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Investments (Tables)
 3 Months Ended
Mar. 31, 2019
Investments, Debt and Equity Securities [Abstract]  
Schedule of Investments by Operating Segment and/or Reporting Unit
The tables below present the components of revenue, expense, pre-tax income (loss), and assets for our reportable segment as well as Tiptree Capital for the following periods:
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
 
Three Months Ended 
 March 31, 2019
 
Three Months Ended 
 March 31, 2018
 
Specialty Insurance
 
Tiptree Capital
 
Total
 
Specialty Insurance
 
Tiptree Capital
 
Total
Total revenue
$
154,628

 
$
29,275

 
$
183,903

 
$
129,998

 
$
18,074

 
$
148,072

Total expense
(146,490
)
 
(23,357
)
 
(169,847
)
 
(128,655
)
 
(19,746
)
 
(148,401
)
Corporate expense
—

 
—

 
(8,901
)
 
—

 
—

 
(6,714
)
Net income (loss) before taxes from continuing operations
$
8,138

 
$
5,918

 
$
5,155

 
$
1,343

 
$
(1,672
)
 
$
(7,043
)
Less: provision (benefit) for income taxes
 
 
 
 
854

 
 
 
 
 
(1,568
)
Net income (loss) from discontinued operations
 
 
 
 
—

 
 
 
 
 
34,481

Net income (loss) before non-controlling interests
 
 
 
 
$
4,301

 
 
 
 
 
$
29,006

Less: net income (loss) attributable to non-controlling interests
 
 
 
 
376

 
 
 
 
 
5,446

Net income (loss) attributable to Common Stockholders
 
 
 
 
$
3,925

 
 
 
 
 
$
23,560

 
 
 
 
 
 

 
 
 
 
 
 

The following table summarizes sources of revenue from Tiptree Capital:
 
Three Months Ended 
 March 31,
 
2019
 
2018
Net realized and unrealized gains (losses) (1)
$
18,037

 
$
10,791

Other investment income (2)
9,881

 
5,108

Management fee income
1,267

 
1,577

Other
90

 
598

Total Revenue
$
29,275

 
$
18,074


(1) 
See Note (5) Investments for the components of Net realized and unrealized gains (losses) related to Tiptree Capital.
(2) 
See Note (5) Investments for the components of Other investment income.

The following table presents the reportable segment and Tiptree Capital assets for the following periods:
 
As of March 31, 2019
 
As of December 31, 2018
 
Specialty Insurance
 
Tiptree Capital
 
Corporate
 
Total
 
Specialty Insurance
 
Tiptree Capital
 
Corporate
 
Total
Total assets
$
1,450,765

 
$
320,320

 
$
43,755

 
$
1,814,840

 
$
1,514,084

 
$
318,420

 
$
32,414

 
$
1,864,918


The following table presents the Company's investments related to insurance operations (Specialty Insurance) and investments from other Tiptree investing activities (Tiptree Capital), measured at fair value as of the following periods:
 
As of March 31, 2019
 
As of December 31, 2018
 
Specialty Insurance
 
Tiptree Capital
 
Total
 
Specialty Insurance
 
Tiptree Capital
 
Total
Available for sale securities, at fair value
$
283,929

 
$
—

 
$
283,929

 
$
283,563

 
$
—

 
$
283,563

Loans, at fair value
71,633

 
53,512

 
125,145

 
158,466

 
56,917

 
215,383

Equity securities
26,977

 
95,615

 
122,592

 
29,425

 
93,554

 
122,979

Other investments
18,751

 
57,990

 
76,741

 
18,526

 
56,476

 
75,002

Total investments
$
401,290

 
$
207,117

 
$
608,407

 
$
489,980

 
$
206,947

 
$
696,927
Schedule of available-for-sale securities
Available for Sale Securities, at fair value

All of the Company’s investments in available for sale securities (AFS) as of March 31, 2019 and December 31, 2018 are held by subsidiaries in the specialty insurance business. The following tables present the Company's investments in available for sale securities:
 
As of March 31, 2019
 
Amortized cost
 
Gross
unrealized gains
 
Gross
unrealized losses
 
Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies
$
78,903

 
$
595

 
$
(213
)
 
$
79,285

Obligations of state and political subdivisions
63,234

 
745

 
(197
)
 
63,782

Corporate securities
93,144

 
798

 
(260
)
 
93,682

Asset backed securities
42,356

 
38

 
(1,203
)
 
41,191

Certificates of deposit
1,096

 
—

 
—

 
1,096

Obligations of foreign governments
4,865

 
29

 
(1
)
 
4,893

Total
$
283,598

 
$
2,205

 
$
(1,874
)
 
$
283,929

 
 
 
 
 
 
 
 
