Company: TIPT
Filing Date: 2025-11-25
Form Type: DEFA14A
Source: 0001140361-25-043224
Chunk: 3

Company: TIPTREE INC.
Filing Date: 2025-11-25
Form: DEFA14A
Chunk 3
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| High                                    |     | 5.80x           |     | 5.81x  |     | 20.8x    |

| (1) | Aspen market data as of August 19, 2025, reflecting unaffected data prior to news leak about Aspen’s acquisition by Sompo. |

| • | Under “Selected Precedent Transaction Analysis” on page 59, replace the                          
 paragraph starting with “The reasons for” and the bulleted lists that follow with the following: |

The reasons for and the circumstances surrounding each of the selected precedent transactions analyzed were diverse and there are inherent differences in the business, operations, financial conditions and prospects of Fortegra and the companies included in the selected precedent transaction analysis. Accordingly, Barclays believed that a purely quantitative selected precedent transaction analysis would not be particularly meaningful in the context of considering the Merger. Barclays therefore made qualitative judgments concerning differences between the characteristics of the selected precedent transactions and the Merger which would affect the acquisition values of the selected target companies and Fortegra. Based upon these judgments, Barclays selected (1) a P/BV multiple range of 1.20x to 2.20x, (2) a P/TBV multiple range of 1.20x to 2.20x and (3) a Non-GAAP P/E ‘26E multiple range of 9.0x to 11.0x, and applied such ranges to the Fortegra Projections to calculate a range of implied values of Fortegra. The following table sets tables setforth the transactions analyzed based on such characteristics and the results of such analysis: Pure Specialty:

| Date       
 Announced  | Buyer                                                                | Target                         |     | Deal Value ($mm) |     | P/BV  |     | P/TBV |     | Forward    
 Year 2 P/E |
| 3/19/2025  | The Doctor’s Company                                                 | ProAssurance Corporation       |     |           $1,279 |     | 1.06x |     | 1.12x |     | 23.5x      |
| 12/16/2022 | Altaris, LLC                                                         | Trean Insurance Group, Inc.    |     |             $316 |     | 0.78x |     | 1.65x |     | 11.5x      |
| 8/10/2022  | Mitsui Sumitomo Insurance Co. Ltd.                                   | Transverse Insurance