Investor Presentation – Second Quarter 2022 August 2022 Financial Information for the three and six months ended June 30, 2022 EXHIBIT 99.2

1 Disclaimers LIMITATIONS ON THE USE OF INFORMATION This presentation has been prepared by Tiptree Inc. and its consolidated subsidiaries (“Tiptree", "the Company" or "we”) solely for informational purposes, and not for the purpose of updating any information or forecast with respect to Tiptree, its subsidiaries or any of its affiliates or any other purpose. Tiptree reports a non-controlling interest in certain operating subsidiaries that are not wholly owned. Unless otherwise noted, all information is of Tiptree on a consolidated basis before non-controlling interest. Neither Tiptree nor any of its affiliates makes any representation or warranty, express or implied, as to the accuracy or completeness of the information contained herein and no such party shall have any liability for such information. These materials and any related oral statements are not all-inclusive and shall not be construed as legal, tax, investment or any other advice. You should consult your own counsel, accountant or business advisors. Performance information is historical and is not indicative of, nor does it guarantee future results. There can be no assurance that similar performance may be experienced in the future. SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS This document contains "forward-looking statements" which involve risks, uncertainties and contingencies, many of which are beyond Tiptree's control, which may cause actual results, performance, or achievements to differ materially from anticipated results, performance, or achievements. All statements contained herein that are not clearly historical in nature are forward-looking, and the words "anticipate," "believe," "estimate," "expect,“ “intend,” “may,” “might,” "plan," “project,” “should,” "target,“ “will,” "view," “confident,” or similar expressions are intended to identify forward-looking statements. Such forward-looking statements include, but are not limited to, statements about Tiptree's plans, objectives, expectations and intentions. The forward-looking statements are not guarantees of future performance and are subject to risks, uncertainties and other factors, many of which are beyond our control, are difficult to predict and could cause actual results to differ materially from those expressed or forecast in the forward-looking statements. Our actual results could differ materially from those anticipated in these forward-looking statements as a result of various factors, including, but not limited to those described in the section entitled “Risk Factors” in Tiptree’s Annual Report on Form 10-K, and as described in the Tiptree’s other filings with the SEC. Readers are cautioned not to place undue reliance on these forward-looking statements, which speak only as to the date of this release. The factors described therein are not necessarily all of the important factors that could cause actual results or developments to differ materially from those expressed in any of our forward-looking statements. Other unknown or unpredictable factors also could affect our forward-looking statements. Consequently, our actual performance could be materially different from the results described or anticipated by our forward-looking statements. Given these uncertainties, you should not place undue reliance on these forward-looking statements. Except as required by the federal securities laws, we undertake no obligation to update any forward- looking statements. MARKET AND INDUSTRY DATA Certain market data and industry data used in this presentation were obtained from reports of governmental agencies and industry publications and surveys. We believe the data from third-party sources to be reliable based upon our management’s knowledge of the industry, but have not independently verified such data and as such, make no guarantees as to its accuracy, completeness or timeliness. NOT AN OFFER OR A SOLICIATION This document does not constitute an offer or invitation for the sale or purchase of securities or to engage in any other transaction with Tiptree, its subsidiaries or its affiliates. The information in this document is not targeted at the residents of any particular country or jurisdiction and is not intended for distribution to, or use by, any person in any jurisdiction or country where such distribution or use would be contrary to local law or regulation. NON-GAAP MEASURES In this document, we sometimes use financial measures derived from consolidated financial data but not presented in our financial statements prepared in accordance with U.S. generally accepted accounting principles ("GAAP"). Certain of these data are considered “non-GAAP financial measures” under the SEC rules. These non-GAAP financial measures supplement our GAAP disclosures and should not be considered an alternative to the GAAP measure. Management's reasons for using these non-GAAP financial measures and the reconciliations to their most directly comparable GAAP financial measures are posted in the Appendix.

