TIPTREE INC. — Director's Dealing 2016

Jan 6, 2016

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: TIPTREE FINANCIAL INC. (TIPT)
CIK: 0001393726
Period of Report: 2016-01-04

Reporting Person: Barnes Michael Gene (Director, Executive Chairman, 10% Owner)

Non-Derivative Transactions

Date	Security	Code	Shares	Price	A/D	Holdings After	Ownership
2016-01-04	Class A Common Stock	P	619	$5.97	Acquired	3307889	Direct
2016-01-04	Class A Common Stock	P	454	$6.10	Acquired	3308343	Direct
2016-01-04	Class A Common Stock	P	272	$6.31	Acquired	3308615	Direct
2016-01-04	Class A Common Stock	P	188	$6.17	Acquired	3308803	Direct
2016-01-04	Class A Common Stock	P	186	$5.67	Acquired	3308989	Direct
2016-01-04	Class A Common Stock	P	172	$6.01	Acquired	3309161	Direct
2016-01-04	Class A Common Stock	P	63	$5.85	Acquired	3309224	Direct
2016-01-04	Class A Common Stock	P	51	$5.89	Acquired	3309275	Direct
2016-01-04	Class A Common Stock	P	46	$6.20	Acquired	3309321	Direct
2016-01-04	Class A Common Stock	P	45	$5.98	Acquired	3309366	Direct
2016-01-04	Class A Common Stock	P	37	$5.72	Acquired	3309403	Direct
2016-01-04	Class A Common Stock	P	33	$6.07	Acquired	3309436	Direct
2016-01-04	Class A Common Stock	P	33	$5.96	Acquired	3309469	Direct
2016-01-04	Class A Common Stock	P	30	$5.77	Acquired	3309499	Direct
2016-01-04	Class A Common Stock	P	27	$5.76	Acquired	3309526	Direct
2016-01-04	Class A Common Stock	P	25	$5.93	Acquired	3309551	Direct
2016-01-04	Class A Common Stock	P	24	$6.02	Acquired	3309575	Direct
2016-01-04	Class A Common Stock	P	24	$6.08	Acquired	3309599	Direct
2016-01-04	Class A Common Stock	P	23	$5.96	Acquired	3309622	Direct
2016-01-04	Class A Common Stock	P	23	$5.71	Acquired	3309645	Direct
2016-01-04	Class A Common Stock	P	21	$6.09	Acquired	3309666	Direct
2016-01-04	Class A Common Stock	P	20	$5.78	Acquired	3309686	Direct
2016-01-04	Class A Common Stock	P	18	$5.70	Acquired	3309704	Direct
2016-01-04	Class A Common Stock	P	18	$5.75	Acquired	3309722	Direct
2016-01-04	Class A Common Stock	P	14	$5.66	Acquired	3309736	Direct
2016-01-04	Class A Common Stock	P	14	$5.95	Acquired	3309750	Direct
2016-01-04	Class A Common Stock	P	13	$5.84	Acquired	3309763	Direct
2016-01-04	Class A Common Stock	P	7	$6.27	Acquired	3309770	Direct
2016-01-04	Class A Common Stock	A	45679	$0.00	Acquired	45679	Indirect

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2016-01-04	Employee Stock Option	$5.67	A	91359	Acquired		Class A Common Stock (91359)	Indirect

Footnotes

F1: Purchases pursuant to a Rule 10b5-1 trading plan.

F2: The reporting person is a principal of Tricadia Holdings, L.P. ("Tricadia"). The number of shares reflects a total which is greater than the Reporting Person's pecuniary interest. The Reporting Person disclaims beneficial ownership of the reported securities except to the extent of his pecuniary interest.

F3: On January 4, 2016, in consideration of Michael Barnes' services to the Registrant, Tricadia was granted stock options to purchase 91,359 shares of common stock of the Registrant subject to the terms of a Stock Option Agreement among the Registrant, Michael Barnes and Tricadia (the "Stock Option").

F4: Exercise of the Stock Option is subject to both (1) a time-based vesting requirement with one-third vesting each of January 4, 2019, 2020 and 2021 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 book value per share as of December 31, 2015.

F5: The Stock Option will expire on the earlier of (1) January 4, 2026 and (2) the date of the termination of Michael Barnes's service with the Registrant for Cause (as defined in the Stock Option Agreement) or Michael Barnes's voluntary termination of service with the Registrant.