Company: TIPT
Filing Date: 2025-10-17
Form Type: PREM14A
Source: 0001140361-25-038514
Chunk: 7

Company: TIPTREE INC.
Filing Date: 2025-10-17
Form: PREM14A
Chunk 7
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 and the consummation of the Merger and the other transactions contemplated by the Merger Agreement; (iii) directed that the Merger and the other transactions contemplated by the Merger Agreement be submitted for consideration at a meeting of Tiptree’s stockholders; and (iv) resolved to recommend that the stockholders of Tiptree approve the Merger and the other transactions contemplated by the Merger Agreement.

We encourage you to read the accompanying proxy statement, including all documents incorporated by reference into the accompanying proxy statement, and annexes to the accompanying proxy statement, carefully and in their entirety. If you have any questions concerning the Merger, the special meeting or the accompanying proxy statement, would like additional copies of the accompanying proxy statement or need help voting your shares of Tiptree common stock, please contact our proxy solicitor:

<div align='center'>Sodali & Co

Call Toll Free: (800) 662-5200</div>

**The Tiptree Board recommends that Tiptree stockholders vote (i) “FOR” the Merger Proposal and (ii) “FOR” the proposal to approve one or more adjournments of the special meeting, if necessary, to solicit additional proxies, in the event that there are insufficient votes to approve the Merger Proposal.**

By Order of the Board of Directors,

Jonathan Ilany

Chief Executive Officer

Dated: [ ], 2025

TABLE OF CONTENTS

TABLE OF CONTENTS

|                                                                              |     | Page |
| SUMMARY                                                                      |     |    1 |
| The Merger                                                                   |     |    1 |
| General Description of the Merger                                            |     |    1 |
| Parties Involved in the Merger                                               |     |    2 |
| Certain Effects of the Merger on Tiptree                                     |     |    2 |
| Effect on Tiptree if the Merger is Not Completed                             |     |    2 |
| Opinion of Barclays Capital Inc. (“Barclays”)                                |     |    7 |
| Interests of Tiptree’s Directors and Executive Officers in the Merger        |     |    8 |
| The Special Meeting                                                          |     |    8 |
| No Appraisal Rights                                                          |     |   10 |
| Risk Factors                                                                 |     |   10 |
| The Merger Agreement                                                         |     |   11 |
| Regulatory Approvals Required for the Merger and Efforts to Close the Merger |     |