Tiptree Inc. (TIPT) CEO exercises 150,742 options; 89,834 shares withheld

Rhea-AI Filing Summary

Tiptree Inc. Chief Executive Officer Jonathan Ilany exercised non-qualified stock options for 137,038 and 13,704 shares of common stock on September 2, 2025, at strike prices of $5.67 and $5.87 through cashless exercises. The issuer withheld 33,262, 3,444 and 53,128 shares at the closing price of $23.36 to fund the option exercise and satisfy withholding tax liabilities. After these transactions, Ilany holds 146,905 common shares directly and 192,021 shares indirectly through a 401(k) plan.

Insights

Securities Analyst

TL;DR: Routine cashless option exercises by the CEO convert vested options to shares while shares were withheld to cover exercise costs and taxes.

The transactions reflect non-qualified option exercises from grants dated 2016. The cashless exercise structure is disclosed clearly: gross option shares issuable are reported alongside the number of shares withheld to fund exercise and tax withholding. Beneficial ownership figures after each line are provided, enabling precise tracking of the reporting person's stake. This is a standard insider liquidity event and does not disclose any new material corporate developments.

Corporate Governance Expert

TL;DR: Filing is compliant and detailed, showing timing, prices, and withholding; it raises no governance red flags.

The Form 4 includes necessary information: transaction codes, exercise prices, market closing price on the transaction date, and the rationale that withholdings funded the cashless exercises and tax obligations. The inclusion of indirect holdings by a 401(k) is helpful for transparency. No departures, grants with special terms, or insider transfers outside normal exercise-and-withhold practices are disclosed.

Insider Trade Summary

Net Buyer: 60,908 shares

Net Buy 8 txns

Insider Ilany Jonathan

Role Chief Executive Officer

Type	Security	Shares	Price	Value
Exercise	Employee Stock Option	137,038	$5.67	$777K
Exercise	Employee Stock Option	13,704	$5.87	$80K
Exercise	Common Stock	137,038	$5.67	$777K
Tax Withholding	Common Stock	33,262	$23.36	$777K
Exercise	Common Stock	13,704	$5.87	$80K
Tax Withholding	Common Stock	3,444	$23.36	$80K
Tax Withholding	Common Stock	53,128	$23.36	$1.24M
holding	Common Stock	--	--	--

Holdings After Transaction: Employee Stock Option — 0 shares (Direct); Common Stock — 146,905 shares (Direct); Common Stock — 192,021 shares (Indirect, By 401K)

Footnotes (9)

1. F1. The transactions reported above in Table I reflect the cashless exercise of stock options. The cashless exercise for the options is reported in two lines. The lines coded M in column 3 of Table I report in column 4 the number of shares issuable upon exercise of the options had cash been paid to exercise the options, together with the exercise price with Code A for acquired. The lines coded F in column 3 of Table I relates to the same cashless exercise on the preceding line and reports in Column 4 the number of shares deducted from the total number of shares issuable to pay for the cashless exercise of such options with Code D for disposed.
2. F2. Reflects 33,262 shares withheld by the Issuer at the market price of $23.36 per share less an exercise price of $5.67 per share to fund the cashless exercise of 137,038 options.
3. F3. Represents the closing stock price as of the transaction date.
4. F4. Reflects 3,444 shares withheld by the Issuer at the market price of $23.36 per share less an exercise price of $5.87 per share to fund the cashless exercise of 13,704 options.
5. F5. Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon the issuance of options exercised cashless calculated at the closing stock price of the exercise date.
6. F6. On January 4, 2016, the Reporting Person was granted non-qualified stock options to purchase 137,038 shares of common stock of the Registrant at $5.67 per share, subject to the terms of a Stock Option Agreement.
7. F7. The option shares are fully vested and exercisable as of January 4, 2021.
8. F8. On March 10, 2016, the Reporting Person was granted non-qualified stock options to purchase 13,704 shares of common stock of the Registrant at $5.87 per share, subject to the terms of a Stock Option Agreement.
9. F9. The option shares are fully vested and exercisable as of March 10, 2021.

Key Figures

Options exercised: 137,038 shares at $5.67 Options exercised: 13,704 shares at $5.87 Shares withheld for exercise: 33,262 shares at $23.36 +4 more

7 metrics

Options exercised 137,038 shares at $5.67 Non-qualified stock options exercised cashless on 2025-09-02

Options exercised 13,704 shares at $5.87 Additional non-qualified options exercised cashless on 2025-09-02

Shares withheld for exercise 33,262 shares at $23.36 Shares withheld to fund cashless exercise of 137,038 options

Shares withheld for exercise 3,444 shares at $23.36 Shares withheld to fund cashless exercise of 13,704 options

Shares withheld for taxes 53,128 shares at $23.36 Shares withheld to satisfy withholding tax liability on exercised options

Direct common stock holding 146,905 shares Post-transaction direct holding of Tiptree common stock

Indirect 401(k) holding 192,021 shares Common stock held indirectly through a 401(k) after the transactions

Key Terms

cashless exercise, non-qualified stock options, withholding tax liability, closing stock price

4 terms

cashless exercise financial

"The transactions reported above in Table I reflect the cashless exercise of stock options."

