Strive (ASST) CEO RSU Settlement of 18.46M Shares, Tax Withholding 7.26M

Rhea-AI Filing Summary

Matthew Ryan Cole, the Chief Executive Officer and a director of Strive, Inc. (ASST), reported multiple transactions related to Restricted Stock Units and common stock on October 1, 2025 (with one item dated September 12, 2025). Time‑ and performance‑based Restricted Stock Units vested and were settled into 18,459,504 shares of Class B common stock on October 1, 2025. A portion of shares, 7,262,330, were withheld by the company to cover required tax withholding in connection with the settlement. The filing also shows a gift of 3,691,901 Class B shares to a charitable organization controlled by the reporting person and spouse; those shares were transferred without consideration and are no longer beneficially owned by them. The Form 4 notes a prior administrative correction (previously reported as 57,183 RSUs) and explains the conversion mechanics between Class B and Class A shares under the company charter.

Insights

Corporate Governance Expert

Significant insider settlement and charitable gift reshape reported beneficial ownership.

The filing documents the settlement of 18,459,504 Restricted Stock Units into Class B common stock on October 1, 2025, which materially changes the reporting position disclosed for the CEO.

The reported gift of 3,691,901 Class B shares to a charitable organization controlled by the reporting person and spouse is an absolute transfer; the filing states they received no consideration and no longer beneficially own those shares.

Compensation Analyst

Large RSU settlement and tax withholding indicate a major vesting event and taxable settlement.

The company withheld 7,262,330 shares to cover required tax withholding related to the RSU settlement; the filing explicitly says the reporting person did not voluntarily sell any shares.

The Form 4 also corrects a prior administrative error for RSU count (57,183 to 57,147), clarifying the precise equity compensation reconciliation.

Insider Trade Summary

37,033,302 shares exercised/converted

Mixed 7 txns

Insider Cole Matthew Ryan

Role Chief Executive Officer

Type	Security	Shares	Price	Value
Exercise	Class B Common Stock	18,459,504	$0.00	--
Tax Withholding	Class B Common Stock	7,262,330	$2.50	$18.16M
Exercise	Restricted Stock Units	57,147	$0.00	--
Exercise	Class B Common Stock	57,147	$0.00	--
Tax Withholding	Class B Common Stock	27,998	$2.50	$70K
Gift	Class B Common Stock	3,691,901	$0.00	--
Exercise	Restricted Stock Units	18,459,504	$0.00	--

Holdings After Transaction: Class B Common Stock — 18,459,504 shares (Direct); Restricted Stock Units — 0 shares (Indirect, By Spouse); Class B Common Stock — 57,147 shares (Indirect, By Spouse); Restricted Stock Units — 0 shares (Direct)

Footnotes (1)

1. Each share of Class B Common Stock of the Registrant, automatically and without further action by the Reporting Person, is converted into one share of Class A Common Stock, upon the occurrence of a Transfer, other than a Permitted Transfer (each as defined in the Registrant's Amended and Restated Articles of Incorporation) or all shares of Class B Common Stock, automatically and without further action by the Reporting Person, shall be converted into an identical number of shares of Class A Common Stock at such date and time, or the occurrence of an event, specified by the affirmative vote (or written consent if action by written consent of stockholders is permitted at such time under the Registrant's Amended and Restated Articles of Incorporation) of the holders of a majority of the total voting power of the outstanding Class B Common Stock, voting as a separate class. (Footnote 2 continued) The Class B Common Stock may also be converted into Class A Common Stock at the election of the Reporting Person. Each of the time-vesting condition and the performance vesting condition of the Restricted Stock Units was deemed to have been achieved subject to the closing by that certain Agreement and Plan of Merger dated as of May 6, 2025, as amended by that certain Amended and Restated Agreement and Plan of Merger, dated as of June 27, 2025, and such Restricted Stock Units were settled into shares of Class B Common Stock on October 1, 2025. Represents the settlement of Restricted Stock Units into shares of Class B Common Stock. Neither the Reporting Person nor the Reporting Person's spouse voluntarily sold any shares of Class A Common Stock or Class B Common Stock in connection with the transactions reported herein. Represents shares of Class B Common Stock withheld by the Registrant solely to cover required tax withholding obligations in connection with the settlement of Restricted Stock Units. The Reporting Person did not voluntarily sell any shares of Class B Common Stock or Class A Common Stock in connection with the transactions reported herein. Previously reported as 57,183 Restricted Stock Units due to an administrative error. On October 1, 2025, the Reporting Person made a gift of 3,691,901 shares of Class B Common Stock to a charitable organization. The charitable organization is directly controlled by the Reporting Person and his spouse. The Reporting Person and his spouse received no consideration for the gift and no longer beneficially own the gifted shares.

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Form 4 Insider Transactions: What Each Field Means →

Accepted by SEC EDGAR 10/03/2025 - 09:51 PM Learn about SEC filing dates

FAQ

What insider transactions did ASST CEO Matthew Ryan Cole report on Form 4?

