[Form 4] TIPTREE INC. Insider Trading Activity

Rhea-AI Filing Summary

Lesley Goldwasser, a director of TIPTREE INC. (TIPT), reported an acquisition of 1,807 shares of common stock on 10/03/2025 as the stock component of the director's quarterly-paid annual retainer. The transaction shows a price of $0, indicating these shares were issued as compensation rather than purchased. After the grant, the reporting person beneficially owns 112,362 shares. The Form 4 was signed by an attorney-in-fact on 10/06/2025.

Positive

• Director ownership increased to 112,362 shares, improving alignment with shareholders
• Compensation delivered in equity ties executive interests to long-term share performance

Negative

• Stock issuance at $0 represents potential dilution if repeated frequently
• Transaction lacks dollar disclosure of aggregate expense, so immediate financial impact is unclear

Insights

Corporate Governance Analyst

Director retainer paid in stock modestly raises insider ownership.

Issuing 1,807 shares as the stock portion of a director retainer is a routine governance action that increases a director's stake without an out-of-pocket purchase. Director ownership rising to 112,362 shares can modestly align interests between management and shareholders.

This method of compensation depends on the company’s equity plan and dilutive capacity; monitor future equity grants to see if quarterly in-kind payments are recurring and whether they materially expand the share count over a 12-month horizon.

Equity Compensation Specialist

Non-cash grant recorded as compensation at a $0 price is standard for retainer stock awards.

The transaction code shows acquisition via award rather than open-market purchase, and the explanation confirms this is the quarterly stock portion of the annual retainer. Such grants typically expense as compensation in the company’s financials when recognized.

Investors should note the frequency and size of director retainer issuances over the next 12 months to gauge cumulative dilution and compensation expense effects.

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
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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^*

Goldwasser Lesley

(Last) (First) (Middle)

C/O TIPTREE INC.

660 STEAMBOAT ROAD

(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
	Officer (give title below)		Other (specify below)

3. Date of Earliest Transaction (Month/Day/Year)
10/03/2025

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	10/03/2025		A		1,807(1)	A	$0	112,362	D

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

Explanation of Responses:

1. Represents the stock component of the director's annual retainer fee, which is paid quarterly in arrears.

	/s/ Neil C. Rifkind as Attorney-in-Fact for Lesley Goldwasser	10/06/2025
	** 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.

FAQ

What did Lesley Goldwasser report on Form 4 for TIPT?

The director reported acquisition of 1,807 shares on 10/03/2025 as the stock component of the annual retainer; price shown is $0 and beneficial ownership after the grant is 112,362 shares.

Was the 1,807-share transaction a purchase or a compensation award?

It was a compensation award—the Form 4 explanation states it represents the stock component of the director's annual retainer, paid quarterly in arrears.

Does the Form 4 show any change in control or sale of shares?

No; the filing records an acquisition (A) of shares and does not disclose any sale or disposition.

How might this transaction affect TIPTREE's financials?

The stock grant at $0 will generally be recognized as compensation expense in the company's financial statements when recorded, but the Form 4 does not state the aggregate dollar amount.

When was the Form 4 signed and filed?

The filing shows an attorney-in-fact signature dated 10/06/2025.