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Segmented Information (Tables)
6 Months Ended
Jun. 30, 2017
Segmented Information [Abstract]  
Segment Reporting Disclosure [Text Block]
SEGMENTED INFORMATION
The Company conducts its business through the following three reportable segments: Insurance Underwriting, Extended Warranty (formerly Insurance Services) and Leased Real Estate.
Insurance Underwriting Segment
Insurance Underwriting includes the following subsidiaries of the Company: Mendota, Mendakota, Mendakota Casualty Company ("MCC"), Kingsway Amigo Insurance Company ("Amigo") and Kingsway Reinsurance Corporation (collectively, "Insurance Underwriting"). Insurance Underwriting principally offers personal automobile insurance to drivers who do not meet the criteria for coverage by standard automobile insurers. Insurance Underwriting has policyholders in 12 states; however, new business is accepted in only eight states.
The Company previously placed Amigo and MCC into voluntary run-off in 2012 and 2011, respectively. Each of Amigo and MCC entered into a comprehensive run-off plan that was approved by its respective state of domicile. Kingsway continues to manage Amigo and MCC in a manner consistent with the run-off plans. During the first quarter of 2015, MCC sent a letter of intent to the Illinois Department of Insurance to resume writing private passenger automobile policies in the state of Illinois.  MCC began writing these policies on April 1, 2015.
Extended Warranty Segment
Extended Warranty includes the following subsidiaries of the Company: IWS Acquisition Corporation ("IWS") and Trinity Warranty Solutions LLC ("Trinity") (collectively, "Extended Warranty"). Prior to the second quarter of 2017, Extended Warranty was referred to as Insurance Services.

IWS is a licensed motor vehicle service agreement company and is a provider of after-market vehicle protection services distributed by credit unions in 24 states to their members.
Trinity is a provider of warranty products and maintenance support to consumers and businesses in the heating, ventilation, air conditioning, standby generator, commercial LED lighting and refrigeration industries. Trinity distributes its warranty products through original equipment manufacturers, HVAC distributors and commercial and residential contractors. Trinity distributes its maintenance support directly through corporate owners of retail spaces throughout the United States.
Leased Real Estate Segment
Leased Real Estate includes the Company's subsidiary, CMC, which was acquired on July 14, 2016. CMC owns the Real Property, which 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 (Loss) 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, 2017 and June 30, 2016 were:
(in thousands)
 
Three months ended June 30,
 
 
Six months ended June 30,
 
 
 
2017

 
2016

 
2017

 
2016

Revenues:
 
 
 
 
 
 
 
 
Insurance Underwriting:
 
 
 
 
 
 
 
 
Net premiums earned
 
$
33,518

 
$
31,813

 
$
66,440

 
$
61,240

Other income
 
2,560

 
2,665

 
5,033

 
4,938

Total Insurance Underwriting
 
36,078

 
34,478

 
71,473

 
66,178

Extended Warranty:
 
 
 
 
 
 
 
 
Service fee and commission income
 
6,873

 
5,394

 
13,435

 
10,716

Other income
 
51

 
62

 
136

 
116

Total Extended Warranty
 
6,924

 
5,456

 
13,571

 
10,832

Leased Real Estate:
 
 
 
 
 
 
 
 
Rental income
 
3,341

 

 
6,682

 

Other income
 
160

 

 
372

 

Total Leased Real Estate
 
3,501

 

 
7,054

 

Total segment revenues
 
46,503

 
39,934

 
92,098

 
77,010

Net premiums earned not allocated to segments
 

 

 

 

Net investment (loss) income
 
(2,366
)
 
1,072

 
(1,663
)
 
1,000

Net realized gains (losses)
 
734

 
67

 
1,132

 
(104
)
Other income not allocated to segments
 
44

 
64

 
89

 
111

Total revenues
 
$
44,915

 
$
41,137

 
$
91,656

 
$
78,017





The operating income (loss) by reportable segment in the following table is before income taxes and includes revenues and direct segment costs. Total segment operating income (loss) reconciled to the consolidated net loss for the three and six months ended June 30, 2017 and June 30, 2016 was:
(in thousands)
 
Three months ended June 30,
 
 
Six months ended June 30,
 
 
 
2017

 
2016

 
2017

 
2016

Segment operating income (loss):
 
 
 
 
 
 
 
 
Insurance Underwriting
 
$
(417
)
 
$
181

 
$
(1,159
)
 
$
(58
)
Extended Warranty
 
685

 
(780
)
 
1,271

 
(936
)
Leased Real Estate
 
872

 

 
1,790

 

Total segment operating income (loss)
 
1,140

 
(599
)
 
1,902

 
(994
)
Net investment (loss) income
 
(2,366
)
 
1,072

 
(1,663
)
 
1,000

Net realized gains (losses)
 
734

 
67

 
1,132

 
(104
)
Amortization of intangible assets
 
(289
)
 
(307
)
 
(580
)
 
(602
)
Contingent consideration benefit
 
212

 
657

 
212

 
657

Impairment of intangible assets
 

 

 
(250
)
 

Interest expense not allocated to segments
 
(1,216
)
 
(1,108
)
 
(2,375
)
 
(2,201
)
Other income and expenses not allocated to segments, net
 
(2,776
)
 
(1,940
)
 
(4,736
)
 
(3,841
)
Foreign exchange losses, net
 

 
(9
)
 
(4
)
 
(10
)
(Loss) gain on change in fair value of debt
 
(2,702
)
 
1,068

 
(4,591
)
 
