Form 8-K

8-K — TIPTREE INC.

Accession: 0001393726-26-000025

Filed: 2026-04-30

Period: 2026-04-28

CIK: 0001393726

SIC: 6331 (FIRE, MARINE & CASUALTY INSURANCE)

Item: Entry into a Material Definitive Agreement

Item: Results of Operations and Financial Condition

Item: Regulation FD Disclosure

Item: Financial Statements and Exhibits

Documents

8-K — tipt-20260428.htm (Primary)

EX-2.1 (tipt-ex2_1.htm)

EX-99.1 (tipt-ex99_1.htm)

EX-99.2 (tipt-ex99_2.htm)

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8-K

8-K (Primary)

Filename: tipt-20260428.htm · Sequence: 1

8-K

0001393726false00013937262026-04-282026-04-28

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): April 28, 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 1.01 Entry into a Material Definitive Agreement.

On April 28, 2026, Tiptree Inc., a Maryland corporation (“Tiptree” or the “Company”), The Fortegra Group, Inc., a Delaware corporation and subsidiary of the Company (“Fortegra”), DB Insurance Co., Ltd., incorporated and existing under the laws of the Republic of Korea (“Purchaser”), and DB Insurance North America Merger Sub, Inc., a Delaware corporation and wholly owned subsidiary of Purchaser (“Merger Sub”), entered into that certain First Amendment to Agreement and Plan of Merger (the “Amendment”), which amends the Agreement and Plan of Merger, dated as of September 26, 2025 (as amended, the “Merger Agreement”), by and among the Company, Fortegra, Purchaser and Merger Sub. The Merger Agreement provides for, among other things, the acquisition of Fortegra by Purchaser, by means of a merger of Merger Sub with and into Fortegra, with Fortegra surviving the merger as a wholly owned subsidiary of Purchaser (the “Transaction”).

As a result of the Amendment, the Transaction will no longer be conditioned on the approval and/or non-disapproval from the New York State Department of Financial Services (the “NYDFS”) of the proposed acquisition of control of South Bay Acceptance Corp. (“SBAC”), a wholly owned subsidiary of Fortegra, which holds a premium finance agency license in New York. In lieu of the foregoing condition, Fortegra has agreed to use its reasonable best efforts to cause SBAC to surrender its premium finance agency license issued by the NYDFS by no later than May 5, 2026 as a condition to the closing of the Transaction.

Except as amended by the Amendment, the Merger Agreement continues in full force and effect.

The foregoing description of the Amendment does not purport to be complete and is qualified in its entirety by reference to the full text of the Amendment, which is filed as Exhibit 2.1 hereto and incorporated herein by reference.

Item 2.02 Results of Operations and Financial Condition.

On April 30, 2026 Tiptree issued a press release announcing its results of operations for the three months ended March 31, 2026. 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 May 18, 2026 and a payment date of May 26, 2026.

On April 30, 2026, the Company posted an investor presentation dated April 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

2.1

First Amendment to Agreement and Plan of Merger, dated as of April 28, 2026, by and among DB Insurance Co., Ltd., DB Insurance North America Merger Sub, Inc., The Fortegra Group, Inc. and Tiptree Inc.

99.1

Tiptree Inc. press release, dated April 30, 2026.

99.2

Tiptree Inc. Investor Presentation - April 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:

April 30, 2026

By:

/s/ Michael G. Barnes

Name:

Michael G. Barnes

Title:

Chairman and Chief Executive Officer

EX-2.1

Filename: tipt-ex2_1.htm · Sequence: 2

EX-2.1

EXHIBIT 2.1

FIRST AMENDMENT

AGREEMENT AND PLAN OF MERGER

THIS FIRST AMENDMENT TO AGREEMENT AND PLAN OF MERGER (this “Amendment”), dated as of April 28, 2026, is made and entered into by and among DB Insurance Co., Ltd., incorporated and existing under the laws of the Republic of Korea with its registered office at DB Financial Center, 432, Teheran-ro, Gangnam-gu, Seoul, Korea, 06194 (“Purchaser”), DB Insurance North America Merger Sub, Inc., a Delaware corporation and a wholly owned subsidiary of Purchaser (“Merger Sub”), The Fortegra Group, Inc., a Delaware corporation (“Company”) and Tiptree Inc., a Maryland corporation (“Company Parent”).

