selling activities. For the model related to the GAP claims administration performance obligation, IWS makes judgments about which of its actual costs are associated with claim-handling activities, which are performed over the life of the GAP contract period. The relative percentage of expected costs plus a margin associated with the sale of a GAP contract performance obligation is applied to the transaction price to determine the estimated standalone selling price of the sale of a GAP contract performance obligation, which IWS recognizes as earned at the time of the GAP contract sale. The relative percentage of expected costs plus a margin associated with the GAP claims administration performance obligation is applied to the transaction price to determine the estimated standalone selling price of the GAP claims administration performance obligation, which IWS recognizes as earned as services are performed over the GAP contract period.

For the GAP claims administration performance obligation, IWS applies an input method of measurement, based on the expected costs plus a margin of providing services, to determine the transfer of its services over the GAP contract period. IWS uses historical data regarding the number of claims it receives and activities performed, in addition to the number of GAP contracts sold, to estimate the number of claims to be received by year until coverage expires, which allows IWS to develop a revenue recognition

28

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

pattern that it believes provides a faithful depiction of the transfer of services over time for the GAP claims administration performance obligation.

Trinity Warranty Solutions LLC's (Trinity") maintenance support service fees include the service fees collected to administer equipment breakdown and maintenance support services and are earned as services are rendered.

Trinity’s warranty product commissions include the commissions from the sale of warranty contracts for certain new and used heating, ventilation, air conditioning ("HVAC"), standby generator, commercial LED lighting and refrigeration equipment. Trinity acts as an agent on behalf of the third-party insurance companies that underwrite and guaranty these warranty contracts. Trinity does not guaranty the performance underlying the warranty contracts it sells. Warranty product commissions are earned at the time of the warranty product sales.

PWSC’s homebuilder warranty service fees include fees collected from the sale of warranties issued by new homebuilders. PWSC receives a single warranty service fee as its transaction price at the time it enters into a written contract with each of its builder customers. Each contract contains two separate performance obligations - warranty administrative services and other warranty services. Warranty administrative services include enrolling each home sold by the builder into the program and the warranty administrative system and delivering the warranty product. Other warranty services include answering builder or homeowner questions regarding the home warranty and dispute resolution services.

Standalone selling prices are not directly observable in the contract for each of the separate performance obligations. As a result, PWSC has applied the expected cost plus a margin approach to develop models to estimate the standalone selling price for each of its performance obligations in order to allocate the transaction price to the two separate performance obligations identified.

For the model related to the warranty administrative services performance obligation, PWSC makes judgments about which of its actual costs are associated with enrolling each home sold by the builder into the program and the warranty administrative system and delivering the warranty product. For the model related to the other warranty services performance obligation, PWSC makes judgments about which of its actual costs are associated with activities, such as answering builder or homeowner questions regarding the home warranty and dispute resolution services, which are performed over the life of the warranty coverage period. The relative percentage of expected costs plus a margin associated with the warranty administrative services performance obligation is applied to the transaction price to determine the estimated standalone selling price of the warranty administrative services performance obligation, which PWSC recognizes as earned at the time the home is enrolled and the warranty product is delivered. The relative percentage of expected costs plus a margin associated with the other warranty services performance obligation is applied to the transaction price to determine the estimated standalone selling price of the other warranty services performance obligation, which PWSC recognizes as earned as services are performed over the warranty coverage period.

For the other warranty services performance obligation, PWSC applies an input method of measurement, based on the expected costs plus a margin of providing services, to determine the transfer of its services over the warranty coverage period. PWSC uses historical data regarding the number of calls it receives and activities performed, in addition to the number of homes enrolled, to estimate the number of complaints and dispute resolution requests to be received by year until coverage expires, which allows PWSC to develop a revenue recognition pattern that it believes provides a faithful depiction of the transfer of services over time for the other warranty services performance obligation.

PWSC’s homebuilder warranty commissions include commissions from the sale of warranty contracts for those builders who have requested and receive insurance backing of their warranty obligations. PWSC acts as an agent on behalf of the third-party insurance company that underwrites and guaranties these warranty contracts. Homebuilder warranty commissions are earned on the certification date, which is typically the date of the closing of the sale of the home to the buyer. The Company also earns fees to manage remediation or repair services related to claims on insurance-backed warranty obligations, which are earned when the claims are closed, and a profit-sharing bonus on eligible warranties, which is determined based on expected ultimate loss ratio targets and is earned at the time the profit-sharing bonus is received.

Geminus' vehicle service agreement fees include the fees collected to cover the costs of future automobile mechanical breakdown claims and the associated administration of those claims. Vehicle service agreement contract fees are earned over the duration of the vehicle service agreement contracts as the single performance obligation is satisfied.

Receivables from contracts with customers are reported as service fee receivable, net in the consolidated balance sheets and at June 30, 2019 and December 31, 2018 were $5.2 million and $3.4 million, respectively.

29

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

The Company records deferred service fees resulting from contracts with customers when payment is received in advance of satisfying the performance obligations. The Company expects to recognize within one year as service fee and commission income approximately 40.5% of the deferred service fees as of June 30, 2019. Approximately $7.9 million of service fee and commission income recognized during the six months ended June 30, 2019 was included in deferred service fees as of December 31, 2018.

NOTE 16 INCOME TAXES

The Tax Cuts and Jobs Act (the "Tax Act") was enacted on December 22, 2017. The Tax Act makes broad and complex changes to the U.S. tax code, including a permanent reduction in the U.S. federal corporate income tax rate to 21% starting in 2018. Previously, the Company was subject to a 34% U.S. federal corporate income tax rate.

Income tax expense (benefit) for the three and six months ended June 30, 2019 and June 30, 2018 varies from the amount that would result by applying the applicable U.S. federal corporate income tax rate of 21% to loss from continuing operations before income tax expense (benefit). The following table summarizes the differences:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Income tax (benefit) expense at United States statutory income tax rate	$	(48	)	$	(855	)	$	472		$	(1,348	)
Valuation allowance	97			822			(1,234		)	1,354
Non-deductible compensation	25			62			34			123
Disposition of subsidiary	(24		)	—			(24		)	—
State income tax	32			67			58			133
Change in unrecognized tax benefits(1)	71			60			141			130
Indefinite life intangibles	54			24			87			46
Foreign operations subject to different tax rates	(20		)	(39		)	(17		)	(54		)
Other	(19		)	49			(62		)	60
Income tax expense (benefit)	$	168		$	190		$	(545	)	$	444
(1) Includes interest and penalty expense related to unrecognized tax benefits.

The Company maintains a valuation allowance for its gross deferred tax assets at June 30, 2019 and December 31, 2018. The Company's operations have generated substantial operating losses in prior years. These losses can be available to reduce income taxes that might otherwise be incurred on future taxable income; however, it is uncertain whether the Company will generate the taxable income necessary to utilize these losses or other reversing temporary differences. This uncertainty has caused management to place a full valuation allowance on its June 30, 2019 and December 31, 2018 net deferred tax asset, excluding the deferred income tax asset and liability amounts set forth in the paragraph below. In the quarter ended March 31, 2019, the Company released into income $0.8 million of its valuation allowance, as a result of its acquisition of Geminus, due to net deferred income tax liabilities that are expected to reverse during the period in which the Company will have deferred income tax assets available.

The Company carries net deferred income tax liabilities of $29.0 million and $28.5 million at June 30, 2019 and December 31, 2018, respectively. At June 30, 2019, $8.0 million relates to deferred income tax liabilities scheduled to reverse in periods after the expiration of the Company's consolidated U.S. net operating loss carryforwards, $21.7 million relates to deferred income tax liabilities associated with land and indefinite lived intangible assets, $0.6 million relates to deferred income tax assets associated with state income taxes and $0.1 million relates to deferred income tax assets associated with alternative minimum tax credits. At December 31, 2018, $8.0 million relates to deferred income tax liabilities scheduled to reverse in periods after the expiration of the Company's consolidated U.S. net operating loss carryforwards, $21.1 million relates to deferred income tax liabilities associated with land and indefinite lived intangible assets, $0.5 million relates to deferred income tax assets associated with state income taxes and $0.1 million relates to deferred income tax assets associated with alternative minimum tax credits. The Company considered a tax planning strategy in arriving at its December 31, 2018 net deferred income tax liabilities.

As of June 30, 2019 and December 31, 2018, the Company carried a liability for unrecognized tax benefits of $1.4 million and $1.4 million, respectively, which is included in income taxes payable in the consolidated balance sheets. The Company classifies interest and penalty accruals, if any, related to unrecognized tax benefits as income tax expense. The Company recorded income tax expense of $0.1 million and $0.1 million related to interest and penalty accruals for the three months ended June 30, 2019 and

30

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

June 30, 2018, respectively ($0.1 million and $0.1 million for the six months ended June 30, 2019 and June 30, 2018, respectively). At June 30, 2019 and December 31, 2018, the Company carried an accrual for the payment of interest and penalties of $1.2 million and $1.1 million, respectively, included in income taxes payable in the consolidated balance sheets.

NOTE 17 (LOSS) EARNINGS FROM CONTINUING OPERATIONS PER SHARE

The following table sets forth the reconciliation of numerators and denominators for the basic and diluted (loss) earnings from continuing operations per share computation for the three and six months ended June 30, 2019 and June 30, 2018:

(in thousands, except per share data)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Numerator:
(Loss) income from continuing operations	$	(396	)	$	(4,262	)	$	2,793		$	(6,866	)
Less: net income attributable to noncontrolling interests	(258		)	(158		)	(469		)	(517		)
Less: dividends on preferred stock, net of tax	(252		)	(259		)	(498		)	(512		)
(Loss) income from continuing operations attributable to common shareholders	$	(906	)	$	(4,679	)	$	1,826		$	(7,895	)
Denominator:
Weighted average basic shares
Weighted average common shares outstanding	21,867			21,708			21,854			21,708
Weighted average diluted shares
Weighted average common shares outstanding	21,867			21,708			21,854			21,708
Effect of potentially dilutive securities
Stock options	—			—			—			—
Unvested restricted stock awards	—			—			—			—
Unvested restricted stock units	—			—			—			—
Warrants	—			—			—			—
Convertible preferred stock	—			—			—			—
Total weighted average diluted shares	21,867			21,708			21,854			21,708
Basic (loss) earnings from continuing operations per share	$	(0.04	)	$	(0.22	)	$	0.08		$	(0.36	)
Diluted (loss) earnings from continuing operations per share	$	(0.04	)	$	(0.22	)	$	0.08		$	(0.36	)

Basic (loss) earnings from continuing operations per share is calculated using weighted-average common shares outstanding. Diluted (loss) earnings from continuing operations per share is calculated using weighted-average diluted shares. Weighted-average diluted shares is calculated by adding the effect of potentially dilutive securities to weighted-average common shares outstanding. Potentially dilutive securities consist of stock options, unvested restricted stock awards, unvested restricted stock units, warrants and convertible preferred stock. Because the Company is reporting a loss from continuing operations for the three months ended June 30, 2019 and June 30, 2018 and the six months ended June 30, 2018, all potentially dilutive securities outstanding were excluded from the calculation of diluted loss from continuing operations per share since their inclusion would have been anti-dilutive.

31

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

NOTE 18 STOCK-BASED COMPENSATION

(a)     Stock Options

The following table summarizes the stock option activity during the six months ended June 30, 2019:

	Number of Options Outstanding	Weighted-Average Exercise Price		Weighted-Average Remaining Contractual Term (in Years)	Aggregate Intrinsic Value (in Thousands)
Outstanding at December 31, 2018	40,000	$	4.67	1.3	$	—
Granted	—	—
Expired	—	—
Outstanding at June 30, 2019	40,000	$	4.67	0.8	$	—
Exercisable at June 30, 2019	40,000	$	4.67	0.8	$	—

The aggregate intrinsic value of stock options outstanding and exercisable is the difference between the June 30, 2019 market price for the Company's common shares and the exercise price of the options, multiplied by the number of options where the fair value exceeds the exercise price.

The Company uses the Black-Scholes option pricing model to estimate the fair value of each option on the date of grant. No options were granted during the six months ended June 30, 2019.

(b)     Restricted Stock Awards

Under the 2013 Equity Incentive Plan (the "2013 Plan"), the Company made grants of restricted common stock awards to certain officers of the Company on March 28, 2014 (the "2014 Restricted Stock Awards"). The 2014 Restricted Stock Awards shall become fully vested and the restriction period shall lapse as of March 28, 2024 subject to the officers' continued employment through the vesting date. The 2014 Restricted Stock Awards are amortized on a straight-line basis over the ten-year requisite service period. The grant-date fair value of the 2014 Restricted Stock Awards was determined using the closing price of Kingsway common stock on the date of grant. Total unamortized compensation expense related to unvested 2014 Restricted Stock Awards at June 30, 2019 was $0.5 million.

During the third quarter of 2018, the Company modified the terms of the 2014 Restricted Stock Awards for two of its officers.

On September 5, 2018, the Company executed an Amended and Restated Restricted Stock Award Agreement ("Amended RSA Agreement") with its former Chief Executive Officer. Under the terms of the Amended RSA Agreement, the former Chief Executive Officer was deemed to have forfeited 1,382,665 shares of the 2014 Restricted Stock Awards. The Company’s accounting policy is to account for forfeitures when they occur. As a result, the Company reversed during the third quarter of 2018 $2.4 million of compensation expense previously recognized from March 28, 2014 through June 30, 2018.

Pursuant to the terms of the Amended RSA Agreement, the Company granted to the former Chief Executive Officer a modified award of 350,000 shares of restricted common stock (the "2018 Restricted Stock Award"). The Company deemed the 2018 Restricted Stock Award to be taxable to the former Chief Executive Officer on the modification date. Pursuant to the terms of the 2013 Plan and the Amended RSA Agreement, the former Chief Executive Officer was entitled to satisfy the tax withholding obligation by authorizing the Company to withhold restricted common shares, which would otherwise be deliverable, having an aggregate fair market value, determined as of the tax date, equal to the tax withholding obligation. The former Chief Executive Officer chose to satisfy the tax withholding obligation in this manner. As a result, the Company cancelled 102,550 of the 350,000 shares of the 2018 Restricted Stock Award.

The remaining 247,450 shares of the 2018 Restricted Stock Award shall become fully vested after the satisfaction of certain performance conditions, as defined in the Amended RSA Agreement. There is no defined term under which the performance conditions must be completed. The unamortized compensation expense for the 2018 Restricted Stock Award will be recognized at the time the performance condition has been satisfied. The grant-date fair value of the 2018 Restricted Stock Award was determined using the closing price of Kingsway common stock on the modification date. Total unamortized compensation expense

32

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

related to the unvested 2018 Restricted Stock Award at June 30, 2019 was $0.6 million. During the fourth quarter of 2019, the Company acquired the remaining 247,450 shares of the 2018 Restricted Stock Award as partial consideration in exchange for selling its remaining investment in the common stock of ICL. See Note 22, "Related Parties," for more information.

On January 31, 2019, the Company executed an Employee Separation Agreement and Release ("Separation Agreement") with a former officer. The Separation Agreement modified the vesting terms related to 115,500 shares of the original 2014 Restricted Stock Awards ("Modified Restricted Stock Award"), such that they became fully vested on January 31, 2019. The Company deemed the Modified Restricted Stock Award to be taxable to the former officer on the vesting date. Pursuant to the terms of the 2013 Plan and the Separation Agreement, the former officer was entitled to satisfy the tax withholding obligation by authorizing the Company to withhold restricted common shares, which would otherwise be deliverable, having an aggregate fair market value, determined as of the tax date, equal to the tax withholding obligation. The former officer chose to satisfy the tax withholding obligation in this manner. As a result, the Company cancelled 36,269 of the 115,500 shares of the Modified Restricted Stock Award and recognized payroll tax expense of $0.1 million during the first quarter of 2019.

The Company also recorded during the first quarter of 2019 $0.1 million of compensation expense equal to the fair value of the remaining 79,231 fully vested shares of the Modified Restricted Stock Award. The grant-date fair value of the Modified Restricted Stock Award was determined using the closing price of Kingsway common stock on the modification date. Total unamortized compensation expense related to the unvested Modified Restricted Stock Award at June 30, 2019 was zero.

The Company granted restricted common stock units ("Restricted Stock Units") to an officer of the Company pursuant to a Restricted Stock Unit Agreement dated August 24, 2016. On September 5, 2018, the Restricted Stock Unit Agreement was cancelled and 500,000 restricted common stock awards were granted to the officer (the "2018 Restricted Stock Award"). There was no change to the vesting terms. The 2018 Restricted Stock Award shall become fully vested and the restriction period shall lapse as of March 28, 2024 subject to the officer's continued employment through the vesting date. The 2018 Restricted Stock Award is amortized on a straight-line basis over the requisite service period. The grant-date fair value of the 2018 Restricted Stock Award was determined using the closing price of Kingsway common stock on the date of grant. Total unamortized compensation expense related to unvested 2018 Restricted Stock Award at June 30, 2019 was $1.8 million.

The following table summarizes the activity related to unvested 2014 Restricted Stock Awards, 2018 Modified Restricted Stock Award, Modified Restricted Stock Award and 2018 Restricted Stock Award (collectively "Restricted Stock Awards") for the six months endedJune 30, 2019:

	Number of Restricted Stock Awards		Weighted-Average Grant Date Fair Value (per Share)
Unvested at December 31, 2018	1,092,450		$	4.51
Vested	(79,231	)	4.14
Cancelled for Tax Withholding	(36,269	)	4.14
Unvested at June 30, 2019	976,950		$	4.55

The unvested balance at June 30, 2019 in the table above is comprised of 229,500 shares of 2014 Restricted Stock Awards, 247,450 shares of 2018 Modified Restricted Stock Award and 500,000 shares of the 2018 Restricted Stock Award.

(c)     Restricted Stock Awards of PWSC

PWSC granted 1,000 restricted common stock awards ("PWSC Restricted Stock Award") to an officer of PWSC pursuant to an agreement dated September 7, 2018. The PWSC Restricted Stock Award contains both a service and a performance condition that affects vesting. The service condition vests according to a graded vesting schedule and shall become fully vested on February 20, 2022 subject to the officer's continued employment through the applicable vesting dates. The service condition component of the PWSC Restricted Stock Award is amortized on a straight-line basis over the requisite service period. The performance condition vests on February 20, 2022 and is based on the internal rate of return of PWSC. Accruals of compensation expense for the performance condition component of the PWSC Restricted Stock Award is estimated based on the probable outcome of the performance condition. The grant-date fair value of the PWSC Restricted Stock Award was estimated using a valuation model. At June 30, 2019, there were 875 unvested shares of the PWSC Restricted Stock Award with a weighted-average grant date fair value of $824.47 per share. Total unamortized compensation expense related to unvested PWSC Restricted Stock Award at June 30, 2019 was $0.7 million.

33

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

Total stock-based compensation expense, inclusive of Stock Options, Restricted Stock Awards and Restricted Stock Awards of PWSC described above, net of forfeitures, was $0.2 million and $0.3 million for the three months ended June 30, 2019 and June 30, 2018, respectively ($0.4 million and $0.6 million for the six months ended June 30, 2019 and June 30, 2018, respectively).

NOTE 19 ACCUMULATED OTHER COMPREHENSIVE INCOME

The tables below detail the changes in the balances of each component of accumulated other comprehensive income, net of tax, for the three and six months ended June 30, 2019 and June 30, 2018 as relates to shareholders' equity attributable to common shareholders on the consolidated balance sheets. On the other hand, the unaudited consolidated statements of comprehensive (loss) income present the components of other comprehensive (loss) income, net of tax, only for the three and six months ended June 30, 2019 and June 30, 2018 and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries.

(in thousands)	Three months ended June 30, 2019
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk			Equity in Other Comprehensive (Loss) Income of Limited Liability Investment			Total Accumulated Other Comprehensive Income
Balance at April 1, 2019	$	(61	)	$	(3,286	)	$	43,314		$	(45	)	$	39,922
Other comprehensive income (loss) arising during the period	115			—			(750		)	—			(635		)
Amounts reclassified from accumulated other comprehensive income	(7		)	—			—			45			38
Net current-period other comprehensive income (loss)	108			—			(750		)	45			(597		)
Balance at June 30, 2019	$	47		$	(3,286	)	$	42,564		$	—		$	39,325

(in thousands)	Three months ended June 30, 2018
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk		Total Accumulated Other Comprehensive Income
Balance at April 1, 2018	$	(891	)	$	(3,286	)	$	40,021	$	35,844
Other comprehensive income (loss) arising during the period	(72		)	—			778		706
Amounts reclassified from accumulated other comprehensive income	(4		)	—			—		(4		)
Net current-period other comprehensive income (loss)	(76		)	—			778		702
Balance at June 30, 2018	$	(967	)	$	(3,286	)	$	40,799	$	36,546

34

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

(in thousands)	Six months ended June 30, 2019
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk			Equity in Other Comprehensive (Loss) Income of Limited Liability Investment			Total Accumulated Other Comprehensive Income
Balance at January 1, 2019	$	(160	)	$	(3,286	)	$	44,259		$	(45	)	$	40,768
Other comprehensive income (loss) arising during the period	220			—			(1,695		)	—			(1,475		)
Amounts reclassified from accumulated other comprehensive income	(13		)	—			—			45			32
Net current-period other comprehensive income (loss)	207			—			(1,695		)	45			(1,443		)
Balance at June 30, 2019	$	47		$	(3,286	)	$	42,564		$	—		$	39,325

(in thousands)	Six months ended June 30, 2018
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk		Total Accumulated Other Comprehensive Income
Balance at January 1, 2018	$	(566	)	$	(3,286	)	$	—	$	(3,852	)
Cumulative effect of adoption of ASU 2016-01	40			—			40,455		40,495
Balance at January 1, 2018, as adjusted	(526		)	(3,286		)	40,455		36,643
Other comprehensive loss arising during the period	(430		)	—			344		(86		)
Amounts reclassified from accumulated other comprehensive income	(11		)	—			—		(11		)
Net current-period other comprehensive loss	(441		)	—			344		(97		)
Balance at June 30, 2018	$	(967	)	$	(3,286	)	$	40,799	$	36,546

35

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

Components of accumulated other comprehensive income were reclassified to the following lines of the unaudited consolidated statements of operations for the three and six months ended June 30, 2019 and June 30, 2018:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Reclassification of accumulated other comprehensive income from unrealized gains (losses) on available-for-sale investments to:
Net realized (losses) gains	$	(38	)	$	5		$	(32	)	$	8
Other-than-temporary impairment loss	—			—			—			—
(Loss) income from continuing operations before income tax expense	(38		)	5			(32		)	8
Income tax expense	—			—			—			—
(Loss) income from continuing operations	(38		)	5			(32		)	8
Income from discontinued operations, net of taxes	—			(1		)	—			3
Net (loss) income	$	(38	)	$	4		$	(32	)	$	11

NOTE 20 SEGMENTED INFORMATION

The Company conducts its business through the following two reportable segments: Extended Warranty and Leased Real Estate.

The Company previously conducted its business through a third reportable segment, Insurance Underwriting. Insurance Underwriting included the following subsidiaries of the Company: Mendota, Amigo and Kingsway Reinsurance Corporation ("Kingsway Re"). As further discussed in Note 5, "Acquisition and Discontinued Operations," on October 18, 2018, the Company announced that it had completed the sale of Mendota. As a result, Mendota has been classified as discontinued operations and the results of their operations are reported separately for all periods presented. As a result of classifying Mendota as discontinued operations, the composition of the Insurance Underwriting segment has changed such that it no longer meets the criteria of a reportable segment. As such, all segmented information has been restated to exclude the Insurance Underwriting segment for all periods presented.

Extended Warranty Segment

Extended Warranty includes the following subsidiaries of the Company: IWS, Trinity, PWSC and Geminus (collectively, "Extended Warranty").

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by credit unions in 23 states and the District of Columbia to their members.

Trinity sells HVAC, standby generator, commercial LED lighting and refrigeration warranty products and provides equipment breakdown and maintenance support services to companies across the United States. As a seller of warranty products, Trinity markets and administers product warranty contracts for certain new and used products in the HVAC, standby generator, commercial LED lighting and refrigeration industries throughout the United States. Trinity acts as an agent on behalf of the third-party insurance companies that underwrite and guaranty these warranty contracts. Trinity does not guaranty the performance underlying the warranty contracts it sells. As a provider of equipment breakdown and maintenance support services, Trinity acts as a single point of contact to its clients for both certain equipment breakdowns and scheduled maintenance of equipment. Trinity will provide such repair and breakdown services by contracting with certain HVAC providers.

PWSC sells new home warranty products and provides administration services to home builders and homeowners across the United States. PWSC distributes its products and services through an in house sales team and through insurance brokers and insurance carriers throughout all states except Alaska and Louisiana.

Geminus sells vehicle service agreements and other finance and service products to used car buyers across the United States. Penn and Prime distribute these products via independent used car dealerships and franchised car dealerships, respectively.

Leased Real Estate Segment

Leased Real Estate includes the Company's subsidiary, CMC, which was acquired on July 14, 2016. CMC owns a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property") that is leased to a third party pursuant to a long-term triple net lease. The Real Property is also subject to the Mortgage. When assessing and measuring the

36

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

operational and financial performance of the Leased Real Estate segment, interest expense related to the Mortgage is included in Leased Real Estate's segment operating income.

Revenues and Operating Income by Reportable Segment

Results for the Company's reportable segments are based on the Company's internal financial reporting systems and are consistent with those followed in the preparation of the unaudited consolidated interim financial statements. The following tables provide financial data used by management. Segment assets are not allocated for management use and, therefore, are not included in the segment disclosures below.

Revenues by reportable segment reconciled to consolidated revenues for the three and six months ended June 30, 2019 and June 30, 2018 were:

(in thousands)	Three months ended June 30,				Six months ended June 30,
	2019		2018		2019		2018
Revenues:
Extended Warranty:
Service fee and commission income	$	11,772	$	8,860	$	21,587	$	18,511
Other income	41		36		116		102
Total Extended Warranty	11,813		8,896		21,703		18,613
Leased Real Estate:
Rental income	3,341		3,341		6,682		6,682
Other income	72		72		142		219
Total Leased Real Estate	3,413		3,413		6,824		6,901
Total segment revenues	15,226		12,309		28,527		25,514
Rental income not allocated to segments	—		4		—		11
Total revenues	$	15,226	$	12,313	$	28,527	$	25,525

37

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

The operating income by reportable segment in the following table is before income taxes and includes revenues and direct segment costs. Total segment operating income reconciled to the consolidated (loss) income from continuing operations for the three and six months ended June 30, 2019 and June 30, 2018 were:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Segment operating income:
Extended Warranty	$	1,035		$	1,090		$	1,602		$	1,936
Leased Real Estate	753			618			1,205			1,492
Total segment operating income	1,788			1,708			2,807			3,428
Net investment income	749			1,010			1,448			1,648
Net realized (losses) gains	(556		)	132			(241		)	397
(Loss) gain on change in fair value of equity investments	(63		)	(421		)	15			744
Gain (loss) on change in fair value of limited liability investments, at fair value	2,347			(525		)	6,612			(1,461		)
Net change in unrealized gain (loss) on private company investments	—			(155		)	19			(155		)
Other-than-temporary impairment loss	—			—			(75		)	—
Interest expense not allocated to segments	(2,339		)	(1,844		)	(4,441		)	(3,561		)
Other income and expenses not allocated to segments, net	(2,597		)	(3,213		)	(4,361		)	(5,625		)
Amortization of intangible assets	(676		)	(254		)	(1,197		)	(509		)
Gain (loss) on change in fair value of debt	918			(142		)	1,494			(1,061		)
Gain on disposal of subsidiary	—			17			—			17
Equity in net income (loss) of investee	201			(385		)	168			(284		)
(Loss) income from continuing operations before income tax expense (benefit)	(228		)	(4,072		)	2,248			(6,422		)
Income tax expense (benefit)	168			190			(545		)	444
(Loss) income from continuing operations	$	(396	)	$	(4,262	)	$	2,793		$	(6,866	)

NOTE 21 FAIR VALUE OF FINANCIAL INSTRUMENTS

Fair value is the price that would be received upon sale of an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date. Fair value is best evidenced by quoted bid or ask price, as appropriate, in an active market. Where bid or ask prices are not available, such as in an illiquid or inactive market, the closing price of the most recent transaction of that instrument subject to appropriate adjustments as required is used. Where quoted market prices are not available, the quoted prices of similar financial instruments or valuation models with observable market-based inputs are used to estimate the fair value. These valuation models may use multiple observable market inputs, including observable interest rates, foreign exchange rates, index levels, credit spreads, equity prices, counterparty credit quality, corresponding market volatility levels and option volatilities. Minimal management judgment is required for fair values calculated using quoted market prices or observable market inputs for models. Greater subjectivity is required when making valuation adjustments for financial instruments in inactive markets or when using models where observable parameters do not exist. Also, the calculation of estimated fair value is based on market conditions at a specific point in time and may not be reflective of future fair values. For the Company's financial instruments carried at cost or amortized cost, the book value is not adjusted to reflect increases or decreases in fair value due to market fluctuations, including those due to interest rate changes, as it is the Company's intention to hold them until there is a recovery of fair value, which may be to maturity.

The Company employs a fair value hierarchy to categorize the inputs it uses in valuation techniques to measure the fair value. The following fair value hierarchy is used in selecting inputs, with the highest priority given to Level 1:

• Level 1 – Quoted prices for identical instruments in active markets.

• Level 2 – Quoted prices for similar instruments in active markets; quoted prices for identical or similar instruments in markets that are not active; and model-derived valuations in which all significant inputs are observable in active markets.

• Level 3 – Valuations derived from valuation techniques in which one or more significant inputs are not observable.

38

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

The Company classifies its investments in fixed maturities as available-for-sale and reports these investments at fair value. The Company's equity investments, limited liability investments, at fair value, real estate investments and subordinated debt are measured and reported at fair value.

Fixed maturities - Fair values of fixed maturities for which no active market exists are derived from quoted market prices of similar instruments or other third party evidence. All classes of the Company’s fixed maturities, primarily consisting of investments in US. Treasury bills and government bonds; obligations of states, municipalities and political subdivisions; mortgage-backed securities; and corporate securities, are classified as Level 2. Level 2 is applied to valuations based upon quoted prices for similar assets in active markets; quoted prices for identical or similar assets in markets that are inactive; or valuations based on models where the significant inputs are observable or can be corroborated by observable market data.

The Company engages a third-party vendor who utilizes third-party pricing sources and primarily employs a market approach to determine the fair values of our fixed maturities. The market approach includes primarily obtaining prices from independent third-party pricing services as well as, to a lesser extent, quotes from broker-dealers. Our third-party vendor also monitors market indicators, as well as industry and economic events, to ensure pricing is appropriate. All classes of our fixed maturities are valued using this technique. The Company has obtained an understanding of our third-party vendor’s valuation methodologies and inputs. Fair values obtained from our third-party vendor are not adjusted by the Company.

The following is a description of the significant inputs, by asset class, used by the third-party pricing services to determine the fair values of our fixed maturities included in Level 2:

• U.S. government, government agencies and authorities are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets and maturity.

• States, municipalities and political subdivisions are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, new issuances and credit spreads.

• Mortgage-backed securities are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, expected prepayments, expected credit default rates, delinquencies and issue specific information including, but not limited to, collateral type, seniority and vintage.

• Corporate securities are generally priced using the market approach using pricing vendors. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, issuer rating, benchmark yields, maturity and credit spreads.

Equity investments - Fair values of equity investments, including warrants, reflect quoted market values based on latest bid prices, where active markets exist, or models based on significant market observable inputs, where no active markets exist.

Limited liability investments, at fair value - Limited liability investments, at fair valueinclude the Company's investment in 1347 Investors as well as the underlying investments of Net Lease and Argo Holdings. 1347 Investors owns common stock in Limbach Holdings, Inc., a publicly traded company. Net Lease owns investments in limited liability companies that hold investment properties. Argo Holdings makes investments in limited liability companies and limited partnerships that hold investments in search funds and private operating companies.

• The fair value of the Company's investment in 1347 Investors is calculated based on a model that distributes the net equity of 1347 Investors to all classes of membership interests. The model uses quoted market prices and significant market observable inputs. This investment is categorized in Level 2 of the fair value hierarchy.

• The fair value of Net Lease's investments in limited liability companies is based upon the net asset values of the underlying investments companies as a practical expedient to estimate fair value. The Company applies the net asset value practical expedient to Net Lease's limited liability investments on an investment-by-investment basis unless it is probable that the Company will sell a portion of an investment at an amount different from the net asset value of the investment. Investments that are measured at fair value using the net asset value practical expedient are not required to be classified using the fair value hierarchy.

• The fair value of Argo Holdings' limited liability investments that hold investments in search funds is based on the initial investment in the search funds. The fair value of Argo Holdings' limited liability investments that hold investments in private operating companies is valued using a market approach including valuation multiples applied to corresponding

39

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

performance metrics, such as earnings before interest, tax, depreciation and amortization; revenue; or net earnings. The selected valuation multiples were estimated using multiples provided by the investees and review of those multiples in light of investor updates, performance reports, financial statements and other relevant information. These investments are categorized in Level 3 of the fair value hierarchy.

Real estate investments - The fair value of real estate investments involves a combination of the market and income valuation techniques. Under this approach, a market-based capitalization rate is derived from comparable transactions, adjusted for any unique characteristics of each asset, and applied to the asset under consideration. The cap rates used during underwriting and subsequent valuation incorporate the consideration of risks of vacancy and collection loss, administrative costs of owning net leased assets and possible capital expenditures that could be determined a landlord expense. These investments are categorized in Level 3 of the fair value hierarchy.

Subordinated debt - The fair value of the subordinated debt is calculated using a model based on significant market observable inputs and inputs developed by a third party. These inputs include credit spread assumptions developed by a third party and market observable swap rates. The subordinated debt is categorized in Level 2 of the fair value hierarchy.

Warrant liability- As described in Note 13, "Debt," the Company issued the KWH Warrants on March 1, 2019. The KWH Warrants are measured and reported at fair value and are included in accrued expenses and other liabilities in the consolidated balance sheets. The fair value of the warrant liability is estimated using an internal model without relevant observable market inputs. The significant inputs used in the model include an enterprise value multiple applied to earnings before interest, tax, depreciation and amortization. The implied enterprise value is reduced by the remaining debt associated with the KWH Loan to determine an implied equity value. The liability classified warrants are categorized in Level 3 of the fair value hierarchy.

40

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

Assets and Liabilities Measured at Fair Value on a Recurring Basis

The balances of the Company's financial assets and liabilities measured at fair value on a recurring basis by level within the fair value hierarchy as of June 30, 2019 and December 31, 2018 are as follows. Certain investments in limited liability companies that are measured at fair value using the net asset value practical expedient are not required to be classified using the fair value hierarchy, but are presented in the following tables to permit reconciliation of the fair value hierarchy to the amounts presented in the consolidated balance sheets:

(in thousands)					June 30, 2019
	Fair Value Measurements at the End of the Reporting Period Using
	Total		Quoted Prices in Active Markets for Identical Assets (Level 1)		Significant Other Observable Inputs (Level 2)		Significant Unobservable Inputs (Level 3)		Measured at Net Asset Value
Recurring fair value measurements:
Assets:
Fixed maturities:
U.S. government, government agencies and authorities	$	15,046	$	—	$	15,046	$	—	$	—
States, municipalities and political subdivisions	601		—		601		—		—
Mortgage-backed	2,454		—		2,454		—		—
Corporate	2,686		—		2,686		—		—
Total fixed maturities	20,787		—		20,787		—		—
Equity investments:
Common stock	179		179		—		—		—
Warrants	23		16		7		—		—
Total equity investments	202		195		7		—		—
Limited liability investments, at fair value	33,047		—		6,298		4,635		22,114
Real estate investments	10,662		—		—		10,662		—
Other investments	895		—		895		—		—
Short-term investments	154		—		154		—		—
Total assets	$	65,747	$	195	$	28,141	$	15,297	$	22,114
Liabilities:
Subordinated debt	$	50,224	$	—	$	50,224	$	—	$	—
Warrant liability	307		—		—		307		—
Total liabilities	$	50,531	$	—	$	50,224	$	307	$	—

41

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

(in thousands)					December 31, 2018
			Fair Value Measurements at the End of the Reporting Period Using
	Total		Quoted Prices in Active Markets for Identical Assets (Level 1)		Significant Other Observable Inputs (Level 2)		Significant Unobservable Inputs (Level 3)		Measured at Net Asset Value
Recurring fair value measurements:
Assets:
Fixed maturities:
U.S. government, government agencies and authorities	$	5,547	$	—	$	5,547	$	—	$	—
States municipalities and political subdivisions	607		—		607		—		—
Mortgage-backed	3,186		—		3,186		—		—
Corporate	2,920		—		2,920		—		—
Total fixed maturities	12,260		—		12,260		—		—
Equity investments:
Common stock	801		801		—		—		—
Warrants	55		19		36		—		—
Total equity investments	856		820		36		—		—
Limited liability investments, at fair value	26,015		—		206		4,124		21,685
Real estate investments	10,662		—		—		10,662		—
Other investments	2,079		—		2,079		—		—
Short-term investments	152		—		152		—		—
Total assets	$	52,024	$	820	$	14,733	$	14,786	$	21,685
Liabilities:
Subordinated debt	$	50,023	$	—	$	50,023	$	—	$	—
Total liabilities	$	50,023	$	—	$	50,023	$	—	$	—

42

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

The following table provides a reconciliation of the fair value of recurring Level 3 fair value measurements for the three and six months ended June 30, 2019 and June 30, 2018:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Assets:
Limited liability investments, at fair value:
Beginning balance	$	4,060		$	1,634		$	4,124		$	1,397
Purchases	599			504			674			978
Distributions received	(14		)	(70		)	(338		)	(562		)
Realized gains included in net (loss) income	14			—			83			251
Change in fair value of limited liability investments, at fair value included in net (loss) income	(24		)	15			92			19
Ending balance	$	4,635		$	2,083		$	4,635		$	2,083
Unrealized gains recognized in net (loss) income on limited liability investments, at fair value held at end of period	$	—		$	15		$	116		$	38
Real estate investments:
Beginning balance	$	10,662		$	10,662		$	10,662		$	10,662
Change in fair value of real estate investments included in net (loss) income	—			—			—			—
Ending balance	$	10,662		$	10,662		$	10,662		$	10,662
Unrealized gains recognized in net (loss) income on real estate investments held at end of period	$	—		$	—		$	—		$	—
Ending balance - assets	$	15,297		$	12,745		$	15,297		$	12,745
Liabilities:
Warrant liability:
Beginning balance	$	317		$	—		$	—		$	—
Issuance of warrants	—			—			361			—
Change in fair value of warrant liability included in net (loss) income	(10		)	—			(54		)	—
Ending balance - liabilities	$	307		$	—		$	307		$	—
Unrealized gains recognized in net (loss) income on warrant liability held at end of period	$	(10	)	$	—		$	(54	)	$	—

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's investments that are categorized as Level 3 at June 30, 2019 :

Categories	Fair Value		Valuation Techniques	Unobservable Inputs	Input Value(s)
Limited liability investments, at fair value	$	4,635	Market approach	Valuation multiples	5.0x-8.8x
Real estate investments	$	10,662	Market and income approach	Cap rates	7.5	%
Warrant liability	$	307	Market approach	Valuation multiple	6.0x

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's investments that are categorized as Level 3 at December 31, 2018:

Categories	Fair Value		Valuation Techniques	Unobservable Inputs	Input Value(s)
Limited liability investments, at fair value	$	4,124	Market approach	Valuation multiples	5.0x-8.8x
Real estate investments	$	10,662	Market and income approach	Cap rates	7.5	%

43

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

All transfers are recognized by the Company at the beginning of each reporting period. Transfers between Levels 2 and 3 generally relate to whether significant unobservable inputs are used for the fair value measurements. There were no transfers between levels in 2019 or 2018.

Investments Measured Using the Net Asset Value per Share Practical Expedient

The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at June 30, 2019:

Category	Fair Value (in thousands)		Unfunded Commitments	Redemption Frequency	Redemption Notice Period
Limited liability investments, at fair value	$	22,114	n/a	n/a	n/a

The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at December 31, 2018:

Category	Fair Value (in thousands)		Unfunded Commitments	Redemption Frequency	Redemption Notice Period
Limited liability investments, at fair value	$	21,685	n/a	n/a	n/a

Assets and Liabilities Measured at Fair Value on a Nonrecurring Basis

Certain assets and liabilities are measured at fair value on a nonrecurring basis, including assets that are adjusted for observable price changes or written down to fair value as a result of an impairment. For the three months ended June 30, 2019 and June 30, 2018, the Company recorded adjustments to increase the fair value of an certain investments in private companies for observable price changes of zero and $0.2 million, respectively, ($0.0 million and $0.2 million for the six months ended June 30, 2019 and June 30, 2018, respectively), which are included in net change in unrealized gain (loss) on private company investments in the consolidated statements of operations. The Company recorded no write-downs for other-than-temporary impairments related to investments in private companies for the three and six months ended June 30, 2019 and June 30, 2018. To determine the fair value of investments in these private companies, the Company considered rounds of financing and third-party transactions, discounted cash flow analyses and market-based information, including comparable transactions, trading multiples and changes in market outlook, among other factors. The Company has classified the fair value measurements of these investments in private companies as Level 3 because they involve significant unobservable inputs.

As further discussed in Note 5, "Acquisition and Discontinued Operations," the Company acquired Geminus on March 1, 2019. The fair values of intangible assets and deferred service fees associated with the acquisition of Geminus were determined to be Level 3 under the fair value hierarchy. The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for these Level 3 measurements:

44

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

Categories	Fair Value		Valuation Techniques	Unobservable Inputs	Input Value(s)
Customer relationships	$	3,732	Multi-period excess earnings	Growth rate	3.0	%
				Attrition rate	20.0	%
				Discount rate	13.0	%
Trade names	$	1,974	Relief from royalty	Royalty rate	0.25% - 2.0%
				Discount rate	13.0	%
Deferred service fees - Penn	$	8,734	Bottom-up	Normal profit margin	15.5	%
				Total direct costs	70.3	%
				Discount rate	5.0	%
Deferred service fees - Prime	$	1,830	Bottom-up	Normal profit margin	8.5	%
				Total direct costs	69.8	%
				Discount rate	5.0	%

NOTE 22 RELATED PARTIES

Related party transactions, including services provided to or received by the Company's subsidiaries, are measured in part by the amount of consideration paid or received as established and agreed by the parties. Except where disclosed elsewhere in these unaudited consolidated interim financial statements, the following is a summary of related party transactions.

(a)Argo Management Group, LLC

The Company acquired Argo Management Group, LLC ("Argo Management") in April 2016. Argo Management's primary business is to act as Managing Member of Argo Holdings. At June 30, 2019 and December 31, 2018, each of the Company, John T. Fitzgerald ("Fitzgerald"), the Company's Chief Executive Officer and President, and certain of Fitzgerald’s immediate family members owns equity interests in Argo Holdings, all of which interests were acquired prior to the Company’s acquisition of Argo Management. Subject to certain limitations, Argo Holdings' governing documents require all individuals and entities owning an equity interest in Argo Holdings to fund upon request his/her/its pro rata share of any funding requirements of Argo Holdings up to an aggregate maximum amount equal to his/her/its total capital commitment (each request for funds being referred to as a "Capital Call"). During 2018, the Company funded approximately $0.5 million in response to Capital Calls. During 2018, Fitzgerald and Fitzgerald’s immediate family members funded their respective Capital Calls. Argo Holdings used the proceeds of the Capital Calls to make investments, cover general operating expenses and pay the management fee owed to Argo Management. Argo Holdings made no Capital Calls during the six months ended June 30, 2019.

(b)1347 Property Insurance Holdings, Inc.

In November 2012, the Company formed Maison Insurance Company ("Maison"), a Louisiana domiciled property and casualty insurance company. In preparation for a transaction to take Maison public, the Company formed 1347 Property Insurance Holdings, Inc. (“PIH”). Maison was a wholly owned subsidiary of PIH, which completed an initial public offering effective March 31, 2014, pursuant to which the Company disposed of a majority interest in PIH. The Company owned zero and zero of the common shares of PIH at June 30, 2019 and December 31, 2018, respectively.

D. Kyle Cerminara ("Cerminara") was appointed to the PIH Board of Directors on December 27, 2016 and became Chairman of the Board of Directors of PIH on May 11, 2018. Since April 2012, Cerminara has also served as the Chief Executive Officer of Fundamental Global Investors, LLC ("FGI"). During 2018, FGI was a shareholder known by the Company to be a beneficial owner of more than 5% of the Company’s outstanding common shares. As of June 30, 2019, FGI is not known to be a shareholder or beneficial owner of more than 5% of the Company’s outstanding common shares. Larry G. Swets, Jr. ("Swets") has served as a member of the PIH Board of Directors since November 21, 2013 and served as the Chairman of the Board of Directors of PIH from March 5, 2017 to May 11, 2018. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018.

45

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

On February 11, 2014, the Company's subsidiary, 1347 Advisors, entered into a management services agreement with PIH which provides for certain services, including forecasting, analysis of capital structure and reinsurance programs, consultation in future restructuring or capital raising transactions, and consultation in corporate development initiatives, that 1347 Advisors will provide to PIH unless and until 1347 Advisors and PIH agree to terminate the services. On February 24, 2015, the Company announced that it had entered into a definitive agreement with PIH to terminate the management services agreement. Pursuant to the transaction, 1347 Advisors received the following consideration: $2.0 million in cash; $3.0 million of 8% preferred stock of PIH, mandatorily redeemable on February 24, 2020; a Performance Shares Grant Agreement with PIH, whereby 1347 Advisors will be entitled to receive 100,000 shares of PIH common stock if at any time the last sales price of PIH's common stock equals or exceeds $10.00 per share for any 20 trading days within any 30-trading day period; and warrants to purchase 1,500,000 shares of common stock of PIH with a strike price of $15.00, expiring on February 24, 2022.

On March 26, 2014, the Company entered into a Performance Share Grant Agreement with PIH, whereby the Company will be entitled to receive up to an aggregate of 375,000 shares of PIH common stock upon achievement of certain milestones for PIH’s stock price. Pursuant to the terms of the Performance Share Grant Agreement, if at any time the last sales price of PIH’s common stock equals or exceeds: (i) $12.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock; (ii) $15.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 125,000 shares of common stock earned pursuant to clause (i) herein); and (iii) $18.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 250,000 shares of common stock earned pursuant to clauses (i) and (ii) herein).

On January 2, 2018, the Company entered into an agreement with PIH to cancel the $10.00 per share Performance Share Grant Agreement in exchange for cash consideration of $0.3 million and to sell the $3.0 million of 8% preferred stock of PIH, mandatorily redeemable on February 24, 2020, for $3.0 million plus accrued but unpaid dividends. On July 24, 2018, the Company entered into an agreement with PIH to cancel the $12.00 per share, $15.00 per share and $18.00 per share Performance Share Grant Agreement in exchange for cash consideration of $1.0 million. No shares were received by the Company under either of the performance share grant agreements as of June 30, 2019.

(c)Itasca Capital Ltd.

Investment in investee includes the Company's investment in the common stock of ICL, a publicly traded Canadian corporation, and is accounted for under the equity method. The Company owned 22.9% and 22.9% of the common shares of ICL at June 30, 2019 and December 31, 2018, respectively.

Ballantyne Strong Inc. ("Ballantyne") owned 40.6% and 40.6% of the common shares of ICL at June 30, 2019 and December 31, 2018, respectively. Cerminara has served as the Chief Executive Officer of Ballantyne since November 2015 and as Chairman of the Board of Ballantyne since May 2015. Cerminara was appointed to the ICL Board of Directors on June 13, 2016 and became Chairman of the Board of Directors of ICL on June 4, 2018. Since April 2012, Cerminara has also served as the Chief Executive Officer of FGI. During 2018, FGI was a shareholder known by the Company to be a beneficial owner of more than 5% of the Company’s outstanding common shares. As of June 30, 2019, FGI is not known to be a shareholder or beneficial owner of more than 5% of the Company’s outstanding common shares. Swets has served as the ICL Chief Executive Officer and a member of the ICL Board of Directors since June 9, 2016. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. Fitzgerald has served as a member of the ICL Board of Directors since June 9, 2016. Fitzgerald joined the Company as an Executive Vice President in April 2016 following the Company’s acquisition of Argo. Fitzgerald has served as the Company’s Chief Executive Officer since September 5, 2018 and has served on the Company’s Board of Directors since April 21, 2016.

ICL and the Company executed a management service agreement effective June 10, 2016 pursuant to which the Company provided management services to ICL, including the non-exclusive use and services of appropriately qualified individuals to serve as ICL’s Chief Executive Officer and Chief Financial Officer, for an annual service fee of $0.0 million. This agreement was later amended on November 17, 2017 to provide an annual service fee of $0.0 million, beginning with full year 2017. The agreement was ultimately terminated effective January 31, 2019.

On October 9, 2019, the Company executed an agreement to sell 1,974,113 shares of ICL common stock, at a price of C$0.35 per share, to FGI for cash proceeds totaling C$0.7 million. On October 31, 2019, the Company executed an agreement to sell 3,011,447 shares of ICL common stock, at a price of C$0.35 per share, to Swets for consideration totaling C$1.1 million, comprised of cash

46

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

proceeds of C$0.2 million and 247,450 shares of the Company’s common stock. Both transactions closed during the fourth quarter of 2019. The 247,450 shares of the Company’s common stock were awarded to Swets pursuant to an Amended and Restated Restricted Stock Agreement (the "Swets Restricted Stock Agreement") executed on September 5, 2018 related to Swets’ departure from the Company. Pursuant to the Swets Restricted Stock Agreement, Swets retained 350,000 shares of restricted Company common stock that were to vest upon (i) the completion of the sale by 1347 Investors of its entire interest in the shares of Limbach common stock and (ii) the subsequent completion of the liquidation of 1347 Investors and the distribution of its assets to its members. Pursuant to a Distribution and Redemption Agreement, dated as of September 30, 2019, by and among 1347 Investors and its members, the Company received distributions of cash proceeds of $0.6 million, 594,750 shares of Limbach common stock and 400,000 warrants, exercisable at $15 and expiring July 20, 2023, on Limbach common shares, which the Company deemed as having satisfied the performance obligations described in the Swets Restricted Stock Agreement. Also, pursuant to the Swets Restricted Stock Agreement, Swets exercised his right to authorize the Company to withhold 102,550 shares of restricted Company common stock, which would otherwise have been delivered or available for vesting, in order to satisfy all federal, state, local or other taxes required to be withheld or paid in connection with such award, leaving Swets with 247,450 shares of the Company’s common stock.

(d)Fundamental Global Investors, LLC

During 2018, FGI was a shareholder known by the Company to be a beneficial owner of more than 5% of the Company’s outstanding common shares. As of June 30, 2019, FGI is not known to be a shareholder or beneficial owner of more than 5% of the Company’s outstanding common shares.

On October 25, 2017, the Company executed an agreement to sell 900,000 shares of PIH common stock, at a price of $7.85 per share, to FGI in two separate transactions for cash proceeds totaling $7.1 million. On November 1, 2017, the Company sold 475,428 of the 900,000 shares of PIH common stock to FGI for cash proceeds totaling $3.7 million. The second transaction, for the sale of the remaining 424,572 shares of PIH common stock for cash proceeds totaling $3.4 million, closed on March 15, 2018 following FGI having obtained the necessary regulatory approvals.

On July 30, 2018, the Company executed an agreement to sell its remaining 75,000 shares of PIH common stock, at a price of $7.13 per share, to FGI for cash proceeds totaling $0.5 million.

On July 30, 2018, the Company executed an agreement to sell 1,813,889 shares of ICL common stock, at a price of C$0.72 per share, to FGI for cash proceeds totaling C$1.3 million.

(e)Insurance Income Strategies Ltd.

