Preferred Equity Subordination Agreement, entered into as of September 30, 2020, among East West Bank, USDM Holdings, Inc., and Direct Digital Holdings, LLC

Exhibit 10.6

PREFERRED EQUITY SUBORDINATION AGREEMENT

THIS PREFERRED EQUITY SUBORDINATION AGREEMENT (this “Subordination Agreement”) is entered into as of September 30, 2020, among EAST WEST BANK, a California state bank (“Senior Lender”), USDM HOLDINGS, INC., a Texas corporation (“Preferred Unit Holder”), and DIRECT DIGITAL HOLDINGS, LLC, a Texas limited liability company (the “Company”).

R E C I T A L S

A.           The Company desires that Senior Lender extend credit to the Company and certain of its affiliates, on a revolving basis as set forth in the Credit Agreement (as defined herein) and has entered into a Security Agreement in favor of Senior Lender in connection therewith. The Company and Preferred Unit Holder have entered into that certain Amended and Restated Limited Liability Company Agreement dated as of September 30, 2020 (the “Company Agreement”).

B.           It is the agreement of the parties that the payment obligations owed by the Company to Preferred Unit Holder shall be subordinate to the indebtedness owed by the Borrowers (as defined below) to Senior Lender, all as hereafter provided.

NOW, THEREFORE, for good and valuable consideration, the receipt, sufficiency and adequacy which are hereby acknowledged, the parties hereto agree as follows:

1.             Definitions. The following terms shall have the respective meanings specified below or in the Section or Recital referred to below:

“Bankruptcy Proceeding” means any proceeding by or against any party for relief under any bankruptcy, reorganization or insolvency law or laws relating to the relief of debtors, or any receivership, insolvency or assignment for the benefit of creditors, or any proceeding for any liquidation, liquidating distribution, dissolution or other winding up of such party, voluntary or involuntary, whether or not involving insolvency or bankruptcy proceedings.

“Credit Agreement” means that certain Credit Agreement by and among the Company, 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 Standard for Digital Marketing, LLC, a Delaware limited liability company (“USDM” and together with the Company, Colossus, HM, and Orange, “Borrowers” and each individually a “Borrower”), and Senior Lender dated of even date herewith, as amended, restated, supplemented or otherwise modified from time to time.

“Enforcement Action” means any judicial, arbitral or other proceeding, or any collection or enforcement action of any kind, to enforce or attempt to enforce any right or remedy available to Preferred Unit Holder to collect the Junior Obligations, including any judicial, arbitral or proceeding or any collection action against the Company or the Company’s assets seeking, directly or indirectly, to enforce any rights or remedies, or to enforce any of the obligations incurred by the Company, under or in connection with the Junior Obligations (but excluding demand notices and other similar notices); provided, however, that (1) the imposition of surcharges as contemplated by Sections 3.1, 8.8, 8.9, or 8.10 of the Company Agreement, (2) the submission to mediation or arbitration as contemplated by Sections 8.8, 8.9, 8.10 or Section 12.16 of the Company Agreement and/or (3) specific performance, injunctive or other equitable relief as contemplated by Sections 8.11 or 12.16 of the Company Agreement (but still subject to Section 3 hereof) shall not be an “Enforcement Action” hereunder.

“Junior Obligations” means the obligation of Company to pay distributions of available cash, to allocate profits, to redeem preferred units, or make any other payments to Preferred Unit Holder in accordance with Sections 3.1, 4.1, 8.8, and 8.9 of the Company Agreement.

“Loan Documents” has the meaning given such term in the Credit Agreement.

“Obligated Party” has the meaning given such term in the Credit Agreement.

“Senior Debt” has the meaning given such term in Section 2 herein.

“Subordination Event” means the occurrence and continuance of an Event of Default (as defined in the Credit Agreement).

2.           Subordination. The Junior Obligations shall be subordinate and junior in right of payment and collection to the payment and collection in full of all present and future indebtedness, obligations and liabilities of the Borrowers and the other Obligated Parties to Senior Lender under the Loan Documents (the “Senior Debt”).

