Company: TIPT
Filing Date: 2025-10-17
Form Type: PREM14A
Source: 0001140361-25-038514
Chunk: 318

Company: TIPTREE INC.
Filing Date: 2025-10-17
Form: PREM14A
Chunk 318
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 (“2022 PRSUs”), subject to vesting upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the 30 trading day closing stock price, ranging from $30 to $60 (adjusted for dividends paid) and (c) 137,500 PRSUs granted on January 1, 2024 (“2024 PRSUs”), subject to vesting upon Tiptree achieving a Tiptree share price target milestone, based on the average of the 30 trading day closing stock price of $70 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant. Any unvested 2022 PRSUs will expire on August 4, 2031. Any unvested 2024 PRSUs will expire on January 1, 2034. All of (a) - (c) above are subject to Mr. McKinney’s continued employment with Tiptree. |

| (8) | Excludes (a) 22,664 RSUs, which were granted on February 22, 2023 and will cliff vest on February 20, 2026 and (b) 23,792 RSUs, which were granted on February 27, 2024 and will cliff vest on February 20, 2027 and (c) 22,246 RSUs, which were granted on February 25, 2025 and will cliff vest on February 28, 2028, all of (a) - (c) are subject to Mr. Rifkind’s continued employment with Tiptree. |

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#### TABLE OF CONTENTS

### MARKET PRICES AND DIVIDEND DATA
Shares of Tiptree common stock are listed on Nasdaq under the symbol “TIPT”. As of the record date for the special meeting, there were [ ] shares of Tiptree common stock outstanding held by approximately [ ] holders of record. The actual number of holders of shares of Tiptree common stock is greater than this number of record holders and includes holders of shares of Tiptree common stock who are beneficial owners, but whose shares of Tiptree common stock are held in street name by brokers and other nominees. The Tiptree Board is responsible for determining our dividend policy. The timing and level of any dividends will necessarily depend on the Tiptree Board’s assessments of earnings, financial condition, capital requirements and other factors, including restrictions, if any, imposed by our