Direct Digital Holdings, Inc. 10-Q

ITEM 5. Other Information Rule 10b5-1 Trading Plans During the three months ended September 30, 2023, no director or officer of the Company adopted or terminated a “Rule 10b5-1 trading arrangement” or “non-Rule 10b5-1 trading arrangement,” as each term is defined in Item 408(a) of Regulation S-K. ​ ​ 44 Table of Contents ITEM 6. Exhibits Exhibit No. Description Form File Number Date Exhibit No. Filed or Furnished herewith 3.1 ​ Amended and Restated Certificate of Incorporation of Direct Digital Holdings, Inc. ​ 8-K ​ 001-41261 ​ February 16, 2022 ​ 3.1 ​ 3.2 ​ Amended and Restated Bylaws of Direct Digital Holdings, Inc. ​ 8-K ​ 001-41261 ​ February 16, 2022 ​ 3.2 ​ 10.1 ​ Credit Agreement, dated July 7, 2023, by and among Direct Digital Holdings, Inc., Direct Digital Holdings, LLC, Huddled Masses LLC, Colossus Media, LLC, and Orange142, LLC, as borrowers, and East West Bank, as lender. ​ 8-K ​ 001-41261 ​ July 12, 2023 ​ 10.1 ​ ​ 10.2 ​ Fourth Amendment to Term Loan and Security Agreement, dated October 3, 2023, by and between Direct Digital, LLC, as borrower, Colossus Media, LLC, Huddled Masses LLC, Orange142, LLC, and Direct Digital Holdings, Inc., as guarantors, and Lafayette Square Loan Servicing, LLC, as administrative agent, and the various lenders thereto. ​ 8-K ​ 001-41261 ​ October 10, 2023 ​ 10.1 ​ 10.3 ​ Amendment to Warrant Agreement, effective as of October 3, 2023, by and between the Company and the Warrant Agent. ​ 8-K ​ 001-41261 ​ October 24, 2023 ​ 10.1 ​ 31.1 ​ Certification of the Chief Executive Officer of Direct Digital Holdings, Inc., pursuant to Rule 13a-14(a) of the Exchange Act, as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002. ​ ​ ​ ​ ​ ​ ​ ​ ​ X 31.2 ​ Certification of the Chief Financial Officer of Direct Digital Holdings, Inc, pursuant to Rule 13a-14(a) of the Exchange Act, as adopted pursuant to Section 302 of the Sarbanes-Oxley Act of 2002. ​ ​ ​ ​ ​ ​ ​ ​ ​ X 32.1* ​ Certification of the Chief Executive Officer pursuant to Rule 13a-14(b) of the Exchange Act and 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002. ​ ​ ​ ​ ​ ​ ​ ​ ​ X 32.2* ​ Certification of the Chief Financial Officer pursuant to Rule 13a-14(b) of the Exchange Act and 18 U.S.C. Section 1350, as adopted pursuant to Section 906 of the Sarbanes-Oxley Act of 2002. ​ ​ ​ ​ ​ ​ ​ ​ ​ X 101.INS* ​ Inline XBRL Instance Document ​ ​ ​ ​ ​ ​ ​ ​ ​ X 101.SCH* ​ Inline XBRL Taxonomy Extension Schema ​ ​ ​ ​ ​ ​ ​ ​ ​ X 101.CAL* ​ Inline XBRL Taxonomy Extension Calculation Linkbase ​ ​ ​ ​ ​ ​ ​ ​ ​ X 101.DEF* ​ Inline XBRL Taxonomy Extension Definition Linkbase ​ ​ ​ ​ ​ ​ ​ ​ ​ X 101.LAB* ​ Inline XBRL Taxonomy Extension Label Linkbase ​ ​ ​ ​ ​ ​ ​ ​ ​ X 101.PRE* ​ Inline XBRL Extension Presentation Linkbase ​ ​ ​ ​ ​ ​ ​ ​ ​ X 104* ​ Cover Page Interactive Data File (formatted as inline XBRL and contained in Exhibit 101) ​ ​ ​ ​ ​ ​ ​ ​ ​ X * This exhibit will not be deemed “filed” for purposes of Section 18 of the Exchange Act, or otherwise subject to the liability of that section. Such exhibit will not be deemed to be incorporated by reference into any filing under the Securities Act or the Exchange Act, except to the extent that the Company specifically incorporates it by reference. 45 Table of Contents SIGNATURES Pursuant to the requirements of the Securities Exchange Act of 1934 the Registrant has duly caused this report to be signed on its behalf by the undersigned thereunto duly authorized. Date: November 9, 2023 DIRECT DIGITAL HOLDINGS, INC. ​ ​ ​ ​ ​ By: /s/ Diana P. Diaz ​ ​ DIANA P. DIAZ ​ ​ ​ Chief Financial Officer ​ ​ ​ (Duly Authorized Signatory, Principal Financial and Accounting Officer) ​ ​ ​ ​ 46