Company: TIPT
Filing Date: 2025-11-25
Form Type: DEFA14A
Source: 0001140361-25-043224
Chunk: 0

Company: TIPTREE INC.
Filing Date: 2025-11-25
Form: DEFA14A
Chunk 0
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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 |

SUPPLEMENT TO PROXY STATEMENT FOR THE SPECIAL MEETING OF STOCKHOLDERS TO BE HELD ON DECEMBER 3, 2025 November 25, 2025 Explanatory Note As previously announced, on September 26, 2025, Tiptree Inc., a Maryland corporation (“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 of Purchaser (“Merger Sub”) to be incorporated in Delaware following the date of the Merger Agreement and prior to the closing of the merger will, upon its formation, execute a joinder to the Merger Agreement and thereby become a party thereto. Pursuant to the Merger Agreement, Merger Sub will be merged with and into Fortegra, the separate corporate existence of Merger Sub will cease and Fortegra will continue as the surviving corporation and a wholly-owned subsidiary of Purchaser (the “Merger”).