DRCT / Direct Digital Holdings, Inc. - Depositi SEC, Relazione annuale, dichiarazione di delega

Direct Digital Holdings, Inc.
US ˙ NasdaqCM ˙ US25461T1051

Statistiche di base
CIK 1880613
SEC Filings
All companies that sell securities in the United States must register with the Securities and Exchange Commission (SEC) and file reports on a regular basis. These reports include company annual reports (10K, 10Q), news updates (8K), investor presentations (found in 8Ks), insider trades (form 4), ownership reports (13D, and 13G), and reports related to the specific securities sold, such as registration statements and prospectus. This page shows recent SEC filings related to Direct Digital Holdings, Inc.
SEC Filings (Chronological Order)
Questa pagina fornisce un elenco completo e cronologico dei depositi SEC, esclusi i documenti di proprietà che forniamo altrove.
August 12, 2025 8-K

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): August 6, 2025 Direct Digital Hol

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): August 6, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commi

August 11, 2025 8-K

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): August 8, 2025 Direct Digital Hol

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): August 8, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commi

August 11, 2025 EX-10.1

SEVENTH amendment TO term loan and security AGREEMENT

Exhibit 10.1   Execution Version   SEVENTH amendment TO term loan and security AGREEMENT   This Seventh Amendment to Term Loan and Security Agreement (“Agreement”), dated as of August 8, 2025 (the “Effective Date”), is entered into by and between Direct Digital Holdings, LLC, a Texas limited liability company (“Borrower”), Direct Digital Holdings, Inc., a Delaware corporation (“DDH Holdings”), Col

August 11, 2025 EX-10.2

August 8, 2025

Exhibit 10.2 August 8, 2025 Lafayette Square Loan Servicing, LLC Lafayette Square USA, Inc. PO Box 25250 PMB 13941 Miami, Florida 33102-5250 Attention: Susan Golden Re: Exit Fee Ladies and Gentlemen: Reference is made to (i) that certain Term Loan and Security Agreement dated as of December 3, 2021, as amended from time to time, including, as most recently amended pursuant to that certain Seventh

August 11, 2025 EX-3.1

DIRECT DIGITAL HOLDINGS, INC. Certificate of Designation of Series A Convertible Preferred Stock Pursuant To Section 151 of the Delaware General Corporation Law

Exhibit 3.1 DIRECT DIGITAL HOLDINGS, INC. Certificate of Designation of Series A Convertible Preferred Stock Pursuant To Section 151 of the Delaware General Corporation Law DIRECT DIGITAL HOLDINGS, INC., a Delaware corporation (the “Corporation”), in accordance with the provisions of Section 103 of the Delaware General Corporation Law, as amended (the “DGCL”), does hereby certify that, in accordan

August 6, 2025 EX-10.3

Sixth Amendment to Credit Agreement, dated as of August 5, 2025 but effective as July 31, 2025, by and among Direct Digital Holdings, Inc., Direct Digital Holdings, LLC, Colossus Media, LLC, Huddled Masses LLC, and Orange142, LLC, as borrowers, and East West Bank, as lender.

SIXTH AMENDMENT TO CREDIT AGREEMENT This Sixth Amendment to Credit Agreement (“Agreement”), dated as of August 5, 2025, but effective as of July 31, 2025 (the “Effective Date”), is entered into by and among Direct Digital Holdings, Inc.

August 6, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE QUARTERLY PERIOD ENDED JUNE 30, 2025 OR o TRANSITION REPORT PURSUANT SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 001-41

August 6, 2025 EX-10.2

Fifth Amendment to Credit Agreement, dated as of July 17, 2025 but effective as July 7, 2025, by and among Direct Digital Holdings, Inc., Direct Digital Holdings, LLC, Colossus Media, LLC, Huddled Masses LLC, and Orange142, LLC, as borrowers, and East West Bank, as lender.

FIFTH AMENDMENT TO CREDIT AGREEMENT This Fifth Amendment to Credit Agreement (“Agreement”), dated as of July [], 2025, but effective as of July 7, 2025 (the “Effective Date”), is entered into by and among Direct Digital Holdings, Inc.

August 5, 2025 8-K

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): August 5, 2025 Direct Digital Hol

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): August 5, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commi

August 5, 2025 EX-99.1

Direct Digital Holdings Reports Second Quarter 2025 Financial Results Revenues Increased 24% Sequentially Over Q1 2025; Consolidated Gross Margin Improved Sequentially to 35% Compared to 29% in Q1 2025 Reduced Operating Expenses by 25% in Q2 2025 Com

Exhibit 99.1 Direct Digital Holdings Reports Second Quarter 2025 Financial Results Revenues Increased 24% Sequentially Over Q1 2025; Consolidated Gross Margin Improved Sequentially to 35% Compared to 29% in Q1 2025 Reduced Operating Expenses by 25% in Q2 2025 Compared to Q2 2024 Driven by Continued Progress with Strategic Cost Saving Initiatives Net Loss and Adjusted EBITDA(1) Loss Improved Sequen

July 18, 2025 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

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): July 17, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commis

July 18, 2025 EX-10.1

FIFTH AMENDMENT TO CREDIT AGREEMENT

FIFTH AMENDMENT TO CREDIT AGREEMENT This Fifth Amendment to Credit Agreement (“Agreement”), dated as of July [], 2025, but effective as of July 7, 2025 (the “Effective Date”), is entered into by and among Direct Digital Holdings, Inc.

June 10, 2025 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits, Other Events, Submission of Matters to a Vote of Security Holders

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): June 9, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commiss

June 10, 2025 EX-3.1

Certificate of Amendment, filed June 10, 2025

Exhibit 3.1 CERTIFICATE OF AMENDMENT TO AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF DIRECT DIGITAL HOLDINGS, INC. Direct Digital Holdings, Inc. (the “Corporation”), a corporation organized and existing under and by virtue of the General Corporation Law of the State of Delaware (the “DGCL”), does hereby certify: FIRST: That the name of the Corporation is Direct Digital Holdings, Inc. SECON

May 30, 2025 EX-10.1

Employment Agreement applicable to Executive Officers

Exhibit 10.1 [FORM OF] AMENDED AND RESTATED EXECUTIVE EMPLOYMENT AGREEMENT This AMENDED AND RESTATED EXECUTIVE EMPLOYMENT AGREEMENT (“Agreement”) is made by and between Direct Digital Holdings, LLC, a Texas limited liability company (together with its successors and assigns, the “Company”), and [Name] (“Executive”) to be effective as of May 1, 2025 (the “Effective Date”). RECITALS WHEREAS, the Com

May 30, 2025 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

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): May 27, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commiss

May 16, 2025 8-K

Unregistered Sales of Equity Securities, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits

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): May 12, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commiss

May 13, 2025 8-K

Unregistered Sales of Equity Securities, Financial Statements and Exhibits

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): May 7, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commissi

May 8, 2025 424B3

8,500,000 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-284344 PROSPECTUS SUPPLEMENT NO. 2 (to Prospectus dated January 28, 2025) 8,500,000 Shares of Class A Common Stock This prospectus supplement updates and supplements the prospectus dated January 28, 2025 (as may be further supplemented or amended from time to time, the “Prospectus”), which forms part of our Registration Statement on Form S-1 (F

May 7, 2025 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE QUARTERLY PERIOD ENDED MARCH 31, 2025 OR o TRANSITION REPORT PURSUANT SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 001-4

May 6, 2025 EX-99.1

Direct Digital Holdings Reports First Quarter 2025 Financial Results Enhanced Buy-Side Revenue Demonstrating Business Segment Growth as Orange 142 Scales 19% Reduction in Operating Expenses Compared with 1Q24 Driven by Strategic Cost Saving Initiativ

Exhibit 99.1 Direct Digital Holdings Reports First Quarter 2025 Financial Results Enhanced Buy-Side Revenue Demonstrating Business Segment Growth as Orange 142 Scales 19% Reduction in Operating Expenses Compared with 1Q24 Driven by Strategic Cost Saving Initiatives Entered New Strategic Partnerships to Diversify and Expand Addressable Market Houston, May 6, 2025 - Direct Digital Holdings, Inc. (Na

May 6, 2025 8-K

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): May 6, 2025 Direct Digital Holdin

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): May 6, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commissi

April 29, 2025 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ____)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant. x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e

April 29, 2025 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ____)

DEF 14A 1 ddh-2025definitiveproxydef.htm DEF 14A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant. x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of

April 18, 2025 8-K

Other Events

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): April 17, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commi

April 18, 2025 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ____)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant. x Filed by a Party other than the Registrant ¨ Check the appropriate box: x Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e

April 11, 2025 8-K

Unregistered Sales of Equity Securities, Other Events, Shareholder Director Nominations

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): April 7, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commis

April 7, 2025 8-K

Unregistered Sales of Equity Securities

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): April 1, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commis

March 28, 2025 424B3

8,500,000 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-284344 PROSPECTUS SUPPLEMENT NO. 1 (to Prospectus dated January 28, 2025) 8,500,000 Shares of Class A Common Stock This prospectus supplement updates and supplements the prospectus dated January 28, 2025 (as may be further supplemented or amended from time to time, the “Prospectus”), which forms part of our Registration Statement on Form S-1 (F

March 28, 2025 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE FISCAL YEAR ENDED DECEMBER 31, 2024 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 001-412

March 28, 2025 EX-19.1

Insider Trading Policy.

Exhibit 19.1 Direct Digital Holdings, Inc. Insider Trading Policy (effective April 2024) This Insider Trading Policy describes the standards of Direct Digital Holdings, Inc. and its subsidiaries (the “Company”) on trading, and causing the trading of, the Company’s securities or securities of certain other publicly traded companies while in possession of confidential information. This Policy is div

March 28, 2025 EX-21.1

List of Subsidiaries.

Exhibit 21.1 Subsidiaries of Direct Digital Holdings, Inc. Legal Name Jurisdiction of Formation Direct Digital Holdings, LLC Texas Orange 142, LLC Delaware Huddled Masses, LLC Delaware Colossus Media, LLC Delaware

March 28, 2025 POS EX

As filed with the Securities and Exchange Commission on March 27, 2025.

