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Investments | 3 Months Ended
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Mar. 31, 2021
Investments, Debt and Equity Securities [Abstract] |
Investments | Investments The following table presents the Company's investments related to insurance operations (Insurance) and investments from other Tiptree investing activities (Tiptree Capital), measured at fair value as of the following periods:
| As of March 31, 2021 |  |
|  |  | Tiptree Capital |  |  |  |  |  |  |  |
| Insurance |  | Mortgage |  | Other |  | Total |  |  |  |  |  |
Available for sale securities, at fair value, net of allowance for credit losses | $ | 409,947 |  |  | $ | — |  |  | $ | — |  |  | $ | 409,947 |  |  |  |  |  |  |
Loans, at fair value | 10,832 |  |  | 99,626 |  |  | — |  |  | 110,458 |  |  |  |  |  |  |
Equity securities | 105,548 |  |  | — |  |  | 39,474 |  |  | 145,022 |  |  |  |  |  |  |
Other investments | 122,417 |  |  | 12,021 |  |  | 84,033 |  |  | 218,471 |  |  |  |  |  |  |
Total investments | $ | 648,744 |  |  | $ | 111,647 |  |  | $ | 123,507 |  |  | $ | 883,898 |  |  |  |  |  |  |
| As of December 31, 2020
|  |  | Tiptree Capital |  |
| Insurance |  | Mortgage |  | Other |  | Total
Available for sale securities, at fair value, net of allowance for credit losses | $ | 377,133 |  |  | $ | — |  |  | $ | — |  |  | $ | 377,133 |
Loans, at fair value | 7,795 |  |  | 82,937 |  |  | — |  |  | 90,732 |
Equity securities | 98,130 |  |  | — |  |  | 25,708 |  |  | 123,838 |
Other investments | 125,833 |  |  | 9,439 |  |  | 84,429 |  |  | 219,701 |
Total investments | $ | 608,891 |  |  | $ | 92,376 |  |  | $ | 110,137 |  |  | $ | 811,404 |
Available for Sale Securities, at fair value, net of allowance for credit losses All of the Company’s investments in Available for Sale Securities, at fair value, net of allowance for credit losses (AFS securities) as of March 31, 2021 and December 31, 2020 are held by subsidiaries in the insurance business. The following tables present the Company's investments in AFS securities:
| As of March 31, 2021
| Amortized cost |  | Allowance for Credit Losses(1) |  | Gross unrealized gains |  | Gross unrealized losses |  | Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies | $ | 206,825 |  |  | $ | — |  |  | $ | 3,964 |  |  | $ | (1,054) |  |  | $ | 209,735 |
Obligations of state and political subdivisions | 45,924 |  |  | — |  |  | 1,483 |  |  | (113) |  |  | 47,294 |
Corporate securities | 107,785 |  |  | (101) |  |  | 1,424 |  |  | (575) |  |  | 108,533 |
Asset backed securities | 40,233 |  |  | — |  |  | 206 |  |  | (1,917) |  |  | 38,522 |
Certificates of deposit | 1,356 |  |  | — |  |  | — |  |  | — |  |  | 1,356 |
Obligations of foreign governments | 4,546 |  |  | (5) |  |  | 20 |  |  | (54) |  |  | 4,507 |
Total | $ | 406,669 |  |  | $ | (106) |  |  | $ | 7,097 |  |  | $ | (3,713) |  |  | $ | 409,947 |
| As of December 31, 2020
| Amortized cost |  | Allowance for Credit Losses(1) |  | Gross unrealized gains |  | Gross unrealized losses |  | Fair value
U.S. Treasury securities and obligations of U.S. government authorities and agencies | $ | 191,116 |  |  | $ | — |  |  | $ | 5,245 |  |  | $ | (58) |  |  | $ | 196,303 |
Obligations of state and political subdivisions | 42,583 |  |  | — |  |  | 1,768 |  |  | (1) |  |  | 44,350 |
Corporate securities | 92,761 |  |  | — |  |  | 2,181 |  |  | (1) |  |  | 94,941 |
Asset backed securities | 37,975 |  |  | — |  |  | 316 |  |  | (2,099) |  |  | 36,192 |
Certificates of deposit | 1,355 |  |  | — |  |  | — |  |  | — |  |  | 1,355 |
Obligations of foreign governments | 3,961 |  |  | — |  |  | 31 |  |  | — |  |  | 3,992 |
Total | $ | 369,751 |  |  | $ | — |  |  | $ | 9,541 |  |  | $ | (2,159) |  |  | $ | 377,133 |
(1) - Represents the amount of impairment that has resulted from credit-related factors, and therefore was recognized in net realized and unrealized gains (losses) as a credit loss on AFS securities. Amount excludes unrealized losses relating to non-credit factors.