3.            Limitations on Distributions, Payments and Redemption. Except as is hereinafter set forth in this Section 3, no payment shall be made by or on behalf of the Company on account of or for application against the Junior Obligations, whether as a result of setoff, realization upon collateral or otherwise, and no distribution (other than Permitted Tax Distributions as defined in the Credit Agreement and Tax Distributions as defined in the Term Loan Agreement) of any kind shall be received by Preferred Unit Holder from the Company, and no redemption shall be made by Preferred Unit Holder any of the Preferred Units (as defined in the Company Agreement) until the Senior Debt shall have been fully paid in cash and satisfied (other than contingent indemnification obligations as to which no claim has been asserted). The provisions of the first sentence of this Section 3 notwithstanding, for so long as (i) no Subordination Event shall have occurred and be continuing and (ii) after giving effect to the payment or distribution with respect to the Preferred Units or the redemption of the Preferred Units, the Borrowers would be in pro forma compliance with the financial covenants set forth in Article IX of the Credit Agreement, the Company may make payments or distributions to the Preferred Unit Holder permitted by the Company Agreement and the Company may pay the Preferred Unit Holder and the Preferred Unit Holder may receive the distributions and redemption price set forth in the Company Agreement with respect to such Preferred Units (the “Permitted Payments”). Upon the occurrence and during the continuation of a Subordination Event, all further payments of Permitted Payments to Preferred Unit Holder shall immediately cease; provided, that such Permitted Payments may continue to accrue and at such time as there shall be no continuing Subordination Event such accrued Permitted Payments may be paid in full and payments of Permitted Payments may resume hereunder. Senior Lender shall use commercially reasonable efforts to provide Preferred Unit Holder with notice of the occurrence of a Subordination Event.

4.           Certain Distributions. Preferred Unit Holder agrees that in the event of any distribution, division or any application, partial or complete, voluntary or involuntary, by operation of law or otherwise, of all or any part of the assets of the Company or the proceeds thereof to creditors of the Company, in any case for reason of the liquidation, dissolution or winding up of the Company or the Company’s business, or in the event of any sale, receivership, insolvency or Bankruptcy Proceeding or assignment for the benefit of creditors, or any proceeding by or against the Company for any relief under any bankruptcy or insolvency law or laws relating to the relief of debtors, the adjustment of indebtedness, reorganizations, compositions or extensions, then and in any such event any payment or distribution of any kind or character, either in cash, property, securities or otherwise, which shall thereafter be paid or delivered by the Company upon or with respect to the Junior Obligations shall be turned over by Preferred Unit Holder to Senior Lender (without liability for interest thereon) for application on the Senior Debt, until the Senior Debt shall have been fully paid in cash and satisfied (other than contingent indemnification obligations as to which no claim has been asserted).

5.          Remedies Standstill. Unless Senior Lender otherwise consents in writing, Preferred Unit Holder will not commence any Enforcement Action prior to the earliest of:

(a)          the date all Senior Debt is fully paid in cash and satisfied (other than contingent indemnification obligations as to which no claim has been asserted); or

(b)          the occurrence of a Bankruptcy Proceeding involving the Company.

For the avoidance of doubt, nothing contain herein shall be deemed to limit Preferred Unit Holder’s ability to enforce or attempt to enforce any right or remedy available to Preferred Unit Holder under that certain Membership Interest Purchase and Contribution Agreement, dated on or about the date hereof, by and among Preferred Unit Holder, the Company, and Orange.

6.          Additional Agreements. Preferred Unit Holder agrees (a) that it will not commence or pursue in any action of any kind (including any Enforcement Action or Bankruptcy Proceeding) to prohibit, limit or impair the commencement or pursuit by Senior Lender of any of its rights or remedies under or in connection with the Senior Debt, the Credit Agreement, the Loan Documents, or otherwise available to Senior Lender under applicable law; (b) that Preferred Unit Holder will not assign or otherwise transfer the Junior Obligations unless such assignment is made expressly subject to this Subordination Agreement; and (c) not to amend in any material respects the terms of the payment of the Junior Obligations, or to increase the distribution or other payments constituting Junior Obligations without the consent of Senior Lender (other than the imposition of surcharges as contemplated by Sections 3.1, 8.8, 8.9, or 8.10 of the Company Agreement).

