Company: TIPT
Filing Date: 2025-11-10
Form Type: PX14A6G
Source: 0001193125-25-274552
Chunk: 3

Company: TIPTREE INC.
Filing Date: 2025-11-10
Form: PX14A6G
Chunk 3
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en a decline in value of non-Insurance 
 assets from $247 million in Q4 2021 to $92 million in Q2 2025.7     |

Shareholders should also be aware that this management, with its mixed track record of investing success, may be motivated to find a new investment quickly, rather than deliberately. As structured, the Proposed Transaction could increase Tiptree’s regulatory burden if an acquisition is not found within a specific period of time, requiring additional compliance with the Investment Company Act of 1940.

| 3 | $28.75 per share value = gross proceeds to Tiptree after deal expenses of $1.12bn as estimated by Tiptree in                                                           
 the Merger Proxy (subject to adjustment) / (37.8mm shares outstanding + 0.2mm unvested RSUs + 0.9mm options, in each case, as reported by Tiptree in its Q3 2025 10Q). |

| 4 | $1.91 per share value = ($55.9mm equity value Mortgage + $68.9mm equity value Other + ($159.6)mm equity value                                                                         
 corporate +$109.2mm Deferred tax liability at Fortegra) / (37.8mm shares outstanding + 0.2mm unvested RSUs + 0.9mm options, in each case, as reported by Tiptree in its Q3 2025 10Q). |

| 5 | Trading price as of market close on November 7, 2025. Excludes regular minimal cash dividend of $0.06 per 
 share in 2025.                                                                                            |

| 6 | 5% of company value includes Named Executive Officer Compensation from the annual Proxy Statement + Related                                                                                                                                     
 Party payments for managing Fortegra investments divided by Tiptree’s market capitalization as measured on the first trading day of each year from 2019 to 2024. For example, in 2024 Named Executive Officers collectively received $24.6mm in 
 compensation per the Proxy filled March 7th, 2025. $24.6mm / (36.7mm outstanding shares per Form 10-K filed on February 29, 2024 * $18.73 closing price                                                                                         
 on first trading day of 2024) = 3.6% of Tiptree 2024 beginning market cap.                                                                                                                                                                      |

| 7 | $247mm = $187