Company: TIPT
Filing Date: 2025-11-25
Form Type: DEFA14A
Source: 0001140361-25-043224
Chunk: 4

Company: TIPTREE INC.
Filing Date: 2025-11-25
Form: DEFA14A
Chunk 4
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 Group LLC |     |             $400 |     | 4.55x |     | N/A   |     | N/A        |
| 1/15/2021  | TowerBrook Capital Partners L.P. & Further Global Capital Management | ProSight Global, Inc.          |     |             $586 |     | 0.96x |     | 1.01x |     | 8.6x       |
| 8/22/2018  | The Hartford Financial Services Group, Inc.                          | The Navigators Group, Inc.     |     |           $2,151 |     | 1.74x |     | 1.78x |     | 20.6x      |

| • | Date Announced:3/19/2025Buyer:The Doctor’s CompanyTarget:ProAssurance Corporation |

| • | Date Announced:12/16/2022Buyer:Altaris, LLCTarget:Trean Insurance Group, Inc. |

| • | Date Announced:8/10/2022Buyer:Mitsui Sumitomo Insurance 
 Co. Ltd.Target:Transverse Insurance Group LLC           |

| • | Date Announced:1/15/2021Buyer:TowerBrook Capital Partners            
 L.P. & Further Global Capital ManagementTarget:ProSight Global, Inc. |

| • | Date Announced:8/22/2018Buyer:The Hartford Financial  
 Services Group, Inc.Target:The Navigators Group, Inc. |

Commercial:

| Date      
 Announced | Buyer                                                                                         | Target                                     |     | Deal Value ($mm) |     | P/BV  |     | P/TBV |     | Forward    
 Year 2 P/E |
| 8/27/2025 | Sompo Holdings, Inc.                                                                          | Aspen                                      |     |           $3,480 |     | 1.30x |     | 1.31x |     | 7.4x       |
| 7/29/2024 | Affiliates of Sixth Street Partners, LLC                                                      | Enstar Group Limited                       |     |           $5,148 |     | 0.98x |     | 0.99x |     | N/A        |
| 4/5/2024  | Arch Insurance North America                                                                  | Fireman’s Fund Insurance Company (Allianz) |     |           $1,850 |