7.            Treatment of Payments. In the event that notwithstanding the provisions of this Subordination Agreement, any cash or distribution of assets of the Company, whether in cash, property, securities or otherwise, which, under the provisions of this Subordination Agreement should not have been paid to Preferred Unit Holder, is received by Preferred Unit Holder or any person on its behalf, or provision is made for such payment or distribution, such payment or distribution shall be held for the benefit of and shall immediately be paid or delivered directly to Senior Lender, with any necessary endorsement, for application to the payment of the Senior Debt; until the Senior Debt shall have been fully paid cash and satisfied (other than contingent indemnification obligations as to which no claim has been asserted); provided, however, the Senior Lender must provide written notice to the Preferred Unit Holder within 10 days of such distribution that such distribution must be returned.

8.          Modification to Senior Debt. Senior Lender may, at any time and from time to time, without the consent of or notice to Preferred Unit Holder, without incurring any responsibility to Preferred Unit Holder, and without impairing or releasing the obligations of Preferred Unit Holder to Senior Lender (a) change the manner, place or terms of payment of, or change or extend the time of payment of, or renew, alter or increase the Senior Debt; (b) extend, modify or amend any agreement or any other document related to the Senior Debt or the Senior Liens; (c) sell, exchange, release or otherwise deal with any property by whomsoever at any time pledged or mortgaged to secure or howsoever securing, any of the Senior Debt; (d) release anyone liable in any manner for the payment or collection of any of the Senior Debt, (e) exercise or refrain from exercising any rights against the Company, any Borrower or any other person; or (f) take or refrain from taking any other action whatsoever.

9.         No Impairment. The provisions of this Subordination Agreement are intended solely for the purpose of defining the relative rights of Preferred Unit Holder or any holder of the Junior Obligations, on one hand, and Senior Lender or any holder of the Senior Debt, on the other hand, and nothing contained in this Subordination Agreement is intended to or shall impair, as between the Company, other creditors, and Preferred Unit Holder or any holder of the Junior Obligations, all amounts due and payable in accordance with the Junior Obligations, or to affect the relative rights of Preferred Unit Holder or any holder of the Junior Obligations and creditors of the Company other than Senior Lender or holders of the Senior Debt, nor shall anything herein or therein prevent Preferred Unit Holder or any holders of the Junior Obligations from exercising all remedies against the Company otherwise permitted by applicable law, subject to the rights of Senior Lender under the provisions of this Subordination Agreement.

10.          Obligations Hereunder Not Affected. No action or inaction of Senior Lender or any other person, and no change of law or circumstances, shall release or diminish the obligations, liabilities, agreements or duties hereunder of Preferred Unit Holder or the Company, or affect this Subordination Agreement in any way or provide any party any recourse against Senior Lender.

11.         Specific Performance. Senior Lender is hereby authorized to demand specific performance of this Subordination Agreement at any time when any other party shall have failed to comply with any of the provisions of this Subordination Agreement applicable to it. The Company and Preferred Unit Holder hereby irrevocable waive any defense based upon the adequacy of a remedy at law which might be asserted as a bar to such remedy of specific performance and waive any requirement of the posting of any bond which might otherwise be required before such remedy of specific performance granted.

12.          Subrogation. No payment or distribution to Senior Lender pursuant to the provisions of this Subordination Agreement shall entitle Preferred Unit Holder to exercise any rights of subrogation in respect thereof until the Senior Debt shall have been paid in cash and satisfied in full (other than contingent indemnification obligations as to which no claim has been asserted) or the Senior Lender shall have consented in writing to the exercise of such rights. After the payment of the Senior Debt in cash in full (other than contingent indemnification obligations as to which no claim has been asserted) and provided no payments are voidable, Preferred Unit Holder shall be subrogated to the rights of Senior Lender to receive payments or distributions applicable to the Senior Debt to the extent the distributions otherwise payable to Preferred Unit Holder have been applied to the payment of the Senior Debt.