IIS is a Bermuda corporation, formed in October 2017, organized to offer collateralized reinsurance in the property catastrophe market through its wholly owned operating subsidiary IIS Re Ltd. The Company held 100% of the outstanding common stock of IIS at June 30, 2019 and December 31, 2018. The Company did not invest any capital against the common shares and has not invested any capital in IIS via any other security of IIS. The Company also does not have any commitment to provide capital to IIS. See Note 7, "Variable Interest Entities," in the Company’s 2018 Annual Report for further discussion of IIS. Swets has served as the Chairman of the Board of Directors of IIS since its formation. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018.

Effective August 10, 2018, simultaneous with IIS issuing preferred stock to a third-party investor, the Company and IIS entered into a management service agreement, which describes the Company’s duties and rights to remuneration. The management service agreement describes the Company’s duties to include (a) identification and due diligence of potential transaction counterparties for consideration by IIS management; (b) advice on capital structure and corporate development opportunities; (c) support for compliance with the rules and regulations of the SEC; and (d) other periodic and special requests deemed within the scope of the management service agreement. The management service agreement provides for a fee 0.9% of the assets of IIS and 9% of the annual net profits.

Pursuant to other agreements executed August 10, 2018 simultaneous with IIS issuing preferred stock to a third-party investor, the Company (a) is obligated to share with the IIS third-party investor 50% of any future fees generated under the management service agreement and (b) waives its right to receive any fees until such time that the IIS third-party investor is either redeemed or exchanged into publicly traded equity shares of IIS, in either case for consideration not less than the IIS third-party investor’s original $15.0 million investment. As of December 31, 2018, neither of these scenarios had occurred, so the Company is not entitled to any fees under the management service agreement and has not recorded any such fees.

47

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

(f)Limited liability investments

The Company’s investments include investments in limited liability companies in which an officer or former officer of the Company is named as a Manager or is authorized to act on behalf of the Manager under the respective operating agreement.

Itasca Golf Investors, LLC:

Itasca Golf Investors, LLC ("IGI") was formed on April 8, 2014 for the general purpose of real estate investment. The members entered into an operating agreement under which the Company acquired a 42.9% membership interest in IGI. 1347 Capital LLC, a wholly owned subsidiary of the Company, was named the Manager of IGI in the operating agreement. Swets was authorized to act on behalf of the Manager. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. On September 5, 2018, the Company sold its investment in IGI to IGI Partners LLC for $1.5 million. Swets is a member of IGI Partners LLC.

AK Realty I LLC:

AK Realty I LLC ("AKR") was formed on September 21, 2015 for the purpose of becoming a member of AKA Opportunity Investments I LLC, a limited liability company formed for the purpose of investing, directly or indirectly, in real estate projects. The members of AKR entered into an operating agreement under which the Company acquired a 33.3% membership interest in AKR. Management of AKR is vested in a two-member Executive Committee. The Company designates one of the two members of the Executive Committee. Decisions of the Executive Committee require the unanimous approval of the members of the Executive Committee. The Company designated Swets as its representative on the Executive Committee. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018.

Logistics Leasing, LLC:

Logistics Leasing ("Logistics") was formed on July 26, 2017 for the purpose of acquiring and leasing small vehicles. The members of Logistics entered into an operating agreement under which the Company acquired a 50% membership interest in Logistics. The Company designates one of the two managers of Logistics. Major Decisions, as defined in the operating agreement, require the approval of members holding at least 51% of the membership interest. The Company designated Swets as a manager. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. During the first quarter of 2019, the Company impaired its investment in Logistics.

1347 Energy Holdings LLC:

1347 Energy Holdings LLC ("Energy") was formed on April 20, 2016 for the purpose of making investments in hydrocarbon assets as described in the operating agreement. At June 30, 2019 and December 31, 2018, the Company owned zero and 45.6% of the membership interests. The Company also held collateralized notes in principal amount of zero and $0.6 million at June 30, 2019 and December 31, 2018, respectively. Fitzgerald owned zero and 0.8% of the membership interests at June 30, 2019 and December 31, 2018, respectively. Energy was managed through a Board of Managers comprised of five managers, two of whom, Swets and Fitzgerald, were appointed by 1347 Capital LLC, a wholly owned subsidiary of the Company. With respect to any matter before the Board of Managers, the act of a majority of the managers constituting a quorum constituted the act of the Board. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. Fitzgerald joined the Company as an Executive Vice President in April 2016 following the Company’s acquisition of Argo. Fitzgerald has served as the Company’s Chief Executive Officer since September 5, 2018 and has served on the Company’s Board of Directors since April 21, 2016. During 2018, Energy entered into a purchase and sale agreement dated, February 12, 2018, for the sale of Energy to an unrelated third party, pursuant to which the Company’s $1.8 million collateralized loan to Energy and $0.7 million surety deposit were repaid in full and the Company’s equity investment, previously written down to zero under the equity method of accounting, was purchased. The transaction closed in a series of installments during the fourth quarter of 2018 and the first quarter of 2019.

1347 Investors LLC:

1347 Investors was formed on April 15, 2014 for the purpose of investing in and holding securities of 1347 Capital Corp., which subsequently merged with Limbach Holdings, Inc., a publicly traded company. The Company owned 26.7% of the membership units at June 30, 2019 and December 31, 2018. The Company's investment in 1347 Investors is accounted for at fair value and reported as limited liability investments, at fair value in the consolidated balance sheets, with any changes in fair value to be reported in gain (loss) on change in fair value of limited liability investment, at fair value in the consolidated statements of operations. The fair value of this investment is calculated based on a model that distributes the net equity of 1347 Investors to all classes of

48

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

membership interests. The model uses quoted market prices and significant market observable inputs. The most significant input to the model is the observed stock price of Limbach common stock.

ICL owned 47.6% of the membership units at June 30, 2019 and December 31, 2018. Ballantyne owned 40.6% and 40.6% of the common shares of ICL at June 30, 2019 and December 31, 2018, respectively.

Swets and Cerminara are the named managers of 1347 Investors. All acts of the managers must be unanimous. Cerminara has served as the Chief Executive Officer of Ballantyne since November 2015 and as Chairman of the Board of Ballantyne since May 2015. Cerminara was appointed to the ICL Board of Directors on June 13, 2016 and became Chairman of the Board of Directors of ICL on June 4, 2018. Since April 2012, Cerminara has also served as the Chief Executive Officer of FGI. During 2018, FGI was a shareholder known by the Company to be a beneficial owner of more than 5% of the Company’s outstanding common shares.

As of June 30, 2019, FGI is not known to be a shareholder or beneficial owner of more than 5% of the Company’s outstanding common shares. Swets has served as the ICL Chief Executive Officer and a member of the ICL Board of Directors since June 9, 2016. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. Fitzgerald has served as a member of the ICL Board of Directors since June 9, 2016. Fitzgerald joined the Company as an Executive Vice President in April 2016 following the Company’s acquisition of Argo. Fitzgerald has served as the Company’s Chief Executive Officer since September 5, 2018 and has served on the Company’s Board of Directors since April 21, 2016.

Pursuant to a Distribution and Redemption Agreement, dated as of September 30, 2019, by and among 1347 Investors and its members, the Company received distributions on November 19, 2019 of cash proceeds of $0.6 million, 594,750 shares of Limbach common stock and 400,000 warrants, exercisable at $15 and expiring July 20, 2023, on Limbach common shares. As a result of this distribution, the Company no longer owns membership units in 1347 Investors.

(g)Atlas Financial Holdings, Inc.

In November 2010, the Company issued promissory notes (the "Notes") to five employees (each a "Debtor" and collectively the "Debtors") for a total of $1.1 million, each Note bearing an interest rate of 3% (not compounding). The Debtors used the proceeds to purchase shares of common stock in Atlas Financial Holdings, Inc. ("Atlas"). Atlas was created via a triangular merger and spun-off from the Company in December 2010, at which time the Debtors became employees of Atlas and were no longer employees of the Company. The Notes required annual payments of interest on the anniversary date of the Notes, with the principal and any unpaid interest due in full on or before January 1, 2017, in the case of one of the Debtors, and November 1, 2017, in the case of the other four Debtors. Each Debtor was required to pledge to the Company the shares purchased utilizing the Notes proceeds, and such pledge was to be released once the note was paid in full. The current market value of the pledged shares is $0.0 million.

The Notes have been amended three times since their issuance, generally to extend payments of principal while also requiring progress payments that were not part of the original Notes. No principal has been waived, and interest continues to accrue on unpaid principal. The remaining principal amount outstanding on the Notes was $0.7 million as of June 30, 2019. The Company has concluded there are no indications the Debtors were experiencing financial difficulties at the time of the amendments, and the Company expects to collect all amounts due. The Debtors are current with the amended terms of the Notes. As a result, the Company has concluded the Notes are not impaired.

(h)Other related party transactions

On July 16, 2018, the Company entered into a definitive agreement to sell Mendota to Premier Holdings LLC. Steve Harrison, President of Mendota, is a minority investor in Premier Holdings LLC.

On September 5, 2018, the Company entered into a Senior Advisor Agreement with Swets, its former Chief Executive Officer. The Senior Advisor Agreement was for a one-year term with an annual consulting fee of $0.3 million. After September 5, 2019, Swets will continue to provide certain consulting services for an hourly fee on an as-needed basis.

On February 28, 2020, the Company entered into a Consulting Agreement (the "Consulting Agreement") with William A. Hickey, Jr. ("Hickey"), its former Chief Financial Officer, pursuant to which Hickey will provide consulting and transition support through at least April 30, 2020, subject to renewal thereafter by agreement of the parties. In accordance with the Consulting Agreement, Hickey will receive a consulting fee of $0.1 million for the months of March and April 2020 and an hourly consulting fee of $165 for time worked in subsequent months.

49

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

NOTE 23 COMMITMENTS AND CONTINGENCIES

(a)    Legal proceedings:

In April 2018, TRT LeaseCo, LLC ("TRT LeaseCo"), an indirect subsidiary of Kingsway, was named as a defendant in a lawsuit filed in the United States District Court for the Southern District of New York relating to CMC and its subsidiaries.  Kingsway indirectly owns 81% of CMC.  TRT LeaseCo (an indirect wholly owned subsidiary of CMC) entered into a Management Services Agreement (the "MSA") with DGI-BNSF Corp. ("DGI") (an affiliate of the entity that owns the remaining 19% of CMC) in July 2016 pursuant to which, among other things, DGI agreed to provide services to TRT LeaseCo in exchange for the fees specified in the MSA.  The complaint filed by DGI alleges that DGI is owed certain fees under the MSA that have not been paid.  If the case is decided against TRT LeaseCo, CMC and its subsidiaries (including TRT LeaseCo) would be unable to fulfill certain payment obligations to Kingsway under the transaction documents such that Kingsway may no longer be able to realize a material portion of the economic benefits originally anticipated to result from the CMC transaction, which could have a material adverse effect on Kingsway’s financial position, results of operations and cash flows.  Kingsway disagrees with DGI’s allegations and is vigorously defending these claims; however, there can be no assurance that Kingsway will ultimately prevail. The Company’s potential exposure under these agreements is not reasonably determinable, and no liability has been recorded in the audited consolidated financial statements at June 30, 2019.  No assurances can be given, however, that the Company will not be required to perform under these agreements in a manner that would have a material adverse effect on the Company’s financial position, results of operations and cash flow.

In May 2016, Aegis Security Insurance Company ("Aegis") filed a complaint for breach of contract and declaratory relief against the Company in the Eastern District of Pennsylvania alleging, among other things, that the Company breached a contractual obligation to indemnify Aegis for certain customs bond losses incurred by Aegis under the indemnity and hold harmless agreements provided by the Company to Aegis for certain customs bonds reinsured by Lincoln General Insurance Company ("Lincoln General") during the period of time that Lincoln General was a subsidiary of the Company.  Lincoln General was placed into liquidation in November 2015 and Aegis subsequently invoked its rights to indemnity under the indemnity and hold harmless agreements.  Effective January 20, 2020, Aegis and the Company entered into a Settlement Agreement with respect to such litigation pursuant to which the Company agreed to pay Aegis a one-time settlement amount of $0.9 million, which the Company will report in its consolidated statement of operations for the three months ended March 31, 2020, and to reimburse Aegis for 60% of future losses that Aegis may sustain in connection with such customs bonds, up to a maximum reimbursement amount of $4.8 million. The Company’s potential exposure under these agreements was not reasonably determinable at June 30, 2019, and no liability has been recorded in the audited consolidated financial statements at June 30, 2019.

(b)    Guarantee:

As further discussed in Note 5, "Acquisition and Discontinued Operations," as part of the transaction to sell Mendota, the Company will indemnify the buyer for loss and loss adjustment expenses with respect to open claims and certain specified claims in excess of Mendota's carried unpaid loss and loss adjustment expenses at June 30, 2018 related to the open claims and specified claims. The Company's potential exposure under these agreements was not reasonably determinable at June 30, 2019, and no liability has been recorded in the unaudited consolidated interim financial statements at June 30, 2019.

(c)    Commitments:

The Company has entered into subscription agreements to commit up to $2.6 million of capital to allow for participation in limited liability investments. At June 30, 2019, the unfunded commitment was $0.6 million, all of which related to the Company’s commitment to Argo Holdings. On December 4, 2019, Argo Management informed members of Argo Holdings that no more Capital Calls are planned.

NOTE 24 SUBSEQUENT EVENT

In March 2020, the outbreak of COVID-19 caused by a novel strain of the coronavirus was recognized as a pandemic by the World Health Organization, and the outbreak has become increasingly widespread in the United States, including in the markets in which we operate. The COVID-19 outbreak has had a notable impact on general economic conditions, including but not limited to the temporary closures of many businesses; "shelter in place" and other governmental regulations; and reduced consumer pending due to both job losses and other effects attributable to COVID-19. The near-term impacts of COVID-19 are primarily with respect

50

KINGSWAY FINANCIAL SERVICES INC.

Notes to Consolidated Financial Statements (Unaudited) June 30, 2019

to the Company’s Extended Warranty segment. As consumer spending has been impacted, including a decline in the purchase of new and used vehicles, and many businesses through which the Company distributes its products remain closed, the Company has seen cash flows being affected by a reduction in new warranty sales for vehicle service agreements. With respect to homeowner warranties, the Company expects to see a reduction in new enrollments in its home warranty programs associated with the impact of COVID-19 on new home sales in the United States. There remain many unknowns and the Company continues to monitor the expected trends and related demand for its services and has and will continue to adjust its operations accordingly.

The Company could experience other potential impacts as a result of COVID-19, including, but not limited to, potential impairment charges to the carrying amounts of goodwill, indefinite-lived intangibles and long-lived assets. Actual results may differ materially from the Company’s current estimates as the scope of COVID-19 evolves or if the duration of business disruptions is longer than initially anticipated.

51

KINGSWAY FINANCIAL SERVICES INC.

Item 2. Management's Discussion and Analysis of Financial Condition and Results of Operations

FORWARD-LOOKING STATEMENTS

Management's Discussion and Analysis includes “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934 that are not historical facts, and involve risks and uncertainties that could cause actual results to differ materially from those expected and projected. Words such as “expects,” “believes,” “anticipates,” “intends,” “estimates,” “seeks” and variations and similar words and expressions are intended to identify such forward-looking statements. Such forward-looking statements relate to future events or future performance, but reflect Kingsway management’s current beliefs, based on information currently available. A number of factors could cause actual events, performance or results to differ materially from the events, performance and results discussed in the forward-looking statements. For information identifying important factors that could cause actual results to differ materially from those anticipated in the forward-looking statements, see Kingsway’s securities filings, including its Annual Report on Form 10-K for the year ended December 31, 2018 ("2018 Annual Report"). The Company's securities filings can be accessed on the Canadian Securities Administrators’ website at www.sedar.com, on the EDGAR section of the U.S. Securities and Exchange Commission’s website at www.sec.gov or through the Company’s website at www.kingsway-financial.com. Except as expressly required by applicable securities law, the Company disclaims any intention or obligation to update or revise any forward-looking statements because of new information, future events or otherwise.

OVERVIEW

Kingsway is a Delaware holding company with operating subsidiaries located in the United States. The Company owns or controls subsidiaries primarily in the extended warranty, asset management and real estate industries. Kingsway conducts its business through the following two reportable segments: Extended Warranty and Leased Real Estate.

The Company previously conducted its business through a third reportable segment, Insurance Underwriting. Insurance Underwriting included the following subsidiaries of the Company: Mendota Insurance Company, Mendakota Insurance Company, Mendakota Casualty Company, Kingsway Amigo Insurance Company ("Amigo") and Kingsway Reinsurance Corporation ("Kingsway Re"). Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company are referred to collectively herein as "Mendota." On July 16, 2018, the Company announced that it had entered into a definitive agreement to sell Mendota. On October 18, 2018, the Company announced that the sale was completed. As a result, Mendota has been classified as discontinued operations and the results of their operations are reported separately for all periods presented. As a consequence of classifying Mendota as discontinued operations, the remaining composition of the Insurance Underwriting segment no longer meets the criteria of a reportable segment. As such, all segmented information has been restated to exclude the Insurance Underwriting segment for all periods presented. The operating results of Amigo and Kingsway Re, previously included in the Insurance Underwriting segment, are now included in Other income and expenses not allocated to segments, net.

Extended Warranty includes the following subsidiaries of the Company: IWS Acquisition Corporation ("IWS"), Trinity Warranty Solutions LLC ("Trinity"), Professional Warranty Service Corporation ("PWSC") and Geminus Holding Company, Inc. ("Geminus"). Throughout Management's Discussion and Analysis, the term "Extended Warranty" is used to refer to this segment.

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by credit unions in 23 states and the District of Columbia to their members.

Trinity sells heating, ventilation, air conditioning ("HVAC"), standby generator, commercial LED lighting and refrigeration warranty products and provides equipment breakdown and maintenance support services to companies across the United States. As a seller of warranty products, Trinity markets and administers product warranty contracts for certain new and used products in the HVAC, standby generator, commercial LED lighting and refrigeration industries throughout the United States. Trinity acts as an agent on behalf of the third-party insurance companies that underwrite and guaranty these warranty contracts. Trinity does not guaranty the performance underlying the warranty contracts it sells. As a provider of equipment breakdown and maintenance support services, Trinity acts as a single point of contact to its clients for both certain equipment breakdowns and scheduled maintenance of equipment. Trinity will provide such repair and breakdown services by contracting with certain HVAC providers.

PWSC sells new home warranty products and provides administration services to home builders and homeowners across the United States. PWSC distributes its products and services through an in house sales team and through insurance brokers and insurance carriers throughout all states except Alaska and Louisiana.

Geminus sells vehicle service agreements and other finance and service products to used car buyers across the United States. Penn and Prime distribute these products via independent used car dealerships and franchised car dealerships, respectively.

52

KINGSWAY FINANCIAL SERVICES INC.

Leased Real Estate includes the Company's subsidiary, CMC Industries, Inc. ("CMC"). CMC owns, through an indirect wholly owned subsidiary (the "Property Owner"), a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property"), which is subject to a long-term triple net lease agreement. The Real Property is also subject to a mortgage, which is recorded as note payable in the consolidated balance sheets (the "Mortgage"). Throughout Management's Discussion and Analysis, the term "Leased Real Estate" is used to refer to this segment.

Impact of COVID-19

In March 2020, the outbreak of COVID-19 caused by a novel strain of the coronavirus was recognized as a pandemic by the World Health Organization, and the outbreak has become increasingly widespread in the United States, including in the markets in which we operate. The COVID-19 outbreak has had a notable impact on general economic conditions, including but not limited to the temporary closures of many businesses; “shelter in place” and other governmental regulations; and reduced consumer spending due to both job losses and other effects attributable to COVID-19. There remain many unknowns.

The near-term impacts of COVID-19 are primarily with respect to our Extended Warranty segment. As consumer spending has been impacted, including a decline in the purchase of new and used vehicles, and many businesses through which we distribute our products remain closed, we have seen cash flows being affected by a reduction in new warranty sales for vehicle service agreements. With respect to homeowner warranties, we expect to see a reduction in new enrollments in our home warranty programs associated with the impact of COVID-19 on new home sales in the United States. 

On March 27, 2020, the President of the United States signed the Coronavirus Aid, Relief, and Economic Security ("CARES") Act, a substantial tax-and-spending package intended to provide additional economic stimulus to address the impact of the COVID-19 pandemic. We continue to monitor the impact of the COVID-19 outbreak closely, as well as any effects that may result from the CARES Act. However, the extent to which the COVID-19 outbreak will impact our operations or financial results is uncertain.

NON-U.S. GAAP FINANCIAL MEASURE

Throughout this quarterly report, we present our operations in the way we believe will be most meaningful, useful and transparent to anyone using this financial information to evaluate our performance. Our unaudited consolidated interim financial statements have been prepared in accordance with accounting principles generally accepted in the United States of America ("U.S. GAAP") for interim financial information. In addition to the U.S. GAAP presentation of net loss, we present segment operating income as a non-U.S. GAAP financial measure, which we believe is valuable in managing our business and drawing comparisons to our peers. Below is a definition of our non-U.S. GAAP measure and its relationship to U.S. GAAP.

Segment Operating Income

Segment operating income represents one measure of the pretax profitability of our segments and is derived by subtracting direct segment expenses from direct segment revenues. Revenues and expenses are presented in the unaudited consolidated statements of operations, but are not subtotaled by segment; however, this information is available in total and by segment in Note 20, "Segmented Information," to the unaudited consolidated interim financial statements, regarding reportable segment information. The nearest comparable U.S. GAAP measure is (loss) income from continuing operations before income tax expense (benefit) that, in addition to segment operating income, includes net investment income, net realized (losses) gains, (loss) gain on change in fair value of equity investments, gain (loss) on change in fair value of limited liability investments, at fair value, net change in unrealized gain (loss) on private company investments, other-than-temporary impairment loss, interest expense not allocated to segments, other income and expenses not allocated to segments, net, amortization of intangible assets, gain (loss) on change in fair value of debt, gain on disposal of subsidiary and equity in net income (loss) of investee. A reconciliation of segment operating income to (loss) income from continuing operations before income tax expense (benefit) for the three and six months ended June 30, 2019 and June 30, 2018 is presented in Table 1 of the "Results of Continuing Operations" section of Management's Discussion and Analysis.

53

KINGSWAY FINANCIAL SERVICES INC.

CRITICAL ACCOUNTING ESTIMATES AND ASSUMPTIONS

The preparation of unaudited consolidated interim financial statements in conformity with U.S. GAAP requires management to make estimates and assumptions that affect the reported amounts and classifications of assets and liabilities, revenues and expenses, and the related disclosures of contingent assets and liabilities in the consolidated financial statements and accompanying notes. Actual results could differ from these estimates. Estimates and their underlying assumptions are reviewed on an ongoing basis. Changes in estimates are recorded in the accounting period in which they are determined. The critical accounting estimates and assumptions in the accompanying unaudited consolidated interim financial statements include the provision for unpaid loss and loss adjustment expenses; valuation of fixed maturities and equity investments; impairment assessment of investments; valuation of limited liability investments, at fair value; valuation of real estate investments; valuation of deferred income taxes; valuation of mandatorily redeemable preferred stock; valuation and impairment assessment of intangible assets; goodwill recoverability; deferred acquisition costs; fair value assumptions for subordinated debt obligations; and revenue recognition.

The Company’s critical accounting estimates and assumptions are described in Management's Discussion and Analysis of Financial Condition and Results of Operations included in the 2018 Annual Report. There has been no material change subsequent to December 31, 2018 to the information previously disclosed in the 2018 Annual Report with respect to these critical accounting estimates and assumptions.

RESULTS OF CONTINUING OPERATIONS

A reconciliation of total segment operating income to net (loss) income for the three and six months ended June 30, 2019 and June 30, 2018 is presented in Table 1 below:

Table 1 Segment Operating Income

(in thousands of dollars)

	For the three months ended June 30,									For the six months ended June 30,
	2019			2018			Change			2019			2018			Change
Segment operating income:
Extended Warranty	$	1,035		$	1,090		$	(55	)	$	1,602		$	1,936		$	(334	)
Leased Real Estate	753			618			135			1,205			1,492			(287		)
Total segment operating income	1,788			1,708			80			2,807			3,428			(621		)
Net investment income	749			1,010			(261		)	1,448			1,648			(200		)
Net realized (losses) gains	(556		)	132			(688		)	(241		)	397			(638		)
(Loss) gain on change in fair value of equity investments	(63		)	(421		)	358			15			744			(729		)
Gain (loss) on change in fair value of limited liability investments, at fair value	2,347			(525		)	2,872			6,612			(1,461		)	8,073
Net change in unrealized gain (loss) on private company investments	—			(155		)	155			19			(155		)	174
Other-than-temporary impairment loss	—			—			—			(75		)	—			(75		)
Interest expense not allocated to segments	(2,339		)	(1,844		)	(495		)	(4,441		)	(3,561		)	(880		)
Other income and expenses not allocated to segments, net	(2,597		)	(3,213		)	616			(4,361		)	(5,625		)	1,264
Amortization of intangible assets	(676		)	(254		)	(422		)	(1,197		)	(509		)	(688		)
Gain (loss) on change in fair value of debt	918			(142		)	1,060			1,494			(1,061		)	2,555
Gain on disposal of subsidiary	—			17			(17		)	—			17			(17		)
Equity in net income (loss) of investee	201			(385		)	586			168			(284		)	452
(Loss) income from continuing operations before income tax expense (benefit)	(228		)	(4,072		)	3,844			2,248			(6,422		)	8,670
Income tax expense (benefit)	168			190			(22		)	(545		)	444			(989		)
(Loss) income from continuing operations	(396		)	(4,262		)	3,866			2,793			(6,866		)	9,659
Income from discontinued operations, net of taxes	—			594			(594		)	—			980			(980		)
Loss on disposal of discontinued operations, net of taxes	—			(6,628		)	6,628			—			(6,628		)	6,628
Net (loss) income	$	(396	)	$	(10,296	)	$	9,900		$	2,793		$	(12,514	)	$	15,307

54

KINGSWAY FINANCIAL SERVICES INC.

(Loss) Income from Continuing Operations and Net (Loss) Income

In the second quarter of 2019, we reported loss from continuing operations of $0.4 million compared to $4.3 million in the second quarter of 2018. For the six months ended June 30, 2019, we reported income from continuing operations of $2.8 million compared to a loss from continuing operations of $6.9 million for the six months ended June 30, 2018. The loss from continuing operations for the three months ended June 30, 2019 is primarily due to operating income in Extended Warranty and Leased Real Estate and gain on change in fair value of limited liability investments, at fair value partially offset by interest expense not allocated to segments and other income and expenses not allocated to segments, net. The income from continuing operations for the six months ended June 30, 2019 is primarily due to operating income in Extended Warranty and Leased Real Estate, net investment income and gain on change in fair value of limited liability investments, at fair value partially offset by interest expense not allocated to segments and other income and expenses not allocated to segments, net. The loss from continuing operations for the three months ended June 30, 2018 is primarily due to interest expense not allocated to segments and other income and expenses not allocated to segments, net, partially offset by Extended Warranty segment operating income. The loss from continuing operations for the six months ended June 30, 2018 is primarily due to interest expense not allocated to segments, other income and expenses not allocated to segments, net, loss on change in fair value of limited liability investments, at fair value and loss on change in fair value of debt, partially offset by operating income in Extended Warranty and Leased Real Estate and net investment income.

For the three months ended June 30, 2019, we reported net loss of $0.4 million compared to $10.3 million for the three months ended June 30, 2018. For the six months ended June 30, 2019, we reported net income of $2.8 million compared to a net loss of $12.5 million for the six months ended June 30, 2018.

Extended Warranty

The Extended Warranty service fee and commission income increased 32.6% to $11.8 million for the three months ended June 30, 2019 compared with $8.9 million for the three months ended June 30, 2018 ($21.6 million year to date compared to $18.5 million prior year to date, representing a 16.8%increase). The increase in service fee and commission income is primarily reflective of the inclusion of Geminus in 2019 following its acquisition effective March 1, 2019. Geminus service fee and commission income was $2.8 million and zero for the three months ended June 30, 2019 and June 30, 2018, respectively, ($3.7 million and zero for the six months ended June 30, 2019 and June 30, 2018, respectively). The Extended Warranty service fee and commission income for the six months ended June 30, 2019 also reflects decreases at Trinity and PWSC partially offset by an increase at IWS compared to the six months ended June 30, 2018.

The Extended Warranty operating income was $1.0 million for the three months ended June 30, 2019 compared with $1.1 million for the three months ended June 30, 2018 ($1.6 million year to date compared to $1.9 million prior to date). Operating income for the three and six months ended June 30, 2019 includes Geminus operating income of $0.2 million and $0.1 million, respectively, which offset lower operating income at PWSC and IWS for the three months and six months ended June 30, 2019.

Leased Real Estate

In the second quarter of 2019, Leased Real Estate rental income was $3.3 million compared to $3.3 million in the second quarter of 2018 ($6.7 million year to date compared to $6.7 million prior year to date). The rental income is derived from CMC's long-term triple net lease. The Leased Real Estate operating income was $0.8 million for the three months ended June 30, 2019 compared with $0.6 million for the three months ended June 30, 2018 ($1.2 million year to date compared to $1.5 million prior year to date). The increase in operating income for the three months ended June 30, 2019 is primarily attributable to lower litigation expenses during the three months ended June 30, 2019 compared to the same period in 2018. The decrease in operating income for the six months ended June 30, 2019 is primarily attributable to higher litigation expenses during the six months ended June 30, 2019 compared to the same period in 2018. See Note 23, "Commitments and Contingencies," to the unaudited consolidated interim financial statements for further details. Leased Real Estate operating income includes interest expense of $1.5 million and $1.5 million for the three months ended June 30, 2019 and June 30, 2018, respectively ($3.0 million and $3.1 million, respectively, year to date and prior year to date). See "Investments" section below for further discussion.

Net Investment Income

Net investment income was $0.7 million in the second quarter of 2019 compared to $1.0 million in the second quarter of 2018 ($1.4 million year to date compared to $1.6 million prior year to date). The decrease in net investment income for the three and six months ended June 30, 2019 primarily relates to lower net investment income recorded from the Company’s limited liability investments, at fair value.

55

KINGSWAY FINANCIAL SERVICES INC.

Net Realized (Losses) Gains

Net realized losses were $0.6 million in the second quarter of 2019 compared to net realized gains of $0.1 million in the second quarter of 2018 (net realized losses of $0.2 million year to date compared to net realized gains of $0.4 million prior year to date). The increase in net realized losses for the three and six months ended June 30, 2019 compared to net realized gains for the three and six months ended June 30, 2018 resulted primarily from a $0.6 million net realized loss recorded during the second quarter of 2019 related to the sale of one of the Company’s limited liability investments.

(Loss) Gain on Change in Fair Value of Equity Investments

Loss on change in fair value of equity investments was $0.1 million in the second quarter of 2019 compared to $0.4 million in the second quarter of 2018 (gain of $0.0 million year to date compared to gain of $0.7 million prior year to date). The loss on change in fair value of equity investments includes realized losses of $0.1 million and $0.0 million on equity investments sold during the three months ended June 30, 2019 and June 30, 2018, respectively (realized losses of $0.1 million year to date compared to realized gains of $0.5 million prior year to date) and unrealized gains of $0.0 million and unrealized losses of $0.4 million on equity investments held during the three months ended June 30, 2019 and June 30, 2018, respectively (unrealized gains of $0.1 million and $0.2 million, respectively, year to date and prior year to date).

Gain (Loss) on Change in Fair Value of Limited Liability Investments, at Fair Value

Gain (loss) on change in fair value of limited liability investments, at fair value was a gain of $2.3 million in the second quarter of 2019 compared to a loss of $0.5 million in the second quarter of 2018 (gain of $6.6 million year to date compared to a loss of $1.5 million prior year to date). The increase is primarily due to a $1.9 million increase in fair value of 1347 Investors recorded for the three months ended June 30, 2019 compared to a $0.4 million decrease in fair value of 1347 Investors recorded for the three months ended June 30, 2018 (increase in fair value of $6.1 million year to date compared to decrease in fair value of $1.8 million prior year to date). The fair value of the Company's investment in 1347 Investors is calculated based on a model that distributes the net equity of 1347 Investors to all classes of membership interests. The model uses quoted market prices and significant market observable inputs. The most significant input to the model is the observed stock price of Limbach Holdings, Inc. ("Limbach") common stock. During the fourth quarter of 2019, the Company’s investment in 1347 Investors was dissolved, which resulted in the Company holding shares of Limbach common stock directly.  During the second half of 2019 through the first quarter of 2020, the Limbach common stock price has declined, which has resulted in a lower valuation of 1347 Investors through the date of dissolution, as well as a decrease in the value of the Limbach common stock held directly. 

Net Change in Unrealized Gain (Loss) on Private Company Investments

Net change in unrealized gain (loss) on private company investments was zero in the second quarter of 2019 compared to a loss of $0.2 million in the second quarter of 2018 (gain of $0.0 million year to date compared to loss of $0.2 million prior year to date). For the three and six months ended June 30, 2018, the Company recorded adjustments of $0.2 million and $0.2 million, respectively, to decrease the fair value of certain investments in private companies for observable price changes.

Other-Than-Temporary Impairment Loss

As a result of the analysis performed by the Company to determine declines in market value that are other-than-temporary, the Company recorded write-downs of zero and zero for other-than-temporary impairment related to limited liability investments for the three months ended June 30, 2019 and June 30, 2018, respectively ($0.1 million year to date compared to zero prior year to date).

Interest Expense not Allocated to Segments

Interest expense not allocated to segments for the second quarter of 2019 was $2.3 million compared to $1.8 million in the second quarter of 2018 ($4.4 million year to date compared to $3.6 million prior year to date). The increase for the three and six months ended June 30, 2019 is primarily attributable to generally higher London interbank offered interest rates for three-month U.S. dollar deposits ("LIBOR") during the three and six months ended June 30, 2019 compared to the same periods in 2018. The Company's subordinated debt bears interest at the rate of LIBOR, plus spreads ranging from 3.85% to 4.20%. Interest expense during the three and six months ended June 30, 2019 also includes $0.3 million and $0.5 million, respectively, related to the Company’s acquisition of Geminus. See Note 5, "Acquisition and Discontinued Operations," to the unaudited consolidated interim financial statements for further details.

56

KINGSWAY FINANCIAL SERVICES INC.

Other Income and Expenses not Allocated to Segments, Net

Other income and expenses not allocated to segments, net was a net expense of $2.6 million in the second quarter of 2019 compared to a net expense of $3.2 million in the second quarter of 2018 ($4.4 million year to date compared to $5.6 million prior year to date). Included in other income and expenses not allocated to segments are expenses of $0.8 million and $1.3 million for Amigo for the three months ended June 30, 2019 and June 30, 2018, respectively ($0.7 million year to date compared to $1.7 million prior year to date). Amigo was previously included in the Insurance Underwriting segment along with Mendota, Mendakota and MCC. As a consequence of classifying Mendota, Mendakota and MCC as discontinued operations, the remaining composition of the Insurance Underwriting segment no longer meets the criteria of a reportable segment. As such, all segmented information has been restated to exclude the Insurance Underwriting segment for all periods presented. The operating results of Amigo previously included in the Insurance Underwriting segment are now included in Other income and expenses not allocated to segments, net.

Amortization of Intangible Assets

The Company's intangible assets with definite useful lives are amortized over their estimated useful lives. Amortization of intangible assets was $0.7 million in the second quarter of 2019 compared to $0.3 million in the second quarter of 2018 ($1.2 million year to date compared to $0.5 million prior year to date). The higher amortization expense for the three and six months ended June 30, 2019 is primarily related to amortization recorded in conjunction with the Company's acquisitions of PWSC on October 12, 2017 and Geminus on March 1, 2019. During the third quarter of 2018, the Company completed its fair value analysis of the PWSC assets acquired and liabilities assumed. As a result, the Company recorded amortization expense of $0.2 million and zero for the three months ended June 30, 2019 and June 30, 2018, respectively ($0.4 million and zero for the six months ended June 30, 2019 and June 30, 2018, respectively). Amortization of intangible assets during the three and six months ended June 30, 2019 also includes $0.2 million and $0.3 million, respectively, related to the Company’s acquisition of Geminus. See Note 5, "Acquisition and Discontinued Operations," to the unaudited consolidated interim financial statements for further details on the Company’s acquisition of Geminus.

Gain (Loss) on Change in Fair Value of Debt

Gain (loss) on change in fair value of debt amounted to a gain of $0.9 million in the second quarter of 2019 compared to a loss of $0.1 million in the second quarter of 2018 (gain of $1.5 million year to date compared to a loss of $1.1 million prior year to date). The gain for the three and six months ended June 30, 2019 reflects a decrease in the fair value of the subordinated debt resulting from changes in inputs, other than the instrument-specific credit risk, to the Company’s fair value model. The loss for the three and six months ended June 30, 2018 reflects an increase in the fair value of the subordinated debt resulting from changes in inputs, other than the instrument-specific credit risk, to the Company’s fair value model. As further discussed in Note 4, "Recently Issued Accounting Standards," to the unaudited consolidated interim financial statements, effective January 1, 2018, the Company adopted ASU 2016-01. As a result, the portion of the change in fair value of subordinated debt related to the instrument-specific credit risk is now recognized in other comprehensive income (loss). See "Debt" section below for further information.

Equity in Net Income (Loss) of Investee

Equity in net income of investee for the second quarter of 2019 was $0.2 million compared to loss of $0.4 million in the second quarter of 2018 (income of $0.2 million year to date compared to a loss of $0.3 million prior year to date). Equity in net income (loss) of investee represents the Company's investment in Itasca Capital Ltd. See Note 7, "Investment in Investee," to the unaudited consolidated interim financial statements, for further discussion.

Income Tax Expense (Benefit)

Income tax expense for the second quarter of 2019 was $0.2 million compared to $0.2 million in the second quarter of 2018 (benefit of $0.5 million year to date compared to expense of $0.4 million prior year to date). See Note 16, "Income Taxes," to the unaudited consolidated interim financial statements, for additional detail of the income tax expense (benefit) recorded for the three and six months ended June 30, 2019 and June 30, 2018.

INVESTMENTS

Portfolio Composition

All of our investments in fixed maturities are classified as available-for-sale and are reported at fair value. All of our equity investments are reported at fair value. All of our limited liability investments are accounted for under the equity method of accounting. The most recently available financial statements of the limited liability investments are used in applying the equity method. The difference between the end of the reporting period of the limited liability investments and that of the Company is

57

KINGSWAY FINANCIAL SERVICES INC.

no more than three months. Limited liability investments, at fair value represent the Company's investment in 1347 Investors LLC as well as the underlying investments of the Company’s consolidated entities Net Lease and Argo Holdings. Investments in private companies consist of convertible preferred stocks and notes in privately owned companies and investments in limited liability companies in which the Company’s interests are deemed minor. These investments do not have readily determinable fair values and, therefore, are reported at cost, adjusted for observable price changes and impairments. Real estate investments are reported at fair value. Other investments include collateral loans and are reported at their unpaid principal balance. Short-term investments, which consist of investments with original maturities between three months and one year, are reported at cost, which approximates fair value.

At June 30, 2019, we held cash and cash equivalents, restricted cash and investments with a carrying value of $100.5 million.

Investments held by our insurance subsidiary, Amigo, must comply with domiciliary state regulations that prescribe the type, quality and concentration of investments. Our U.S. operations typically invest in U.S. dollar-denominated instruments to mitigate their exposure to currency rate fluctuations.

Table 2 below summarizes the carrying value of investments, including cash and cash equivalents and restricted cash, at the dates indicated.

TABLE 2 Carrying value of investments, including cash and cash equivalents and restricted cash

(in thousands of dollars, except for percentages)

Type of investment	June 30, 2019	% of Total		December 31, 2018	% of Total
Fixed maturities:
U.S. government, government agencies and authorities	15,046	15.0	%	5,547	6.1	%
States, municipalities and political subdivisions	601	0.6	%	607	0.6	%
Mortgage-backed	2,454	2.4	%	3,186	3.5	%
Corporate	2,686	2.7	%	2,920	3.2	%
Total fixed maturities	20,787	20.7	%	12,260	13.4	%
Equity investments:
Common stock	179	0.2	%	801	0.9	%
Warrants	23	—	%	55	—	%
Total equity investments	202	0.2	%	856	0.9	%
Limited liability investments	3,891	3.9	%	4,790	5.2	%
Limited liability investments, at fair value	33,047	32.9	%	26,015	28.4	%
Investments in private companies	2,661	2.6	%	3,090	3.4	%
Real estate investments	10,662	10.6	%	10,662	11.7	%
Other investments	895	0.9	%	2,079	2.3	%
Short-term investments	154	0.2	%	152	0.2	%
Total investments	72,299	72.0	%	59,904	65.5	%
Cash and cash equivalents	10,899	10.8	%	14,619	16.0	%
Restricted cash	17,320	17.2	%	16,959	18.5	%
Total	100,518	100.0	%	91,482	100.0	%

Other-Than-Temporary Impairment

The Company performs a quarterly analysis of its investments classified as available-for-sale to determine if declines in market value are other-than-temporary. Further information regarding our detailed analysis and factors considered in establishing an other-than-temporary impairment on an investment is discussed within Note 6, "Investments," to the unaudited consolidated interim financial statements. 

As a result of the analysis performed by the Company to determine declines in market value that are other-than-temporary, the Company recorded no write-downs for other-than-temporary impairment related to limited liability investments for the three months ended June 30, 2019 and June 30, 2018, respectively ($0.1 million year to date compared to zero prior year to date). As a result of the analysis performed with respect to limited liability investments, at fair value, the Company recorded impairments of $0.0 million and zero for the three months ended June 30, 2019 and June 30, 2018, respectively, ($0.0 million and $0.0 million for the six months ended June 30, 2019 and June 30, 2018, respectively), which are included in gain (loss) on change in fair value

58

KINGSWAY FINANCIAL SERVICES INC.

of limited liability investments, at fair value in the consolidated statements of operations. There were no write-downs recorded for other-than-temporary impairments related to available-for sale investments and investments in private companies for the three and six months ended June 30, 2019 and June 30, 2018, respectively.

The length of time a fixed maturity investment may be held in an unrealized loss position may vary based on the opinion of the investment manager and their respective analyses related to valuation and to the various credit risks that may prevent us from recapturing the principal investment. In the case of a fixed maturity investment where the investment manager determines that there is little or no risk of default prior to the maturity of a holding, we would elect to hold the investment in an unrealized loss position until the price recovers or the investment matures. In situations where facts emerge that might increase the risk associated with recapture of principal, the Company may elect to sell a fixed maturity investment at a loss.

At June 30, 2019 and December 31, 2018, the gross unrealized losses for fixed maturities amounted to $0.0 million and $0.2 million, respectively, and there were no unrealized losses attributable to non-investment grade fixed maturities. At each of June 30, 2019 and December 31, 2018, all unrealized losses on individual investments were considered temporary.

Impact of COVID-19 on Investments

As discussed in Note 24, "Subsequent Event" to the unaudited consolidated interim financial statements, in March 2020 the outbreak of COVID-19 caused by a novel strain of the coronavirus was recognized as a pandemic by the World Health Organization, and the outbreak has become increasingly widespread in the United States, including in the markets in which we operate. The COVID-19 outbreak has had a notable impact on general economic conditions, including but not limited to the temporary closures of many businesses; "shelter in place" and other governmental regulations; and reduced consumer spending due to both job losses and other effects attributable to COVID-19. There remain many unknowns.

As part of the Company’s March 31, 2020 quarterly impairment analysis of its investments in private companies, the Company determined that it should write-down one of its investments by 90%, or $0.7 million, for other-than-temporary impairments as a result of the impacts of COVID-19 on the investment's underlying business. The Company continues to assess the impact that the COVID-19 pandemic may have on the value of its various investments, which could result in future material decreases in the underlying investment value. Such decreases may be considered temporary or could be deemed to be other-than-temporary and management may be required to record write-downs of the related investments in future reporting periods.

UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES

Unpaid loss and loss adjustment expenses represent the estimated liabilities for reported loss events, incurred but not reported ("IBNR") loss events and the related estimated loss adjustment expenses.

Tables 5 and 6 present distributions, by line of business, of the provision for unpaid loss and loss adjustment expenses gross and net of external reinsurance, respectively.

TABLE 5 Provision for unpaid loss and loss adjustment expenses - gross

(in thousands of dollars)

Line of Business	June 30, 2019	December 31, 2018
Non-standard automobile	516	686
Commercial automobile	184	794
Other	1,237	593
Total	1,937	2,073

59

KINGSWAY FINANCIAL SERVICES INC.

TABLE 6 Provision for unpaid loss and loss adjustment expenses - net of reinsurance recoverable

(in thousands of dollars)

Line of Business	June 30, 2019	December 31, 2018
Non-standard automobile	516	686
Commercial automobile	184	794
Other	1,237	593
Total	1,937	2,073

Non-Standard Automobile

At June 30, 2019 and December 31, 2018, the gross provisions for unpaid loss and loss adjustment expenses for our non-standard automobile business were $0.5 million and $0.7 million, respectively. The decrease is due to payments of loss and loss adjustment expenses at Amigo.

Commercial Automobile

At June 30, 2019 and December 31, 2018, the gross provisions for unpaid loss and loss adjustment expenses for our commercial automobile business were $0.2 million and $0.8 million, respectively. The decrease is due to payments of loss and loss adjustment expenses at Amigo.

Other

At June 30, 2019 and December 31, 2018, the gross provisions for unpaid loss and loss adjustment expenses for our other business were $1.2 million and $0.6 million, respectively. The increase is due to an increase in unpaid loss and loss adjustment expenses at Amigo, partially offset by a decrease in unpaid loss and loss adjustment expenses at Kingsway Re.

Information with respect to development of our provision for prior years' loss and loss adjustment expenses is presented in Table 7.

TABLE 7 Increase in prior years' provision for loss and loss adjustment expenses

(in thousands of dollars)

	Three months ended June 30,		Six months ended June 30,
	2019	2018	2019	2018
Unfavorable change in provision for loss and loss adjustment expenses for prior accident years	601	1,301	708	1,647

For the three months ended June 30, 2019, the Company reported $0.6 million of unfavorable development for loss and loss adjustment expenses from prior accident years compared with unfavorable development of $1.3 million for the three months ended June 30, 2018 (unfavorable development of $0.7 million year to date compared to unfavorable development of $1.6 million prior year to date). The unfavorable development reported for the three and six months ended June 30, 2019 and June 30, 2018 was related to an increase in loss and loss adjustment expenses at Amigo. During the three months ended June 30, 2019, Amigo increased loss reserves related to one of the remaining open claims as part of its continuing voluntary runoff.  During the three months ended June 30, 2018, Amigo re-estimated loss adjusting expense reserves for its remaining open claims simultaneous with the Company's announcement of the sale of Mendota.

See the "Critical Accounting Estimates and Assumptions" section of Management's Discussion and Analysis of Financial Condition included in the 2018 Annual Report for additional information pertaining to the Company’s process of estimating the provision for unpaid loss and loss adjustment expenses.

DEBT

Bank Loans

On October 12, 2017, the Company borrowed a principal amount of $5.0 million from a bank to partially finance its acquisition of PWSC (the "PWSC Loan"). The PWSC Loan has a fixed interest rate of 5.0% and is carried in the consolidated balance sheets at its unpaid principal balance. The PWSC Loan was scheduled to mature on October 12, 2022; however, the principal totaling $0.3 million was fully repaid on January 30, 2020.

60

KINGSWAY FINANCIAL SERVICES INC.

On March 1, 2019, the Company borrowed a principal amount of $10.0 million from a bank to finance its acquisition of Geminus (the "KWH Loan"). The KWH Loan matures on March 1, 2024 and has an annual interest rate equal to LIBOR plus 9.25%. The KWH Loan is carried in the consolidated balance sheets at its amortized cost, which reflects the quarterly pay-down of principal as well as the amortization of the discount using the effective interest rate method. See Note 13, "Debt," to the unaudited consolidated interim financial statements for further details.

Notes Payable

As part of the acquisition of CMC in July 2016, the Company assumed the Mortgage and recorded the Mortgage at its estimated fair value of $191.7 million, which included the unpaid principal amount of $180.0 million as of the date of acquisition plus a premium of $11.7 million. The Mortgage matures on May 15, 2034 and has a fixed interest rate of 4.07%. The Mortgage is carried in the consolidated balance sheets at its amortized cost, which reflects the monthly pay-down of principal as well as the amortization of the premium using the effective interest rate method.

On January 5, 2015, Flower Portfolio 001, LLC assumed a $9.2 million mortgage in conjunction with the purchase of investment real estate properties ("the Flower Note"). The Flower Note matures on December 10, 2031 and has a fixed interest rate of 4.81%. The Flower Note is carried in the consolidated balance sheets at its unpaid principal balance.

On October 15, 2015, Net Lease Investment Grade Portfolio LLC assumed a $9.0 million mezzanine debt in conjunction with the purchase of investment real estate properties ("the Net Lease Note"). The Net Lease Note matures on November 1, 2020 and has a fixed interest rate of 10.25%. The Net Lease Note is carried in the consolidated balance sheets at its unpaid principal balance.

Subordinated Debt

Between December 4, 2002 and December 16, 2003, six subsidiary trusts of the Company issued $90.5 million of 30-year capital securities to third parties in separate private transactions. In each instance, a corresponding floating rate junior subordinated deferrable interest debenture was then issued by Kingsway America Inc. to the trust in exchange for the proceeds from the private sale. The floating rate debentures bear interest at the rate of LIBOR, plus spreads ranging from 3.85% to 4.20%. The Company has the right to call each of these securities at par value any time after five years from their issuance until their maturity.

During the third quarter of 2018, the Company gave notice to its Trust Preferred trustees of its intention to exercise its voluntary right to defer interest payments for up to 20 quarters, pursuant to the contractual terms of its outstanding Trust Preferred indentures, which permit interest deferral. This action does not constitute a default under the Company's Trust Preferred indentures or any of its other debt indentures. At June 30, 2019, deferred interest payable of $5.7 million is included in accrued expenses and other liabilities in the consolidated balance sheets.

The Company's subordinated debt is measured and reported at fair value. At June 30, 2019, the carrying value of the subordinated debt is $50.2 million. The fair value of the subordinated debt is calculated using a model based on significant market observable inputs and inputs developed by a third party. For a description of the market observable inputs and inputs developed by a third party used in determining fair value of debt, see Note 21, "Fair Value of Financial Instruments," to the unaudited consolidated interim financial statements.

During the six months ended June 30, 2019, the market observable swap rates changed, and the Company experienced a decrease in the credit spread assumption developed by the third party. Changes in the market observable swap rates affect the fair value model in different ways. An increase in the LIBOR swap rates has the effect of increasing the fair value of the Company's subordinated debt while an increase in the risk-free swap rates has the effect of decreasing the fair value. The increase in the credit spread assumption has the effect of decreasing the fair value of the Company's subordinated debt while a decrease in the credit spread assumption has the effect of increasing the fair value. The other primary variable affecting the fair value of debt calculation is the passage of time, which will always have the effect of increasing the fair value of debt. The changes to the credit spread and swap rate variables during the six months ended June 30, 2019, along with the passage of time, contributed to the $0.2 million increase in fair value of the Company’s subordinated debt between December 31, 2018 and June 30, 2019.

Of the $0.2 million increase in fair value of the Company’s subordinated debt between December 31, 2018 and June 30, 2019, $1.7 million is reported as increase in fair value of debt attributable to instrument-specific credit risk in the Company's unaudited consolidated statements of comprehensive (loss) income and $1.5 million is reported as gain on change in fair value of debt in the Company’s unaudited consolidated statements of operations.

