TIPTREE INC. — Director's Dealing 2014

May 6, 2014

SEC Form 4 — Statement of Changes in Beneficial Ownership

Issuer: TIPTREE FINANCIAL INC. (TIPT)
CIK: 0001393726
Period of Report: 2014-05-02

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

Derivative Transactions

Date	Security	Exercise Price	Code	Shares	A/D	Expiration	Underlying	Ownership
2014-05-02	Tiptree Financial Partners, L.P. partnership unit	$	J	1665798	Acquired		Class A Common Stock (1665798)	Direct
2014-05-02	Tiptree Financial Partners, L.P. partnership unit	$	J	5179839	Acquired		Class A Common Stock (5179839)	Indirect

Holdings (Derivative)

Security	Exercise Price	Expiration	Underlying	Shares	Ownership
Class A Common Stock Warrant	$11.33	2018-09-30	Class A Common Stock (652500)	652500	Indirect
Tiptree Financial Partners, L.P. partnership unit warrant	$8.48	2022-06-30	Class A Common Stock (1767986)	1767986	Indirect
Tiptree Financial Partners, L.P. partnership unit option	$5.36	2017-06-12	Class A Common Stock (1510920)	1510920	Indirect

Footnotes

F1: The reporting person is Executive Chairman and an equity owner of Tiptree Financial Partners, L. P. ("TFP") and Executive Chairman and an equity owner of the Issuer. The reporting person holds voting and investment power with respect to the shares held directly by TFP. The reporting person disclaims beneficial ownership of the reported securities except to the extent of his pecuniary interest.

F2: Pursuant to the limited liability company agreement of Tiptree Operating Company, LLC ("Operating Company"), from and after July 1, 2014, Tiptree Financial Partners, L.P. ("TFP") will have the right to redeem common units of Operating Company held by TFP for an equal number of shares of Class A common stock of the issuer (and an equal number of shares of Class B common stock of Tiptree held by TFP will be canceled). On the terms and conditions set forth in a Redemption Election Notice sent to limited partners of TFP on May 2, 2014, TFP is allowing limited partners of TFP to direct TFP to redeem membership units of Operating Company held by TFP, to occur simultaneously with the redemption by the limited partner of partnership units that indirectly represent the beneficial ownership of the number of shares of Class A common stock to be redeemed upon the redemption by TFP of membership units.

F3: The reporting person is a principal of Tricadia Holdings, L.P. which is the managing member of TFPLP Holdings I LLC and TFPLP Holdings III LLC. 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.

F4: The reporting person is a principal of Tricadia Holdings, L.P. which owns 100% of Tricadia Capital Management, LLC. 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.