13.          Choice of Law. THIS SUBORDINATION AGREEMENT SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF TEXAS APPLICABLE TO AGREEMENTS MADE AND TO BE PERFORMED ENTIRELY WITHIN SUCH STATE.

14.          Representations. Preferred Unit Holder represents and warrants that it has full power and authority to execute this Subordination Agreement and that this Subordination Agreement constitutes the valid and binding obligation of Preferred Unit Holder enforceable in accordance with its terms, subject to applicable bankruptcy, insolvency and similar laws affecting creditors’ rights generally, concepts of reasonableness and general principles of equity, regardless of whether considered in a proceeding in equity or at law. Preferred Unit Holder represents and warrants that it has furnished Senior Lender with true and complete copies of all documents which evidence the Junior Obligations.

15.        Waivers and Amendments. Until the Senior Debt shall have been fully paid or satisfied, this Subordination Agreement may not be amended, waived, terminated or otherwise modified except with the consent of Senior Lender and Preferred Unit Holder.

16.         No Implied Waiver. Any delay in the exercise of or any failure to exercise any right or remedy of Senior Lender shall not be deemed a waiver of any such right or remedy.

17.         Binding Effect. This Subordination Agreement shall be binding upon the parties and their respective successors, transferees and assigns. Each reference in this Subordination Agreement to Preferred Unit Holder shall include any assignee or transferee of the Junior Obligations, and each reference in this Subordination Agreement to Senior Lender shall include any assignee or transferee of the Senior Debt and the Senior Liens.

18.          Invalid Provisions. If any term or provision of this Subordination Agreement shall be determined to be illegal or unenforceable, all other terms and provisions hereof shall nevertheless remain effective and shall be enforced to the fullest extent permitted by law.

19.          Further Assurances. Preferred Unit Holder and the Company further agree to execute such subordinations and other documents that may be reasonably requested by Senior Lender to more fully give effect to the provisions of this Subordination Agreement.

20.          Notices. All notices, requests, consents, demands and other communications required or permitted under this Subordination Agreement shall be in writing and, unless otherwise specifically provided in this Subordination Agreement, (i) shall be deemed sufficiently given or furnished (a) if delivered by a commercial messenger service regularly retaining receipts for such delivery, effective on the date of delivery by the commercial messenger service; (b) if sent by electronic mail, effective on the date of delivery if sent return receipt acknowledged; (c) if sent by registered or certified mail, return receipt requested, effective forty-eight (48) hours after deposit; (d) if sent by telephonic facsimile transmission with a copy sent by regular mail, effective on the date imprinted on the facsimile transmission form; or (e) if delivered by the air courier services known as FedEx, Express Mail, Airborne or Emory Air, effective upon delivery thereof to the courier, and (ii) shall be addressed to the parties as listed as follows:

Senior Lender’s address:

East West Bank

5001 Spring Valley Road; Suite 825W

Dallas, Texas 75244

Attention: Hamilton LaRoe

email: ***@***

Company’s address:

Direct Digital Holdings, LLC

1233 West Loop South

Suite 1170

Houston, Texas 77027

Attention: Keith W. Smith

Email: ***@***

Phone: 713 ###-###-####

Preferred Unit Holder’s address:

USDM Holdings, Inc

5729 Krause Lane, Unit #13

Austin, Texas 78738

Attention: Leah Woolford and Jeff Woolford

Email:     ***@***

***@***

with a copy (not constituting notice) to:

Fredrikson & Byron, P.A.

200 South Sixth Street, Suite 4000

Attention: Jessica D. Manivasager

Email: ***@***

21.          Costs and Expenses. The Company agrees to pay, upon demand to Senior Lender, all reasonable and documented out-of-pocket costs and expenses (including court costs and reasonable attorneys’ fees for one primary counsel) incurred by Senior Lender in the enforcement of this Subordination Agreement.

22.          Counterparts. This Subordination Agreement may be executed in any number of identical counterparts, each of which when so executed constitutes an original and all of which constitute, collectively, one agreement.

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IN WITNESS WHEREOF, this Subordination Agreement is executed as of the date first above written.

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Preferred Equity Subordination Agreement

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Preferred Equity Subordination Agreement

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Preferred Equity Subordination Agreement