As filed with the Securities and Exchange Commission on March 27, 2025. Registration Statement No. 333-284344 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Post-effective Amendment No. 1 to Form S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 7370 87-2306185 (State or

March 27, 2025 EX-99.1

Direct Digital Holdings Reports Q4 & Full-Year 2024 Financial Results Full Year Revenue of $62.3 Million In-Line with Revised Revenue Guidance Continued to Diversify Customer Base with Leading Sell-Side Partners and Buy-Side Customers in New Vertical

Exhibit 99.1 Direct Digital Holdings Reports Q4 & Full-Year 2024 Financial Results Full Year Revenue of $62.3 Million In-Line with Revised Revenue Guidance Continued to Diversify Customer Base with Leading Sell-Side Partners and Buy-Side Customers in New Verticals Management to Host Conference Call at 5:00 PM ET Today Houston, March 27, 2025 - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct

March 27, 2025 8-K

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): March 27, 2025 Direct Digital Hol

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): March 27, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commi

February 7, 2025 8-K

Other Events

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): February 4, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

February 4, 2025 8-K

Unregistered Sales of Equity Securities, Financial Statements and Exhibits

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): January 29, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

January 28, 2025 424B4

8,500,000 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(4) Registration No. 333-284344 PROSPECTUS 8,500,000 Shares of Class A Common Stock This prospectus relates to the resale by New Circle Principal Investments LLC (“New Circle” or the “selling stockholder”) from time to time, of 8,500,000 shares of our Class A common stock, par value $0.001 per share (the “Class A Common Stock”). The shares of Class A Common Stock being

January 27, 2025 CORRESP

Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310 Houston, Texas 77027

Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310 Houston, Texas 77027 VIA EDGAR January 27, 2025 Securities and Exchange Commission Division of Corporation Finance Office of Trade & Services 100 F Street, N.E. Washington, D.C. 20549 Attn: Rucha Pandit Re: Direct Digital Holdings, Inc. Registration Statement on Form S-1 File No. 333-284344 Request for Acceleration of Effective Date La

January 17, 2025 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) Direct Digital Holdings, Inc.

January 17, 2025 EX-99.2

Amendment to Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan.

Exhibit 99.2 AMENDMENT TO DIRECT DIGITAL HOLDINGS, INC. 2022 OMNIBUS INCENTIVE PLAN This Amendment to the Direct Digital Holdings, Inc. 2022 Omnibus Incentive Plan (the “Plan”), has been adopted by the Board of Directors (the “Board”) and approved by the stockholders of Direct Digital Holdings, Inc. (the “Company”), to be effective as of December 27, 2024. WITNESSETH: WHEREAS, the Company adopted

January 17, 2025 S-8

As filed with the Securities and Exchange Commission on January 17, 2025

As filed with the Securities and Exchange Commission on January 17, 2025 Registration No.

January 17, 2025 S-1

As filed with the Securities and Exchange Commission on January 17, 2025.

As filed with the Securities and Exchange Commission on January 17, 2025. Registration Statement No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 7370 87-2306185 (State or Other Jurisdiction of Incorporation o

January 17, 2025 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-1 (Form Type) Direct Digital Holdings, Inc.

January 13, 2025 8-K

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): January 6, 2025 Direct Digital Ho

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): January 6, 2025 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Comm

January 3, 2025 EX-10.2

Sixth Amendment and Waiver to Term Loan and Security Agreement, dated December 27, 2024, 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.

Exhibit 10.2 Execution Version SIXTH AMENDMENT AND WAIVER TO TERM LOAN AND SECURITY AGREEMENT This Sixth Amendment and Waiver to Term Loan and Security Agreement (“Agreement”), dated as of December 27, 2024 (the “Effective Date”), is entered into by and between Direct Digital Holdings, LLC, a Texas limited liability company (“Borrower”), Direct Digital Holdings, Inc., a Delaware corporation (“DDH

January 3, 2025 EX-10.1

Waiver and Fourth Amendment to Credit Agreement, dated December 27, 2024, by and among Direct Digital Holdings, Inc., Direct Digital Holdings, LLC, Colossus Media, LLC, Huddled Masses LLC, and Orange142, LLC, as borrowers, and East West Bank, as lender.

Exhibit 10.1 WAIVER AND FOURTH AMENDMENT TO CREDIT AGREEMENT This Waiver and Fourth Amendment to Credit Agreement (“Agreement”), dated as of December 27, 2024 (the “Effective Date”), is entered into by and among Direct Digital Holdings, Inc., a Delaware corporation (“DDH Holdings”), Direct Digital Holdings, LLC, a Texas limited liability company (“Direct Digital”), Colossus Media, LLC, a Delaware

January 3, 2025 8-K

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

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 27, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Co

December 30, 2024 8-K

Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

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 20, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Co

December 18, 2024 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

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 12, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Co

December 9, 2024 8-K

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 3, 2024 Direct Digital H

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 3, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

November 22, 2024 SC 13D/A

DRCT / Direct Digital Holdings, Inc. / Direct Digital Holdings, Inc. - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Amendment No.1) Under the Securities Exchange Act of 1934 Direct Digital Holdings, Inc. (Name of Issuer) Class A Common Stock, par value $0.001 per share (Title of Class of Securities) 25461T105 (CUSIP Number) Mark Walker Chief Executive Officer Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310 Houst

November 15, 2024 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ____)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant. x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e

November 15, 2024 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ____)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant. x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e

November 13, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE QUARTERLY PERIOD ENDED SEPTEMBER 30, 2024 OR o TRANSITION REPORT PURSUANT SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 0

November 13, 2024 EX-10.2

Third Amendment to Credit Agreement, dated October 15, 2024, among Direct Digital Holdings, LLC, Huddled Masses LLC, Colossus Media, LLC and Orange 142, LLC, as borrowers, and East West Bank, as lende

Execution Version THIRD AMENDMENT TO CREDIT AGREEMENT This Third Amendment to Credit Agreement (“Agreement”), dated as of October 15, 2024 and effective as of June 30, 2024 (the “Effective Date”), is entered into by and among Direct Digital Holdings, Inc.

November 13, 2024 EX-10.1

Fifth Amendment to Term Loan and Security Agreement, dated as of October 15, 2024, among Direct Digital Holdings, LLC, Lafayette Square Loan Services, LLC, as administrative agent, and the various lenders party thereto.

Execution Version FIFTH AMENDMENT TO TERM LOAN AND SECURITY AGREEMENT This Fifth Amendment to Term Loan and Security Agreement (“Agreement”), dated as of October 15, 2024 and effective as of June 30, 2024 (the “Effective Date”), is entered into by and between Direct Digital Holdings, LLC, a Texas limited liability company (“Borrower”), Direct Digital Holdings, Inc.

November 12, 2024 EX-99.1

Direct Digital Holdings Reports Q3 2024 Financial Results Company Launches Colossus Connections to Accelerate Direct Integration Efforts with Leading Demand-Side Platforms New Unified Buy-Side Operating Structure Creates Additional Business Lines and

Exhibit 99.1 Direct Digital Holdings Reports Q3 2024 Financial Results Company Launches Colossus Connections to Accelerate Direct Integration Efforts with Leading Demand-Side Platforms New Unified Buy-Side Operating Structure Creates Additional Business Lines and Revenue Opportunities Company to Host Conference Call at 5:00 PM ET Today Houston, November 12, 2024 - Direct Digital Holdings, Inc. (Na

November 12, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): November 12, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Co

November 7, 2024 424B4

2,932,113 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(4) Registration No. 333-282762 PROSPECTUS 2,932,113 Shares of Class A Common Stock This prospectus relates to the resale by New Circle Principal Investments LLC (“New Circle” or the “selling stockholder”) from time to time, of 2,932,113 shares of our Class A common stock, par value $0.001 per share (the “Class A Common Stock”). The shares of Class A Common Stock being

November 5, 2024 PRE 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ____)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant. x Filed by a Party other than the Registrant ¨ Check the appropriate box: x Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e

October 31, 2024 CORRESP

Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310 Houston, Texas 77027

Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310 Houston, Texas 77027 VIA EDGAR October 31, 2024 Securities and Exchange Commission Division of Corporation Finance Office of Trade & Services 100 F Street, N.E. Washington, D.C. 20549 Attn: Kate Beukenkamp Re: Direct Digital Holdings, Inc. Registration Statement on Form S-1 File No. 333-282762 Request for Acceleration of Effective Date

October 25, 2024 8-K

Other Events, Shareholder Director Nominations

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): October 25, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

October 22, 2024 S-1

As filed with the Securities and Exchange Commission on October 22, 2024.

As filed with the Securities and Exchange Commission on October 22, 2024. Registration Statement No. 333- UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Form S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 7370 87-2306185 (State or Other Jurisdiction of Incorporation o

October 22, 2024 EX-FILING FEES

Filing Fee Table

Exhibit 107.1 Calculation of Filing Fee Tables Form S-3 (Form Type) Direct Digital Holdings, Inc. (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule(1) Amount Registered(2) Proposed Maximum Offering Price Per Unit(1) Maximum Aggregate Offering Price(1) Fee Rate Amount of Registration Fee Equity Class A

October 21, 2024 EX-10.1

Share Purchase Agreement, dated October 18, 2024, between Direct Digital Holdings, Inc. and New Circle Principal Investments LLC

Exhibit 10.1 Execution Version SHARE PURCHASE AGREEMENT This Share Purchase Agreement (the “Agreement”), dated as of October 18, 2024, is made by and between New Circle Principal Investments LLC, a Delaware limited liability company (the “Investor”), and Direct Digital Holdings, Inc., a Delaware corporation (the “Company”). The Investor and the Company may be referred to herein individually as a “

October 21, 2024 EX-10.2

Registration Rights Agreement, dated as of October 18, 2024, between Direct Digital Holdings, Inc. and New Circle Principal Investments LLC

Exhibit 10.2 Execution Version REGISTRATION RIGHTS AGREEMENT THIS REGISTRATION RIGHTS AGREEMENT (this “Agreement”) dated as of October 18, 2024 is made by and between New Circle Principal Investments LLC, a Delaware limited liability company (the “Investor”), and Direct Digital Holdings, Inc., a Delaware corporation (the “Company”). The Investor and the Company may be referred to herein individual

October 21, 2024 EX-99.1

Direct Digital Holdings Announces Strategic $20 Million Equity Reserve Facility to Accelerate Growth Plan

Exhibit 99.1 Direct Digital Holdings Announces Strategic $20 Million Equity Reserve Facility to Accelerate Growth Plan Houston, October 21, 2024 /PRNewswire/ - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct Digital Holdings" or the "Company"), a leading advertising and marketing technology platform operating through its companies Colossus Media, LLC ("Colossus SSP"), Orange142, LLC ("Orange

October 21, 2024 8-K

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits

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): October 18, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

October 16, 2024 8-K

Other Events

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): October 16, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

October 15, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE QUARTERLY PERIOD ENDED MARCH 31, 2024 OR o TRANSITION REPORT PURSUANT SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 001-4

October 15, 2024 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE FISCAL YEAR ENDED DECEMBER 31, 2023 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 001-412

October 15, 2024 8-K

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): October 14, 2024 Direct Digital H

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): October 14, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

October 15, 2024 EX-4.2

Description of the Registrant’s Securities.