2 Q2 2022 Year-to-date Highlights Revenue $664.7 million 11.8% vs. prior year Adjusted Net Income2 $29.4 million 12.0% vs. prior year Book Value per share2,3 $10.75 2.7% vs. 3/31/22 Net Loss1 $(23.4) million vs. prior year net income of $36.6 million Overall  Adj. net income2 of $29.4mm, with a 12.7% adj. ROAE2, driven by strong performance in insurance & shipping.  Closed the previously announced $200 million strategic investment in Fortegra by Warburg Pincus.  Repaid $112.5mm of corporate debt.  Initiated exit of dry-bulk investments with expected gain of ~$21mm, or 45% as compared to Q1’22 book value. Expect sales to close in Q3’22.  Repurchased 89,543 shares in the quarter at an average price of $10.45 per share. Insurance  $1,196mm of gross written premiums and premium equivalents (GWPPE)4, 16% increase from PY driven by growth in specialty admitted & E&S insurance lines & fee-based service contract offerings.  Improved combined ratio of 90.7% from 91.8% in PY, driven by operating efficiencies.  Adj. net income of $40.1mm, up 49% from PY driven by revenue growth & improved combined ratio. Adj. ROAE of 25.5%.  Acquired ITC Compliance further expanding its presence in Europe. Tiptree Capital  Mortgage & shipping contributed pre-tax income of $20.7mm, partially offset by mark-to-market losses. ($ in millions, except per share information) 1 Net income (loss) attributable to common stockholders. 2 For a reconciliation of Non-GAAP metrics Adjusted net income, adjusted return on average equity and book value per share to GAAP financials, see the Appendix. 3 Quarterly total return defined as cumulative dividends paid of $0.04 per share plus book value per share as of June 30, 2022. 4 Gross written premium and premium equivalents are the base used to calculate the service fee income for non-insurance products. This base includes the amount charged to end consumers for a warranty or a car club membership.

Financial Results Q2’21 Q2'22 Q2’21 YTD Q2’22 YTD Total Revenues $299.7 $339.8 $594.4 $664.7 Net income (loss) $8.0 $(22.4) $36.6 $(23.4) Diluted EPS $0.22 $(0.64) $1.05 $(0.67) Adjusted net income1 $13.1 $14.0 $26.3 $29.4 Adjusted ROAE1 13.1% 12.3% 13.5% 12.7% Total shares outstanding 33.4 36.3 33.4 36.3 Book Value per share1 $11.59 $10.75 $11.59 $10.75 31 For a reconciliation of Non-GAAP metrics Adjusted net income, adjusted return on average equity and book value per share to GAAP financials, see the Appendix. 2 Includes dividends paid. Quarterly total return defined as dividends paid of $0.04 per share plus book value per share as of June 30, 2022. ($ in millions, except per share information) $9.0 $14.1 $18.9 $7.2 $6.1 $3.9 $(5.7) $(7.1) $(8.9) $10.5 $13.1 $14.0 Q2'20 Q2'21 Q2'22 Corporate Fortegra Tiptree Capital Key Highlights – Q2’22 Adjusted Net Income by business Fortegra Investment • Closing of the Warburg investment resulted in $63.2mm pre-tax impact to equity, offset by $39.6mm of tax expense related to the tax deconsolidation of Fortegra • Of the total deferred tax liability, $25.5mm impacted net income with $14.1mm offsetting the gain in stockholders’ equity directly. Adj net income of $14.0mm, increased by 6.6% versus prior year; • Continued revenue growth and improvements in Fortegra’s combined ratio, strong contributions from shipping, offset partially by declines in mortgage business Net income of $(22.4)mm resulting from tax expense on Fortegra transaction • Unrealized investment losses more than offset improvement in operations BVPS of $10.75 decreased by 5.9%2 over PY; up 2.7%2 from PQ • Interest rate movements drove unrealized losses on fixed income securities (impacting AOCI); expect to be able to hold to maturity • Partially offset by positive impacts to BV from Fortegra transaction closing $17.7 $26.9 $40.1 $10.7 $14.2 $4.9 $(11.0) $(14.7) $(15.5) $17.4 $26.3 $29.4 Q2'20 YTD Q2'21 YTD Q2'22 YTD