Also, as a result of the adoption of ASU 2016-01, a cumulative $40.5 million change in fair value of subordinated debt attributable to instrument-specific credit risk was reclassified from accumulated deficit to accumulated other comprehensive income (loss) as of January 1, 2018. As long as the Company repays its subordinated debt at maturity, it can be expected that this $40.5 million reclassification will reverse without being reported in the Company’s consolidated statements of operations. Though changes in

61

KINGSWAY FINANCIAL SERVICES INC.

the market observable swap rates will continue to introduce some volatility each quarter to the Company’s reported gain or loss on change in fair value of debt, changes in the credit spread assumption developed by the third party will no longer introduce volatility to the Company’s consolidated statements of operations. The fair value of the Company’s subordinated debt will eventually equal the principal value of the subordinated debt by the time of the stated redemption date of each trust, beginning with the trust maturing on December 4, 2032 and continuing through January 8, 2034, the redemption date of the last of the Company’s outstanding trusts.

For a description of each of the Company's six subsidiary trusts, see Note 13, "Debt," to the unaudited consolidated interim financial statements.

RECENTLY ISSUED ACCOUNTING STANDARDS

See Note 4, "Recently Issued Accounting Standards," to the unaudited consolidated interim financial statements, for discussion of certain accounting standards that may be applicable to the Company's current and future consolidated financial statements.

LIQUIDITY AND CAPITAL RESOURCES

The purpose of liquidity management is to ensure there is sufficient cash to meet all financial commitments and obligations as they fall due. The liquidity requirements of the Company and its subsidiaries have been met primarily by funds generated from operations, capital raising, disposal of discontinued operations, investment maturities and income and other returns received on investments or from the sale of investments. Cash provided from these sources is used primarily for making investments and for warranty expenses and loss and loss adjustment expense payments, debt servicing and other operating expenses. The timing and amount of payments for loss and loss adjustment expenses may differ materially from our provisions for unpaid loss and loss adjustment expenses, which may create increased liquidity requirements.

Cash Flows from Continuing Operations

During the six months ended June 30, 2019, the Company reported on the unaudited consolidated statements of cash flows $2.5 million of net cash used in operating activities from continuing operations. The reconciliation between the Company's reported net income of $2.8 million and the $2.5 million of net cash used in operating activities from continuing operations can be explained primarily by the $6.6 million gain on change in fair value of limited liability investments, at fair value.

During the six months ended June 30, 2019, the net cash used in investing activities from continuing operations as reported on the unaudited consolidated statements of cash flows was $6.7 million. This use of cash was driven primarily by purchases of fixed maturities in excess of proceeds from sales and maturities of fixed maturities and sales of other investments and from acquisition of business, net of cash acquired.

During the six months ended June 30, 2019, the net cash provided by financing activities from continuing operations as reported on the unaudited consolidated statements of cash flows was $5.8 million. This source of cash is attributed to $9.0 million of net bank loan proceeds offset by principal repayments on bank loans of $1.3 million and principal repayments of $1.8 million on the notes payable.

In summary, as reported on the unaudited consolidated statements of cash flows, the Company's net decrease in cash and cash equivalents from continuing operations during the six months ended June 30, 2019 was $3.4 million.

Receipt of dividends from the Company's insurance subsidiaries has not generally been considered a source of liquidity for the holding company. The insurance subsidiaries require regulatory approval for the return of capital and, in certain circumstances, prior to the payment of dividends. At June 30, 2019, the insurance subsidiaries of the Company were restricted from making any dividend payments to the holding company without regulatory approval pursuant to the domiciliary insurance regulations.

The Company's Extended Warranty subsidiaries fund their obligations primarily through service fee and commission income. The Company's Leased Real Estate subsidiary funds its obligations through rental income. The Company's insurance subsidiaries fund their obligations primarily through investment income and maturities in the investments portfolios.

The liquidity of the holding company is managed separately from its subsidiaries. Actions available to the holding company to increase liquidity in order to meet its obligations include the sale of passive investments; sale of subsidiaries; issuance of debt or equity securities; distributions from the Company’s Extended Warranty subsidiaries, as further described below; and giving notice to its Trust Preferred trustees of its intention to exercise its voluntary right to defer interest payments for up to 20 quarters on the six subsidiary trusts of the Company’s subordinated debt, which right the Company exercised during the third quarter of 2018.

62

KINGSWAY FINANCIAL SERVICES INC.

On March 1, 2019, the Company closed on the acquisition of Geminus, a specialty, full-service provider of vehicle service agreements and other finance and insurance products offered through its subsidiaries, The Penn Warranty Corporation ("Penn") and Prime Auto Care, Inc. ("Prime"). Geminus, Penn and Prime are included in Extended Warranty. Related to the Geminus acquisition, the Company secured the KWH Loan. IWS, Trinity, Geminus, Penn and Prime are borrowers under the KWH Loan. Pursuant to satisfying the covenants under the KWH Loan, IWS, Trinity, Geminus, Penn and Prime are permitted to make distributions to the holding company in an aggregate amount not to exceed $1.5 million in any 12-month period. Separately, pursuant to covenants under the PWSC Loan secured to partially finance the acquisition of PWSC on October 12, 2017, PWSC is not permitted to make distributions to the holding company without the consent of the lender. The PWSC Loan was scheduled to mature on October 12, 2022; however, the principal totaling $0.3 million was fully repaid on January 30, 2020.

Dividends from the Leased Real Estate segment are not generally considered a source of liquidity for the holding company. Because of the Lease Amendment, CMC may be in a position to distribute to the Company some of the cash received from the additional rental income. Any material cash flow to the Company, however, to help the Company meet its holding company obligations remains likely to occur only upon the occurrence of one of the three events described in the next paragraph that would trigger payment of service fees. There can be no assurance as to the timing of the occurrence, or the resulting outcome, from one of these events.

Pursuant to the terms of the management services agreement entered into at the closing of the acquisition of CMC, an affiliate of the seller (the "Service Provider") will provide certain services to CMC and its subsidiaries in exchange for service fees. Such services (collectively, the "Services") will include (i) causing an affiliate of the Service Provider to guaranty certain obligations of the Property Owner (pursuant to an Indemnity and Guaranty Agreement between such affiliate and the holder of the Mortgage (the "Mortgagor")), (ii) providing certain individuals to serve as members of the board of directors and/or certain executive officers of CMC and/or its subsidiaries and (iii) providing asset management services with respect to the Real Property. In exchange for the Services, the Property Owner will pay certain fees to the Service Provider. The payment of such service fees may be triggered by (i) a sale of the Real Property, (ii) a restructuring of the lease to which the Real Property is subject or (iii) a refinancing or restructuring of the Mortgage. The amount of the service fees will range from 40%-80% of the net proceeds generated by the event triggering the payment of the service fees (depending on the nature and timing of the triggering event). The Lease Amendment has not triggered the payment of service fees to the Service Provider.

The holding company’s liquidity, defined as the amount of cash in the bank accounts of Kingsway Financial Services Inc. and Kingsway America Inc., was $1.8 million and $1.9 million at June 30, 2019 and December 31, 2018, respectively. These amounts are reflected in the cash and cash equivalents of $10.9 million and $14.6 million reported at June 30, 2019 and December 31, 2018, respectively, on the Company’s consolidated balance sheets. The cash and cash equivalents and restricted cash other than the holding company’s liquidity represent restricted and unrestricted cash held by Amigo, Kingsway Re and the Company’s Extended Warranty and Leased Real Estate subsidiaries and are not considered to be available to meet holding company obligations, except as described above with respect to the Company’s Extended Warranty subsidiaries, which primarily consist of holding company operating expenses; transaction-related expenses; investments; and any other extraordinary demands on the holding company.

The holding company’s liquidity of $1.8 million at June 30, 2019 represented approximately four months of regularly recurring operating expenses before any transaction-related expenses, any new holding company investments or any other extraordinary demands on the holding company. As of the filing date of this report on Form 10-Q for the three and six months ended June 30, 2019, the holding company’s liquidity of $3.7 million represented approximately seven months of regularly recurring operating expenses before any transaction-related expenses, any new holding company investments or any other extraordinary demands on the holding company. During the third quarter of 2018, the Company gave notice to its Trust Preferred trustees of its intention to exercise its voluntary right to defer interest payments for up to 20 quarters, pursuant to the contractual terms of its outstanding Trust Preferred indentures, which permit interest deferral.

The holding company’s liquidity of $1.8 million at June 30, 2019 and $3.7 million as of the filing date of this report on Form 10-Q for the three and six months ended June 30, 2019 represents only actual cash on hand and does not include cash that would be made available to the holding company from the sale of investments, particularly investments in publicly traded securities, owned by the holding company. In addition, the holding company has access to some of the operating cash generated by the Extended Warranty subsidiaries as described above. While these sources do not represent cash of the holding company as of the filing date of this report on Form 10-Q for the three and six months ended June 30, 2019, they do represent future sources of liquidity.

As of March 31, 2020, there are 182,876 shares of the Company’s Class A Preferred Stock (the "Preferred Shares"), issued and outstanding. Any outstanding Preferred Shares would be required to be redeemed by the Company on April 1, 2021 ("Redemption Date") at a redemption value of $6.7 million (assuming all current outstanding Preferred Shares would be redeemed), if the Company has sufficient legally available funds to do so. Additionally, the Company has exercised its right to defer payment of

63

KINGSWAY FINANCIAL SERVICES INC.

interest on its outstanding subordinated debt ("trust preferred securities") and, because of the deferral which totaled $10.5 million at March 31, 2020, the Company is prohibited from redeeming any shares of its capital stock while payment of interest on the trust preferred securities is being deferred. If, as of April 1, 2021, the Company was required to pay both the deferred interest on the trust preferred securities and redeem all the Preferred Shares currently outstanding, then the Company currently projects that it would not have sufficient legally available funds to do so. However, the Company would be prohibited from doing so under Delaware law and, as such, (a) the interest estimated to be $14.9 million on March 31, 2021 on the trust preferred securities would remain on deferral as permitted under the indentures and (b) in accordance with Delaware law the Preferred Shares would not be redeemed on the Redemption Date (with a redemption value of $6.7 million) and would instead remain outstanding and continue to accrue dividends until such time as the Company has sufficient legally available funds to redeem the Preferred Shares and is not otherwise prohibited from doing so. In such a situation, the Company would continue to operate in the ordinary course.

The Company notes there are several variables to consider in such a situation, and management is currently exploring the following opportunities: negotiating with the holders of the Preferred Shares with respect to the Redemption Date and/or other key provisions, raising additional funds through capital market transactions, as well as the Company’s continued strategy of working to monetize its non-core investments while attempting to maximize the tradeoff between liquidity and value received. The Company also notes that the conversion of any Preferred Shares that might occur prior to April 1, 2021 would impact its analysis as of April 1, 2021.

Based on the Company’s current business plan and revenue prospects, existing cash, cash equivalents, investment balances and anticipated cash flows from operations are expected to be sufficient to meet the Company’s working capital and operating expenditure requirements, excluding the cash that may be required to redeem the Preferred Shares and deferred interest on its trust preferred securities, for the next twelve months. However, the Company’s assessment could also be affected by various risks and uncertainties, including, but not limited to, the effects of the COVID-19 pandemic.

Regulatory Capital

In the United States, a risk-based capital ("RBC") formula is used by the National Association of Insurance Commissioners ("NAIC") to identify property and casualty insurance companies that may not be adequately capitalized. In general, insurers reporting surplus as regards policyholders below 200% of the authorized control level, as defined by the NAIC, at December 31 are subject to varying levels of regulatory action, including discontinuation of operations. As of December 31, 2018, surplus as regards policyholders reported by Amigo exceeded the 200% threshold.

During the fourth quarter of 2012, the Company began taking steps to place all of Amigo into voluntary run-off. In April 2013, Kingsway filed a comprehensive run-off plan with the Florida Office of Insurance Regulation, which outlines plans for Amigo's run-off. Amigo remains in compliance with that plan.

Kingsway Re, our reinsurance subsidiary domiciled in Barbados, is required by the regulator in Barbados to maintain minimum statutory capital of $125,000. Kingsway Re is currently operating with statutory capital near the regulatory minimum, requiring us to periodically contribute capital to fund operating expenses. Kingsway Re incurs operating expenses of approximately $0.1 million per year.

OFF-BALANCE SHEET ARRANGEMENTS

The Company has off-balance sheet arrangements related to guarantees, which are further described in Note 23, "Commitments and Contingent Liabilities," to the unaudited consolidated interim financial statements.

Item 3. Quantitative and Qualitative Disclosures about Market Risk

Market Risk

Market risk is the risk that we will incur losses due to adverse changes in interest or currency exchange rates and equity prices. We have exposure to market risk through our investment activities and our financing activities.

Given our U.S. operations typically invest in U.S. dollar denominated fixed maturity instruments, our primary market risk exposures in the investments portfolio are to changes in interest rates. Periodic changes in interest rate levels generally affect our financial results to the extent that the investments are recorded at market value and reinvestment yields are different than the original yields on maturing instruments. During periods of rising interest rates, the market values of the existing fixed maturities will generally decrease. The reverse is true during periods of declining interest rates.

We manage our exposure to risks associated with interest rate fluctuations through active review of our investment portfolio by our management and Board of Directors, consultation with third-party financial advisors and by managing the maturity profile of our fixed maturity portfolio. Our goal is to maximize the total after-tax return on all of our investments. An important strategy

64

KINGSWAY FINANCIAL SERVICES INC.

we employ to achieve this goal is to try to hold enough in cash and short-term investments in order to avoid liquidating longer-term investments to pay loss and loss adjustment expenses or warranty contract expenses.

Table 8 below summarizes the fair value by contractual maturities of the fixed maturities portfolio, excluding cash and cash equivalents, at June 30, 2019 and December 31, 2018.

TABLE 8 Fair value of fixed maturities by contractual maturity date

(in thousands of dollars, except for percentages)

	June 30, 2019	% of Total		December 31, 2018	% of Total
Due in less than one year	11,672	56.2	%	5,445	44.4	%
Due in one through five years	7,650	36.8	%	5,233	42.7	%
Due after five through ten years	192	0.9	%	210	1.7	%
Due after ten years	1,273	6.1	%	1,372	11.2	%
Total	20,787	100.0	%	12,260	100.0	%

At June 30, 2019, 93.0% of fixed maturities, including treasury bills, government bonds and corporate bonds, had contractual maturities of five years or less. Actual maturities may differ from contractual maturities because certain issuers have the right to call or prepay obligations with or without call or prepayment penalties. The Company holds cash and high-grade short-term assets that, along with fixed maturities, management believes are sufficient in amount for the payment of unpaid loss and loss adjustment expenses, warranty contract expenses and other obligations on a timely basis. In the event additional cash is required to meet obligations to our policyholders and customers, we believe the high-quality investments in the portfolios provide us with sufficient liquidity.

Based upon the results of interest rate sensitivity analysis, Table 9 below shows the interest rate risk of our investments in fixed maturities, measured in terms of fair value (which is equal to the carrying value for all our fixed maturity securities), at June 30, 2019 and December 31, 2018.

TABLE 9 Sensitivity analysis on fixed maturities

(in thousands of dollars)

	100 Basis Point Decrease in Interest Rates		No Change		100 Basis Point Increase in Interest Rates
As of June 30, 2019
Estimated fair value	$	21,005	$	20,787	$	20,569
Estimated increase (decrease) in fair value	$	218	$	—	$	(218	)
As of December 31, 2018
Estimated fair value	$	12,436	$	12,260	$	12,084
Estimated increase (decrease) in fair value	$	176	$	—	$	(176	)

We use both fixed and variable rate debt as sources of financing. Because our subordinated debt and KWH Loan are LIBOR-based, our primary market risk related to financing activities is to changes in LIBOR. As of June 30, 2019, each one hundred basis point increase in LIBOR would result in an approximately $1.0 million increase in our annual interest expense.

Equity Risk

Equity risk is the risk we will incur economic losses due to adverse changes in equity prices. Our exposure to changes in equity prices results from our holdings of common stock. We principally manage equity price risk through industry and issuer diversification and asset allocation techniques and by continuously evaluating market conditions.

Credit Risk

Credit risk is defined as the risk of financial loss due to failure of the other party to a financial instrument to discharge an obligation. Credit risk arises from our positions in short-term investments, corporate debt instruments and government bonds.

65

KINGSWAY FINANCIAL SERVICES INC.

The Investment Committee of the Board of Directors is responsible for the oversight of key investment policies and limits. These policies and limits are subject to annual review and approval by the Investment Committee. The Investment Committee is also responsible for ensuring these policies are implemented and procedures are in place to manage and control credit risk.

Table 10 below summarizes the composition of the fair values of fixed maturities, excluding cash and cash equivalents, at June 30, 2019 and December 31, 2018, by rating as assigned by Standard and Poor's ("S&P") or Moody's Investors Service ("Moody's"). Fixed maturities consist of predominantly high-quality instruments in corporate and government bonds with 100.0% of those investments rated 'A' or better at June 30, 2019.

TABLE 10 Credit ratings of fixed maturities

(ratings as a percentage of total fixed maturities)

Rating (S&P/Moody's)	June 30, 2019		December 31, 2018
AAA/Aaa	71.9	%	72.0	%
AA/Aa	10.5		16.1
A/A	17.6		10.9
Percentage rated A/A2 or better	100.0	%	99.0	%
BBB/Baa	—		1.0
Total	100.0	%	100.0	%

Item 4. Controls and Procedures

Evaluation of Disclosure Controls and Procedures

The Company’s management, with the participation of our Chief Executive Officer and Chief Financial Officer, has conducted an evaluation of the effectiveness of the Company’s disclosure controls and procedures (as defined in Rule 13a-15(e) and 15d-15(e) under the Securities Exchange Act of 1934, as amended (the "Exchange Act") as of June 30, 2019. The Company’s disclosure controls and procedures are designed to ensure that information required to be disclosed in the reports the Company files under the Exchange Act is recorded, processed, summarized and reported within the time periods specified in the SEC’s rules and forms and that such information is accumulated and communicated to the Company’s management, including the Company’s Chief Executive Officer and Chief Financial Officer, to allow for timely decisions regarding required disclosures. In designing and evaluating our disclosure controls and procedures, the Company’s management recognizes that disclosure controls and procedures, no matter how well conceived and operated, can provide only reasonable, not absolute, assurance that the objectives of the disclosure controls and procedures are met.  Our disclosure controls and procedures have been designed to meet reasonable assurance standards.   In addition, the design of disclosure controls and procedures must reflect the fact that there are resource constraints that require the Company’s management to apply its judgment in evaluating the benefits of possible controls and procedures relative to their costs. The design of any disclosure controls and procedures also is based in part upon certain assumptions about the likelihood of future events, and there can be no assurance that any design will succeed in achieving its stated goals under all potential future conditions.

Based on the evaluation of our disclosure controls and procedures, the Company's Chief Executive Officer and Chief Financial Officer have concluded that, as of June 30, 2019, the Company’s disclosure controls and procedures were not effective as a result of material weaknesses in the Company's internal control over financial reporting related to the accounting for and disclosure of certain complex and nonrecurring transactions; the accounting for and disclosure of certain other items; monitoring the collectability of accounts receivable balances; other-than-temporary impairment on equity method investments; and certain account reconciliations. The material weaknesses were discovered during the course of the 2018 external audit of the accounts and, as such, not all material weaknesses necessarily present the same risks from period to period as a result of differing events and transactions which have occurred or may occur in current and future periods.

Material Weaknesses in Internal Control over Financial Reporting

A material weakness is defined as a deficiency or combination of deficiencies in internal control over financial reporting such that there is a reasonable possibility that a material misstatement of annual or interim consolidated financial statements will not be prevented or detected on a timely basis.

With respect to the accounting for and disclosure of certain complex and nonrecurring transactions, the execution of the controls over the application of accounting literature did not operate effectively with respect to:

• the reclassification of investment income, related to equity method investments, from loss from discontinued operations, net of taxes to net investment income in the consolidated statement of operations;

66

KINGSWAY FINANCIAL SERVICES INC.

• the identification, accounting and disclosure of investments demonstrating characteristics of variable interest entities, including the consolidation of certain investments;

• the adoption and application of ASU 2014-09;

• identification, disclosure and accounting for equity-classified warrants; and

• purchase accounting, as it relates to the identification and valuation of intangible assets and goodwill.

Concerning the accounting for and disclosure of certain other items, the execution of the controls over the application of accounting literature did not operate effectively with respect to separating restricted cash from cash and cash equivalents on the face of the consolidated balance sheet. Additionally, the Company did not have adequate controls in place pertaining to disclosure of related parties.

Regarding the collectability of accounts receivable balances, the Company did not have adequate controls and procedures with respect to evaluating balances for collectability, including the lack of a formal policy governing the review of accounts, as well as calculating and documenting necessary reserves.

With respect to other-than-temporary impairment on equity method investments, the Company did not properly apply the accounting literature when performing its analysis in determining whether its investment in investee was other-than-temporarily impaired as of December 31, 2018.

Finally, with respect to the lack of adequate procedures regarding certain account reconciliations, there were errors in the reconciliation of account balances as they were not performed timely and/or at a level of precision to identify errors and incorrect balance sheet and income statement classification for certain cash, receivable, deposit, accounts payable, deferred revenue, escheat liability and investment income accounts.

These matters were discovered during the course of the 2018 external audit of the accounts and were reviewed with the Company's Audit Committee. Certain of these material weaknesses resulted in the restatement described in Note 3, "Restatement of Previously Issued Financial Statements," to the Annual Report on Form 10-K for the year ended December 31, 2018, filed on February 27, 2020.

As a result of the identified material weaknesses, the Company’s management directed a comprehensive review of its consolidated financial statements to assess the possibility of further material misstatements that may remain unidentified. As a result of such review, and notwithstanding the material weaknesses described above, the Company’s management, including the Company’s Chief Executive Officer and Chief Financial Officer, believes that the unaudited consolidated financial statements contained in this Form 10-Q for the three and six months ended June 30, 2019 and June 30, 2018 fairly present, in all material respects, our financial condition, results of operations and cash flows for the periods presented in conformity with U.S. GAAP.

Remediation Process

The Company has been evaluating the material weaknesses and is developing a plan of remediation to strengthen the effectiveness of the design and operation of its internal control environment. The remediation plan will include the following actions:

• Perform a comprehensive assessment of all existing accounting policies and revise existing policies and/or introduce new policies, as needed;

• Enhance the formality of its review procedures with respect to its accounting for any new investments, as well as the periodic evaluation of existing investments;

• Implement additional review procedures with respect to its accounting under ASU 2014-09 to ensure the Company’s accounting will continue to be in accordance with that standard on a go-forward basis;

• Implement additional identification, accounting and review controls with respect to complex and nonrecurring transactions, as well as augment existing staff with outside skilled accounting resources, as appropriate, and strengthen the review process to improve the operation of financial reporting and corresponding internal controls;

• Enhance the formality and rigor with respect to identifying and tracking all material related party transactions, as well updating its disclosures controls to enhance the focus on related party disclosure requirements; and

• Enhance the formality and rigor of review with respect to the collectability of accounts receivable balances, and the account reconciliation procedures.

The actions that the Company is taking are subject to ongoing senior management review as well as Audit Committee oversight. The Company is committed to maintaining a strong internal control environment and believes that these remediation efforts will represent significant improvements in its controls. The Company has started to implement these steps; however, some of these steps will take time to be fully integrated and confirmed to be effective and sustainable. Additional controls may also be required over time. Until the remediation steps set forth above are fully implemented and tested, the material weaknesses described above will continue to exist.

67

KINGSWAY FINANCIAL SERVICES INC.

Changes in Internal Control over Financial Reporting

There have been no changes in the Company's internal control over financial reporting during the period beginning January 1, 2019, and ending June 30, 2019, that have materially affected, or are reasonably likely to materially affect, the Company's internal control over financial reporting.

PART II. OTHER INFORMATION

Item 1. Legal Proceedings

Information concerning pending legal proceedings is incorporated herein by reference to Note 23, "Commitments and Contingencies," to the unaudited consolidated interim financial statements in Part I of this Form 10-Q.

Item 1A. Risk Factors

Except as set forth below, as of the date of this report, there have been no material changes with respect to those risk factors previously disclosed in our 2018 Annual Report.

We will be adversely impacted by the outbreak of COVID-19

In March 2020, the outbreak of COVID-19 caused by a novel strain of the coronavirus was recognized as a pandemic by the World Health Organization. Shortly thereafter, the President of the United States declared a National Emergency throughout the United States attributable to such outbreak. The outbreak has become increasingly widespread in the United States, including in the markets in which we operate. We are currently taking steps to assess the effects, and mitigate the adverse consequences to our businesses, of the outbreak; however, though the magnitude of the impact remains to be seen, our businesses will be adversely impacted by the outbreak of COVID-19.

In addition to adverse United States domestic and global macroeconomic effects, including the adverse impacts on automobile sales and new home construction, which may decrease consumer demand for our products and services, reduce our ability to access capital, and otherwise adversely impact the operation of our businesses, the outbreak of COVID-19 has caused, and will continue to cause, substantial disruption to our employees, distribution channels, investors, tenants, and customers through self-isolation, travel limitations, business restrictions, and otherwise. Many areas within the United States have imposed mandatory closures for businesses not deemed to be essential, and it is currently unclear for how long such closures will last. Though most of our employees are able to work remotely, these closures have nevertheless affected many of our customers and many businesses through which we sell our products and services, resulting in significant declines in sales. These effects, individually or in the aggregate, will adversely impact our businesses, financial condition, operating results and cash flows and such adverse impacts may be material.

Any of the foregoing factors, or other cascading effects of the COVID-19 pandemic that are not currently foreseeable, could materially increase our costs, negatively impact our sales and damage the company’s results of operations and its liquidity position, possibly to a significant degree. The duration of any such impacts cannot be predicted.

A difficult economy generally could materially adversely affect our business, results of operations or financial condition.

An adverse change in market conditions, including changes caused by the COVID-19 pandemic, leading to instability in the global credit markets presents additional risks and uncertainties for our business. Depending on market conditions going forward, we could incur substantial realized and unrealized losses in future periods, which could have an adverse affect on our results of operations or financial condition. Certain trust accounts and letters of credit for the benefit of related companies and third-parties have been established with collateral on deposit under the terms and conditions of the relevant trust and/or letter of credit agreements. The value of collateral could fall below the levels required under these agreements putting the subsidiary or subsidiaries in breach of the agreements.

Market volatility may also make it more difficult to value certain of our investments if trading becomes less frequent. Disruptions, uncertainty and volatility in the global credit markets may also adversely affect our ability to obtain financing for future acquisitions. If financing is available, it may only be available at an unattractive cost of capital, which would decrease our profitability. There can be no assurance that market conditions will not deteriorate in the near future.

68

KINGSWAY FINANCIAL SERVICES INC.

Financial disruption or a prolonged economic downturn could materially and adversely affect our business.

Worldwide financial markets have recently experienced periods of extraordinary disruption and volatility, which has been exacerbated by the COVID-19 pandemic, resulting in heightened credit risk, reduced valuation of investments and decreased economic activity. Moreover, many companies have experienced reduced liquidity and uncertainty as to their ability to raise capital during such periods of market disruption and volatility. In the event that these conditions recur or result in a prolonged economic downturn, our results of operations, financial position and/or liquidity could be materially and adversely affected. These market conditions may affect the Company's ability to access debt and equity capital markets. In addition, as a result of recent financial events, we may face increased regulation. Many of the other risk factors discussed in this Risk Factors section identify risks that result from, or are exacerbated by, financial economic downturn. These include risks related to our investments portfolio, the competitive environment and regulatory developments.

Item 2. Unregistered Sales of Equity Securities and Use of Proceeds

None

Item 3. Defaults Upon Senior Securities

None

Item 4. Mine Safety Disclosures

Not applicable.

Item 5. Other Information

None

69

KINGSWAY FINANCIAL SERVICES INC.

Item 6. Exhibits

31.1	Certification of Principal Executive Officer pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.
31.2	Certification of Principal Financial Officer pursuant to Section 302 of the Sarbanes-Oxley Act of 2002.
32.1	Certification of Principal Executive Officer pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.
32.2	Certification of Principal Financial Officer pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.
101.INS	XBRL Instance Document
101.SCH	XBRL Taxonomy Extension Schema
101.CAL	XBRL Taxonomy Extension Calculation Linkbase
101.DEF	XBRL Taxonomy Extension Definition Linkbase
101.LAB	XBRL Taxonomy Extension Label Linkbase
101.PRE	XBRL Taxonomy Extension Presentation Linkbase

70

KINGSWAY FINANCIAL SERVICES INC.

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the Registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized.

			KINGSWAY FINANCIAL SERVICES INC.
Date:	April 10, 2020	By:	/s/ John T. Fitzgerald
			John T. Fitzgerald, President, Chief Executive Officer and Director
			(principal executive officer)
Date:	April 10, 2020	By:	/s/ Kent A. Hansen
			Kent A. Hansen, Chief Financial Officer and Executive Vice President
			(principal financial officer)

71

EX-31.1

EXHIBIT 31.1

CERTIFICATION PURSUANT TO SECTION 302

Certification of Chief Executive Officer pursuant to Section 302 of the Sarbanes-Oxley Act of 2002

I, John T. Fitzgerald, certify that:

1. I have reviewed this report on Form 10-Q of Kingsway Financial Services Inc.;

2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

3. Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;

4. The registrant's other certifying officer and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:

a) Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

b) Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;

c) Evaluated the effectiveness of the registrant's disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

d) Disclosed in this report any change in the registrant's internal control over financial reporting that occurred during the registrant's most recent fiscal quarter (the registrant's fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant's internal control over financial reporting; and

5. The registrant's other certifying officer and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant's auditors and the audit committee of the registrant's board of directors (or persons performing the equivalent functions):

a) All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant's ability to record, process, summarize and report financial information; and

b) Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant's internal control over financial reporting.

Date: April 10, 2020

By /s/ John T. Fitzgerald

John T. Fitzgerald, President and Chief Executive Officer

(Principal Executive Officer)

EX-31.2

EXHIBIT 31.2

CERTIFICATION

Certification of Chief Financial Officer pursuant to Section 302 of the Sarbanes-Oxley Act of 2002

I, Kent A. Hansen, certify that:

1. I have reviewed this Form 10-Q of Kingsway Financial Services Inc.;

2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

3. Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;

4. The registrant's other certifying officer and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) and internal control over financial reporting (as defined in Exchange Act Rules 13a-15(f) and 15d-15(f)) for the registrant and have:

(a) Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

(b) Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;

(c) Evaluated the effectiveness of the registrant's disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

(d) Disclosed in this report any change in the registrant's internal control over financial reporting that occurred during the registrant's most recent fiscal quarter (the registrant's fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant's internal control over financial reporting; and

5. The registrant's other certifying officer and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant's auditors and the audit committee of the registrant's board of directors (or persons performing the equivalent functions):

(a) All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant's ability to record, process, summarize and report financial information; and

(b) Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant's internal control over financial reporting.

Date: April 10, 2020

By /s/ Kent A. Hansen

Kent A. Hansen, Chief Financial Officer and Executive Vice President

(Principal Financial Officer)

EX-32.1

EXHIBIT 32.1

CERTIFICATION PURSUANT TO

18 U.S.C. SECTION 1350,

AS ADOPTED PURSUANT TO

SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

In connection with the Quarterly Report on Form 10-Q of Kingsway Financial Services Inc. (the “Company”) for the period ended June 30, 2019 as filed with the Securities and Exchange Commission on the date hereof (the "Report"), the undersigned John T. Fitzgerald, the President and Chief Executive Officer and Principal Executive Officer of the Company, hereby certifies, pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002, that, to the best of the undersigned's knowledge and belief:

(1) the Report fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and

(2) the information contained in the Report fairly presents, in all material respects, the financial condition and results of operations of the Company.

Date: April 10, 2020

By /s/ John T. Fitzgerald

John T. Fitzgerald, President and Chief Executive Officer

(Principal Executive Officer)

EX-32.2

EXHIBIT 32.2

CERTIFICATION PURSUANT TO

18 U.S.C. SECTION 1350,

AS ADOPTED PURSUANT TO

SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

In connection with the Quarterly Report on Form 10-Q of Kingsway Financial Services Inc. (the “Company”) for the period ended June 30, 2019 as filed with the Securities and Exchange Commission on the date hereof (the "Report"), the undersigned Kent A. Hansen, the Chief Financial Officer and Principal Financial Officer of the Company, hereby certifies, pursuant to 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002, that, to the best of the undersigned's knowledge and belief:

(1) the Report fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange Act of 1934; and

(2) the information contained in the Report fairly presents, in all material respects, the financial condition and results of operations of the Company.

Date: April 10, 2020

By /s/ Kent A. Hansen

Kent A. Hansen, Chief Financial Officer and Executive Vice President

(Principal Financial Officer)

XML

Segmented Information - Additional Information (Details)	6 Months Ended
	Jun. 30, 2019 a segment state
Segment Reporting [Abstract]
Number of reportable segments | segment	2
Number of states in which entity operates | state	23
Land subject to ground leases | a	192

XML

Related Parties - Itasca Capital Ltd. (Details) $ / shares in Units, $ / shares in Units, $ in Millions, $ in Millions								6 Months Ended	12 Months Ended
	Nov. 19, 2019 USD ($) $ / shares shares	Oct. 31, 2019 CAD ($) $ / shares shares	Oct. 09, 2019 CAD ($) $ / shares shares	Sep. 30, 2019 USD ($) $ / shares shares	Sep. 05, 2018 shares	Nov. 17, 2017 USD ($)	Jun. 10, 2016 USD ($)	Jun. 30, 2019 shares	Dec. 31, 2018 shares
Board of Directors Chairman
Related Party Transaction [Line Items]
Equity method investment, ownership percentage								40.60%	40.60%
Chief Financial Officer
Related Party Transaction [Line Items]
Payments to acquire management contract rights | $						$ 0.0	$ 0.0
Affiliated Entity
Related Party Transaction [Line Items]
Equity method investment, ownership percentage								0.00%	0.00%
Corporate Segment
Related Party Transaction [Line Items]
Equity method investment, ownership percentage								22.90%	22.90%
Fundamental Global Investors, LLC | Kingsway Financial Services, Inc
Related Party Transaction [Line Items]
Ownership percentage (less than at June 30, 2019)								5.00%	5.00%
Restricted Stock
Related Party Transaction [Line Items]
Shares unvested (in shares)								976,950	1,092,450
2018 Restricted Stock Awards | Restricted Stock
Related Party Transaction [Line Items]
Shares unvested (in shares)								500,000
Former Chief Executive Officer | 2018 Restricted Stock Awards | Restricted Stock
Related Party Transaction [Line Items]
Shares granted (in shares)					350,000
Shares withheld for tax obligation (in shares)					102,550
Shares unvested (in shares)					247,450
Subsequent Event
Related Party Transaction [Line Items]
Consideration received, cash | $	$ 0.6			$ 0.6
Consideration received (in shares)	594,750			594,750
Consideration received, warrants (in shares)	400,000			400,000
Warrant exercise price (in dollars per share) | $ / shares	$ 15			$ 15
Subsequent Event | ICL | ICL | Affiliated Entity
Related Party Transaction [Line Items]
Number of shares to be sold (in shares)		3,011,447	1,974,113
Share price (in dollars per share) | $ / shares		$ 0.35	$ 0.35
Subsequent Event | ICL | ICL | Affiliated Entity | Execution of Share Agreement With Related Party
Related Party Transaction [Line Items]
Amount of related party transaction | $		$ 1.1	$ 0.7
Number of shares (in shares)		247,450
Subsequent Event | ICL | ICL | Affiliated Entity | Execution of Share Agreement With Related Party, Portion Received in Cash
Related Party Transaction [Line Items]
Amount of related party transaction | $		$ 0.2

XML

Investments - Additional Information (Details)		3 Months Ended					6 Months Ended
	Jan. 02, 2018 USD ($)	Mar. 31, 2020 USD ($)	Dec. 31, 2019 USD ($)	Sep. 30, 2019 USD ($)	Jun. 30, 2019 USD ($) day $ / shares shares	Jun. 30, 2018 USD ($) $ / shares	Jun. 30, 2019 USD ($) day $ / shares shares	Jun. 30, 2018 USD ($) $ / shares	Mar. 31, 2019 USD ($)	Dec. 31, 2018 USD ($)	Jul. 24, 2018 $ / shares	Oct. 25, 2017 $ / shares
Debt Securities, Available-for-sale [Line Items]
Securities in unrealized loss positions					44		44			64
Other-than-temporary impairment loss					$ 0	$ 0	$ 75,000	$ 0
Limited liability investments					3,891,000		3,891,000			$ 4,790,000
(Gain) loss on change in fair value of limited liability investments, at fair value					2,347,000	(525,000)	6,612,000	(1,461,000)
Limited liability investments, at fair value					33,047,000		33,047,000			26,015,000
Investment impairment losses					0	0	0	0
Unfunded commitments					600,000		600,000
Investments in private companies, at adjusted cost					2,661,000		2,661,000			3,090,000
Net change in unrealized gain (loss) on private company investments					0	$ (155,000)	19,000	(155,000)
Other-than-temporary impairment loss							75,000	$ 0
Real estate investments					10,662,000		10,662,000			10,662,000
Other investments					$ 895,000		$ 895,000			2,079,000
Stock price threshold trading days | day					20		20
Threshold trading days | day					30		30
Restricted cash					$ 17,320,000		$ 17,320,000			16,959,000
Variable Interest Entity, Primary Beneficiary
Debt Securities, Available-for-sale [Line Items]
Unfunded commitments					$ 600,000		$ 600,000
Performance Share Grant Agreement
Debt Securities, Available-for-sale [Line Items]
Stock reserved for future issuances (in shares) | shares					475,000		475,000
Minimum
Debt Securities, Available-for-sale [Line Items]
Stock reserved for future issuances (in shares) | shares					100,000		100,000
Share price (in dollars per share) | $ / shares						$ 10.00		$ 10.00
Maximum
Debt Securities, Available-for-sale [Line Items]
Share price (in dollars per share) | $ / shares					$ 18		$ 18				$ 18.00
Clause 2
Debt Securities, Available-for-sale [Line Items]
Stock reserved for future issuances (in shares) | shares					125,000		125,000
Share price (in dollars per share) | $ / shares					$ 12.00		$ 12.00				12.00
Clause 1 and 2
Debt Securities, Available-for-sale [Line Items]
Stock reserved for future issuances (in shares) | shares					225,000		225,000
Clause 3
Debt Securities, Available-for-sale [Line Items]
Share price (in dollars per share) | $ / shares					$ 15		$ 15				$ 15.00
Clause 1, 2 and 3
Debt Securities, Available-for-sale [Line Items]
Stock reserved for future issuances (in shares) | shares					350,000		350,000
Management
Debt Securities, Available-for-sale [Line Items]
Share price (in dollars per share) | $ / shares												$ 7.85
Consideration received on transaction	$ 300,000
Proceeds from sale of available-for-sale debt securities								$ 300,000
Mendota
Debt Securities, Available-for-sale [Line Items]
Escrow deposit					$ 5,100,000		$ 5,100,000			5,000,000
IWS
Debt Securities, Available-for-sale [Line Items]
Restricted cash									$ 10,000,000
State and Provincial Regulatory Authorities
Debt Securities, Available-for-sale [Line Items]
Restricted cash equivalents					200,000		200,000			200,000
Restricted cash					1,900,000		1,900,000			1,900,000
Third Parties
Debt Securities, Available-for-sale [Line Items]
Restricted cash					300,000		300,000			100,000
Private Company Investments
Debt Securities, Available-for-sale [Line Items]
Other-than-temporary impairment loss					0	$ 0	0	$ 0
Significant Other Observable Inputs (Level 2)
Debt Securities, Available-for-sale [Line Items]
Real estate investments					0		0			0
Other investments					$ 895,000		$ 895,000			$ 2,079,000
1347 Investors LLC
Debt Securities, Available-for-sale [Line Items]
Ownership interest								26.70%
Subsequent Event
Debt Securities, Available-for-sale [Line Items]
(Gain) loss on change in fair value of limited liability investments, at fair value		$ (600,000)	$ (700,000)	$ (2,700,000)
Investment impairment losses		$ 700,000
Other than temporary impairment losses, investments, percent		90.00%

XML

Investments - Fixed Maturities by Contractual Maturity Periods (Details) - USD ($) $ in Thousands	Jun. 30, 2019	Dec. 31, 2018
Amortized Cost
Due in one year or less	$ 11,652
Due after one year through five years	7,641
Due after five years through ten years	194
Due after ten years	1,284
Amortized Cost	20,771	$ 12,432
Estimated Fair Value
Due in one year or less	11,672
Due after one year through five years	7,650
Due after five years through ten years	192
Due after ten years	1,273
Estimated Fair Value, Fixed Maturities	$ 20,787	$ 12,260

XML

Stock-Based Compensation - Additional Information (Details) - USD ($) $ / shares in Units, $ in Thousands				3 Months Ended				6 Months Ended
	Jan. 31, 2019	Sep. 07, 2018	Sep. 05, 2018	Jun. 30, 2019	Mar. 31, 2019	Sep. 30, 2018	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018	Dec. 31, 2019	Dec. 31, 2018
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Granted (in shares)								0
Payroll tax expense								$ 89	$ 0
2014 Restricted Stock Awards | Former Chief Executive Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Forfeited (in shares)			1,382,665
Restricted Stock
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares unvested (in shares)				976,950				976,950			1,092,450
Vested (in shares)					(79,231.000)
Weighted-average grant date fair value (in dollars per share)				$ 4.55				$ 4.55			$ 4.51
Restricted Stock | 2014 Restricted Stock Awards
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Award requisite service period								10 years
Unamortized compensation expense				$ 500				$ 500
Shares unvested (in shares)				229,500				229,500
Restricted Stock | 2014 Restricted Stock Awards | Former Chief Executive Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Stock-based compensation expense, net of forfeitures						$ (2,400)
Restricted Stock | 2014 Restricted Stock Awards | Former Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares withheld for tax obligation (in shares)	36,269
Vested (in shares)	115,500
Payroll tax expense					$ 100
Restricted Stock | 2018 Restricted Stock Awards
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares unvested (in shares)				500,000				500,000
Restricted Stock | 2018 Restricted Stock Awards | Former Chief Executive Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unamortized compensation expense				$ 600				$ 600
Shares granted (in shares)			350,000
Shares withheld for tax obligation (in shares)			102,550
Shares unvested (in shares)			247,450
Restricted Stock | 2018 Restricted Stock Awards | Former Chief Executive Officer | Forecast | Subsequent Event
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares unvested (in shares)										247,450
Restricted Stock | Modified Restricted Stock Award
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unamortized compensation expense				$ 0				$ 0
Stock-based compensation expense, net of forfeitures					$ 100
Vested (in shares)					79,231
Restricted Stock | 2018 Modified Restricted Stock Award
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Shares unvested (in shares)				247,450				247,450
Restricted Stock | PWSC Restricted Stock Award | Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unamortized compensation expense				$ 700				$ 700
Stock-based compensation expense, net of forfeitures				$ 200			$ 300	$ 400	$ 600
Shares granted (in shares)		1,000
Shares unvested (in shares)				875				875
Weighted-average grant date fair value (in dollars per share)				$ 824.47				$ 824.47
Restricted Stock Units (RSUs) | 2018 Restricted Stock Awards | Officer
Share-based Compensation Arrangement by Share-based Payment Award [Line Items]
Unamortized compensation expense				$ 1,800				$ 1,800
Shares granted (in shares)			500,000

XML

Fair Value of Financial Instruments - Assets and Liabilities Measured at Fair Value on a Nonrecurring Basis (Details) - USD ($)	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Net change in unrealized gain (loss) on private company investments	$ 0	$ (155,000)	$ 19,000	$ (155,000)
Other-than-temporary impairment loss			75,000	0
Recurring
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Other-than-temporary impairment loss	$ 0	$ 0	$ 0	$ 0

XML

Intangible Assets - Schedule of Intangible Assets (Details) - USD ($) $ in Thousands	Jun. 30, 2019	Dec. 31, 2018
Gross Carrying Value
Total	$ 99,566	$ 93,860
Accumulated Amortization
Intangible assets, accumulated amortization	11,791	10,594
Net Carrying Value
Total	87,775	83,266
Tenant relationship
Gross Carrying Value
Intangible assets not subject to amortization	73,667	73,667
Accumulated Amortization
Intangible assets, accumulated amortization	0
Net Carrying Value
Intangible assets not subject to amortization	73,667	73,667
Trade names
Gross Carrying Value
Intangible assets not subject to amortization	3,264	1,290
Accumulated Amortization
Intangible assets, accumulated amortization	0
Net Carrying Value
Intangible assets not subject to amortization	3,264	1,290
Database
Gross Carrying Value
Intangible assets subject to amortization	4,918	4,918
Accumulated Amortization
Intangible assets, accumulated amortization	3,259	3,013
Net Carrying Value
Intangible assets subject to amortization	1,659	1,905
Vehicle service agreements in-force
Gross Carrying Value
Intangible assets subject to amortization	3,680	3,680
Accumulated Amortization
Intangible assets, accumulated amortization	3,675	3,671
Net Carrying Value
Intangible assets subject to amortization	5	9
Customer relationships
Gross Carrying Value
Intangible assets subject to amortization	12,646	8,914
Accumulated Amortization
Intangible assets, accumulated amortization	4,580	3,691
Net Carrying Value
Intangible assets subject to amortization	8,066	5,223
In-place lease
Gross Carrying Value
Intangible assets subject to amortization	1,125	1,125
Accumulated Amortization
Intangible assets, accumulated amortization	186	155
Net Carrying Value
Intangible assets subject to amortization	939	970
Non-compete
Gross Carrying Value
Intangible assets subject to amortization	266	266
Accumulated Amortization
Intangible assets, accumulated amortization	91	64
Net Carrying Value
Intangible assets subject to amortization	$ 175	$ 202

XML

Related Parties - AK Realty I LLC (Details)	Jun. 30, 2019	Dec. 31, 2018	Jul. 26, 2017	Sep. 21, 2015
Equity Method Investee
Related Party Transaction [Line Items]
Equity method investment, ownership percentage	47.60%	47.60%	51.00%	33.30%

XML

Fair Value of Financial Instruments - Reconciliation of Fair Value of Recurring Level 3 Measurements (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018	Dec. 31, 2018
Limited liability investments, at fair value:
Beginning balance			$ 26,015
Purchases			(249)	$ (95)
Net realized (losses) gains	$ (556)	$ 132	(241)	397
Ending balance	33,047		33,047
Real estate investments:
Beginning balance			10,662
Ending balance	10,662		10,662
Total assets	65,747		65,747		$ 52,024
Warrant liability:
Ending balance - liabilities	307		307
Significant Unobservable Inputs (Level 3)
Limited liability investments, at fair value:
Beginning balance	4,060	1,634	4,124	1,397
Purchases	599	504	674	978
Distributions received	(14)	(70)	(338)	(562)
Net realized (losses) gains	14	0	83	251
Change in fair value of limited liability investments, at fair value included in net income (loss)	(24)	15	92	19
Ending balance	4,635	2,083	4,635	2,083
Unrealized gains recognized in net (loss) income on limited liability investments, at fair value held at end of period	0	15	116	38
Real estate investments:
Beginning balance	10,662	10,662	10,662	10,662
Change in fair value of real estate investments included in net income (loss)	0	0	0	0
Ending balance	10,662	10,662	10,662	10,662
Unrealized gains recognized in net (loss) income on real estate investments held at end of period	0	0	0	0
Total assets	15,297	12,745	15,297	12,745	$ 14,786
Warrant liability:
Beginning balance	317	0	0	0
Issuance of warrants	0	0	361	0
Change in fair value of warrant liability included in net (loss) income	(10)	0	(54)	0
Ending balance - liabilities	307	0	307	0
Unrealized gains recognized in net (loss) income on warrant liability held at end of period	$ (10)	$ 0	$ (54)	$ 0

XML

Debt (Tables)

6 Months Ended

Jun. 30, 2019

Debt Disclosure [Abstract]

Schedule of Carrying Values and Estimated Fair Values of Debt Instruments

Debt consists of the following instruments at June 30, 2019 and December 31, 2018:

(in thousands)	June 30, 2019						December 31, 2018
	Principal		Carrying Value		Fair Value		Principal		Carrying Value		Fair Value
Bank loans:
PWSC Loan	$	2,717	$	2,717	$	2,656	$	3,917	$	3,917	$	3,829
KWH Loan	9,875		8,957		12,246		—		—		—
	12,592		11,674		14,902		3,917		3,917		3,829
Notes payable:
Mortgage	171,551		180,484		181,042		173,155		182,548		174,265
Flower Note	7,555		7,555		8,322		7,768		7,768		8,565
Net Lease Note	9,000		9,000		9,151		9,000		9,000		9,409
	188,106		197,039		198,515		189,923		199,316		192,239
Subordinated debt	90,500		50,224		50,224		90,500		50,023		50,023
Total	$	291,198	$	258,937	$	263,641	$	284,340	$	253,256	$	246,091

Schedule of Subordinated Debt

Subordinated debt consists of the following trust preferred debt instruments:

Issuer	Principal (in thousands)		Issue date	Interest	Redemption date
Kingsway CT Statutory Trust I	$	15,000	12/4/2002	annual interest rate equal to LIBOR, plus 4.00% payable quarterly	12/4/2032
Kingsway CT Statutory Trust II	$	17,500	5/15/2003	annual interest rate equal to LIBOR, plus 4.10% payable quarterly	5/15/2033
Kingsway CT Statutory Trust III	$	20,000	10/29/2003	annual interest rate equal to LIBOR, plus 3.95% payable quarterly	10/29/2033
Kingsway DE Statutory Trust III	$	15,000	5/22/2003	annual interest rate equal to LIBOR, plus 4.20% payable quarterly	5/22/2033
Kingsway DE Statutory Trust IV	$	10,000	9/30/2003	annual interest rate equal to LIBOR, plus 3.85% payable quarterly	9/30/2033
Kingsway DE Statutory Trust VI	$	13,000	12/16/2003	annual interest rate equal to LIBOR, plus 4.00% payable quarterly	1/8/2034

XML

Earnings From Continuing Operations Per Share (Tables)

6 Months Ended

Jun. 30, 2019

Earnings Per Share [Abstract]

Schedule of Earnings Per Share

The following table sets forth the reconciliation of numerators and denominators for the basic and diluted (loss) earnings from continuing operations per share computation for the three and six months ended June 30, 2019 and June 30, 2018:

(in thousands, except per share data)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Numerator:
(Loss) income from continuing operations	$	(396	)	$	(4,262	)	$	2,793		$	(6,866	)
Less: net income attributable to noncontrolling interests	(258		)	(158		)	(469		)	(517		)
Less: dividends on preferred stock, net of tax	(252		)	(259		)	(498		)	(512		)
(Loss) income from continuing operations attributable to common shareholders	$	(906	)	$	(4,679	)	$	1,826		$	(7,895	)
Denominator:
Weighted average basic shares
Weighted average common shares outstanding	21,867			21,708			21,854			21,708
Weighted average diluted shares
Weighted average common shares outstanding	21,867			21,708			21,854			21,708
Effect of potentially dilutive securities
Stock options	—			—			—			—
Unvested restricted stock awards	—			—			—			—
Unvested restricted stock units	—			—			—			—
Warrants	—			—			—			—
Convertible preferred stock	—			—			—			—
Total weighted average diluted shares	21,867			21,708			21,854			21,708
Basic (loss) earnings from continuing operations per share	$	(0.04	)	$	(0.22	)	$	0.08		$	(0.36	)
Diluted (loss) earnings from continuing operations per share	$	(0.04	)	$	(0.22	)	$	0.08		$	(0.36	)

XML

Earnings From Continuing Operations Per Share

6 Months Ended

Jun. 30, 2019

Earnings Per Share [Abstract]

(LOSS) EARNINGS FROM CONTINUING OPERATIONS PER SHARE

(LOSS) EARNINGS FROM CONTINUING OPERATIONS PER SHARE

The following table sets forth the reconciliation of numerators and denominators for the basic and diluted (loss) earnings from continuing operations per share computation for the three and six months ended June 30, 2019 and June 30, 2018:

(in thousands, except per share data)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Numerator:
(Loss) income from continuing operations	$	(396	)	$	(4,262	)	$	2,793		$	(6,866	)
Less: net income attributable to noncontrolling interests	(258		)	(158		)	(469		)	(517		)
Less: dividends on preferred stock, net of tax	(252		)	(259		)	(498		)	(512		)
(Loss) income from continuing operations attributable to common shareholders	$	(906	)	$	(4,679	)	$	1,826		$	(7,895	)
Denominator:
Weighted average basic shares
Weighted average common shares outstanding	21,867			21,708			21,854			21,708
Weighted average diluted shares
Weighted average common shares outstanding	21,867			21,708			21,854			21,708
Effect of potentially dilutive securities
Stock options	—			—			—			—
Unvested restricted stock awards	—			—			—			—
Unvested restricted stock units	—			—			—			—
Warrants	—			—			—			—
Convertible preferred stock	—			—			—			—
Total weighted average diluted shares	21,867			21,708			21,854			21,708
Basic (loss) earnings from continuing operations per share	$	(0.04	)	$	(0.22	)	$	0.08		$	(0.36	)
Diluted (loss) earnings from continuing operations per share	$	(0.04	)	$	(0.22	)	$	0.08		$	(0.36	)

Basic (loss) earnings from continuing operations per share is calculated using weighted-average common shares outstanding. Diluted (loss) earnings from continuing operations per share is calculated using weighted-average diluted shares. Weighted-average diluted shares is calculated by adding the effect of potentially dilutive securities to weighted-average common shares outstanding. Potentially dilutive securities consist of stock options, unvested restricted stock awards, unvested restricted stock units, warrants and convertible preferred stock. Because the Company is reporting a loss from continuing operations for the three months ended June 30, 2019 and June 30, 2018 and the six months ended June 30, 2018, all potentially dilutive securities outstanding were excluded from the calculation of diluted loss from continuing operations per share since their inclusion would have been anti-dilutive.