 
As of December 31, 2018
 
Amortized cost
 
Gross
unrealized gains
 
Gross
unrealized losses
 
Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies
$
71,945

 
$
266

 
$
(463
)
 
$
71,748

Obligations of state and political subdivisions
67,624

 
280

 
(458
)
 
67,446

Corporate securities
96,888

 
78

 
(1,241
)
 
95,725

Asset backed securities
41,912

 
14

 
(1,274
)
 
40,652

Certificates of deposit
1,241

 
—

 
—

 
1,241

Obligations of foreign governments
6,750

 
12

 
(11
)
 
6,751

Total
$
286,360

 
$
650

 
$
(3,447
)
 
$
283,563
Schedule of amortized cost and fair value by contractual maturity date
The amortized cost and fair values of investments in debt securities, by contractual maturity date, are shown below. Expected maturities may differ from contractual maturities because borrowers may have the right to call or prepay obligations with or without call or prepayment penalties.
 
As of
 
March 31, 2019
 
December 31, 2018
 
Amortized Cost
 
Fair Value
 
Amortized Cost
 
Fair Value
Due in one year or less
$
32,144

 
$
32,107

 
$
30,920

 
$
30,836

Due after one year through five years
166,245

 
167,544

 
167,201

 
166,366

Due after five years through ten years
30,208

 
30,291

 
32,805

 
32,185

Due after ten years
12,645

 
12,796

 
13,522

 
13,524

Asset-backed securities
42,356

 
41,191

 
41,912

 
40,652

Total
$
283,598

 
$
283,929

 
$
286,360

 
$
283,563
Schedule of available-for-sale securities, continuous unrealized loss position
The following tables summarize the gross unrealized losses on available for sale securities in an unrealized loss position:
 
As of March 31, 2019
 
Less Than or Equal to One Year
 
More Than One Year
 
Fair value
 
Gross
unrealized losses
 
# of Securities
 
Fair value
 
Gross unrealized losses
 
# of Securities
U.S. Treasury securities and obligations of U.S. government authorities and agencies
$
2,058

 
$
(3
)
 
15

 
$
21,591

 
$
(210
)
 
127

Obligations of state and political subdivisions
5,555

 
(3
)
 
13

 
15,093

 
(194
)
 
89

Corporate securities
4,292

 
(31
)
 
32

 
23,033

 
(229
)
 
271

Asset-backed securities
33,316

 
(272
)
 
12

 
2,665

 
(931
)
 
10

Obligations of foreign governments
—

 
—

 
—

 
942

 
(1
)
 
4

Total
$
45,221

 
$
(309
)
 
72

 
$
63,324

 
$
(1,565
)
 
501

 
 
 
 
 
 
 
 
 
 
 
 
 
As of December 31, 2018
 
Less Than or Equal to One Year
 
More Than One Year
 
Fair value
 
Gross
unrealized losses
 
# of Securities
 
Fair value
 
Gross unrealized losses
 
# of Securities
U.S. Treasury securities and obligations of U.S. government authorities and agencies
$
14,844

 
$
(70
)
 
51

 
$
19,495

 
$
(393
)
 
128

Obligations of state and political subdivisions
15,830

 
(30
)
 
41

 
21,594

 
(428
)
 
115

Corporate securities
47,976

 
(393
)
 
352

 
28,517

 
(848
)
 
404

Asset-backed securities
37,613

 
(1,262
)
 
35

 
614

 
(12
)
 
5

Obligations of foreign governments
2,313

 
(6
)
 
15

 
1,301

 
(5
)
 
8

Total
$
118,576

 
$
(1,761
)
 
494

 
$
71,521

 
$
(1,686
)
 
660
Restricted Investments
The following table presents the Company's restricted investments included in the Company's available for sale securities:
 
As of
 
March 31, 2019
 
December 31, 2018
Fair value of restricted investments for special deposits required by state insurance departments
$
6,317

 
$
9,398

Fair value of restricted investments in trust pursuant to reinsurance agreements
26,086

 
24,931

Total fair value of restricted investments
$
32,403

 
$
34,329
Available-for-sale Securities additional information
The following table presents additional information on the Company’s available for sale securities:
 
Three Months Ended 
 March 31,
 
2019
 
2018
Purchases of available for sale securities
$
29,861

 
$
75,570

 
 
 
 
Proceeds from maturities, calls and prepayments of available for sale securities
$
11,144

 
$
10,018

 
 
 
 
Gains (losses) realized on maturities, calls and prepayments of available for sale securities
$
—

 
$
(27
)
 
 
 
 
Gross proceeds from sales of available for sale securities
$
21,168

 
$
32,032

 
 
 
 
Gains (losses) realized on sales of available for sale securities
$
(5
)
 
$
(500
)