Specialty Insurance Performance Highlights Q2’22

5 Fortegra – Financial Performance Highlights Product & distribution expansion to drive continued growth, while maintaining underwriting discipline • Unearned premiums and deferred revenue grew to $1.8Bn, a 26% increase year-over-year • Underwriting and fee revenues increased to $301mm, up 21% • Continued investment in strategic initiatives ✓ Specialty admitted & E&S lines ✓ Capital-light warranty solutions ✓ European expansion Produced stable, growing results from underwriting and fees • Underwriting margin of $68mm, up 19%, driven by growth in U.S. Insurance and European lines • Combined ratio improved to 90.9% Capital and liquidity remain strong and continue to support growth objectives Underwriting and Fee Margin1 Underwriting and Fee Revenues1 Combined Ratio 1 2 3 Summary Financials Insurance products Q2’22 Highlights & Outlook 35 41 21 22 1 6 $57 $68 Q2'21 Q2'22 179 217 56 6714 16 $249 $301 Q2'21 Q2'22 76.7% 77.2% 15.5% 13.7% 92.1% 90.9% Q2'21 Q2'22 ($ in millions) U.S. Warranty Solutions U.S Insurance Europe Warranty Solutions Expense Ratio Underwriting Ratio Europe Warranty Solutions U.S. Warranty Solutions U.S. Insurance 1 See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income, Adjusted return on average equity, underwriting and fee revenues and underwriting and fee margin. 2 Gross written premiums and premium equivalents are the base used to calculate the service fee income for non-insurance products. This base includes the amount charged to end consumers for a warranty or a car club membership. Q2’21 Q2’22 Q2’21 YTD Q2’22 YTD Premiums & equivalents2 $552.8 $594.7 $1,030.0 $1,195.6 Revenue $252.3 $293.8 $474.8 $576.4 Pre-tax income (loss) $14.7 $9.1 $36.2 $23.8 Adjusted net income1 $14.1 $18.9 $26.9 $40.0 Adjusted ROAE1 20.1% 24.5% 18.3% 25.5% Combined ratio 92.1% 90.9% 91.8% 90.7% Unearned Premiums & Deferred Revenues $1,441.2 $1,812.0

Growth oriented while maintaining underwriting profitability 77.1% 75.1% 75.5% 77.4% 16.2% 17.7% 16.3% 13.3% 93.3% 92.9% 91.8% 90.7% Q2'19 Q2'20 Q2'21 Q2'22 $14.1 $17.7 $26.9 $40.1 Q2'19 Q2'20 Q2'21 Q2'22 6 ($ in millions, all figures represent Q2 year-to-date) Gross Written Premiums & Equivalents1 Underwriting & Fee Revenues and Margin2 Adjusted Net Income2 432 440 689 783 119 250 301 346 23 22 40 67 $573 $711 $1,030 $1,196 Q2'19 Q2'20 Q2'21 Q2'22 Combined Ratio Adj. ROAE%1 Adj. Net Income U/W Ratio Expense Ratio U.S. Insurance U.S. Warranty Solutions Europe Warranty Solutions 1 Gross written premiums and premium equivalents are the base used to calculate the service fee income for non-insurance products. This base includes the amount charged to end consumers for a warranty or a car club membership. 2 See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income, Adjusted return on average equity, underwriting and fee revenues and underwriting and fee margin. 11% 19% U/W & Fee Revenues U/W & Fee Margin 26%13% 251 247 329 428 43 75 107 128 1 9 20 30 $295 $330 $456 $587 Q2'19 Q2'20 Q2'21 Q2'22 49 50 65 80 19 28 42 42 0 4 5 10 $68 $82 $112 $133 Q2'19 Q2'20 Q2'21 Q2'22

Investment Portfolio Cash & Equivalents 26% Government & Agency 37% Corporate Bonds 17% Fixed Income ETFs 6% Muni & ABS 6% Equities 2% Other Alternatives 6% Cash & Equivalents 28% Government & Agency 40% AAA 2% AA 8% A 15% BBB 1% Fixed Income ETFs 6% $926mm 7 Asset Allocation Liquid and Highly-Rated Fixed Income Portfolio ($ in millions) 623 926 191 84 $815 $1,011 Q2'21 Q2'22 Other investments Fixed Income & Cash Return Metrics (Pre-tax) $1,011mm ◼ ~2.6 year duration ◼ AA+ rating ◼ 1.2% book yield Q2’21 Q2'22 Q2’21 YTD Q2’22 YTD Net investment income $3.2 $3.4 $6.0) $6.5 Net realized and unrealized gains (losses) $2.8 $(10.1) $12.5 $(16.8)