The Form 4 reports settlement of 18,459,504 Restricted Stock Units into Class B common stock on October 1, 2025, tax withholding of 7,262,330 shares, and a gift of 3,691,901 Class B shares to a charitable organization controlled by the reporting person and spouse.

Did Matthew Ryan Cole sell any shares in these transactions (ASST)?

No. The filing states the reporting person and his spouse did not voluntarily sell any shares of Class A or Class B common stock in connection with the reported transactions.

Why were 7,262,330 shares withheld in the Form 4?

The filing explains those shares represent Class B common stock withheld by the registrant to cover required tax withholding obligations from the RSU settlement.

What is the significance of the gift of 3,691,901 shares?

The Form 4 states the gift was made to a charitable organization directly controlled by the reporting person and spouse, that they received no consideration, and they no longer beneficially own

Are Class B shares convertible to Class A shares under ASST’s charter?

Yes. The filing reiterates that each Class B share is automatically convertible into one Class A share upon certain transfers (other than permitted transfers) or at such times specified by affirmative vote of the majority of outstanding Class B voting power.

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^*

Cole Matthew Ryan

(Last) (First) (Middle)

C/O STRIVE, INC.

200 CRESCENT COURT SUITE 1400

(Street)

DALLAS TX 75201

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
Strive, Inc. [ ASST ]

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)
10/01/2025

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

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
Restricted Stock Units	(1)(2)(3)	09/12/2025		M			18,459,504(1)(2)(3)(4)	(3)	(1)(2)(3)	Class B Common Stock	18,459,504	(1)(2)(3)	0	D
Class B Common Stock	(1)(2)(3)	10/01/2025		M		18,459,504(1)(2)(3)		(3)	(1)(2)(3)	Class A Common Stock	18,459,504	(1)(2)(3)	18,459,504	D
Class B Common Stock	(1)(2)(3)	10/01/2025		F			7,262,330(5)	(1)(2)(5)	(1)(2)(5)	Class A Common Stock	7,262,330	$2.5	11,197,174	D
Restricted Stock Units	(1)(2)(3)	10/01/2025		M			57,147(1)(2)(4)(6)	(3)	(1)(2)(3)	Class B Common Stock	57,147	(1)(2)(3)	0	I	By Spouse
Class B Common Stock	(1)(2)(3)	10/01/2025		M		57,147(1)(2)(3)		(3)	(1)(2)(3)	Class A Common Stock	57,147	(1)(2)(3)	57,147	I	By Spouse
Class B Common Stock	(1)(2)(3)	10/01/2025		F			27,998(5)	(1)(2)(5)	(1)(2)(5)	Class A Common Stock	27,998	$2.5	29,149	I	By Spouse
Class B Common Stock	(1)(2)	10/01/2025		G			3,691,901(7)	(1)(2)	(1)(2)	Class A Common Stock	3,691,901	$0	7,505,273	D

Explanation of Responses:

1. Each share of Class B Common Stock of the Registrant, automatically and without further action by the Reporting Person, is converted into one share of Class A Common Stock, upon the occurrence of a Transfer, other than a Permitted Transfer (each as defined in the Registrant's Amended and Restated Articles of Incorporation) or all shares of Class B Common Stock, automatically and without further action by the Reporting Person, shall be converted into an identical number of shares of Class A Common Stock at such date and time, or the occurrence of an event, specified by the affirmative vote (or written consent if action by written consent of stockholders is permitted at such time under the Registrant's Amended and Restated Articles of Incorporation) of the holders of a majority of the total voting power of the outstanding Class B Common Stock, voting as a separate class.

2. (Footnote 2 continued) The Class B Common Stock may also be converted into Class A Common Stock at the election of the Reporting Person.

3. Each of the time-vesting condition and the performance vesting condition of the Restricted Stock Units was deemed to have been achieved subject to the closing by that certain Agreement and Plan of Merger dated as of May 6, 2025, as amended by that certain Amended and Restated Agreement and Plan of Merger, dated as of June 27, 2025, and such Restricted Stock Units were settled into shares of Class B Common Stock on October 1, 2025.

4. Represents the settlement of Restricted Stock Units into shares of Class B Common Stock. Neither the Reporting Person nor the Reporting Person's spouse voluntarily sold any shares of Class A Common Stock or Class B Common Stock in connection with the transactions reported herein.

5. Represents shares of Class B Common Stock withheld by the Registrant solely to cover required tax withholding obligations in connection with the settlement of Restricted Stock Units. The Reporting Person did not voluntarily sell any shares of Class B Common Stock or Class A Common Stock in connection with the transactions reported herein.

6. Previously reported as 57,183 Restricted Stock Units due to an administrative error.

7. On October 1, 2025, the Reporting Person made a gift of 3,691,901 shares of Class B Common Stock to a charitable organization. The charitable organization is directly controlled by the Reporting Person and his spouse. The Reporting Person and his spouse received no consideration for the gift and no longer beneficially own the gifted shares.

	/s/ Brian Logan Beirne, attorney-in-fact for Matthew Ryan Cole	10/03/2025
	** 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.