Company: TIPT
Filing Date: 2025-11-24
Form Type: DEFA14A
Source: 0001140361-25-043135
Chunk: 0

Company: TIPTREE INC.
Filing Date: 2025-11-24
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 On November 24, 2025, Tiptree Inc. issued the following press release: Institutional Shareholder Services (ISS) Recommend Tiptree Stockholders
Vote “FOR” the Merger of Fortegra and DB Insurance GREENWICH, Conn., November 24, 2025 – (BUSINESS WIRE)– Tiptree Inc. (NASDAQ: TIPT) today announced that Institutional Shareholder Services Inc. (“ISS”), the leading independent proxy advisory firm, hasrecommended that Tiptree stockholders vote “FOR”the approval of the Agreement and Plan of Merger (the “Merger Agreement”) by and among Tiptree, The Fortegra Group, Inc. (“Fortegra”) and DB Insurance Co., Ltd. (“DB”), providing for the acquisition by DB of all of the outstanding stock of Fortegra in an all-cash deal (the “Merger Proposal”). In their recommendation FOR the Merger Proposal, ISS noted 1:

| • | “The sales process itself was competitive and TIPT explored alternative transaction structures including an IPO, an outright sale of TIPT, and buying