Jonathan Ilany - Oct 17, 2024 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: Oct 17, 2024
Transactions value $: $0
Form type: 4
Date filed: 10/18/2024, 04:04 PM
Previous filing: May 28, 2024

Transactions Table

Type	Sym	Class	Transaction	Value $	Shares	Change %	* Price $	Shares After	Date	Ownership	Footnotes
transaction	TIPT	Common Stock	Options Exercise		+200K			200K	Oct 17, 2024	Direct	F1
transaction	TIPT	Common Stock	Gift	$0	-200K	-100%	$0.00	0	Oct 17, 2024	Direct	F2
holding	TIPT	Common Stock						192K	Oct 17, 2024	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 2021	Options Exercise	$0	-200K	-14.29%	$0.00	1.2M	Oct 17, 2024	Common Stock	200K		Direct	F3
holding	TIPT	Performance Restricted Stock Units 2024						550K	Oct 17, 2024	Common Stock	550K		Direct	F4

* 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") upon achieving the $20 Tiptree Inc. ("Tiptree") share price target milestone (adjusted for dividends paid).
F2	The reporting person gifted the vested portion of the PRSUs on October 17, 2024 to a family trust of which the reporting person has no control or beneficial interest.
F3	These PRSUs were granted to the Reporting Person on August 4, 2021. The PRSUs will vest upon Tiptree achieving each of three Tiptree share price target milestones, based on the average of the thirty (30) trading day closing stock price, ranging from $30 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. Each PRSU represents a contingent right to receive one share of Tiptree common stock. Any unvested PRSUs shall expire on August 4, 2031.
F4	These PRSUs were granted to the Reporting Person on January 1, 2024. Each PRSU represents a contingent right to receive one share of Tiptree common stock. The PRSUs will vest upon Tiptree achieving a share price target milestone based on the average of the thirty (30) trading day closing stock price of $70 (adjusted for dividends paid) prior to the 10th anniversary of the grant date, subject to the Reporting Person's continued employment with Tiptree. Any unvested PRSUs shall expire on January 1, 2034.