The amortized cost and fair values of AFS 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, 2021 |  | December 31, 2020
| Amortized Cost |  | Fair Value |  | Amortized Cost |  | Fair Value
Due in one year or less | $ | 36,505 |  |  | $ | 36,902 |  |  | $ | 30,306 |  |  | $ | 30,602 |
Due after one year through five years | 167,610 |  |  | 169,987 |  |  | 149,378 |  |  | 153,406 |
Due after five years through ten years | 38,340 |  |  | 38,292 |  |  | 26,621 |  |  | 27,479 |
Due after ten years | 123,981 |  |  | 126,244 |  |  | 125,471 |  |  | 129,454 |
Asset backed securities | 40,233 |  |  | 38,522 |  |  | 37,975 |  |  | 36,192 |
Total | $ | 406,669 |  |  | $ | 409,947 |  |  | $ | 369,751 |  |  | $ | 377,133 |
The following tables present the gross unrealized losses on AFS securities by length of time that individual AFS securities have been in a continuous unrealized loss position for less than twelve months, and twelve months or greater and do not have an allowance for credit losses:
| As of March 31, 2021
| 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 | $ | 74,713 |  |  | $ | (1,054) |  |  | 172 |  |  | $ | 1 |  |  | $ | — |  |  | 2 |
Obligations of state and political subdivisions | 9,082 |  |  | (113) |  |  | 42 |  |  | — |  |  | — |  |  | — |
Corporate securities | 44,717 |  |  | (575) |  |  | 178 |  |  | — |  |  | — |  |  | — |
Asset backed securities | 4,517 |  |  | (20) |  |  | 20 |  |  | 3,531 |  |  | (1,897) |  |  | 4 |
Obligations of foreign governments | 1,868 |  |  | (54) |  |  | 6 |  |  | — |  |  | — |  |  | — |
Total | $ | 134,897 |  |  | $ | (1,816) |  |  | 418 |  |  | $ | 3,532 |  |  | $ | (1,897) |  |  | 6 |
| As of December 31, 2020
| 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 | $ | 15,323 |  |  | $ | (58) |  |  | 41 |  |  | $ | 2 |  |  | $ | — |  |  | 2 |
Obligations of state and political subdivisions | 379 |  |  | (1) |  |  | 5 |  |  | — |  |  | — |  |  | — |
Corporate securities | 901 |  |  | (1) |  |  | 3 |  |  | — |  |  | — |  |  | — |
Asset backed securities | — |  |  | — |  |  | — |  |  | 18,927 |  |  | (2,099) |  |  | 9 |
Total | $ | 16,603 |  |  | $ | (60) |  |  | 49 |  |  | $ | 18,929 |  |  | $ | (2,099) |  |  | 11 |
Management believes that it is more likely than not that the Company will be able to hold the fixed maturity AFS securities that were in an unrealized loss position as of March 31, 2021 until full recovery of their amortized cost basis. The table below presents a roll-forward of the activity in the allowance for credit losses on AFS securities by type as of March 31, 2021:
|  |  | Obligations of state and political subdivisions |  | Corporate securities |  | Asset backed securities |  | Obligations of foreign governments |  | Total
Balance as of December 31, 2019 |  |  | $ | — |  |  | $ | — |  |  | $ | — |  |  | $ | — |  |  | $ | — |
Increase in the allowance for the initial adoption of ASU 2016-13 |  |  | (1) |  |  | (50) |  |  | (2) |  |  | — |  |  | (53) |
Gains from recoveries of amounts previously written off |  |  | 1 |  |  | 31 |  |  | 2 |  |  | — |  |  | 34 |
Balance as of March 31, 2020 |  |  | $ | — |  |  | $ | (19) |  |  | $ | — |  |  | $ | — |  |  | $ | (19) |
Balance as of December 31, 2020 |  |  | $ | — |  |  | $ | — |  |  | $ | — |  |  | $ | — |  |  | $ | — |
(Increase) in allowance for credit losses |  |  | — |  |  | (101) |  |  | — |  |  | (5) |  |  | (106) |
Balance as of March 31, 2021 |  |  | $ | — |  |  | $ | (101) |  |  | $ | — |  |  | $ | (5) |  |  | $ | (106) |
The Company applies a discounted cash flow model, based on assumptions and model outputs provided by an investment management company, in determining its lifetime expected credit losses on AFS securities. This includes determining the present value of expected future cash flows discounted at the book yield of the security. The table below presents the amount of credit losses (gains from recoveries) on AFS securities recorded by the Company for the following period:
