X0306 4 2017-02-28 0 0001393726 TIPTREE INC. TIPT 0001499150 Ilany Jonathan C/O TIPTREE INC. 780 THIRD AVENUE, 21ST FLOOR NEW YORK NY 10017 1 1 0 0 Chief Executive Officer Employee Stock Option 6.65 2017-02-28 4 A 0 351155 0.00 A Class A Common Stock 351155 501897 D The Reporting Person was granted non-qualified stock options to purchase 351,155 shares of common stock of the Registrant, subject to the terms of a Stock Option Agreement between the Registrant and the Reporting person (the "Stock Option Agreement"). Exercise of the Stock Option is subject to both (1) a time-based vesting requirement with one-third vesting each of February 22, 2020, 2021 and 2022 and (2) a performance-based vesting requirement that, at any time during the option term, achievement of a 20-day volume weighted average stock price of Registrant's Class A Common Stock, that exceeds the per share book value on an as exchanged basis as of December 31, 2016 (as reported in the Registrant's filings with the Securities and Exchange Commission). The Stock Option will expire on the earlier of (1) February 22, 2027 and (2) the date of the termination of Jonathan Ilany's service with the Registrant for Cause (as defined in the Stock Option Agreement) or Jonathan Ilany's voluntary termination of service with the Registrant. /s/ Neil C. Rifkind as Attorney-in-Fact for Jonathan Ilany 2017-03-02