REGISTRATION RIGHTS AGREEMENTRegistration Rights Agreement • October 21st, 2024 • Direct Digital Holdings, Inc. • Services-advertising
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 individually as a “Party” and collectively as the “Parties.”
Tax Receivable Agreement between DIRECT DIGITAL HOLDINGS, Inc. and THE PERSONS NAMED HEREIN Dated as of February 15, 2022Tax Receivable Agreement • February 16th, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc. • Delaware
This TAX RECEIVABLE AGREEMENT (this “Agreement”), is dated as of February 15, 2022, and is between Direct Digital Holdings, Inc., a Delaware corporation, each of the undersigned parties, and each of the other persons from time to time that becomes a party hereto (each, excluding the Corporate Taxpayer and OpCo (each as defined below), a “TRA Party” and together the “TRA Parties”).
LOAN AND SECURITY AGREEMENTLoan and Security Agreement • January 11th, 2023 • Direct Digital Holdings, Inc. • Services-advertising
WARRANT AGENT AGREEMENTWarrant Agent Agreement • February 16th, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc. • New York
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”).
EXECUTIVE EMPLOYMENT AGREEMENTExecutive Employment Agreement • October 15th, 2024 • Direct Digital Holdings, Inc. • Services-advertising • Texas
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 agreed by the parties (the “Effective Date”).
SECOND AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT OF Direct Digital Holdings, LLC (a Texas limited liability company) January [--], 2022Limited Liability Company Agreement • January 24th, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc. • Texas
This SECOND AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT (the “Agreement”) of Direct Digital Holdings, LLC, a Texas limited liability company (the “Company”), dated as of January [__], 2022, by and among the Company, Direct Digital Holdings, Inc., a Delaware corporation (“PubCo”), and each of the Members listed on the signature pages hereto, and is made effective as of the Effective Time. Capitalized terms used herein without definition shall have the meanings assigned to such terms in Appendix A.
THIRD AMENDMENT TO CREDIT AGREEMENTCredit Agreement • November 13th, 2024 • Direct Digital Holdings, Inc. • Services-advertising • Texas
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., a Delaware corporation (“DDH Holdings”), Direct Digital Holdings, LLC, a Texas limited liability company (“Direct Digital”), Colossus Media, LLC, a Delaware limited liability company (“Colossus”), Huddled Masses LLC, a Delaware limited liability company (“HM”), Orange142, LLC, a Delaware limited liability company (“Orange” and together with DDH Holdings, Direct Digital, Colossus and HM, “Borrowers” and each individually a “Borrower”), and East West Bank, a California state bank (“Lender”).
•] Shares1 Direct Digital Holdings, Inc. Class A Common Stock, par value $0.001 per share UNDERWRITING AGREEMENTUnderwriting Agreement • January 24th, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc. • New York
Direct Digital Holdings, Inc., a Delaware corporation (the “Company”), proposes, subject to the terms and conditions stated herein, to sell to the several Underwriters named in Schedule I hereto (the “Underwriters”) an aggregate of [•] shares (the “Firm Shares”) of Class A common stock, par value $0.001 per share (the “Common Stock”), of the Company. The Firm Shares consist of authorized but unissued shares of Common Stock to be issued and sold by the Company. The Company also proposes to grant to the several Underwriters an option to purchase up to [•] additional shares of Common Stock on the terms and for the purposes set forth in Section 3(b) hereof (the “Option Shares”). The Firm Shares and any Option Shares purchased pursuant to this Underwriting Agreement (this “Agreement”) are herein collectively called the “Securities.”
Second Amendment to Redemption AgreementRedemption Agreement • August 3rd, 2022 • Direct Digital Holdings, Inc. • Services-advertising • Texas
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 by such parties as of November 14, 2021, as amended by that certain Amendment to Redemption Agreement dated as of February 15, 2022 (the “First Amendment”) (as so amended, the “Original Redemption Agreement”, and the Original Redemption Agreement, as amended by this Amendment, is referred to herein as the “Redemption Agreement”). The Company and Seller are referred to herein each as a “Party” and collectively as the “Parties.” Capitalized terms used but not defined herein shall have the meanings assigned to such terms in the Redemption Agreement.
SHARE PURCHASE AGREEMENTShare Purchase Agreement • October 21st, 2024 • Direct Digital Holdings, Inc. • Services-advertising • New York
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 “Party” and collectively as the “Parties.”
