Company: TIPT
Filing Date: 2025-10-31
Form Type: DEFM14A
Source: 0001140361-25-039949
Chunk: 489

Company: TIPTREE INC.
Filing Date: 2025-10-31
Form: DEFM14A
Chunk 489
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i) to each Specified Eligible Common Stockholder, the Per Share Equityholders’ Representative Expense Release Amount multiplied by the number of shares of Common Stock held by such Specified Eligible Common Stockholder immediately prior to the Effective Time, (ii) to each Optionholder, the Per Share Equityholders’ Representative Expense Release Amount multiplied by the number of shares of Common Stock underlying all vested Stock Options held by such Optionholder immediately prior to the Effective Time and (iii) each Equity Award Holder shall promptly deliver to the Equityholders’ Representatives the Per Share Equityholders’ Representative Expense Amount multiplied by the number of shares of Common Stock underlying all RSU Awards held by such Equity Award Holder immediately prior to the Effective Time.

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<div align='center'>A-86</div>

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IN WITNESS WHEREOF, the Company, Company Parent and Purchaser have executed and delivered this Agreement, or caused this Agreement to be executed and delivered by their duly authorized representatives, as of the date first written above.

|        |     | THE COMPANY:             |
|        |     | THE FORTEGRA GROUP, INC. |
| By:    |     | /s/ Richard Kahlbaugh    |
| Name:  |     | Richard Kahlbaugh        |
| Title: |     | President and CEO        |

[Signature Page to Merger Agreement] A-87

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|        |     | PURCHASER:              |
|        |     | DB INSURANCE CO., LTD.  |
| By:    |     | /s/ Jong Pyo Jeong      |
| Name:  |     | Jong Pyo Jeong          |
| Title: |     | Chief Executive Officer |

[Signature Page to Merger Agreement] A-88

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|        |     | COMPANY PARENT:         |
|        |     | TIPTREE INC.            |
| By:    |     | /s/ Jonathan Ilany      |
| Name:  |     | Jonathan Ilany          |
| Title: |     | Chief Executive Officer |

[Signature Page to Merger Agreement] A-89

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Annex B

| 745 Seventh Avenue 
 New York, NY 10019 
 United States      |

CONFIDENTIAL September 26, 2025 Board of Directors The Fortegra Group, Inc. 10751 Deerwood Park Blvd., Suite 200 Jacksonville