XML

Debt

6 Months Ended

Jun. 30, 2019

Debt Disclosure [Abstract]

DEBT

DEBT

Debt consists of the following instruments at June 30, 2019 and December 31, 2018:

(in thousands)	June 30, 2019						December 31, 2018
	Principal		Carrying Value		Fair Value		Principal		Carrying Value		Fair Value
Bank loans:
PWSC Loan	$	2,717	$	2,717	$	2,656	$	3,917	$	3,917	$	3,829
KWH Loan	9,875		8,957		12,246		—		—		—
	12,592		11,674		14,902		3,917		3,917		3,829
Notes payable:
Mortgage	171,551		180,484		181,042		173,155		182,548		174,265
Flower Note	7,555		7,555		8,322		7,768		7,768		8,565
Net Lease Note	9,000		9,000		9,151		9,000		9,000		9,409
	188,106		197,039		198,515		189,923		199,316		192,239
Subordinated debt	90,500		50,224		50,224		90,500		50,023		50,023
Total	$	291,198	$	258,937	$	263,641	$	284,340	$	253,256	$	246,091

(a)          Bank loans:

As part of the acquisition of PWSC on October 12, 2017, the Company borrowed a principal amount of $5.0 million from a bank at a fixed interest rate of 5.0% (the "PWSC Loan"). The carrying value of the PWSC Loan represents its unpaid principal balance. The fair value of the PWSC Loan disclosed in the table above is derived from quoted market prices of B and B minus rated industrial bonds with similar maturities. The PWSC Loan was scheduled to mature on October 12, 2022; however, the principal totaling $0.3 million was fully repaid on January 30, 2020.

As part of the acquisition of Geminus on March 1, 2019, the Company formed Kingsway Warranty Holdings LLC ("KWH") and contributed IWS and Trinity to KWH, which then borrowed a principal amount of $10.0 million from a bank at an annual interest rate equal to LIBOR plus 9.25% (the "KWH Loan"), using most of the proceeds to acquire Geminus. The KWH Loan matures on March 1, 2024. As part of the KWH Loan, KWH also issued warrants (the "KWH Warrants") to the lender exercisable to purchase an aggregate 1.25% membership interest in KWH. The Company allocated $0.4 million of the KWH loan proceeds to a liability, recorded as part of accrued expenses and other liabilities in the consolidated balance sheets, to reflect the estimated fair value of the KWH Warrants, as the warrants contain a put right exercisable by the holder. Changes in the estimated fair value of the KWH Warrants are recorded in the consolidated statements of operations. The Company also recorded as a discount to the carrying value of the KWH Loan issuance costs of $1.0 million specifically related to the KWH Loan. The KWH Loan is carried in the consolidated balance sheets at its amortized cost, which reflects the quarterly pay-down of principal as well as the amortization of the discount using the effective interest rate method. The fair value of the KWH Loan disclosed in the table above is derived from quoted market prices of B and BB minus rated industrial bonds with similar maturities. The KWH Loan is secured by certain of the equity interests and assets of KWH and its subsidiaries.

(b)          Notes payable:

As part of the acquisition of CMC Industries, Inc. ("CMC") in July 2016, the Company assumed a mortgage, which is recorded as note payable in the consolidated balance sheets ("the Mortgage"). The Mortgage is nonrecourse indebtedness with respect to CMC and its subsidiaries, and the Mortgage is not, nor will it be, guaranteed by Kingsway or its affiliates. The Mortgage was recorded at its estimated fair value of $191.7 million, which included the unpaid principal amount of $180.0 million as of the date of acquisition plus a premium of $11.7 million. The Mortgage matures on May 15, 2034 and has a fixed interest rate of 4.07%. The Mortgage is carried in the consolidated balance sheets at its amortized cost, which reflects the monthly pay-down of principal as well as the amortization of the premium using the effective interest rate method. The fair value of the Mortgage disclosed in the table above is derived from quoted market prices of A-rated industrial bonds with similar maturities.

On January 5, 2015, Flower Portfolio 001, LLC ("Flower") assumed a $9.2 million mortgage in conjunction with the purchase of investment real estate properties, which is recorded as note payable in the consolidated balance sheets ("the Flower Note"). The Flower Note requires monthly payments of principal and interest and is secured by certain investments of Flower. The Flower Note matures on December 10, 2031 and has a fixed interest rate of 4.81%. The carrying value of the Flower Note at June 30, 2019 of $7.6 million represents its unpaid principal balance. The fair value of the Flower Note disclosed in the table above is derived from quoted market prices of A and B rated industrial bonds with similar maturities.

On October 15, 2015, Net Lease assumed a $9.0 million mezzanine debt in conjunction with the purchase of investment real estate properties, which is recorded as note payable in the consolidated balance sheets ("the Net Lease Note"). The Net Lease Note requires monthly payments of interest and is secured by certain investments of Net Lease. The Net Lease Note matures on November 1, 2020 and has a fixed interest rate of 10.25%. The carrying value of the Net Lease Note at June 30, 2019 of $9.0 million represents its unpaid principal balance. The fair value of the Net Lease Note disclosed in the table above is derived from quoted market prices of B and B minus rated industrial bonds with similar maturities.

(c)          Subordinated debt:

The subordinated debt is carried in the consolidated balance sheets at fair value. See Note 21, "Fair Value of Financial Instruments," for further discussion of the subordinated debt. Of the $0.2 million increase in fair value of the Company’s subordinated debt between December 31, 2018 and June 30, 2019, $1.7 million is reported as change in fair value of debt attributable to instrument-specific credit risk in the Company's consolidated statements of comprehensive (loss) income, partially offset by $1.5 million reported as gain on change in fair value of debt in the Company’s consolidated statements of operations.

During the third quarter of 2018, the Company gave notice to its Trust Preferred trustees of its intention to exercise its voluntary right to defer interest payments for up to 20 quarters, pursuant to the contractual terms of its outstanding Trust Preferred indentures, which permit interest deferral. This action does not constitute a default under the Company's Trust Preferred indentures or any of its other debt indentures. At June 30, 2019, deferred interest payable of $5.7 million is included in accrued expenses and other liabilities in the consolidated balance sheets.

Subordinated debt consists of the following trust preferred debt instruments:

Issuer	Principal (in thousands)		Issue date	Interest	Redemption date
Kingsway CT Statutory Trust I	$	15,000	12/4/2002	annual interest rate equal to LIBOR, plus 4.00% payable quarterly	12/4/2032
Kingsway CT Statutory Trust II	$	17,500	5/15/2003	annual interest rate equal to LIBOR, plus 4.10% payable quarterly	5/15/2033
Kingsway CT Statutory Trust III	$	20,000	10/29/2003	annual interest rate equal to LIBOR, plus 3.95% payable quarterly	10/29/2033
Kingsway DE Statutory Trust III	$	15,000	5/22/2003	annual interest rate equal to LIBOR, plus 4.20% payable quarterly	5/22/2033
Kingsway DE Statutory Trust IV	$	10,000	9/30/2003	annual interest rate equal to LIBOR, plus 3.85% payable quarterly	9/30/2033
Kingsway DE Statutory Trust VI	$	13,000	12/16/2003	annual interest rate equal to LIBOR, plus 4.00% payable quarterly	1/8/2034

XML

Subsequent Event (Notes)

6 Months Ended

Jun. 30, 2019

Subsequent Events [Abstract]

SUBSEQUENT EVENT

SUBSEQUENT EVENT

In March 2020, the outbreak of COVID-19 caused by a novel strain of the coronavirus was recognized as a pandemic by the World Health Organization, and the outbreak has become increasingly widespread in the United States, including in the markets in which we operate. The COVID-19 outbreak has had a notable impact on general economic conditions, including but not limited to the temporary closures of many businesses; "shelter in place" and other governmental regulations; and reduced consumer pending due to both job losses and other effects attributable to COVID-19. The near-term impacts of COVID-19 are primarily with respect to the Company’s Extended Warranty segment. As consumer spending has been impacted, including a decline in the purchase of new and used vehicles, and many businesses through which the Company distributes its products remain closed, the Company has seen cash flows being affected by a reduction in new warranty sales for vehicle service agreements. With respect to homeowner warranties, the Company expects to see a reduction in new enrollments in its home warranty programs associated with the impact of COVID-19 on new home sales in the United States. There remain many unknowns and the Company continues to monitor the expected trends and related demand for its services and has and will continue to adjust its operations accordingly.

The Company could experience other potential impacts as a result of COVID-19, including, but not limited to, potential impairment charges to the carrying amounts of goodwill, indefinite-lived intangibles and long-lived assets. Actual results may differ materially from the Company’s current estimates as the scope of COVID-19 evolves or if the duration of business disruptions is longer than initially anticipated.

XML

Investment in Investee (Tables)

6 Months Ended

Jun. 30, 2019

Equity Method Investments and Joint Ventures [Abstract]

Carrying Value, Estimated Fair Value and Equity Percentage in Investment in Investee

The carrying value, estimated fair value and approximate equity percentage for the Company's investment in investee at June 30, 2019 and December 31, 2018 were as follows:

(in thousands, except for percentages)
	June 30, 2019						December 31, 2018
	Equity Percentage		Estimated Fair Value		Carrying Value		Equity Percentage		Estimated Fair Value		Carrying Value
ICL	22.9	%	$	1,542	$	1,119	22.9	%	$	951	$	951

XML

Acquisition and Discontinued Operations

6 Months Ended

Jun. 30, 2019

Business Combinations [Abstract]

ACQUISITION AND DISCONTINUED OPERATIONS

ACQUISITION AND DISCONTINUED OPERATIONS

(a)     Acquisition

Geminus Holdings Company, Inc.:

On March 1, 2019, the Company acquired 100% of the outstanding shares of Geminus Holding Company, Inc. ("Geminus") for total consideration of $8.4 million, comprised of $7.7 million of cash and an installment payable to the seller of $0.7 million due February 15, 2020. The payable to seller was paid in full by February 15, 2020. At June 30, 2019, the balance of the payable to seller was $0.2 million. As further discussed in Note 20, "Segmented Information," Geminus is included in the Extended Warranty segment. Geminus is a specialty, full-service provider of vehicle service agreements and other finance and insurance products to used car buyers around the country. Geminus, headquartered in Wilkes-Barre, Pennsylvania, has been creating, marketing and administering these products on high-mileage used cars through its subsidiaries, The Penn Warranty Corporation ("Penn") and Prime Auto Care, Inc. ("Prime"), since 1988. Penn and Prime distribute these products via independent used car dealerships and franchised car dealerships, respectively. This acquisition allows the Company to grow its portfolio of warranty companies and further expand into the vehicle service agreement business.

This acquisition was accounted for as a business combination using the acquisition method of accounting. The purchase price was allocated to the assets acquired and liabilities assumed based upon their estimated fair values at the date of acquisition. Goodwill of $7.4 million was recognized, and $5.7 million of separately identifiable intangible assets were recognized resulting from the valuations of acquired customer relationships and trade names. Refer to Note 9, "Intangible Assets," for further disclosure of the intangible assets related to this acquisition. The goodwill represents the premium paid over the fair value of the net tangible and intangible assets acquired, which the Company paid to grow its portfolio of warranty companies and acquire an assembled workforce. The goodwill is not deductible for tax purposes. During the three months ended June 30, 2019 and June 30, 2018, the Company incurred acquisition-related expenses of zero and $0.0 million, respectively, ($0.0 million year to date compared to $0.0 million prior year to date), which are included in general and administrative expensesin the consolidated statements of operations.

The following table summarizes the estimated fair values of the assets acquired and liabilities assumed at the date of acquisition:

(in thousands)
	March 1, 2019
Investments	$	4,405
Cash and cash equivalents	755
Restricted cash	2,650
Accrued investment income	32
Service fee receivable	513
Other receivables	12
Property and equipment, net	79
Goodwill	7,445
Intangible assets not subject to amortization - trade names	1,974
Intangible asset subject to amortization - customer relationships	3,732
Other assets	620
Total assets	$	22,217
Accrued expenses and other liabilities	$	2,018
Income taxes payable	1
Deferred service fees	10,564
Net deferred income tax liabilities	1,263
Total liabilities	$	13,846
Purchase price	$	8,371

The consolidated statements of operations include the earnings of Geminus from the date of acquisition. From the date of acquisition through June 30, 2019, Geminus earned revenue of $3.7 million and net income of $0.6 million. The following unaudited pro forma summary presents the Company's consolidated financial statements for the three and six months ended June 30, 2019 and June 30, 2018 as if Geminus had been acquired on January 1, 2018. The pro forma summary is presented for illustrative purposes only and does not purport to represent the results of our operations that would have actually occurred had the acquisition occurred on January 1, 2018 or project our results of operations as of any future date or for any future period, as applicable.

(in thousands, except per share data)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019		2018
Revenues	$	15,226		$	15,218		$	30,491	$	30,982
(Loss) income from continuing operations attributable to common shareholders	$	(906	)	$	(5,357	)	$	676	$	(8,874	)
Basic (loss) earnings per share - continuing operations	$	(0.04	)	$	(0.25	)	$	0.03	$	(0.41	)
Diluted (loss) earnings per share - continuing operations	$	(0.04	)	$	(0.25	)	$	0.03	$	(0.41	)

(b)     Discontinued Operations

Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company:

On July 16, 2018, the Company announced it had entered into a definitive agreement to sell its non-standard automobile insurance companies Mendota Insurance Company, Mendakota Insurance Company and Mendakota Casualty Company (collectively "Mendota"). On October 18, 2018, the Company completed the previously announced sale of Mendota. As a result of this announcement, Mendota, which was previously disclosed as part of the Insurance Underwriting segment, has been classified as a discontinued operation, and the results of their operations are reported separately for all periods presented. The Company recognized a loss on disposal of Mendota of $8.0 million in the second quarter of 2018 as a result of adjusting the net carrying value of Mendota to be equal to the estimated purchase price. For the year ended December 31, 2018, the Company recognized a loss on disposal of Mendota of $8.5 million.

The final aggregate purchase price of $28.6 million was redeployed primarily to acquire equity investments, limited liability investments, limited liability investment, at fair value and other investments, which were owned by Mendota at the time of the closing, and to fund $5.0 million into an escrow account to be used to satisfy potential indemnity obligations under the definitive stock purchase agreement. As part of the transaction, the Company will indemnify the buyer for any loss and loss adjustment expenses with respect to open claims and certain specified claims in excess of Mendota's carried unpaid loss and loss adjustment expenses at June 30, 2018. The maximum obligation to the Company with respect to the open claims is $2.5 million. There is no maximum obligation to the Company with respect to the specified claims. During the first quarter of 2019, Mendota settled one of the two specified claims for $0.5 million, resulting in no loss to the Company. During the fourth quarter of 2019, Mendota notified the Company that Mendota had entered into an agreement to settle the remaining specified claim. The Company estimates it will incur a net loss of approximately $1.6 million related to the settlement of the remaining specified claim, which the Company will report in its consolidated statement of operations for the year ended December 31, 2019. The $1.6 million settlement was funded from the $5.0 million escrow account, and the $3.4 million remaining in the escrow account was released to the Company during the first quarter of 2020 consistent with the terms of the escrow agreement.

Assigned Risk Solutions Ltd:

On April 1, 2015, the Company closed on the sale of its subsidiary, Assigned Risk Solutions Ltd. ("ARS").  The terms of the sale provided for receipt by the Company of future earnout payments equal to 1.25% of ARS' written premium and fee income during the earnout periods. The earnout payments were payable in three annual installments beginning in April 2016 through April 2018. During the second quarter of 2018, the Company received cash consideration, before expenses, of $1.7 million for the third annual installment earnout payment. Net of expenses, the Company recorded an additional gain on disposal of ARS of $1.3 million for the three and six months ended June 30, 2018, respectively. As a result of the sale, ARS, previously disclosed as part of the Extended Warranty segment, has been classified as a discontinued operation.

Summary financial information for Mendota and ARS included in income from discontinued operations, net of taxes in the statements of operations for the three and six months ended June 30, 2018 is presented below:

(in thousands)	Three months ended June 30,			Six months ended June 30,
	2018			2018
Income (loss) from discontinued operations, net of taxes:
Revenues:
Net premiums earned	$	22,956		$	51,592
Total revenues	22,956			51,592
Other revenues (expenses), net:
Loss and loss adjustment expenses	(18,927		)	(41,728		)
Commissions and premium taxes	(2,225		)	(6,388		)
General and administrative expenses	(3,825		)	(7,778		)
Net investment income	208			434
Net realized losses	(134		)	(134		)
Gain on change in fair value of equity investments	96			106
Other income	2,445			4,876
Total other revenue (expenses), net	(22,362		)	(50,612		)
Income from discontinued operations before income tax benefit	594			980
Income tax benefit	—			—
Income from discontinued operations, net of taxes	594			980
Loss on disposal of discontinued operations before income tax expense	(6,628		)	(6,628		)
Income tax expense	—			—
Loss on disposal of discontinued operations, net of taxes	(6,628		)	(6,628		)
Total loss from discontinued operations, net of taxes	$	(6,034	)	$	(5,648	)

XML

Business

6 Months Ended

Jun. 30, 2019

Business [Abstract]

BUSINESS

BUSINESS

Kingsway Financial Services Inc. (the "Company" or "Kingsway") was incorporated under the Business Corporations Act (Ontario) on September 19, 1989. Effective December 31, 2018, the Company changed its jurisdiction of incorporation from the province of Ontario, Canada, to the State of Delaware. Kingsway is a holding company with operating subsidiaries located in the United States. The Company owns or controls subsidiaries primarily in the extended warranty, asset management and real estate industries.

XML

Intangible Assets

6 Months Ended

Jun. 30, 2019

Goodwill and Intangible Assets Disclosure [Abstract]

INTANGIBLE ASSETS

9 INTANGIBLE ASSETS

Intangible assets at June 30, 2019 and December 31, 2018 are comprised as follows:

(in thousands)			June 30, 2019
	Gross Carrying Value			Accumulated Amortization		Net Carrying Value
Intangible assets subject to amortization:
Database	$	4,918		$	3,259	$	1,659
Vehicle service agreements in-force	3,680			3,675		5
Customer relationships	12,646			4,580		8,066
In-place lease	1,125			186		939
Non-compete	266			91		175
Intangible assets not subject to amortization:
Tenant relationship	73,667			—		73,667
Trade names	3,264			—		3,264
Total	$	99,566		$	11,791	$	87,775

(in thousands)			December 31, 2018
	Gross Carrying Value			Accumulated Amortization		Net Carrying Value
Intangible assets subject to amortization:
Database	$	4,918		$	3,013	$	1,905
Vehicle service agreements in-force	3,680			3,671		9
Customer relationships	8,914			3,691		5,223
In-place lease	1,125			155		970
Non-compete	266			64		202
Intangible assets not subject to amortization:
Tenant relationship	73,667			—		73,667
Trade names	1,290			—		1,290
Total	$	93,860		$	10,594	$	83,266

As further discussed in Note 5, "Acquisition and Discontinued Operations," during the first quarter of 2019, the Company recorded $5.7 million of separately identifiable intangible assets, related to acquired customer relationships and trade names, as part of the acquisition of Geminus. The customer relationships intangible asset of $3.7 million is being amortized over ten years based on the pattern in which the economic benefits of the intangible asset are expected to be consumed. The trade name intangible assets of $2.0 million are deemed to have indefinite useful lives and are not amortized.

The Company's other intangible assets with definite useful lives are amortized either based on the patterns in which the economic benefits of the intangible assets are expected to be consumed or using the straight-line method over their estimated useful lives, which range from seven to eighteen years. Amortization of intangible assets was $0.7 million and $0.3 million for the three months ended June 30, 2019 and June 30, 2018, respectively ($1.2 million and $0.5 million for the six months ended June 30, 2019 and June 30, 2018, respectively).

The tenant relationship and trade name intangible assets have indefinite useful lives and are not amortized. No impairment charges were taken on intangible assets during the three and six months ended June 30, 2019 and June 30, 2018.

XML

Stock-Based Compensation - Stock Option Activity (Details) - USD ($)	6 Months Ended	12 Months Ended
	Jun. 30, 2019	Dec. 31, 2018
Number of Options Outstanding
Outstanding, Beginning of Period (in shares)	40,000
Granted (in shares)	0
Expired (in shares)	0
Outstanding, End of Period (in shares)	40,000	40,000
Exercisable (in shares)	40,000
Weighted-Average Exercise Price
Outstanding, Beginning of Period (in dollars per share)	$ 4.67
Granted (in dollars per share)	0.00
Expired (in dollars per share)	0.00
Outstanding, End of Period (in dollars per share)	4.67	$ 4.67
Exercisable (in dollars per share)	$ 4.67
Weighted-Average Remaining Contractual Term (in Years)
Outstanding	9 months 18 days	1 year 3 months 18 days
Exercisable at June 30, 2019	9 months 18 days
Aggregate Intrinsic Value (in Thousands)
Outstanding	$ 0	$ 0
Exercisable at June 30, 2019	$ 0

XML

Leases - Narrative (Details)	3 Months Ended		6 Months Ended
	Jun. 30, 2019 USD ($) a	Jun. 30, 2018 USD ($)	Jun. 30, 2019 USD ($) a	Jun. 30, 2018 USD ($)
Leases [Abstract]
Operating lease cost	$ 200,000		$ 500,000
Variable lease cost	$ 0		$ 0
Weighted average remaining lease term	6 years 4 months 24 days		6 years 4 months 24 days
Weighted average discount rate	5.69%		5.69%
Cash paid for amounts included in lease liabilities			$ 500,000
Land subject to ground leases | a	192		192
Below market lease liabilities, 2019	$ 100,000		$ 100,000
Below market lease liabilities, 2020	100,000		100,000
Below market lease liabilities, 2021	100,000		100,000
Below market lease liabilities, 2022	100,000		100,000
Below market lease liabilities, 2023	100,000		100,000
Lease income	$ 3,341,000	$ 3,345,000	$ 6,682,000	$ 6,693,000

XML

Leases - Net Book Value of Operating Lease Property (Details) - USD ($) $ in Thousands	Jun. 30, 2019	Dec. 31, 2018
Leases [Abstract]
Property leased to lessees	$ 113,008	$ 113,008
Accumulation depreciation	(12,271)	(10,197)
Net property and equipment leased	$ 100,737	$ 102,811

XML

Related Parties - Logistics Leasing, LLC (Details) - Equity Method Investee	Jun. 30, 2019	Dec. 31, 2018	Jul. 26, 2017	Sep. 21, 2015
Related Party Transaction [Line Items]
Ownership interest acquired			50.00%
Equity method investment, ownership percentage	47.60%	47.60%	51.00%	33.30%

XML

Vehicle Service Agreement Liability Vehicle Service Agreement Liability - Narrative (Details)	Mar. 31, 2019
Minimum
Product Warranty Liability [Line Items]
Vehicle service agreement fee, percentage of refund on original amount	9.00%
Maximum
Product Warranty Liability [Line Items]
Vehicle service agreement fee, percentage of refund on original amount	13.00%

XML

Debt - Carrying Value of Debt Instruments (Details) - USD ($) $ in Thousands	Jun. 30, 2019	Dec. 31, 2018	Jul. 31, 2016
Debt Instrument [Line Items]
Principal	$ 291,198	$ 284,340
Carrying Value	258,937	253,256
Fair Value	263,641	246,091
Bank loans
Debt Instrument [Line Items]
Principal	12,592	3,917
Carrying Value	11,674	3,917
Fair Value	14,902	3,829
Bank loans | PWSC Loan
Debt Instrument [Line Items]
Principal	2,717	3,917
Carrying Value	2,717	3,917
Fair Value	2,656	3,829
Bank loans | KWH Loan
Debt Instrument [Line Items]
Principal	9,875	0
Carrying Value	8,957	0
Fair Value	12,246	0
Note payable
Debt Instrument [Line Items]
Principal	188,106	189,923
Carrying Value	197,039	199,316
Fair Value	198,515	192,239
Note payable | Flower Note
Debt Instrument [Line Items]
Principal	7,555	7,768
Carrying Value	7,555	7,768
Fair Value	8,322	8,565
Note payable | Net Lease Note
Debt Instrument [Line Items]
Principal	9,000	9,000
Carrying Value	9,000	9,000
Fair Value	9,151	9,409
Mortgage
Debt Instrument [Line Items]
Principal	171,551	173,155
Carrying Value	180,484	182,548
Fair Value	181,042	174,265	$ 191,700
Subordinated debt
Debt Instrument [Line Items]
Principal	90,500	90,500
Carrying Value	50,224	50,023
Fair Value	$ 50,224	$ 50,023

XML

Revenue from Contracts with Customers - Performance Obligations (Details) $ in Millions	6 Months Ended
	Jun. 30, 2019 USD ($)
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction [Line Items]
Service fee and commission income recognized during the period	$ 7.9
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction, Start Date [Axis]: 2019-07-01
Revenue, Remaining Performance Obligation, Expected Timing of Satisfaction [Line Items]
Remaining performance obligation, expected timing of satisfaction, period	1 year
Performance obligation satisfied	40.50%

XML

- Other Related Party Transactions (Details) - USD ($)			3 Months Ended		6 Months Ended
	Feb. 28, 2020	Sep. 05, 2018	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Related Party Transaction [Line Items]
Other income			$ 113,000	$ 108,000	$ 258,000	$ 321,000
Swets | Affiliated Entity
Related Party Transaction [Line Items]
Advisor agreement period		1 year
Other income		$ 300,000
Subsequent Event | Chief Financial Officer
Related Party Transaction [Line Items]
Consulting agreement, fee	$ 100,000
Consulting agreement, hourly fee	$ 165

XML

Consolidated Statements of Shareholders' Equity - USD ($) $ in Thousands	Total	Shareholders' Equity Attributable to Common Shareholders	Common Stock	Additional Paid-in Capital	Accumulated Deficit	Accumulated Other Comprehensive Income (Loss)	Noncontrolling Interests in Consolidated Subsidiaries
Balance, beginning of period (in shares) at Dec. 31, 2017			21,708,190
Balance, beginning of period at Dec. 31, 2017	$ 50,727	$ 41,366	$ 0	$ 356,171	$ (310,953)	$ (3,852)	$ 9,361
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net (loss) income	(12,514)	(13,031)			(13,031)		517
Contributions from noncontrolling interest holders	425						425
Preferred stock dividends	(512)	(512)		(512)
Other comprehensive (loss) income	(104)	(97)				(97)	(7)
Stock-based compensation	588	588		588
Balance, end of period (in shares) at Jun. 30, 2018			21,708,190.00
Balance, end of period at Jun. 30, 2018	37,956	27,667	$ 0	356,247	(365,126)	36,546	10,289
Balance, beginning of period (in shares) at Mar. 31, 2018			21,708,190
Balance, beginning of period at Mar. 31, 2018	47,514	37,383	$ 0	356,211	(354,672)	35,844	10,131
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net (loss) income	(10,296)	(10,454)			(10,454)		158
Preferred stock dividends	(259)	(259)		(259)
Other comprehensive (loss) income	702	702				702	0
Stock-based compensation	295	295		295
Balance, end of period (in shares) at Jun. 30, 2018			21,708,190.00
Balance, end of period at Jun. 30, 2018	$ 37,956	27,667	$ 0	356,247	(365,126)	36,546	10,289
Balance, beginning of period (in shares) at Dec. 31, 2018	21,787,728		21,787,728
Balance, beginning of period at Dec. 31, 2018	$ 24,258	12,462	$ 0	353,890	(382,196)	40,768	11,796
Balance, end of period (in shares) at Mar. 31, 2019			21,866,959
Balance, end of period at Mar. 31, 2019	$ 26,603	14,590	$ 0	353,886	(379,218)	39,922	12,013
Balance, beginning of period (in shares) at Dec. 31, 2018	21,787,728		21,787,728
Balance, beginning of period at Dec. 31, 2018	$ 24,258	12,462	$ 0	353,890	(382,196)	40,768	11,796
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Vesting of restricted stock awards, net of share settlements for tax withholdings (in shares)			79,231
Net (loss) income	2,793	2,324			2,324		469
Preferred stock dividends	(498)	(498)		(498)
Deconsolidation of noncontrolling interest	(301)						(301)
Other comprehensive (loss) income	(1,431)	(1,443)				(1,443)	12
Stock-based compensation	$ 386	386		386
Balance, end of period (in shares) at Jun. 30, 2019	21,866,959		21,866,959
Balance, end of period at Jun. 30, 2019	$ 25,207	13,231	$ 0	353,778	(379,872)	39,325	11,976
Balance, beginning of period (in shares) at Mar. 31, 2019			21,866,959
Balance, beginning of period at Mar. 31, 2019	26,603	14,590	$ 0	353,886	(379,218)	39,922	12,013
Increase (Decrease) in Stockholders' Equity [Roll Forward]
Net (loss) income	(396)	(654)			(654)		258
Preferred stock dividends	(252)	(252)		(252)
Deconsolidation of noncontrolling interest	(301)						(301)
Other comprehensive (loss) income	(591)	(597)				(597)	6
Stock-based compensation	$ 144	144		144
Balance, end of period (in shares) at Jun. 30, 2019	21,866,959		21,866,959
Balance, end of period at Jun. 30, 2019	$ 25,207	$ 13,231	$ 0	$ 353,778	$ (379,872)	$ 39,325	$ 11,976

XML

Consolidated Balance Sheets (Parenthetical) - USD ($) $ in Thousands	Jun. 30, 2019	Dec. 31, 2018
Assets
Fixed maturities, cost	$ 20,771	$ 12,432
Equity investments, cost	1,506	2,274
Real estate investments, cost	10,225	10,225
Premiums receivable, allowance for doubtful accounts	0	0
Other receivables, allowance for doubtful accounts	324	191
Service fee receivable, allowance for doubtful accounts	201	184
Property and equipment, accumulated depreciation	18,310	15,958
Intangible assets, accumulated amortization	$ 11,791	$ 10,594
Liabilities:
Preferred stock authorized (in shares)	1,000,000	1,000,000
Preferred stock issued (in shares)	222,876	222,876
Preferred stock outstanding (in shares)	222,876	222,876
Redemption amount	$ 7,485	$ 7,278
Shareholders' Equity:
Common stock authorized (in shares)	50,000,000
Common stock issued (in shares)	21,866,959	21,787,728
Common stock outstanding (in shares)	21,866,959	21,787,728

XML

Acquisition and Discontinued Operations Acquisition and Discontinued Operations - Pro Forma Information (Details) - USD ($) $ / shares in Units, $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Business Combinations [Abstract]
Revenues	$ 15,226	$ 15,218	$ 30,491	$ 30,982
(Loss) income from continuing operations attributable to common shareholders	$ (906)	$ (5,357)	$ 676	$ (8,874)
Basic (loss) earnings per share - continuing operations (in dollars per share)	$ (0.04)	$ (0.25)	$ 0.03	$ (0.41)
Diluted (loss) earnings per share - continuing operations (in dollars per share)	$ (0.04)	$ (0.25)	$ 0.03	$ (0.41)

XML

Summary of Significant Accounting Policies Summary of Significant Accounting Policies (Details) $ in Thousands			3 Months Ended
	Mar. 31, 2021 USD ($)	Mar. 31, 2020 USD ($) shares	Sep. 30, 2018 subsidiary_trust	Jun. 30, 2019 USD ($) shares	Dec. 31, 2018 USD ($) shares
Temporary Equity [Line Items]
Interest payments deferral period			5 years
Number of subsidiary trusts | subsidiary_trust			6
Cash				$ 1,800	$ 1,900
Cash and cash equivalents				$ 10,899	$ 14,619
Preferred stock issued (in shares) | shares				222,876	222,876
Preferred stock outstanding (in shares) | shares				222,876	222,876
Redemption amount				$ 7,485	$ 7,278
Subsequent Event
Temporary Equity [Line Items]
Preferred stock issued (in shares) | shares		182,876
Preferred stock outstanding (in shares) | shares		182,876
Redemption amount		$ 6,700
Interest expense on trust preferred securities	$ 14,900	$ 10,500

XML

Commitment and Contingencies

6 Months Ended

Jun. 30, 2019

Commitments and Contingencies Disclosure [Abstract]

COMMITMENTS AND CONTINGENCIES

COMMITMENTS AND CONTINGENCIES

(a)    Legal proceedings:

In April 2018, TRT LeaseCo, LLC ("TRT LeaseCo"), an indirect subsidiary of Kingsway, was named as a defendant in a lawsuit filed in the United States District Court for the Southern District of New York relating to CMC and its subsidiaries.  Kingsway indirectly owns 81% of CMC.  TRT LeaseCo (an indirect wholly owned subsidiary of CMC) entered into a Management Services Agreement (the "MSA") with DGI-BNSF Corp. ("DGI") (an affiliate of the entity that owns the remaining 19% of CMC) in July 2016 pursuant to which, among other things, DGI agreed to provide services to TRT LeaseCo in exchange for the fees specified in the MSA.  The complaint filed by DGI alleges that DGI is owed certain fees under the MSA that have not been paid.  If the case is decided against TRT LeaseCo, CMC and its subsidiaries (including TRT LeaseCo) would be unable to fulfill certain payment obligations to Kingsway under the transaction documents such that Kingsway may no longer be able to realize a material portion of the economic benefits originally anticipated to result from the CMC transaction, which could have a material adverse effect on Kingsway’s financial position, results of operations and cash flows.  Kingsway disagrees with DGI’s allegations and is vigorously defending these claims; however, there can be no assurance that Kingsway will ultimately prevail. The Company’s potential exposure under these agreements is not reasonably determinable, and no liability has been recorded in the audited consolidated financial statements at June 30, 2019.  No assurances can be given, however, that the Company will not be required to perform under these agreements in a manner that would have a material adverse effect on the Company’s financial position, results of operations and cash flow.

In May 2016, Aegis Security Insurance Company ("Aegis") filed a complaint for breach of contract and declaratory relief against the Company in the Eastern District of Pennsylvania alleging, among other things, that the Company breached a contractual obligation to indemnify Aegis for certain customs bond losses incurred by Aegis under the indemnity and hold harmless agreements provided by the Company to Aegis for certain customs bonds reinsured by Lincoln General Insurance Company ("Lincoln General") during the period of time that Lincoln General was a subsidiary of the Company.  Lincoln General was placed into liquidation in November 2015 and Aegis subsequently invoked its rights to indemnity under the indemnity and hold harmless agreements.  Effective January 20, 2020, Aegis and the Company entered into a Settlement Agreement with respect to such litigation pursuant to which the Company agreed to pay Aegis a one-time settlement amount of $0.9 million, which the Company will report in its consolidated statement of operations for the three months ended March 31, 2020, and to reimburse Aegis for 60% of future losses that Aegis may sustain in connection with such customs bonds, up to a maximum reimbursement amount of $4.8 million. The Company’s potential exposure under these agreements was not reasonably determinable at June 30, 2019, and no liability has been recorded in the audited consolidated financial statements at June 30, 2019.

(b)    Guarantee:

As further discussed in Note 5, "Acquisition and Discontinued Operations," as part of the transaction to sell Mendota, the Company will indemnify the buyer for loss and loss adjustment expenses with respect to open claims and certain specified claims in excess of Mendota's carried unpaid loss and loss adjustment expenses at June 30, 2018 related to the open claims and specified claims. The Company's potential exposure under these agreements was not reasonably determinable at June 30, 2019, and no liability has been recorded in the unaudited consolidated interim financial statements at June 30, 2019.

(c)    Commitments:

The Company has entered into subscription agreements to commit up to $2.6 million of capital to allow for participation in limited liability investments. At June 30, 2019, the unfunded commitment was $0.6 million, all of which related to the Company’s commitment to Argo Holdings. On December 4, 2019, Argo Management informed members of Argo Holdings that no more Capital Calls are planned.

XML

Investments (Tables)

6 Months Ended

Jun. 30, 2019

Investments [Abstract]

Schedule of Unrealized Loss on Investments

The amortized cost, gross unrealized gains and losses, and estimated fair value of the Company's available-for-sale investments at June 30, 2019 and December 31, 2018 are summarized in the tables shown below:

(in thousands)	June 30, 2019
	Amortized Cost		Gross Unrealized Gains		Gross Unrealized Losses		Estimated  Fair Value
Fixed maturities:
U.S. government, government agencies and authorities	$	15,007	$	52	$	13	$	15,046
States, municipalities and political subdivisions	604		1		4		601
Mortgage-backed	2,474		2		22		2,454
Corporate	2,686		9		9		2,686
Total fixed maturities	$	20,771	$	64	$	48	$	20,787

(in thousands)	December 31, 2018
	Amortized Cost		Gross Unrealized Gains		Gross Unrealized Losses		Estimated  Fair Value
Fixed maturities:
U.S. government, government agencies and authorities	$	5,594	$	1	$	48	$	5,547
States, municipalities and political subdivisions	621		—		14		607
Mortgage-backed	3,256		—		70		3,186
Corporate	2,961		—		41		2,920
Total fixed maturities	12,432		1		173		12,260

Investments Classified by Contractual Maturity Date

The table below summarizes the Company's fixed maturities at June 30, 2019 by contractual maturity periods. Actual results may differ as issuers may have the right to call or prepay obligations, with or without penalties, prior to the contractual maturity of these obligations.

(in thousands)	June 30, 2019
	Amortized Cost		Estimated Fair Value
Due in one year or less	$	11,652	$	11,672
Due after one year through five years	7,641		7,650
Due after five years through ten years	194		192
Due after ten years	1,284		1,273
Total	$	20,771	$	20,787

Available-for-sale Securities, Continuous Unrealized Loss Position, Fair Value

The following tables highlight the aggregate unrealized loss position, by security type, of available-for-sale investments in unrealized loss positions as of June 30, 2019 and December 31, 2018. The tables segregate the holdings based on the period of time the investments have been continuously held in unrealized loss positions.

(in thousands)									June 30, 2019
	Less than 12 Months				Greater than 12 Months				Total
	Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss
Fixed maturities:
U.S. government, government agencies and authorities	$	2,497	$	2	$	1,950	$	11	$	4,447	$	13
States, municipalities and political subdivisions	75		—		453		4		528		4
Mortgage-backed	150		—		1,698		22		1,848		22
Corporate	121		—		1,123		9		1,244		9
Total fixed maturities	$	2,843	$	2	$	5,224	$	46	$	8,067	$	48

(in thousands)									December 31, 2018
	Less than 12 Months				Greater than 12 Months				Total
	Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss
Fixed maturities:
U.S. government, government agencies and authorities	$	1,497	$	1	$	2,609	$	47	$	4,106	$	48
States, municipalities and political subdivisions	—		—		606		14		606		14
Mortgage-backed	800		1		2,134		69		2,934		70
Corporate	595		1		2,151		40		2,746		41
Total fixed maturities	$	2,892	$	3	$	7,500	$	170	$	10,392	$	173

Investment Income

Net investment income for the three and six months ended June 30, 2019 and June 30, 2018 is comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Investment income:
Interest from fixed maturities	$	122		$	57		$	195		$	90
Dividends	70			82			128			156
Income from limited liability investments	32			189			14			181
Income from limited liability investments, at fair value	232			482			467			701
Income from real estate investments	200			200			400			400
Other	112			9			290			137
Gross investment income	768			1,019			1,494			1,665
Investment expenses	(19		)	(9		)	(46		)	(17		)
Net investment income	$	749		$	1,010		$	1,448		$	1,648

Schedule of Realized Gain (Loss)

Gross realized gains and losses on available-for-sale investments and limited liability investments for the three and six months ended June 30, 2019 and June 30, 2018 are comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Gross realized gains	$	44		$	133		$	359		$	398
Gross realized losses	(600		)	(1		)	(600		)	(1		)
Net realized (losses) gains	$	(556	)	$	132		$	(241	)	$	397

Schedule of Gain on Change in Fair Value of Equity Investments

(Loss) gain on change in fair value of equity investments for the three and six months ended June 30, 2019 and June 30, 2018 is comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Net (losses) gains recognized on equity investments sold during the period	$	(101	)	$	(10	)	$	(101	)	$	545
Change in unrealized gains (losses) on equity investments held at end of the period	38			(411		)	116			199
(Loss) gain on change in fair value of equity investments	$	(63	)	$	(421	)	$	15		$	744

XML

Property and Equipment

6 Months Ended

Jun. 30, 2019

Property, Plant and Equipment [Abstract]

PROPERTY AND EQUIPMENT

PROPERTY AND EQUIPMENT

Property and equipment at June 30, 2019 and December 31, 2018 are comprised as follows:

(in thousands)					June 30, 2019
	Total Property and Equipment							Property leased to others under operating leases included in property and equipment
	Cost		Accumulated Depreciation			Carrying Value		Cost		Accumulated Depreciation		Carrying Value
Land	$	21,120	$	—		$	21,120	$	21,120	$	—	$	21,120
Site improvements	91,308		12,228			79,080		91,308		12,228		79,080
Buildings	580		43			537		580		43		537
Leasehold improvements	149		103			46		—		—		—
Furniture and equipment	1,042		953			89		—		—		—
Computer hardware	5,289		4,983			306		—		—		—
Total	$	119,488	$	18,310		$	101,178	$	113,008	$	12,271	$	100,737

(in thousands)			December 31, 2018
	Total Property and Equipment							Property leased to others under operating leases included in property and equipment
	Cost			Accumulated Depreciation		Carrying Value		Cost		Accumulated Depreciation		Carrying Value
Land	$	21,120		$	—	$	21,120	$	21,120	$	—	$	21,120
Site improvements	91,308			10,161		81,147		91,308		10,161		81,147
Buildings	580			36		544		580		36		544
Leasehold improvements	104			102		2		—		—		—
Furniture and equipment	993			901		92		—		—		—
Computer hardware	4,995			4,758		237		—		—		—
Total	$	119,100		$	15,958	$	103,142	$	113,008	$	10,197	$	102,811

XML

Investments

6 Months Ended

Jun. 30, 2019

Investments [Abstract]

INVESTMENTS

INVESTMENTS

The amortized cost, gross unrealized gains and losses, and estimated fair value of the Company's available-for-sale investments at June 30, 2019 and December 31, 2018 are summarized in the tables shown below:

(in thousands)	June 30, 2019
	Amortized Cost		Gross Unrealized Gains		Gross Unrealized Losses		Estimated  Fair Value
Fixed maturities:
U.S. government, government agencies and authorities	$	15,007	$	52	$	13	$	15,046
States, municipalities and political subdivisions	604		1		4		601
Mortgage-backed	2,474		2		22		2,454
Corporate	2,686		9		9		2,686
Total fixed maturities	$	20,771	$	64	$	48	$	20,787

(in thousands)	December 31, 2018
	Amortized Cost		Gross Unrealized Gains		Gross Unrealized Losses		Estimated  Fair Value
Fixed maturities:
U.S. government, government agencies and authorities	$	5,594	$	1	$	48	$	5,547
States, municipalities and political subdivisions	621		—		14		607
Mortgage-backed	3,256		—		70		3,186
Corporate	2,961		—		41		2,920
Total fixed maturities	12,432		1		173		12,260

The table below summarizes the Company's fixed maturities at June 30, 2019 by contractual maturity periods. Actual results may differ as issuers may have the right to call or prepay obligations, with or without penalties, prior to the contractual maturity of these obligations.

(in thousands)	June 30, 2019
	Amortized Cost		Estimated Fair Value
Due in one year or less	$	11,652	$	11,672
Due after one year through five years	7,641		7,650
Due after five years through ten years	194		192
Due after ten years	1,284		1,273
Total	$	20,771	$	20,787

The following tables highlight the aggregate unrealized loss position, by security type, of available-for-sale investments in unrealized loss positions as of June 30, 2019 and December 31, 2018. The tables segregate the holdings based on the period of time the investments have been continuously held in unrealized loss positions.

(in thousands)									June 30, 2019
	Less than 12 Months				Greater than 12 Months				Total
	Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss
Fixed maturities:
U.S. government, government agencies and authorities	$	2,497	$	2	$	1,950	$	11	$	4,447	$	13
States, municipalities and political subdivisions	75		—		453		4		528		4
Mortgage-backed	150		—		1,698		22		1,848		22
Corporate	121		—		1,123		9		1,244		9
Total fixed maturities	$	2,843	$	2	$	5,224	$	46	$	8,067	$	48

(in thousands)									December 31, 2018
	Less than 12 Months				Greater than 12 Months				Total
	Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss		Estimated Fair Value		Unrealized Loss
Fixed maturities:
U.S. government, government agencies and authorities	$	1,497	$	1	$	2,609	$	47	$	4,106	$	48
States, municipalities and political subdivisions	—		—		606		14		606		14
Mortgage-backed	800		1		2,134		69		2,934		70
Corporate	595		1		2,151		40		2,746		41
Total fixed maturities	$	2,892	$	3	$	7,500	$	170	$	10,392	$	173

There are approximately 44 and 64 individual available-for-sale investments that were in unrealized loss positions as of June 30, 2019 and December 31, 2018, respectively. 

The establishment of an other-than-temporary impairment on an investment requires a number of judgments and estimates. The Company performs a quarterly analysis of the individual investments to determine if declines in market value are other-than-temporary. The analysis includes some or all of the following procedures as deemed appropriate by the Company:

• identifying all unrealized loss positions that have existed for at least six months;

• identifying other circumstances management believes may affect the recoverability of the unrealized loss positions;

• obtaining a valuation analysis from third-party investment managers regarding the intrinsic value of these investments based on their knowledge and experience together with market-based valuation techniques;

• reviewing the trading range of certain investments over the preceding calendar period;

• assessing if declines in market value are other-than-temporary for debt instruments based on the investment grade credit ratings from third-party rating agencies;

• assessing if declines in market value are other-than-temporary for any debt instrument with a non-investment grade credit rating based on the continuity of its debt service record;

• determining the necessary provision for declines in market value that are considered other-than-temporary based on the analyses performed; and

• assessing the Company's ability and intent to hold these investments at least until any potential investment impairment is recovered.

The risks and uncertainties inherent in the assessment methodology used to determine declines in market value that are other-than-temporary include, but may not be limited to, the following:

• the opinions of professional investment managers could be incorrect;

• the past trading patterns of individual investments may not reflect future valuation trends;

• the credit ratings assigned by independent credit rating agencies may be incorrect due to unforeseen or unknown facts related to a company's financial situation; and

• the debt service pattern of non-investment grade instruments may not reflect future debt service capabilities and may not reflect a company's unknown underlying financial problems.

As a result of the analysis performed by the Company to determine declines in market value that are other-than-temporary, the Company recorded no write-downs for other-than-temporary impairment related to limited liability investments for the three months ended June 30, 2019 and June 30, 2018, respectively ($0.1 million year to date compared to zero prior year to date). There were no write-downs recorded for other-than-temporary impairments related to available-for sale investments for the three and six months ended June 30, 2019 and June 30, 2018, respectively.

The Company has reviewed currently available information regarding investments with estimated fair values less than their carrying amounts and believes these unrealized losses are not other-than-temporary and are primarily due to temporary market and sector-related factors rather than to issuer-specific factors. The Company does not intend to sell those investments, and it is not likely it will be required to sell those investments before recovery of its amortized cost.

The Company does not have any exposure to subprime mortgage-backed investments.

Limited liability investments include investments in limited liability companies and limited partnerships. The Company's interests in these investments are not deemed minor and, therefore, are accounted for under the equity method of accounting. The most recently available financial statements are used in applying the equity method. The difference between the end of the reporting period of the limited liability entities and that of the Company is no more than three months. As of June 30, 2019 and December 31, 2018, the carrying value of limited liability investments totaled $3.9 million and $4.8 million, respectively. Income or loss from limited liability investments is recognized based on the Company's share of the earnings of the limited liability entities and is included in net investment income in the consolidated statements of operations. At June 30, 2019, the Company has no unfunded commitments related to limited liability investments.

Limited liability investments, at fair value represents the Company's investment in 26.7% of the outstanding units of 1347 Investors LLC ("1347 Investors") as well as the underlying investments of the Company’s consolidated entities Net Lease Investment Grade Portfolio LLC ("Net Lease") and Argo Holdings Fund I, LLC ("Argo Holdings").

The fair value of the Company's investment in 1347 Investors is calculated based on a model that distributes the net equity of 1347 Investors to all classes of membership interests. The model uses quoted market prices and significant market observable inputs. The most significant input to the model is the observed stock price of Limbach Holdings, Inc. ("Limbach") common stock.

During the fourth quarter of 2019, the Company’s investment in 1347 Investors was dissolved, which resulted in the Company holding shares of Limbach common stock directly.  During the third and fourth quarters of 2019 and through the first quarter of 2020, the Limbach common stock price has declined, which has resulted in the Company recording loss on change in fair value related to its investment in 1347 Investors and Limbach of $2.7 million, $0.7 million and $0.6 million, respectively.

As of June 30, 2019 and December 31, 2018, the carrying value of the Company's limited liability investments, at fair value was $33.0 million and $26.0 million, respectively. The Company recorded impairments related to limited liability investments, at fair value of $0.0 million and zero for the three months ended June 30, 2019 and June 30, 2018, respectively, ($0.0 million and $0.0 million for the six months ended June 30, 2019 and June 30, 2018, respectively), which are included in (loss) gain on change in fair value of limited liability investments, at fair value in the consolidated statements of operations. At June 30, 2019, the Company has unfunded commitments totaling $0.6 million to fund limited liability investments, at fair value, all of which related to the Company’s commitment to Argo Holdings. On December 4, 2019, Argo Management informed members of Argo Holdings that no more requests for funds are planned.

Investments in private companies consist of convertible preferred stocks and notes in privately owned companies and investments in limited liability companies in which the Company’s interests are deemed minor. The Company's investments in private companies do not have readily determinable fair values. The Company has elected to record investments in private companies at cost, adjusted for observable price changes and impairments. As of June 30, 2019 and December 31, 2018, the carrying value of the Company's investments in private companies totaled $2.7 million and $3.1 million, respectively. For the three months ended June 30, 2019 and June 30, 2018, the Company recorded adjustments of zero and $0.2 million, respectively, ($0.0 million and $0.2 million for the six months ended June 30, 2019 and June 30, 2018, respectively), to adjust the fair value of certain investments in private companies for observable price changes, which are included in net change in unrealized gain (loss) on private company investments in the consolidated statements of operations.

The Company performs a quarterly impairment analysis of its investments in private companies. The analysis includes some or all of the following procedures as deemed appropriate by the Company:

• the opinions of external investment and portfolio managers;

• the financial condition and prospects of the investee;

• recent operating trends and forecasted performance of the investee;

• current market conditions in the geographic area or industry in which the investee operates;

• changes in credit ratings; and

• changes in the regulatory environment.