Exhibit 4.2 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 The “Company,” “Direct Digital,” “Direct Digital Holdings,” “DDH,” “we,” “us” and “our” refer to Direct Digital Holdings, Inc. The following description summarizes the material terms and provisions of the registered securities of Direct Digital Holdings, Inc. Because it i

October 15, 2024 EX-97

Direct Digital Holdings, Inc. Clawback Polic

Exhibit 97 Approved November 2023 DIRECT DIGITAL HOLDINGS, INC. Clawback Policy Incentive Compensation Clawback Policy This Clawback Policy (“Policy”) of Direct Digital Holdings, Inc. (the “Company”) shall be administered by the Board of Directors (the “Board”) (or an appropriate committee or committees of the Board, as may be designated by the Board). Any determinations made by the Board or commi

October 15, 2024 EX-99.1

Direct Digital Holdings Reports Filings for Full-Year 2023, Q1 2024 and Q2 2024

Exhibit 99.1 Direct Digital Holdings Reports Filings for Full-Year 2023, Q1 2024 and Q2 2024 Houston, October 15, 2024 /PRNewswire/ - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct Digital Holdings" or the "Company"), a leading advertising and marketing technology platform operating through its companies Colossus Media, LLC ("Colossus SSP"), Orange142, LLC ("Orange 142") and Huddled Masses

October 15, 2024 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE QUARTERLY PERIOD ENDED JUNE 30, 2024 OR o TRANSITION REPORT PURSUANT SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 001-41

October 15, 2024 EX-21.1

List of Subsidiaries.

Exhibit 21.1 Subsidiaries of Direct Digital Holdings, Inc. Legal Name Jurisdiction of Formation Direct Digital Holdings, LLC Texas Orange 142, LLC Delaware Huddled Masses, LLC Delaware Colossus Media, LLC Delaware

October 15, 2024 EX-10.11

Executive Employment Agreement, effective as of August 22, 2022, between Direct Digital Holdings, LLC and Maria Vilchez Lowrey

Exhibit 10.11 EXECUTIVE EMPLOYMENT AGREEMENT This EXECUTIVE EMPLOYMENT AGREEMENT (“Agreement”) is made by and between Direct Digital Holdings, LLC, a Texas limited liability company (together with its successors and assigns, the “Company”), and Maria Lowery (“Executive”). This Agreement shall be effective upon Executive’s start date with the Company, which will be August 22, 2022 unless otherwise

August 27, 2024 EX-99.1

Direct Digital Holdings Announces Receipt of Anticipated Additional Delinquency Notice

Exhibit 99.1 Direct Digital Holdings Announces Receipt of Anticipated Additional Delinquency Notice HOUSTON, August 27, 2024 /PRNewswire/ - Today, Direct Digital Holdings, Inc. (the "Company") reported that the Company received an additional delinquency notice (the “Notice”) from the Listing Qualifications Department of The Nasdaq Stock Market LLC (“Nasdaq”) on August 21, 2024, which indicated tha

August 27, 2024 8-K

Regulation FD Disclosure, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits, Other Events

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): August 21, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Comm

August 15, 2024 NT 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING (Check one): ¨ Form 10-K ¨ Form 20-F ¨ Form 11-K x Form 10-Q ¨ Form 10-D ¨ Form N-SAR ¨ Form N-CSR For Period Ended: June 30, 2024                                                          ¨ Transition Report on Form 10-K ¨ Transition Report on Form 20-F ¨ Transition Report on Form 11-K ¨

July 23, 2024 8-K

Other Events

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): July 17, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commis

June 10, 2024 8-K

Changes in Registrant's Certifying Accountant

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): June 10, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commis

May 24, 2024 EX-99.1

Direct Digital Holdings Announces Receipt of Expected Delinquency Notification Letter From Nasdaq Relating to Non-Compliance with Listing Rule 5250(c)(1)

Exhibit 99.1 Direct Digital Holdings Announces Receipt of Expected Delinquency Notification Letter From Nasdaq Relating to Non-Compliance with Listing Rule 5250(c)(1) HOUSTON, May 24, 2024 /PRNewswire/ - Today, Direct Digital Holdings, Inc. (the "Company") reported that the Company received an expected delinquency notification letter (the “Notice”) from the Listing Qualifications Department of the

May 24, 2024 8-K

Regulation FD Disclosure, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits, Other Events

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): May 21, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commiss

May 16, 2024 NT 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING (Check one): ¨ Form 10-K ¨ Form 20-F ¨Form 11-K x Form 10-Q ¨ Form 10-D ¨ Form N-SAR ¨ Form N-CSR For Period Ended: March 31, 2024                                                          ¨ Transition Report on Form 10-K ¨ Transition Report on Form 20-F ¨ Transition Report on Form 11-K ¨

April 23, 2024 8-K

Regulation FD Disclosure, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Financial Statements and Exhibits, Changes in Registrant's Certifying Accountant, Other Events

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): April 17, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commi

April 23, 2024 EX-99.1

Direct Digital Holdings Announces Receipt of Nasdaq Notification of Non-Compliance with Listing Rule 5250(c)(1)

Exhibit 99.1 Direct Digital Holdings Announces Receipt of Nasdaq Notification of Non-Compliance with Listing Rule 5250(c)(1) Houston, April 23, 2024 – Today, Direct Digital Holdings, Inc. (the “Company”) reported that as a result of requiring additional time to complete the audit of its financial statements, on April 17, 2024 it received a notice (the “Notice”) from the Listing Qualifications Depa

April 23, 2024 EX-16.1

Letter from Marcum LLP to the Securities and Exchange Commission, dated April 23, 2024.

Exhibit 16.1 April 23, 2024 Securities and Exchange Commission 100 F Street, N.E. Washington, DC 20549 Commissioners: We have read the statements made by Direct Digital Holdings, Inc. under Item 4.01 of its Form 8-K dated April 17, 2024. We agree with the statements concerning our Firm in such Form 8-K; we are not in a position to agree or disagree with other statements contained therein. Very tru

April 2, 2024 NT 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING (Check one): x Form 10-K o Form 20-F o Form 11-K o Form 10-Q o Form 10-D o Form N-SAR o Form N-CSR For Period Ended: December 31, 2023 o Transition Report on Form 10-K o Transition Report on Form 20-F o Transition Report on Form 11-K o Transition Report on Form 10-Q o Transition Report o

April 2, 2024 EX-99.1

April 2, 2024

Exhibit 99.1 April 2, 2024 Board of Directors Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310 Houston, Texas 77027 Ladies and Gentlemen: Pursuant to Rule 12b-25 of the General Rules and Regulations under the Securities Exchange Act of 1934, as amended, we inform you that we have been furnished a copy of Form 12b-25, to be filed by Direct Digital Holdings, Inc. on or about April 2, 2

March 26, 2024 EX-99.1

Direct Digital Holdings Reports Q4 & Full-Year 2023 Results Company’s Full-Year 2023 Revenue Up 76% Year-Over-Year to $157.1 Million, the Eighth Consecutive Quarter of Double-Digit Growth Full-Year 2023 Net Income of $2.0 million; Adjusted EBITDA(1)

Exhibit 99.1 Direct Digital Holdings Reports Q4 & Full-Year 2023 Results Company’s Full-Year 2023 Revenue Up 76% Year-Over-Year to $157.1 Million, the Eighth Consecutive Quarter of Double-Digit Growth Full-Year 2023 Net Income of $2.0 million; Adjusted EBITDA(1) Up 11% Year-Over-Year to $11.3 Million Company Issues Full-Year 2024 Revenue Guidance of $170 Million – $190 Million Houston, March 26, 2

March 26, 2024 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): March 26, 2024 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commi

January 12, 2024 SC 13D

DRCT / Direct Digital Holdings, Inc. / Direct Digital Management, LLC - SC 13D Activist Investment

SC 13D 1 tm243254d1sc13d.htm SC 13D UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 Direct Digital Holdings, Inc. (Name of Issuer) Class A Common Stock, par value $0.001 per share (Title of Class of Securities) 25461T105 (CUSIP Number) Mark Walker Chief Executive Officer Direct Digital Holdings, Inc. 1177 West Loop Sout

November 30, 2023 EX-10.1

Second Amendment to Credit Agreement, dated November 27, 2023, by and among the Company, Direct Digital Holdings, LLC, Colossus Media, LLC, Huddled Masses LLC, and Orange142, LLC, as borrowers, and East West Bank, as lender.

Exhibit 10.1   Second AMENDMENT TO CREDIT AGREEMENT   This Second Amendment to Credit Agreement (“Amendment”), dated as of November 27, 2023 (the “Effective Date”), is entered into by and among Direct Digital Holdings, Inc., a Delaware corporation (“DDH Holdings”), Direct Digital Holdings, LLC, a Texas limited liability company (“Direct Digital”), Colossus Media, LLC, a Delaware limited liability

November 30, 2023 8-K

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): November 27, 2023 Direct Digital

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): November 27, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Co

November 28, 2023 424B3

2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants

Prospectus Supplement No. 7 (to Prospectus dated February 10, 2022) Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-261059 2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants This prospectus supplement updates and supplements the prospectus dated February 10, 2022 (the “Prospectus”), which forms a part of our Registration Statement on Form S-1. This prospectus

November 28, 2023 424B3

2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants

Prospectus Supplement No. 6 (to Prospectus dated February 10, 2022) Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-261059 2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants This prospectus supplement updates and supplements the prospectus dated February 10, 2022 (the “Prospectus”), which forms a part of our Registration Statement on Form S-1. This prospectus

November 28, 2023 424B3

2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants

Prospectus Supplement No. 8 (to Prospectus dated February 10, 2022) Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-261059 2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants This prospectus supplement updates and supplements the prospectus dated February 10, 2022 (the “Prospectus”), which forms a part of our Registration Statement on Form S-1. This prospectus

November 14, 2023 CORRESP

Quality Guidelines for Creative

November 14, 2023 VIA EDGAR Amy Geddes and Lyn Shenk Division of Corporation Finance Office of Trade & Services United States Securities and Exchange Commission 100 F Street, N.