77.1 82.3 74.1 57.6 39.9 17.5 4.4 2.6 $195.5 $160.0 Q2'21 Q2'22 Financial drivers Pre-tax income (loss) Q2’21 Q2’22 Q2’21 YTD Q2’22 YTD Mortgage $5.8 $0.0 $18.9 $4.3 Senior living (Invesque)2 0.1 (2.7) 13.9 (11.5) Maritime transportation 2.0 13.8 2.5 16.4 Other 0.5 (2.0) 1.2 (3.5) Total $8.4 $9.1 $36.5 $5.7 9 Tiptree Capital – Financial Performance Highlights Mortgage: • Mortgage origination volumes of $661mm, down 17% from PY • Pre-tax income below PY from decline in volume & margins, partially offset by higher servicing fees & positive FV adjustments on MSR • MSRs of $41mm, including $1.6mm positive MTM in Q2’22 Maritime transportation: • Charter rates remain strong • Favorable valuations led to strategic sales of dry bulk vessels Senior living (Invesque – IVQ.U): • Observing positive operating trends in some healthcare real estate sectors • Unrealized losses of $11.5mm, compared to PY gains of $13.9mm Mortgage Maritime transportation Seniors Housing (Invesque/Care)2 1 See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income. 2 17.0m of Invesque common shares, 2.9m shares held in the insurance company investment portfolio. On balance sheet at fair value - $20.9 million, $17.3 million in Tiptree Capital as of June 30, 2022. Capital Allocation Q2’22 Year-to-date Highlights ($ in millions) Other

Financial Snapshot 11 ($ in millions) LTM Adjusted Net Income1 1) See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income. 2) Estimated based on Warburg Pincus valuation multiple of 13.5x Adj. Net Income, multiplied by LTM Adj. Net Income of $80.0 million, multiplied by Tiptree’s 72.6% as converted ownership as of Q2’22, less deferred tax liability of $39.6 million recorded as of Q2’22. 3) Includes Tiptree Inc. stockholders’ equity of Mortgage, Tiptree Capital – Other and Corporate, excluding the deferred tax liability relating to Tiptree’s investment in Fortegra. 4) Diluted shares as of June 30, 2022, represents basic outstanding shares of 36,305,016 plus dilutive shares of 1,172,940 which includes unvested RSUs and outstanding options (assumed to be exercised cashless). Adj ROAE% 16.0% 14.4% Sum of the Parts $60.3 $67.0 Q2'21 Q2'22 $744 million2 (Transaction multiple) $235 million3 (Book value ex. NCI) $979 million $19.85 Value/TIPT diluted share4 Pro-forma SOTP Value $6.27 $26.12

12 ❑ Significant opportunities ahead to achieve value creation objectives at Fortegra ❑ Continued focus on long-term value creating opportunities Summary & Outlook ($ in millions) ✓ Strong operating performance from our businesses – Fortegra continues to deliver record top-line and return on equity – Solid contributions from favorable shipping environment both in charter rates and vessel valuations ✓ $200mm investment in Fortegra from Warburg Pincus closed in Jun’22 1 See the appendix for a reconciliation of Non-GAAP measures including Adjusted Net Income and Adjusted return on average equity. First Half 2022 Highlights Looking Ahead

Appendix Non-GAAP Reconciliations • Insurance underwriting and fee revenue • Insurance underwriting and fee margin • Book Value per share • Adjusted net income