As a result of the analysis performed, the Company recorded no write-downs for other-than-temporary impairments related to investments in private companies for the three and six months ended June 30, 2019 and June 30, 2018.

Real estate investments are reported at fair value. As of June 30, 2019 and December 31, 2018, the carrying value of the Company's real estate investments totaled $10.7 million and $10.7 million, respectively.

Other investments include collateral loans and are reported at their unpaid principal balance. As of June 30, 2019 and December 31, 2018, the carrying value of other investments totaled $0.9 million and $2.1 million, respectively.

The Company had previously entered into two separate performance share grant agreements with 1347 Property Insurance Holdings, Inc. ("PIH"), whereby the Company will be entitled to receive up to an aggregate of 475,000 shares of PIH common stock upon achievement of certain milestones for PIH’s stock price. Pursuant to the performance share grant agreements, if at any time the last sales price of PIH’s common stock equals or exceeds: (i) $10.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 100,000 shares of PIH common stock; (ii) $12.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 100,000 shares of common stock earned pursuant to clause (i) herein); (iii) $15.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 225,000 shares of common stock earned pursuant to clauses (i) and (ii) herein); and (iv) $18.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 350,000 shares of common stock earned pursuant to clauses (i), (ii) and (iii) herein). To the extent shares of PIH common stock are granted to the Company under either of the performance share grant agreements, they will be recorded at the time the shares are granted and will have a valuation equal to the last sales price of PIH common stock on the day prior to such grant.

On January 2, 2018, the Company entered into an agreement with PIH to cancel the $10.00 per share performance shares grant agreement in exchange for cash consideration of $0.3 million. For the six months ended June 30, 2018, the Company recorded a gain, included in (loss) gain on change in fair value of equity investments in the consolidated statements of operations, of $0.3 million related to this transaction. No shares were received by the Company under either of the performance share grant agreements as of June 30, 2019.

Net investment income for the three and six months ended June 30, 2019 and June 30, 2018 is comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Investment income:
Interest from fixed maturities	$	122		$	57		$	195		$	90
Dividends	70			82			128			156
Income from limited liability investments	32			189			14			181
Income from limited liability investments, at fair value	232			482			467			701
Income from real estate investments	200			200			400			400
Other	112			9			290			137
Gross investment income	768			1,019			1,494			1,665
Investment expenses	(19		)	(9		)	(46		)	(17		)
Net investment income	$	749		$	1,010		$	1,448		$	1,648

Gross realized gains and losses on available-for-sale investments and limited liability investments for the three and six months ended June 30, 2019 and June 30, 2018 are comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Gross realized gains	$	44		$	133		$	359		$	398
Gross realized losses	(600		)	(1		)	(600		)	(1		)
Net realized (losses) gains	$	(556	)	$	132		$	(241	)	$	397

(Loss) gain on change in fair value of equity investments for the three and six months ended June 30, 2019 and June 30, 2018 is comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Net (losses) gains recognized on equity investments sold during the period	$	(101	)	$	(10	)	$	(101	)	$	545
Change in unrealized gains (losses) on equity investments held at end of the period	38			(411		)	116			199
(Loss) gain on change in fair value of equity investments	$	(63	)	$	(421	)	$	15		$	744

Short-term investments and fixed maturities with an estimated fair value of $0.2 million and $0.2 million at June 30, 2019 and December 31, 2018, respectively, were on deposit with state and provincial regulatory authorities. The Company also has restricted cash of $17.3 million and $17.0 million at June 30, 2019 and December 31, 2018, respectively. Included in restricted cash are (i) $5.1 million and $5.0 million at June 30, 2019 and December 31, 2018, respectively, held in escrow as part of the transaction to sell Mendota; (ii) $10.0 million and $10.0 million at June 30, 2019 and December 31, 2018, respectively, held as deposits by IWS Acquisition Corporation ("IWS"), Professional Warranty Service Corporation ("PWSC"), and Geminus; (iii) $1.9 million and $1.9 million at June 30, 2019 and December 31, 2018, respectively, on deposit with state and provincial regulatory authorities; and (iv) $0.3 million and $0.1 million at June 30, 2019 and December 31, 2018, respectively, pledged to third-parties as deposits or to collateralize liabilities. Collateral pledging transactions are conducted under terms that are common and customary to standard collateral pledging and are subject to the Company's standard risk management controls.

Impact of COVID-19 on Investments

As discussed in Note 24, "Subsequent Event," in March 2020 the outbreak of COVID-19 caused by a novel strain of the coronavirus was recognized as a pandemic by the World Health Organization, and the outbreak has become increasingly widespread in the United States, including in the markets in which we operate. The COVID-19 outbreak has had a notable impact on general economic conditions, including but not limited to the temporary closures of many businesses; "shelter in place" and other governmental regulations; and reduced consumer spending due to both job losses and other effects attributable to COVID-19. There remain many unknowns.

As part of the Company’s March 31, 2020 quarterly impairment analysis of its investments in private companies, the Company determined that it should write-down one of its investments by 90%, or $0.7 million, for other-than-temporary impairments as a result of the impacts of COVID-19 on the investment's underlying business. The Company continues to assess the impact that the COVID-19 pandemic may have on the value of its various investments, which could result in future material decreases in the underlying investment value. Such decreases may be considered temporary or could be deemed to be other-than-temporary and management may be required to record write-downs of the related investments in future reporting periods.

XML

Basis of Presentation

6 Months Ended

Jun. 30, 2019

Basis of Presentation [Abstract]

BASIS OF PRESENTATION

BASIS OF PRESENTATION

The accompanying unaudited consolidated interim financial statements have been prepared in accordance with accounting principles generally accepted in the United States of America ("U.S. GAAP") for interim financial information and with the instructions to Form 10-Q and Article 10 of Regulation S-X. Accordingly, they do not include all of the information and notes required by U.S. GAAP for complete financial statements of the Company. In the opinion of management, all adjustments necessary for a fair presentation have been included and are of a normal recurring nature. Interim results are not necessarily indicative of the results that may be expected for the year.

Certain prior year amounts have been reclassified to conform to current year presentation. Such reclassifications had no impact on previously reported net loss or total shareholders' equity.

The accompanying unaudited consolidated interim financial statements and footnotes should be read in conjunction with the audited consolidated financial statements and footnotes included within our Annual Report on Form 10-K ("2018 Annual Report") for the year ended December 31, 2018.

The unaudited consolidated interim financial statements include the accounts of the Company and its subsidiaries, as well as certain variable interest entities as further described in Note 7, "Variable Interest Entities," to the consolidated financial statements in the 2018 Annual Report. All material intercompany transactions and balances have been eliminated in consolidation.

The preparation of consolidated financial statements in conformity with U.S. GAAP requires management to make estimates and assumptions that affect the reported amounts and classifications of assets and liabilities, revenues and expenses, and the related disclosures of contingent assets and liabilities in the consolidated financial statements and accompanying notes. Actual results could differ from these estimates. Estimates and their underlying assumptions are reviewed on an ongoing basis. Changes in estimates are recorded in the accounting period in which they are determined. The critical accounting estimates and assumptions in the accompanying unaudited consolidated interim financial statements include the provision for unpaid loss and loss adjustment expenses; valuation of fixed maturities and equity investments; impairment assessment of investments; valuation of limited liability investments, at fair value; valuation of real estate investments; valuation of deferred income taxes; valuation of mandatorily redeemable preferred stock; valuation and impairment assessment of intangible assets; goodwill recoverability; deferred acquisition costs; fair value assumptions for subordinated debt obligations; and revenue recognition.

The fair values of the Company's investments in fixed maturities and equity investments, limited liability investments, at fair value, real estate investments, subordinated debt and warrant liability are estimated using a fair value hierarchy to categorize the inputs it uses in valuation techniques. The fair value of the Company's investment in investee is based on quoted market prices. Fair values for other investments approximate their unpaid principal balance. The carrying amounts reported in the consolidated balance sheets approximate fair values for cash and cash equivalents, restricted cash, short-term investments and certain other assets and other liabilities because of their short-term nature.

The Company's financial results contained herein are reported in U.S. dollars unless otherwise indicated.

XML

Related Parties - 1347 Energy Holdings LLC (Details) - USD ($)	Feb. 12, 2018	Jun. 30, 2019	Dec. 31, 2018
Principal Owner
Related Party Transaction [Line Items]
Equity method investment, ownership percentage		0.00%	45.60%
Chief Executive Officer
Related Party Transaction [Line Items]
Equity method investment, ownership percentage		0.00%	0.80%
Collateralized Agreements		$ 0	$ 600,000
Affiliated Entity
Related Party Transaction [Line Items]
Equity method investment, ownership percentage		0.00%	0.00%
1347 Energy Holdings LLC | Affiliated Entity
Related Party Transaction [Line Items]
Collateralized Agreements	$ 1,800,000
Proceeds from surety bonds	$ 700,000

XML

Leases - Annual Maturities of Lease Liabilities (Details) $ in Thousands	Jun. 30, 2019 USD ($)
Leases [Abstract]
2019	$ 463
2020	377
2021	388
2022	399
2023	422
2024 and thereafter	859
Total undiscounted lease payments	2,908
Imputed interest	498
Total lease liabilities	$ 2,410

XML

Property and Equipment (Details) - USD ($) $ in Thousands	Jun. 30, 2019	Dec. 31, 2018
Total Property and Equipment
Cost	$ 119,488	$ 119,100
Accumulated Depreciation	18,310	15,958
Carrying Value	101,178	103,142
Property leased to others under operating leases included in property and equipment
Cost	113,008	113,008
Accumulated Depreciation	12,271	10,197
Net property and equipment leased	100,737	102,811
Land
Total Property and Equipment
Cost	21,120	21,120
Accumulated Depreciation	0	0
Carrying Value	21,120	21,120
Property leased to others under operating leases included in property and equipment
Cost	21,120	21,120
Accumulated Depreciation	0	0
Net property and equipment leased	21,120	21,120
Site improvements
Total Property and Equipment
Cost	91,308	91,308
Accumulated Depreciation	12,228	10,161
Carrying Value	79,080	81,147
Property leased to others under operating leases included in property and equipment
Cost	91,308	91,308
Accumulated Depreciation	12,228	10,161
Net property and equipment leased	79,080	81,147
Buildings
Total Property and Equipment
Cost	580	580
Accumulated Depreciation	43	36
Carrying Value	537	544
Property leased to others under operating leases included in property and equipment
Cost	580	580
Accumulated Depreciation	43	36
Net property and equipment leased	537	544
Leasehold improvements
Total Property and Equipment
Cost	149	104
Accumulated Depreciation	103	102
Carrying Value	46	2
Property leased to others under operating leases included in property and equipment
Cost	0	0
Accumulated Depreciation	0	0
Net property and equipment leased	0	0
Furniture and equipment
Total Property and Equipment
Cost	1,042	993
Accumulated Depreciation	953	901
Carrying Value	89	92
Property leased to others under operating leases included in property and equipment
Cost	0	0
Accumulated Depreciation	0	0
Net property and equipment leased	0	0
Computer hardware
Total Property and Equipment
Cost	5,289	4,995
Accumulated Depreciation	4,983	4,758
Carrying Value	306	237
Property leased to others under operating leases included in property and equipment
Cost	0	0
Accumulated Depreciation	0	0
Net property and equipment leased	$ 0	$ 0

XML

(Details) - USD ($) $ in Thousands	6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Dec. 31, 2018	Dec. 31, 2017
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Balance at beginning of period, gross	$ 2,073
Paid related to:
Balance at end of period, gross	1,937	$ 2,594
Property, Liability and Casualty Insurance Product Line
Liability for Unpaid Claims and Claims Adjustment Expense [Roll Forward]
Balance at beginning of period, gross	2,073	1,329
Less reinsurance recoverable related to unpaid loss and loss adjustment expenses	0	100
Balance at beginning of period, net	2,073	1,257
Incurred related to:
Current year	0	0
Prior years	708	1,647
Paid related to:
Current year	0	0
Prior years	(844)	(410)
Balance at beginning of period, net	1,937	2,494
Plus reinsurance recoverable related to unpaid loss and loss adjustment expenses	$ 0	$ 100	$ 0	$ 72

XML

Commitment and Contingencies (Details) - USD ($)		6 Months Ended
	Jan. 20, 2020	Jun. 30, 2019
Loss Contingencies [Line Items]
Subscription agreement amount		$ 2,600,000
Unfunded commitments		$ 600,000
Subsidiaries | CMC
Loss Contingencies [Line Items]
Indirect ownership percentage owned by parent		81.00%
Subsidiaries | CMC | DGI
Loss Contingencies [Line Items]
Remaining ownership percentage owned by noncontrolling interest		19.00%
Breach of contract | Aegis
Loss Contingencies [Line Items]
Loss contingency accrual		$ 0
Breach of contract | Aegis | Subsequent Event
Loss Contingencies [Line Items]
One-time settlement amount	$ 900,000
Percentage of future losses reimbursable	60.00%
Maximum litigation reimbursement amount	$ 4,800,000

XML

Revenue from Contracts with Customers - Narrative (Details) - USD ($) $ in Thousands	6 Months Ended
	Jun. 30, 2019	Dec. 31, 2018
Revenue from Contract with Customer [Abstract]
Contract period	4 years
Service fee receivable, net	$ 5,246	$ 3,434
Service fee and commission income recognized during the period	$ 7,900

XML

Earnings From Continuing Operations Per Share (Details) - USD ($) $ / shares in Units, shares in Thousands, $ in Thousands	3 Months Ended			6 Months Ended		9 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Sep. 30, 2016	Jun. 30, 2019	Jun. 30, 2018	Sep. 30, 2016
Numerator:
Income (loss) from continuing operations	$ (396)	$ (4,262)		$ 2,793	$ (6,866)
Less: net income attributable to noncontrolling interests	(258)	(158)		(469)	(517)
Less: dividends on preferred stock, net of tax	(252)	(259)		(498)	(512)
Income (loss) from continuing operations attributable to common shareholders	$ (906)	$ (4,679)		$ 1,826	$ (7,895)
Denominator:
Weighted average common shares outstanding (in shares)	21,867	21,708		21,854	21,708
Effect of potentially dilutive securities (in shares)
Warrants (in shares)		0	0		0	0
Convertible preferred stock (in shares)		0	0		0	0
Total weighted average diluted shares (in shares)	21,867	21,708		21,854	21,708
Basic (in dollars per share)	$ (0.04)	$ (0.22)		$ 0.08	$ (0.36)
Diluted (in dollars per share)	$ (0.04)	$ (0.22)		$ 0.08	$ (0.36)
Stock options
Denominator:
Effect of potentially dilutive securities (in shares)		0	0		0	0
Restricted Stock
Denominator:
Unvested restricted stock (in shares)		0	0		0	0
Restricted Stock Units (RSUs)
Denominator:
Unvested restricted stock (in shares)	0	0		0	0

XML

Leases - Adoption of ASC 842 (Details) - USD ($) $ in Thousands	Jun. 30, 2019	Jan. 01, 2019	Dec. 31, 2018
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Right-of-use asset	$ 2,265
Lease liability	2,410
Accrued expenses and other liabilities	$ 16,518		$ 14,786
ASU 2016-02
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Right-of-use asset		$ 2,700
Lease liability		2,900
Accrued expenses and other liabilities		$ 200

XML

Acquisition and Discontinued Operations - Discontinued Operations (Details) $ in Thousands	3 Months Ended				6 Months Ended		12 Months Ended
	Mar. 31, 2020 USD ($)	Jun. 30, 2019 USD ($)	Mar. 31, 2019 USD ($) claim	Jun. 30, 2018 USD ($)	Jun. 30, 2019 USD ($)	Jun. 30, 2018 USD ($)	Dec. 31, 2018 USD ($)	Dec. 31, 2019 USD ($)	Oct. 18, 2018 USD ($)	Apr. 01, 2015
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Gain (loss) on disposal of discontinued operation, net		$ 0		$ (6,628)	$ 0	$ (6,628)
Final aggregate purchase price				1,700		1,700
Mendota
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Gain (loss) on disposal of discontinued operation, net		$ (8,000)					$ (8,500)
Final aggregate purchase price									$ 28,600
Escrow deposit									$ 5,000
Maximum obligation				$ 2,500		$ 2,500
Number of claims settled | claim			1
Indemnification claim settled			$ 500
Mendota | Forecast
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Estimated net loss								$ 1,600
Released escrow deposit	$ 3,400
Discontinued Operations
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Gain (loss) on disposal of discontinued operation, net							$ 1,300
Future earnout payments, as a percentage of written premium and fee income										1.25%

XML

Recently Issued Accounting Standards (Details) $ in Thousands	Jan. 01, 2018 USD ($)
ASU 2014-09
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Cumulative effect of change on equity or net assets	$ 600
Effect of adoption, quantification	600
Cumulative effect of adoption of ASU	(654)
ASU 2014-09 | Accumulated Deficit
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Cumulative effect of adoption of ASU	(647)
ASU 2016-01 | Accumulated Deficit
New Accounting Pronouncements or Change in Accounting Principle [Line Items]
Cumulative effect of adoption of ASU	$ (40,495)

XML

Consolidated Statements of Comprehensive (Loss) Income (Parenthetical) - USD ($)	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Statement of Comprehensive Income [Abstract]
Other comprehensive income (loss), tax	$ 0	$ 0	$ 0	$ 0

XML

Consolidated Balance Sheets - USD ($) $ in Thousands	Jun. 30, 2019	Dec. 31, 2018
Investments:
Fixed maturities, at fair value (amortized cost of $20,771 and $12,432, respectively)	$ 20,787	$ 12,260
Equity investments, at fair value (cost of $1,506 and $2,274, respectively)	202	856
Limited liability investments	3,891	4,790
Limited liability investments, at fair value	33,047	26,015
Investments in private companies, at adjusted cost	2,661	3,090
Real estate investments, at fair value (cost of $10,225 and $10,225, respectively)	10,662	10,662
Other investments, at cost which approximates fair value	895	2,079
Short-term investments, at cost which approximates fair value	154	152
Total investments	72,299	59,904
Cash and cash equivalents	10,899	14,619
Restricted cash	17,320	16,959
Investment in investee	1,119	951
Accrued investment income	417	420
Service fee receivable, net of allowance for doubtful accounts of $324 and $191, respectively	5,246	3,434
Other receivables, net of allowance for doubtful accounts of $201 and $184, respectively	10,554	9,523
Deferred acquisition costs, net	7,724	6,904
Property and equipment, net of accumulated depreciation of $18,310 and $15,958, respectively	101,178	103,142
Right-of-use asset	2,265
Goodwill	82,104	74,659
Intangible assets, net of accumulated amortization of $11,791 and $10,594, respectively	87,775	83,266
Other assets	5,394	4,459
Total Assets	404,294	378,240
Liabilities:
Accrued expenses and other liabilities	16,518	14,786
Income taxes payable	2,482	2,400
Deferred service fees	61,522	47,130
Unpaid loss and loss adjustment expenses	1,937	2,073
Bank loans	11,674	3,917
Notes payable	197,039	199,316
Subordinated debt, at fair value	50,224	50,023
Lease liability	2,410
Net deferred income tax liabilities	28,984	28,537
Total Liabilities	372,790	348,182
Redeemable Class A preferred stock, no par value; 1,000,000 and unlimited number authorized at June 30, 2019 and December 31, 2018, respectively; 222,876 and 222,876 issued and outstanding at June 30, 2019 and December 31, 2018, respectively; redemption amount of $7,485 and $7,278 at June 30, 2019 and December 31, 2018, respectively	6,297	5,800
Shareholders' Equity:
Common stock, no par value; 50,000,000 and unlimited number authorized at June 30, 2019 and December 31, 2018, respectively; 21,866,959 and 21,787,728 issued and outstanding at June 30, 2019 and December 31, 2018, respectively	0	0
Additional paid-in capital	353,778	353,890
Accumulated deficit	(379,872)	(382,196)
Accumulated other comprehensive income	39,325	40,768
Shareholders' equity attributable to common shareholders	13,231	12,462
Noncontrolling interests in consolidated subsidiaries	11,976	11,796
Total Shareholders' Equity	25,207	24,258
Total Liabilities, Class A preferred stock and Shareholders' Equity	$ 404,294	$ 378,240

XML

Intangible Assets - Additional Information (Details) - USD ($)	3 Months Ended			6 Months Ended
	Jun. 30, 2019	Mar. 31, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018	Mar. 01, 2019
Finite-Lived Intangible Assets [Line Items]
Amortization of intangible assets	$ 676,000		$ 254,000	$ 1,197,000	$ 509,000
Impairment charges	$ 0		$ 0	$ 0	$ 0
Minimum
Finite-Lived Intangible Assets [Line Items]
Intangible asset useful life		7 years
Maximum
Finite-Lived Intangible Assets [Line Items]
Intangible asset useful life		18 years
Customer relationships
Finite-Lived Intangible Assets [Line Items]
Intangible asset useful life		10 years
Geminus
Finite-Lived Intangible Assets [Line Items]
Intangible assets acquired						$ 5,700,000
Geminus | Trade names
Finite-Lived Intangible Assets [Line Items]
Intangible assets acquired						1,974,000
Geminus | Customer relationships
Finite-Lived Intangible Assets [Line Items]
Recognized identifiable assets acquired and liabilities assumed						$ 3,732,000

XML

Fair Value of Financial Instruments - Valuation Techniques Used to Measure Investments (Details) $ in Thousands	Jun. 30, 2019 USD ($)	Mar. 31, 2019 USD ($)	Dec. 31, 2018 USD ($)	Jun. 30, 2018 USD ($)	Mar. 31, 2018 USD ($)	Dec. 31, 2017 USD ($)
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, at fair value	$ 2,661		$ 3,090
Real estate investments	10,662		10,662
Warrant liability	307
Significant Unobservable Inputs (Level 3)
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, at fair value	4,635		4,124
Real estate investments	10,662	$ 10,662	10,662	$ 10,662	$ 10,662	$ 10,662
Warrant liability	$ 307	$ 317	$ 0	$ 0	$ 0	$ 0
Significant Unobservable Inputs (Level 3) | Cap rates
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Real estate investments, measurement input	0.075		0.075
Significant Unobservable Inputs (Level 3) | Minimum | Valuation multiples
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, measurement input	5.0		5.0
Warrant liability, measurement input	6.0
Significant Unobservable Inputs (Level 3) | Maximum | Valuation multiples
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, measurement input	8.8		8.8

XML

Related Parties - Itasca Golf Investors, LLC (Details) - Investor - USD ($) $ in Millions	Sep. 05, 2018	Apr. 08, 2014
Related Party Transaction [Line Items]
Equity method investment, ownership percentage		42.90%
Proceeds from sale of equity method investments	$ 1.5

XML

Related Parties - 1347 Property Insurance Holdings, Inc (Details) $ / shares in Units, $ in Millions								6 Months Ended	12 Months Ended
	Jul. 24, 2018 USD ($) $ / shares	Mar. 15, 2018 shares	Jan. 02, 2018 USD ($) $ / shares	Nov. 01, 2017 shares	Oct. 25, 2017 USD ($) $ / shares shares	Feb. 24, 2015 USD ($) day $ / shares shares	Mar. 26, 2014 day $ / shares shares	Jun. 30, 2019 $ / shares shares	Dec. 31, 2018
Clause 1, 2 and 3
Related Party Transaction [Line Items]
Stock reserved for future issuances (in shares)								350,000
Clause 1 and 2
Related Party Transaction [Line Items]
Stock reserved for future issuances (in shares)								225,000
Clause 2
Related Party Transaction [Line Items]
Stock reserved for future issuances (in shares)								125,000
Share price (in dollars per share) | $ / shares	$ 12.00							$ 12.00
Clause 3
Related Party Transaction [Line Items]
Share price (in dollars per share) | $ / shares	$ 15.00							$ 15
Affiliated Entity
Related Party Transaction [Line Items]
Equity method investment, ownership percentage								0.00%	0.00%
Management
Related Party Transaction [Line Items]
Stock issued (in shares)				475,428	900,000
Share price (in dollars per share) | $ / shares					$ 7.85
Proceeds from termination of contract | $			$ 0.3
Proceeds from sale of equity | $			3.0
Consideration received on transaction | $	$ 1.0		$ 3.0
Common Stock | Management
Related Party Transaction [Line Items]
Effect on future cash flows | $					$ 7.1
Other shares (in shares)		424,572
Maximum
Related Party Transaction [Line Items]
Share price (in dollars per share) | $ / shares	$ 18.00							$ 18
Fundamental Global Investors, LLC | Kingsway Financial Services, Inc
Related Party Transaction [Line Items]
Ownership percentage (less than at June 30, 2019)								5.00%	5.00%
1347 Property Insurance Holdings, Inc.
Related Party Transaction [Line Items]
Preferred stock, dividend rate			8.00%			8.00%
1347 Property Insurance Holdings, Inc. | Clause 2
Related Party Transaction [Line Items]
Share price (in dollars per share) | $ / shares						$ 15.00
1347 Property Insurance Holdings, Inc. | Affiliated Entity
Related Party Transaction [Line Items]
Effect on future cash flows | $						$ 2.0
Stock issued (in shares)						3,000,000
Stock reserved for future issuances (in shares)						100,000
Share price (in dollars per share) | $ / shares			$ 10.00			$ 10.00
Threshold trading days | day						20
Threshold consecutive trading days						30 days
1347 Property Insurance Holdings, Inc. | Affiliated Entity | Clause 1, 2 and 3
Related Party Transaction [Line Items]
Stock reserved for future issuances (in shares)							375,000
1347 Property Insurance Holdings, Inc. | Affiliated Entity | Clause 1 and 2
Related Party Transaction [Line Items]
Stock reserved for future issuances (in shares)							250,000
1347 Property Insurance Holdings, Inc. | Affiliated Entity | Clause 2
Related Party Transaction [Line Items]
Stock reserved for future issuances (in shares)							125,000
Share price (in dollars per share) | $ / shares							$ 15.00
Threshold trading days | day							20
Threshold consecutive trading days							30 days
1347 Property Insurance Holdings, Inc. | Affiliated Entity | Clause 1
Related Party Transaction [Line Items]
Stock reserved for future issuances (in shares)							125,000
Share price (in dollars per share) | $ / shares							$ 12.00
Threshold trading days | day							20
Threshold consecutive trading days							30 days
1347 Property Insurance Holdings, Inc. | Affiliated Entity | Clause 3
Related Party Transaction [Line Items]
Stock reserved for future issuances (in shares)							125,000
1347 Property Insurance Holdings, Inc. | Common Stock | Affiliated Entity
Related Party Transaction [Line Items]
Other shares (in shares)						1,500,000
1347 Property Insurance Holdings, Inc. | Maximum | Affiliated Entity
Related Party Transaction [Line Items]
Share price (in dollars per share) | $ / shares							$ 18.00
Threshold trading days | day							20
Threshold consecutive trading days							30 days

XML

Segmented Information - Revenue by Reportable Segment (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Segment Reporting Information [Line Items]
Service fee and commission income	$ 11,772	$ 8,860	$ 21,587	$ 18,511
Other income	113	108	258	321
Rental income	3,341	3,345	6,682	6,693
Total revenues	15,226	12,313	28,527	25,525
Operating Segments
Segment Reporting Information [Line Items]
Total revenues	15,226	12,309	28,527	25,514
Not allocated to segments
Segment Reporting Information [Line Items]
Rental income	0		0
Rental income		4		11
Extended Warranty | Operating Segments
Segment Reporting Information [Line Items]
Service fee and commission income	11,772	8,860	21,587	18,511
Other income	41	36	116	102
Total revenues	11,813	8,896	21,703	18,613
Leased Real Estate | Operating Segments
Segment Reporting Information [Line Items]
Other income	72	72	142	219
Rental income	3,341		6,682
Rental income		3,341		6,682
Total revenues	$ 3,413	$ 3,413	$ 6,824	$ 6,901

XML

Investments - Gain in change fair value of equity investments (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Investments [Abstract]
Net (losses) gains recognized on equity investments sold during the period	$ (101)	$ (10)	$ (101)	$ 545
Change in unrealized gains (losses) on equity investments held at end of the period	38	(411)	116	199
(Loss) gain on change in fair value of equity investments	$ (63)	$ (421)	$ 15	$ 744

XML

Investments - Unrealized Loss Position (Details) - USD ($) $ in Thousands	Jun. 30, 2019	Dec. 31, 2018
Fixed Maturities
Estimated Fair Value
Less than 12 Months	$ 2,843	$ 2,892
Greater than 12 Months	5,224	7,500
Total	8,067	10,392
Unrealized Loss
Less than 12 Months	2	3
Greater than 12 Months	46	170
Total	48	173
U.S. government, government agencies and authorities
Estimated Fair Value
Less than 12 Months	2,497	1,497
Greater than 12 Months	1,950	2,609
Total	4,447	4,106
Unrealized Loss
Less than 12 Months	2	1
Greater than 12 Months	11	47
Total	13	48
States, municipalities and political subdivisions
Estimated Fair Value
Less than 12 Months	75	0
Greater than 12 Months	453	606
Total	528	606
Unrealized Loss
Less than 12 Months	0	0
Greater than 12 Months	4	14
Total	4	14
Mortgage-backed
Estimated Fair Value
Less than 12 Months	150	800
Greater than 12 Months	1,698	2,134
Total	1,848	2,934
Unrealized Loss
Less than 12 Months	0	1
Greater than 12 Months	22	69
Total	22	70
Corporate
Estimated Fair Value
Less than 12 Months	121	595
Greater than 12 Months	1,123	2,151
Total	1,244	2,746
Unrealized Loss
Less than 12 Months	0	1
Greater than 12 Months	9	40
Total	$ 9	$ 41

XML

Fair Value of Financial Instruments - Investments at Fair Value Using Net Asset Value Per Share As Practical Expedient (Details) - USD ($) $ in Thousands	Jun. 30, 2019	Dec. 31, 2018
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, at fair value	$ 33,047	$ 26,015
Measured at Net Asset Value
Fair Value, Assets and Liabilities Measured on Recurring and Nonrecurring Basis [Line Items]
Limited liability investments, at fair value	$ 22,114	$ 21,685

XML

Stock-Based Compensation - Restricted Stock Awards (Details) - Restricted Stock - $ / shares	3 Months Ended	6 Months Ended
	Mar. 31, 2019	Jun. 30, 2019
Number of Restricted Stock Awards
Unvested, Beginning of Period (in shares)	1,092,450	1,092,450
Vested (in shares)	79,231.000
Cancelled for Tax Withholding (in shares)		(36,269)
Unvested, End of Period (in shares)		976,950
Weighted-Average Grant Date Fair Value (per Share)
Unvested, Beginning of Period (in dollars per share)	$ 4.51	$ 4.51
Vested (in dollars per share)		4.14
Cancelled for Tax Withholding (in dollars per share)		4.14
Unvested, End of Period (in dollars per share)		$ 4.55

XML

Unpaid Loss and Loss Adjustment Expenses (Tables)

6 Months Ended

Jun. 30, 2019

Insurance [Abstract]

Schedule of Liability for Unpaid Claims and Claims Adjustment Expense

The results of this comparison and the changes in the provision for unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of June 30, 2019 and June 30, 2018 were as follows:

(in thousands)	June 30, 2019			June 30, 2018
Balance at beginning of period, gross	$	2,073		$	1,329
Less reinsurance recoverable related to unpaid loss and loss adjustment expenses	—			72
Balance at beginning of period, net	2,073			1,257
Incurred related to:
Current year	—			—
Prior years	708			1,647
Paid related to:
Current year	—			—
Prior years	(844		)	(410		)
Balance at end of period, net	1,937			2,494
Plus reinsurance recoverable related to unpaid loss and loss adjustment expenses	—			100
Balance at end of period, gross	$	1,937		$	2,594

XML

Income Taxes (Tables)

6 Months Ended

Jun. 30, 2019

Income Tax Disclosure [Abstract]

Income Tax (Benefit) Expense

The following table summarizes the differences:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Income tax (benefit) expense at United States statutory income tax rate	$	(48	)	$	(855	)	$	472		$	(1,348	)
Valuation allowance	97			822			(1,234		)	1,354
Non-deductible compensation	25			62			34			123
Disposition of subsidiary	(24		)	—			(24		)	—
State income tax	32			67			58			133
Change in unrecognized tax benefits(1)	71			60			141			130
Indefinite life intangibles	54			24			87			46
Foreign operations subject to different tax rates	(20		)	(39		)	(17		)	(54		)
Other	(19		)	49			(62		)	60
Income tax expense (benefit)	$	168		$	190		$	(545	)	$	444
(1) Includes interest and penalty expense related to unrecognized tax benefits.

XML

Stock-Based Compensation

6 Months Ended

Jun. 30, 2019

Share-based Payment Arrangement [Abstract]

STOCK-BASED COMPENSATION

STOCK-BASED COMPENSATION

(a)     Stock Options

The following table summarizes the stock option activity during the six months ended June 30, 2019:

	Number of Options Outstanding	Weighted-Average Exercise Price		Weighted-Average Remaining Contractual Term (in Years)	Aggregate Intrinsic Value (in Thousands)
Outstanding at December 31, 2018	40,000	$	4.67	1.3	$	—
Granted	—	—
Expired	—	—
Outstanding at June 30, 2019	40,000	$	4.67	0.8	$	—
Exercisable at June 30, 2019	40,000	$	4.67	0.8	$	—

The aggregate intrinsic value of stock options outstanding and exercisable is the difference between the June 30, 2019 market price for the Company's common shares and the exercise price of the options, multiplied by the number of options where the fair value exceeds the exercise price.

The Company uses the Black-Scholes option pricing model to estimate the fair value of each option on the date of grant. No options were granted during the six months ended June 30, 2019.

(b)     Restricted Stock Awards

Under the 2013 Equity Incentive Plan (the "2013 Plan"), the Company made grants of restricted common stock awards to certain officers of the Company on March 28, 2014 (the "2014 Restricted Stock Awards"). The 2014 Restricted Stock Awards shall become fully vested and the restriction period shall lapse as of March 28, 2024 subject to the officers' continued employment through the vesting date. The 2014 Restricted Stock Awards are amortized on a straight-line basis over the ten-year requisite service period. The grant-date fair value of the 2014 Restricted Stock Awards was determined using the closing price of Kingsway common stock on the date of grant. Total unamortized compensation expense related to unvested 2014 Restricted Stock Awards at June 30, 2019 was $0.5 million.

During the third quarter of 2018, the Company modified the terms of the 2014 Restricted Stock Awards for two of its officers.

On September 5, 2018, the Company executed an Amended and Restated Restricted Stock Award Agreement ("Amended RSA Agreement") with its former Chief Executive Officer. Under the terms of the Amended RSA Agreement, the former Chief Executive Officer was deemed to have forfeited 1,382,665 shares of the 2014 Restricted Stock Awards. The Company’s accounting policy is to account for forfeitures when they occur. As a result, the Company reversed during the third quarter of 2018 $2.4 million of compensation expense previously recognized from March 28, 2014 through June 30, 2018.

Pursuant to the terms of the Amended RSA Agreement, the Company granted to the former Chief Executive Officer a modified award of 350,000 shares of restricted common stock (the "2018 Restricted Stock Award"). The Company deemed the 2018 Restricted Stock Award to be taxable to the former Chief Executive Officer on the modification date. Pursuant to the terms of the 2013 Plan and the Amended RSA Agreement, the former Chief Executive Officer was entitled to satisfy the tax withholding obligation by authorizing the Company to withhold restricted common shares, which would otherwise be deliverable, having an aggregate fair market value, determined as of the tax date, equal to the tax withholding obligation. The former Chief Executive Officer chose to satisfy the tax withholding obligation in this manner. As a result, the Company cancelled 102,550 of the 350,000 shares of the 2018 Restricted Stock Award.

The remaining 247,450 shares of the 2018 Restricted Stock Award shall become fully vested after the satisfaction of certain performance conditions, as defined in the Amended RSA Agreement. There is no defined term under which the performance conditions must be completed. The unamortized compensation expense for the 2018 Restricted Stock Award will be recognized at the time the performance condition has been satisfied. The grant-date fair value of the 2018 Restricted Stock Award was determined using the closing price of Kingsway common stock on the modification date. Total unamortized compensation expense related to the unvested 2018 Restricted Stock Award at June 30, 2019 was $0.6 million. During the fourth quarter of 2019, the Company acquired the remaining 247,450 shares of the 2018 Restricted Stock Award as partial consideration in exchange for selling its remaining investment in the common stock of ICL. See Note 22, "Related Parties," for more information.

On January 31, 2019, the Company executed an Employee Separation Agreement and Release ("Separation Agreement") with a former officer. The Separation Agreement modified the vesting terms related to 115,500 shares of the original 2014 Restricted Stock Awards ("Modified Restricted Stock Award"), such that they became fully vested on January 31, 2019. The Company deemed the Modified Restricted Stock Award to be taxable to the former officer on the vesting date. Pursuant to the terms of the 2013 Plan and the Separation Agreement, the former officer was entitled to satisfy the tax withholding obligation by authorizing the Company to withhold restricted common shares, which would otherwise be deliverable, having an aggregate fair market value, determined as of the tax date, equal to the tax withholding obligation. The former officer chose to satisfy the tax withholding obligation in this manner. As a result, the Company cancelled 36,269 of the 115,500 shares of the Modified Restricted Stock Award and recognized payroll tax expense of $0.1 million during the first quarter of 2019.

The Company also recorded during the first quarter of 2019 $0.1 million of compensation expense equal to the fair value of the remaining 79,231 fully vested shares of the Modified Restricted Stock Award. The grant-date fair value of the Modified Restricted Stock Award was determined using the closing price of Kingsway common stock on the modification date. Total unamortized compensation expense related to the unvested Modified Restricted Stock Award at June 30, 2019 was zero.

The Company granted restricted common stock units ("Restricted Stock Units") to an officer of the Company pursuant to a Restricted Stock Unit Agreement dated August 24, 2016. On September 5, 2018, the Restricted Stock Unit Agreement was cancelled and 500,000 restricted common stock awards were granted to the officer (the "2018 Restricted Stock Award"). There was no change to the vesting terms. The 2018 Restricted Stock Award shall become fully vested and the restriction period shall lapse as of March 28, 2024 subject to the officer's continued employment through the vesting date. The 2018 Restricted Stock Award is amortized on a straight-line basis over the requisite service period. The grant-date fair value of the 2018 Restricted Stock Award was determined using the closing price of Kingsway common stock on the date of grant. Total unamortized compensation expense related to unvested 2018 Restricted Stock Award at June 30, 2019 was $1.8 million.

The following table summarizes the activity related to unvested 2014 Restricted Stock Awards, 2018 Modified Restricted Stock Award, Modified Restricted Stock Award and 2018 Restricted Stock Award (collectively "Restricted Stock Awards") for the six months endedJune 30, 2019:

	Number of Restricted Stock Awards		Weighted-Average Grant Date Fair Value (per Share)
Unvested at December 31, 2018	1,092,450		$	4.51
Vested	(79,231	)	4.14
Cancelled for Tax Withholding	(36,269	)	4.14
Unvested at June 30, 2019	976,950		$	4.55

The unvested balance at June 30, 2019 in the table above is comprised of 229,500 shares of 2014 Restricted Stock Awards, 247,450 shares of 2018 Modified Restricted Stock Award and 500,000 shares of the 2018 Restricted Stock Award.

(c)     Restricted Stock Awards of PWSC

PWSC granted 1,000 restricted common stock awards ("PWSC Restricted Stock Award") to an officer of PWSC pursuant to an agreement dated September 7, 2018. The PWSC Restricted Stock Award contains both a service and a performance condition that affects vesting. The service condition vests according to a graded vesting schedule and shall become fully vested on February 20, 2022 subject to the officer's continued employment through the applicable vesting dates. The service condition component of the PWSC Restricted Stock Award is amortized on a straight-line basis over the requisite service period. The performance condition vests on February 20, 2022 and is based on the internal rate of return of PWSC. Accruals of compensation expense for the performance condition component of the PWSC Restricted Stock Award is estimated based on the probable outcome of the performance condition. The grant-date fair value of the PWSC Restricted Stock Award was estimated using a valuation model. At June 30, 2019, there were 875 unvested shares of the PWSC Restricted Stock Award with a weighted-average grant date fair value of $824.47 per share. Total unamortized compensation expense related to unvested PWSC Restricted Stock Award at June 30, 2019 was $0.7 million.

Total stock-based compensation expense, inclusive of Stock Options, Restricted Stock Awards and Restricted Stock Awards of PWSC described above, net of forfeitures, was $0.2 million and $0.3 million for the three months ended June 30, 2019 and June 30, 2018, respectively ($0.4 million and $0.6 million for the six months ended June 30, 2019 and June 30, 2018, respectively).

XML

Leases

6 Months Ended

Jun. 30, 2019

Leases [Abstract]

LEASES

LEASES

Financial Statement Impact of Adopting Accounting Standards Update No. 2016-02 "Leases (Topic 842)" ("ASU 2016-02" or "ASC 842")

The Company adopted ASU 2016-02 on January 1, 2019 using the modified retrospective adoption method. The reported results for 2019 reflect the adoption of ASC 842 guidance while the reported results for 2018 were prepared and continue to be reported under the guidance of ASC 840, Leases, referred to herein as "previous guidance."

ASC 842 provides guidance for both lessees and lessors. The Company is the lessee where it leases certain office properties from lessors. The Company is the lessor when it leases certain property to lessees.

The guidance requires lessees to recognize right-of-use assets and lease liabilities in the balance sheet and disclose key information about leasing arrangements, such as information about variable lease payments and options to renew and terminate leases. The amended guidance will require both operating and finance leases to be recognized in the balance sheet. A lessee should recognize in the statement of financial position a liability to make lease payments (the lease liability) and a right-of-use asset ("ROU") representing its right to use the underlying asset for the lease term.

The guidance requires lessors to classify leases as a sales-type, direct financing, or operating lease. A lease is classified as a sales-type lease if any one of five criteria are met, each of which indicate that the lease, in effect, transfers control of the underlying asset to the lessee. If none of those five criteria are met, but two additional criteria are both met, indicating that the lessor has transferred substantially all the risks and benefits of the underlying asset to the lessee and a third party, the lease is classified as a direct financing lease. All leases that are not classified as sales-type or direct financing leases are classified as operating leases.

The Company elected certain of the practical expedients that are permitted under the transition guidance which allowed the Company to carryforward the historical lease classification, not reassess initial direct costs for any existing leases as of January 1, 2019 or reassess whether any expired or existing contracts are or contain leases. In addition, the Company elected to adopt the “hindsight” practical expedient to determine the reasonably certain lease term for existing leases. The Company has revised its relevant policies and procedures, as applicable, to meet the new accounting, reporting and disclosure requirements of ASC 842 and have updated internal controls accordingly.

The main difference between the guidance in ASU 2016-02 and prior guidance for lessees is the recognition of right-of-use assets and lease liabilities for those leases classified as operating leases. Recognition of the right-of-use assets and liabilities had a material impact to the Company’s consolidated balance sheet upon adoption. However, since all its leases are operating leases under ASC 840 and the Company will carryforward the historical lease classification, the new standard did not have a material impact on the Company’s consolidated statements of operations, consolidated statements of shareholder’s equity, or consolidated statements of cash flows.

The adoption resulted in an increase of the ROU assets of approximately $2.7 million and lease liabilities of $2.9 million. The difference of $0.2 million relates to straight-line rent accruals and lease incentive liabilities that were reclassified to ROU assets for operating leases.

The main difference between the guidance in ASU 2016-02 and prior guidance for lessors is a modification of what qualifies as a sales-type and direct financing lease. All the Company’s lessor leases are classified as operating leases.

Lease Accounting Policy

The Company determines lease classification at commencement date. Leases not classified as sales-type (lessor) or financing leases (lessor and lessee) are classified as operating leases. The primary accounting criteria the Company uses that results in operating lease classification are: (a) the lease does not transfer ownership of the underlying asset to the lessee by the end of the lease term, (b) the lease does not grant the lessee a purchase option that the lessee is reasonably certain to exercise, (c) using a seventy-five percent or more threshold, the lease term is not for a major part of the remaining economic life of the underlying asset, (d) using a ninety percent or more threshold, the present value of the sum of the lease payments and residual value guarantee from the lessee does not equal or substantially exceeds all of the fair value of the underlying asset.

Rental income from operating leases is recognized on a straight-line basis, based on contractual lease terms with fixed and determinable increases over the non-cancellable term of the related lease when collectability is reasonably assured. Rental expense for operating leases is recognized on a straight-line basis over the lease term, net of any applicable lease incentive amortization.

Lessee Leases

The Company has operating leases for office space which include fixed base rent payments, as well as variable rent payments to reimburse the landlord for operating expenses and taxes. The Company’s variable lease payments do not depend on a published index or rate, and therefore, are expensed as incurred. The Company includes only fixed payments for lease components in the measurement of the right-of-use asset and lease liability. There are no residual value guarantees. The Company does not currently have leases that meet the finance lease classification as defined under ASC 842.

The Company treats contracts as a lease when the contract: (1) conveys the right to use a physically distinct asset for a period of time in exchange for consideration, (2) the Company directs the use of the asset and (3) the Company obtains substantially all the economic benefits of the asset. Right-of-use assets and lease liabilities are measured and recognized based on the present value of the future minimum lease payments over the lease term at the commencement date. As the Company’s leases are office leases, the Company is unable to determine an implicit rate; therefore, the Company uses its incremental borrowing rate based on the information available at the lease commencement date in determining the present value of future payments for those leases. The Company includes options to extend or terminate the lease in the measurement of the right-of-use asset and lease liability when it is reasonably certain that such options will be exercised. Lease expense for minimum lease payments is recognized on a straight-line basis over the lease term.

As an accounting policy, the Company has elected not to apply the recognition requirements in ASC 842 to short-term leases (generally those with terms of twelve months or less). Instead, the Company recognizes the lease payments as expense on a straight-line basis over the lease term and any variable lease payments in the period in which the obligation for those payments is incurred.

The ROU assets and lease liability are presented as separate line items on the face of the Company’s consolidated balance sheet as of June 30, 2019.

Operating lease costs and variable lease costs included in selling and administrative costs for the three months ended June 30, 2019 were $0.2 million and de minimis, respectively. Operating lease costs and variable lease costs included in selling and administrative costs for the six months ended June 30, 2019 were $0.5 million and de minimis, respectively.

The annual maturities of lease liabilities as of June 30, 2019 were as follows:

(in thousands)	Lease Commitments
2019	$	463
2020	377
2021	388
2022	399
2023	422
2024 and thereafter	859
Total undiscounted lease payments	2,908
Imputed interest	498
Total lease liabilities	$	2,410

The weighted-average remaining lease term for our operating leases was 6.40 years as of June 30, 2019. The weighted average discount rate of our operating leases was 5.69% as of June 30, 2019. Cash paid for amounts included in the measurement of lease liabilities was $0.5 million for the six months ended June 30, 2019.

Lessor Leases

The Company owns a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property") that is subject to a long-term triple net lease agreement with an unrelated third-party. The lease provides for future rent escalations and renewal options. The initial lease term ends in May 2034. The lessee bears the cost of maintenance and property taxes. Rental income from operating leases is recognized on a straight-line basis, based on contractual lease terms with fixed and determinable increases over the non-cancellable term of the related lease when collectability is reasonably assured. Rental income includes a de minimus amount of amortization of below market lease liabilities for the three and six months ended June 30, 2019 and June 30, 2018. The estimated aggregate future amortization of below market lease liabilities is $0.1 million for 2019, $0.1 million for 2020, $0.1 million for 2021, $0.1 million for 2022 and $0.1 million for 2023. Realization of the residual values of the assets under lease is dependent on the future ability to market the assets under prevailing market conditions. The lease is classified as an operating lease and the underlying leased assets are included in Property and Equipment (Note 10, "Property and Equipment").

Lease income related to operating leases for the three months ended June 30, 2019 and June 30, 2018 was $3.3 million and $3.3 million, respectively ($6.7 million year to date compared to $6.7 million prior year to date).

The following table provides the net book value of operating lease property included in property and equipment in the consolidated balance sheets:

(in thousands)	As of June 30, 2019
Property leased to lessees	113,008
Accumulation depreciation	(12,271		)
Net property and equipment leased	$	100,737

As of June 30, 2019, future undiscounted cash flows to be received in each of the next five years and thereafter, on non-cancelable operating leases are as follows:

(in thousands)
2019	$	5,840
2020	11,832
2021	12,099
2022	12,371
2023	12,649
Thereafter	149,896

LEASES

LEASES

Financial Statement Impact of Adopting Accounting Standards Update No. 2016-02 "Leases (Topic 842)" ("ASU 2016-02" or "ASC 842")

The Company adopted ASU 2016-02 on January 1, 2019 using the modified retrospective adoption method. The reported results for 2019 reflect the adoption of ASC 842 guidance while the reported results for 2018 were prepared and continue to be reported under the guidance of ASC 840, Leases, referred to herein as "previous guidance."

ASC 842 provides guidance for both lessees and lessors. The Company is the lessee where it leases certain office properties from lessors. The Company is the lessor when it leases certain property to lessees.

The guidance requires lessees to recognize right-of-use assets and lease liabilities in the balance sheet and disclose key information about leasing arrangements, such as information about variable lease payments and options to renew and terminate leases. The amended guidance will require both operating and finance leases to be recognized in the balance sheet. A lessee should recognize in the statement of financial position a liability to make lease payments (the lease liability) and a right-of-use asset ("ROU") representing its right to use the underlying asset for the lease term.

The guidance requires lessors to classify leases as a sales-type, direct financing, or operating lease. A lease is classified as a sales-type lease if any one of five criteria are met, each of which indicate that the lease, in effect, transfers control of the underlying asset to the lessee. If none of those five criteria are met, but two additional criteria are both met, indicating that the lessor has transferred substantially all the risks and benefits of the underlying asset to the lessee and a third party, the lease is classified as a direct financing lease. All leases that are not classified as sales-type or direct financing leases are classified as operating leases.

The Company elected certain of the practical expedients that are permitted under the transition guidance which allowed the Company to carryforward the historical lease classification, not reassess initial direct costs for any existing leases as of January 1, 2019 or reassess whether any expired or existing contracts are or contain leases. In addition, the Company elected to adopt the “hindsight” practical expedient to determine the reasonably certain lease term for existing leases. The Company has revised its relevant policies and procedures, as applicable, to meet the new accounting, reporting and disclosure requirements of ASC 842 and have updated internal controls accordingly.

The main difference between the guidance in ASU 2016-02 and prior guidance for lessees is the recognition of right-of-use assets and lease liabilities for those leases classified as operating leases. Recognition of the right-of-use assets and liabilities had a material impact to the Company’s consolidated balance sheet upon adoption. However, since all its leases are operating leases under ASC 840 and the Company will carryforward the historical lease classification, the new standard did not have a material impact on the Company’s consolidated statements of operations, consolidated statements of shareholder’s equity, or consolidated statements of cash flows.

The adoption resulted in an increase of the ROU assets of approximately $2.7 million and lease liabilities of $2.9 million. The difference of $0.2 million relates to straight-line rent accruals and lease incentive liabilities that were reclassified to ROU assets for operating leases.

The main difference between the guidance in ASU 2016-02 and prior guidance for lessors is a modification of what qualifies as a sales-type and direct financing lease. All the Company’s lessor leases are classified as operating leases.

Lease Accounting Policy

The Company determines lease classification at commencement date. Leases not classified as sales-type (lessor) or financing leases (lessor and lessee) are classified as operating leases. The primary accounting criteria the Company uses that results in operating lease classification are: (a) the lease does not transfer ownership of the underlying asset to the lessee by the end of the lease term, (b) the lease does not grant the lessee a purchase option that the lessee is reasonably certain to exercise, (c) using a seventy-five percent or more threshold, the lease term is not for a major part of the remaining economic life of the underlying asset, (d) using a ninety percent or more threshold, the present value of the sum of the lease payments and residual value guarantee from the lessee does not equal or substantially exceeds all of the fair value of the underlying asset.