THIRD AMENDMENT TO term loan and security AGREEMENTTerm Loan and Security Agreement • January 11th, 2023 • Direct Digital Holdings, Inc. • Services-advertising
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”), Colossus Media, LLC, a Delaware limited liability company (“Colossus”), Huddled Masses LLC, a Delaware limited liability company (“HM”), Orange142, LLC, a Delaware limited liability company (“Orange” and together with DDH Holdings, Colossus, and HM, “Guarantors” and each individually a “Guarantor” and together with Borrower, collectively, the “Credit Parties”, and each a “Credit Party”), Lafayette Square Loan Servicing, LLC, as agent for the Lenders (“Agent”), and the Lenders party hereto.
Direct Digital Holdings, Inc. UNDERWRITING AGREEMENTUnderwriting Agreement • February 16th, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc. • New York
Direct Digital Holdings, Inc., a Delaware corporation (the “Company”), proposes, subject to the terms and conditions stated herein, to sell to the several Underwriters named in Schedule I hereto (the “Underwriters”) an aggregate of 2,800,000 units (the “Firm Units”), consisting of (i) an aggregate of 2,800,000 shares (the “Firm Shares”) of Class A common stock, par value $0.001 per share (the “Common Stock”), of the Company, and (ii) warrants exercisable to purchase an aggregate of 2,800,000 shares of Common Stock (the “Firm Warrants”), which Warrants shall have an exercise price of $5.50, subject to adjustment as provided therein (the “Warrants”). The Firm Shares and the Common Stock issuable upon the exercise of the Warrants (the “Warrant Shares”) consist of authorized but unissued shares of Common Stock to be issued and sold by the Company. The Company also proposes to grant to the several Underwriters an option to purchase up to 420,000 additional shares of Common Stock (the “Optio
DIRECT DIGITAL HOLDINGS, INC. EMPLOYEE NONQUALIFIED STOCK OPTION AWARD AGREEMENTEmployee Nonqualified Stock Option Award Agreement • June 13th, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc. • Delaware
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”).
DIRECT DIGITAL HOLDINGS, INC. EMPLOYEE RESTRICTED STOCK UNIT AWARD AGREEMENTEmployee Restricted Stock Unit Award Agreement • June 13th, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc. • Delaware
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”).
Direct Digital Holdings, Inc. UNDERWRITING AGREEMENTUnderwriting Agreement • January 31st, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc. • New York
Direct Digital Holdings, Inc., a Delaware corporation (the “Company”), proposes, subject to the terms and conditions stated herein, to sell to the several Underwriters named in Schedule I hereto (the “Underwriters”) an aggregate of [•] units (the “Firm Units”), consisting of (i) an aggregate of [•] shares (the “Firm Shares”) of Class A common stock, par value $0.001 per share (the “Common Stock”), of the Company, and (ii) warrants exercisable to purchase an aggregate of [•] shares of Common Stock (the “Firm Warrants”), which Warrants shall have an exercise price of $[•], subject to adjustment as provided therein (the “Warrants”). The Firm Shares and the Common Stock issuable upon the exercise of the Warrants (the “Warrant Shares”) consist of authorized but unissued shares of Common Stock to be issued and sold by the Company. The Company also proposes to grant to the several Underwriters an option to purchase up to [•] additional shares of Common Stock (the “Option Shares”) and/or Warra
DIRECT DIGITAL HOLDINGS, INC. DIRECTOR RESTRICTED STOCK UNIT AWARD AGREEMENTRestricted Stock Unit Award Agreement • June 13th, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc. • Delaware
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”).
second AMENDMENT TO credit AGREEMENTCredit Agreement • March 31st, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc. • Texas
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 limited liability company (“HM”), Orange142, LLC, a Delaware limited liability company (“Orange”) and Universal Standards for Digital Marketing, LLC, a Delaware limited liability company (“USDM” and together with DDH, Colossus, HM, and Orange, “Borrowers” and each individually a “Borrower”), and East West Bank, a California state bank (“Lender”).
AMENDMENT TO WARRANT AGREEMENTWarrant Agreement • October 24th, 2023 • Direct Digital Holdings, Inc. • Services-advertising • New York
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 amendment to that certain Warrant Agreement, dated as of February 15, 2022 (the “Existing Warrant Agreement”), between the Company and the Warrant Agent. Capitalized terms used but not otherwise defined in this Amendment shall have the meanings given to such terms in the Existing Warrant Agreement.
Second AMENDMENT TO CREDIT AGREEMENTCredit Agreement • November 30th, 2023 • Direct Digital Holdings, Inc. • Services-advertising • Texas
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 company (“Colossus”), Huddled Masses LLC, a Delaware limited liability company (“HM”), Orange142, LLC, a Delaware limited liability company (“Orange” and together with DDH Holdings, Direct Digital, Colossus and HM, “Borrowers” and each individually a “Borrower”), and East West Bank, a California state bank (“Lender”).
