Form 4: Strive CEO Matthew Cole Reports Significant Stock Transactions
Insider Transaction Report
Strive, Inc. CEO Matthew Cole reported the settlement of restricted stock units, conversion of Class B to Class A shares, tax withholdings, and a charitable gift of Class B common stock.
Summary
- Matthew Ryan Cole, Chief Executive Officer and Director of Strive, Inc. (ASST), reported multiple transactions related to his beneficial ownership of company stock.
- On September 12, 2025, 18,459,504 Restricted Stock Units (RSUs) vested and settled into Class B Common Stock. This vesting was triggered by the achievement of both time-vesting and performance-vesting conditions, which were deemed met subject to the closing of a merger agreement dated May 6, 2025, and amended June 27, 2025.
- On October 1, 2025, these 18,459,504 Class B Common Stock shares were converted into Class A Common Stock.
- Concurrently, 7,262,330 Class B Common Stock shares were withheld by Strive, Inc. to cover required tax withholding obligations in connection with the RSU settlement. The shares were withheld at a price of $2.5 per share.
- An additional 57,147 Restricted Stock Units, previously reported as 57,183 due to an administrative error, held indirectly by Matthew Ryan Cole's spouse, also vested and settled into Class B Common Stock on October 1, 2025, and were subsequently converted to Class A Common Stock.
- 27,998 Class B Common Stock shares were withheld from the spouse's holdings for tax obligations at a price of $2.5 per share.
- On October 1, 2025, Matthew Ryan Cole made a gift of 3,691,901 Class B Common Stock shares to a charitable organization directly controlled by him and his spouse. No consideration was received for this gift, and the gifted shares are no longer beneficially owned by the reporting person.
- Following these transactions, Matthew Ryan Cole directly beneficially owns 7,505,273 Class B Common Stock shares and indirectly beneficially owns 29,149 Class B Common Stock shares through his spouse.
Sentiment
Score: 5
Explanation: The filing is a factual report of insider transactions, which are neutral in sentiment by themselves. The vesting of RSUs is positive for the insider and implies successful achievement of conditions, while tax withholding and a charitable gift are standard or personal events.
Positives
- The vesting of 18,459,504 Restricted Stock Units for Matthew Ryan Cole and 57,147 for his spouse indicates that performance and time-based conditions, including those tied to a merger agreement, were successfully met.
- The conversion of Class B to Class A Common Stock simplifies the capital structure for the converted shares and may increase liquidity for those specific shares.
Negatives
- A significant number of shares (7,262,330 directly and 27,998 indirectly by spouse) were withheld for tax obligations, reducing the total number of shares beneficially owned.
- The gift of 3,691,901 Class B Common Stock shares to a charitable organization reduces Matthew Ryan Cole's direct beneficial ownership in the company.
Future Outlook
The filing does not provide specific forward-looking statements or guidance regarding the company's future performance or strategic direction. It primarily reports past insider transactions.
Industry Context
This filing is a standard insider transaction report and does not contain information that allows for a direct analysis of broader industry trends or comparisons to competitors. The underlying merger agreement mentioned could be significant for the company's industry position, but details are not provided here.
Corporate Governance
| Change Type | Description | Effective Date | Impact Assessment |
|---|---|---|---|
| Stock Class Conversion Rules | The filing details the mechanics for conversion of Class B Common Stock to Class A Common Stock, which can occur automatically upon certain transfers, by affirmative vote of Class B holders, or at the election of the reporting person. | N/A | These rules define the voting power and liquidity dynamics between different classes of shares, impacting shareholder rights and control structure. |
Related Party Transactions
- Transactions involving the reporting person's spouse, including the vesting of 57,147 Restricted Stock Units and subsequent tax withholding of 27,998 Class B shares.
- A gift of 3,691,901 Class B Common Stock shares to a charitable organization directly controlled by the reporting person and his spouse.
Stakeholder Impact
- Shareholders: Changes in the beneficial ownership of a key executive and director, and the conversion of Class B to Class A shares, could impact perceived insider alignment and voting power distribution.
- Employees: The vesting of RSUs for the CEO indicates successful achievement of performance milestones, which can be a positive signal for employee morale and compensation structures.
Key Dates
| Date | Description |
|---|---|
| 05/06/2025 | Date of the original Agreement and Plan of Merger. |
| 06/27/2025 | Date of the Amended and Restated Agreement and Plan of Merger. |
| 09/12/2025 | Deemed execution date for the achievement of time-vesting and performance-vesting conditions of Restricted Stock Units. |
| 10/01/2025 | Transaction date for RSU settlement, stock conversions, tax withholdings, and charitable gift. |
| 10/03/2025 | Date the Form 4 was signed and filed. |
Keywords
Strive, ASST, Matthew Cole, Form 4, Insider Transaction, Restricted Stock Units, Class B Common Stock, Class A Common Stock, Tax Withholding, Charitable Gift, CEO, Beneficial Ownership
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