SCHEDULE: Sezzle Inc. Ownership Update: Youakim's Stake at 39.6%

Charles Youakim and Cerro Gordo LLC report a combined beneficial ownership of 39.6% in Sezzle Inc. following a change in dispositive power over trust-held shares.

Summary

• Charles Youakim and Cerro Gordo LLC (CGL) have filed an amendment to their Schedule 13D, reporting a combined beneficial ownership of 13,413,162 shares of Sezzle Inc. Common Stock, representing 39.6% of the outstanding shares.
• This ownership includes shares held directly by Mr. Youakim, shares issuable upon exercise of his options, and shares owned by CGL.
• A significant change reported is that effective September 2, 2026, Mr. Youakim no longer beneficially owns shares held by the Charles G. Youakim 2020 Irrevocable GST Trust ('2020 Trust') due to a court-ordered dissolution of marriage settlement.
• The filing also notes the vesting of 19,737 restricted stock units (RSUs) under the 2023 RSU Grant held by Mr. Youakim, with 12,759 shares issued on August 10, 2026, after withholding taxes.

Sentiment

Score: 6

Explanation: StockSavvy.ai views this filing as neutral to slightly positive, reflecting a significant ownership stake and a change in beneficial ownership due to personal circumstances, without immediate indications of new strategic direction or financial distress.

Positives

• Charles Youakim maintains a substantial beneficial ownership of 39.6% in Sezzle Inc., indicating continued significant investment and influence.
• The filing clarifies ownership structures, providing transparency to investors.
• Vesting of RSUs and exercise of options suggest ongoing incentive alignment for management.

Negatives

• The reduction in beneficial ownership from the 2020 Trust, while due to personal legal matters, represents a decrease in direct control over those specific shares.
• The deemed price of $118.00 per share for tax withholding on RSUs appears high relative to typical market prices, though this is a standard mechanism.

Risks

• The concentration of ownership in a single individual, even with a court-ordered division, could lead to governance challenges or strategic inflexibility if not managed collaboratively.
• Future changes in Mr. Youakim's personal circumstances or investment strategy could impact his significant stake in Sezzle Inc.

Future Outlook

The filing does not contain specific forward-looking statements or guidance. It primarily reports on changes in beneficial ownership and recent share transactions related to equity awards.

Management Comments

• Reporting Persons, collectively, currently beneficially own 13,413,162 shares of Common Stock, which represents 39.6% of the outstanding shares of Common Stock of the Issuer.
• Mr. Youakim ceased to have any voting or dispositive power over the shares of Common Stock held by the 2020 Trust and, as a result, no longer beneficially owns such shares.

Industry Context

StockSavvy.ai notes that Schedule 13D filings are common for significant shareholders to disclose their holdings and any changes. This particular amendment reflects a shift in beneficial ownership due to personal legal proceedings, which is a factual update rather than a strategic business announcement. The high percentage of ownership by a single individual is typical in certain stages of a company's lifecycle or for founder-led businesses.

Legal Proceedings

• A stipulated judgment and decree from the Family Court Division of the State of Minnesota District Court, Fourth Judicial District, concerning the dissolution of marriage, resulted in Mr. Youakim ceasing to have voting or dispositive power over shares held by the 2020 Trust.

Related Party Transactions

• The filing details transactions related to Mr. Youakim's restricted stock units (RSUs) and options, which are standard compensation arrangements.

Stakeholder Impact

• Shareholders: The filing provides transparency on a significant ownership stake, which can influence market perception. The change in beneficial ownership due to personal matters is unlikely to directly impact day-to-day operations but could be a factor in future governance discussions.
• Management: Mr. Youakim's continued significant ownership reinforces his position, while the RSU vesting confirms ongoing incentive compensation.
• Creditors: No direct impact is indicated.

Next Steps

• Continued monitoring of Charles Youakim's beneficial ownership and any future transactions.
• Observation of any potential strategic implications arising from the concentrated ownership structure.

Key Dates

Keywords

Sezzle Inc., Schedule 13D, Beneficial Ownership, Charles Youakim, Cerro Gordo LLC, Common Stock, RSU Vesting, Ownership Change