Cannae Holdings has sharply reduced its stake in System1, Inc. (SST) and now holds under 5% of the company’s Class A common stock. In a privately negotiated sale on December 1, 2025, Cannae Holdings, LLC sold 2,344,482 shares of System1 Class A common stock at $4.2565 per share, for total consideration of approximately $10.0 million under a Stock Purchase Agreement dated November 24, 2025. Cannae received $5.2 million in cash at closing and a note receivable for the remaining roughly $4.8 million of proceeds.
Following this transaction, Cannae Holdings, Inc. and Cannae Holdings, LLC report beneficial ownership of 356,797 shares, representing 4.4% of System1’s Class A common stock based on 8,128,321 shares outstanding as of October 29, 2025. They state that, as of this amendment, they are not beneficial owners of more than five percent of the class and may no longer be deemed part of a group that owns more than five percent due to their withdrawal from a shareholder agreement.
System1, Inc. (SST): Cannae updates ownership on Schedule 13D/A. Cannae Holdings, Inc. and Cannae Holdings, LLC report beneficial ownership of 2,701,279 shares of Class A common stock, representing 33.2% of the Class A outstanding. The percentage is calculated based on 8,128,321 Class A shares outstanding as of October 29, 2025, as reported in the company’s Form 10‑Q filed on November 5, 2025.
The filing notes that System1’s reported increase in Class A shares outstanding changed Cannae’s ownership by more than one percent versus the prior amendment. Cannae reports 27.0% total voting power. The filing states no ownership of the 1,869,607 Class C shares outstanding as of October 29, 2025. The reporting persons disclose no transactions in Class A shares during the past 60 days.
The filing references a Shareholders Agreement under which certain parties may constitute a “group,” with members filing separate Schedules 13D; the reporting persons disclaim beneficial ownership of shares solely by reason of that agreement.
System1, Inc. (SST) furnished supplemental financial information for the quarter ended September 30, 2025. The company posted the materials on its investor relations website and furnished the same content as Exhibit 99.1 to a Form 8-K under Item 7.01 (Regulation FD Disclosure).
The furnished materials are not deemed “filed” for purposes of Section 18 of the Exchange Act and are not incorporated by reference unless expressly stated. The filing also includes Exhibit 104 for the cover page Inline XBRL data. This update is an informational disclosure to make the Q3 2025 supplemental materials broadly available.
System1, Inc. (SST) filed its Q3 2025 10‑Q, reporting revenue of $61.6 million and a net loss of $22.0 million. Year to date, revenue was $214.2 million with a net loss of $63.4 million. Operating loss narrowed versus last year as costs declined alongside lower revenue.
Segment trends diverged: Marketing revenue fell to $39.1 million, while Products grew to $22.5 million, lifting Products’ adjusted gross profit. Cash and cash equivalents were $54.6 million, and the company had full availability on its $50.0 million revolving facility. The Term Loan had $265.1 million principal outstanding (carrying value $259.2 million) and matures in 2027.
Stockholders’ equity was $34.3 million, reflecting accumulated losses and non‑controlling interest. The company effected a 1‑for‑10 reverse stock split in June 2025. Key paid search partnerships remain in place with Google (through February 28, 2027 and September 30, 2027) and Microsoft (through December 31, 2026). Warrants moved to Level 3 fair value measurement after delisting.
System1, Inc. (SST) furnished an 8-K under Item 2.02 announcing financial results for the quarter ended September 30, 2025. The company issued a press release, attached as Exhibit 99.1, which includes details of the quarter’s performance.
The Item 2.02 information, including Exhibit 99.1, is furnished and not deemed “filed” under the Exchange Act. The press release references certain non-GAAP financial measures, with reconciliations to GAAP and explanations of their use included in the release.
System1, Inc. (SST) reported an insider transaction by its Chief Financial Officer, Tridivesh Kidambi. On 10/28/2025, the company withheld 263 shares of Class A common stock at $6.18 per share to satisfy taxes due upon the vesting of 625 RSUs previously granted to the officer (transaction code F).
Following the withholding, the officer beneficially owned 120,509 shares, which includes 54,814 unvested RSUs. This filing reflects administrative tax withholding rather than an open-market sale.
System1, Inc. (SST) reported an insider tax withholding transaction. A Form 4 shows Chief People Officer Elizabeth Sestanovich had 158 shares of Class A Common Stock withheld at $6.18 on 10/28/2025 (transaction code F) to cover taxes on the vesting of previously granted RSUs.
The filing notes the vesting of 375 RSUs, with the company withholding shares to satisfy tax obligations. Following the transaction, Sestanovich beneficially owns 59,877 shares directly, which includes 43,725 unvested RSUs.
System1, Inc. (SST) reported an insider equity transaction tied to restricted stock vesting. On 10/28/2025, the issuer withheld 235 shares of Class A Common Stock at $6.18 per share (Transaction Code F) to satisfy the reporting person’s tax withholding obligation upon vesting of previously granted RSUs. Following this tax withholding, the reporting person beneficially owns 66,831 shares.
The holdings include 44,239 unvested RSUs. The reporting person is an officer of the company (Chief Ad Operations Officer).
System1, Inc. (SST) reported by officer Daniel J. Weinrot (General Counsel & Secretary) a routine tax-withholding transaction on 10/28/2025. A total of 214 shares of Class A common stock were withheld and disposed of at $6.18 per share under code F to satisfy taxes upon vesting of previously granted RSUs.
Following the transaction, the reporting person beneficially owned 69,982 shares, which includes 56,225 unvested RSUs. The filing was made as a single reporting person submission.
System1, Inc. (SST) filed a Form 4 reporting an automatic share withholding tied to equity compensation. On 10/15/2025, Chief Ad Operations Officer Brian Coppola had 377 shares of Class A common stock withheld at $7.94 per share (code F) to cover taxes upon the vesting of 754 RSUs.
Following the transaction, Coppola beneficially owned 67,066 shares in total, which includes 44,708 unvested RSUs. The filing reflects a non‑open market, tax‑withholding event rather than a discretionary purchase or sale.