Company: TIPT
Filing Date: 2025-10-31
Form Type: DEFM14A
Source: 0001140361-25-039949
Chunk: 0

Company: TIPTREE INC.
Filing Date: 2025-10-31
Form: DEFM14A
Chunk 0
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TABLE OF CONTENTS

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a Party other than the Registrant☐ Check the appropriate box:

| ☐ | Preliminary Proxy Statement |

| ☐ | Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) |

| ☒ | Definitive Proxy Statement |

| ☐ | Definitive Additional Materials |

| ☐ | Soliciting Material under §240.14a-12 |

| Tiptree Inc.                                                             |
| (Name of Registrant as Specified In Its Charter)                         |
| N/A                                                                      |
| (Name of Person(s) Filing Proxy Statement, if other than the Registrant) |

Payment of Filing Fee (Check the appropriate box):

| ☐ | No fee required. |

| ☒ | Fee paid previously with preliminary materials. |

| ☐ | Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11 |

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<div align='center'>660 Steamboat Road, 2nd Floor

Greenwich, Connecticut 06830</div>

October 31, 2025

Dear Stockholder:

You are invited to attend a special meeting of stockholders of Tiptree Inc., which we refer to as “Tiptree,” to be held exclusively virtually on December 3, 2025, at 4:00 p.m., Eastern Time, which we refer to as the “special meeting.” You may participate in the special meeting via Internet webcast by visiting the following website and following the registration and participation instructions contained therein: www.virtualshareholdermeeting.com/TIPT2025SM. Please have the control number located on your proxy card available.

On September 26, 2025, Tiptree entered into an Agreement and Plan of Merger (the “Merger Agreement”) with The Fortegra Group, Inc., a Delaware corporation (“Fortegra”), and 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”). A subsidiary