Company: TIPT
Filing Date: 2025-11-10
Form Type: PX14A6G
Source: 0001193125-25-274552
Chunk: 2

Company: TIPTREE INC.
Filing Date: 2025-11-10
Form: PX14A6G
Chunk 2
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 reveal that the market expects Tiptree’s leadership to destroy value, literally valuing the Company at less than its cash. We believe that expectation is a reasonable conclusion based on the Tiptree leadership team’s mixed investment track record and history of poor negotiating. The flawed capital allocation that has marked Tiptree in the past persists today, given Tiptree has disclosed it does not expect to distribute any proceeds of the Proposed Transaction to Tiptree shareholders. 2

| 1 | Tiptree’s total value estimated at $30.66 based on the $28.75 per share proceeds to TIPT plus $1.91 per 
 diluted share of non-Fortegra assets. Please refer to analysis below for further details.               |

While Tiptree is receiving $28.75 per diluted share for Fortegra, shareholders’ proceeds are still to-be-determined. 3Tiptree’s non-Fortegraassets, worth approximately $1.91 per diluted share, are either securities or will become cash following the announced sale of their mortgage business in Q1 2026. 4 The businesses that you own through your Tiptree stock, trading at $18.39 based on the last closing price, will be exchanged for more than $30 of cash value – and shareholders will receive none of it. 5The only real beneficiary of the Proposed Transaction is Tiptree’s conflicted management team, who historically have transferred, on average, more than 5% of the Company’s value to themselves each year. 6Shareholders deserve a better outcome. Tiptree management has supported the Proposed Transaction, but we believe their incentives are not aligned with Tiptree shareholders.

| • |     | On average, 4.4% of Tiptree’s market capitalization in each year from 2019 to 2024 was transferred to Named 
 Executive Officers in annual compensation.                                                                  |

| • |     | Total corporate compensation, not attributable to business segments, was 7.2% of Tiptree market capitalization on 
 average in each year from 2019 to 2024.                                                                           |

| • |     | Tiptree management has collected additional payments through a Related Party agreement to manage Fortegra’s                                                                                
 float at what we believe are above market rates. These additional payments have averaged 1.1% of Tiptree market capitalization in each year since the arrangement was implemented in 2020. |

| • |     | Tiptree management has overse