Fortegra sale to bring $1.12B to Tiptree (NASDAQ: TIPT)

Rhea-AI Filing Summary

Tiptree Inc. reported 2025 results and highlighted pending sales of Fortegra and Reliance First Capital that significantly reshape the business. The Fortegra deal values the unit at $1.65 billion, with an estimated $1.12 billion in gross proceeds to Tiptree, while the Reliance sale is expected to generate about $50 million of gross proceeds.

These divestitures are expected to produce estimated pro-forma book value of about $923 million, or $24.40 per share as of December 31, 2025. For 2025, Tiptree generated net income attributable to common stockholders of $34.9 million, with diluted earnings per share of $0.76, down from $1.34 in 2024, as continuing operations remained loss-making while discontinued operations were profitable.

Book value per share rose to $13.45 from $12.29, and the board declared a $0.06 per-share cash dividend for stockholders of record on March 16, 2026, payable March 23, 2026. Management emphasized a long-term, owner-oriented approach, combining strategic investments, potential share repurchases, and dividends.

Positive

• High-value divestitures and stronger pro-forma equity: Sale agreements for Fortegra at $1.65 billion (about $1.12 billion in gross proceeds to Tiptree) and Reliance at roughly $50 million are expected to lift estimated pro-forma book value to about $923 million, or $24.40 per share as of December 31, 2025.
• Book value per share growth: Book value per share increased from $12.29 to $13.45 as of December 31, 2025, reflecting net value creation even as the company prepares for major portfolio changes.

Negative

• Weaker earnings from continuing operations: For 2025, Tiptree recorded a net loss from continuing operations of about $38.9 million, and diluted EPS fell to $0.76 from $1.34 in 2024, indicating reduced overall profitability despite strong discontinued operations.

Insights

Equity analyst – special situations & capital allocation

Large asset sales at high valuations boost pro-forma equity but near-term earnings are softer.

Tiptree is executing two significant divestitures. The Fortegra sale at $1.65 billion (with an estimated $1.12 billion in gross proceeds) and the Reliance First Capital sale at about $50 million should substantially increase corporate liquidity and simplify the business mix after anticipated closings in 2026.

Management estimates pro-forma book value of roughly $923 million, or $24.40 per share as of December 31, 2025, highlighting the embedded value they see in the portfolio relative to the current GAAP book value per share of $13.45. However, 2025 diluted EPS declined to $0.76 from $1.34, with continuing operations generating losses while discontinued operations contributed profits.

The declared cash dividend of $0.06 per share with a record date of March 16, 2026 signals an ongoing capital return component alongside potential future reinvestment or buybacks. Actual long-term value creation will depend on how the sizeable expected Fortegra and Reliance proceeds are redeployed and how remaining and new businesses perform in subsequent periods.

0001393726false00013937262026-03-062026-03-06

UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
WASHINGTON, D.C. 20549

FORM 8-K

CURRENT REPORT

Pursuant to Section 13 or 15(d) of the Securities Exchange Act of 1934

Date of Report (Date of earliest event reported): March 06, 2026

Tiptree Inc.

(Exact name of Registrant as Specified in Its Charter)

Maryland			001-33549	38-3754322
(State or Other Jurisdiction of Incorporation)			(Commission File Number)	(IRS Employer Identification No.)
660 Steamboat Road 2nd Floor
Greenwich, Connecticut				06830
(Address of Principal Executive Offices)				(Zip Code)

Registrant’s Telephone Number, Including Area Code: 212 446-1400

(Former Name or Former Address, if Changed Since Last Report)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

☐Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)

☐Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)

☐Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))

☐Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:

Title of each class		Trading Symbol(s)		Name of each exchange on which registered
Common stock, par value $0.001 per share		TIPT		The Nasdaq Stock Market

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§ 230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§ 240.12b-2 of this chapter).

Emerging growth company ☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Item 2.02 Results of Operations and Financial Condition.

On March 6, 2026 Tiptree Inc. (the “Company” or “Tiptree”) issued a press release announcing its results of operations for the twelve months ended December 31, 2025. A copy of the press release is furnished as Exhibit 99.1 hereto and incorporated herein by reference.

Item 7.01 Regulation FD Disclosure.