November 9, 2023 EX-99.1

Direct Digital Holdings Reports Third Quarter 2023 Financial Results Third Quarter 2023 Revenue Up 129% Year-Over-Year to $59.5 Million Company Raises Full-Year 2023 Revenue Guidance to $170 Million - $190 Million

Exhibit 99.1 Direct Digital Holdings Reports Third Quarter 2023 Financial Results Third Quarter 2023 Revenue Up 129% Year-Over-Year to $59.5 Million Company Raises Full-Year 2023 Revenue Guidance to $170 Million - $190 Million Houston, November 09, 2023 - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct Digital Holdings" or the "Company"), a leading advertising and marketing technology platfo

November 9, 2023 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): November 9, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

November 9, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE QUARTERLY PERIOD ENDED SEPTEMBER 30, 2023 OR ☐ TRANSITION REPORT PURSUANT SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 0

October 31, 2023 8-K

Financial Statements and Exhibits, Other Events

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): October 31, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

October 31, 2023 EX-99.1

Direct Digital Holdings Announces Completion of Redemption of Outstanding Warrants

Exhibit 99.1 Direct Digital Holdings Announces Completion of Redemption of Outstanding Warrants Houston, October 31, 2023 /PRNewswire/ - Direct Digital Holdings, Inc. (Nasdaq: DRCT) (“Direct Digital Holdings” or the “Company”), a leading advertising and marketing technology platform operating through its companies Colossus Media, LLC (“Colossus SSP”), Huddled Masses LLC (“Huddled Masses”) and Oran

October 30, 2023 CORRESP

October 30, 2023

October 30, 2023 VIA EDGAR Amy Geddes and Lyn Shenk Division of Corporation Finance Office of Trade & Services United States Securities and Exchange Commission 100 F Street, N.

October 24, 2023 EX-10.1

Amendment to Warrant Agreement, effective as of October 3, 2023, by and between the Company and the Warrant Agent.

Exhibit 10.1 AMENDMENT TO WARRANT AGREEMENT This Amendment to Warrant Agreement (this “Amendment”) is made effective as of October 3, 2023 by and between Direct Digital Holdings, Inc., a Delaware corporation (the “Company”), and Equiniti Trust Company, LLC (formerly American Stock Transfer & Trust Company, LLC), a New York corporation, as warrant agent (the “Warrant Agent”), and constitutes an ame

October 24, 2023 EX-99.1

NOTICE OF REDEMPTION OF WARRANTS (CUSIP 25461T113)

Exhibit 99.1 October 23, 2023 NOTICE OF REDEMPTION OF WARRANTS (CUSIP 25461T113) Dear Warrant Holder, Direct Digital Holdings, Inc. (the “Company”) hereby gives notice that it is redeeming, at 5:00 p.m. New York City time on October 30, 2023 (the “Redemption Date”), all of the Company’s outstanding warrants (the “Warrants”) to purchase shares of the Company’s Class A Common Stock, par value $0.000

October 24, 2023 8-K

Entry into a Material Definitive Agreement, Material Modification to Rights of Security Holders, Financial Statements and Exhibits, Other Events

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): October 19, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

October 18, 2023 EX-99.1

Direct Digital Holdings Appoints Diana Diaz as Chief Financial Officer

Exhibit 99.1 Direct Digital Holdings Appoints Diana Diaz as Chief Financial Officer Houston, October 18, 2023 /PRNewswire/ - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct Digital Holdings" or the “Company”), a leading advertising and marketing technology platform operating through its companies Colossus Media, LLC (“Colossus SSP”), Huddled Masses LLC (“Huddled Masses”) and Orange142, LLC (

October 18, 2023 8-K

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): October 16, 2023 Direct Digital H

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): October 16, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

October 18, 2023 EX-10.1

Executive Employment Agreement, effective as of October 16, 2023, between Direct Digital Holdings, LLC and Diana Diaz.

Exhibit 10.1 Executive Employment Agreement This EXECUTIVE EMPLOYMENT AGREEMENT (“Agreement”) is made by and between Direct Digital Holdings, LLC, a Texas limited liability company (together with its successors and assigns, the “Company”), and Diana Diaz (“Executive”) to be effective as of October 16, 2023 (the “Effective Date”). RECITALS WHEREAS, the Company desires to hire and employ Executive p

October 10, 2023 EX-10.1

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.

Exhibit 10.1 Execution Version FOURTH AMENDMENT TO TERM LOAN AND SECURITY AGREEMENT This Fourth Amendment to Term Loan and Security Agreement (“Amendment”), dated effective as of October 3, 2023 (the “Effective Date”), is entered into by and between Direct Digital Holdings, LLC, a Texas limited liability company (“Borrower”), Direct Digital Holdings, Inc., a Delaware corporation (“DDH Holdings”),

October 10, 2023 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

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): October 3, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Comm

September 29, 2023 EX-99.1

Direct Digital Holdings Announces Expiration and Results of the Offer to Purchase and Consent Solicitation Relating to its Warrants

Exhibit 99.1 Direct Digital Holdings Announces Expiration and Results of the Offer to Purchase and Consent Solicitation Relating to its Warrants Houston, September 29, 2023 - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct Digital Holdings" or the "Company"), a leading advertising and marketing technology platform operating through its companies Colossus Media, LLC ("Colossus SSP"), Huddled

September 29, 2023 8-K

Financial Statements and Exhibits, Other Events

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): September 29, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (C

September 29, 2023 SC TO-I/A

As filed with the Securities and Exchange Commission on September 29, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of

As filed with the Securities and Exchange Commission on September 29, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

September 21, 2023 EX-99.(A)(1)(A)

Second Amended and Restated Offer to Purchase and Consent Solicitation, dated September 21, 2023.

TABLE OF CONTENTS  Exhibit (a)(1)(A) SECOND AMENDED AND RESTATED OFFER TO PURCHASE BY DIRECT DIGITAL HOLDINGS, INC.

September 21, 2023 8-K

Financial Statements and Exhibits, Other Events

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): September 21, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (C

September 21, 2023 CORRESP

McGuireWoods LLP

McGuireWoods LLP 1251 Avenue of the Americas 20th Floor New York, NY 10020 VIA EDGAR AND EMAIL September 21, 2023 U.

September 21, 2023 EX-99.(A)(5)(III)

Press Release, dated September 21, 2023, announcing extension of the Expiration Date of the cash tender offer for Direct Digital Holdings, Inc. warrants

Exhibit (a)(5)(iii) Direct Digital Holdings Announces Extension of the Expiration of the Previously Commenced Offer to Purchase and Consent Solicitation Relating to its Warrants Houston, September 21, 2023 - Direct Digital Holdings, Inc.

September 21, 2023 EX-99.1

Direct Digital Holdings Announces Extension of the Expiration of the Previously Commenced Offer to Purchase and Consent Solicitation Relating to its Warrants

Exhibit 99.1 Direct Digital Holdings Announces Extension of the Expiration of the Previously Commenced Offer to Purchase and Consent Solicitation Relating to its Warrants Houston, September 21, 2023 - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct Digital Holdings" or the "Company"), a leading advertising and marketing technology platform operating through its companies Colossus Media, LLC

September 21, 2023 SC TO-I/A

As filed with the Securities and Exchange Commission on September 21, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of

As filed with the Securities and Exchange Commission on September 21, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

September 18, 2023 CORRESP

⁕⁕⁕

September 18, 2023 VIA EDGAR Amy Geddes and Lyn Shenk Division of Corporation Finance Office of Trade & Services United States Securities and Exchange Commission 100 F Street, N.

September 14, 2023 EX-99.(A)(1)(A)

Amended and Restated Offer to Purchase and Consent Solicitation, dated September 14, 2023.

TABLE OF CONTENTS  Exhibit (a)(1)(A) AMENDED AND RESTATED OFFER TO PURCHASE BY DIRECT DIGITAL HOLDINGS, INC.

September 14, 2023 CORRESP

McGuireWoods LLP

McGuireWoods LLP 1251 Avenue of the Americas 20th Floor New York, NY 10020 VIA EDGAR AND EMAIL September 14, 2023 U.

September 14, 2023 SC TO-I/A

As filed with the Securities and Exchange Commission on September 14, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of

As filed with the Securities and Exchange Commission on September 14, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

September 14, 2023 EX-FILING FEES

Filing Fee Table

EX-FILING FEES Calculation of Filing Fee Tables SC TO-I (Form Type) Direct Digital Holdings, Inc.

September 11, 2023 CORRESP

September 11, 2023

September 11, 2023 VIA EDGAR Amy Geddes and Lyn Shenk Division of Corporation Finance Office of Trade & Services United States Securities and Exchange Commission 100 F Street, N.

August 29, 2023 EX-99.(A)(1)(A)

Offer to Purchase and Consent Solicitation, dated August 29, 2023.

Exhibit (a)(1)(A) OFFER TO PURCHASE BY DIRECT DIGITAL HOLDINGS, INC. OF ANY AND ALL OF ITS WARRANTS TO PURCHASE SHARES OF CLASS A COMMON STOCK AT A PURCHASE PRICE OF $1.20 IN CASH PER WARRANT AND CONSENT SOLICITATION THE OFFER PERIOD AND YOUR RIGHT TO WITHDRAW WARRANTS THAT YOU TENDER WILL EXPIRE AT ONE MINUTE AFTER 11:59 P.M., EASTERN TIME, ON SEPTEMBER 26, 2023, UNLESS THE OFFER PERIOD IS  EXTEN

August 29, 2023 EX-99.(A)(5)(I)

Press Release, dated August 29, 2023, announcing cash tender offer for Direct Digital Holdings, Inc. warrants.

Exhibit (a)(5)(i) Direct Digital Holdings Announces Commencement of an Offer to Purchase and Consent Solicitation Relating to its Warrants Houston, August 29, 2023 - Direct Digital Holdings, Inc.

August 29, 2023 EX-FILING FEES

Filing Fee Table

EX-FILING FEES Calculation of Filing Fee Tables SC TO-I (Form Type) Direct Digital Holdings, Inc.

August 29, 2023 SC TO-I

As filed with the Securities and Exchange Commission on August 29, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE TO Tender Offer Statement under Section 14(d)(1) or 13(e)(1) of the Securities Exchange Act of 19

As filed with the Securities and Exchange Commission on August 29, 2023 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.

August 29, 2023 EX-99.(A)(1)(E)

Form of Letter to Clients for use by Brokers, Dealers, Commercial Banks, Trust Companies and Other Nominees, dated August 29, 2023.

Exhibit (a)(1)(E) Offer to Purchase Warrants to Acquire Shares of Class A Common Stock of Direct Digital Holdings, Inc.

August 29, 2023 CORRESP

August 29, 2023

August 29, 2023 VIA EDGAR Amy Geddes and Lyn Shenk Division of Corporation Finance Office of Trade & Services United States Securities and Exchange Commission 100 F Street, N.

August 29, 2023 8-K

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): August 29, 2023 Direct Digital Ho

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): August 29, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Comm

August 29, 2023 EX-99.(A)(1)(B)

Letter of Transmittal and Consent (including Guidelines of the Internal Revenue Service for Certification of Taxpayer Identification Number on Form W-9).

Exhibit (a)(1)(B) LETTER OF TRANSMITTAL AND CONSENT Offer To Purchase Warrants to Acquire Shares of Class A Common Stock of Direct Digital Holdings, Inc.

