System1 (NYSE: SST) insiders’ Kenloch Holdings buy 2.34M shares from Cannae

Rhea-AI Filing Summary

System1, Inc. reported that on December 1, 2025, its largest individual shareholder, Cannae Holdings, LLC, sold 2,344,482 shares of Class A common stock in a privately negotiated off-market transaction. The buyer, Kenloch Holdings, LLC, is a new entity formed by certain members of management and independent directors and managed by co-founder, chief executive officer and board chairman Michael Blend.

Kenloch agreed to pay a total of $9,979,315.50, or $4.2565 per share, made up of $5,239,328.11 in cash and a secured promissory note for $4,739,987.39 that is collateralized by the shares purchased. In connection with this sale, director Ryan Caswell resigned from the board effective at the close of business on December 1, 2025, and his resignation was stated not to be due to any disagreement with the company’s operations, policies or practices.

Insights

Corporate governance and capital markets analyst

Management-led entity buys a large outside holder’s stake, with one director resigning.

The report describes Cannae Holdings, previously the largest individual shareholder of System1, selling 2,344,482 Class A shares in a private, off-market deal to Kenloch Holdings, an entity formed by certain managers and independent directors and managed by CEO and board chair Michael Blend. The consideration totals $9,979,315.50, combining cash of $5,239,328.11 and a secured promissory note of $4,739,987.39 at a per-share price of $4.2565.

This shifts a sizable block of stock from an external financial sponsor to an insider-controlled vehicle, increasing the influence of management and participating directors over the equity base. The promissory note is secured by the acquired shares, which ties repayment directly to that block but does not change the company’s balance sheet, as the transaction occurs between shareholders.

Alongside the sale, director Ryan Caswell resigned effective December 1, 2025, with the report stating his departure did not result from any disagreement on operations, policies or practices. Subsequent disclosures may clarify any changes in ownership concentration, board composition or related-party governance practices following this insider-led acquisition.

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UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

FORM 8-K

CURRENT REPORT

PURSUANT TO SECTION 13 OR 15(d)

OF THE SECURITIES EXCHANGE ACT OF 1934

Date of Report (Date of earliest event reported): December 1, 2025

System1, Inc.

(Exact name of registrant as specified in its charter)

Delaware

001-39331

92-3978051

(State or other jurisdiction of incorporation or organization)

(Commission File Number)

(I.R.S. Employer Identification Number)

4235 Redwood Avenue Los Angeles, California

90066

(Address of principal executive offices)

(Zip Code)

(310) 924-6037

(Registrant's telephone number, including area code)

Not Applicable

(Former name or former address, if changed since last report.)

Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions:

☐			Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425)
☐			Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12)
☐			Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b))
☐			Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c))

Securities registered pursuant to Section 12(b) of the Act:

Title of each class

Trading Symbol

Name of each exchange on which registered

Class A Common Stock, $0.0001 par value per share

SST

New York Stock Exchange

Indicate by check mark whether the registrant is an emerging growth company as defined in Rule 405 of the Securities Act of 1933 (§230.405 of this chapter) or Rule 12b-2 of the Securities Exchange Act of 1934 (§240.12b-2 of this chapter).

Emerging growth company ☒

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

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Section 5 – Corporate Governance and Management

Item 5.02 Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers.

Departure of Directors

On December 1, 2025, in connection with the consummation of the sale by Cannae Holdings, LLC of 2,344,482 Class A Shares of Company Stock of System1, Inc. (the "Company") described in further detail in Item 8.01 below, Ryan Caswell notified the Board of Directors (the "Board") of the Company of his resignation from the Board, effective as of the close of business on December 1, 2025. Mr. Caswell did not serve on a Committee of the Board as of the effective date of his resignation from the Board. Mr. Caswell’s resignation from the Company’s Board did not arise as a result of any disagreement with the Company on any matter relating to the Company’s operations, policies or practices.

Section 8 - Other Events

Item 8.01 Other Events.

Sale of Shares by Cannae Holdings LLC

On December 1, 2025, Cannae Holdings, LLC ("Cannae"), the Company’s largest individual shareholder, completed the sale of 2,344,482 shares of the Company’s Class A Common Stock (the "Cannae Shares") in a privately negotiated off-market transaction (the "Cannae Share Sale") to Kenloch Holdings, LLC ("Kenloch"), a new entity formed by certain members of management and independent directors of the Company and managed by Michael Blend, the Company’s co-founder, chief executive officer and chairman of the board. Pursuant to the terms of the Cannae Share Sale, Kenloch purchased the Cannae Shares for an aggregate purchase price of $9,979,315.50 (or $4.2565 per share), consisting of (i) $5,239,328.11 paid in cash and (ii) a secured promissory note in the aggregate principal amount of $4,739,987.39 (the "Promissory Note"), which is secured by the Cannae Shares.

Section 9 - Financial Statements and Exhibits

Item 9.01 Financial Statements and Exhibits.

(d) Exhibits.

Exhibit No.			Description
104			Cover Page Interactive Data File (embedded within the Inline XBRL document)

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SIGNATURE

Pursuant to the requirements of the Securities Exchange Act of 1934, as amended the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized.

System1, Inc.

Date:

December 3, 2025

By:

/s/ Daniel J. Weinrot

Name:

Daniel J. Weinrot

Title:

General Counsel & Corporate Secretary

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FAQ

What major ownership change did System1 (SST) disclose involving Cannae Holdings?

The company disclosed that Cannae Holdings, LLC, its largest individual shareholder, sold 2,344,482 shares of Class A common stock in a privately negotiated off-market transaction to Kenloch Holdings, LLC.

Who bought the 2,344,482 System1 (SST) shares and who manages the buyer?

The shares were purchased by Kenloch Holdings, LLC, a new entity formed by certain members of management and independent directors, which is managed by Michael Blend, System1’s co-founder, chief executive officer and chairman of the board.

What price and payment structure were used in the System1 (SST) share purchase from Cannae?

Kenloch agreed to pay an aggregate of $9,979,315.50, or $4.2565 per share, consisting of $5,239,328.11 in cash and a secured promissory note with a principal amount of $4,739,987.39, collateralized by the purchased shares.

Did System1 (SST) report any board changes related to the Cannae share sale?

Yes. In connection with the share sale, director Ryan Caswell notified the board of his resignation, effective at the close of business on December 1, 2025. His resignation was stated not to be due to any disagreement with the company’s operations, policies or practices.

Does the System1 (SST) transaction with Kenloch Holdings affect the company’s cash directly?

The report describes a transaction between existing shareholders, with Kenloch paying Cannae using cash and a promissory note; the consideration flows between those parties, not from System1 itself.

How is the promissory note in the System1 (SST) insider-led share purchase secured?

The promissory note issued by Kenloch in the principal amount of $4,739,987.39 is secured by the 2,344,482 shares of Class A common stock acquired from Cannae.