Rental income from operating leases is recognized on a straight-line basis, based on contractual lease terms with fixed and determinable increases over the non-cancellable term of the related lease when collectability is reasonably assured. Rental expense for operating leases is recognized on a straight-line basis over the lease term, net of any applicable lease incentive amortization.

Lessee Leases

The Company has operating leases for office space which include fixed base rent payments, as well as variable rent payments to reimburse the landlord for operating expenses and taxes. The Company’s variable lease payments do not depend on a published index or rate, and therefore, are expensed as incurred. The Company includes only fixed payments for lease components in the measurement of the right-of-use asset and lease liability. There are no residual value guarantees. The Company does not currently have leases that meet the finance lease classification as defined under ASC 842.

The Company treats contracts as a lease when the contract: (1) conveys the right to use a physically distinct asset for a period of time in exchange for consideration, (2) the Company directs the use of the asset and (3) the Company obtains substantially all the economic benefits of the asset. Right-of-use assets and lease liabilities are measured and recognized based on the present value of the future minimum lease payments over the lease term at the commencement date. As the Company’s leases are office leases, the Company is unable to determine an implicit rate; therefore, the Company uses its incremental borrowing rate based on the information available at the lease commencement date in determining the present value of future payments for those leases. The Company includes options to extend or terminate the lease in the measurement of the right-of-use asset and lease liability when it is reasonably certain that such options will be exercised. Lease expense for minimum lease payments is recognized on a straight-line basis over the lease term.

As an accounting policy, the Company has elected not to apply the recognition requirements in ASC 842 to short-term leases (generally those with terms of twelve months or less). Instead, the Company recognizes the lease payments as expense on a straight-line basis over the lease term and any variable lease payments in the period in which the obligation for those payments is incurred.

The ROU assets and lease liability are presented as separate line items on the face of the Company’s consolidated balance sheet as of June 30, 2019.

Operating lease costs and variable lease costs included in selling and administrative costs for the three months ended June 30, 2019 were $0.2 million and de minimis, respectively. Operating lease costs and variable lease costs included in selling and administrative costs for the six months ended June 30, 2019 were $0.5 million and de minimis, respectively.

The annual maturities of lease liabilities as of June 30, 2019 were as follows:

(in thousands)	Lease Commitments
2019	$	463
2020	377
2021	388
2022	399
2023	422
2024 and thereafter	859
Total undiscounted lease payments	2,908
Imputed interest	498
Total lease liabilities	$	2,410

The weighted-average remaining lease term for our operating leases was 6.40 years as of June 30, 2019. The weighted average discount rate of our operating leases was 5.69% as of June 30, 2019. Cash paid for amounts included in the measurement of lease liabilities was $0.5 million for the six months ended June 30, 2019.

Lessor Leases

The Company owns a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property") that is subject to a long-term triple net lease agreement with an unrelated third-party. The lease provides for future rent escalations and renewal options. The initial lease term ends in May 2034. The lessee bears the cost of maintenance and property taxes. Rental income from operating leases is recognized on a straight-line basis, based on contractual lease terms with fixed and determinable increases over the non-cancellable term of the related lease when collectability is reasonably assured. Rental income includes a de minimus amount of amortization of below market lease liabilities for the three and six months ended June 30, 2019 and June 30, 2018. The estimated aggregate future amortization of below market lease liabilities is $0.1 million for 2019, $0.1 million for 2020, $0.1 million for 2021, $0.1 million for 2022 and $0.1 million for 2023. Realization of the residual values of the assets under lease is dependent on the future ability to market the assets under prevailing market conditions. The lease is classified as an operating lease and the underlying leased assets are included in Property and Equipment (Note 10, "Property and Equipment").

Lease income related to operating leases for the three months ended June 30, 2019 and June 30, 2018 was $3.3 million and $3.3 million, respectively ($6.7 million year to date compared to $6.7 million prior year to date).

The following table provides the net book value of operating lease property included in property and equipment in the consolidated balance sheets:

(in thousands)	As of June 30, 2019
Property leased to lessees	113,008
Accumulation depreciation	(12,271		)
Net property and equipment leased	$	100,737

As of June 30, 2019, future undiscounted cash flows to be received in each of the next five years and thereafter, on non-cancelable operating leases are as follows:

(in thousands)
2019	$	5,840
2020	11,832
2021	12,099
2022	12,371
2023	12,649
Thereafter	149,896

XML

Deferred Acquisition Costs

6 Months Ended

Jun. 30, 2019

Deferred Policy Acquisition Costs Disclosures [Abstract]

DEFERRED ACQUISITION COSTS

DEFERRED ACQUISITION COSTS

Deferred acquisition costs consist primarily of commissions and agency expenses incurred related to successful efforts to acquire vehicle service agreements and are amortized over the period in which the related revenues are earned in accordance with ASC 606.

The components of deferred acquisition costs and the related amortization expense for the three and six months ended June 30, 2019 and June 30, 2018 are comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Beginning balance, net	$	7,220		$	6,428		$	6,904		$	6,325
Additions	1,500			1,256			2,701			2,498
Amortization	(996		)	(1,022		)	(1,881		)	(2,161		)
Balance at June 30, net	$	7,724		$	6,662		$	7,724		$	6,662

XML

Recently Issued Accounting Standards

6 Months Ended

Jun. 30, 2019

Accounting Policies [Abstract]

RECENTLY ISSUED ACCOUNTING STANDARDS

RECENTLY ISSUED ACCOUNTING STANDARDS

(a)    Adoption of New Accounting Standards:

Effective January 1, 2018, the Company adopted Accounting Standards Update ("ASU") 2014-09, Revenue from Contracts with Customers ("ASU 2014-09"), and the related amendments, utilizing the modified retrospective approach, which created a new comprehensive revenue recognition standard that serves as the single source of revenue guidance for all contracts with customers to transfer goods or services or contracts for the transfer of nonfinancial assets, unless those contracts are within the scope of other standards. The core principle of ASU 2014-09 is that an entity recognizes revenue to depict the transfer of promised goods or services to customers in an amount that reflects the consideration to which the entity expects to be entitled in exchange for those goods or services. Insurance contracts, lease contracts and investments are not within the scope of ASU 2014-09. ASU 2014-09 is applicable to the Company's service fee and commission income. Service fee and commission income represents vehicle service agreement fees, GAP commissions, maintenance support service fees, warranty product commissions, homebuilder warranty service fees and homebuilder warranty commissions based on terms of various agreements with credit unions, consumers, businesses and homebuilders. With the exception of GAP commissions and homebuilder warranty service fees, the adoption of ASU 2014-09 did not change the way the Company recognized revenue for the year ended December 31, 2018. The new guidance affects IWS' GAP commissions and PWSC's homebuilder warranty service fees, which will be recognized more slowly as compared to the historic revenue recognition pattern prior to the Company’s adoption of ASU 2014-09. As a result of the adoption of ASU 2014-09, the Company also recorded a cumulative effect adjustment to increase accumulated deficit by $0.6 million and increase deferred service fees by $0.6 million. Prior periods have not been restated to conform to the current presentation. Refer to Note 15, "Revenue from Contracts with Customers," for further details.

Effective January 1, 2018, the Company adopted ASU 2016-01, Financial Instruments-Overall (Subtopic 825-10): Recognition and Measurement of Financial Assets and Financial Liabilities ("ASU 2016-01").The amendments in ASU 2016-01 address certain aspects of recognition, measurement, presentation, and disclosure of financial instruments. Most significantly, ASU 2016-01 requires (1) equity investments (except those accounted for under the equity method of accounting or those that result in consolidation of an investee) to be measured at fair value with changes in fair value recognized in net income (loss); however, an entity may choose to measure equity investments that do not have readily determinable fair values at cost, adjusted for observable price changes and impairments; and (2) an entity to present separately in other comprehensive income (loss) the portion of the total change in the fair value of a liability resulting from a change in the instrument-specific credit risk when the entity has elected to measure the liability at fair value in accordance with the fair value option for financial instruments. The Companyhas electedto measure its investments in private companies at cost, adjusted for observable price changes and impairments. Previously, the Company recorded its equity investments at fair value with net unrealized gains or losses reported in accumulated other comprehensive income (loss) and its subordinated debt at fair value with the total change in fair value reported in net income (loss). As a result of the adoption of ASU 2016-01, at January 1, 2018 cumulative net unrealized losses on equity investments of $0.0 million were reclassified from accumulated other comprehensive income (loss) into accumulated deficit and a cumulative $40.5 million change in fair value of subordinated debt attributable to instrument-specific credit risk was reclassified from accumulated deficit to accumulated other comprehensive income (loss). Prior periods have not been restated to conform to the current presentation.

Effective January 1, 2018, the Company adopted ASU 2016-15, Classification of Certain Cash Receipts and Cash Payments ("ASU 2016-15"). The objective of ASU 2016-15 is to reduce diversity in the classification of cash receipts and payments for specific cash flow issues, including debt prepayment or debt extinguishment costs, contingent consideration payments made after a business combination and proceeds from the settlement of insurance claims. The adoption of the standard did not affect the Company's consolidated statements of cash flows.

Effective January 1, 2018, the Company adopted ASU 2016-18, Statement of Cash Flows (Topic 230) Restricted Cash ("ASU 2016-18"). The objective of ASU 2016-18 is to explain the change during the period in the total cash, cash equivalents and amounts generally described as restricted cash or restricted cash equivalents.  Amounts generally described as restricted cash and cash equivalents should be included with the cash and cash equivalents when reconciling the beginning of period and end of period total amounts shown on the statement of cash flows.  As a result of the adoption of the standard, the change in restricted cash is included in the consolidated statements of cash flows.

Effective July 1, 2018, the Company adopted ASU 2018-07, Compensation-Stock Compensation (Topic 718): Improvements to Nonemployee Share-Based Payment Accounting ("ASU 2018-07"). ASU 2018-07 was issued to simplify the accounting for share-based transactions by expanding the scope of Topic 718 from only being applicable to share-based payments to employees to also include share-based payment transactions for acquiring goods and services from nonemployees. During the third quarter of 2018, the Company granted restricted common stock awards to a nonemployee. Refer to Note 18, "Stock-Based Compensation," for further details.

Effective January 1, 2019, the Company adopted ASU 2016-02, Leases ("ASU 2016-02").ASU 2016-02 was issued to improve the financial reporting of leasing transactions. Under current guidance for lessees, leases are only included on the balance sheet if certain criteria, classifying the agreement as a capital lease, are met. This update requires the recognition of a right-of-use asset and a corresponding lease liability, discounted to the present value, for all leases that extend beyond 12 months. For operating leases, the asset and liability will be amortized over the lease term on a straight-line basis, with all cash flows included within operating activities in the statement of cash flows. The accounting treatment for lessors will remain relatively unchanged. The Company adopted ASU 2016-02 using the modified retrospective transition method and did not restate comparative periods. The adoption had a significant effect on the Company's consolidated balance sheet. Refer to Note 14, "Leases," for further information regarding the adoption of ASU 2016-02.

(b)    Accounting Standards Not Yet Adopted:

In June 2016, the FASB issued ASU 2016-13, Financial Instruments-Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments ("ASU 2016-13"). ASU 2016-13 replaces the current incurred loss model used to measure impairment losses with an expected loss model for trade, reinsurance, and other receivables as well as financial instruments measured at amortized cost. ASU 2016-13 will require a financial asset measured at amortized cost, including reinsurance balances recoverable, to be presented at the net amount expected to be collected by means of an allowance for credit losses that runs through net loss. Credit losses relating to available-for-sale debt securities will also be recorded through an allowance for credit losses. However, the amendments would limit the amount of the allowance to the amount by which fair value is below amortized cost. The measurement of credit losses on available-for-sale investments is similar under current GAAP, but the update requires the use of the allowance account through which amounts can be reversed, rather than through irreversible write-downs. On November 15, 2019, the FASB issued ASU 2019-10, which (1) provides a framework to stagger effective dates for future major accounting standards and (2) amends the effective dates for certain major new accounting standards to give implementation relief to certain types of entities. Specifically, per ASU 2019-10 the Company would adopt ASU 2016-13 beginning January 1, 2023, as the Company is considered to be a smaller reporting company. The Company is currently evaluating ASU 2016-13 to determine the potential impact that adopting this standard will have on its consolidated financial statements.

In January 2017, the FASB issued ASU 2017-04, Intangibles - Goodwill and Other (Topic 350): Simplifying the Test for Goodwill Impairment ("ASU 2017-04"). ASU 2017-04 was issued to simplify the subsequent measurement of goodwill. This update changes the impairment test by requiring an entity to compare the fair value of a reporting unit with its carrying amount as opposed to comparing the carrying amount of goodwill with its implied fair value. ASU 2017-04 is effective for annual and interim reporting periods beginning after December 15, 2019. Early adoption is permitted. The Company does not believe the adoption of ASU 2017-04 will have a material effect on its consolidated financial statements.

In October 2018, the FASB issued ASU 2018-17, Consolidation (Topic 810): Targeted Improvements to Related Party Guidance for Variable Interest Entities ("ASU 2018-17"). Among other things, ASU 2018-17 changes how all entities that apply the variable interest entity ("VIE") guidance evaluate decision making fees. Under ASU 2018-17, when an entity determines whether a decision-making fee is a variable interest, it considers indirect interests held through related parties under common control on a proportionate basis rather than in their entirety. The new approach is consistent with how indirect interests held by related parties under common control are evaluated when determining whether a reporting entity is the primary beneficiary of a VIE. ASU 2018-17 is effective for annual and interim reporting periods beginning after December 15, 2019. Early adoption is permitted. The Company is currently evaluating ASU 2018-17 to determine the potential impact that adopting this standard will have on its consolidated financial statements.

XML

Deferred Acquisition Costs (Tables)

6 Months Ended

Jun. 30, 2019

Deferred Policy Acquisition Costs Disclosures [Abstract]

Components of Deferred Acquisition Costs and Amortization Expense

The components of deferred acquisition costs and the related amortization expense for the three and six months ended June 30, 2019 and June 30, 2018 are comprised as follows:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Beginning balance, net	$	7,220		$	6,428		$	6,904		$	6,325
Additions	1,500			1,256			2,701			2,498
Amortization	(996		)	(1,022		)	(1,881		)	(2,161		)
Balance at June 30, net	$	7,724		$	6,662		$	7,724		$	6,662

XML

Fair Value of Financial Instruments

6 Months Ended

Jun. 30, 2019

Fair Value Disclosures [Abstract]

FAIR VALUE OF FINANCIAL INSTRUMENTS

FAIR VALUE OF FINANCIAL INSTRUMENTS

Fair value is the price that would be received upon sale of an asset or paid to transfer a liability in an orderly transaction between market participants at the measurement date. Fair value is best evidenced by quoted bid or ask price, as appropriate, in an active market. Where bid or ask prices are not available, such as in an illiquid or inactive market, the closing price of the most recent transaction of that instrument subject to appropriate adjustments as required is used. Where quoted market prices are not available, the quoted prices of similar financial instruments or valuation models with observable market-based inputs are used to estimate the fair value. These valuation models may use multiple observable market inputs, including observable interest rates, foreign exchange rates, index levels, credit spreads, equity prices, counterparty credit quality, corresponding market volatility levels and option volatilities. Minimal management judgment is required for fair values calculated using quoted market prices or observable market inputs for models. Greater subjectivity is required when making valuation adjustments for financial instruments in inactive markets or when using models where observable parameters do not exist. Also, the calculation of estimated fair value is based on market conditions at a specific point in time and may not be reflective of future fair values. For the Company's financial instruments carried at cost or amortized cost, the book value is not adjusted to reflect increases or decreases in fair value due to market fluctuations, including those due to interest rate changes, as it is the Company's intention to hold them until there is a recovery of fair value, which may be to maturity.

The Company employs a fair value hierarchy to categorize the inputs it uses in valuation techniques to measure the fair value. The following fair value hierarchy is used in selecting inputs, with the highest priority given to Level 1:

• Level 1 – Quoted prices for identical instruments in active markets.

• Level 2 – Quoted prices for similar instruments in active markets; quoted prices for identical or similar instruments in markets that are not active; and model-derived valuations in which all significant inputs are observable in active markets.

• Level 3 – Valuations derived from valuation techniques in which one or more significant inputs are not observable.

The Company classifies its investments in fixed maturities as available-for-sale and reports these investments at fair value. The Company's equity investments, limited liability investments, at fair value, real estate investments and subordinated debt are measured and reported at fair value.

Fixed maturities - Fair values of fixed maturities for which no active market exists are derived from quoted market prices of similar instruments or other third party evidence. All classes of the Company’s fixed maturities, primarily consisting of investments in US. Treasury bills and government bonds; obligations of states, municipalities and political subdivisions; mortgage-backed securities; and corporate securities, are classified as Level 2. Level 2 is applied to valuations based upon quoted prices for similar assets in active markets; quoted prices for identical or similar assets in markets that are inactive; or valuations based on models where the significant inputs are observable or can be corroborated by observable market data.

The Company engages a third-party vendor who utilizes third-party pricing sources and primarily employs a market approach to determine the fair values of our fixed maturities. The market approach includes primarily obtaining prices from independent third-party pricing services as well as, to a lesser extent, quotes from broker-dealers. Our third-party vendor also monitors market indicators, as well as industry and economic events, to ensure pricing is appropriate. All classes of our fixed maturities are valued using this technique. The Company has obtained an understanding of our third-party vendor’s valuation methodologies and inputs. Fair values obtained from our third-party vendor are not adjusted by the Company.

The following is a description of the significant inputs, by asset class, used by the third-party pricing services to determine the fair values of our fixed maturities included in Level 2:

• U.S. government, government agencies and authorities are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets and maturity.

• States, municipalities and political subdivisions are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, new issuances and credit spreads.

• Mortgage-backed securities are generally priced using the market approach. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, expected prepayments, expected credit default rates, delinquencies and issue specific information including, but not limited to, collateral type, seniority and vintage.

• Corporate securities are generally priced using the market approach using pricing vendors. Inputs generally consist of trades of identical or similar securities, quoted prices in inactive markets, issuer rating, benchmark yields, maturity and credit spreads.

Equity investments - Fair values of equity investments, including warrants, reflect quoted market values based on latest bid prices, where active markets exist, or models based on significant market observable inputs, where no active markets exist.

Limited liability investments, at fair value - Limited liability investments, at fair valueinclude the Company's investment in 1347 Investors as well as the underlying investments of Net Lease and Argo Holdings. 1347 Investors owns common stock in Limbach Holdings, Inc., a publicly traded company. Net Lease owns investments in limited liability companies that hold investment properties. Argo Holdings makes investments in limited liability companies and limited partnerships that hold investments in search funds and private operating companies.

• The fair value of the Company's investment in 1347 Investors is calculated based on a model that distributes the net equity of 1347 Investors to all classes of membership interests. The model uses quoted market prices and significant market observable inputs. This investment is categorized in Level 2 of the fair value hierarchy.

• The fair value of Net Lease's investments in limited liability companies is based upon the net asset values of the underlying investments companies as a practical expedient to estimate fair value. The Company applies the net asset value practical expedient to Net Lease's limited liability investments on an investment-by-investment basis unless it is probable that the Company will sell a portion of an investment at an amount different from the net asset value of the investment. Investments that are measured at fair value using the net asset value practical expedient are not required to be classified using the fair value hierarchy.

• The fair value of Argo Holdings' limited liability investments that hold investments in search funds is based on the initial investment in the search funds. The fair value of Argo Holdings' limited liability investments that hold investments in private operating companies is valued using a market approach including valuation multiples applied to corresponding performance metrics, such as earnings before interest, tax, depreciation and amortization; revenue; or net earnings. The selected valuation multiples were estimated using multiples provided by the investees and review of those multiples in light of investor updates, performance reports, financial statements and other relevant information. These investments are categorized in Level 3 of the fair value hierarchy.

Real estate investments - The fair value of real estate investments involves a combination of the market and income valuation techniques. Under this approach, a market-based capitalization rate is derived from comparable transactions, adjusted for any unique characteristics of each asset, and applied to the asset under consideration. The cap rates used during underwriting and subsequent valuation incorporate the consideration of risks of vacancy and collection loss, administrative costs of owning net leased assets and possible capital expenditures that could be determined a landlord expense. These investments are categorized in Level 3 of the fair value hierarchy.

Subordinated debt - The fair value of the subordinated debt is calculated using a model based on significant market observable inputs and inputs developed by a third party. These inputs include credit spread assumptions developed by a third party and market observable swap rates. The subordinated debt is categorized in Level 2 of the fair value hierarchy.

Warrant liability- As described in Note 13, "Debt," the Company issued the KWH Warrants on March 1, 2019. The KWH Warrants are measured and reported at fair value and are included in accrued expenses and other liabilities in the consolidated balance sheets. The fair value of the warrant liability is estimated using an internal model without relevant observable market inputs. The significant inputs used in the model include an enterprise value multiple applied to earnings before interest, tax, depreciation and amortization. The implied enterprise value is reduced by the remaining debt associated with the KWH Loan to determine an implied equity value. The liability classified warrants are categorized in Level 3 of the fair value hierarchy.

Assets and Liabilities Measured at Fair Value on a Recurring Basis

The balances of the Company's financial assets and liabilities measured at fair value on a recurring basis by level within the fair value hierarchy as of June 30, 2019 and December 31, 2018 are as follows. Certain investments in limited liability companies that are measured at fair value using the net asset value practical expedient are not required to be classified using the fair value hierarchy, but are presented in the following tables to permit reconciliation of the fair value hierarchy to the amounts presented in the consolidated balance sheets:

(in thousands)					June 30, 2019
	Fair Value Measurements at the End of the Reporting Period Using
	Total		Quoted Prices in Active Markets for Identical Assets (Level 1)		Significant Other Observable Inputs (Level 2)		Significant Unobservable Inputs (Level 3)		Measured at Net Asset Value
Recurring fair value measurements:
Assets:
Fixed maturities:
U.S. government, government agencies and authorities	$	15,046	$	—	$	15,046	$	—	$	—
States, municipalities and political subdivisions	601		—		601		—		—
Mortgage-backed	2,454		—		2,454		—		—
Corporate	2,686		—		2,686		—		—
Total fixed maturities	20,787		—		20,787		—		—
Equity investments:
Common stock	179		179		—		—		—
Warrants	23		16		7		—		—
Total equity investments	202		195		7		—		—
Limited liability investments, at fair value	33,047		—		6,298		4,635		22,114
Real estate investments	10,662		—		—		10,662		—
Other investments	895		—		895		—		—
Short-term investments	154		—		154		—		—
Total assets	$	65,747	$	195	$	28,141	$	15,297	$	22,114
Liabilities:
Subordinated debt	$	50,224	$	—	$	50,224	$	—	$	—
Warrant liability	307		—		—		307		—
Total liabilities	$	50,531	$	—	$	50,224	$	307	$	—

(in thousands)					December 31, 2018
			Fair Value Measurements at the End of the Reporting Period Using
	Total		Quoted Prices in Active Markets for Identical Assets (Level 1)		Significant Other Observable Inputs (Level 2)		Significant Unobservable Inputs (Level 3)		Measured at Net Asset Value
Recurring fair value measurements:
Assets:
Fixed maturities:
U.S. government, government agencies and authorities	$	5,547	$	—	$	5,547	$	—	$	—
States municipalities and political subdivisions	607		—		607		—		—
Mortgage-backed	3,186		—		3,186		—		—
Corporate	2,920		—		2,920		—		—
Total fixed maturities	12,260		—		12,260		—		—
Equity investments:
Common stock	801		801		—		—		—
Warrants	55		19		36		—		—
Total equity investments	856		820		36		—		—
Limited liability investments, at fair value	26,015		—		206		4,124		21,685
Real estate investments	10,662		—		—		10,662		—
Other investments	2,079		—		2,079		—		—
Short-term investments	152		—		152		—		—
Total assets	$	52,024	$	820	$	14,733	$	14,786	$	21,685
Liabilities:
Subordinated debt	$	50,023	$	—	$	50,023	$	—	$	—
Total liabilities	$	50,023	$	—	$	50,023	$	—	$	—

The following table provides a reconciliation of the fair value of recurring Level 3 fair value measurements for the three and six months ended June 30, 2019 and June 30, 2018:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Assets:
Limited liability investments, at fair value:
Beginning balance	$	4,060		$	1,634		$	4,124		$	1,397
Purchases	599			504			674			978
Distributions received	(14		)	(70		)	(338		)	(562		)
Realized gains included in net (loss) income	14			—			83			251
Change in fair value of limited liability investments, at fair value included in net (loss) income	(24		)	15			92			19
Ending balance	$	4,635		$	2,083		$	4,635		$	2,083
Unrealized gains recognized in net (loss) income on limited liability investments, at fair value held at end of period	$	—		$	15		$	116		$	38
Real estate investments:
Beginning balance	$	10,662		$	10,662		$	10,662		$	10,662
Change in fair value of real estate investments included in net (loss) income	—			—			—			—
Ending balance	$	10,662		$	10,662		$	10,662		$	10,662
Unrealized gains recognized in net (loss) income on real estate investments held at end of period	$	—		$	—		$	—		$	—
Ending balance - assets	$	15,297		$	12,745		$	15,297		$	12,745
Liabilities:
Warrant liability:
Beginning balance	$	317		$	—		$	—		$	—
Issuance of warrants	—			—			361			—
Change in fair value of warrant liability included in net (loss) income	(10		)	—			(54		)	—
Ending balance - liabilities	$	307		$	—		$	307		$	—
Unrealized gains recognized in net (loss) income on warrant liability held at end of period	$	(10	)	$	—		$	(54	)	$	—

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's investments that are categorized as Level 3 at June 30, 2019 :

Categories	Fair Value		Valuation Techniques	Unobservable Inputs	Input Value(s)
Limited liability investments, at fair value	$	4,635	Market approach	Valuation multiples	5.0x-8.8x
Real estate investments	$	10,662	Market and income approach	Cap rates	7.5	%
Warrant liability	$	307	Market approach	Valuation multiple	6.0x

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's investments that are categorized as Level 3 at December 31, 2018:

Categories	Fair Value		Valuation Techniques	Unobservable Inputs	Input Value(s)
Limited liability investments, at fair value	$	4,124	Market approach	Valuation multiples	5.0x-8.8x
Real estate investments	$	10,662	Market and income approach	Cap rates	7.5	%

All transfers are recognized by the Company at the beginning of each reporting period. Transfers between Levels 2 and 3 generally relate to whether significant unobservable inputs are used for the fair value measurements. There were no transfers between levels in 2019 or 2018.

Investments Measured Using the Net Asset Value per Share Practical Expedient

The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at June 30, 2019:

Category	Fair Value (in thousands)		Unfunded Commitments	Redemption Frequency	Redemption Notice Period
Limited liability investments, at fair value	$	22,114	n/a	n/a	n/a

The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at December 31, 2018:

Category	Fair Value (in thousands)		Unfunded Commitments	Redemption Frequency	Redemption Notice Period
Limited liability investments, at fair value	$	21,685	n/a	n/a	n/a

Assets and Liabilities Measured at Fair Value on a Nonrecurring Basis

Certain assets and liabilities are measured at fair value on a nonrecurring basis, including assets that are adjusted for observable price changes or written down to fair value as a result of an impairment. For the three months ended June 30, 2019 and June 30, 2018, the Company recorded adjustments to increase the fair value of an certain investments in private companies for observable price changes of zero and $0.2 million, respectively, ($0.0 million and $0.2 million for the six months ended June 30, 2019 and June 30, 2018, respectively), which are included in net change in unrealized gain (loss) on private company investments in the consolidated statements of operations. The Company recorded no write-downs for other-than-temporary impairments related to investments in private companies for the three and six months ended June 30, 2019 and June 30, 2018. To determine the fair value of investments in these private companies, the Company considered rounds of financing and third-party transactions, discounted cash flow analyses and market-based information, including comparable transactions, trading multiples and changes in market outlook, among other factors. The Company has classified the fair value measurements of these investments in private companies as Level 3 because they involve significant unobservable inputs.

As further discussed in Note 5, "Acquisition and Discontinued Operations," the Company acquired Geminus on March 1, 2019. The fair values of intangible assets and deferred service fees associated with the acquisition of Geminus were determined to be Level 3 under the fair value hierarchy. The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for these Level 3 measurements:

Categories	Fair Value		Valuation Techniques	Unobservable Inputs	Input Value(s)
Customer relationships	$	3,732	Multi-period excess earnings	Growth rate	3.0	%
				Attrition rate	20.0	%
				Discount rate	13.0	%
Trade names	$	1,974	Relief from royalty	Royalty rate	0.25% - 2.0%
				Discount rate	13.0	%
Deferred service fees - Penn	$	8,734	Bottom-up	Normal profit margin	15.5	%
				Total direct costs	70.3	%
				Discount rate	5.0	%
Deferred service fees - Prime	$	1,830	Bottom-up	Normal profit margin	8.5	%
				Total direct costs	69.8	%
				Discount rate	5.0	%

XML

Recently Issued Accounting Standards (Policies)

6 Months Ended

Jun. 30, 2019

Accounting Policies [Abstract]

Accounting Standards

Adoption of New Accounting Standards:

Effective January 1, 2018, the Company adopted Accounting Standards Update ("ASU") 2014-09, Revenue from Contracts with Customers ("ASU 2014-09"), and the related amendments, utilizing the modified retrospective approach, which created a new comprehensive revenue recognition standard that serves as the single source of revenue guidance for all contracts with customers to transfer goods or services or contracts for the transfer of nonfinancial assets, unless those contracts are within the scope of other standards. The core principle of ASU 2014-09 is that an entity recognizes revenue to depict the transfer of promised goods or services to customers in an amount that reflects the consideration to which the entity expects to be entitled in exchange for those goods or services. Insurance contracts, lease contracts and investments are not within the scope of ASU 2014-09. ASU 2014-09 is applicable to the Company's service fee and commission income. Service fee and commission income represents vehicle service agreement fees, GAP commissions, maintenance support service fees, warranty product commissions, homebuilder warranty service fees and homebuilder warranty commissions based on terms of various agreements with credit unions, consumers, businesses and homebuilders. With the exception of GAP commissions and homebuilder warranty service fees, the adoption of ASU 2014-09 did not change the way the Company recognized revenue for the year ended December 31, 2018. The new guidance affects IWS' GAP commissions and PWSC's homebuilder warranty service fees, which will be recognized more slowly as compared to the historic revenue recognition pattern prior to the Company’s adoption of ASU 2014-09. As a result of the adoption of ASU 2014-09, the Company also recorded a cumulative effect adjustment to increase accumulated deficit by $0.6 million and increase deferred service fees by $0.6 million. Prior periods have not been restated to conform to the current presentation. Refer to Note 15, "Revenue from Contracts with Customers," for further details.

Effective January 1, 2018, the Company adopted ASU 2016-01, Financial Instruments-Overall (Subtopic 825-10): Recognition and Measurement of Financial Assets and Financial Liabilities ("ASU 2016-01").The amendments in ASU 2016-01 address certain aspects of recognition, measurement, presentation, and disclosure of financial instruments. Most significantly, ASU 2016-01 requires (1) equity investments (except those accounted for under the equity method of accounting or those that result in consolidation of an investee) to be measured at fair value with changes in fair value recognized in net income (loss); however, an entity may choose to measure equity investments that do not have readily determinable fair values at cost, adjusted for observable price changes and impairments; and (2) an entity to present separately in other comprehensive income (loss) the portion of the total change in the fair value of a liability resulting from a change in the instrument-specific credit risk when the entity has elected to measure the liability at fair value in accordance with the fair value option for financial instruments. The Companyhas electedto measure its investments in private companies at cost, adjusted for observable price changes and impairments. Previously, the Company recorded its equity investments at fair value with net unrealized gains or losses reported in accumulated other comprehensive income (loss) and its subordinated debt at fair value with the total change in fair value reported in net income (loss). As a result of the adoption of ASU 2016-01, at January 1, 2018 cumulative net unrealized losses on equity investments of $0.0 million were reclassified from accumulated other comprehensive income (loss) into accumulated deficit and a cumulative $40.5 million change in fair value of subordinated debt attributable to instrument-specific credit risk was reclassified from accumulated deficit to accumulated other comprehensive income (loss). Prior periods have not been restated to conform to the current presentation.

Effective January 1, 2018, the Company adopted ASU 2016-15, Classification of Certain Cash Receipts and Cash Payments ("ASU 2016-15"). The objective of ASU 2016-15 is to reduce diversity in the classification of cash receipts and payments for specific cash flow issues, including debt prepayment or debt extinguishment costs, contingent consideration payments made after a business combination and proceeds from the settlement of insurance claims. The adoption of the standard did not affect the Company's consolidated statements of cash flows.

Effective January 1, 2018, the Company adopted ASU 2016-18, Statement of Cash Flows (Topic 230) Restricted Cash ("ASU 2016-18"). The objective of ASU 2016-18 is to explain the change during the period in the total cash, cash equivalents and amounts generally described as restricted cash or restricted cash equivalents.  Amounts generally described as restricted cash and cash equivalents should be included with the cash and cash equivalents when reconciling the beginning of period and end of period total amounts shown on the statement of cash flows.  As a result of the adoption of the standard, the change in restricted cash is included in the consolidated statements of cash flows.

Effective July 1, 2018, the Company adopted ASU 2018-07, Compensation-Stock Compensation (Topic 718): Improvements to Nonemployee Share-Based Payment Accounting ("ASU 2018-07"). ASU 2018-07 was issued to simplify the accounting for share-based transactions by expanding the scope of Topic 718 from only being applicable to share-based payments to employees to also include share-based payment transactions for acquiring goods and services from nonemployees. During the third quarter of 2018, the Company granted restricted common stock awards to a nonemployee. Refer to Note 18, "Stock-Based Compensation," for further details.

Effective January 1, 2019, the Company adopted ASU 2016-02, Leases ("ASU 2016-02").ASU 2016-02 was issued to improve the financial reporting of leasing transactions. Under current guidance for lessees, leases are only included on the balance sheet if certain criteria, classifying the agreement as a capital lease, are met. This update requires the recognition of a right-of-use asset and a corresponding lease liability, discounted to the present value, for all leases that extend beyond 12 months. For operating leases, the asset and liability will be amortized over the lease term on a straight-line basis, with all cash flows included within operating activities in the statement of cash flows. The accounting treatment for lessors will remain relatively unchanged. The Company adopted ASU 2016-02 using the modified retrospective transition method and did not restate comparative periods. The adoption had a significant effect on the Company's consolidated balance sheet. Refer to Note 14, "Leases," for further information regarding the adoption of ASU 2016-02.

(b)    Accounting Standards Not Yet Adopted:

In June 2016, the FASB issued ASU 2016-13, Financial Instruments-Credit Losses (Topic 326): Measurement of Credit Losses on Financial Instruments ("ASU 2016-13"). ASU 2016-13 replaces the current incurred loss model used to measure impairment losses with an expected loss model for trade, reinsurance, and other receivables as well as financial instruments measured at amortized cost. ASU 2016-13 will require a financial asset measured at amortized cost, including reinsurance balances recoverable, to be presented at the net amount expected to be collected by means of an allowance for credit losses that runs through net loss. Credit losses relating to available-for-sale debt securities will also be recorded through an allowance for credit losses. However, the amendments would limit the amount of the allowance to the amount by which fair value is below amortized cost. The measurement of credit losses on available-for-sale investments is similar under current GAAP, but the update requires the use of the allowance account through which amounts can be reversed, rather than through irreversible write-downs. On November 15, 2019, the FASB issued ASU 2019-10, which (1) provides a framework to stagger effective dates for future major accounting standards and (2) amends the effective dates for certain major new accounting standards to give implementation relief to certain types of entities. Specifically, per ASU 2019-10 the Company would adopt ASU 2016-13 beginning January 1, 2023, as the Company is considered to be a smaller reporting company. The Company is currently evaluating ASU 2016-13 to determine the potential impact that adopting this standard will have on its consolidated financial statements.

In January 2017, the FASB issued ASU 2017-04, Intangibles - Goodwill and Other (Topic 350): Simplifying the Test for Goodwill Impairment ("ASU 2017-04"). ASU 2017-04 was issued to simplify the subsequent measurement of goodwill. This update changes the impairment test by requiring an entity to compare the fair value of a reporting unit with its carrying amount as opposed to comparing the carrying amount of goodwill with its implied fair value. ASU 2017-04 is effective for annual and interim reporting periods beginning after December 15, 2019. Early adoption is permitted. The Company does not believe the adoption of ASU 2017-04 will have a material effect on its consolidated financial statements.

In October 2018, the FASB issued ASU 2018-17, Consolidation (Topic 810): Targeted Improvements to Related Party Guidance for Variable Interest Entities ("ASU 2018-17"). Among other things, ASU 2018-17 changes how all entities that apply the variable interest entity ("VIE") guidance evaluate decision making fees. Under ASU 2018-17, when an entity determines whether a decision-making fee is a variable interest, it considers indirect interests held through related parties under common control on a proportionate basis rather than in their entirety. The new approach is consistent with how indirect interests held by related parties under common control are evaluated when determining whether a reporting entity is the primary beneficiary of a VIE. ASU 2018-17 is effective for annual and interim reporting periods beginning after December 15, 2019. Early adoption is permitted. The Company is currently evaluating ASU 2018-17 to determine the potential impact that adopting this standard will have on its consolidated financial statements.

Lease Accounting Policy

Lease Accounting Policy

The Company determines lease classification at commencement date. Leases not classified as sales-type (lessor) or financing leases (lessor and lessee) are classified as operating leases. The primary accounting criteria the Company uses that results in operating lease classification are: (a) the lease does not transfer ownership of the underlying asset to the lessee by the end of the lease term, (b) the lease does not grant the lessee a purchase option that the lessee is reasonably certain to exercise, (c) using a seventy-five percent or more threshold, the lease term is not for a major part of the remaining economic life of the underlying asset, (d) using a ninety percent or more threshold, the present value of the sum of the lease payments and residual value guarantee from the lessee does not equal or substantially exceeds all of the fair value of the underlying asset.

The Company has operating leases for office space which include fixed base rent payments, as well as variable rent payments to reimburse the landlord for operating expenses and taxes. The Company’s variable lease payments do not depend on a published index or rate, and therefore, are expensed as incurred. The Company includes only fixed payments for lease components in the measurement of the right-of-use asset and lease liability. There are no residual value guarantees. The Company does not currently have leases that meet the finance lease classification as defined under ASC 842.

The Company treats contracts as a lease when the contract: (1) conveys the right to use a physically distinct asset for a period of time in exchange for consideration, (2) the Company directs the use of the asset and (3) the Company obtains substantially all the economic benefits of the asset. Right-of-use assets and lease liabilities are measured and recognized based on the present value of the future minimum lease payments over the lease term at the commencement date. As the Company’s leases are office leases, the Company is unable to determine an implicit rate; therefore, the Company uses its incremental borrowing rate based on the information available at the lease commencement date in determining the present value of future payments for those leases. The Company includes options to extend or terminate the lease in the measurement of the right-of-use asset and lease liability when it is reasonably certain that such options will be exercised. Lease expense for minimum lease payments is recognized on a straight-line basis over the lease term.

As an accounting policy, the Company has elected not to apply the recognition requirements in ASC 842 to short-term leases (generally those with terms of twelve months or less). Instead, the Company recognizes the lease payments as expense on a straight-line basis over the lease term and any variable lease payments in the period in which the obligation for those payments is incurred.

Lease Accounting Policy

Rental income from operating leases is recognized on a straight-line basis, based on contractual lease terms with fixed and determinable increases over the non-cancellable term of the related lease when collectability is reasonably assured. Rental expense for operating leases is recognized on a straight-line basis over the lease term, net of any applicable lease incentive amortization.

XML

Consolidated Statements of Cash Flows - USD ($) $ in Thousands	3 Months Ended		6 Months Ended		12 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018	Dec. 31, 2018	Dec. 31, 2017
Operating activities:
Net income (loss)	$ (396)	$ (10,296)	$ 2,793	$ (12,514)
Adjustments to reconcile net income (loss) to net cash used in operating activities:
Income from discontinued operations, net of taxes	0	(594)	0	(980)
Loss on disposal of discontinued operations, net of taxes	0	6,628	0	6,628
Equity in net (income) loss of investee	(201)	385	(168)	284
Equity in net income of limited liability investments			(14)	(181)
Depreciation and amortization expense			3,373	2,678
Stock-based compensation expense, net of forfeitures			386	588
Net realized losses (gains)	556	(132)	241	(397)
Gain on change in fair value of equity investments	63	421	(15)	(744)
(Gain) loss on change in fair value of limited liability investments, at fair value	2,347	(525)	6,612	(1,461)
Net change in unrealized (gain) loss on private company investments			(19)	155
(Gain) loss on change in fair value of debt			(1,494)	1,061
Deferred income taxes, adjusted for Geminus liabilities assumed			(816)	56
Other-than-temporary impairment loss			75	0
Amortization of fixed maturities premiums and discounts			(7)	32
Amortization of note payable premium			(461)	(473)
Gain on disposal of subsidiary			0	(17)
Changes in operating assets and liabilities:
Service fee receivable, net, adjusted for Geminus assets acquired			(1,299)	(787)
Other receivables, net, adjusted for Geminus assets acquired			(1,019)	(1,617)
Deferred acquisition costs, net			(820)	(337)
Unpaid loss and loss adjustment expenses			(136)	1,265
Deferred service fees, adjusted for Geminus liabilities assumed			3,828	3,255
Other, net, adjusted for Geminus assets acquired and liabilities assumed			(270)	(3,566)
Cash used in operating activities - continuing operations			(2,454)	(4,150)
Cash used in operating activities - discontinued operations			0	(1,909)
Cash used in operating activities - discontinued operations			(2,454)	(6,059)
Investing activities:
Proceeds from sales and maturities of fixed maturities			5,887	4,965
Proceeds from sales of equity investments			675	3,704
Purchases of fixed maturities			(9,794)	(1,885)
Purchases of equity investments			0	(806)
Net proceeds from limited liability investments			282	2,199
Net purchases of limited liability investments, at fair value			(336)	(666)
Net proceeds from investments in private companies			249	95
Net proceeds from other investments			1,239	405
Net proceeds from short-term investments			30	0
Proceeds from disposal of subsidiary			0	565
Net proceeds from sale of discontinued operations			0	1,129
Acquisition of business, net of cash acquired			(4,792)	0
Net disposals of property and equipment, adjusted for Geminus assets acquired			(134)	593
Cash (used in) provided by investing activities - continuing operations			(6,694)	10,298
Cash used in investing activities - discontinued operations			0	(3,086)
Net cash (used in) provided by investing activities			(6,694)	7,212
Financing activities:
Taxes paid related to net share settlements of restricted stock awards			(89)	0
Principal proceeds from bank loan, net of debt issuance costs of $981			9,019	0
Principal payments on bank loans			(1,325)	(500)
Principal payments on notes payable			(1,816)	(1,632)
Cash provided by (used in) financing activities - continuing operations			5,789	(2,132)
Cash used in financing activities - discontinued operations			0	0
Net cash provided by (used in) financing activities			5,789	(2,132)
Net (decrease) increase in cash and cash equivalents and restricted cash from continuing operations			(3,359)	4,016
Cash and cash equivalents and restricted cash at beginning of period					$ 31,578	$ 43,874
Less: cash and cash equivalents and restricted cash of discontinued operations at beginning of period					0	$ 23,512
Cash and cash equivalents and restricted cash of continuing operations at beginning of period			31,578	20,362	20,362
Cash and cash equivalents and restricted cash of continuing operations at end of period	$ 28,219	$ 24,378	$ 28,219	$ 24,378	$ 31,578

XML

Acquisition and Discontinued Operations - Schedule of Estimated Fair Values of Assets Acquired and Liabilities Assumed (Details) - USD ($) $ in Thousands	Mar. 01, 2019	Jun. 30, 2019	Dec. 31, 2018
Business Acquisition [Line Items]
Goodwill		$ 82,104	$ 74,659
Other assets	$ 620	5,394	4,459
Deferred service fees		$ 16,518	$ 14,786
Geminus
Business Acquisition [Line Items]
Investments	4,405
Cash and cash equivalents	755
Restricted cash	2,650
Accrued investment income	32
Service fee receivable	513
Other receivables	12
Property and equipment, net	79
Goodwill	7,445
Total assets	22,217
Accrued expenses and other liabilities	2,018
Income taxes payable	1
Deferred service fees	10,564
Net deferred income tax liabilities	1,263
Total liabilities	13,846
Purchase price	8,371
Geminus | Customer relationships
Business Acquisition [Line Items]
Intangible asset subject to amortization - customer relationships	3,732
Geminus | Trade names
Business Acquisition [Line Items]
Intangible assets not subject to amortization - trade names	$ 1,974

XML

Fair Value of Financial Instruments (Tables)

6 Months Ended

Jun. 30, 2019

Fair Value Disclosures [Abstract]

Schedule of Financial Assets and Liabilities Measured at Fair Value on Recurring Basis

June 30, 2019 and December 31, 2018 are as follows. Certain investments in limited liability companies that are measured at fair value using the net asset value practical expedient are not required to be classified using the fair value hierarchy, but are presented in the following tables to permit reconciliation of the fair value hierarchy to the amounts presented in the consolidated balance sheets:

(in thousands)					June 30, 2019
	Fair Value Measurements at the End of the Reporting Period Using
	Total		Quoted Prices in Active Markets for Identical Assets (Level 1)		Significant Other Observable Inputs (Level 2)		Significant Unobservable Inputs (Level 3)		Measured at Net Asset Value
Recurring fair value measurements:
Assets:
Fixed maturities:
U.S. government, government agencies and authorities	$	15,046	$	—	$	15,046	$	—	$	—
States, municipalities and political subdivisions	601		—		601		—		—
Mortgage-backed	2,454		—		2,454		—		—
Corporate	2,686		—		2,686		—		—
Total fixed maturities	20,787		—		20,787		—		—
Equity investments:
Common stock	179		179		—		—		—
Warrants	23		16		7		—		—
Total equity investments	202		195		7		—		—
Limited liability investments, at fair value	33,047		—		6,298		4,635		22,114
Real estate investments	10,662		—		—		10,662		—
Other investments	895		—		895		—		—
Short-term investments	154		—		154		—		—
Total assets	$	65,747	$	195	$	28,141	$	15,297	$	22,114
Liabilities:
Subordinated debt	$	50,224	$	—	$	50,224	$	—	$	—
Warrant liability	307		—		—		307		—
Total liabilities	$	50,531	$	—	$	50,224	$	307	$	—

(in thousands)					December 31, 2018
			Fair Value Measurements at the End of the Reporting Period Using
	Total		Quoted Prices in Active Markets for Identical Assets (Level 1)		Significant Other Observable Inputs (Level 2)		Significant Unobservable Inputs (Level 3)		Measured at Net Asset Value
Recurring fair value measurements:
Assets:
Fixed maturities:
U.S. government, government agencies and authorities	$	5,547	$	—	$	5,547	$	—	$	—
States municipalities and political subdivisions	607		—		607		—		—
Mortgage-backed	3,186		—		3,186		—		—
Corporate	2,920		—		2,920		—		—
Total fixed maturities	12,260		—		12,260		—		—
Equity investments:
Common stock	801		801		—		—		—
Warrants	55		19		36		—		—
Total equity investments	856		820		36		—		—
Limited liability investments, at fair value	26,015		—		206		4,124		21,685
Real estate investments	10,662		—		—		10,662		—
Other investments	2,079		—		2,079		—		—
Short-term investments	152		—		152		—		—
Total assets	$	52,024	$	820	$	14,733	$	14,786	$	21,685
Liabilities:
Subordinated debt	$	50,023	$	—	$	50,023	$	—	$	—
Total liabilities	$	50,023	$	—	$	50,023	$	—	$	—

Schedule of Reconciliation of Fair Value of Recurring Level 3 Measurements

The following table provides a reconciliation of the fair value of recurring Level 3 fair value measurements for the three and six months ended June 30, 2019 and June 30, 2018:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Assets:
Limited liability investments, at fair value:
Beginning balance	$	4,060		$	1,634		$	4,124		$	1,397
Purchases	599			504			674			978
Distributions received	(14		)	(70		)	(338		)	(562		)
Realized gains included in net (loss) income	14			—			83			251
Change in fair value of limited liability investments, at fair value included in net (loss) income	(24		)	15			92			19
Ending balance	$	4,635		$	2,083		$	4,635		$	2,083
Unrealized gains recognized in net (loss) income on limited liability investments, at fair value held at end of period	$	—		$	15		$	116		$	38
Real estate investments:
Beginning balance	$	10,662		$	10,662		$	10,662		$	10,662
Change in fair value of real estate investments included in net (loss) income	—			—			—			—
Ending balance	$	10,662		$	10,662		$	10,662		$	10,662
Unrealized gains recognized in net (loss) income on real estate investments held at end of period	$	—		$	—		$	—		$	—
Ending balance - assets	$	15,297		$	12,745		$	15,297		$	12,745
Liabilities:
Warrant liability:
Beginning balance	$	317		$	—		$	—		$	—
Issuance of warrants	—			—			361			—
Change in fair value of warrant liability included in net (loss) income	(10		)	—			(54		)	—
Ending balance - liabilities	$	307		$	—		$	307		$	—
Unrealized gains recognized in net (loss) income on warrant liability held at end of period	$	(10	)	$	—		$	(54	)	$	—

Schedule of Fair Value Valuation Techniques Used to Measure Investments

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's investments that are categorized as Level 3 at June 30, 2019 :

Categories	Fair Value		Valuation Techniques	Unobservable Inputs	Input Value(s)
Limited liability investments, at fair value	$	4,635	Market approach	Valuation multiples	5.0x-8.8x
Real estate investments	$	10,662	Market and income approach	Cap rates	7.5	%
Warrant liability	$	307	Market approach	Valuation multiple	6.0x

The following table summarizes the valuation techniques and significant unobservable inputs utilized in determining fair values for the Company's investments that are categorized as Level 3 at December 31, 2018:

Categories	Fair Value		Valuation Techniques	Unobservable Inputs	Input Value(s)
Limited liability investments, at fair value	$	4,124	Market approach	Valuation multiples	5.0x-8.8x
Real estate investments	$	10,662	Market and income approach	Cap rates	7.5	%

Schedule of Investments at Fair Value Using Net Asset Value Per Share as Practical Expedient

The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at June 30, 2019:

Category	Fair Value (in thousands)		Unfunded Commitments	Redemption Frequency	Redemption Notice Period
Limited liability investments, at fair value	$	22,114	n/a	n/a	n/a

The following table summarizes investments for which fair value is measured using the net asset value per share practical expedient at December 31, 2018:

Category	Fair Value (in thousands)		Unfunded Commitments	Redemption Frequency	Redemption Notice Period
Limited liability investments, at fair value	$	21,685	n/a	n/a	n/a

XML

Investments - Amortized Cost, Gross Unrealized Gains and Losses, and Estimated Fair Value (Details) - USD ($) $ in Thousands	Jun. 30, 2019	Dec. 31, 2018
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	$ 20,771	$ 12,432
Gross Unrealized Gains	64	1
Gross Unrealized Losses	48	173
Estimated Fair Value	20,787	12,260
U.S. government, government agencies and authorities
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	15,007	5,594
Gross Unrealized Gains	52	1
Gross Unrealized Losses	13	48
Estimated Fair Value	15,046	5,547
States, municipalities and political subdivisions
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	604	621
Gross Unrealized Gains	1	0
Gross Unrealized Losses	4	14
Estimated Fair Value	601	607
Mortgage-backed
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	2,474	3,256
Gross Unrealized Gains	2	0
Gross Unrealized Losses	22	70
Estimated Fair Value	2,454	3,186
Corporate
Debt Securities, Available-for-sale [Line Items]
Amortized Cost	2,686	2,961
Gross Unrealized Gains	9	0
Gross Unrealized Losses	9	41
Estimated Fair Value	$ 2,686	$ 2,920