August 29, 2023 EX-99.1

Direct Digital Holdings Announces Commencement of an Offer to Purchase and Consent Solicitation Relating to its Warrants

Exhibit 99.1 Direct Digital Holdings Announces Commencement of an Offer to Purchase and Consent Solicitation Relating to its Warrants Houston, August 29, 2023 - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct Digital Holdings" or the "Company"), a leading advertising and marketing technology platform operating through its companies Colossus Media, LLC ("Colossus SSP"), Huddled Masses LLC ("H

August 29, 2023 EX-99.(A)(5)(II)

Summary Advertisement, dated August 29, 2023, announcing cash tender offer for Direct Digital Holdings, Inc. warrants.

Exhibit (a)(5)(ii) Notice of Offer to Purchase by Direct Digital Holdings, Inc. of Warrants to Acquire Class A Common Stock Direct Digital Holdings, Inc. (the “Company”), hereby offers to purchase any and all outstanding warrants to purchase Class A common stock which were publicly issued and sold as part of units of the Company, in connection with the initial public offering of the Company’s secu

August 29, 2023 EX-99.(A)(1)(C)

Form of Notice of Guaranteed Delivery.

Exhibit (a)(1)(C) NOTICE OF GUARANTEED DELIVERY OF WARRANTS OF DIRECT DIGITAL HOLDINGS, INC.

August 29, 2023 EX-99.(A)(1)(D)

Form of Letter to Brokers, Dealers, Commercial Banks, Trust Companies and Other Nominees, dated August 29, 2023.

Exhibit (a)(1)(D) Offer to Purchase Warrants to Acquire Shares of Class A Common Stock of Direct Digital Holdings, Inc.

August 11, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE QUARTERLY PERIOD ENDED JUNE 30, 2023 OR ☐ TRANSITION REPORT PURSUANT SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 001-41

August 10, 2023 8-K

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): August 10, 2023 Direct Digital Ho

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): August 10, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Comm

August 10, 2023 EX-99.1

Direct Digital Holdings Reports Second Quarter 2023 Financial Results Second Quarter 2023 Revenue Up 67% Year-Over-Year to $35.4 Million Company Raises Full-Year 2023 Revenue Guidance Due to Strong Q2 Results

Exhibit 99.1 Direct Digital Holdings Reports Second Quarter 2023 Financial Results Second Quarter 2023 Revenue Up 67% Year-Over-Year to $35.4 Million Company Raises Full-Year 2023 Revenue Guidance Due to Strong Q2 Results Houston, August 10, 2023 - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct Digital Holdings" or the "Company"), a leading advertising and marketing technology platform oper

July 12, 2023 EX-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.

Exhibit 10.1 Execution Version CREDIT AGREEMENT by and among DIRECT DIGITAL HOLDINGS, INC. DIRECT DIGITAL HOLDINGS, LLC COLOSSUS MEDIA, LLC HUDDLED MASSES LLC ORANGE142, LLC and EAST WEST BANK Dated as of July 7, 2023 TABLE OF CONTENTS Page Article I. DEFINITIONS 1 1.01 Definitions 1 1.02 Accounting Matters 19 1.03 Other Definitional Provisions 19 Article II. ADVANCES 19 2.01 Advances 19 2.02 Gene

July 12, 2023 8-K

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): July 7, 2023 Direct Digital Holdi

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): July 7, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commiss

June 12, 2023 8-K

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): June 12, 2023 Direct Digital Hold

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): June 12, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commis

June 6, 2023 EX-10.1

Early Opt-in Election, dated June 1, 2023, by and among Direct Digital Holdings, Inc., Direct Digital Holdings, LLC, Huddled Masses LLC, Colossus Media, LLC, Orange142, LLC, Lafayette Square Loan Servicing, LLC and Lafayette Square USA, Inc.

Exhibit 10.1 Lafayette Square Loan Servicing, LLC PO Box 25250 PMB 13941 Miami, Florida 33102-5250 June 1, 2023 Lafayette Square USA, Inc. PO Box 25250 PMB 13941 Miami, Florida 33102-5250 Attention: Susan Golden Email: [email protected] [email protected] Re: Early Opt-in Election Ladies and Gentlemen: Reference hereby is made to that certain Term Loan and Security Agreement, da

June 6, 2023 8-K

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): June 5, 2023 Direct Digital Holdi

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): June 5, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commiss

May 15, 2023 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE QUARTERLY PERIOD ENDED MARCH 31, 2023 OR ☐ TRANSITION REPORT PURSUANT SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 001-4

May 11, 2023 EX-99.1

Direct Digital Holdings Reports First Quarter 2023 Financial Results First Quarter 2023 Revenue Up 87% Year-Over-Year to $21.2 Million

Exhibit 99.1 Direct Digital Holdings Reports First Quarter 2023 Financial Results First Quarter 2023 Revenue Up 87% Year-Over-Year to $21.2 Million Houston, May 11, 2023 - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct Digital Holdings" or the "Company"), a leading advertising and marketing technology platform operating through its companies Colossus Media, LLC ("Colossus SSP"), Huddled Mas

May 11, 2023 8-K

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): May 11, 2023 Direct Digital Holdi

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): May 11, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commiss

May 9, 2023 8-K

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): April 20, 2023 Direct Digital Hol

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): April 20, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commi

May 4, 2023 424B3

CLASS A COMMON STOCK PREFERRED STOCK DEBT SECURITIES

Filed Pursuant to Rule 424(b)(3) Registration No. 333-271382 PROSPECTUS $300,000,000 CLASS A COMMON STOCK PREFERRED STOCK DEBT SECURITIES WARRANTS UNITS This prospectus will allow us to issue, from time to time at prices and on terms to be determined at or prior to the time of the offering, up to $300 million in aggregate principal amount of our Class A common stock, preferred stock, debt securiti

May 2, 2023 CORRESP

Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310, Houston, Texas 77207

Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310, Houston, Texas 77207 VIA EDGAR May 3, 2023 Securities and Exchange Commission Division of Corporation Finance Office of Trade & Services 100 F Street, N.E. Washington, D.C. 20549 Attn: Taylor Beech Re: Direct Digital Holdings, Inc. Registration Statement on Form S-3 (File. No. 333-271382) Request for Acceleration of Effective Date Lad

May 1, 2023 DEFA14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Ame

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A (RULE 14a-101) INFORMATION REQUIRED IN PROXY STATEMENT SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confide

May 1, 2023 DEF 14A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ____)

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A INFORMATION Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant. x Filed by a Party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e

April 21, 2023 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-3 (Form Type) Direct Digital Holdings, Inc.

April 21, 2023 S-3

As filed with the Securities and Exchange Commission on April 21, 2023

As filed with the Securities and Exchange Commission on April 21, 2023 Registration No.

April 21, 2023 EX-4.8

Form of subordinated indenture.

Exhibit 4.8 DIRECT DIGITAL HOLDINGS, INC. and Trustee INDENTURE Dated as of                                  SUBORDINATED DEBT SECURITIES CROSS-REFERENCE TABLE(1) Section of Trust Indenture Act of 1939, as amended Section of Indenture 310(a) 6.09 310(b) 6.08 6.10 310(c) Inapplicable 311(a) 6.13 311(b) 6.13 311(c) Inapplicable 312(a) 4.01 4.04 312(b) 4.04(c) 312(c) 4.04(c) 313(a) 4.03 313(b) 4.03 3

April 21, 2023 EX-4.7

Form of senior indenture.

Exhibit 4.7 DIRECT DIGITAL HOLDINGS, INC. and Trustee INDENTURE Dated as of SENIOR DEBT SECURITIES CROSS-REFERENCE TABLE(1) Section of Trust Indenture Act of 1939, as amended Section of Indenture 310(a) 6.09 310(b) 6.08 6.10 310(c) Inapplicable 311(a) 6.13 311(b) 6.13 311(c) Inapplicable 312(a) 4.01 4.04 312(b) 4.04(c) 312(c) 4.04(c) 313(a) 4.03 313(b) 4.03 313(c) 4.03 313(d) 4.03 314(a) 3.05 and

April 18, 2023 424B3

2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants

Prospectus Supplement No. 5 (to Prospectus dated February 10, 2022) Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-261059 2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants This prospectus supplement updates and supplements the prospectus dated February 10, 2022 (the “Prospectus”), which forms a part of our Registration Statement on Form S-1. This prospectus

April 18, 2023 POS EX

As filed with the Securities and Exchange Commission on April 18, 2023

As filed with the Securities and Exchange Commission on April 18, 2023 Registration No.

April 17, 2023 EX-4.4

Description of the Registrant’s Securities

Exhibit 4.4 DESCRIPTION OF THE REGISTRANT’S SECURITIES REGISTERED PURSUANT TO SECTION 12 OF THE SECURITIES EXCHANGE ACT OF 1934 The “Company,” “Direct Digital,” “Direct Digital Holdings,” “DDH,” “we,” “us” and “our” refer to Direct Digital Holdings, Inc. The following description summarizes the material terms and provisions of the registered securities of Direct Digital Holdings, Inc. Because it i

April 17, 2023 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K (Mark One) ☒ ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE FISCAL YEAR ENDED DECEMBER 31, 2022 OR ☐ TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 001-412

March 31, 2023 NT 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 12b-25 NOTIFICATION OF LATE FILING (Check one): x Form 10-K ¨ Form 20-F ¨ Form 11-K ¨ Form 10-Q ¨ Form 10-D ¨ Form N-SAR ¨ Form N-CSR For Period Ended: December 31, 2022 ¨ Transition Report on Form 10-K ¨ Transition Report on Form 20-F ¨ Transition Report on Form 11-K ¨ Transition Report on Form 10-Q ¨ Transition Report o

March 31, 2023 EX-99.1

March 31, 2023

Exhibit 99.1 March 31, 2023 Board of Directors Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310 Houston, Texas 77027 Ladies and Gentlemen: Pursuant to Rule 12b-25 of the General Rules and Regulations under the Securities Exchange Act of 1934, as amended, we inform you that we have been furnished a copy of Form 12b-25, to be filed by Direct Digital Holdings, Inc. on or about March 31,

March 23, 2023 8-K

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): March 23, 2023 Direct Digital Hol

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): March 23, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Commi

March 23, 2023 8-K/A

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): March 23, 2023 Direct Digital H

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): March 23, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Com

March 23, 2023 EX-99.1

Correction: Direct Digital Holdings Reports Fourth Quarter & Full-Year 2022 Financial Results Full-Year 2022 Revenue Up 131% Year-Over-Year to $88.0 Million Fourth Quarter 2022 Revenue Up 128% to $29.4 Million

Exhibit 99.1 In the news release, Direct Digital Holdings Reports Fourth Quarter & Full-Year 2022 Financial Results, issued 23-Mar-2023 by Direct Digital Holdings over PR Newswire, we are advised by the company that for the year ended December 31, 2022, Net income per common unit for both Basic and Diluted shares should be $0.23, not $0.17 and Weighted-average common units outstanding for both Bas

