Tiptree Inc SEC Filings

Dimensional Fund Advisors LP reported beneficial ownership of 2,175,071 shares of Tiptree Inc common stock, representing 5.8% of the class as of 09/30/2025. The filing is a Schedule 13G/A, indicating a passive investment position; Dimensional disclaims beneficial ownership and states the shares are held by various managed Funds for which it provides advisory services. The filing shows 2,136,743 shares with sole voting power and 2,175,071 shares with sole dispositive power. The signature block is by the Global Chief Compliance Officer on 10/09/2025.

TIPTREE INC. (TIPT) director Paul M. Friedman received 1,807 shares as the stock portion of his quarterly director retainer on 10/03/2025, issued at no cash cost. After the issuance, Mr. Friedman beneficially owns 120,350 shares, held indirectly through The Paul M. Friedman Living Trust dated 3/5/2019, of which he and his spouse are trustees. The filing notes the share payment is a routine director compensation payment deposited to the trust at the director's request. The Form 4 was signed by an attorney-in-fact on 10/06/2025.

Lesley Goldwasser, a director of TIPTREE INC. (TIPT), reported an acquisition of 1,807 shares of common stock on 10/03/2025 as the stock component of the director's quarterly-paid annual retainer. The transaction shows a price of $0, indicating these shares were issued as compensation rather than purchased. After the grant, the reporting person beneficially owns 112,362 shares. The Form 4 was signed by an attorney-in-fact on 10/06/2025.

Michael Barnes reports beneficial ownership of 10,439,197 shares of Tiptree Inc., equal to 27.35% of the outstanding common stock (including 353,769 shares issuable upon exercise of options). On September 26, 2025, Tiptree entered into a merger agreement under which a Purchaser (DB Insurance Co., Ltd.) will acquire The Fortegra Group, Inc. and related transactions are conditioned on stockholder approval. Mr. Barnes signed a Voting and Support Agreement committing his covered shares to be present and voted in favor of the Merger, to vote against competing proposals, and not to transfer covered shares except under permitted exceptions. The agreement terminates on specified events including closing of the Merger.

Schedule 13D filed by Arif Inayatullah reports he beneficially owns 3,392,420 shares of Tiptree Inc., representing 8.97% of the 37,820,120 shares outstanding. The filing discloses that on September 26, 2025, Tiptree entered into a merger agreement under which a DB Insurance Co., Ltd. purchaser will cause Fortegra to become a wholly owned subsidiary following a merger. Mr. Inayatullah entered into a Voting and Support Agreement with the purchaser committing his covered shares to vote in favor of the merger, to appear for quorum purposes, to vote against competing acquisition proposals, and to refrain from transferring covered shares except as permitted. The Voting Agreement terminates on specified events including closing of the merger.

Tiptree Inc. disclosed a definitive merger agreement where Purchaser will become Fortegra's sole stockholder and the agreed purchase price is $1.65 billion. As of September 26, 2025, Tiptree owns approximately 69.1% of Fortegra on a fully diluted basis. The price will be reduced for certain post-June 30, 2025 payments made before closing ("Leakage"), while specified items are carved out as "Permitted Leakage". Purchaser's recovery for unadjusted Leakage is limited to a leakage reserve holdback account. If closing does not occur on or before June 1, 2026, the $1.65 billion price will accrue a 10% per annum profit-sharing fee from June 1, 2026 until closing. Tiptree signing stockholders have entered into voting agreements with Purchaser regarding Tiptree common shares, and Tiptree will mail a definitive proxy statement regarding the merger.

Jonathan Ilany, Chief Executive Officer and Director of Tiptree Inc. (TIPT), executed a cashless exercise of 351,155 stock options on 09/15/2025. The options had an exercise price of $6.65 and the company’s closing stock price that day was $23.70. The filing reports 98,531 shares withheld to fund the exercise and 124,787 shares withheld to satisfy withholding tax, resulting in the Reporting Person holding 274,742 shares directly and 192,021 shares indirectly (401K) after the transactions. The exercise relates to options originally granted on 02/22/2017 and fully vested by 02/22/2022.

Jonathan Ilany, CEO and Director of Tiptree Inc. (TIPT), reported multiple option exercises on 09/02/2025 resulting in net increases and decreases in his common stock holdings as shown on the Form 4. The filing shows cashless exercises of 137,038 options at a $5.67 exercise price and 13,704 options at a $5.87 exercise price. Portions of the shares issuable on exercise were withheld to fund the cashless transactions and to satisfy tax withholding: 33,262 shares withheld related to the $5.67 options, 3,444 shares withheld related to the $5.87 options, and 53,128 shares withheld for taxes.

After these transactions the reported beneficial ownership positions following each line are: 223,035; 189,773; 203,477; 200,033; and 146,905 shares, with 192,021 shares held indirectly via a 401(k) account. The Form 4 is signed by an attorney-in-fact and includes explanations that the option grants date to 2016 and that the options were fully vested by 2021 and 2026 respectively.