Jonathan Ilany - 22 Nov 2021 Form 4 Insider Report for TIPTREE INC. (TIPT)

Role: Chief Executive Officer, Director
Signature: /s/ Neil C. Rifkind as Attorney-in-Fact for Jonathan Ilany
Issuer symbol: TIPT
Transactions as of: 22 Nov 2021
Net transactions value: $0
Form type: 4
Filing time: 22 Nov 2021, 16:03:12 UTC
Previous filing: 05 Aug 2021
Next filing: 16 Mar 2022
SEC: View on sec.gov

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	TIPT	Common Stock	Options Exercise		+100,000	+560%		117,863	22 Nov 2021	Direct	F1
transaction	TIPT	Common Stock	Gift	$0	-100,000	-85%	$0.000000	17,863	22 Nov 2021	Direct	F2
holding	TIPT	Common Stock						144,019	22 Nov 2021	By IRA
holding	TIPT	Common Stock						34,400	22 Nov 2021	By 401K

Derivative Securities (e.g., puts, calls, warrants, options, convertible securities)

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Underlying Class	Amount	Exercise Price	Ownership	Footnotes
transaction	TIPT	Performance Restricted Stock Units	Options Exercise	$0	-100,000	-6.7%	$0.000000	1,400,000	22 Nov 2021	Common Stock	100,000		Direct	F3

* An asterisk sign (*) next to the price indicates that the price is likely invalid.

Explanation of Responses:

Id	Content
F1	The acquisition of the common stock resulted from the vesting of an equal number of performance restricted stock units ("PRSUs") granted on August 4, 2021. Each PRSU represents a contingent right to receive one share of Tiptree Inc. ("Tiptree") common stock.
F2	The reporting person gifted the vested portion of the PRSUs on November 22, 2021 to a family trust of which the reporting person has no control or beneficial interest.
F3	The PRSUs will vest upon Tiptree achieving each of five Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $15 to $60 (adjusted for dividends paid) prior to the tenth anniversary of the date of grant, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on August 4, 2031.