3,596

Equity in net (loss) income of investee
 
(145
)
 
(874
)
 
2,240

 
(943
)
Loss from continuing operations before income tax expense
 
(7,408
)
 
(1,973
)
 
(8,713
)
 
(3,442
)
Income tax expense
 
1,251

 
26

 
1,430

 
52

Net loss from continuing operations
 
$
(8,659
)
 
$
(1,999
)
 
$
(10,143
)
 
$
(3,494
)

Insurance Underwriting net premiums earned by line of business for the three and six months ended June 30, 2017 and June 30, 2016 were:
(in thousands)
 
Three months ended June 30,
 
 
Six months ended June 30,
 
 
 
2017

 
2016

 
2017

 
2016

Insurance Underwriting:
 
 
 
 
 
 
 
 
Private passenger auto liability
 
$
22,933

 
$
21,656

 
$
45,309

 
$
41,731

Auto physical damage
 
10,585

 
10,157

 
21,131

 
19,509

Total net premiums earned
 
$
33,518

 
$
31,813

 
$
66,440

 
$
61,240

Reconciliation of Revenue from Segments to Consolidated [Table Text Block]
Revenues by reportable segment reconciled to consolidated revenues for the three and six months ended June 30, 2017 and June 30, 2016 were:
(in thousands)
 
Three months ended June 30,
 
 
Six months ended June 30,
 
 
 
2017

 
2016

 
2017

 
2016

Revenues:
 
 
 
 
 
 
 
 
Insurance Underwriting:
 
 
 
 
 
 
 
 
Net premiums earned
 
$
33,518

 
$
31,813

 
$
66,440

 
$
61,240

Other income
 
2,560

 
2,665

 
5,033

 
4,938

Total Insurance Underwriting
 
36,078

 
34,478

 
71,473

 
66,178

Extended Warranty:
 
 
 
 
 
 
 
 
Service fee and commission income
 
6,873

 
5,394

 
13,435

 
10,716

Other income
 
51

 
62

 
136

 
116

Total Extended Warranty
 
6,924

 
5,456

 
13,571

 
10,832

Leased Real Estate:
 
 
 
 
 
 
 
 
Rental income
 
3,341

 

 
6,682

 

Other income
 
160

 

 
372

 

Total Leased Real Estate
 
3,501

 

 
7,054

 

Total segment revenues
 
46,503

 
39,934

 
92,098

 
77,010

Net premiums earned not allocated to segments
 

 

 

 

Net investment (loss) income
 
(2,366
)
 
1,072

 
(1,663
)
 
1,000

Net realized gains (losses)
 
734

 
67

 
1,132

 
(104
)
Other income not allocated to segments
 
44

 
64

 
89

 
111

Total revenues
 
$
44,915

 
$
41,137

 
$
91,656

 
$
78,017

Reconciliation of Operating Profit (Loss) from Segments to Consolidated [Table Text Block]
egment operating income (loss) reconciled to the consolidated net loss for the three and six months ended June 30, 2017 and June 30, 2016 was:
(in thousands)
 
Three months ended June 30,
 
 
Six months ended June 30,
 
 
 
2017

 
2016

 
2017

 
2016

Segment operating income (loss):
 
 
 
 
 
 
 
 
Insurance Underwriting
 
$
(417
)
 
$
181

 
$
(1,159
)
 
$
(58
)
Extended Warranty
 
685

 
(780
)
 
1,271

 
(936
)
Leased Real Estate
 
872

 

 
1,790

 

Total segment operating income (loss)
 
1,140

 
(599
)
 
1,902

 
(994
)
Net investment (loss) income
 
(2,366
)
 
1,072

 
(1,663
)
 
1,000

Net realized gains (losses)
 
734

 
67

 
1,132

 
(104
)
Amortization of intangible assets
 
(289
)
 
(307
)
 
(580
)
 
(602
)
Contingent consideration benefit
 
212

 
657

 
212

 
657

Impairment of intangible assets
 

 

 
(250
)
 

Interest expense not allocated to segments
 
(1,216
)
 
(1,108
)
 
(2,375
)
 
(2,201
)
Other income and expenses not allocated to segments, net
 
(2,776
)
 
(1,940
)
 
(4,736
)
 
(3,841
)
Foreign exchange losses, net
 

 
(9
)
 
(4
)
 
(10
)
(Loss) gain on change in fair value of debt
 
(2,702
)
 
1,068

 
(4,591
)
 
3,596

Equity in net (loss) income of investee
 
(145
)
 
(874
)
 
2,240

 
(943
)
Loss from continuing operations before income tax expense
 
(7,408
)
 
(1,973
)
 
(8,713
)
 
(3,442
)
Income tax expense
 
1,251

 
26

 
1,430

 
52

Net loss from continuing operations
 
$
(8,659
)
 
$
(1,999
)
 
$
(10,143
)
 
$
(3,494
)
Revenue from External Customers by Geographic Areas [Table Text Block]
et premiums earned by line of business for the three and six months ended June 30, 2017 and June 30, 2016 were:
(in thousands)
 
Three months ended June 30,
 
 
Six months ended June 30,
 
 
 
2017

 
2016

 
2017

 
2016

Insurance Underwriting:
 
 
 
 
 
 
 
 
Private passenger auto liability
 
$
22,933

 
$
21,656

 
$
45,309

 
$
41,731

Auto physical damage
 
10,585

 
10,157

 
21,131

 
19,509

Total net premiums earned
 
$
33,518

 
$
31,813

 
$
66,440

 
$
61,240