16 Non-GAAP Reconciliations – Underwriting & Fee Revenues & Margin ($ in thousands, except per share information) 2022 2021 2020 2022 2021 Total revenues 327,028$ 246,706$ 174,005$ 903,388$ 721,524$ Less: Net investment income (3,632) (3,330) (3,023) (10,164) (9,331) Less: Net realized and unrealized gains (losses) 6,382 7,492 (659) 23,151 (5,004) Underwriting and fee revenues 329,778$ 250,868$ 170,323$ 916,375$ 707,189$ 2022 2021 2020 2022 2021 Income (loss) before income taxes 15,304$ 13,337$ 13,447$ 39,057$ 49,569$ Less: Net investment income (3,632) (3,330) (3,023) (10,164) (9,331) Less: Net realized and unrealized gains (losses) 6,382 7,492 (659) 23,151 (5,004) Plus: Depreciation and amortization 4,742 4,307 2,329 13,697 12,905 Plus: Interest expense 5,027 4,268 3,988 15,166 13,097 Plus: Employee compensation and benefits 22,071 19,526 15,969 64,159 57,007 Plus: Other expenses 21,083 20,045 11,666 58,521 59,168 Underwriting and fee margin 70,977$ 65,645$ 43,717$ 203,587$ 177,411$ 2022 2021 2020 Total stockholders’ equity 519,574$ 402,142$ 361,691$ Less: Non-controlling interests (132,295) (16,930) (13,953) Total stockholders’ equity, net of non-controlling interests 387,279$ 385,212$ 347,738$ Total common shares outstanding 36,247 33,889 33,563 Book value per share 10.68$ 11.37$ 10.36$ Three Months Ended September 30, 2022 Nine Months Ended September 30, 2022 Three Months Ended September 30, 2022 Nine Months Ended September 30, 2022 As of September 30,
17 Non-GAAP Reconciliations – Adjusted Net Income ($ in thousands) Insurance Mortgage Other Corporate Total Insurance Mortgage Other Corporate Total Insurance Mortgage Other Corporate Total Income (loss) before taxes 15,304$ (940)$ 19,077 (8,316) 25,125 13,337$ 6,267$ (4,700) (11,320) 3,584 59,345$ 6,638$ 24,763 (50,876) 39,870 Less: Income tax (benefit) expense (3,765) 92 (3,963) 2,568 (5,068) (3,394) 14 1,591 1,552 (237) (18,380) (1,308) (4,111) (17,613) (41,412) Less: Net realized and unrealized gains (losses) 6,382 (82) (12,694) - (6,394) 7,428 (1,055) 10,396 - 16,769 24,423 (8,699) (7,872) - 7,852 Plus: Intangibles amortization (1) 4,115 - - - 4,115 3,830 - - - 3,830 15,976 - - - 15,976 Plus: Stock-based compensation expense 33 - 75 1,588 1,696 475 - 197 832 1,504 3,035 - 102 12,187 15,324 Plus: Non-recurring expenses 89 - 53 - 142 (28) - 448 - 420 1,643 - (660) 2,108 3,091 Plus: Non-cash fair value adjustments 0 - (130) - (130) - - (815) - (815) - - 2,551 - 2,551 Less: Tax on adjustments (2) (2,327) 153 3,238 (1,155) (91) (2,115) (1,265) (1,595) 650 (4,325) (5,767) 1,802 1,108 25,296 22,439 Adjusted net income 19,831$ (777)$ 5,656$ (5,315)$ 19,395$ 19,533$ 3,961$ 5,522$ (8,286)$ 20,730$ 80,275$ (1,567)$ 15,881$ (28,898)$ 65,691$ Average stockholders’ equity $ 319,703 $ 57,133 $ 84,445 $ 61,178 522,459$ $ 291,281 $ 68,925 $ 118,729 $ (75,340) 403,595$ $ 304,347 $ 60,218 $ 91,270 $ 5,024 460,858$ Adjusted return on average equity 24.8% -5.4% 26.8% NM% 14.8% 26.8% 23.0% 18.6% NM% 20.5% 26.4% -2.6% 17.4% NM% 14.3% Insurance Mortgage Other Corporate Total Insurance Mortgage Other Corporate Total Income (loss) before taxes 39,057$ 3,350$ 20,468 (33,895) 28,980 49,569$ 25,119$ 12,914 (33,151) 54,451 Less: Income tax (benefit) expense (11,099) (874) (3,469) (16,095) (31,537) (11,157) (4,448) (1,350) 5,539 (11,416) Less: Net realized and unrealized gains (losses) 23,151 (7,976) (8,293) - 6,882 (5,004) (5,075) (3,512) - (13,591) Plus: Intangibles amortization (1) 12,146 - - - 12,146 11,499 - - - 11,499 Plus: Stock-based compensation expense 2,376 - 98 5,437 7,911 1,347 331 209 1,831 3,718 Plus: Non-recurring expenses 1,561 - (869) 2,108 2,800 2,076 - 729 2,171 4,976 Plus: Non-cash fair value adjustments 0 - 3,554 - 3,554 - - (2,167) - (2,167) Less: Tax on adjustments (2) (7,299) 1,984 1,783 21,629 18,097 (1,930) (442) 1,330 582 (460) Adjusted net income 59,893$ (3,516)$ 13,272$ (20,816)$ 48,833$ 46,400$ 15,485$ 8,153$ (23,028)$ 47,010$ Average stockholders’ equity $ 309,042 $ 58,558 $ 94,169 $ (1,891) 459,878$ $ 296,125 $ 62,093 $ 110,818 $ (81,196) 387,840$ Adjusted return on average equity 25.8% -8.0% 18.8% NM% 14.2% 20.9% 33.3% 9.8% NM% 16.2% Three Months Ended September 30, 2021 Trailing Twelve Months Ended September 30, 2022 Tiptree CapitalTiptree Capital Three Months Ended September 30, 2022 Tiptree Capital Nine Months Ended September 30, 2022 Nine Months Ended September 30, 2021 Tiptree Capital Tiptree Capital The footnotes below correspond to the tables above, under “— Adjusted Net Income - Non-GAAP and “—Adjusted Return on Average Equity - Non-GAAP”. Adjusted net income is presented before the impacts of non- controlling interests. Tiptree’s subsidiary ownership percentage as of September 30, 2022 was Fortegra 79.5%, Tiptree Marine 95%, Reliance (Mortgage) 97%. (1) Specifically associated with acquisition purchase accounting. See Note (9) Goodwill and Intangible Assets, net. (2) Tax on adjustments represents the tax applied to the total non- GAAP adjustments and includes adjustments for non-recurring or discrete tax impacts. For the three, six and twelve months ended June 30, 2022, included in the adjustment is an add-back of $25.5 million related to deferred tax expense from the WP Transaction.