WHEREAS, Purchaser, the Company and Company Parent entered into that certain Agreement and Plan of Merger (the “Merger Agreement”), dated as of September 26, 2025 (as amended by this Amendment, the “Agreement”);

WHEREAS, Merger Sub has been duly formed and has executed and delivered a joinder to the Merger Agreement in accordance with Section 7.12(b) thereof (the “Merger Sub Joinder”), and the Merger Sub Joinder remains in full force and effect; and

WHEREAS, the parties desire to amend the Merger Agreement as set forth herein in accordance with Section 11.02 of the Merger Agreement.

NOW, THEREFORE, in consideration of the mutual covenants and agreements set forth in this Amendment, and for other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, the parties do hereby agree as follows:

ARTICLE I AMENDMENTS

Section 1.1 Amendments to the Merger Agreement.

(a)

Section 1.1 of the Merger Agreement is hereby amended and restated to include the following:

“DFS” shall have the meaning set forth in Section 7.20 hereof.

“Premium Finance License” shall have the meaning set forth in Section 7.20 hereof.

“SBAC” shall mean South Bay Acceptance Corp., a subsidiary of the Company.

(b)

Article VII of the Merger Agreement is hereby amended to include the following as a new Section 7.20:

Section 7.20 License Surrender. The Company shall use its reasonable best efforts to cause SBAC to take all actions necessary to surrender its premium finance agency license (the “Premium Finance License”) issued by the New York State Department of Financial Services (the “DFS”), including: (i) delivering a notice of surrender of the Premium Finance License to DFS, including through the Nationwide Multistate Licensing System, (ii) disposing of any New York loan receivables under the Premium Finance License, including

delivering loan forgiveness waiver letters to all borrowers of SBAC such that no loans remain outstanding, (iii) returning to DFS all original licenses and riders issued by DFS, and (iv) promptly submitting any additional filings, notifications and submissions requested by the DFS in connection therewith, each of (i), (ii), and (iii) to be completed by no later than May 5, 2026. The Company shall keep Purchaser reasonably informed of the status of such surrender and cooperate with the Purchaser in connection therewith pursuant to Section 7.02 of this Agreement. The Company will deliver to Purchaser at the Closing evidence reasonably satisfactory to Purchaser of the actions taken pursuant to this Section 7.20.

For the avoidance of doubt, no action taken by the Company or SBAC in compliance with and furtherance of this Section 7.20 shall constitute (i) a breach of any representation, warranty, covenant or agreement of the Company or Company Parent under this Agreement or (ii) a failure of any condition set forth in Article VIII of this Agreement.

(c)

Section 8.02 of the Merger Agreement is hereby amended to include the following as a new clause (e):

(e) Premium Finance License Surrender. The Premium Finance License held by SBAC shall have been surrendered and all actions necessary to effect such surrender as set forth in clauses (i), (ii) and (iii) of Section 7.20 shall have been taken.

(d)

Schedule 8.01(d)(i) of the Merger Agreement is hereby amended to remove the following approval from a Governmental Authority from such Schedule (the “Regulatory Approval”):

16. Approval and/or non-disapproval from the New York Department of Financial Services, through the Nationwide Multistate Licensing System, pursuant to N.Y. Banking Law § 555-a, in connection with the proposed acquisition of control of South Bay Acceptance Corp., which holds a premium finance license in New York.

Any references to such Regulatory Approval in the Merger Agreement shall be deemed deleted in their entirety. For the avoidance of doubt, the above-mentioned Regulatory Approval removed from Schedule 8.01(d)(i) shall no longer be required as a condition to the Closing pursuant to Section 8.01(d) of the Merger Agreement and the failure to obtain such Regulatory Approval and the surrender of the Premium Finance License shall not constitute a breach of any representation, warranty, covenant or agreement contained in the Agreement or failure to fulfill any condition to the Closing set forth therein.

ARTICLE II GENERAL PROVISIONS

Section 2.1 Defined Terms. Except as otherwise set forth in this Amendment, all capitalized terms used and not defined herein shall have the meanings given to such terms in the Merger Agreement.

