Jonathan Ilany - Nov 22, 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
Stock symbol: TIPT
Transactions as of: Nov 22, 2021
Transactions value $: $0
Form type: 4
Date filed: 11/22/2021, 04:03 PM
Previous filing: Aug 5, 2021
Next filing: Mar 16, 2022

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	TIPT	Common Stock	Options Exercise		+100K	+559.82%		118K	Nov 22, 2021	Direct	F1
transaction	TIPT	Common Stock	Gift	$0	-100K	-84.84%	$0.00	17.9K	Nov 22, 2021	Direct	F2
holding	TIPT	Common Stock						144K	Nov 22, 2021	By IRA
holding	TIPT	Common Stock						34.4K	Nov 22, 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	-100K	-6.67%	$0.00	1.4M	Nov 22, 2021	Common Stock	100K		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.