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Tiptree Announces $200mm Investment by Warburg Pincus in Fortegra Investment Will Accelerate Growth Opportunities October 12, 2021 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. 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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 Transaction Summary $200mm strategic investment in Fortegra by Warburg Pincus, representing a 24% ownership1 stake in Fortegra Strategic Rationale Warburg Pincus is a leading private equity firm with significant related investment experience Highlights the underlying value of Fortegra Allows for recapitalization of Tiptree through repayment of debt Provides capital to accelerate growth Validates Fortegra’s growth story and brings new relationships to drive business opportunities ✓ ✓ ✓ ✓ ✓ 1) 24% Warburg Pincus Ownership of Fortegra Group presented on an as converted basis, excluding warrants.

3 Details of the Transaction • $140 million1 to repay existing Tiptree indebtedness and for general corporate purposes • $60 million to support Fortegra’s growth opportunities, funded as needed Use of Proceeds • $120 million investment representing approximately 17.5% of the company o $691 million post-money equity value for Fortegra o Includes 33% warrant coverage2 at a 33% valuation premium Common Stock Investment • Committed to a $200 million investment in Fortegra by Warburg Pincus o $120 million common equity o $80 million convertible preferred • Represents 24% ownership interest in Fortegra on an as-converted basis • Expected to close in the first quarter of 2022, subject to regulatory approvals Investment • $80 million investment representing an additional 6.6% of the company on an as-converted basis • Dividends of 8.0% per annum payable in cash or in-kind Convertible Preferred Investment 1) $110 million to extinguish Fortress indebtedness, which was assumed from Tiptree. $30 million to repay notes to Tiptree, to be used for general corporate purposes. 2) Excludes Additional Warrants which are subject to achieving certain performance metrics described in the transaction 8K.

NASDAQ: TIPT Market Cap: $356 million Share Price: $10.49 Shares outstanding: 33.9 million (As of 10/8/2021) $549 million1 (Transaction valuation) $187 million (Book value ex. NCI) Holding Company $62 million2 (Book value) $798 million $16.20 Value per TIPT share Pro-forma SOTP Value $5.52 $1.83 $23.55 All Data is as of June 30, 2021 pro-forma for the impact of the Warburg Pincus investment in Fortegra, which was signed on October 11, 2021. 1) Based on investment post money valuation of $691 million, multiplied by Tiptree’s 79.5% ownership pro-forma as of closing date. 2) Represents Q2’21 Tiptree holding company book equity of $(78) million plus $140 million of transaction proceeds that will be used to extinguish $110 million of Fortress indebtedness, which was assumed from Tiptree, and $30 million to repay notes to Tiptree, which will be used for general corporate purposes. 4

5 Reinforces Tiptree’s strategic objectives  Strategic partnership with Warburg Pincus is the first step toward our goal of demonstrating Fortegra’s intrinsic value  Continue to focus on long-term shareholder value creation ✓ Seek new acquisition opportunities ✓ Invest in existing subsidiaries ✓ Opportunistic share repurchases ✓ Maintain consistent dividends

Appendix

7 Overview of Fortegra $963 $1,096 $1,297 $1,667 $2,032 2017 2018 2019 2020 Q2'21 LTM ($ in millions) Established, growing, vertically integrated specialty insurer that focuses on niche insurance & capital-light fee business. Unique & diverse combination of underwriting and fee revenues (premium & premium equivalents) Target programs that have more frequency but significantly less severity & catastrophic risk Agent-driven business with a “one-to-many” distribution model with long-standing, economically aligned partnerships Scalable technology & deep industry expertise lay the path ahead to be a global market leader in specialty insurance 95% 5-year Agent Persistency Rate $288mm Q2’21 GAAP Equity 91% 5-year Average Combined Ratio A- A.M. Best & Kroll Ratings 18% Q2’21 LTM Adjusted ROAE 25 years Average Mgmt. Experience Differentiated approach has led to robust growth, consistent profitability & high cash flows Growth in GWPPE¹ ✓ ✓ ✓ ✓ ✓ 1) Gross written premium & premium equivalents.

8 Compelling Growth Story Fortegra is well-positioned to capitalize on a substantial opportunity in the insurance industry. Maintain & Expand Existing Programs ◼ $1.4Bn UEP & Deferred Revenue ◼ ~95% persistency with insurance agents ◼ Recent acquisitions to accelerate growth A U.S. Insurance U.S. Warranty Solutions Europe Warranty Solutions Unearned Premiums & Deferred Revenues 503 599 728 807 895 57 74 91 386 459 1 30 67 87 $560 $674 $849 $1,260 $1,441 2017 2018 2019 2020 Q2'21 New & Renewal Programs ◼ Excess & Surplus Insurance — Fortegra Specialty formed Q4’20 ◼ Admitted Insurance — Growth in new & renewal programs ◼ Warranty Solutions — Capital-light business model Continued Geographic Expansion ◼ Entered Europe in 2018 ◼ Central & Western Europe B C $56bn¹ $627bn² $53bn³ $31bn³ Addressable Market $62mm $1,265mm $634mm $71mm Fortegra LTM GWPPE 1) NAIC, 2020. 2) NAIC, 2019. 3) Allied Market Research, 2019 Extended Warranty Report, North America.

9 The Fortegra Difference Fortegra is a specialty program insurer. Consistency has been key to growth in GWPPE1 to $2.0Bn as of Q2'21 LTM. We marry underwriting & fee revenue to create consistent profitability & enhanced returns. CONSISTENT Profitability We win new business because of the breadth of our underwriting, administrative & financial offering. CONSISTENT Growth We maintain the business we win by expanding our agents’ ecosystem & maintaining a reasonable cost structure. CONSISTENT Risk Management 1) Gross written premium & premium equivalents.

TiptreeInc. ir@tiptreeinc.com