Company: TIPT
Filing Date: 2025-10-31
Form Type: DEFM14A
Source: 0001140361-25-039949
Chunk: 7

Company: TIPTREE INC.
Filing Date: 2025-10-31
Form: DEFM14A
Chunk 7
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 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

430 Park Avenue, 14th Floor

New York, New York 10022

Stockholders Call Toll Free: (800) 662-5200

Brokers and Banks may call collect: (203) 658-9400

Email: TIPT@info.sodali.com</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,

/s/ Jonathan Ilany

Jonathan Ilany

Chief Executive Officer

Dated: October 31, 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                                                                 |