Section 2.2 Effect of Amendment. Each party to this Amendment represents that it has all necessary power and authority to enter into and perform the obligations of this Amendment and that there are no consents or approvals required to be obtained by such party for such party to enter into and perform its obligations under this Amendment that have not been obtained. This Amendment shall be deemed incorporated into, and form a part of, the Merger Agreement and have the same legal validity and effect as the Merger Agreement. This Amendment shall be effective as of the date first written above. After giving effect to this Amendment, unless the context otherwise requires, each reference in the Merger Agreement or any Exhibit or Schedule thereto to “this Agreement”, “the Agreement”, “hereof”, “herein” or words of like import referring to the Merger Agreement shall refer to the Merger Agreement as amended by this Amendment (except that references in the Merger Agreement to the “date hereof” or “date of this

Agreement” or words of similar import shall continue to mean September 26, 2025). Except as amended by this Amendment, the Merger Agreement will continue in full force and effect and shall be otherwise unaffected hereby.

Section 2.3 General Provisions. This Amendment hereby incorporates the provisions of Article XI of the Merger Agreement as if fully set forth herein, mutatis mutandis.

[Signature pages follow]

IN WITNESS WHEREOF, each of the parties has caused this Amendment to be duly executed on its behalf as of the day and year first above written.

THE COMPANY:

THE FORTEGRA GROUP, INC.

By: /s/ Richard Kahlbaugh

Name: Richard Kahlbaugh

Title: President and CEO

PURCHASER:

DB INSURANCE CO., LTD.

By: /s/ Jong Pyo Jeong

Name: Jong Pyo Jeong

Title: Chief Executive Officer

MERGER SUB:

DB INSURANCE NORTH AMERICA MERGER SUB, INC.

By: /s/ Ki Hyun Park

Name: Ki Hyun Park

Title: Director

COMPANY PARENT:

TIPTREE INC.

By: /s/ Michael G. Barnes

Name: Michael G. Barnes

Title: Chairman and Chief Executive Officer

[Signature Page - First Amendment to Agreement and Plan of Merger]

EX-99.1

Filename: tipt-ex99_1.htm · Sequence: 3

EX-99.1

Exhibit 99.1

TIPTREE ANNOUNCES FIRST QUARTER 2026 RESULTS

Greenwich, Connecticut – April 30, 2026- Tiptree Inc. (NASDAQ:TIPT) (“Tiptree” or the “Company”), today announced its financial results for the three months ended March 31, 2026.

Highlights

•

Returned capital to shareholders through approximately $5.0 million of share repurchases during the first quarter, at an average price of $16.13 per share.

•

Declared a dividend of $0.06 per share to stockholders of record on May 18, 2026 with a payment date of May 26, 2026.

•

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 remains 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 March 31, 2026. Anticipated closing remains mid-2026.

•

Tiptree's pro-forma book value as of March 31, 2026 is estimated to be $912 million or $23.80 per diluted share, 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. 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 March 31,

GAAP:

2026

2025

Total revenues

—

390

Total expenses

8,997

12,972

Income (loss) before taxes

(8,292

)

(11,306

)

Net income (loss) from continuing operations

(7,139

)

(9,701

)

Net income (loss) from discontinued operations

21,385

15,336

Diluted earnings per share

0.34

0.13

Cash dividends paid per common share

0.06

Non-GAAP(1):

Book value per share

13.42

12.63

(1) 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 (Unaudited)

($ in thousands, except share data)

As of

March 31, 2026

December 31, 2025

Assets:

Current assets:

Cash and cash equivalents

33,401

30,784

Marketable securities

581

21,701

Other current assets

2,270

2,361

Total current assets

36,252

54,846

Right of use asset

7,837

8,301

Property, plant and equipment, net

5,906

6,262

Other assets

2,739

2,269

Assets held for sale (1)

6,914,921

6,768,387

Total assets

6,967,655

6,840,065

Liabilities and Stockholders’ Equity

Liabilities:

Current liabilities:

Short-term debt, net

7,979

8,138

Other current liabilities

19,948

20,964

Total current liabilities

27,927

29,102

Long-term debt, net

64,126

63,948

Long-term lease obligations

8,139

8,654

Deferred tax liabilities

82,686

80,390

Liabilities held for sale (1)

6,034,281

5,905,572

Total liabilities

6,217,159

6,087,666

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, 37,567,024 and 37,824,472 shares issued and outstanding, respectively

Additional paid-in capital

390,416

394,435

Accumulated other comprehensive income (loss), net of tax

(19,727

)

(7,496

)

Retained earnings

133,552

121,574

Total Tiptree Inc. stockholders’ equity

504,279

508,551

Non-controlling interests:

Fortegra preferred interests

77,679

Common interests

168,538

166,169

Total non-controlling interests

246,217

243,848

Total stockholders’ equity

750,496

752,399

Total liabilities and stockholders’ equity

6,967,655

6,840,065

(1)

See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations for further details, as disclosed in Tiptree's 10-Q filing for the period ended March 31, 2026.