Included in the press release furnished as Exhibit 99.1 was an announcement that the board of directors of the Company has declared a cash dividend of $0.06 per share to Tiptree’s stockholders, with a record date of March 16, 2026 and a payment date of March 23, 2026.

On March 6, 2026, the Company posted an investor presentation dated March 2026 on the Investor Resources section of www.tiptreeinc.com. The investor presentation is furnished as Exhibit 99.2 to this Form 8-K and incorporated herein by reference. Tiptree’s website is not intended to function as a hyperlink, and the information contained on such website is not a part of this Form 8-K.

The information in Items 2.02 and 7.01 of this Current Report on Form 8-K, including the information contained in Exhibits 99.1 and 99.2, shall not be deemed “filed” for the purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities under that Section. Furthermore, the information in Items 2.02 and 7.01 of this Current Report on Form 8-K, including the information contained in Exhibits 99.1 and 99.2, shall not be deemed to be incorporated by reference into the filings of the Company under the Securities Act of 1933, as amended (the “Securities Act”), or the Exchange Act, except as shall be expressly set forth by specific reference in such a filing.

Item 9.01 Financial Statements and Exhibits.

(d) List of Exhibits:

Exhibit No.		Description
99.1		Tiptree Inc. press release, dated March 6, 2026.
99.2		Tiptree Inc. Investor Presentation - March 2026.
104		Cover Page Interactive Data File (formatted as Inline XBRL).

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

			Tiptree Inc.
Date:	March 6, 2026		By:	/s/ Michael G. Barnes
			Name:	Michael G. Barnes
			Title:	Chairman and Chief Executive Officer

Exhibit 99.1

TIPTREE ANNOUNCES FOURTH QUARTER 2025 RESULTS

Greenwich, Connecticut – March 6, 2026- Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three months and year ended December 31, 2025.

The Company commented, "In late 2025, we agreed to sell Fortegra and Reliance First Capital, transactions expected to result in pro-forma book value of approximately $923 million, or $24.40 per share. Since our $139 million initial capital raise in 2007, we have completed more than 21 acquisitions and divestitures, returned over $180 million to shareholders, delivered an 11.1%(1) annual compounded return—outperforming both the Russell 2000 and S&P 500—and we believe we are well positioned to continue building on this record."

2025 Highlights

•On September 26, 2025, the Company agreed to sell Fortegra for $1.65 billion, with $1.12 billion estimated gross proceeds to Tiptree pending regulatory approvals. Anticipated closing of the Fortegra transaction in mid-2026.

•On October 31, 2025, the Company agreed to sell its mortgage business, Reliance First Capital, for 93.5% of tangible book value at closing, or $50 million of estimated gross proceeds as of December 31, 2025. Anticipated closing in first half of 2026.

•Tiptree's pro-forma book value as of December 31, 2025 is estimated to be $923 million, net of estimated taxes and transaction expenses for the closing of both transactions.

•Declared a dividend of $0.06 per share to stockholders of record on March 16, 2026 with a payment date of March 23, 2026.

•Tiptree will continue to think and act like owners—focused on long-term value creation through strategic investments, opportunistic share buybacks, and thoughtful consideration of dividends. With a disciplined financial approach, the Company continues to streamline operations and manage costs to support sustainable growth.

($ in thousands, except per share information)		Three Months Ended December 31,								Year Ended December 31,
GAAP:		2025				2024				2025				2024
Total revenues		$	3			$	372			$	488			$	1,520
Total expenses		$	8,618			$	9,579			$	47,212			$	41,794
Income (loss) before taxes		$	(8,690	)		$	(9,227	)		$	(44,602	)		$	(38,562	)
Net income (loss) from continuing operations		$	(9,306	)		$	(6,798	)		$	(38,911	)		$	(32,345	)
Net income (loss) from discontinued operations		$	15,183			$	26,347			$	73,838			$	85,712
Diluted earnings per share		$	0.04			$	0.49			$	0.76			$	1.34
Cash dividends paid per common share		$	0.06			$	0.31			$	0.24			$	0.49
Non-GAAP(2):
Book value per share		$	13.45			$	12.29			$	13.45			$	12.29

(1) Calculated using the initial book value per share of $5.36 at Tiptree's founding in 2007, pro-forma book value per share of $24.40 as of December 31, 2025 ,and cumulative dividends of $3.77 per share paid from 2007 through December 31, 2025.

