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SCHEDULE Filed 2025-02-11 Event 2024-08-22 SEC 0001662991-25-000032 →

Youakim Charles Sezzle Inc. SEZL

Stake: 44.20% Shares: 2,483,231 CUSIP: 78435P105 Class: Common Stock, $0.00001 par value per share

Item 4 — Purpose of Transaction

As of the date of this Amendment No. 1, except as set forth below, the Reporting Persons do not have a plan or proposal that relates to or would result in any of the transactions enumerated in sub items (a) through (j) of the instructions to Item 4 of this Schedule 13D. On July 27, 2019, the Issuer granted Mr. Youakim an option to purchase 13,159 shares of Common Stock at an exercise price equal to $31.92 under the Issuer's 2019 Incentive Plan pursuant to an Option Agreement in the form attached as Exhibit 10.1, which is hereby incorporated by reference. Such option is fully-vested and expires on July 26, 2029 (the "2019 Option Agreement"). On June 14, 2023, the Issuer granted Mr. Youakim 52,632 restricted stock units under the Issuer's 2021 Incentive Plan pursuant to an Equity Incentive Plan Notice Award in the form attached as Exhibit 10.2, which is hereby incorporated by reference (the "2023 RSU Grant"). The restricted stock units vest over a four-year period, with 25% of the award (13,158 shares) vesting on January 1, 2024 and the remaining award vesting with respect to 6.25% of the award (approximately 3,290 shares) on a quarterly basis thereafter. The 2023 RSU Grant is settled in shares of Common Stock on the vesting dates (subject to forfeiture of shares of Common Stock to satisfy tax withholding obligation). On April 1, 2024, the Issuer granted Mr. Youakim an option to purchase 10,803 shares of Common Stock at an exercise price equal to $68.26 under the Issuer's 2021 Incentive Plan pursuant to an Option Agreement in the form attached as Exhibit 10.3, which is hereby incorporated by reference (the "2024 Option Agreement"). The option vests over a four-year period with 25% of the award (2,701 shares) vesting on April 1, 2025, and the remaining award vesting with respect 6.25% of the award (approximately 675 shares) on a quarterly basis thereafter. The option expires on April 1, 2034. On July 16, 2024, Mr. Youakim entered into an Oppenheimer Client Agreement (the "Client Agreement") with Oppenheimer & Co., Inc. ("Oppenheimer") that governs a loan made by Oppenheimer to Mr. Youakim in the principal amount of $10,000,000. In connection with such loan, Mr. Youakim entered into a Pledge Agreement with Oppenheimer dated August 22, 2024 (the "Pledge Agreement"), pursuant to which he pledged as collateral 1,720,600 of his shares of Common Stock in favor of Oppenheimer to secure his obligations under the Client Agreement (the "Pledge"). Mr. Youakim's outstanding obligations under the Client Agreement are payable upon Oppenheimer's demand. The Issuer is not a party to the Client Agreement or the Pledge Agreement. In conjunction with the Pledge, Mr. Youakim deposited 1,720,600 shares of Common Stock with Oppenheimer. Pursuant to the Pledge Agreement, Mr. Youakim agreed that he will not pledge or otherwise encumber any other shares of Common Stock owned by him during the term of the Pledge without the prior written consent of Oppenheimer, and further agreed that he, his spouse, any relatives living in their household, any trust, estate, corporation or other organization in which such persons own 10% of more, or as to which any such persons serves as trustee, executor, board member or similar capacity, will not sell, transfer or otherwise dispose of any shares of Common Stock without giving prior written notice to Oppenheimer. Upon the occurrence of certain events that are customary for these types of loans, including satisfaction of minimum margin maintenance requirements in accordance with Oppenheimer's internal policy or the rules of any organization or agency to which Oppenheimer is subject, Oppenheimer may exercise its rights to require Mr. Youakim to repay the loan proceeds or post additional collateral, and Oppenheimer may exercise its rights to foreclose on, and dispose of, the pledged shares, in each case, in accordance with the Client Agreement and Pledge Agreement. The foregoing description of the Pledge Agreement and Client Agreement does not purport to be complete and is qualified in its entirety by reference to the full copies of the Pledge Agreement and Client Agreement attached hereto as Exhibits 10.4 and 10.5, respectively, and incorporated herein by reference. Notwithstanding the foregoing, the Reporting Persons reserve the right to effect any such actions as any of them may deem necessary or appropriate in the future.

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