Page 3

Tiptree Inc.

Condensed Consolidated Statements of Operations (Unaudited)

($ in thousands, except share data)

Three Months Ended March 31,

2026

2025

Revenues:

Other revenue

—

390

Total revenues

—

390

Expenses:

Employee compensation and benefits

6,762

9,333

Depreciation and amortization

356

357

Other expenses

1,879

3,282

Total expenses

8,997

12,972

Operating income (loss) before taxes

(8,997

)

(12,582

)

Non operating income:

Net realized and unrealized gains (losses)

(261

)

740

Other income

966

536

Income (loss) before taxes

(8,292

)

(11,306

)

Less: provision (benefit) for income taxes

(1,153

)

(1,605

)

Net income (loss) from continuing operations

(7,139

)

(9,701

)

Net income (loss) from discontinued operations (1)

21,385

15,336

Net income (loss) attributable to common stockholders

14,246

5,635

Net income (loss) from continuing operations per common share:

Basic earnings per share

(0.19

)

(0.26

)

Diluted earnings per share

(0.19

)

(0.26

)

Net income (loss) from discontinued operations per common share:

Basic earnings per share

0.57

0.41

Diluted earnings per share

0.53

0.39

Net income (loss) per common share:

Basic earnings per share

0.38

0.15

Diluted earnings per share

0.34

0.13

Weighted average number of common shares:

Basic

37,789,444

37,348,219

Diluted

37,789,444

37,348,219

Dividends declared per common share

0.06

(1)

See Note (3) Dispositions, Assets Held for Sale & Discontinued Operations for further details, as disclosed in Tiptree's 10-Q filing for the period ended March 31, 2026.

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)

Three Months Ended March 31,

2026

2025

Total stockholders’ equity

750,496

683,462

Less: Non-controlling interests

246,217

209,743

Total stockholders’ equity, net of non-controlling interests

504,279

473,719

Total common shares outstanding

37,567

37,494

Book value per share

13.42

12.63

Page 5

EX-99.2

Filename: tipt-ex99_2.htm · Sequence: 4

Company Update April 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 14.1x MOIC and 22.6% IRR, with an anticipated closing in mid-2026. Sale of Fortegra Tiptree's pro-forma book value as of March 31, 2026 is estimated to be $912 million or $23.803 per share on a diluted basis, 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 March 31, 2026. Tiptree estimated gross return of 2.9x MOIC and 13.3% IRR, with an anticipated closing in mid-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 69.0%, presented after estimated deal transaction expenses. 3. Tiptree's pro-forma book value as of March 31, 2026 is estimated to be $912 million or $23.80 per share on a fully diluted basis, net of estimated taxes and transaction expenses for the closing of both transactions and reflecting Tiptree's fully diluted ownership of Fortegra of 69.0%. Diluted shares as of March 31, 2026, represents basic outstanding shares of 37,567,024 plus dilutive shares of 737,607 which includes unvested RSUs and outstanding options (assumed to be exercised cashless).

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 March 31, 2026) Tiptree Russell 2000 S&P 500 3 Year 7.2% 13.0% 18.3% 5 Year 15.8% 3.8% 12.1% 10 Year 13.5% 9.9% 14.2% From Jun’073 9.1% 7.6% 10.3% $187mm 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 69.0% 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 March 31, 2026, total $3.83 per share. 4. As of 4/22/2026.

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 69.0% 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 4/22/2026. Insurance & Insurance Services Asset Management Infrastructure & Real Assets Specialty Finance Realized Investments1 IRR%2 $1,375 23% $306 30% $489 9% $227 21% Realized Current + Cash and U.S. Government Securities (including credit investments) $2,397 22% ($ in millions) Proven track record Alignment with key stakeholders An attractive opportunity for prospective targets 16% 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 69.0% ownership on a pro-forma basis, and $50 million of gross proceeds from the sale of Reliance. 2. Total Tiptree Inc stockholders’ equity of $504.3mm as of March 31, 2026 includes $(164.1)mm of Tiptree Corporate net liabilities, including $122.0mm of deferred tax liability related to the sale of Fortegra and Reliance. Tiptree - Realized Investment IRR%

ir@tiptreeinc.com

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