(2) See “—Non-GAAP Reconciliations” for a discussion of non-GAAP financial measures.

About Tiptree

Tiptree Inc. (NASDAQ: TIPT) allocates capital to select small and middle market companies with the mission of building long-term value. Established in 2007, Tiptree has a significant track record investing across a variety of industries and asset types, including the insurance, asset management, specialty finance, real estate and shipping sectors. With proprietary access and a flexible capital base, Tiptree seeks to uncover compelling investment opportunities and support management teams in unlocking the full value potential of their businesses. For more information, please visit tiptreeinc.com and follow us on LinkedIn.

Page 1

Forward-Looking Statements

This release contains “forward-looking statements” which involve risks, uncertainties and contingencies, many of which are beyond the Company’s control, which may cause actual results, performance, or achievements to differ materially from anticipated results, performance, or achievements. All statements contained in this release 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,” or similar expressions are intended to identify forward-looking statements. Such forward-looking statements include, but are not limited to, statements about the Company’s plans, objectives, expectations for our businesses 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 the Company’s Annual Report on Form 10-K, and as described in the Company’s other filings with the Securities and Exchange Commission. 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.

Page 2

Tiptree Inc.

Condensed Consolidated Balance Sheets

($ in thousands, except share data)

		As of December 31,
		2025				2024
Assets:
Current assets:
Cash and cash equivalents		$	30,784			$	19,437
Marketable securities			21,701				15,024
Other current assets			2,361				3,705
Total current assets			54,846				38,166
Right of use asset			8,301				10,140
Property, plant and equipment, net			6,262				7,710
Other assets			2,269				3,122
Assets held for sale (1)			6,768,387				5,635,651
Total assets		$	6,840,065			$	5,694,789
Liabilities and Stockholders’ Equity
Liabilities:
Current liabilities:
Short-term debt, net		$	8,138			$	—
Other current liabilities			20,964				15,572
Total current liabilities			29,102				15,572
Long-term debt, net			63,948				—
Long-term lease obligations			8,654				11,137
Deferred tax liabilities			80,390				57,071
Liabilities held for sale (1)			5,905,572				4,954,238
Total liabilities		$	6,087,666			$	5,038,018
Stockholders’ Equity:
Preferred stock: $0.001 par value, 100,000,000 shares authorized, none issued or outstanding		$	—			$	—
Common stock: $0.001 par value, 200,000,000 shares authorized, 37,824,472 and 37,255,838 shares issued and outstanding, respectively			38				37
Additional paid-in capital			394,435				389,693
Accumulated other comprehensive income (loss), net of tax			(7,496	)			(27,750	)
Retained earnings			121,574				95,718
Total Tiptree Inc. stockholders’ equity			508,551				457,698
Non-controlling interests:
Fortegra preferred interests			77,679				77,679
Common interests			166,169				121,394
Total non-controlling interests			243,848				199,073
Total stockholders’ equity			752,399				656,771
Total liabilities and stockholders’ equity		$	6,840,065			$	5,694,789

(1)See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations for further details, as disclosed in Tiptree's 10-K filing for the period ended December 31, 2025.

Page 3

Tiptree Inc.

Condensed Consolidated Statements of Operations

($ in thousands, except share data)

