Company: TIPT
Filing Date: 2025-10-17
Form Type: PREM14A
Source: 0001140361-25-038514
Chunk: 495

Company: TIPTREE INC.
Filing Date: 2025-10-17
Form: PREM14A
Chunk 495
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 portfolio companies and affiliates in connection with certain mergers and acquisition transactions; (ii) having acted or acting as arranger, bookrunnner and/or lender for Warburg and certain of its portfolio companies and affiliates in connection with the financing for various acquisition transactions; and (iii) having acted or acting as underwriter, initial purchaser and placement agent for various equity and debt offerings undertaking by Warburg and certain of its portfolio companies and affiliates.

Barclays Capital Inc., its subsidiaries and its affiliates engage in a wide range of businesses from investment and commercial banking, lending, asset management and other financial and non-financial services. In the ordinary course of our business, we and our affiliates may actively trade and effect transactions in the equity, debt and/or other securities (and any derivatives thereof) and financial instruments (including loans and other obligations) of the Company, the Company Parent and the Purchaser for our own account and for the accounts of our customers and, accordingly, may at any time hold long or short positions and investments in such securities and financial instruments.

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TABLE OF CONTENTS

Page 3 of 3 This opinion, the issuance of which has been approved by our Fairness Opinion Committee, is for the use and benefit of the Board of Directors of the Company and is rendered to the Board of Directors of the Company in connection with its consideration of the Proposed Transaction. The Board of Directors of the Company is permitted to disclose this opinion to the Board of Directors of the Company Parent, and the Board of Directors of the Company Parent is permitted to rely on this opinion. This opinion is not intended to be and does not constitute a recommendation to any stockholder of the Company or the Company Parent as to how such stockholder should vote with respect to the Proposed Transaction.

| Very truly yours,     |
| BARCLAYS CAPITAL INC. |

B-3

#### TABLE OF CONTENTS

#### Annex C

### VOTING AND SUPPORT AGREEMENT
This VOTING AND SUPPORT AGREEMENT (this “ Agreement ”), dated as of September 26, 2025, is made and entered into by and between 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 ”), and the undersigned stockholder (the “ Stockholder ”) of Tiptree Inc., a Maryland corporation (“ Company