Q2’22 Capital Allocation & Annual Performance Comparison 141 Represents total stockholders’ equity. Total stockholders’ equity net of non-controlling interests was $390.4 million as of June 30, 2022. 2 See the appendix for a reconciliation of Non-GAAP metrics including Adjusted net income and adjusted return on average equity. Adjusted net income of $67.0mm, up 11.2% from Q2’21 LTM • Adjusted return on average equity of 14.4%1 Fortegra: 26.1% Adj. ROAE • Growth in insurance underwriting and fee revenues • Combined ratio improvement • Expect continued growth in specialty and warranty lines Tiptree Capital: 10.6% Adj. ROAE • Positive operating contributions from shipping investments • Mortgage business margins and volumes normalize Q2’22 LTM Highlights Stockholders’ Equity1 Adjusted Net Income2 Business Lines Q2’22 Q2’21 LTM Q2’22 LTM Fortegra $325.3 $52.6 $80.0 - Underwriting & fees $44.4 $68.3 - Investments $8.2 $11.7 Tiptree Capital $160.0 $36.5 $18.9 Corporate $40.1 $(28.8) $(31.9) Total Tiptree $525.3 $60.3 $67.0 ($ in millions) LTM Operating Performance

Non-GAAP Reconciliations 15 Adjusted Net Income We define adjusted net income as income before taxes, less provision (benefit) for income taxes, and excluding the after-tax impact of various expenses that we consider to be unique and non-recurring in nature, including merger and acquisition related expenses, stock-based compensation, net realized and unrealized gains (losses) and intangibles amortization associated with purchase accounting. We use adjusted net income as an internal operating performance measure in the management of business as part of our capital allocation process. We believe adjusted net income provides useful supplemental information to investors as it is frequently used by the financial community to analyze financial performance between periods and for comparison among companies. Adjusted net income should not be viewed as a substitute for income before taxes calculated in accordance with GAAP, and other companies may define adjusted net income differently. We present adjustments for amortization associated with acquired intangible assets. The intangible assets were recorded as part of purchase accounting in connection with Tiptree’s acquisition of FFC in 2014, Defend in 2019, and Smart AutoCare and Sky Auto in 2020. The intangible assets acquired contribute to overall revenue generation, and the respective purchase accounting adjustments will continue to occur in future periods until such intangible assets are fully amortized in accordance with the respective amortization periods required by GAAP. We define adjusted return on average equity as adjusted net income expressed on an annualized basis as a percentage of average beginning and ending stockholder’s equity during the period. We use adjusted return on average equity as an internal performance measure in the management of our operations because we believe it gives our management and other users of our financial information useful insight into our results of operations and our underlying business performance. Adjusted return on average equity should not be viewed as a substitute for return on average equity calculated in accordance with GAAP, and other companies may define adjusted return on average equity differently. Book value per share Management believes the use of book value per share provides supplemental information useful to investors as it is frequently used by the financial community to analyze company growth on a relative per share basis. Insurance – Underwriting and Fee Revenues We generally manage our exposure to the underwriting risk we assume using both reinsurance (e.g., quota share and excess of loss) and retrospective commission agreements with our partners (e.g., commissions paid are adjusted based on the actual underlying losses incurred), which mitigate our risk. Period-over-period comparisons of revenues and expenses are often impacted by the PORCs and distribution partners’ choice as to whether to retain risk, specifically service and administration fees and ceding commissions, both components of revenue, and policy and contract benefits and commissions paid to our partners and reinsurers. Generally, when losses are incurred, the risk which is retained by our partners and reinsurers is reflected in a reduction in commissions paid. In order to better explain to investors the underwriting performance of the Company’s programs and the respective retentions between the Company and its agents and reinsurance partners, we use the non-GAAP metrics underwriting and fee revenues and underwriting and fee margin. We define underwriting and fee revenues as total revenues from our Insurance segment excluding net investment income, net realized and unrealized gains (losses). Underwriting and fee revenues represents revenues generated by our underwriting and fee-based operations and allows us to evaluate our underwriting performance without regard to investment income. We use this metric as we believe it gives our management and other users of our financial information useful insight into our underlying business performance. Underwriting and fee revenues should not be viewed as a substitute for total revenues calculated in accordance with GAAP, and other companies may define underwriting and fee revenues differently. Insurance - Underwriting and Fee Margin We define underwriting and fee margin as income before taxes from our Insurance segment, excluding net investment income, net realized and unrealized gains (losses), employee compensation and benefits, other expenses, interest expense and depreciation and amortization. Underwriting and fee margin represents the underwriting performance of our underwriting and fee-based programs. As such, underwriting and fee margin excludes general administrative expenses, interest expense, depreciation and amortization and other corporate expenses as those expenses support the vertically integrated business model and not any individual component of our business mix. We use this metric as we believe it gives our management and other users of our financial information useful insight into the specific performance of our underlying underwriting and fee program. Underwriting and fee income should not be viewed as a substitute for income before taxes calculated in accordance with GAAP, and other companies may define underwriting and fee margin differently.