		Three Months Ended December 31,								Year Ended December 31,
		2025				2024				2025				2024
Revenues:
Other revenue		$	3			$	372			$	488			$	1,520
Total revenues			3				372				488				1,520
Expenses:
Employee compensation and benefits			7,090				6,351				33,844				29,159
Depreciation and amortization			365				365				1,448				1,451
Other expenses			1,163				2,863				11,920				11,184
Total expenses			8,618				9,579				47,212				41,794
Operating income (loss) before taxes			(8,615	)			(9,207	)			(46,724	)			(40,274	)
Non operating income:
Net realized and unrealized gains (losses)			(1,077	)			(179	)			(1,518	)			(905	)
Other income			1,002				159				3,640				2,617
Income (loss) before taxes			(8,690	)			(9,227	)			(44,602	)			(38,562	)
Less: provision (benefit) for income taxes			616				(2,429	)			(5,691	)			(6,217	)
Net income (loss) from continuing operations			(9,306	)			(6,798	)			(38,911	)			(32,345	)
Net income (loss) from discontinued operations (1)			15,183				26,347				73,838				85,712
Net income (loss) attributable to common stockholders		$	5,877			$	19,549			$	34,927			$	53,367
Net income (loss) from continuing operations per common share:
Basic earnings per share		$	(0.25	)		$	(0.18	)		$	(1.04	)		$	(0.88	)
Diluted earnings per share		$	(0.25	)		$	(0.18	)		$	(1.04	)		$	(0.88	)
Net income (loss) from discontinued operations per common share:
Basic earnings per share		$	0.35			$	0.71			$	1.97			$	2.32
Diluted earnings per share		$	0.29			$	0.67			$	1.80			$	2.22
Net income (loss) per common share:
Basic earnings per share		$	0.10			$	0.53			$	0.93			$	1.44
Diluted earnings per share		$	0.04			$	0.49			$	0.76			$	1.34
Weighted average number of common shares:
Basic			37,823,832				37,189,433				37,559,807				36,872,706
Diluted			37,823,832				37,189,433				37,559,807				36,872,706
Dividends declared per common share		$	0.06			$	0.31			$	0.24			$	0.49

(1)See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations for further details, as disclosed in Tiptree's 10-K filing for the period ended December 31, 2025.

Page 4

Tiptree Inc.

Non-GAAP Financial Measures — Book Value per share

Book value is frequently used by the financial community to analyze company growth on a relative per share basis. The following table provides a reconciliation between total stockholders’ equity and total shares outstanding, net of treasury shares.

($ in thousands, except per share information)		As of December 31,
		2025				2024
Total stockholders’ equity		$	752,399			$	656,771
Less: Non-controlling interests			243,848				199,073
Total stockholders’ equity, net of non-controlling interests		$	508,551			$	457,698
Total common shares outstanding			37,824				37,256
Book value per share		$	13.45			$	12.29

Page 5

Company Update March 2026 EXHIBIT 99.2

1 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 AND PROJECTIONS 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 the company’s control, are difficult to predict and could cause actual results to differ materially from those expressed or forecast in the forward-looking statements. 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 the forward-looking statements. Other unknown or unpredictable factors also could affect the forward-looking statements provided. Consequently, actual performance could be materially different from the results described or anticipated by the forward-looking statements. Given these uncertainties, one should not place undue reliance on these forward-looking statements. Except as required by the federal securities laws, Tiptree Inc. undertakes no obligation to update any forward-looking statements. In light of the risks and uncertainties inherent in all projections, the inclusion of forward-looking statements and projections in this presentation should not be considered as a representation by us or any other person that our objectives or plans will be achieved. Numerous factors, including those described in Tiptree’s Annual Report on Form 10‐K or in Tiptree’s other filings with the SEC, could cause our actual results to differ materially from those expressed or implied in forward-looking statements. NOT AN OFFER OR SOLICITATION 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. Disclaimers

2 Recent Announcements All-cash transaction for total consideration of $1.65 billion, with $1.12 billion² in gross proceeds to Tiptree. Valuation of 2.3x BV (3.9x TBV) and 10.7x LTM net income1 Tiptree estimated gross return of 14.2x MOIC and 22.7% IRR, with an anticipated closing in mid-2026. Sale of Fortegra Tiptree's pro-forma book value as of December 31, 2025 is estimated to be $9233 million, net of estimated taxes and transaction expenses for the closing of both transactions. Tiptree will continue to think and act like owners—focused on long-term value creation through strategic investments, opportunistic share buybacks, and thoughtful consideration of dividends. The company continues to streamline operations and manage costs to support sustainable growth. Tiptree Consideration & Long-term Objectives On October 31, 2025, the Company agreed to sell its mortgage business, Reliance First Capital, for 93.5% of tangible book value at closing, or $50 million of estimated gross proceeds as of December 31, 2025. Tiptree estimated gross return of 2.8x MOIC and 13.3% IRR, with an anticipated closing in first half of 2026. Sale of Reliance 1. All multiples are based on Fortegra’s Q2’25 reported financials. 2. Tiptree's fully diluted ownership of Fortegra of 69.1%, presented after estimated deal transaction expenses. 3. Tiptree's pro-forma book value as of December 31, 2025 is estimated to be $923 million, net of estimated taxes and transaction expenses for the closing of both transactions and reflecting Tiptree's fully diluted ownership of Fortegra of 69.1%.