XML

Consolidated Statements of Operations - USD ($) shares in Thousands, $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Revenues:
Service fee and commission income	$ 11,772	$ 8,860	$ 21,587	$ 18,511
Rental income	3,341	3,345	6,682	6,693
Other income	113	108	258	321
Total revenues	15,226	12,313	28,527	25,525
Operating expenses:
Claims authorized on vehicle service agreements	2,506	1,392	4,393	2,764
Loss and loss adjustment expenses	601	1,301	708	1,647
Commissions	1,103	834	2,021	1,747
Cost of services sold	1,160	1,464	2,519	3,716
General and administrative expenses	9,164	7,295	17,566	14,771
Leased real estate segment interest expense	1,520	1,546	3,047	3,098
Total operating expenses	16,054	13,832	30,254	27,743
Operating loss	(828)	(1,519)	(1,727)	(2,218)
Other revenues (expenses), net:
Net investment income	749	1,010	1,448	1,648
Net realized (losses) gains	(556)	132	(241)	397
(Loss) gain on change in fair value of equity investments	(63)	(421)	15	744
Gain (loss) on change in fair value of limited liability investments, at fair value	2,347	(525)	6,612	(1,461)
Net change in unrealized gain (loss) on private company investments	0	(155)	19	(155)
Other-than-temporary impairment loss	0	0	(75)	0
Non-operating other income	19	14	173	21
Interest expense not allocated to segments	(2,339)	(1,844)	(4,441)	(3,561)
Amortization of intangible assets	(676)	(254)	(1,197)	(509)
Gain (loss) on change in fair value of debt	918	(142)	1,494	(1,061)
Gain on disposal of subsidiary	0	17	0	17
Equity in net income (loss) of investee	201	(385)	168	(284)
Total other revenues (expenses), net	600	(2,553)	3,975	(4,204)
(Loss) income from continuing operations before income tax expense (benefit)	(228)	(4,072)	2,248	(6,422)
Income tax expense (benefit)	168	190	(545)	444
(Loss) income from continuing operations	(396)	(4,262)	2,793	(6,866)
Income from discontinued operations, net of taxes	0	594	0	980
Loss on disposal of discontinued operations, net of taxes	0	(6,628)	0	(6,628)
Net (loss) income	(396)	(10,296)	2,793	(12,514)
Less: net income attributable to noncontrolling interests in consolidated subsidiaries	258	158	469	517
Less: dividends on preferred stock, net of tax	252	259	498	512
Net (loss) income attributable to common shareholders	$ (906)	$ (10,713)	$ 1,826	$ (13,543)
(Loss) earnings per share - continuing operations:
Basic (in dollars per share)	$ (0.04)	$ (0.22)	$ 0.08	$ (0.36)
Diluted (in dollars per share)	(0.04)	(0.22)	0.08	(0.36)
Loss per share - discontinued operations:
Basic (in dollars per share)	0.00	(0.28)	0.00	(0.26)
Diluted (in dollars per share)	0.00	(0.28)	0.00	(0.26)
(Loss) earnings per share – net (loss) income attributable to common shareholders:
Basic (in dollars per share)	(0.04)	(0.49)	0.08	(0.62)
Diluted (in dollars per share)	$ (0.04)	$ (0.49)	$ 0.08	$ (0.62)
Weighted-average shares outstanding (in ‘000s):
Basic (in shares)	21,867	21,708	21,854	21,708
Diluted (in shares)	21,867	21,708	21,854	21,708

XML

- Atlas Financial Holdings, Inc. (Details) $ in Millions	Nov. 30, 2010 USD ($) employee	Jun. 30, 2019 USD ($)
Related Party Transactions [Abstract]
Number of employees | employee	5
Notes receivable, related parties	$ 1.1	$ 0.7
Receivable interest rate	3.00%
Market value of pledged shares		$ 0.0

XML

Leases - Lease payments and receipts (Details) $ in Thousands	Jun. 30, 2019 USD ($)
Operating Leases, Future Minimum Payments Receivable [Abstract]
2019	$ 5,840
2020	11,832
2021	12,099
2022	12,371
2023	12,649
Thereafter	$ 149,896

XML

Vehicle Service Agreement Liability - Reconciliation of the Changes in the Vehicle Service Agreement (Details) - USD ($) $ in Thousands	6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018
Movement in Standard Product Warranty Accrual [Roll Forward]
Recognition of service fees on vehicle service agreements	$ (7,900)
Vehicle service agreement fees
Movement in Standard Product Warranty Accrual [Roll Forward]
Balance at January 1, net	43,734	$ 40,794
Vehicle service agreement liability acquired during the year related to the purchase of Geminus	10,792	0
Gross service fees for vehicle service agreements sold	14,549	11,166
Recognition of service fees on vehicle service agreements	(12,703)	(9,588)
Liability for claims authorized on vehicle service agreements	4,393	2,764
Payments of claims authorized on vehicle service agreements	(2,678)	(2,950)
Re-estimation of deferred service fees	(321)	(165)
Balance at June 30, net	$ 57,766	$ 42,021

XML

Debt - Additional Information (Details) - USD ($)			3 Months Ended		6 Months Ended
	Jan. 30, 2020	Mar. 01, 2019	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018	Dec. 31, 2018	Oct. 12, 2017	Jul. 31, 2016	Oct. 15, 2015	Jan. 05, 2015
Debt Instrument [Line Items]
Membership interest percentage exercisable by warrant		1.25%
Fair Value			$ 263,641,000		$ 263,641,000		$ 246,091,000
Long-term debt			258,937,000		258,937,000		253,256,000
Increase in fair value of subordinated debt					200,000
Change in fair value of debt attributable to instrument-specific credit risk			(750,000)	$ 778,000	(1,695,000)	$ 344,000
Gain (loss) on change in fair value of debt			918,000	$ (142,000)	1,494,000	$ (1,061,000)
Deferred interest payable			5,700,000		5,700,000
Bank loans
Debt Instrument [Line Items]
Fair Value			14,902,000		14,902,000		3,829,000
Long-term debt			11,674,000		11,674,000		3,917,000
Note payable
Debt Instrument [Line Items]
Fair Value			198,515,000		198,515,000		192,239,000
Long-term debt			197,039,000		197,039,000		199,316,000
Mortgage
Debt Instrument [Line Items]
Principal									$ 180,000,000
Fixed interest rate									4.07%
Fair Value			181,042,000		181,042,000		174,265,000		$ 191,700,000
Premium									$ 11,700,000
Long-term debt			180,484,000		180,484,000		182,548,000
PWSC Loan | Bank loans
Debt Instrument [Line Items]
Principal								$ 5,000,000.0
Fixed interest rate								5.00%
Fair Value			2,656,000		2,656,000		3,829,000
Long-term debt			2,717,000		2,717,000		3,917,000
KWH Loan | Bank loans
Debt Instrument [Line Items]
Principal		$ 10,000,000.0
Proceeds from issuance of debt		400,000
Debt instrument, unamortized discount (premium), net		$ 1,000,000
Fair Value			12,246,000		12,246,000		0
Long-term debt			8,957,000		8,957,000		0
KWH Loan | LIBOR | Bank loans
Debt Instrument [Line Items]
Basis on variable rate		9.25%
Flower Note | Note payable
Debt Instrument [Line Items]
Principal											$ 9,200,000
Fixed interest rate											4.81%
Fair Value			8,322,000		8,322,000		8,565,000
Long-term debt			7,555,000		7,555,000		7,768,000
Net Lease Note | Note payable
Debt Instrument [Line Items]
Principal										$ 9,000,000
Fixed interest rate										10.25%
Fair Value			9,151,000		9,151,000		9,409,000
Long-term debt			$ 9,000,000		$ 9,000,000		$ 9,000,000
Forecast | PWSC Loan | Bank loans
Debt Instrument [Line Items]
Repayments of debt	$ 300,000

XML

Income Taxes - Income Tax Expense (Benefit) (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Income Tax Disclosure [Abstract]
Income tax (benefit) expense at United States statutory income tax rate	$ (48)	$ (855)	$ 472	$ (1,348)
Valuation allowance	97	822	(1,234)	1,354
Non-deductible compensation	25	62	34	123
Disposition of subsidiary	(24)	0	(24)	0
State income tax	32	67	58	133
Change in unrecognized tax benefits	71	60	141	130
Indefinite life intangibles	54	24	87	46
Foreign operations subject to different tax rates	(20)	(39)	(17)	(54)
Other	(19)	49	(62)	60
Income tax expense (benefit)	$ 168	$ 190	$ (545)	$ 444

XML

Stock-Based Compensation (Tables)

6 Months Ended

Jun. 30, 2019

Share-based Payment Arrangement [Abstract]

Schedule of Stock Option Activity

The following table summarizes the stock option activity during the six months ended June 30, 2019:

	Number of Options Outstanding	Weighted-Average Exercise Price		Weighted-Average Remaining Contractual Term (in Years)	Aggregate Intrinsic Value (in Thousands)
Outstanding at December 31, 2018	40,000	$	4.67	1.3	$	—
Granted	—	—
Expired	—	—
Outstanding at June 30, 2019	40,000	$	4.67	0.8	$	—
Exercisable at June 30, 2019	40,000	$	4.67	0.8	$	—

Schedule of Unvested Restricted Stock Award Activity

The following table summarizes the activity related to unvested 2014 Restricted Stock Awards, 2018 Modified Restricted Stock Award, Modified Restricted Stock Award and 2018 Restricted Stock Award (collectively "Restricted Stock Awards") for the six months endedJune 30, 2019:

	Number of Restricted Stock Awards		Weighted-Average Grant Date Fair Value (per Share)
Unvested at December 31, 2018	1,092,450		$	4.51
Vested	(79,231	)	4.14
Cancelled for Tax Withholding	(36,269	)	4.14
Unvested at June 30, 2019	976,950		$	4.55

XML

Property and Equipment (Tables)

6 Months Ended

Jun. 30, 2019

Property, Plant and Equipment [Abstract]

Property and Equipment

Property and equipment at June 30, 2019 and December 31, 2018 are comprised as follows:

(in thousands)					June 30, 2019
	Total Property and Equipment							Property leased to others under operating leases included in property and equipment
	Cost		Accumulated Depreciation			Carrying Value		Cost		Accumulated Depreciation		Carrying Value
Land	$	21,120	$	—		$	21,120	$	21,120	$	—	$	21,120
Site improvements	91,308		12,228			79,080		91,308		12,228		79,080
Buildings	580		43			537		580		43		537
Leasehold improvements	149		103			46		—		—		—
Furniture and equipment	1,042		953			89		—		—		—
Computer hardware	5,289		4,983			306		—		—		—
Total	$	119,488	$	18,310		$	101,178	$	113,008	$	12,271	$	100,737

(in thousands)			December 31, 2018
	Total Property and Equipment							Property leased to others under operating leases included in property and equipment
	Cost			Accumulated Depreciation		Carrying Value		Cost		Accumulated Depreciation		Carrying Value
Land	$	21,120		$	—	$	21,120	$	21,120	$	—	$	21,120
Site improvements	91,308			10,161		81,147		91,308		10,161		81,147
Buildings	580			36		544		580		36		544
Leasehold improvements	104			102		2		—		—		—
Furniture and equipment	993			901		92		—		—		—
Computer hardware	4,995			4,758		237		—		—		—
Total	$	119,100		$	15,958	$	103,142	$	113,008	$	10,197	$	102,811

XML

Leases (Tables)

6 Months Ended

Jun. 30, 2019

Leases [Abstract]

Annual Maturities of Lease Liabilities

The annual maturities of lease liabilities as of June 30, 2019 were as follows:

(in thousands)	Lease Commitments
2019	$	463
2020	377
2021	388
2022	399
2023	422
2024 and thereafter	859
Total undiscounted lease payments	2,908
Imputed interest	498
Total lease liabilities	$	2,410

Schedule of Net Book Value of Operating Lease Property

The following table provides the net book value of operating lease property included in property and equipment in the consolidated balance sheets:

(in thousands)	As of June 30, 2019
Property leased to lessees	113,008
Accumulation depreciation	(12,271		)
Net property and equipment leased	$	100,737

Future Undiscounted Cash Flows to be Received

As of June 30, 2019, future undiscounted cash flows to be received in each of the next five years and thereafter, on non-cancelable operating leases are as follows:

(in thousands)
2019	$	5,840
2020	11,832
2021	12,099
2022	12,371
2023	12,649
Thereafter	149,896

XML

Related Parties - Fundamental Global Investors, LLC (Details) $ / shares in Units, $ / shares in Units, $ in Thousands, $ in Millions						6 Months Ended
	Jul. 30, 2018 USD ($) $ / shares shares	Jul. 30, 2018 CAD ($)	Mar. 15, 2018 USD ($) shares	Nov. 01, 2017 USD ($) shares	Oct. 25, 2017 USD ($) $ / shares shares	Jun. 30, 2019 USD ($)	Jun. 30, 2018 USD ($)	Jul. 30, 2018 $ / shares shares
Related Party Transaction [Line Items]
Proceeds from sales of equity investments						$ 675	$ 3,704
Management
Related Party Transaction [Line Items]
Stock issued (in shares) | shares				475,428	900,000
Share price (in dollars per share) | $ / shares					$ 7.85
Proceeds from sale of treasury stock				$ 3,700
Proceeds from sales of equity investments			$ 3,400
Common Stock | Management
Related Party Transaction [Line Items]
Effect on future cash flows					$ 7,100
Other shares (in shares) | shares			424,572
Common Stock | Management
Related Party Transaction [Line Items]
Effect on future cash flows	$ 500
Shares of investment (in shares) | shares	75,000							75,000
Sale of stock (in dollars per share) | $ / shares	$ 7.13
Corporate Segment
Related Party Transaction [Line Items]
Effect on future cash flows		$ 1.3
Shares of investment (in shares) | shares	1,813,889							1,813,889
Sale of stock (in dollars per share) | $ / shares								$ 0.72

XML

Fair Value of Financial Instruments - Financial Assets and Liabilities Measured at Fair Value on Recurring Basis (Details) - USD ($) $ in Thousands	Jun. 30, 2019	Mar. 31, 2019	Dec. 31, 2018	Jun. 30, 2018	Mar. 31, 2018	Dec. 31, 2017
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	$ 20,787		$ 12,260
Equity investments	202		856
Limited liability investments, at fair value	33,047		26,015
Real estate investments	10,662		10,662
Other investments	895		2,079
Short-term investments	154		152
Total assets	65,747		52,024
Subordinated debt, at fair value	50,224		50,023
Warrant liability	307
Total liabilities	50,531		50,023
U.S. government, government agencies and authorities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	15,046		5,547
States, municipalities and political subdivisions
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	601		607
Mortgage-backed
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	2,454		3,186
Corporate
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	2,686		2,920
Common Stock
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Equity investments	179		801
Warrants
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Equity investments	23		55
Quoted Prices in Active Markets for Identical Assets (Level 1)
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Equity investments	195		820
Limited liability investments, at fair value	0		0
Real estate investments	0		0
Other investments	0		0
Short-term investments	0		0
Total assets	195		820
Subordinated debt, at fair value	0		0
Warrant liability	0
Total liabilities	0		0
Quoted Prices in Active Markets for Identical Assets (Level 1) | U.S. government, government agencies and authorities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Quoted Prices in Active Markets for Identical Assets (Level 1) | States, municipalities and political subdivisions
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Quoted Prices in Active Markets for Identical Assets (Level 1) | Mortgage-backed
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Quoted Prices in Active Markets for Identical Assets (Level 1) | Corporate
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Quoted Prices in Active Markets for Identical Assets (Level 1) | Common Stock
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Equity investments	179		801
Quoted Prices in Active Markets for Identical Assets (Level 1) | Warrants
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Equity investments	16		19
Significant Other Observable Inputs (Level 2)
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	20,787		12,260
Equity investments	7		36
Limited liability investments, at fair value	6,298		206
Real estate investments	0		0
Other investments	895		2,079
Short-term investments	154		152
Total assets	28,141		14,733
Subordinated debt, at fair value	50,224		50,023
Warrant liability	0
Total liabilities	50,224		50,023
Significant Other Observable Inputs (Level 2) | U.S. government, government agencies and authorities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	15,046		5,547
Significant Other Observable Inputs (Level 2) | States, municipalities and political subdivisions
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	601		607
Significant Other Observable Inputs (Level 2) | Mortgage-backed
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	2,454		3,186
Significant Other Observable Inputs (Level 2) | Corporate
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	2,686		2,920
Significant Other Observable Inputs (Level 2) | Common Stock
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Equity investments	0		0
Significant Other Observable Inputs (Level 2) | Warrants
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Equity investments	7		36
Significant Unobservable Inputs (Level 3)
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Equity investments	0		0
Limited liability investments, at fair value	4,635	$ 4,060	4,124	$ 2,083	$ 1,634	$ 1,397
Real estate investments	10,662	10,662	10,662	10,662	10,662	10,662
Other investments	0		0
Short-term investments	0		0
Total assets	15,297		14,786	12,745
Subordinated debt, at fair value	0		0
Warrant liability	307	$ 317	0	$ 0	$ 0	$ 0
Total liabilities	307		0
Significant Unobservable Inputs (Level 3) | U.S. government, government agencies and authorities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Significant Unobservable Inputs (Level 3) | States, municipalities and political subdivisions
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Significant Unobservable Inputs (Level 3) | Mortgage-backed
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Significant Unobservable Inputs (Level 3) | Corporate
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Significant Unobservable Inputs (Level 3) | Common Stock
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Equity investments	0		0
Significant Unobservable Inputs (Level 3) | Warrants
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Equity investments	0		0
Measured at Net Asset Value
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Equity investments	0		0
Limited liability investments, at fair value	22,114		21,685
Real estate investments	0		0
Other investments	0		0
Short-term investments	0		0
Total assets	22,114		21,685
Subordinated debt, at fair value	0		0
Warrant liability	0
Total liabilities	0		0
Measured at Net Asset Value | U.S. government, government agencies and authorities
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Measured at Net Asset Value | States, municipalities and political subdivisions
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Measured at Net Asset Value | Mortgage-backed
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Measured at Net Asset Value | Corporate
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Fixed maturity securities	0		0
Measured at Net Asset Value | Common Stock
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Equity investments	0		0
Measured at Net Asset Value | Warrants
Fair Value, Assets Measured on Recurring Basis, Unobservable Input Reconciliation [Line Items]
Equity investments	$ 0		$ 0

XML

Deferred Acquisition Costs (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Deferred Acquisition Costs
Beginning balance, net	$ 7,220	$ 6,428	$ 6,904	$ 6,325
Additions	1,500	1,256	2,701	2,498
Amortization	(996)	(1,022)	(1,881)	(2,161)
Balance at June 30, net	$ 7,724	$ 6,662	$ 7,724	$ 6,662

XML

Investments - Gross Realized Gains and Losses on Fixed Maturities (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Investments [Abstract]
Gross realized gains	$ 44	$ 133	$ 359	$ 398
Gross realized losses	(600)	(1)	(600)	(1)
Net realized (losses) gains	$ (556)	$ 132	$ (241)	$ 397

XML

Fair Value of Financial Instruments Fair Value of Financial Instruments - Valuation Techniques and Significant Unobservable Inputs (Details) - Significant Unobservable Inputs (Level 3) $ in Thousands	Jun. 30, 2019 USD ($)
Multi-period excess earnings | Growth rate
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.030
Multi-period excess earnings | Attrition rate
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.200
Multi-period excess earnings | Discount rate
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.130
Relief from royalty | Discount rate
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.130
Minimum | Relief from royalty | Royalty rate
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.0025
Maximum | Relief from royalty | Royalty rate
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.020
Customer relationships
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Finite-lived intangible assets, fair value disclosure	$ 3,732
Trade names
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Indefinite-lived intangible assets (excluding goodwill), fair value disclosure	1,974
Deferred service fees - Penn
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Deferred service fee	$ 8,734
Deferred service fees - Penn | Bottom-up | Discount rate
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.050
Deferred service fees - Penn | Bottom-up | Normal profit margin
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.155
Deferred service fees - Penn | Bottom-up | Total direct costs
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.703
Deferred service fees - Prime
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Deferred service fee	$ 1,830
Deferred service fees - Prime | Bottom-up | Discount rate
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.050
Deferred service fees - Prime | Bottom-up | Normal profit margin
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.085
Deferred service fees - Prime | Bottom-up | Total direct costs
Fair Value Measurement Inputs and Valuation Techniques [Line Items]
Intangible asset, measurement input	0.698

XML

Accumulated Other Comprehensive Income - Reclassification out of AOCI (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Net realized gains	$ (556)	$ 132	$ (241)	$ 397
Other-than-temporary impairment loss	0	0	(75)	0
Income (loss) from continuing operations before income tax (benefit) expense	(228)	(4,072)	2,248	(6,422)
Income tax (benefit) expense	168	190	(545)	444
(Loss) income from continuing operations	(396)	(4,262)	2,793	(6,866)
Income from discontinued operations, net of taxes	0	594	0	980
Net (loss) income	(396)	(10,296)	2,793	(12,514)
Unrealized Gains (Losses) on Available-for-Sale Investments | Reclassification out of Accumulated Other Comprehensive Income
Reclassification Adjustment out of Accumulated Other Comprehensive Income [Line Items]
Net realized gains	(38)	5	(32)	8
Other-than-temporary impairment loss	0	0	0	0
Income (loss) from continuing operations before income tax (benefit) expense	(38)	5	(32)	8
Income tax (benefit) expense	0	0	0	0
(Loss) income from continuing operations	(38)	5	(32)	8
Income from discontinued operations, net of taxes	0	(1)	0	3
Net (loss) income	$ (38)	$ 4	$ (32)	$ 11

XML

Income Taxes

6 Months Ended

Jun. 30, 2019

Income Tax Disclosure [Abstract]

INCOME TAXES

INCOME TAXES

The Tax Cuts and Jobs Act (the "Tax Act") was enacted on December 22, 2017. The Tax Act makes broad and complex changes to the U.S. tax code, including a permanent reduction in the U.S. federal corporate income tax rate to 21% starting in 2018. Previously, the Company was subject to a 34% U.S. federal corporate income tax rate.

Income tax expense (benefit) for the three and six months ended June 30, 2019 and June 30, 2018 varies from the amount that would result by applying the applicable U.S. federal corporate income tax rate of 21% to loss from continuing operations before income tax expense (benefit). The following table summarizes the differences:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Income tax (benefit) expense at United States statutory income tax rate	$	(48	)	$	(855	)	$	472		$	(1,348	)
Valuation allowance	97			822			(1,234		)	1,354
Non-deductible compensation	25			62			34			123
Disposition of subsidiary	(24		)	—			(24		)	—
State income tax	32			67			58			133
Change in unrecognized tax benefits(1)	71			60			141			130
Indefinite life intangibles	54			24			87			46
Foreign operations subject to different tax rates	(20		)	(39		)	(17		)	(54		)
Other	(19		)	49			(62		)	60
Income tax expense (benefit)	$	168		$	190		$	(545	)	$	444
(1) Includes interest and penalty expense related to unrecognized tax benefits.

The Company maintains a valuation allowance for its gross deferred tax assets at June 30, 2019 and December 31, 2018. The Company's operations have generated substantial operating losses in prior years. These losses can be available to reduce income taxes that might otherwise be incurred on future taxable income; however, it is uncertain whether the Company will generate the taxable income necessary to utilize these losses or other reversing temporary differences. This uncertainty has caused management to place a full valuation allowance on its June 30, 2019 and December 31, 2018 net deferred tax asset, excluding the deferred income tax asset and liability amounts set forth in the paragraph below. In the quarter ended March 31, 2019, the Company released into income $0.8 million of its valuation allowance, as a result of its acquisition of Geminus, due to net deferred income tax liabilities that are expected to reverse during the period in which the Company will have deferred income tax assets available.

The Company carries net deferred income tax liabilities of $29.0 million and $28.5 million at June 30, 2019 and December 31, 2018, respectively. At June 30, 2019, $8.0 million relates to deferred income tax liabilities scheduled to reverse in periods after the expiration of the Company's consolidated U.S. net operating loss carryforwards, $21.7 million relates to deferred income tax liabilities associated with land and indefinite lived intangible assets, $0.6 million relates to deferred income tax assets associated with state income taxes and $0.1 million relates to deferred income tax assets associated with alternative minimum tax credits. At December 31, 2018, $8.0 million relates to deferred income tax liabilities scheduled to reverse in periods after the expiration of the Company's consolidated U.S. net operating loss carryforwards, $21.1 million relates to deferred income tax liabilities associated with land and indefinite lived intangible assets, $0.5 million relates to deferred income tax assets associated with state income taxes and $0.1 million relates to deferred income tax assets associated with alternative minimum tax credits. The Company considered a tax planning strategy in arriving at its December 31, 2018 net deferred income tax liabilities.

As of June 30, 2019 and December 31, 2018, the Company carried a liability for unrecognized tax benefits of $1.4 million and $1.4 million, respectively, which is included in income taxes payable in the consolidated balance sheets. The Company classifies interest and penalty accruals, if any, related to unrecognized tax benefits as income tax expense. The Company recorded income tax expense of $0.1 million and $0.1 million related to interest and penalty accruals for the three months ended June 30, 2019 and June 30, 2018, respectively ($0.1 million and $0.1 million for the six months ended June 30, 2019 and June 30, 2018, respectively). At June 30, 2019 and December 31, 2018, the Company carried an accrual for the payment of interest and penalties of $1.2 million and $1.1 million, respectively, included in income taxes payable in the consolidated balance sheets.

XML

Unpaid Loss and Loss Adjustment Expenses

6 Months Ended

Jun. 30, 2019

Insurance [Abstract]

UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES

UNPAID LOSS AND LOSS ADJUSTMENT EXPENSES

The establishment of the provision for unpaid loss and loss adjustment expenses is based on known facts and interpretation of circumstances and is, therefore, a complex and dynamic process influenced by a large variety of factors. These factors include the Company's experience with similar cases and historical trends involving loss payment patterns, pending levels of unpaid loss and loss adjustment expenses, product mix or concentration, loss severity and loss frequency patterns.

Other factors include the continually evolving and changing regulatory and legal environment; actuarial studies; professional experience and expertise of the Company's claims departments' personnel and independent adjusters retained to handle individual claims; the quality of the data used for projection purposes; existing claims management practices including claims-handling and settlement practices; the effect of inflationary trends on future loss settlement costs; court decisions; economic conditions; and public attitudes.

Consequently, the process of determining the provision for unpaid loss and loss adjustment expenses necessarily involves risks that the actual loss and loss adjustment expenses incurred by the Company will deviate, perhaps materially, from the estimates recorded.

The Company's evaluation of the adequacy of unpaid loss and loss adjustment expenses includes a re-estimation of the liability for unpaid loss and loss adjustment expenses relating to each preceding financial year compared to the liability that was previously established.

The results of this comparison and the changes in the provision for unpaid loss and loss adjustment expenses, net of amounts recoverable from reinsurers, as of June 30, 2019 and June 30, 2018 were as follows:

(in thousands)	June 30, 2019			June 30, 2018
Balance at beginning of period, gross	$	2,073		$	1,329
Less reinsurance recoverable related to unpaid loss and loss adjustment expenses	—			72
Balance at beginning of period, net	2,073			1,257
Incurred related to:
Current year	—			—
Prior years	708			1,647
Paid related to:
Current year	—			—
Prior years	(844		)	(410		)
Balance at end of period, net	1,937			2,494
Plus reinsurance recoverable related to unpaid loss and loss adjustment expenses	—			100
Balance at end of period, gross	$	1,937		$	2,594

The Company reported unfavorable development on unpaid loss and loss adjustment expenses of $0.7 million and $1.6 million for the six months ended June 30, 2019 and June 30, 2018, respectively. The unfavorable development for the six months ended June 30, 2019 and June 30, 2018 was primarily related to an increase in loss and loss adjustment expenses at Amigo.

XML

Segmented Information

6 Months Ended

Jun. 30, 2019

Segment Reporting [Abstract]

SEGMENTED INFORMATION

SEGMENTED INFORMATION

The Company conducts its business through the following two reportable segments: Extended Warranty and Leased Real Estate.

The Company previously conducted its business through a third reportable segment, Insurance Underwriting. Insurance Underwriting included the following subsidiaries of the Company: Mendota, Amigo and Kingsway Reinsurance Corporation ("Kingsway Re"). As further discussed in Note 5, "Acquisition and Discontinued Operations," on October 18, 2018, the Company announced that it had completed the sale of Mendota. As a result, Mendota has been classified as discontinued operations and the results of their operations are reported separately for all periods presented. As a result of classifying Mendota as discontinued operations, the composition of the Insurance Underwriting segment has changed such that it no longer meets the criteria of a reportable segment. As such, all segmented information has been restated to exclude the Insurance Underwriting segment for all periods presented.

Extended Warranty Segment

Extended Warranty includes the following subsidiaries of the Company: IWS, Trinity, PWSC and Geminus (collectively, "Extended Warranty").

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by credit unions in 23 states and the District of Columbia to their members.

Trinity sells HVAC, standby generator, commercial LED lighting and refrigeration warranty products and provides equipment breakdown and maintenance support services to companies across the United States. As a seller of warranty products, Trinity markets and administers product warranty contracts for certain new and used products in the HVAC, standby generator, commercial LED lighting and refrigeration industries throughout the United States. Trinity acts as an agent on behalf of the third-party insurance companies that underwrite and guaranty these warranty contracts. Trinity does not guaranty the performance underlying the warranty contracts it sells. As a provider of equipment breakdown and maintenance support services, Trinity acts as a single point of contact to its clients for both certain equipment breakdowns and scheduled maintenance of equipment. Trinity will provide such repair and breakdown services by contracting with certain HVAC providers.

PWSC sells new home warranty products and provides administration services to home builders and homeowners across the United States. PWSC distributes its products and services through an in house sales team and through insurance brokers and insurance carriers throughout all states except Alaska and Louisiana.

Geminus sells vehicle service agreements and other finance and service products to used car buyers across the United States. Penn and Prime distribute these products via independent used car dealerships and franchised car dealerships, respectively.

Leased Real Estate Segment

Leased Real Estate includes the Company's subsidiary, CMC, which was acquired on July 14, 2016. CMC owns a parcel of real property consisting of approximately 192 acres located in the State of Texas (the "Real Property") that is leased to a third party pursuant to a long-term triple net lease. The Real Property is also subject to the Mortgage. When assessing and measuring the operational and financial performance of the Leased Real Estate segment, interest expense related to the Mortgage is included in Leased Real Estate's segment operating income.

Revenues and Operating Income by Reportable Segment

Results for the Company's reportable segments are based on the Company's internal financial reporting systems and are consistent with those followed in the preparation of the unaudited consolidated interim financial statements. The following tables provide financial data used by management. Segment assets are not allocated for management use and, therefore, are not included in the segment disclosures below.

Revenues by reportable segment reconciled to consolidated revenues for the three and six months ended June 30, 2019 and June 30, 2018 were:

(in thousands)	Three months ended June 30,				Six months ended June 30,
	2019		2018		2019		2018
Revenues:
Extended Warranty:
Service fee and commission income	$	11,772	$	8,860	$	21,587	$	18,511
Other income	41		36		116		102
Total Extended Warranty	11,813		8,896		21,703		18,613
Leased Real Estate:
Rental income	3,341		3,341		6,682		6,682
Other income	72		72		142		219
Total Leased Real Estate	3,413		3,413		6,824		6,901
Total segment revenues	15,226		12,309		28,527		25,514
Rental income not allocated to segments	—		4		—		11
Total revenues	$	15,226	$	12,313	$	28,527	$	25,525

The operating income by reportable segment in the following table is before income taxes and includes revenues and direct segment costs. Total segment operating income reconciled to the consolidated (loss) income from continuing operations for the three and six months ended June 30, 2019 and June 30, 2018 were:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Segment operating income:
Extended Warranty	$	1,035		$	1,090		$	1,602		$	1,936
Leased Real Estate	753			618			1,205			1,492
Total segment operating income	1,788			1,708			2,807			3,428
Net investment income	749			1,010			1,448			1,648
Net realized (losses) gains	(556		)	132			(241		)	397
(Loss) gain on change in fair value of equity investments	(63		)	(421		)	15			744
Gain (loss) on change in fair value of limited liability investments, at fair value	2,347			(525		)	6,612			(1,461		)
Net change in unrealized gain (loss) on private company investments	—			(155		)	19			(155		)
Other-than-temporary impairment loss	—			—			(75		)	—
Interest expense not allocated to segments	(2,339		)	(1,844		)	(4,441		)	(3,561		)
Other income and expenses not allocated to segments, net	(2,597		)	(3,213		)	(4,361		)	(5,625		)
Amortization of intangible assets	(676		)	(254		)	(1,197		)	(509		)
Gain (loss) on change in fair value of debt	918			(142		)	1,494			(1,061		)
Gain on disposal of subsidiary	—			17			—			17
Equity in net income (loss) of investee	201			(385		)	168			(284		)
(Loss) income from continuing operations before income tax expense (benefit)	(228		)	(4,072		)	2,248			(6,422		)
Income tax expense (benefit)	168			190			(545		)	444
(Loss) income from continuing operations	$	(396	)	$	(4,262	)	$	2,793		$	(6,866	)

XML

Vehicle Service Agreement Liability (Tables)

6 Months Ended

Jun. 30, 2019

Guarantees and Product Warranties [Abstract]

Schedule of Product Warranty Liability

A reconciliation of the changes in the vehicle service agreement liability, including deferred service fees related to vehicle service agreements, as of June 30, 2019 and June 30, 2018 were as follows:

(in thousands)	June 30, 2019			June 30, 2018
Balance at January 1, net	$	43,734		$	40,794
Vehicle service agreement liability acquired during the year related to the purchase of Geminus	10,792			—
Gross service fees for vehicle service agreements sold	14,549			11,166
Recognition of service fees on vehicle service agreements	(12,703		)	(9,588		)
Liability for claims authorized on vehicle service agreements	4,393			2,764
Payments of claims authorized on vehicle service agreements	(2,678		)	(2,950		)
Re-estimation of deferred service fees	(321		)	(165		)
Balance at June 30, net	$	57,766		$	42,021

Components of Vehicle Service Agreement Liability

The vehicle service agreement liability is presented as components of deferred services fees and accrued expenses and other liabilities in the consolidated balance sheets as follows:

(in thousands)	June 30,		December 31,
	2019		2018
Deferred service fees	$	57,182	$	43,495
Accrued expenses and other liabilities	584		239
Balance at end of period, net	$	57,766	$	43,734

XML

Revenue from Contracts with Customers (Tables)

6 Months Ended

Jun. 30, 2019

Revenue from Contract with Customer [Abstract]

Disaggregation of Revenue

The following table disaggregates revenues from contracts with customers by revenue type:

(in thousands)	Three months ended June 30,				Six months ended June 30,
	2019		2018		2019		2018
Vehicle service agreement fees - IWS	$	4,551	$	4,226	$	9,030	$	8,615
GAP commissions - IWS	226		200		484		392
Maintenance support service fees - Trinity	1,732		1,962		3,700		4,935
Warranty product commissions - Trinity	817		736		1,399		1,232
Homebuilder warranty service fees - PWSC	1,475		1,548		2,898		2,975
Homebuilder warranty commissions - PWSC	198		188		409		362
Vehicle service agreement fees - Geminus	2,757		—		3,644		—
GAP commissions - Geminus	16		—		23		—
Service fee and commission income	$	11,772	$	8,860	$	21,587	$	18,511

XML

Accumulated Other Comprehensive Income (Tables)

6 Months Ended

Jun. 30, 2019

Equity [Abstract]

Schedule of Accumulated Other Comprehensive Income (Loss)

On the other hand, the unaudited consolidated statements of comprehensive (loss) income present the components of other comprehensive (loss) income, net of tax, only for the three and six months ended June 30, 2019 and June 30, 2018 and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries.

(in thousands)	Three months ended June 30, 2019
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk			Equity in Other Comprehensive (Loss) Income of Limited Liability Investment			Total Accumulated Other Comprehensive Income
Balance at April 1, 2019	$	(61	)	$	(3,286	)	$	43,314		$	(45	)	$	39,922
Other comprehensive income (loss) arising during the period	115			—			(750		)	—			(635		)
Amounts reclassified from accumulated other comprehensive income	(7		)	—			—			45			38
Net current-period other comprehensive income (loss)	108			—			(750		)	45			(597		)
Balance at June 30, 2019	$	47		$	(3,286	)	$	42,564		$	—		$	39,325

(in thousands)	Three months ended June 30, 2018
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk		Total Accumulated Other Comprehensive Income
Balance at April 1, 2018	$	(891	)	$	(3,286	)	$	40,021	$	35,844
Other comprehensive income (loss) arising during the period	(72		)	—			778		706
Amounts reclassified from accumulated other comprehensive income	(4		)	—			—		(4		)
Net current-period other comprehensive income (loss)	(76		)	—			778		702
Balance at June 30, 2018	$	(967	)	$	(3,286	)	$	40,799	$	36,546

(in thousands)	Six months ended June 30, 2019
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk			Equity in Other Comprehensive (Loss) Income of Limited Liability Investment			Total Accumulated Other Comprehensive Income
Balance at January 1, 2019	$	(160	)	$	(3,286	)	$	44,259		$	(45	)	$	40,768
Other comprehensive income (loss) arising during the period	220			—			(1,695		)	—			(1,475		)
Amounts reclassified from accumulated other comprehensive income	(13		)	—			—			45			32
Net current-period other comprehensive income (loss)	207			—			(1,695		)	45			(1,443		)
Balance at June 30, 2019	$	47		$	(3,286	)	$	42,564		$	—		$	39,325

(in thousands)	Six months ended June 30, 2018
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk		Total Accumulated Other Comprehensive Income
Balance at January 1, 2018	$	(566	)	$	(3,286	)	$	—	$	(3,852	)
Cumulative effect of adoption of ASU 2016-01	40			—			40,455		40,495
Balance at January 1, 2018, as adjusted	(526		)	(3,286		)	40,455		36,643
Other comprehensive loss arising during the period	(430		)	—			344		(86		)
Amounts reclassified from accumulated other comprehensive income	(11		)	—			—		(11		)
Net current-period other comprehensive loss	(441		)	—			344		(97		)
Balance at June 30, 2018	$	(967	)	$	(3,286	)	$	40,799	$	36,546

Reclassification out of Accumulated Other Comprehensive Income

Components of accumulated other comprehensive income were reclassified to the following lines of the unaudited consolidated statements of operations for the three and six months ended June 30, 2019 and June 30, 2018:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Reclassification of accumulated other comprehensive income from unrealized gains (losses) on available-for-sale investments to:
Net realized (losses) gains	$	(38	)	$	5		$	(32	)	$	8
Other-than-temporary impairment loss	—			—			—			—
(Loss) income from continuing operations before income tax expense	(38		)	5			(32		)	8
Income tax expense	—			—			—			—
(Loss) income from continuing operations	(38		)	5			(32		)	8
Income from discontinued operations, net of taxes	—			(1		)	—			3
Net (loss) income	$	(38	)	$	4		$	(32	)	$	11

XML

Segmented Information - Segment (loss) income (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Segment Reporting Information [Line Items]
Total segment operating income	$ (828)	$ (1,519)	$ (1,727)	$ (2,218)
Net investment income	749	1,010	1,448	1,648
Net realized gains	(556)	132	(241)	397
(Loss) gain on change in fair value of equity investments	(63)	(421)	15	744
Gain (loss) on change in fair value of limited liability investments, at fair value	2,347	(525)	6,612	(1,461)
Net change in unrealized gain (loss) on private company investments	0	(155)	19	(155)
Other-than-temporary impairment loss	0	0	(75)	0
Interest expense not allocated to segments	(2,339)	(1,844)	(4,441)	(3,561)
Other income and expenses not allocated to segments, net	(2,597)	(3,213)	(4,361)	(5,625)
Amortization of intangible assets	(676)	(254)	(1,197)	(509)
Gain (loss) on change in fair value of debt	918	(142)	1,494	(1,061)
Gain on disposal of subsidiary	0	17	0	17
Equity in net income (loss) of investee	201	(385)	168	(284)
(Loss) income from continuing operations before income tax expense (benefit)	(228)	(4,072)	2,248	(6,422)
Income tax (benefit) expense	168	190	(545)	444
(Loss) income from continuing operations	(396)	(4,262)	2,793	(6,866)
Operating Segments
Segment Reporting Information [Line Items]
Total segment operating income	1,788	1,708	2,807	3,428
Extended Warranty | Operating Segments
Segment Reporting Information [Line Items]
Total segment operating income	1,035	1,090	1,602	1,936
Leased Real Estate | Operating Segments
Segment Reporting Information [Line Items]
Total segment operating income	$ 753	$ 618	$ 1,205	$ 1,492

XML

Related Parties - Insurance Income Strategies Ltd. (Details) - USD ($) $ in Millions	Jun. 30, 2019	Aug. 10, 2018
Equity Method Investee
Related Party Transaction [Line Items]
Percentage of assets		0.90%
Percentage of net profits		9.00%
Percentage of future fees		50.00%
Preferred stock issued		$ 15.0
IIS Re Ltd
Related Party Transaction [Line Items]
Ownership percentage by parent	100.00%

XML

Investment in Investee (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018	Dec. 31, 2018	Sep. 30, 2018
Schedule of Equity Method Investments [Line Items]
Carrying Value	$ 1,119		$ 1,119		$ 951
Equity in net loss of investees	$ 201	$ (385)	$ 168	$ (284)
Itasca Capital Ltd
Schedule of Equity Method Investments [Line Items]
Equity Percentage	22.90%	22.90%	22.90%	22.90%
Estimated Fair Value	$ 1,542	$ 951	$ 1,542	$ 951	1,000
Carrying Value	$ 1,119	$ 951	$ 1,119	$ 951		$ 2,700
Write-down of carrying value of investment					$ 1,700

XML

Investments - Net Investment Income (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Investment income:
Interest from fixed maturities	$ 122	$ 57	$ 195	$ 90
Dividends	70	82	128	156
Income from limited liability investments	32	189	14	181
Income from limited liability investments, at fair value	232	482	467	701
Income from real estate investments	200	200	400	400
Other	112	9	290	137
Gross investment income	768	1,019	1,494	1,665
Investment expenses	(19)	(9)	(46)	(17)
Net investment income	$ 749	$ 1,010	$ 1,448	$ 1,648

XML

Accumulated Other Comprehensive Income - AOCI Rollforward with Reclassification (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018	Jan. 01, 2018
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period	$ 26,603	$ 47,514	$ 24,258	$ 50,727
Balance at January 1, 2018, as adjusted					$ 50,073
Other comprehensive (loss) income	(591)	702	(1,431)	(104)
Balance, end of period	25,207	37,956	25,207	37,956
Total Accumulated Other Comprehensive Income
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period	39,922	35,844	40,768	(3,852)
Cumulative effect of adoption of ASU 2016-01					40,495
Balance at January 1, 2018, as adjusted					36,643
Other comprehensive income (loss) arising during the period	(635)	706	(1,475)	(86)
Amounts reclassified from accumulated other comprehensive income	38	(4)	32	(11)
Other comprehensive (loss) income	(597)	702	(1,443)	(97)
Balance, end of period	39,325	36,546	39,325	36,546
Unrealized Gains (Losses) on Available-for-Sale Investments
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period	(61)	(891)	(160)	(566)
Cumulative effect of adoption of ASU 2016-01					40
Balance at January 1, 2018, as adjusted					(526)
Other comprehensive income (loss) arising during the period	115	(72)	220	(430)
Amounts reclassified from accumulated other comprehensive income	(7)	(4)	(13)	(11)
Other comprehensive (loss) income	108	(76)	207	(441)
Balance, end of period	47	(967)	47	(967)
Foreign Currency Translation Adjustments
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period	(3,286)	(3,286)	(3,286)	(3,286)
Cumulative effect of adoption of ASU 2016-01					0
Balance at January 1, 2018, as adjusted					(3,286)
Other comprehensive income (loss) arising during the period	0	0	0	0
Amounts reclassified from accumulated other comprehensive income	0	0	0	0
Other comprehensive (loss) income	0	0	0	0
Balance, end of period	(3,286)	(3,286)	(3,286)	(3,286)
Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period	43,314	40,021	44,259	0
Cumulative effect of adoption of ASU 2016-01					40,455
Balance at January 1, 2018, as adjusted					$ 40,455
Other comprehensive income (loss) arising during the period	(750)	778	(1,695)	344
Amounts reclassified from accumulated other comprehensive income	0	0	0	0
Other comprehensive (loss) income	(750)	778	(1,695)	344
Balance, end of period	42,564	$ 40,799	42,564	$ 40,799
Equity in Other Comprehensive (Loss) Income of Limited Liability Investment
AOCI Including Portion Attributable to Noncontrolling Interest, Net of Tax [Roll Forward]
Balance, beginning of period	(45)		(45)
Other comprehensive income (loss) arising during the period	0		0
Amounts reclassified from accumulated other comprehensive income	45		45
Other comprehensive (loss) income	45		45
Balance, end of period	$ 0		$ 0

XML

Related Parties - Argo Management Group, LLC (Details) $ in Millions	12 Months Ended
	Dec. 31, 2018 USD ($)
Management
Related Party Transaction [Line Items]
Funding received	$ 0.5

XML

Accumulated Other Comprehensive Income

6 Months Ended

Jun. 30, 2019

Equity [Abstract]

ACCUMULATED OTHER COMPREHENSIVE INCOME

ACCUMULATED OTHER COMPREHENSIVE INCOME

The tables below detail the changes in the balances of each component of accumulated other comprehensive income, net of tax, for the three and six months ended June 30, 2019 and June 30, 2018 as relates to shareholders' equity attributable to common shareholders on the consolidated balance sheets. On the other hand, the unaudited consolidated statements of comprehensive (loss) income present the components of other comprehensive (loss) income, net of tax, only for the three and six months ended June 30, 2019 and June 30, 2018 and inclusive of the components attributable to noncontrolling interests in consolidated subsidiaries.

(in thousands)	Three months ended June 30, 2019
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk			Equity in Other Comprehensive (Loss) Income of Limited Liability Investment			Total Accumulated Other Comprehensive Income
Balance at April 1, 2019	$	(61	)	$	(3,286	)	$	43,314		$	(45	)	$	39,922
Other comprehensive income (loss) arising during the period	115			—			(750		)	—			(635		)
Amounts reclassified from accumulated other comprehensive income	(7		)	—			—			45			38
Net current-period other comprehensive income (loss)	108			—			(750		)	45			(597		)
Balance at June 30, 2019	$	47		$	(3,286	)	$	42,564		$	—		$	39,325

(in thousands)	Three months ended June 30, 2018
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk		Total Accumulated Other Comprehensive Income
Balance at April 1, 2018	$	(891	)	$	(3,286	)	$	40,021	$	35,844
Other comprehensive income (loss) arising during the period	(72		)	—			778		706
Amounts reclassified from accumulated other comprehensive income	(4		)	—			—		(4		)
Net current-period other comprehensive income (loss)	(76		)	—			778		702
Balance at June 30, 2018	$	(967	)	$	(3,286	)	$	40,799	$	36,546

(in thousands)	Six months ended June 30, 2019
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk			Equity in Other Comprehensive (Loss) Income of Limited Liability Investment			Total Accumulated Other Comprehensive Income
Balance at January 1, 2019	$	(160	)	$	(3,286	)	$	44,259		$	(45	)	$	40,768
Other comprehensive income (loss) arising during the period	220			—			(1,695		)	—			(1,475		)
Amounts reclassified from accumulated other comprehensive income	(13		)	—			—			45			32
Net current-period other comprehensive income (loss)	207			—			(1,695		)	45			(1,443		)
Balance at June 30, 2019	$	47		$	(3,286	)	$	42,564		$	—		$	39,325

(in thousands)	Six months ended June 30, 2018
	Unrealized Gains (Losses) on Available-for-Sale Investments			Foreign Currency Translation Adjustments			Change in Fair Value of Debt Attributable to Instrument-Specific Credit Risk		Total Accumulated Other Comprehensive Income
Balance at January 1, 2018	$	(566	)	$	(3,286	)	$	—	$	(3,852	)
Cumulative effect of adoption of ASU 2016-01	40			—			40,455		40,495
Balance at January 1, 2018, as adjusted	(526		)	(3,286		)	40,455		36,643
Other comprehensive loss arising during the period	(430		)	—			344		(86		)
Amounts reclassified from accumulated other comprehensive income	(11		)	—			—		(11		)
Net current-period other comprehensive loss	(441		)	—			344		(97		)
Balance at June 30, 2018	$	(967	)	$	(3,286	)	$	40,799	$	36,546

Components of accumulated other comprehensive income were reclassified to the following lines of the unaudited consolidated statements of operations for the three and six months ended June 30, 2019 and June 30, 2018:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Reclassification of accumulated other comprehensive income from unrealized gains (losses) on available-for-sale investments to:
Net realized (losses) gains	$	(38	)	$	5		$	(32	)	$	8
Other-than-temporary impairment loss	—			—			—			—
(Loss) income from continuing operations before income tax expense	(38		)	5			(32		)	8
Income tax expense	—			—			—			—
(Loss) income from continuing operations	(38		)	5			(32		)	8
Income from discontinued operations, net of taxes	—			(1		)	—			3
Net (loss) income	$	(38	)	$	4		$	(32	)	$	11

XML

Revenue from Contracts with Customers

6 Months Ended

Jun. 30, 2019

Revenue from Contract with Customer [Abstract]

REVENUE FROM CONTRACTS WITH CUSTOMERS

REVENUE FROM CONTRACTS WITH CUSTOMERS

Revenue from contracts with customers relates to Extended Warranty segment service fee and commission income. Service fee and commission income represents vehicle service agreement fees, GAP commissions, maintenance support service fees, warranty product commissions, homebuilder warranty service fees and homebuilder warranty commissions based on terms of various agreements with credit unions, consumers, businesses and homebuilders. Customers either pay in full at the inception of a warranty contract or commission product sale, or on terms subject to the Company’s customary credit reviews.

The following table disaggregates revenues from contracts with customers by revenue type:

(in thousands)	Three months ended June 30,				Six months ended June 30,
	2019		2018		2019		2018
Vehicle service agreement fees - IWS	$	4,551	$	4,226	$	9,030	$	8,615
GAP commissions - IWS	226		200		484		392
Maintenance support service fees - Trinity	1,732		1,962		3,700		4,935
Warranty product commissions - Trinity	817		736		1,399		1,232
Homebuilder warranty service fees - PWSC	1,475		1,548		2,898		2,975
Homebuilder warranty commissions - PWSC	198		188		409		362
Vehicle service agreement fees - Geminus	2,757		—		3,644		—
GAP commissions - Geminus	16		—		23		—
Service fee and commission income	$	11,772	$	8,860	$	21,587	$	18,511

IWS' vehicle service agreement fees include the fees collected to cover the costs of future automobile mechanical breakdown claims and the associated administration of those claims. Vehicle service agreement contract fees are earned over the duration of the vehicle service agreement contracts as the single performance obligation is satisfied.

IWS' GAP commissions include fees collected from the sale of GAP contracts. IWS acts as an agent on behalf of the third-party insurance company that underwrites and guaranties these GAP contracts. IWS does not assume any insurance risk from the sale of GAP contracts. IWS receives a single commission fee as its transaction price at the time it sells a GAP contract to a customer. Each GAP contract contains two separate performance obligations - sale of a GAP contract and GAP claims administration. The first performance obligation is related to the sale of a GAP contract and is satisfied upon closing the sale. The second performance obligation is related to the administration of claims during the GAP contract period, generally four years.

Standalone selling prices are not directly observable in the GAP contract for each of the separate performance obligations. As a result, IWS has applied the expected cost plus a margin approach to develop models to estimate the standalone selling price for each of its performance obligations in order to allocate the transaction price to the two separate performance obligations identified.