16 Non-GAAP Reconciliations – Underwriting & Fee Revenues & Margin We define underwriting and fee revenues as total revenues from our Insurance segment excluding net investment income, net realized and unrealized gains (losses). Underwriting and fee revenues represents revenues generated by our underwriting and fee-based operations and allows us to evaluate our underwriting performance without regard to investment income. We use this metric as we believe it gives our management and other users of our financial information useful insight into our underlying business performance. Underwriting and fee revenues should not be viewed as a substitute for total revenues calculated in accordance with GAAP, and other companies may define underwriting and fee revenues differently. We define underwriting and fee margin as income before taxes from our Insurance segment, excluding net investment income, net realized and unrealized gains (losses), employee compensation and benefits, other expenses, interest expense and depreciation and amortization. Underwriting and fee margin represents the underwriting performance of our underwriting and fee-based programs. As such, underwriting and fee margin excludes general administrative expenses, interest expense, depreciation and amortization and other corporate expenses as those expenses support the vertically integrated business model and not any individual component of our business mix. We use this metric as we believe it gives our management and other users of our financial information useful insight into the specific performance of our underlying underwriting and fee program. Underwriting and fee income should not be viewed as a substitute for income before taxes calculated in accordance with GAAP, and other companies may define underwriting and fee margin differently. Management uses Book value per share, which is a non-GAAP financial measure. Management believes the use of this financial measure provides supplemental information useful to investors as it is frequently used by the financial community to analyze company growth on a relative per share basis. ($ in thousands, except per share information) Three Months Ended June 30, 2022 2021 2020 Total revenues $ 293,831 $ 252,255 $ 164,953 Less: Net investment income (3,365) (3,234) (2,292) Less: Net realized and unrealized gains (losses) 10,126 (2,824) (5,633) Underwriting and fee revenues $ 300,592 $ 246,197 $ 157,028 Three Months Ended June 30, 2022 2021 2020 Income (loss) before income taxes $ 14,682 $ 14,704 $ 14,088 Less: Net investment income (3,167) (3,234) (2,292) Less: Net realized and unrealized gains (losses) 6,643 (2,824) (5,633) Plus: Depreciation and amortization 4,354 4,407 2,630 Plus: Interest expense 4,759 4,525 3,582 Plus: Employee compensation and benefits 22,026 18,392 14,916 Plus: Other expenses 14,839 21,491 12,687 Underwriting and fee margin $ 64,136 $ 57,461 $ 39,978 As of June 30, 2022 2021 2020 Total stockholders’ equity $ 525,340 $ 405,049 $ 347,189 Less: Non-controlling interests 134,935 18,031 11,368 Total stockholders’ equity, net of non-controlling interests $ 390,405 $ 387,018 $ 335,821 Total common shares outstanding 36,305 33,395 33,700 Book value per share $ 10.75 $ 11.59 $ 9.97 Six Months Ended, June 30, 2022 2021 $ 576,360 $ 474,818 (6,532) (6,001) 16,769 (12,496) $ 586,597 $ 456,321 Six Months Ended June 30, 2022 2021 $ 29,386 $ 36,232 (6,401) (6,001) 3,819 (12,496) 8,761 8,598 9,284 8,829 40,418 37,481 36,330 39,123 $ 121,597 $ 111,766