Tiptree at a Glance 3 Michael Barnes, Chairman & Chief Executive Officer 35+ years of investment management & executive leadership experience with Tiptree (18 years), Tricadia Holdings, UBS, PaineWebber, Bear Stearns Randy Maultsby, President 30+ years of investment banking & executive leadership experience with Tiptree (16 years), Fox-Pitt Kelton, Swiss Re, JP Morgan, Citigroup Scott McKinney, Chief Financial Officer 20+ years of executive leadership experience with Tiptree (10 years) & General Electric Overview About Tiptree Founded in 2007 by seasoned management team focused on long-term value creation for shareholders (NASDAQ: TIPT)1 We seek to deliver consistent, risk-adjusted returns through disciplined investing, share repurchases and dividends $2.4 billion of realized investments representing a 2.8x MOIC and 22% IRR since inception2 Flexible Capital Allocation Model Diversified capital allocation strategy provides access to small and mid-sized businesses, while maintaining liquidity and transparency of a public company Strong track record of returning capital to shareholders Aligned and Incentivized Management 34% insider ownership4 deeply aligns Tiptree’s management team with shareholders Significant performance-based incentives focus on excess value creation Leadership Shareholder Total Return (as of December 31, 2025) Tiptree Russell 2000 S&P 500 3 Year 11.8% 13.7% 23.0% 5 Year 32.6% 6.1% 14.4% 10 Year 13.4% 9.6% 14.8% From Jun’073 9.6% 7.6% 10.7% $180mm of capital returned to shareholders through share repurchases, tax-deferred distributions and common dividends 1. Public as of 7/1/2013. 2. Realized Investment represents total realized proceeds including cash distributions and cash or marketable securities received upon realization event. Includes $1.12Bn estimated gross proceeds from the sale of Fortegra presented after deal transaction expenses at Tiptree’s estimated 69.1% ownership on a pro-forma basis, and $50 million of gross proceeds from the sale of Reliance. MOIC and IRR% presented gross before corporate taxes and corporate expenses. 3. Based upon a starting point of Tiptree’s founding in 2007 and book value per share of $5.36. Cumulative dividends paid from 2007 to December 31, 2025, total $3.77 per share. 4. As of 12/31/2025.

18 Years of a Value Creation Strategy 4 ($ in millions) 2007 Tiptree formed as a permanent capital vehicle (June 2007) Strategy Deep expertise in insurance, asset management, specialty finance, infrastructure and real assets We invest in businesses that demonstrate: Proven leadership with talented management teams Established and growing cash flow generation Scalable business models with upside potential Tiptree publicly listed on NASDAQ (TIPT) (July 2013) Value-add Provide support to management teams to unlock the full value potential of their businesses Implement a tailored strategy for each portfolio company Drive strategic growth through acquisitions, business line expansion and key talent recruitment Invest in scalable technology to accelerate business plan Provide capital and access to funding to support growth initiatives

5 Our Performance 1. Realized Investment represents total realized proceeds including cash distributions and cash or marketable securities received upon realization event. Includes $1.12Bn estimated gross proceeds from the sale of Fortegra presented after deal transaction expenses at Tiptree’s estimated 69.1% ownership on a pro-forma basis, and $50 million of gross proceeds from the sale of Reliance. 2. IRR% presented gross before corporate taxes and corporate expenses. IRR represents the internal rate of return on invested capital based on the realized proceeds of cash or marketable securities and including the timing of contributions and distributions. Tiptree’s IRR% calculation reflects the impact of asset specific leverage and may differ from those used by others. Past performance is not indicative of future results. 3. As of 12/31/2025. Insurance & Insurance Services Asset Management Infrastructure & Real Assets Specialty Finance Realized Investments1 IRR%2 $1,375 23% $306 30% $485 9% $227 21% Realized Current + Cash and U.S. Government Securities (including credit investments) $2,393 22% ($ in millions) Proven track record Alignment with key stakeholders An attractive opportunity for prospective targets 33% shareholder return over past 5 years $2.4bn of transaction value across 21 completed and announced transactions Realized investment returns of 22% IRR and 2.8x MOIC over 18-year history 1,2 Founder-led with 34% insider ownership3 Long-term performance-based incentives Proven expertise in disciplined capital deployment Long-term focus, patient capital partner Significant experience supporting management teams unlock the full value potential of their businesses Public company with strategic, capital markets, finance & legal support Sale Agreement Signed on 9/26/2025 Sale Agreement Signed on 10/31/2025