March 23, 2023 EX-99.1

Direct Digital Holdings Reports Fourth Quarter & Full-Year 2022 Financial Results Full-Year 2022 Revenue Up 131% Year-Over-Year to $88.0 Million Fourth Quarter 2022 Revenue Up 128% to $29.4 Million

Exhibit 99.1 Direct Digital Holdings Reports Fourth Quarter & Full-Year 2022 Financial Results Full-Year 2022 Revenue Up 131% Year-Over-Year to $88.0 Million Fourth Quarter 2022 Revenue Up 128% to $29.4 Million Houston, March 23, 2023 - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct Digital Holdings" or the "Company"), a leading advertising and marketing technology platform operating throug

March 13, 2023 8-K

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): March 13, 2023 Direct Digital Hol

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): March 13, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Commi

February 8, 2023 SC 13G/A

US25461T1051 / DIRECT DIGITAL-A / Direct Digital Management, LLC - SC 13G/A Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)* Direct Digital Holdings, Inc. (Name of Issuer) CLASS A COMMON STOCK, PAR VALUE $0.001 PER SHARE (Title of Class of Securities) 25461T105 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to

January 18, 2023 EX-99.1

Direct Digital Holdings Appoints Misty Locke, Former Global Chief Marketing Officer for Dentsu Media, to Board of Directors Brings More than 20 Years of Deep Advertising Industry Insights and Expertise to the Company

Exhibit 99.1 Direct Digital Holdings Appoints Misty Locke, Former Global Chief Marketing Officer for Dentsu Media, to Board of Directors Brings More than 20 Years of Deep Advertising Industry Insights and Expertise to the Company HOUSTON – January 18, 2023 – Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direct Digital Holdings" or the "Company"), a leading advertising and marketing technology pla

January 18, 2023 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

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): January 16, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 87-2306185 (State or other jurisdiction of incorporation) (Com

January 12, 2023 SC 13G/A

US25461T1051 / DIRECT DIGITAL-A / Empery Asset Management, LP - DIRECT DIGITAL HOLDINGS, INC. Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. 1)* Direct Digital Holdings, Inc. (Name of Issuer) Common Stock, par value $0.001 (Title of Class of Securities) 25461T105 (CUSIP Number) December 31, 2022 (Date of event which requires filing of this statement) Check the appropriate box to designate the rule pursuant to

January 11, 2023 EX-10.2

Third Amendment to Term Loan and Security Agreement, dated January 9, 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.

Exhibit 10.2 Execution Version THIRD AMENDMENT TO term loan and security AGREEMENT This Third Amendment to Term Loan and Security Agreement (“Amendment”), dated effective as of January 9, 2023 (the “Effective Date”), is entered into by and between Direct Digital Holdings, LLC, a Texas limited liability company (“Borrower”), Direct Digital Holdings, Inc., a Delaware corporation (“DDH Holdings”), Co

January 11, 2023 8-K

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): January 9, 2023 Direct Digital Ho

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): January 9, 2023 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Comm

January 11, 2023 EX-10.1

Loan and Security Agreement, dated effective as of January 9, 2023, by and among Direct Digital Holdings, LLC, Colossus Media, LLC, Huddled Masses LLC, Orange142, LLC, and Direct Digital Holdings, Inc., as borrowers, and Silicon Valley Bank, as lender.

Exhibit 10.1 LOAN AND SECURITY AGREEMENT This LOAN AND SECURITY AGREEMENT (this “Agreement”) is dated as of the Effective Date between SILICON VALLEY BANK, a California corporation (“Bank”), and the borrowers listed on Schedule I hereto (collectively, “Borrower”). The parties agree as follows: 1. LOAN AND TERMS OF PAYMENT 1.1 Revolving Line. (a) Availability. Subject to the terms and conditions of

November 15, 2022 EX-10.1

Exclusive License and Sale Agreement, effective as of November 9, 2022, by and between Colossus Media, LLC and SmartyAds, Inc.

Exhibit 10.1 EXCLUSIVE LICENSE AND SALE AGREEMENT This Agreement is effective as of November 9, 2022 (the “Effective Date”) by and between Colossus Media, LLC , a limited liability company organized under the laws of the State of Delaware having its principal address at 1233 West Loop South, Houston, Texas 77055 (hereinafter referred to as “Licensee” and “Buyer”) and SMARTYADS, INC., a Delaware bu

November 15, 2022 8-K

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): November 9, 2022 Direct Digital H

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): November 9, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Com

November 14, 2022 EX-10.2

Second Redemption Agreement, dated as of July 28, 2022, by and between Direct Digital Holdings, LLC and USDM Holdings, Inc.

Exhibit 10.2 Execution Version Second Amendment to Redemption Agreement THIS SECOND AMENDMENT TO REDEMPTION AGREEMENT (this “Amendment”) is made and entered into as of July 28, 2022 by and between Direct Digital Holdings, LLC, a Delaware limited liability company (the “Company”), and USDM Holdings, Inc., a Texas corporation (“Seller”), and is an amendment to the Redemption Agreement entered into b

November 14, 2022 424B3

2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants

Table of Contents ? ? ? ? Prospectus Supplement No. 4 (to Prospectus dated February 10, 2022) Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-261059 2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants This prospectus supplement updates and supplements the prospectus dated February 10, 2022 (the ?Prospectus?), which forms a part of our Registration Statement on

November 14, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q (Mark One) ☒ QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE QUARTERLY PERIOD ENDED SEPTEMBER 30, 2022 OR ☐ TRANSITION REPORT PURSUANT SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 0

November 14, 2022 EX-10.1

Second Amendment and Joinder to Term Loan and Security Agreement, dated effective as of July 28, 2022, by and among Direct Digital Holdings, LLC, as borrower, Colossus Media, LLC, Huddled Masses LLC, Orange142, LLC, Universal Standards for Digital Marketing, LLC and Direct Digital Holdings, Inc., as guarantors, Lafayette Square Loan Servicing, LLC as administrative agent, and the various financial institutions signatory to the Term Loan and Security Agreement as lenders.

Exhibit 10.1 EXECUTION VERSION SECOND AMENDMENT AND JOINDER TO TERM LOAN AND SECURITY AGREEMENT This Second Amendment and Joinder to Term Loan and Security Agreement (“Amendment”), dated effective as of July 28, 2022 (the “Effective Date”), is entered into by and between Direct Digital Holdings, LLC, a Texas limited liability company (“Borrower”), Colossus Media, LLC, a Delaware limited liability

November 10, 2022 8-K

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): November 10, 2022 Direct Digital

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): November 10, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Co

November 10, 2022 EX-99.1

Direct Digital Holdings Reports Third Quarter 2022 Financial Results Third Quarter 2022 Revenue Up 211% Year-Over-Year to $26.0 Million Third Quarter Net Income Up Year-Over-Year to $0.8 Million, or $0.06 per Share Company Raises Revenue Guidance to

Exhibit 99.1 Direct Digital Holdings Reports Third Quarter 2022 Financial Results Third Quarter 2022 Revenue Up 211% Year-Over-Year to $26.0 Million Third Quarter Net Income Up Year-Over-Year to $0.8 Million, or $0.06 per Share Company Raises Revenue Guidance to $85 Million-$90 Million for Full-Year 2022 Houston, November 10, 2022 /PRNewswire/ - Direct Digital Holdings, Inc. (Nasdaq: DRCT) ("Direc

November 3, 2022 8-K

Termination of a Material Definitive Agreement

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): July 26, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Commis

August 17, 2022 8-K

Other Events

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): August 16, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Comm

August 16, 2022 424B3

2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants

Prospectus Supplement No. 3 (to Prospectus dated February 10, 2022) Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-261059 2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants This prospectus supplement updates and supplements the prospectus dated February 10, 2022 (the ?Prospectus?), which forms a part of our Registration Statement on Form S-1. This prospectus

August 15, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

August 12, 2022 SC 13G

US25461T1051 / DIRECT DIGITAL-A / Direct Digital Management, LLC - SC 13G Passive Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. )* Direct Digital Holdings, Inc. (Name of Issuer) CLASS A COMMON STOCK, PAR VALUE $0.001 PER SHARE (Title of Class of Securities) 25461T105 (CUSIP Number) August 10, 2022 (Date of Event Which Requires Filing of this Statement) Check the appropriate box to de

August 11, 2022 EX-99.1

Direct Digital Holdings Reports Second Quarter 2022 Financial Results Second Quarter 2022 Revenue Up 90% Year-Over-Year to $21.3 Million Second Quarter Net Income Up 58% Year-Over-Year to $2.6 Million, or $0.18 per Share Company Raises Guidance to $7

EX-99.1 2 tm2223155d1ex99-1.htm EXHIBIT 99.1 Exhibit 99.1 Direct Digital Holdings Reports Second Quarter 2022 Financial Results Second Quarter 2022 Revenue Up 90% Year-Over-Year to $21.3 Million Second Quarter Net Income Up 58% Year-Over-Year to $2.6 Million, or $0.18 per Share Company Raises Guidance to $70 Million-$75 Million for Full-Year 2022 Houston, August 11, 2022 /PRNewswire/ - Direct Digi

August 11, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): August 11, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Comm

August 3, 2022 EX-10.2

Second Redemption Agreement, dated as of July 28, 2022, by and between Direct Digital Holdings, LLC and USDM Holdings, Inc.

Exhibit 10.2 Execution Version Second Amendment to Redemption Agreement THIS SECOND AMENDMENT TO REDEMPTION AGREEMENT (this ?Amendment?) is made and entered into as of July 28, 2022 by and between Direct Digital Holdings, LLC, a Delaware limited liability company (the ?Company?), and USDM Holdings, Inc., a Texas corporation (?Seller?), and is an amendment to the Redemption Agreement entered into b

August 3, 2022 8-K

Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

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): July 28, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Commis

August 3, 2022 EX-10.1

Second Amendment and Joinder to Term Loan and Security Agreement, dated effective as of July 28, 2022, by and among Direct Digital Holdings, LLC, as borrower, Colossus Media, LLC, Huddled Masses LLC, Orange142, LLC, Universal Standards for Digital Marketing, LLC and Direct Digital Holdings, Inc., as guarantors, Lafayette Square Loan Servicing, LLC as administrative agent, and the various financial institutions signatory to the Term Loan and Security Agreement as lenders.