| Three Months Ended March 31,
| 2021 |  | 2020
Credit losses (gains from recoveries) on AFS securities | $ | 106 |  |  | $ | (34) |
Pursuant to certain reinsurance agreements and statutory licensing requirements, the Company has deposited invested assets in custody accounts or insurance department safekeeping accounts. The Company cannot remove or replace investments in regulatory deposit accounts without prior approval of the contractual party or regulatory authority, as applicable. The following table presents the Company's restricted investments included in the Company's AFS securities:
| As of
| March 31, 2021 |  | December 31, 2020
Fair value of restricted investments in trust pursuant to reinsurance agreements | $ | 44,268 |  |  | $ | 44,349 |
Fair value of restricted investments for special deposits required by state insurance departments | 9,341 |  |  | 9,447 |
Total fair value of restricted investments | $ | 53,609 |  |  | $ | 53,796 |
The following table presents additional information on the Company’s AFS securities:
| Three Months Ended March 31, |  |
| 2021 |  | 2020 |  |  |  |  |  |
Purchases of AFS securities | $ | 68,702 |  |  | $ | 23,580 |  |  |  |  |  |  |
Proceeds from maturities, calls and prepayments of AFS securities | $ | 17,740 |  |  | $ | 19,660 |  |  |  |  |  |  |
Gross proceeds from sales of AFS securities | $ | 13,645 |  |  | $ | 5,560 |  |  |  |  |  |  |
The following table presents the gross realized gains and gross realized losses from sales and redemptions of AFS securities:
| Three Months Ended March 31, |  |
| 2021 |  | 2020 |  |  |  |  |  |
Gross realized gains | $ | 128 |  |  | $ | 67 |  |  |  |  |  |  |
Gross realized (losses) | — |  |  | (63) |  |  |  |  |  |  |
Total net realized gains (losses) from investment sales and redemptions | $ | 128 |  |  | $ | 4 |  |  |  |  |  |  |
Loans, at fair value The following table presents the Company’s investments in loans measured at fair value and the Company’s investments in loans measured at fair value pledged as collateral:
| As of March 31, 2021 |  | As of December 31, 2020
| Fair value |  | Unpaid principal balance (UPB) |  | Fair value exceeds / (below) UPB |  | Pledged as Collateral |  | Fair value |  | Unpaid principal balance (UPB) |  | Fair value exceeds / (below) UPB |  | Pledged as Collateral
Insurance: |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
Corporate loans (1) | $ | 10,832 |  |  | $ | 14,941 |  |  | $ | (4,109) |  |  | $ | — |  |  | $ | 7,795 |  |  | $ | 12,281 |  |  | $ | (4,486) |  |  | $ | — |
Mortgage: |  |  |  |  |  |  |  |  |  |  |  |  |  |  |
Mortgage loans held for sale (2) | 99,626 |  |  | 97,043 |  |  | 2,583 |  |  | 97,499 |  |  | 82,937 |  |  | 78,590 |  |  | 4,347 |  |  | 81,630 |
Total loans, at fair value | $ | 110,458 |  |  | $ | 111,984 |  |  | $ | (1,526) |  |  | $ | 97,499 |  |  | $ | 90,732 |  |  | $ | 90,871 |  |  | $ | (139) |  |  | $ | 81,630 |
(1) The cost basis of Corporate loans was approximately $13,463 and $11,282 at March 31, 2021 and December 31, 2020, respectively. (2) As of March 31, 2021 and December 31, 2020, there were two mortgage loans held for sale that were 90 days or more past due, respectively, with a fair value of $334 and $534, respectively. Equity Securities Equity securities consist mainly of publicly traded common and preferred stocks. Included within the equity securities balance are 17.0 million shares of Invesque as of March 31, 2021 and December 31, 2020, for which the Company has elected to apply the fair value option. The following table presents information on the cost and fair value of the Company’s equity securities related to insurance operations and other Tiptree investing activity as of the following periods:
| As of March 31, 2021 |  |
| Insurance |  | Tiptree Capital - Other |  | Total |  |  |  |  |  |
| Cost |  | Fair Value |  | Cost |  | Fair Value |  | Cost |  | Fair Value |  |  |  |  |  |
Invesque | $ | 23,339 |  |  | $ | 8,245 |  |  | $ | 111,491 |  |  | $ | 39,474 |  |  | $ | 134,830 |  |  | $ | 47,719 |  |  |  |  |  |  |
Fixed income exchange traded fund | 62,438 |  |  | 64,293 |  |  | — |  |  | — |  |  | 62,438 |  |  | 64,293 |  |  |  |  |  |  |
Other equity securities | 36,337 |  |  | 33,010 |  |  | — |  |  | — |  |  | 36,337 |  |  | 33,010 |  |  |  |  |  |  |
Total equity securities | $ | 122,114 |  |  | $ | 105,548 |  |  | $ | 111,491 |  |  | $ | 39,474 |  |  | $ | 233,605 |  |  | $ | 145,022 |  |  |  |  |  |  |
| As of December 31, 2020
| Insurance |  | Tiptree Capital - Other |  | Total
| Cost |  | Fair Value |  | Cost |  | Fair Value |  | Cost |  | Fair Value
Invesque | $ | 23,339 |  |  | $ | 5,370 |  |  | $ | 111,491 |  |  | $ | 25,708 |  |  | $ | 134,830 |  |  | $ | 31,078 |
Fixed income exchange traded fund | 62,438 |  |  | 63,875 |  |  | — |  |  | — |  |  | 62,438 |  |  | 63,875 |
Other equity securities | 38,069 |  |  | 28,885 |  |  | — |  |  | — |  |  | 38,069 |  |  | 28,885 |
Total equity securities | $ | 123,846 |  |  | $ | 98,130 |  |  | $ | 111,491 |  |  | $ | 25,708 |  |  | $ | 235,337 |  |  | $ | 123,838 |
Other Investments The following table contains information regarding the Company’s other investments as of the following periods:
| As of March 31, 2021
|  |  | Tiptree Capital |  |
| Insurance |  | Mortgage |  | Other |  | Total
Corporate bonds, at fair value (1) | $ | 101,296 |  |  | $ | — |  |  | $ | — |  |  | $ | 101,296 |
Vessels, net (2) | — |  |  | — |  |  | 82,657 |  |  | 82,657 |
Debentures | 20,377 |  |  | — |  |  | — |  |  | 20,377 |
Other | 744 |  |  | 12,021 |  |  | 1,376 |  |  | 14,141 |
Total other investments | $ | 122,417 |  |  | $ | 12,021 |  |  | $ | 84,033 |  |  | $ | 218,471 |
| As of December 31, 2020
|  |  | Tiptree Capital |  |
| Insurance |  | Mortgage |  | Other |  | Total
Corporate bonds, at fair value (1) | $ | 105,777 |  |  | $ | — |  |  | $ | — |  |  | $ | 105,777 |
Vessels, net (2) | — |  |  | — |  |  | 83,028 |  |  | 83,028 |
Debentures | 17,703 |  |  | — |  |  | — |  |  | 17,703 |
Other | 2,353 |  |  | 9,439 |  |  | 1,401 |  |  | 13,193 |
Total other investments | $ | 125,833 |  |  | $ | 9,439 |  |  | $ | 84,429 |  |  | $ | 219,701 |
(1) The cost basis of corporate bonds was $95,644 and $97,284 as of March 31, 2021 and December 31, 2020, respectively. (2) Net of accumulated depreciation of $9,515 and $8,372 as of March 31, 2021 and December 31, 2020, respectively. Net Investment Income - Insurance Net investment income represents investment income and expense from investments related to insurance operations as disclosed within net investment income on the condensed consolidated statements of operations. The following table presents the components of net investment income by source of income:
| Three Months Ended March 31, |  |
| 2021 |  | 2020 |  |  |  |  |  |
Interest: |  |  |  |  |  |  |  |  |
AFS securities | $ | 1,724 |  |  | $ | 2,281 |  |  |  |  |  |  |
Loans, at fair value | 205 |  |  | 173 |  |  |  |  |  |  |
Other investments | 1,282 |  |  | 855 |  |  |  |  |  |  |
Dividends from equity securities | 89 |  |  | 591 |  |  |  |  |  |  |
Other | 20 |  |  | — |  |  |  |  |  |  |
Subtotal | 3,320 |  |  | 3,900 |  |  |  |  |  |  |
Less: investment expenses | 553 |  |  | 412 |  |  |  |  |  |  |
Net investment income | $ | 2,767 |  |  | $ | 3,488 |  |  |  |  |  |  |