6 ($ in millions) Aligned leadership team focused on compounding shareholder returns over the long-term Think like owners Seek new acquisition opportunities Opportunistic share repurchases Maintain consistent dividends Continued Focus on Long-Term Objectives What comes next Our fundamental objectives Anticipated closing of Reliance and Fortegra transactions by mid-2026 Patiently and actively pursuing new investment opportunities focused on long-term shareholder value creation Focus on operating businesses within our core areas of expertise Tiptree is focused on driving long-term value creation by acquiring controlling interests in resilient, high-quality businesses with strong growth trajectories

Appendix Tiptree - Realized Investment IRR%

8 ($ in millions) All Figures above presented before corporate taxes and corporate expenses. Invested Capital: Represents initial consideration plus additional contributions (if applicable). Realized Investment: Represents total realized proceeds including cash distributions and cash or marketable securities received upon realization event. MOIC: Represents multiple on Invested Capital which is the ratio of Realized Investment to Invested Capital. IRR %: Represents the internal rate of return on invested capital based on the realized proceeds of cash or marketable securities and including the timing of contributions and distributions. Our IRR calculation may differ from those used by others. Past performance is not indicative of future results. 1. Represents invested capital associated with realized investments. Includes $1.12Bn estimated gross proceeds from the sale of Fortegra presented after deal transaction expenses at Tiptree’s estimated 69.1% ownership on a pro-forma basis, and $50 million of gross proceeds from the sale of Reliance. 2. Total Tiptree Inc stockholders’ equity of $508.6mm as of December 31,.2025 includes $(162.9)mm of Tiptree Corporate net liabilities, including $117.9mm of deferred tax liability related to the sale of Fortegra and Reliance. Tiptree - Realized Investment IRR%

ir@tiptreeinc.com

FAQ

What major transactions did Tiptree Inc. (TIPT) highlight in its March 2026 update?

Tiptree highlighted agreements to sell Fortegra and Reliance First Capital. Fortegra is valued at $1.65 billion with about $1.12 billion in estimated gross proceeds to Tiptree, while Reliance is expected to generate roughly $50 million in estimated gross proceeds as of December 31, 2025.

How will the Fortegra and Reliance sales affect Tiptree’s pro-forma book value?

The company estimates that, after both transactions and related taxes and expenses, pro-forma book value will be about $923 million, or roughly $24.40 per share as of December 31, 2025. This estimate reflects Tiptree’s fully diluted ownership position in Fortegra.

What were Tiptree Inc. (TIPT) earnings per share for 2025?

For 2025, Tiptree reported diluted earnings per share of $0.76, compared with $1.34 in 2024. Continuing operations were loss-making, while discontinued operations, including Fortegra and Reliance, generated positive net income that drove overall profitability.

How did Tiptree’s book value per share change in 2025?

Tiptree’s book value per share increased from $12.29 to $13.45 as of December 31, 2025. This growth reflects higher total stockholders’ equity of about $752.4 million, including both Tiptree stockholders and non-controlling interests, relative to the prior year.

What dividend did Tiptree Inc. (TIPT) declare in its March 2026 release?

The board declared a cash dividend of $0.06 per common share. Stockholders of record on March 16, 2026 will receive payment on March 23, 2026, continuing Tiptree’s practice of combining dividends with other capital allocation tools.

How much net income did Tiptree generate from discontinued operations in 2025?

In 2025, Tiptree reported net income from discontinued operations of about $73.8 million, compared with roughly $85.7 million in 2024. These discontinued operations, which include Fortegra and Reliance, provided the bulk of total net income attributable to common stockholders.

What does Tiptree’s management say about its long-term strategy after these sales?

Management reiterated that Tiptree will continue to “think and act like owners,” focusing on long-term value through strategic investments, opportunistic share buybacks, and thoughtful dividends, while streamlining operations and managing costs to support sustainable growth after the Fortegra and Reliance transactions.

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