EX-10.1 2 tm2222315d1ex10-1.htm EXHIBIT 10.1 Exhibit 10.1 EXECUTION VERSION SECOND AMENDMENT AND JOINDER TO TERM LOAN AND SECURITY AGREEMENT This Second Amendment and Joinder to Term Loan and Security Agreement (“Amendment”), dated effective as of July 28, 2022 (the “Effective Date”), is entered into by and between Direct Digital Holdings, LLC, a Texas limited liability company (“Borrower”), Colos

June 21, 2022 8-K/A

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K/A Amendment No. 1 CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 10, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of inco

June 13, 2022 EX-10.2

Form of Direct Digital Holdings, Inc. Employee Nonqualified Stock Option Award Agreement

Exhibit 10.2 DIRECT DIGITAL HOLDINGS, INC. EMPLOYEE NONQUALIFIED STOCK OPTION AWARD AGREEMENT THIS NONQUALIFIED STOCK OPTION AWARD AGREEMENT (this ?Agreement?), dated as of [], 2022 (the ?Date of Grant?), is made by and between Direct Digital Holdings, Inc. (the ?Company?), and [] (the ?Participant?). 1. Grant of Option. (a) Grant. The Company hereby grants to the Participant an Option to purchase

June 13, 2022 8-K

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

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): June 10, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Commis

June 13, 2022 EX-10.3

Form of Direct Digital Holdings, Inc. Director Restricted Stock Unit Award Agreement

Exhibit 10.3 DIRECT DIGITAL HOLDINGS, INC. DIRECTOR RESTRICTED STOCK UNIT AWARD AGREEMENT This Restricted Stock Unit Award Agreement (this ?Agreement?), dated as of [], 2022 (the ?Date of Grant?), is made by and between Direct Digital Holdings, Inc. (the ?Company?), and [] (the ?Director?). 1. Grant of Restricted Stock Units. (a) Award Grant. The Company hereby grants to the Director a total of []

June 13, 2022 EX-10.1

Form of Direct Digital Holdings, Inc. Employee Restricted Stock Unit Award Agreement

Exhibit 10.1 DIRECT DIGITAL HOLDINGS, INC. EMPLOYEE RESTRICTED STOCK UNIT AWARD AGREEMENT This Restricted Stock Unit Award Agreement (this ?Agreement?), dated as of [], 2022 (the ?Date of Grant?), is made by and between Direct Digital Holdings, Inc. (the ?Company?), and [] (the ?Participant?). 1. Grant of Restricted Stock Units. (a) Grant. The Company hereby grants to the Participant a total of []

May 26, 2022 8-K

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing

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): May 20, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Commiss

May 17, 2022 424B3

2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants

Prospectus Supplement No. 2 (to Prospectus dated February 10, 2022) Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-261059 2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants This prospectus supplement updates and supplements the prospectus dated February 10, 2022 (the ?Prospectus?), which forms a part of our Registration Statement on Form S-1. This prospectus

May 16, 2022 10-Q

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-Q

Table of Contents ? UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.

May 12, 2022 EX-99.1

Direct Digital Holdings Reports First Quarter 2022 Financial Results First Quarter 2022 Revenue Up 100% Year-Over-Year to $11.4 Million

Exhibit 99.1 Direct Digital Holdings Reports First Quarter 2022 Financial Results First Quarter 2022 Revenue Up 100% Year-Over-Year to $11.4 Million Houston, May 12, 2022 - Direct Digital Holdings, Inc. (Nasdaq: DRCT) (“Direct Digital”), a leading advertising and marketing technology platform, announced financial results for the first quarter ended March 31, 2022. Chairman and Chief Executive Offi

May 12, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): May 12, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Commiss

April 8, 2022 POS EX

As filed with the Securities and Exchange Commission on April 8, 2022

As filed with the Securities and Exchange Commission on April 8, 2022 Registration No.

April 8, 2022 S-8

As filed with the Securities and Exchange Commission on April 8, 2022

As filed with the Securities and Exchange Commission on April 8, 2022 Registration No.

April 8, 2022 EX-FILING FEES

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) Direct Digital Holdings, Inc.

April 1, 2022 424B3

2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants

Prospectus Supplement No. 1 (to Prospectus dated February 10, 2022) Filed Pursuant to Rule 424(b)(3) Registration Statement No. 333-261059 2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants This prospectus supplement updates and supplements the prospectus dated February 10, 2022 (the ?Prospectus?), which forms a part of our Registration Statement on Form S-1. This prospectus

March 31, 2022 EX-10.11

Executive Employment Agreement, dated as of February 15, 2022, by and between Direct Digital Holdings, LLC and Keith Smith.

Exhibit 10.11 Executive Employment Agreement This EXECUTIVE EMPLOYMENT AGREEMENT (?Agreement?) is made by and between Direct Digital Holdings, LLC, a Texas limited liability company (together with its successors and assigns, the ?Company?), and Keith Smith (?Executive?). This Agreement shall be effective upon the consummation of the Company?s initial public offering (the ?Effective Date?). RECITAL

March 31, 2022 EX-10.16

First Amendment to Term Loan and Security Agreement, dated as of February 3, 2022, by and among Direct Digital Holdings, LLC, as borrower, Colossus Media, LLC, Huddled Masses LLC, Orange142, LLC, and Universal Standards for Digital Marketing, LLC, as guarantors, Lafayette Square Loan Servicing, LLC as administrative agent, and the various financial institutions signatory to the Term Loan and Security Agreement as lenders.

Exhibit 10.16 Execution Version FIRST AMENDMENT TO term loan and security AGREEMENT This First Amendment to Term Loan and Security Agreement (?Amendment?), dated effective as of February 3, 2022 (the ?Effective Date?), is entered into by and between Direct Digital Holdings, LLC, a Texas limited liability company (?Borrower?), Colossus Media, LLC, a Delaware limited liability company (?Colossus?),

March 31, 2022 EX-10.12

Executive Employment Agreement, dated as of February 15, 2022, by and between Direct Digital Holdings, LLC and Susan Echard.

Exhibit 10.12 Executive Employment Agreement This EXECUTIVE EMPLOYMENT AGREEMENT (?Agreement?) is made by and between Direct Digital Holdings, LLC, a Texas limited liability company (together with its successors and assigns, the ?Company?), and Susan Echard (?Executive?). This Agreement shall be effective upon the consummation of the Company?s initial public offering (the ?Effective Date?). RECITA

March 31, 2022 EX-10.10

Executive Employment Agreement, dated as of February 15, 2022, by and between Direct Digital Holdings, LLC and Mark Walker.

Exhibit 10.10 Executive Employment Agreement This EXECUTIVE EMPLOYMENT AGREEMENT (?Agreement?) is made by and between Direct Digital Holdings, LLC, a Texas limited liability company (together with its successors and assigns, the ?Company?), and Mark Walker (?Executive?). This Agreement shall be effective upon the consummation of the Company?s initial public offering (the ?Effective Date?). RECITAL

March 31, 2022 EX-10.13

Executive Employment Agreement, dated as of March 9, 2022, by and between Direct Digital Holdings, LLC and Anu Pillai.

Exhibit 10.13 Executive Employment Agreement This EXECUTIVE EMPLOYMENT AGREEMENT (?Agreement?) is made by and between Direct Digital Holdings, LLC, a Texas limited liability company (together with its successors and assigns, the ?Company?), and Anu Pillai (?Executive?). This Agreement shall be effective upon the consummation of the Company?s initial public offering (the ?Effective Date?). RECITALS

March 31, 2022 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, D.C. 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE FISCAL YEAR ENDED DECEMBER 31, 2021 OR ? TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 FOR THE TRANSITION PERIOD FROM TO COMMISSION FILE NUMBER 001-41261 DIRECT DIGITAL

March 31, 2022 EX-10.19

Second Amendment to Credit Agreement, dated as of February 10, 2022, by and among Direct Digital Holdings, LLC, Colossus Media, LLC, Huddled Masses LLC, Orange142, LLC, Universal Standards for Digital Marketing, LLC and East West Bank.

Exhibit 10.19 Execution Version second AMENDMENT TO credit AGREEMENT This Second Amendment to Credit Agreement (?Amendment?), dated effective as of February 10, 2022 (the ?Effective Date?), is entered into by and between Direct Digital Holdings, LLC, a Texas limited liability company (?DDH?), Colossus Media, LLC, a Delaware limited liability company (?Colossus?), Huddled Masses LLC, a Delaware lim

March 29, 2022 8-K

Financial Statements and Exhibits, Results of Operations and Financial Condition

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): March 29, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Commi

March 29, 2022 EX-99.1

Direct Digital Holdings Reports Fourth Quarter & Full Year 2021 Financial Results Full Year 2021 Revenue Up 206% Year-Over-Year to $38.1 Million, with Fourth Quarter 2021 Revenue Up 95%

EX-99.1 2 tm2210468d1ex99-1.htm EXHIBIT 99.1 Exhibit 99.1 Direct Digital Holdings Reports Fourth Quarter & Full Year 2021 Financial Results Full Year 2021 Revenue Up 206% Year-Over-Year to $38.1 Million, with Fourth Quarter 2021 Revenue Up 95% Houston, March 29, 2022 - Direct Digital Holdings, Inc. (Nasdaq: DRCT) (“Direct Digital”), a leading advertising and marketing technology holding group, ann

March 18, 2022 SC 13G

DRCT / Direct Digital Holdings Inc Class A / Empery Asset Management, LP - DIRECT DIGITAL HOLDINGS, INC. Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G Under the Securities Exchange Act of 1934 (Amendment No. )* Direct Digital Holdings, Inc. (Name of Issuer) Common Stock, par value $0.001 (Title of Class of Securities) 25461T105 (CUSIP Number) February 10, 2022 (Date of event which requires filing of this statement) Check the appropriate box to designate the rule pursuant to w

February 16, 2022 EX-4.2

Unit Purchase Option, dated February 15, 2022, issued by the Company to Roth Capital Partners, LLC

Exhibit 4.2 UNIT PURCHASE OPTION THE REGISTERED HOLDER OF THIS UNIT PURCHASE OPTION BY ITS ACCEPTANCE HEREOF, AGREES THAT THE SECURITIES EVIDENCED BY THIS UNIT PURCHASE OPTION MAY NOT BE SOLD, TRANSFERRED OR ASSIGNED EXCEPT AS HEREIN PROVIDED AND THE REGISTERED HOLDER OF THIS UNIT PURCHASE OPTION AGREES THAT THE SECURITIES EVIDENCED BY THIS UNIT PURCHASE OPTION WILL NOT BE SOLD, TRANSFERRED, ASSIG

February 16, 2022 EX-4.3

Warrant Agent Agreement, dated February 15, 2022, by and between the Company and American Stock Transfer & Trust Company, LLC