A cashless exercise is a way for an option holder to convert stock options into actual shares without paying the purchase price in cash; instead they immediately give up a portion of the newly issued shares to cover the cost and any withholding taxes. Investors care because this process increases the number of shares available and can slightly dilute existing holdings, while also signaling how insiders or employees are realizing compensation without needing cash — similar to paying for a purchase by handing over part of what you just bought.

non-qualified stock options financial

"the Reporting Person was granted non-qualified stock options to purchase 137,038 shares"

Non-qualified stock options are a type of employee benefit that gives individuals the right to buy company shares at a set price, usually lower than the market value, within a certain period. Unlike other options that may have special tax advantages, these options are taxed as income when exercised, which can affect how much money the employee or investor ultimately gains. They are important because they can influence company compensation strategies and impact the financial outcomes for employees and investors.

withholding tax liability financial

"shares withheld to satisfy the Reporting Person's withholding tax liability upon the issuance of options exercised cashless"

closing stock price financial

"Represents the closing stock price as of the transaction date."

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Form 4 Insider Transactions: What Each Field Means →

Accepted by SEC EDGAR 09/04/2025 - 04:01 PM Learn about SEC filing dates

FAQ

What did Tiptree (TIPT) CEO Jonathan Ilany report in this Form 4?

Jonathan Ilany reported cashless exercises of non-qualified options for 150,742 shares of Tiptree common stock. The company withheld 89,834 shares at $23.36 to cover exercise and tax costs, leaving him with direct and 401(k) indirect shareholdings.

How many Tiptree (TIPT) stock options did Jonathan Ilany exercise?

He exercised options for 137,038 shares at $5.67 and 13,704 shares at $5.87 of Tiptree common stock. These non-qualified options, granted in 2016 and fully vested by 2021, were exercised via cashless transactions on September 2, 2025.

How many Tiptree (TIPT) shares were withheld in the cashless exercises?

The issuer withheld 33,262 shares and 3,444 shares at $23.36 to fund the cashless option exercises, plus 53,128 shares to satisfy Ilany’s withholding tax liability. These dispositions are reported under transaction code F as non-market tax-withholding events.

What is Jonathan Ilany’s post-transaction Tiptree (TIPT) shareholding?

After the reported transactions, Ilany holds 146,905 Tiptree common shares directly and 192,021 shares indirectly via a 401(k) plan. These figures reflect the net result after option exercises and shares withheld for exercise costs and taxes.

Were Jonathan Ilany’s Tiptree (TIPT) transactions under a Rule 10b5-1 plan?

The disclosure describes cashless exercises of options and related share withholding, but does not state that they were executed under a Rule 10b5-1 trading plan. Plan status is not indicated in the structured data or the accompanying footnotes.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Ilany Jonathan

(Last) (First) (Middle)

C/O TIPTREE INC.

660 STEAMBOAT ROAD, FL 2

(Street)

GREENWICH CT 06830

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
TIPTREE INC. [ TIPT ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

X	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	Chief Executive Officer

3. Date of Earliest Transaction (Month/Day/Year)
09/02/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	09/02/2025		M(1)		137,038	A	$5.67	223,035	D
Common Stock	09/02/2025		F(2)		33,262	D	$23.36(3)	189,773	D
Common Stock	09/02/2025		M(1)		13,704	A	$5.87	203,477	D
Common Stock	09/02/2025		F(4)		3,444	D	$23.36(3)	200,033	D
Common Stock	09/02/2025		F(5)		53,128	D	$23.36(3)	146,905	D
Common Stock								192,021	I	By 401K

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares
Employee Stock Option(6)	$5.67	09/02/2025		M			137,038	(7)	01/04/2026	Common Stock	137,038	$5.67	0	D
Employee Stock Option(8)	$5.87	09/02/2025		M			13,704	(9)	03/10/2026	Common Stock	13,704	$5.87	0	D

Explanation of Responses:

1. The transactions reported above in Table I reflect the cashless exercise of stock options. The cashless exercise for the options is reported in two lines. The lines coded M in column 3 of Table I report in column 4 the number of shares issuable upon exercise of the options had cash been paid to exercise the options, together with the exercise price with Code A for acquired. The lines coded F in column 3 of Table I relates to the same cashless exercise on the preceding line and reports in Column 4 the number of shares deducted from the total number of shares issuable to pay for the cashless exercise of such options with Code D for disposed.

2. Reflects 33,262 shares withheld by the Issuer at the market price of $23.36 per share less an exercise price of $5.67 per share to fund the cashless exercise of 137,038 options.

3. Represents the closing stock price as of the transaction date.

4. Reflects 3,444 shares withheld by the Issuer at the market price of $23.36 per share less an exercise price of $5.87 per share to fund the cashless exercise of 13,704 options.

5. Represents the number of shares withheld to satisfy the Reporting Person's withholding tax liability upon the issuance of options exercised cashless calculated at the closing stock price of the exercise date.

6. On January 4, 2016, the Reporting Person was granted non-qualified stock options to purchase 137,038 shares of common stock of the Registrant at $5.67 per share, subject to the terms of a Stock Option Agreement.

7. The option shares are fully vested and exercisable as of January 4, 2021.

8. On March 10, 2016, the Reporting Person was granted non-qualified stock options to purchase 13,704 shares of common stock of the Registrant at $5.87 per share, subject to the terms of a Stock Option Agreement.

9. The option shares are fully vested and exercisable as of March 10, 2021.

Remarks:

	/s/ Neil C. Rifkind as Attorney-in-Fact for Jonathan Ilany	09/04/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.