Other Investment Income - Tiptree Capital Other investment income represents other revenue from other Tiptree non-insurance activities as disclosed within other revenue on the condensed consolidated statements of operations, see Note (16) Other Revenue and Other Expenses. The following tables present the components of other investment income by type:
| Three Months Ended March 31, |  |
| 2021 |  | 2020 |  |  |  |  |  |
Interest: |  |  |  |  |  |  |  |  |
Loans, at fair value (1) | $ | 1,672 |  |  | $ | 1,731 |  |  |  |  |  |  |
Dividends from equity securities | — |  |  | 2,533 |  |  |  |  |  |  |
Loan fee income | 5,362 |  |  | 3,554 |  |  |  |  |  |  |
Vessel related revenue | 5,699 |  |  | 7,246 |  |  |  |  |  |  |
Other investment income | $ | 12,733 |  |  | $ | 15,064 |  |  |  |  |  |  |
(1) Primarily relates to Loans, at fair value classified as Held for Sale. See Note (4) Assets and Liabilities Held for Sale. Net Realized and Unrealized Gains (Losses) The following table presents the components of net realized and unrealized gains (losses) recorded on the condensed consolidated statements of operations. Net unrealized gains (losses) on AFS securities are included within other comprehensive income (loss) (OCI), net of tax, and, as such, are not included in this table. Net realized and unrealized gains (losses) on non-investment related financial assets and liabilities are included below:
| Three Months Ended March 31, |  |
| 2021 |  | 2020 |  |  |  |  |  |
Net realized gains (losses) |  |  |  |  |  |  |  |  |
Insurance: |  |  |  |  |  |  |  |  |
Reclass of unrealized gains (losses) on AFS securities from OCI | $ | 128 |  |  | $ | 4 |  |  |  |  |  |  |
Gains from recoveries (credit losses) on AFS securities | (106) |  |  | 34 |  |  |  |  |  |  |
Net realized gains (losses) on loans | — |  |  | (1,518) |  |  |  |  |  |  |
Net realized gains (losses) on equity securities | (1,853) |  |  | (16,564) |  |  |  |  |  |  |
Net realized gain on corporate bonds | 1,816 |  |  | 4 |  |  |  |  |  |  |
Other | 2,577 |  |  | 734 |  |  |  |  |  |  |
Tiptree Capital |  |  |  |  |  |  |  |  |
Mortgage: |  |  |  |  |  |  |  |  |
Net realized gains (losses) on loans | 24,733 |  |  | 17,520 |  |  |  |  |  |  |
Other | 965 |  | (1,377) |  |  |  |  |  |  |
Other: |  |  |  |  |  |  |  |  |
Net realized gains (losses) on loans (1) | 13,887 |  |  | 6,837 |  |  |  |  |  |  |
Other | 669 |  |  | (350) |  |  |  |  |  |  |
Total net realized gains (losses) | 42,816 |  |  | 5,324 |  |  |  |  |  |  |
Net unrealized gains (losses) |  |  |  |  |  |  |  |  |
Insurance: |  |  |  |  |  |  |  |  |
Net change in unrealized gains (losses) on loans | 856 |  |  | (2,160) |  |  |  |  |  |  |
Net unrealized gains (losses) on equity securities held at period end | 11,087 |  |  | (25,770) |  |  |  |  |  |  |
Reclass of unrealized (gains) losses from prior periods for equity securities sold | (1,211) |  |  | 16,252 |  |  |  |  |  |  |
Other | (3,622) |  |  | (4,619) |  |  |  |  |  |  |
Tiptree Capital |  |  |  |  |  |  |  |  |
Mortgage: |  |  |  |  |  |  |  |  |
Net change in unrealized gains (losses) on loans | (1,642) |  |  | (401) |  |  |  |  |  |  |
Other | 6,023 |  |  | (3,027) |  |  |  |  |  |  |
Other: |  |  |  |  |  |  |  |  |
Net change in unrealized gains (losses) on loans (1) | (1,900) |  |  | (252) |  |  |  |  |  |  |
Net unrealized gains (losses) on equity securities held at period end | 13,767 |  |  | (48,551) |  |  |  |  |  |  |
Other | 3,197 |  |  | 763 |  |  |  |  |  |  |
Total net unrealized gains (losses) | 26,555 |  |  | (67,765) |  |  |  |  |  |  |
Total net realized and unrealized gains (losses) | $ | 69,371 |  |  | $ | (62,441) |  |  |  |  |  |  |
(1) Primarily relates to Loans, at fair value classified as Held for Sale. See Note (4) Assets and Liabilities Held for Sale.

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