Exhibit 4.3 WARRANT AGENT AGREEMENT This Warrant Agent Agreement (?Warrant Agreement?) is made as of February 15, 2022, by and among Direct Digital Holdings, Inc., a Delaware corporation, with offices at 1233 West Loop South, Suite 1170, Houston, TX 77027 (the ?Company?), and American Stock Transfer & Trust Company, LLC, a New York limited liability trust company (the ?Warrant Agent?). WHEREAS, th

February 16, 2022 EX-10.1

Second Amended and Restated Limited Liability Company Agreement of Direct Digital Holdings, LLC, dated as of February 15, 2022

Exhibit 10.1 SECOND AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT OF Direct Digital Holdings, LLC (a Texas limited liability company) February 15, 2022 THE UNITS REPRESENTED BY THIS AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT HAVE NOT BEEN REGISTERED UNDER THE UNITED STATES SECURITIES ACT OF 1933, AS AMENDED, OR UNDER ANY OTHER APPLICABLE SECURITIES LAWS. SUCH UNITS MAY NOT

February 16, 2022 8-K

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Entry into a Material Definitive Agreement, Financial Statements and Exhibits, Other Events

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): February 10, 2022 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) Delaware 001-41261 83-0662116 (State or other jurisdiction of incorporation) (Co

February 16, 2022 EX-1.1

Underwriting Agreement, dated February 10, 2022, by and among the Company, The Benchmark Company, LLC and Roth Capital Partners, LLC, as representatives of the underwriters

Exhibit 1.1 Direct Digital Holdings, Inc. UNDERWRITING AGREEMENT February 10, 2022 The Benchmark Company, LLC ROTH CAPITAL PARTNERS, LLC ???As Representatives of the several ???Underwriters named in Schedule I hereto c/o The Benchmark Company, LLC 150 East 58th Street, 17th Floor New York, New York 10155 c/o Roth Capital Partners, LLC 888 San Clemente Drive, Suite 400 Newport Beach, CA 92660 Ladie

February 16, 2022 EX-4.1

Unit Purchase Option, dated February 15, 2022, issued by the Company to The Benchmark Company, LLC

Exhibit 4.1 UNIT PURCHASE OPTION THE REGISTERED HOLDER OF THIS UNIT PURCHASE OPTION BY ITS ACCEPTANCE HEREOF, AGREES THAT THE SECURITIES EVIDENCED BY THIS UNIT PURCHASE OPTION MAY NOT BE SOLD, TRANSFERRED OR ASSIGNED EXCEPT AS HEREIN PROVIDED AND THE REGISTERED HOLDER OF THIS UNIT PURCHASE OPTION AGREES THAT THE SECURITIES EVIDENCED BY THIS UNIT PURCHASE OPTION WILL NOT BE SOLD, TRANSFERRED, ASSIG

February 16, 2022 EX-10.2

Tax Receivable Agreement, dated February 15, 2022, by and among the Company, Direct Digital Holdings, LLC and Direct Digital Management, LLC

Exhibit 10.2 Tax Receivable Agreement between DIRECT DIGITAL HOLDINGS, Inc. and THE PERSONS NAMED HEREIN Dated as of February 15, 2022 TABLE OF CONTENTS TAX RECEIVABLE AGREEMENT 1 RECITALS???????? 1 ARTICLE I Definitions 2 1.1 Definitions 2 Article II Determination of Certain Realized Tax Benefits 10 2.1 Basis Schedule 10 2.2 Tax Benefit Schedule 11 2.3 Procedures, Amendments 12 2.4 Basis Adjustme

February 16, 2022 EX-99.1

DIRECT DIGITAL HOLDINGS PRICES INITIAL PUBLIC OFFERING

Exhibit 99.1 DIRECT DIGITAL HOLDINGS PRICES INITIAL PUBLIC OFFERING HOUSTON, TX (February 10, 2022) ? Direct Digital Holdings, Inc. (Nasdaq: DRCT) (?Direct Digital?), a leading advertising and marketing technology holding group, today announced the pricing of its underwritten initial public offering of 2,800,000 units, each consisting of one share of Class A common stock and one warrant to purchas

February 16, 2022 EX-3.1

Amended and Restated Certificate of Incorporation of Direct Digital Holdings, Inc.

Exhibit 3.1 AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF DIRECT DIGITAL HOLDINGS, INC. Direct Digital Holdings, Inc., a Delaware corporation, hereby certifies that: ONE: The name of this corporation is Direct Digital Holdings, Inc. This corporation filed its original Certificate of Incorporation with the Secretary of State of the State of Delaware on August 23, 2021. TWO: The board of dire

February 16, 2022 EX-3.2

Amended and Restated Bylaws of Direct Digital Holdings, Inc.

Exhibit 3.2 AMENDED AND RESTATED BYLAWS OF DIRECT DIGITAL HOLDINGS, INC. (A DELAWARE CORPORATION) As adopted by the Board of Directors on January 17, 2022 and effective as of February 15, 2022 Table of Contents Page ARTICLE I OFFICES 3 Section 1. Registered Office 3 Section 2. Other Offices 3 ARTICLE II CORPORATE SEAL 3 Section 3. Corporate Seal 3 ARTICLE III STOCKHOLDERS? MEETINGS 3 Section 4. Pl

February 14, 2022 424B4

2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants

TABLE OF CONTENTS ?Filed Pursuant to Rule 424(b)(4) ?Registration Statement No. 333-261059? PROSPECTUS 2,800,000 Units Consisting of Shares of Class A Common Stock and Warrants This is an initial public offering of units, each unit consisting of one share of our Class A common stock and one warrant to purchase one share of our Class A common stock. The shares of Class A common stock and warrants a

February 8, 2022 CORRESP

[Signature Page Follows]

February 8, 2022 VIA EDGAR TRANSMISSION Division of Corporation Finance United States Securities and Exchange Commission 100 F Street, N.

February 8, 2022 CORRESP

February 8, 2022

February 8, 2022 VIA EDGAR TRANSMISSION United States Securities and Exchange Commission Division of Corporation Finance Office of Technology 100 F Street, N.

February 7, 2022 EX-FILING FEES

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-1/A (Form Type) Direct Digital Holdings, Inc.

February 7, 2022 S-1/A

As filed with the Securities and Exchange Commission on February 7, 2022

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on February 7, 2022 Registration No.

February 7, 2022 CORRESP

***

VIA EDGAR February 7, 2022 U.S. Securities and Exchange Commission Division of Corporation Finance Office of Technology 100 F Street, N.E. Washington, D.C. 20549 Attn: Ms. Claire DeLabar Mr. Robert Littlepage Mr. Austin Pattan Ms. Kathleen Krebs Re: Direct Digital Holdings, Inc. Amendment No. 3 to the Registration Statement on Form S-1 Filed January 31, 2022 File No. 333-261059 On behalf of our cl

February 3, 2022 8-A12B

Form 8-A filed February 3, 2022

8-A12B 1 tm2125950d208a12b.htm 8-A12B UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-A FOR REGISTRATION OF CERTAIN CLASSES OF SECURITIES PURSUANT TO SECTION 12(b) OR 12(g) OF THE SECURITIES EXCHANGE ACT OF 1934 DIRECT DIGITAL HOLDINGS, INC. (Exact name of registrant as specified in its charter) Delaware 83-0662116 (State of Incorporation or Organization) (I.R.S. Emp

February 3, 2022 CORRESP

[Signature Page Follows]

February 3, 2022 VIA EDGAR TRANSMISSION Division of Corporation Finance United States Securities and Exchange Commission 100 F Street, N.

February 3, 2022 CORRESP

February 3, 2022

February 3, 2022 VIA EDGAR TRANSMISSION United States Securities and Exchange Commission Division of Corporation Finance Office of Technology 100 F Street, N.

February 2, 2022 CORRESP

[Signature Page Follows]

February 2, 2022 VIA EDGAR TRANSMISSION Division of Corporation Finance United States Securities and Exchange Commission 100 F Street, N.

February 2, 2022 S-1/A

As filed with the Securities and Exchange Commission on February 2, 2022

? As filed with the Securities and Exchange Commission on February 2, 2022 Registration No.

February 2, 2022 CORRESP

February 2, 2022

February 2, 2022 VIA EDGAR TRANSMISSION United States Securities and Exchange Commission Division of Corporation Finance Office of Technology 100 F Street, N.

February 2, 2022 EX-4.3

Form of Warrant included in the units offered hereby (included in Exhibit 4.3).

Exhibit 4.3 WARRANT AGENT AGREEMENT This Warrant Agent Agreement (“Warrant Agreement”) is made as of February [], 2022, by and among Direct Digital Holdings, Inc., a Delaware corporation, with offices at 1233 West Loop South, Suite 1170, Houston, TX 77027 (the “Company”), and American Stock Transfer & Trust Company, LLC, a New York limited liability trust company (the “Warrant Agent”). WHEREAS, th

January 31, 2022 EX-4.3

Form of Warrant included in the units offered hereby (included in Exhibit 4.3).

EX-4.3 3 tm2125950d16ex4-3.htm EXHIBIT 4.3 Exhibit 4.3 WARRANT AGENT AGREEMENT This Warrant Agent Agreement (“Warrant Agreement”) is made as of February [], 2022, by and among Direct Digital Holdings, Inc., a Delaware corporation, with offices at 1233 West Loop South, Suite 1170, Houston, TX 77027 (the “Company”), and American Stock Transfer & Trust Company, LLC, a New York limited liability trust

January 31, 2022 S-1/A

As filed with the Securities and Exchange Commission on January 31, 2022

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on January 31, 2022 Registration No.

January 31, 2022 EX-1.1

Form of Unit Purchase Option (included in Exhibit 1.1).

Exhibit 1.1 Direct Digital Holdings, Inc. UNDERWRITING AGREEMENT [•], 2022 The Benchmark Company, LLC ROTH CAPITAL PARTNERS, LLC As Representatives of the several Underwriters named in Schedule I hereto c/o The Benchmark Company, LLC 150 East 58th Street, 17th Floor New York, New York 10155 c/o Roth Capital Partners, LLC 888 San Clemente Drive, Suite 400 Newport Beach, CA 92660 Ladies and Gentleme

January 24, 2022 S-1/A

As filed with the Securities and Exchange Commission on January 24, 2022

As filed with the Securities and Exchange Commission on January 24, 2022 Registration No.

January 24, 2022 EX-1.1

Form of Representatives’ Warrant (included in Exhibit 1.1)

Exhibit 1.1 [•] Shares1 Direct Digital Holdings, Inc. Class A Common Stock, par value $0.001 per share UNDERWRITING AGREEMENT [•], 2022 The Benchmark Company, LLC ROTH CAPITAL PARTNERS, LLC As Representatives of the several Underwriters named in Schedule I hereto c/o The Benchmark Company, LLC 150 East 58th Street, 17th Floor New York, New York 10155 c/o Roth Capital Partners, LLC 888 San Clemente

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