For the model related to the sale of a GAP contract performance obligation, IWS makes judgments about which of its actual costs are associated with selling activities. For the model related to the GAP claims administration performance obligation, IWS makes judgments about which of its actual costs are associated with claim-handling activities, which are performed over the life of the GAP contract period. The relative percentage of expected costs plus a margin associated with the sale of a GAP contract performance obligation is applied to the transaction price to determine the estimated standalone selling price of the sale of a GAP contract performance obligation, which IWS recognizes as earned at the time of the GAP contract sale. The relative percentage of expected costs plus a margin associated with the GAP claims administration performance obligation is applied to the transaction price to determine the estimated standalone selling price of the GAP claims administration performance obligation, which IWS recognizes as earned as services are performed over the GAP contract period.

For the GAP claims administration performance obligation, IWS applies an input method of measurement, based on the expected costs plus a margin of providing services, to determine the transfer of its services over the GAP contract period. IWS uses historical data regarding the number of claims it receives and activities performed, in addition to the number of GAP contracts sold, to estimate the number of claims to be received by year until coverage expires, which allows IWS to develop a revenue recognition pattern that it believes provides a faithful depiction of the transfer of services over time for the GAP claims administration performance obligation.

Trinity Warranty Solutions LLC's (Trinity") maintenance support service fees include the service fees collected to administer equipment breakdown and maintenance support services and are earned as services are rendered.

Trinity’s warranty product commissions include the commissions from the sale of warranty contracts for certain new and used heating, ventilation, air conditioning ("HVAC"), standby generator, commercial LED lighting and refrigeration equipment. Trinity acts as an agent on behalf of the third-party insurance companies that underwrite and guaranty these warranty contracts. Trinity does not guaranty the performance underlying the warranty contracts it sells. Warranty product commissions are earned at the time of the warranty product sales.

PWSC’s homebuilder warranty service fees include fees collected from the sale of warranties issued by new homebuilders. PWSC receives a single warranty service fee as its transaction price at the time it enters into a written contract with each of its builder customers. Each contract contains two separate performance obligations - warranty administrative services and other warranty services. Warranty administrative services include enrolling each home sold by the builder into the program and the warranty administrative system and delivering the warranty product. Other warranty services include answering builder or homeowner questions regarding the home warranty and dispute resolution services.

Standalone selling prices are not directly observable in the contract for each of the separate performance obligations. As a result, PWSC has applied the expected cost plus a margin approach to develop models to estimate the standalone selling price for each of its performance obligations in order to allocate the transaction price to the two separate performance obligations identified.

For the model related to the warranty administrative services performance obligation, PWSC makes judgments about which of its actual costs are associated with enrolling each home sold by the builder into the program and the warranty administrative system and delivering the warranty product. For the model related to the other warranty services performance obligation, PWSC makes judgments about which of its actual costs are associated with activities, such as answering builder or homeowner questions regarding the home warranty and dispute resolution services, which are performed over the life of the warranty coverage period. The relative percentage of expected costs plus a margin associated with the warranty administrative services performance obligation is applied to the transaction price to determine the estimated standalone selling price of the warranty administrative services performance obligation, which PWSC recognizes as earned at the time the home is enrolled and the warranty product is delivered. The relative percentage of expected costs plus a margin associated with the other warranty services performance obligation is applied to the transaction price to determine the estimated standalone selling price of the other warranty services performance obligation, which PWSC recognizes as earned as services are performed over the warranty coverage period.

For the other warranty services performance obligation, PWSC applies an input method of measurement, based on the expected costs plus a margin of providing services, to determine the transfer of its services over the warranty coverage period. PWSC uses historical data regarding the number of calls it receives and activities performed, in addition to the number of homes enrolled, to estimate the number of complaints and dispute resolution requests to be received by year until coverage expires, which allows PWSC to develop a revenue recognition pattern that it believes provides a faithful depiction of the transfer of services over time for the other warranty services performance obligation.

PWSC’s homebuilder warranty commissions include commissions from the sale of warranty contracts for those builders who have requested and receive insurance backing of their warranty obligations. PWSC acts as an agent on behalf of the third-party insurance company that underwrites and guaranties these warranty contracts. Homebuilder warranty commissions are earned on the certification date, which is typically the date of the closing of the sale of the home to the buyer. The Company also earns fees to manage remediation or repair services related to claims on insurance-backed warranty obligations, which are earned when the claims are closed, and a profit-sharing bonus on eligible warranties, which is determined based on expected ultimate loss ratio targets and is earned at the time the profit-sharing bonus is received.

Geminus' vehicle service agreement fees include the fees collected to cover the costs of future automobile mechanical breakdown claims and the associated administration of those claims. Vehicle service agreement contract fees are earned over the duration of the vehicle service agreement contracts as the single performance obligation is satisfied.

Receivables from contracts with customers are reported as service fee receivable, net in the consolidated balance sheets and at June 30, 2019 and December 31, 2018 were $5.2 million and $3.4 million, respectively.

The Company records deferred service fees resulting from contracts with customers when payment is received in advance of satisfying the performance obligations. The Company expects to recognize within one year as service fee and commission income approximately 40.5% of the deferred service fees as of June 30, 2019. Approximately $7.9 million of service fee and commission income recognized during the six months ended June 30, 2019 was included in deferred service fees as of December 31, 2018.

XML

Vehicle Service Agreement Liability

6 Months Ended

Jun. 30, 2019

Guarantees and Product Warranties [Abstract]

VEHICLE SERVICE AGREEMENT LIABILITY

VEHICLE SERVICE AGREEMENT LIABILITY

Vehicle service agreement fees include the fees collected to cover the costs of future automobile mechanical breakdown claims and the associated administration of those claims. Vehicle service agreement fees are initially recorded as deferred service fees. On a quarterly basis, the Company compares the remaining deferred service fees balance to the estimated amount of expected future claims under the vehicle service agreement contracts and records an additional accrual when the deferred service fees balance is less than expected future claims costs.

In certain jurisdictions the Company is required to refund to a customer a pro-rata share of the vehicle service agreement fees if a customer cancels the agreement prior to the end of the term. Depending on the jurisdiction, the Company may be entitled to deduct from the refund a cancellation fee and/or amounts for claims incurred prior to cancellation. While refunds vary depending on the term and type of product offered, historically refunds have averaged 9% to 13% of the original amount of the vehicle service agreement fee. Revenues recorded by the Company are net of refunds and the associated refund liability is included in deferred service fees.

A reconciliation of the changes in the vehicle service agreement liability, including deferred service fees related to vehicle service agreements, as of June 30, 2019 and June 30, 2018 were as follows:

(in thousands)	June 30, 2019			June 30, 2018
Balance at January 1, net	$	43,734		$	40,794
Vehicle service agreement liability acquired during the year related to the purchase of Geminus	10,792			—
Gross service fees for vehicle service agreements sold	14,549			11,166
Recognition of service fees on vehicle service agreements	(12,703		)	(9,588		)
Liability for claims authorized on vehicle service agreements	4,393			2,764
Payments of claims authorized on vehicle service agreements	(2,678		)	(2,950		)
Re-estimation of deferred service fees	(321		)	(165		)
Balance at June 30, net	$	57,766		$	42,021

The vehicle service agreement liability is presented as components of deferred services fees and accrued expenses and other liabilities in the consolidated balance sheets as follows:

(in thousands)	June 30,		December 31,
	2019		2018
Deferred service fees	$	57,182	$	43,495
Accrued expenses and other liabilities	584		239
Balance at end of period, net	$	57,766	$	43,734

XML

Investment in Investee

6 Months Ended

Jun. 30, 2019

Equity Method Investments and Joint Ventures [Abstract]

INVESTMENT IN INVESTEE

INVESTMENT IN INVESTEE

Investment in investee includes the Company's investment in the common stock of Itasca Capital Ltd. ("ICL"). The carrying value of the Company’s investment in investee is accounted for under the equity method, calculated using ICL’s reported financial statements. The carrying value, estimated fair value and approximate equity percentage for the Company's investment in investee at June 30, 2019 and December 31, 2018 were as follows:

(in thousands, except for percentages)
	June 30, 2019						December 31, 2018
	Equity Percentage		Estimated Fair Value		Carrying Value		Equity Percentage		Estimated Fair Value		Carrying Value
ICL	22.9	%	$	1,542	$	1,119	22.9	%	$	951	$	951

The estimated fair value of the Company's investment in ICL at June 30, 2019 in the table above is calculated based on the published closing price of ICL at June 30, 2019.

The carrying value of the Company's investment in investee at December 31, 2018, using ICL’s financial statements reported as of and for the period ended September 30, 2018, was calculated to be $2.7 million. The Company performed an analysis to determine whether its $2.7 million carrying value calculated under the equity method is recoverable. As part of its analysis, the Company considered that the estimated fair value of the Company's investment in investee at December 31, 2018, as presented in the table above and as calculated based on the published closing price of ICL common stock at December 31, 2018, was $1.0 million. The Company concluded that the $2.7 million carrying value of its investment in investee, as calculated under the equity method, had an other-than-temporary impairment as of December 31, 2018. As a result, the Company wrote down the carrying value of its investment in investee as of December 31, 2018, as presented in the table above, by $1.7 million such that its carrying value equaled the $1.0 million estimated fair value of the Company's investment in investee as calculated based on the published closing price of ICL common stock at December 31, 2018.

For the three months ended June 30, 2019 and June 30, 2018, equity in net income (loss) of investee was income of $0.2 million and loss of $0.4 million, respectively (income of $0.2 million and loss of $0.3 million for the six months ended June 30, 2019 and June 30, 2018, respectively). During the fourth quarter of 2019, the Company sold its remaining investment in the common stock of ICL. See Note 22(c), "Related Parties," for more information.

XML

Summary of Significant Accounting Policies

6 Months Ended

Jun. 30, 2019

Summary of significant accounting policies [Abstract]

SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES

Except as set forth below and as discussed in Note 4, "Recently Issued Accounting Standards," related to the Company's adoption of ASU 2016-02 effective January 1, 2019, there have been no material changes to our significant accounting policies as reported in our 2018 Annual Report.

Holding Company Liquidity

The Company's Extended Warranty subsidiaries fund their obligations primarily through service fee and commission income. The Company's Leased Real Estate subsidiary funds its obligations through rental income. The Company's insurance subsidiaries fund their obligations primarily through investment income and maturities in the investments portfolios.

The liquidity of the holding company is managed separately from its subsidiaries. The obligations of the holding company primarily consist of holding company operating expenses; transaction-related expenses; investments; and any other extraordinary demands on the holding company.

Actions available to the holding company to increase liquidity in order to meet its obligations include the sale of passive investments; sale of subsidiaries; issuance of debt or equity securities; distributions from the Company’s Extended Warranty subsidiaries, subject to certain restrictions; and giving notice to its Trust Preferred trustees of its intention to exercise its voluntary right to defer interest payments for up to 20 quarters on the six subsidiary trusts of the Company’s subordinated debt, which right the Company exercised during the third quarter of 2018.

Dividends from the Leased Real Estate segment are not generally considered a source of liquidity for the holding company, except upon the occurrence of certain events that would trigger payment of service fees. There can be no assurance as to the timing of the occurrence, or the resulting outcome, from one of these events.

The holding company’s liquidity, defined as the amount of cash in the bank accounts of Kingsway Financial Services Inc. and Kingsway America Inc., was $1.8 million and $1.9 million at June 30, 2019 and December 31, 2018, respectively, which excludes future actions available to the holding company that could be taken to increase liquidity and reflects approximately four months of operating cash. These amounts are reflected in the cash and cash equivalents of $10.9 million and $14.6 million reported at June 30, 2019 and December 31, 2018, respectively, on the Company’s consolidated balance sheets. The cash and cash equivalents and restricted cash other than the holding company’s liquidity represent restricted and unrestricted cash held by Kingsway Amigo Insurance Company ("Amigo"), Kingsway Reinsurance Corporation and the Company’s Extended Warranty and Leased Real Estate segments.

As of March 31, 2020, there are 182,876 shares of the Company’s Class A Preferred Stock (the "Preferred Shares"), issued and outstanding. Any outstanding Preferred Shares would be required to be redeemed by the Company on April 1, 2021 ("Redemption Date") at a redemption value of $6.7 million (assuming all current outstanding Preferred Shares would be redeemed), if the Company has sufficient legally available funds to do so. Additionally, the Company has exercised its right to defer payment of interest on its outstanding subordinated debt ("trust preferred securities") and, because of the deferral which totaled $10.5 million at March 31, 2020, the Company is prohibited from redeeming any shares of its capital stock while payment of interest on the trust preferred securities is being deferred. If, as of April 1, 2021, the Company was required to pay both the deferred interest on the trust preferred securities and redeem all the Preferred Shares currently outstanding, then the Company currently projects that it would not have sufficient legally available funds to do so. However, the Company would be prohibited from doing so under Delaware law and, as such, (a) the interest estimated to be $14.9 million on March 31, 2021 on the trust preferred securities would remain on deferral as permitted under the indentures and (b) in accordance with Delaware law the Preferred Shares would not be redeemed on the Redemption Date (with a redemption value of $6.7 million) and would instead remain outstanding and continue to accrue dividends until such time as the Company has sufficient legally available funds to redeem the Preferred Shares and is not otherwise prohibited from doing so. In such a situation, the Company would continue to operate in the ordinary course.

The Company notes there are several variables to consider in such a situation, and management is currently exploring the following opportunities: negotiating with the holders of the Preferred Shares with respect to the Redemption Date and/or other key provisions, raising additional funds through capital market transactions, as well as the Company’s continued strategy of working to monetize its non-core investments while attempting to maximize the tradeoff between liquidity and value received. The Company also notes that the conversion of any Preferred Shares that might occur prior to April 1, 2021 would impact its analysis as of April 1, 2021.

Based on the Company’s current business plan and revenue prospects, existing cash, cash equivalents, investment balances and anticipated cash flows from operations are expected to be sufficient to meet the Company’s working capital and operating expenditure requirements, excluding the cash that may be required to redeem the Preferred Shares and deferred interest on its trust preferred securities, for the next twelve months. However, the Company’s assessment could also be affected by various risks and uncertainties, including, but not limited to, the effects of the COVID-19 pandemic.

XML

Label	Element	Value
Noncontrolling Interest [Member]
Stockholders' Equity, Including Portion Attributable to Noncontrolling Interest, Adjusted Balance	us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAdjustedBalance1	$ 9,354,000
Common Stock [Member]
Stockholders' Equity, Including Portion Attributable to Noncontrolling Interest, Adjusted Balance	us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAdjustedBalance1	$ 0
Common Stock, Shares, Issued	us-gaap_CommonStockSharesIssued	21,708,190.00
Retained Earnings [Member]
Stockholders' Equity, Including Portion Attributable to Noncontrolling Interest, Adjusted Balance	us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAdjustedBalance1	$ (352,095,000)
Additional Paid-in Capital [Member]
Stockholders' Equity, Including Portion Attributable to Noncontrolling Interest, Adjusted Balance	us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAdjustedBalance1	356,171,000
Parent [Member]
Stockholders' Equity, Including Portion Attributable to Noncontrolling Interest, Adjusted Balance	us-gaap_StockholdersEquityIncludingPortionAttributableToNoncontrollingInterestAdjustedBalance1	40,719,000
Accounting Standards Update 2014-09 [Member] | Noncontrolling Interest [Member]
Cumulative Effect of New Accounting Principle in Period of Adoption	us-gaap_CumulativeEffectOfNewAccountingPrincipleInPeriodOfAdoption	(7,000)
Accounting Standards Update 2014-09 [Member] | Parent [Member]
Cumulative Effect of New Accounting Principle in Period of Adoption	us-gaap_CumulativeEffectOfNewAccountingPrincipleInPeriodOfAdoption	(647,000)
Accounting Standards Update 2016-01 [Member] | AOCI Attributable to Parent [Member]
Cumulative Effect of New Accounting Principle in Period of Adoption	us-gaap_CumulativeEffectOfNewAccountingPrincipleInPeriodOfAdoption	$ 40,495,000

XML

Related Parties

6 Months Ended

Jun. 30, 2019

Related Party Transactions [Abstract]

RELATED PARTIES

RELATED PARTIES

Related party transactions, including services provided to or received by the Company's subsidiaries, are measured in part by the amount of consideration paid or received as established and agreed by the parties. Except where disclosed elsewhere in these unaudited consolidated interim financial statements, the following is a summary of related party transactions.

(a)Argo Management Group, LLC

The Company acquired Argo Management Group, LLC ("Argo Management") in April 2016. Argo Management's primary business is to act as Managing Member of Argo Holdings. At June 30, 2019 and December 31, 2018, each of the Company, John T. Fitzgerald ("Fitzgerald"), the Company's Chief Executive Officer and President, and certain of Fitzgerald’s immediate family members owns equity interests in Argo Holdings, all of which interests were acquired prior to the Company’s acquisition of Argo Management. Subject to certain limitations, Argo Holdings' governing documents require all individuals and entities owning an equity interest in Argo Holdings to fund upon request his/her/its pro rata share of any funding requirements of Argo Holdings up to an aggregate maximum amount equal to his/her/its total capital commitment (each request for funds being referred to as a "Capital Call"). During 2018, the Company funded approximately $0.5 million in response to Capital Calls. During 2018, Fitzgerald and Fitzgerald’s immediate family members funded their respective Capital Calls. Argo Holdings used the proceeds of the Capital Calls to make investments, cover general operating expenses and pay the management fee owed to Argo Management. Argo Holdings made no Capital Calls during the six months ended June 30, 2019.

(b)1347 Property Insurance Holdings, Inc.

In November 2012, the Company formed Maison Insurance Company ("Maison"), a Louisiana domiciled property and casualty insurance company. In preparation for a transaction to take Maison public, the Company formed 1347 Property Insurance Holdings, Inc. (“PIH”). Maison was a wholly owned subsidiary of PIH, which completed an initial public offering effective March 31, 2014, pursuant to which the Company disposed of a majority interest in PIH. The Company owned zero and zero of the common shares of PIH at June 30, 2019 and December 31, 2018, respectively.

D. Kyle Cerminara ("Cerminara") was appointed to the PIH Board of Directors on December 27, 2016 and became Chairman of the Board of Directors of PIH on May 11, 2018. Since April 2012, Cerminara has also served as the Chief Executive Officer of Fundamental Global Investors, LLC ("FGI"). During 2018, FGI was a shareholder known by the Company to be a beneficial owner of more than 5% of the Company’s outstanding common shares. As of June 30, 2019, FGI is not known to be a shareholder or beneficial owner of more than 5% of the Company’s outstanding common shares. Larry G. Swets, Jr. ("Swets") has served as a member of the PIH Board of Directors since November 21, 2013 and served as the Chairman of the Board of Directors of PIH from March 5, 2017 to May 11, 2018. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018.

On February 11, 2014, the Company's subsidiary, 1347 Advisors, entered into a management services agreement with PIH which provides for certain services, including forecasting, analysis of capital structure and reinsurance programs, consultation in future restructuring or capital raising transactions, and consultation in corporate development initiatives, that 1347 Advisors will provide to PIH unless and until 1347 Advisors and PIH agree to terminate the services. On February 24, 2015, the Company announced that it had entered into a definitive agreement with PIH to terminate the management services agreement. Pursuant to the transaction, 1347 Advisors received the following consideration: $2.0 million in cash; $3.0 million of 8% preferred stock of PIH, mandatorily redeemable on February 24, 2020; a Performance Shares Grant Agreement with PIH, whereby 1347 Advisors will be entitled to receive 100,000 shares of PIH common stock if at any time the last sales price of PIH's common stock equals or exceeds $10.00 per share for any 20 trading days within any 30-trading day period; and warrants to purchase 1,500,000 shares of common stock of PIH with a strike price of $15.00, expiring on February 24, 2022.

On March 26, 2014, the Company entered into a Performance Share Grant Agreement with PIH, whereby the Company will be entitled to receive up to an aggregate of 375,000 shares of PIH common stock upon achievement of certain milestones for PIH’s stock price. Pursuant to the terms of the Performance Share Grant Agreement, if at any time the last sales price of PIH’s common stock equals or exceeds: (i) $12.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock; (ii) $15.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 125,000 shares of common stock earned pursuant to clause (i) herein); and (iii) $18.00 per share (as adjusted for stock splits, stock dividends, reorganizations, recapitalizations and the like) for any 20 trading days within any 30-trading day period, the Company will receive 125,000 shares of PIH common stock (in addition to the 250,000 shares of common stock earned pursuant to clauses (i) and (ii) herein).

On January 2, 2018, the Company entered into an agreement with PIH to cancel the $10.00 per share Performance Share Grant Agreement in exchange for cash consideration of $0.3 million and to sell the $3.0 million of 8% preferred stock of PIH, mandatorily redeemable on February 24, 2020, for $3.0 million plus accrued but unpaid dividends. On July 24, 2018, the Company entered into an agreement with PIH to cancel the $12.00 per share, $15.00 per share and $18.00 per share Performance Share Grant Agreement in exchange for cash consideration of $1.0 million. No shares were received by the Company under either of the performance share grant agreements as of June 30, 2019.

(c)Itasca Capital Ltd.

Investment in investee includes the Company's investment in the common stock of ICL, a publicly traded Canadian corporation, and is accounted for under the equity method. The Company owned 22.9% and 22.9% of the common shares of ICL at June 30, 2019 and December 31, 2018, respectively.

Ballantyne Strong Inc. ("Ballantyne") owned 40.6% and 40.6% of the common shares of ICL at June 30, 2019 and December 31, 2018, respectively. Cerminara has served as the Chief Executive Officer of Ballantyne since November 2015 and as Chairman of the Board of Ballantyne since May 2015. Cerminara was appointed to the ICL Board of Directors on June 13, 2016 and became Chairman of the Board of Directors of ICL on June 4, 2018. Since April 2012, Cerminara has also served as the Chief Executive Officer of FGI. During 2018, FGI was a shareholder known by the Company to be a beneficial owner of more than 5% of the Company’s outstanding common shares. As of June 30, 2019, FGI is not known to be a shareholder or beneficial owner of more than 5% of the Company’s outstanding common shares. Swets has served as the ICL Chief Executive Officer and a member of the ICL Board of Directors since June 9, 2016. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. Fitzgerald has served as a member of the ICL Board of Directors since June 9, 2016. Fitzgerald joined the Company as an Executive Vice President in April 2016 following the Company’s acquisition of Argo. Fitzgerald has served as the Company’s Chief Executive Officer since September 5, 2018 and has served on the Company’s Board of Directors since April 21, 2016.

ICL and the Company executed a management service agreement effective June 10, 2016 pursuant to which the Company provided management services to ICL, including the non-exclusive use and services of appropriately qualified individuals to serve as ICL’s Chief Executive Officer and Chief Financial Officer, for an annual service fee of $0.0 million. This agreement was later amended on November 17, 2017 to provide an annual service fee of $0.0 million, beginning with full year 2017. The agreement was ultimately terminated effective January 31, 2019.

On October 9, 2019, the Company executed an agreement to sell 1,974,113 shares of ICL common stock, at a price of C$0.35 per share, to FGI for cash proceeds totaling C$0.7 million. On October 31, 2019, the Company executed an agreement to sell 3,011,447 shares of ICL common stock, at a price of C$0.35 per share, to Swets for consideration totaling C$1.1 million, comprised of cash proceeds of C$0.2 million and 247,450 shares of the Company’s common stock. Both transactions closed during the fourth quarter of 2019. The 247,450 shares of the Company’s common stock were awarded to Swets pursuant to an Amended and Restated Restricted Stock Agreement (the "Swets Restricted Stock Agreement") executed on September 5, 2018 related to Swets’ departure from the Company. Pursuant to the Swets Restricted Stock Agreement, Swets retained 350,000 shares of restricted Company common stock that were to vest upon (i) the completion of the sale by 1347 Investors of its entire interest in the shares of Limbach common stock and (ii) the subsequent completion of the liquidation of 1347 Investors and the distribution of its assets to its members. Pursuant to a Distribution and Redemption Agreement, dated as of September 30, 2019, by and among 1347 Investors and its members, the Company received distributions of cash proceeds of $0.6 million, 594,750 shares of Limbach common stock and 400,000 warrants, exercisable at $15 and expiring July 20, 2023, on Limbach common shares, which the Company deemed as having satisfied the performance obligations described in the Swets Restricted Stock Agreement. Also, pursuant to the Swets Restricted Stock Agreement, Swets exercised his right to authorize the Company to withhold 102,550 shares of restricted Company common stock, which would otherwise have been delivered or available for vesting, in order to satisfy all federal, state, local or other taxes required to be withheld or paid in connection with such award, leaving Swets with 247,450 shares of the Company’s common stock.

(d)Fundamental Global Investors, LLC

During 2018, FGI was a shareholder known by the Company to be a beneficial owner of more than 5% of the Company’s outstanding common shares. As of June 30, 2019, FGI is not known to be a shareholder or beneficial owner of more than 5% of the Company’s outstanding common shares.

On October 25, 2017, the Company executed an agreement to sell 900,000 shares of PIH common stock, at a price of $7.85 per share, to FGI in two separate transactions for cash proceeds totaling $7.1 million. On November 1, 2017, the Company sold 475,428 of the 900,000 shares of PIH common stock to FGI for cash proceeds totaling $3.7 million. The second transaction, for the sale of the remaining 424,572 shares of PIH common stock for cash proceeds totaling $3.4 million, closed on March 15, 2018 following FGI having obtained the necessary regulatory approvals.

On July 30, 2018, the Company executed an agreement to sell its remaining 75,000 shares of PIH common stock, at a price of $7.13 per share, to FGI for cash proceeds totaling $0.5 million.

On July 30, 2018, the Company executed an agreement to sell 1,813,889 shares of ICL common stock, at a price of C$0.72 per share, to FGI for cash proceeds totaling C$1.3 million.

(e)Insurance Income Strategies Ltd.

IIS is a Bermuda corporation, formed in October 2017, organized to offer collateralized reinsurance in the property catastrophe market through its wholly owned operating subsidiary IIS Re Ltd. The Company held 100% of the outstanding common stock of IIS at June 30, 2019 and December 31, 2018. The Company did not invest any capital against the common shares and has not invested any capital in IIS via any other security of IIS. The Company also does not have any commitment to provide capital to IIS. See Note 7, "Variable Interest Entities," in the Company’s 2018 Annual Report for further discussion of IIS. Swets has served as the Chairman of the Board of Directors of IIS since its formation. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018.

Effective August 10, 2018, simultaneous with IIS issuing preferred stock to a third-party investor, the Company and IIS entered into a management service agreement, which describes the Company’s duties and rights to remuneration. The management service agreement describes the Company’s duties to include (a) identification and due diligence of potential transaction counterparties for consideration by IIS management; (b) advice on capital structure and corporate development opportunities; (c) support for compliance with the rules and regulations of the SEC; and (d) other periodic and special requests deemed within the scope of the management service agreement. The management service agreement provides for a fee 0.9% of the assets of IIS and 9% of the annual net profits.

Pursuant to other agreements executed August 10, 2018 simultaneous with IIS issuing preferred stock to a third-party investor, the Company (a) is obligated to share with the IIS third-party investor 50% of any future fees generated under the management service agreement and (b) waives its right to receive any fees until such time that the IIS third-party investor is either redeemed or exchanged into publicly traded equity shares of IIS, in either case for consideration not less than the IIS third-party investor’s original $15.0 million investment. As of December 31, 2018, neither of these scenarios had occurred, so the Company is not entitled to any fees under the management service agreement and has not recorded any such fees.

(f)Limited liability investments

The Company’s investments include investments in limited liability companies in which an officer or former officer of the Company is named as a Manager or is authorized to act on behalf of the Manager under the respective operating agreement.

Itasca Golf Investors, LLC:

Itasca Golf Investors, LLC ("IGI") was formed on April 8, 2014 for the general purpose of real estate investment. The members entered into an operating agreement under which the Company acquired a 42.9% membership interest in IGI. 1347 Capital LLC, a wholly owned subsidiary of the Company, was named the Manager of IGI in the operating agreement. Swets was authorized to act on behalf of the Manager. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. On September 5, 2018, the Company sold its investment in IGI to IGI Partners LLC for $1.5 million. Swets is a member of IGI Partners LLC.

AK Realty I LLC:

AK Realty I LLC ("AKR") was formed on September 21, 2015 for the purpose of becoming a member of AKA Opportunity Investments I LLC, a limited liability company formed for the purpose of investing, directly or indirectly, in real estate projects. The members of AKR entered into an operating agreement under which the Company acquired a 33.3% membership interest in AKR. Management of AKR is vested in a two-member Executive Committee. The Company designates one of the two members of the Executive Committee. Decisions of the Executive Committee require the unanimous approval of the members of the Executive Committee. The Company designated Swets as its representative on the Executive Committee. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018.

Logistics Leasing, LLC:

Logistics Leasing ("Logistics") was formed on July 26, 2017 for the purpose of acquiring and leasing small vehicles. The members of Logistics entered into an operating agreement under which the Company acquired a 50% membership interest in Logistics. The Company designates one of the two managers of Logistics. Major Decisions, as defined in the operating agreement, require the approval of members holding at least 51% of the membership interest. The Company designated Swets as a manager. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. During the first quarter of 2019, the Company impaired its investment in Logistics.

1347 Energy Holdings LLC:

1347 Energy Holdings LLC ("Energy") was formed on April 20, 2016 for the purpose of making investments in hydrocarbon assets as described in the operating agreement. At June 30, 2019 and December 31, 2018, the Company owned zero and 45.6% of the membership interests. The Company also held collateralized notes in principal amount of zero and $0.6 million at June 30, 2019 and December 31, 2018, respectively. Fitzgerald owned zero and 0.8% of the membership interests at June 30, 2019 and December 31, 2018, respectively. Energy was managed through a Board of Managers comprised of five managers, two of whom, Swets and Fitzgerald, were appointed by 1347 Capital LLC, a wholly owned subsidiary of the Company. With respect to any matter before the Board of Managers, the act of a majority of the managers constituting a quorum constituted the act of the Board. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. Fitzgerald joined the Company as an Executive Vice President in April 2016 following the Company’s acquisition of Argo. Fitzgerald has served as the Company’s Chief Executive Officer since September 5, 2018 and has served on the Company’s Board of Directors since April 21, 2016. During 2018, Energy entered into a purchase and sale agreement dated, February 12, 2018, for the sale of Energy to an unrelated third party, pursuant to which the Company’s $1.8 million collateralized loan to Energy and $0.7 million surety deposit were repaid in full and the Company’s equity investment, previously written down to zero under the equity method of accounting, was purchased. The transaction closed in a series of installments during the fourth quarter of 2018 and the first quarter of 2019.

1347 Investors LLC:

1347 Investors was formed on April 15, 2014 for the purpose of investing in and holding securities of 1347 Capital Corp., which subsequently merged with Limbach Holdings, Inc., a publicly traded company. The Company owned 26.7% of the membership units at June 30, 2019 and December 31, 2018. The Company's investment in 1347 Investors is accounted for at fair value and reported as limited liability investments, at fair value in the consolidated balance sheets, with any changes in fair value to be reported in gain (loss) on change in fair value of limited liability investment, at fair value in the consolidated statements of operations. The fair value of this investment is calculated based on a model that distributes the net equity of 1347 Investors to all classes of membership interests. The model uses quoted market prices and significant market observable inputs. The most significant input to the model is the observed stock price of Limbach common stock.

ICL owned 47.6% of the membership units at June 30, 2019 and December 31, 2018. Ballantyne owned 40.6% and 40.6% of the common shares of ICL at June 30, 2019 and December 31, 2018, respectively.

Swets and Cerminara are the named managers of 1347 Investors. All acts of the managers must be unanimous. Cerminara has served as the Chief Executive Officer of Ballantyne since November 2015 and as Chairman of the Board of Ballantyne since May 2015. Cerminara was appointed to the ICL Board of Directors on June 13, 2016 and became Chairman of the Board of Directors of ICL on June 4, 2018. Since April 2012, Cerminara has also served as the Chief Executive Officer of FGI. During 2018, FGI was a shareholder known by the Company to be a beneficial owner of more than 5% of the Company’s outstanding common shares.

As of June 30, 2019, FGI is not known to be a shareholder or beneficial owner of more than 5% of the Company’s outstanding common shares. Swets has served as the ICL Chief Executive Officer and a member of the ICL Board of Directors since June 9, 2016. Swets also served as the Company’s Chief Executive Officer from July 1, 2010 until September 5, 2018 and served on the Company’s Board of Directors from September 16, 2013 through December 21, 2018. Fitzgerald has served as a member of the ICL Board of Directors since June 9, 2016. Fitzgerald joined the Company as an Executive Vice President in April 2016 following the Company’s acquisition of Argo. Fitzgerald has served as the Company’s Chief Executive Officer since September 5, 2018 and has served on the Company’s Board of Directors since April 21, 2016.

Pursuant to a Distribution and Redemption Agreement, dated as of September 30, 2019, by and among 1347 Investors and its members, the Company received distributions on November 19, 2019 of cash proceeds of $0.6 million, 594,750 shares of Limbach common stock and 400,000 warrants, exercisable at $15 and expiring July 20, 2023, on Limbach common shares. As a result of this distribution, the Company no longer owns membership units in 1347 Investors.

(g)Atlas Financial Holdings, Inc.

In November 2010, the Company issued promissory notes (the "Notes") to five employees (each a "Debtor" and collectively the "Debtors") for a total of $1.1 million, each Note bearing an interest rate of 3% (not compounding). The Debtors used the proceeds to purchase shares of common stock in Atlas Financial Holdings, Inc. ("Atlas"). Atlas was created via a triangular merger and spun-off from the Company in December 2010, at which time the Debtors became employees of Atlas and were no longer employees of the Company. The Notes required annual payments of interest on the anniversary date of the Notes, with the principal and any unpaid interest due in full on or before January 1, 2017, in the case of one of the Debtors, and November 1, 2017, in the case of the other four Debtors. Each Debtor was required to pledge to the Company the shares purchased utilizing the Notes proceeds, and such pledge was to be released once the note was paid in full. The current market value of the pledged shares is $0.0 million.

The Notes have been amended three times since their issuance, generally to extend payments of principal while also requiring progress payments that were not part of the original Notes. No principal has been waived, and interest continues to accrue on unpaid principal. The remaining principal amount outstanding on the Notes was $0.7 million as of June 30, 2019. The Company has concluded there are no indications the Debtors were experiencing financial difficulties at the time of the amendments, and the Company expects to collect all amounts due. The Debtors are current with the amended terms of the Notes. As a result, the Company has concluded the Notes are not impaired.

(h)Other related party transactions

On July 16, 2018, the Company entered into a definitive agreement to sell Mendota to Premier Holdings LLC. Steve Harrison, President of Mendota, is a minority investor in Premier Holdings LLC.

On September 5, 2018, the Company entered into a Senior Advisor Agreement with Swets, its former Chief Executive Officer. The Senior Advisor Agreement was for a one-year term with an annual consulting fee of $0.3 million. After September 5, 2019, Swets will continue to provide certain consulting services for an hourly fee on an as-needed basis.

On February 28, 2020, the Company entered into a Consulting Agreement (the "Consulting Agreement") with William A. Hickey, Jr. ("Hickey"), its former Chief Financial Officer, pursuant to which Hickey will provide consulting and transition support through at least April 30, 2020, subject to renewal thereafter by agreement of the parties. In accordance with the Consulting Agreement, Hickey will receive a consulting fee of $0.1 million for the months of March and April 2020 and an hourly consulting fee of $165 for time worked in subsequent months.

XML

Acquisition and Discontinued Operations (Tables)

3 Months Ended

6 Months Ended

Mar. 31, 2019

Jun. 30, 2019

Business Combinations [Abstract]

Schedule of Estimated Fair Values of Assets Acquired and Liabilities Assumed

The following table summarizes the estimated fair values of the assets acquired and liabilities assumed at the date of acquisition:

(in thousands)
	March 1, 2019
Investments	$	4,405
Cash and cash equivalents	755
Restricted cash	2,650
Accrued investment income	32
Service fee receivable	513
Other receivables	12
Property and equipment, net	79
Goodwill	7,445
Intangible assets not subject to amortization - trade names	1,974
Intangible asset subject to amortization - customer relationships	3,732
Other assets	620
Total assets	$	22,217
Accrued expenses and other liabilities	$	2,018
Income taxes payable	1
Deferred service fees	10,564
Net deferred income tax liabilities	1,263
Total liabilities	$	13,846
Purchase price	$	8,371

Business Acquisition, Pro Forma Information

(in thousands, except per share data)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019		2018
Revenues	$	15,226		$	15,218		$	30,491	$	30,982
(Loss) income from continuing operations attributable to common shareholders	$	(906	)	$	(5,357	)	$	676	$	(8,874	)
Basic (loss) earnings per share - continuing operations	$	(0.04	)	$	(0.25	)	$	0.03	$	(0.41	)
Diluted (loss) earnings per share - continuing operations	$	(0.04	)	$	(0.25	)	$	0.03	$	(0.41	)

Summary of Discontinued Operations

Summary financial information for Mendota and ARS included in income from discontinued operations, net of taxes in the statements of operations for the three and six months ended June 30, 2018 is presented below:

(in thousands)	Three months ended June 30,			Six months ended June 30,
	2018			2018
Income (loss) from discontinued operations, net of taxes:
Revenues:
Net premiums earned	$	22,956		$	51,592
Total revenues	22,956			51,592
Other revenues (expenses), net:
Loss and loss adjustment expenses	(18,927		)	(41,728		)
Commissions and premium taxes	(2,225		)	(6,388		)
General and administrative expenses	(3,825		)	(7,778		)
Net investment income	208			434
Net realized losses	(134		)	(134		)
Gain on change in fair value of equity investments	96			106
Other income	2,445			4,876
Total other revenue (expenses), net	(22,362		)	(50,612		)
Income from discontinued operations before income tax benefit	594			980
Income tax benefit	—			—
Income from discontinued operations, net of taxes	594			980
Loss on disposal of discontinued operations before income tax expense	(6,628		)	(6,628		)
Income tax expense	—			—
Loss on disposal of discontinued operations, net of taxes	(6,628		)	(6,628		)
Total loss from discontinued operations, net of taxes	$	(6,034	)	$	(5,648	)

XML

Intangible Assets (Tables)

6 Months Ended

Jun. 30, 2019

Goodwill and Intangible Assets Disclosure [Abstract]

Schedule of Intangible Assets

Intangible assets at June 30, 2019 and December 31, 2018 are comprised as follows:

(in thousands)			June 30, 2019
	Gross Carrying Value			Accumulated Amortization		Net Carrying Value
Intangible assets subject to amortization:
Database	$	4,918		$	3,259	$	1,659
Vehicle service agreements in-force	3,680			3,675		5
Customer relationships	12,646			4,580		8,066
In-place lease	1,125			186		939
Non-compete	266			91		175
Intangible assets not subject to amortization:
Tenant relationship	73,667			—		73,667
Trade names	3,264			—		3,264
Total	$	99,566		$	11,791	$	87,775

(in thousands)			December 31, 2018
	Gross Carrying Value			Accumulated Amortization		Net Carrying Value
Intangible assets subject to amortization:
Database	$	4,918		$	3,013	$	1,905
Vehicle service agreements in-force	3,680			3,671		9
Customer relationships	8,914			3,691		5,223
In-place lease	1,125			155		970
Non-compete	266			64		202
Intangible assets not subject to amortization:
Tenant relationship	73,667			—		73,667
Trade names	1,290			—		1,290
Total	$	93,860		$	10,594	$	83,266

XML

Acquisition and Discontinued Operations - Income from Discontinued Operations (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended		12 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018	Dec. 31, 2018
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Loss and loss adjustment expenses	$ (601)	$ (1,301)	$ (708)	$ (1,647)
Net investment income	749	1,010	1,448	1,648
Gain on change in fair value of equity investments	(556)	132	(241)	397
(Loss) gain on change in fair value of equity investments	(63)	(421)	15	744
Income from discontinued operations, net of taxes	0	594	0	980
Loss on disposal of discontinued operations, net of taxes	$ 0	(6,628)	$ 0	(6,628)
Discontinued Operations
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Loss on disposal of discontinued operations, net of taxes					$ 1,300
Mendota and ARS | Discontinued Operations
Income Statement, Balance Sheet and Additional Disclosures by Disposal Groups, Including Discontinued Operations [Line Items]
Total revenues		22,956		51,592
Loss and loss adjustment expenses		(18,927)		(41,728)
Commissions and premium taxes		(2,225)		(6,388)
General and administrative expenses		(3,825)		(7,778)
Net investment income		208		434
Gain on change in fair value of equity investments		(134)		(134)
(Loss) gain on change in fair value of equity investments		96		106
Other income		2,445		4,876
Total other revenue (expenses), net		(22,362)		(50,612)
Income from discontinued operations before income tax benefit		594		980
Income tax benefit		0		0
Income from discontinued operations, net of taxes		594		980
Loss on disposal of discontinued operations before income tax expense		(6,628)		(6,628)
Income tax expense		0		0
Loss on disposal of discontinued operations, net of taxes		(6,628)		(6,628)
Total loss from discontinued operations, net of taxes		$ (6,034)		$ (5,648)

XML

Consolidated Statements of Comprehensive (Loss) Income - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Statement of Comprehensive Income [Abstract]
Net income (loss)	$ (396)	$ (10,296)	$ 2,793	$ (12,514)
Unrealized gains (losses) on available-for-sale investments:
Unrealized gains (losses) arising during the period	121	(72)	232	(437)
Reclassification adjustment for amounts included in net (loss) income	(7)	(4)	(13)	(11)
Change in fair value of debt attributable to instrument-specific credit risk	(750)	778	(1,695)	344
Equity in other comprehensive income of limited liability investment	45	0	45	0
Other comprehensive (loss) income	(591)	702	(1,431)	(104)
Comprehensive (loss) income	(987)	(9,594)	1,362	(12,618)
Less: comprehensive income attributable to noncontrolling interests in consolidated subsidiaries	264	158	481	511
Comprehensive (loss) income attributable to common shareholders	$ (1,251)	$ (9,752)	$ 881	$ (13,129)

XML

Document and Entity Information - shares	6 Months Ended
	Jun. 30, 2019	Apr. 10, 2020
Document Information [Abstract]
Document Quarterly Report	true
Document Transition Report	false
Entity Registrant Name	KINGSWAY FINANCIAL SERVICES INC.
Entity Central Index Key	0001072627
Current Fiscal Year End Date	--12-31
Entity Interactive Data Current	Yes
Entity Filer Category	Accelerated Filer
Entity Small Business	true
Entity Emerging Growth Company	false
Entity Shell Company	false
Document Type	10-Q
Document Period End Date	Jun. 30, 2019
Document Fiscal Year Focus	2019
Document Fiscal Period Focus	Q2
Amendment Flag	false
Entity Common Stock, Shares Outstanding		22,958,519

XML

Consolidated Statement of Cash Flows (Parenthetical) $ in Thousands	6 Months Ended
	Jun. 30, 2019 USD ($)
Statement of Cash Flows [Abstract]
Payments of debt issuance costs	$ 981

XML

Acquisition and Discontinued Operations - Narrative (Details) - USD ($) $ in Thousands			3 Months Ended		4 Months Ended	6 Months Ended
	Jun. 30, 2019	Mar. 01, 2019	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2019	Jun. 30, 2018	Dec. 31, 2018
Business Acquisition [Line Items]
Goodwill	$ 82,104		$ 82,104		$ 82,104	$ 82,104		$ 74,659
Geminus
Business Acquisition [Line Items]
Percentage of acquisition		100.00%
Purchase price		$ 8,371
Cash payments to acquire business		7,700
Liabilities incurred	$ 200	700
Goodwill		7,445
Intangible assets acquired		$ 5,700
Acquisition-related expenses			$ 0	$ 0		$ 0	$ 0
Revenue of acquiree since acquisition date					3,700
Earnings or loss of acquiree since acquisition date					$ 600

XML

Segmented Information (Tables)

6 Months Ended

Jun. 30, 2019

Segment Reporting [Abstract]

Reconciliation of Revenue from Segments to Consolidated

Revenues by reportable segment reconciled to consolidated revenues for the three and six months ended June 30, 2019 and June 30, 2018 were:

(in thousands)	Three months ended June 30,				Six months ended June 30,
	2019		2018		2019		2018
Revenues:
Extended Warranty:
Service fee and commission income	$	11,772	$	8,860	$	21,587	$	18,511
Other income	41		36		116		102
Total Extended Warranty	11,813		8,896		21,703		18,613
Leased Real Estate:
Rental income	3,341		3,341		6,682		6,682
Other income	72		72		142		219
Total Leased Real Estate	3,413		3,413		6,824		6,901
Total segment revenues	15,226		12,309		28,527		25,514
Rental income not allocated to segments	—		4		—		11
Total revenues	$	15,226	$	12,313	$	28,527	$	25,525

Reconciliation of Operating Profit (Loss) from Segments to Consolidated

egment operating income reconciled to the consolidated (loss) income from continuing operations for the three and six months ended June 30, 2019 and June 30, 2018 were:

(in thousands)	Three months ended June 30,						Six months ended June 30,
	2019			2018			2019			2018
Segment operating income:
Extended Warranty	$	1,035		$	1,090		$	1,602		$	1,936
Leased Real Estate	753			618			1,205			1,492
Total segment operating income	1,788			1,708			2,807			3,428
Net investment income	749			1,010			1,448			1,648
Net realized (losses) gains	(556		)	132			(241		)	397
(Loss) gain on change in fair value of equity investments	(63		)	(421		)	15			744
Gain (loss) on change in fair value of limited liability investments, at fair value	2,347			(525		)	6,612			(1,461		)
Net change in unrealized gain (loss) on private company investments	—			(155		)	19			(155		)
Other-than-temporary impairment loss	—			—			(75		)	—
Interest expense not allocated to segments	(2,339		)	(1,844		)	(4,441		)	(3,561		)
Other income and expenses not allocated to segments, net	(2,597		)	(3,213		)	(4,361		)	(5,625		)
Amortization of intangible assets	(676		)	(254		)	(1,197		)	(509		)
Gain (loss) on change in fair value of debt	918			(142		)	1,494			(1,061		)
Gain on disposal of subsidiary	—			17			—			17
Equity in net income (loss) of investee	201			(385		)	168			(284		)
(Loss) income from continuing operations before income tax expense (benefit)	(228		)	(4,072		)	2,248			(6,422		)
Income tax expense (benefit)	168			190			(545		)	444
(Loss) income from continuing operations	$	(396	)	$	(4,262	)	$	2,793		$	(6,866	)

XML

Revenue from Contracts with Customers - Disaggregated Revenue (Details) - USD ($) $ in Thousands	3 Months Ended		6 Months Ended
	Jun. 30, 2019	Jun. 30, 2018	Jun. 30, 2019	Jun. 30, 2018
Disaggregation of Revenue [Line Items]
Service fee and commission income	$ 11,772	$ 8,860	$ 21,587	$ 18,511
Extended Warranty | IWS | Vehicle service agreement fees
Disaggregation of Revenue [Line Items]
Service fee and commission income	4,551	4,226	9,030	8,615
Extended Warranty | IWS | GAP commissions
Disaggregation of Revenue [Line Items]
Service fee and commission income	226	200	484	392
Extended Warranty | Trinity | Maintenance support service fees
Disaggregation of Revenue [Line Items]
Service fee and commission income	1,732	1,962	3,700	4,935
Extended Warranty | Trinity | Warranty product commissions
Disaggregation of Revenue [Line Items]
Service fee and commission income	817	736	1,399	1,232
Extended Warranty | PWSC | Homebuilder warranty service fees
Disaggregation of Revenue [Line Items]
Service fee and commission income	1,475	1,548	2,898	2,975
Extended Warranty | PWSC | Homebuilder warranty commissions
Disaggregation of Revenue [Line Items]
Service fee and commission income	198	188	409	362
Extended Warranty | Geminus | Vehicle service agreement fees
Disaggregation of Revenue [Line Items]
Service fee and commission income	2,757	0	3,644	0
Extended Warranty | Geminus | GAP commissions
Disaggregation of Revenue [Line Items]
Service fee and commission income	$ 16	$ 0	$ 23	$ 0

XML

- 1347 Investors LLC (Details) - USD ($) $ / shares in Units, $ in Millions			6 Months Ended	12 Months Ended
	Nov. 19, 2019	Sep. 30, 2019	Jun. 30, 2019	Dec. 31, 2018	Jul. 26, 2017	Sep. 21, 2015
Limited Liability Company
Related Party Transaction [Line Items]
Equity method investment, ownership percentage			26.70%	26.70%
Equity Method Investee
Related Party Transaction [Line Items]
Equity method investment, ownership percentage			47.60%	47.60%	51.00%	33.30%
Board of Directors Chairman
Related Party Transaction [Line Items]
Equity method investment, ownership percentage			40.60%	40.60%
Subsequent Event
Related Party Transaction [Line Items]
Consideration received, cash	$ 0.6	$ 0.6
Consideration received (in shares)	594,750	594,750
Consideration received, warrants (in shares)	400,000	400,000
Warrant exercise price (in dollars per share)	$ 15	$ 15
Kingsway Financial Services, Inc | Fundamental Global Investors, LLC
Related Party Transaction [Line Items]
Ownership percentage (less than at June 30, 2019)			5.00%	5.00%

XML

Vehicle Service Agreement Liability - Components of Deferred Services Fees and Accrued Expenses (Details) - USD ($) $ in Thousands	Jun. 30, 2019	Dec. 31, 2018	Jun. 30, 2018	Dec. 31, 2017
Product Warranty Liability [Line Items]
Deferred service fees	$ 61,522	$ 47,130
Accrued expenses and other liabilities	16,518	14,786
Vehicle service agreement fees
Product Warranty Liability [Line Items]
Deferred service fees	57,182	43,495
Accrued expenses and other liabilities	584	239
Balance at end of period, net	$ 57,766	$ 43,734	$ 42,021	$ 40,794

XML

- Subordinated Borrowings (Details) - USD ($)	6 Months Ended
	Jun. 30, 2018	Jun. 30, 2019
Kingsway CT Statutory Trust I
Debt Instrument [Line Items]
Principal		$ 15,000,000
Kingsway CT Statutory Trust II
Debt Instrument [Line Items]
Principal		17,500,000
Kingsway CT Statutory Trust III
Debt Instrument [Line Items]
Principal		20,000,000
Kingsway DE Statutory Trust III
Debt Instrument [Line Items]
Principal		15,000,000
Kingsway DE Statutory Trust IV
Debt Instrument [Line Items]
Principal		10,000,000
Kingsway DE Statutory Trust VI
Debt Instrument [Line Items]
Principal		$ 13,000,000
LIBOR | Kingsway CT Statutory Trust I
Debt Instrument [Line Items]
Annual interest rate	4.00%
LIBOR | Kingsway CT Statutory Trust II
Debt Instrument [Line Items]
Annual interest rate	4.10%
LIBOR | Kingsway CT Statutory Trust III
Debt Instrument [Line Items]
Annual interest rate	3.95%
LIBOR | Kingsway DE Statutory Trust III
Debt Instrument [Line Items]
Annual interest rate	4.20%
LIBOR | Kingsway DE Statutory Trust IV
Debt Instrument [Line Items]
Annual interest rate	3.85%
LIBOR | Kingsway DE Statutory Trust VI
Debt Instrument [Line Items]
Annual interest rate	4.00%

XML

Income Taxes - Narrative (Details) - USD ($) $ in Thousands	3 Months Ended				6 Months Ended
	Jun. 30, 2019	Mar. 31, 2019	Jun. 30, 2018	Mar. 31, 2017	Jun. 30, 2019	Jun. 30, 2018	Dec. 31, 2018
Income Tax Disclosure [Abstract]
Federal tax rate				34.00%	21.00%
Deferred tax asset, increase (decrease), amount		$ 800
Net deferred income tax liabilities	$ 28,984				$ 28,984		$ 28,537
Deferred tax assets, operating loss carryforwards, subject to expiration	8,000				8,000		8,000
Goodwill and intangible assets	21,700				21,700
Deferred income tax assets, state taxes	600				600		500
Deferred tax liabilities, other	100				100		21,100
Regulatory assets and liabilities							100
Unrecognized tax benefits			$ 1,400			$ 1,400	1,400
Income tax expense recorded	100		$ 100		100	$ 100
Interest and penalties paid	$ 1,200				$ 1,200		$ 1,100