FIRST AMENDMENT TO term loan and security AGREEMENTTerm Loan and Security Agreement • March 31st, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc.
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”), Huddled Masses LLC, a Delaware limited liability company (“HM”), Orange142, LLC, a Delaware limited liability company (“Orange”) and Universal Standards for Digital Marketing, LLC, a Delaware limited liability company (“USDM” and together with Colossus, HM, and Orange, “Guarantors” and each individually a “Guarantor”), and Lafayette Square Loan Servicing, LLC, as agent for the Lenders (“Agent”).
FOURTH AMENDMENT TO TERM LOAN AND SECURITY AGREEMENTTerm Loan and Security Agreement • October 10th, 2023 • Direct Digital Holdings, Inc. • Services-advertising
Term Loan and Security Agreement dated as of December 3, 2021 among DIRECT DIGITAL HOLDINGS, LLC, a Texas limited liability company (“DDH”, together with any Person joined as a party to this Agreement as a “Borrower” in accordance with Section 6.12 hereof, and all of their respective permitted successors and assigns, the “Borrowers”), the Guarantors party hereto (together with the Borrowers, the “Credit Parties” and each a “Credit Party”), the financial institutions which are now or which hereafter become a party hereto (collectively, the “Lenders” and each individually, a “Lender”) and Lafayette Square Loan Servicing, LLC (“Lafayette Square”), as agent for Lenders (Lafayette Square, in such capacity, “Agent”).
SECOND AMENDMENT AND JOINDER TO TERM LOAN AND SECURITY AGREEMENTTerm Loan and Security Agreement • August 3rd, 2022 • Direct Digital Holdings, Inc. • Services-advertising
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 company (“Colossus”), Huddled Masses LLC, a Delaware limited liability company (“HM”), Orange142, LLC, a Delaware limited liability company (“Orange”) and Universal Standards for Digital Marketing, LLC, a Delaware limited liability company (“USDM” and together with Colossus, HM, and Orange, “Existing Guarantors” and each individually an “Existing Guarantor”), Direct Digital Holdings, Inc., a Delaware corporation (“Joining Guarantor” and together with the Existing Guarantors, collectively, the “Guarantors”, and each a “Guarantor” and together with Borrower, collectively, the “Credit Parties”, and each a “Credit Party”), Lafayette Square Loan Servicing, LLC, as agent for the Lenders (“Agen
SECOND AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT OF Direct Digital Holdings, LLC (a Texas limited liability company) February 15, 2022Limited Liability Company Agreement • February 16th, 2022 • Direct Digital Holdings, Inc. • Services-computer programming, data processing, etc. • Texas
This SECOND AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT (the “Agreement”) of Direct Digital Holdings, LLC, a Texas limited liability company (the “Company”), dated as of February 15, 2022, by and among the Company, Direct Digital Holdings, Inc., a Delaware corporation (“PubCo”), and each of the Members listed on the signature pages hereto, and is made effective as of the Effective Time. Capitalized terms used herein without definition shall have the meanings assigned to such terms in Appendix A.
Lafayette Square Loan Servicing, LLC PO Box 25250 PMB 13941 Miami, Florida 33102-5250Term Loan and Security Agreement • June 6th, 2023 • Direct Digital Holdings, Inc. • Services-advertising
Reference hereby is made to that certain Term Loan and Security Agreement, dated as of December 3, 2021 (as amended, restated, supplemented or otherwise modified from time to time, the “Loan Agreement”), by and between DIRECT DIGITAL HOLDINGS, LLC, a Texas limited liability company (“Borrower”), DIRECT DIGITAL HOLDINGS, INC., a Delaware corporation (“DDH Holdings”), COLOSSUS MEDIA, LLC, a Delaware limited liability company (“Colossus”), HUDDLED MASSES, LLC, a Delaware liability company (“HM”), ORANGE142, LLC, a Delaware limited liability company (“Orange” and together with DDH Holdings, Colossus, HM, and Orange, the “Guarantors” and each individually a “Guarantor” and together with Borrower, collectively the, “Loan Parties”, and each a “Loan Party”), the financial institutions which are now or which hereafter become a party thereto (collectively, the “Lenders” and each individually, a “Lender”) and Lafayette Square Loan Servicing, LLC (“Lafayette Square”), as agent for Lenders (Lafayet