17 Non-GAAP Reconciliations – Adjusted Net Income Three Months Ended June 30, 2022 Tiptree Capital ($ in thousands) Insurance Mortgage Other Corporate Total Income (loss) before taxes 9,071 24 9,041 (13,330) 4,806 Less: Income tax (benefit) expense -3,670 12 (1,300) (21,597) -26,555 Less: Net realized and unrealized gains (losses) 10,126 (1,580) (4,450) - 4,096 Plus: Intangibles amortization (1) 4,085 - - - 4,085 Plus: Stock-based compensation expense 24 - 23 10 57 Plus: Non-recurring expenses 1,449 - (1,055) 2,108 2,502 Plus: Non-cash fair value adjustments - - 2,170 - 2,170 Less: Tax on adjustments (2) (2,147) 361 658 23,952 22,824 Adjusted net income 18,938 (1,183) 5,087 (8,857) 13,985 Adjusted net income 18,938 (1,183) 5,087 (8,857) 13,985 Average stockholders’ equity 309,774 57,537 108,019 (21,082) 454,248 Adjusted return on average equity 24.5% -8.2% 18.8% NM% 12.3% Three Months Ended June 30, 2021 Tiptree Capital Insurance Mortgage Other Corporate Total 14,704 5,775 2,620 (11,624) 11,475 (3,334) (1,366) (34) 2,307 (2,427) (2,808) (600) (142) - (3,550) 3,835 - - - 3,835 500 166 4 479 1,149 1,834 - 281 2,171 4,286 - - (695) - (695) (640) 84 30 (422) (948) 14,091 4,059 2,064 (7,089) 13,125 14,091 4,059 2,064 (7,089) 13,125 281,041 72,364 121,129 (73,310) 401,224 20.1% 22.4% 6.8% NM% 13.1% Six Months Ended June 30, 2022 Tiptree Capital ($ in thousands) Insurance Mortgage Other Corporate Total Income (loss) before taxes 23,753 4,290 1,391 (25,579) 3,855 Less: Income tax (benefit) expense (7,334) (966) 494 (18,663) (26,469) Less: Net realized and unrealized gains (losses) 16,769 (7,894) 4,401 - 13,276 Plus: Intangibles amortization (1) 8,031 - - - 8,031 Plus: Stock-based compensation expense 2,343 - 23 3,849 6,215 Plus: Non-recurring expenses 1,472 - (922) 2,108 2,658 Plus: Non-cash fair value adjustments - - 3,684 - 3,684 Less: Tax on adjustments (2) (4,972) 1,831 (1,455) 22,784 18,188 Adjusted net income 40,062 (2,739) 7,616 (15,501) 29,438 Adjusted net income 40,062 (2,739) 7,616 (15,501) 29,438 Average stockholders’ equity 314,592 58,981 112,190 (23,001) 462,762 Adjusted return on average equity 25.5% -9.3% 13.6% NM% 12.7% Six Months Ended June 30, 2021 Tiptree Capital Insurance Mortgage Other Corporate Total 36,232 18,852 17,614 (21,831) 50,867 (7,763) (4,462) (2,941) 3,987 (11,179) (12,432) (4,020) (13,908) - (30,360) 7,669 - - - 7,669 872 331 12 999 2,214 2,104 - 281 2,171 4,556 - - (1,352) - (1,352) 185 823 2,925 (68) 3,865 26,867 11,524 2,631 (14,742) 26,280 26,867 11,524 2,631 (14,742) 26,280 292,865 67,292 113,430 (84,295) 389,292 18.3% 34.3% 4.6% NM% 13.5% The footnotes below correspond to the tables above, under “—Adjusted Net Income - Non- GAAP and “—Adjusted Return on Average Equity - Non-GAAP”. (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. Trailing Twelve Ended June 30, 2022 Tiptree Capital Insurance Mortgage Other Corporate Total 57,378 13,845 986 (53,880) 18,329 (18,009) (1,386) 1,443 (18,629) (36,581) 25,469 (9,672) 15,218 0 31,015 15,691 0 0 0 15,691 3,477 0 224 11,431 15,132 1,526 0 (265) 2,108 3,369 0 0 1,866 0 1,866 (5,555) 384 (3,725) 27,101 18,205 79,977 3,171 15,747 (31,869) 67,026 79,977 3,171 15,747 (31,869) 67,026 306,637 65,841 111,902 (19,186) 465,195 26.1% 4.8% 14.1% NM% 14.4%