SecProbe.io

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 Document Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310 Houston, Texas 77027   VIA EDGAR   May 26, 2026   Securities and Exchange Commission Division of Corporation Finance Office of Trade & Services 100 F Street, N.E. Washington, D.C. 20549   Re:      Direct Digital Holdings, Inc. Registration Statement on Form S-1 File No. 333-295414     Request for Acceleration of Effective Date   Ladies and Gentlemen: Pursuant to Rule 461 under the Securities Act of 1933, as amended, Direct Digital Holdings, Inc. (the “ Company ”) hereby requests that the Securities and Exchange Commission accelerate the effective date of the above-referenced Registration Statement on Form S-1, as amended (the “ Registration Statement ”) so that the Registration Statement will be declared effective as of 4:05 p.m. Eastern time on May 27, 2026, or as soon as practicable thereafter. The Company hereby authorizes Stephen Older and Andrew Terjesen, both of whom are attorneys at the Company’s outside legal counsel, McGuireWoods LLP, to orally modify or withdraw this request for acceleration. Once the Registration Statement has been declared effective, please orally confirm that event with Mr. Older at (212) 548-2122, or in his absence, Mr. Terjesen at (919) 835-5977.   Thank you for your assistance in this matter.                                          Very truly yours,                                              Direct Digital Holdings, Inc.                                              /s/ DIANA P. DIAZ                                      Name: Diana P. Diaz                              Title: Chief Financial Officer   cc (via email): Stephen Older and Andrew Terjesen, McGuireWoods LLP

May 6, 2026
Mark D. Walker
Chief Executive Officer
Direct Digital Holdings, Inc.
1177 West Loop South, Suite 1310
Houston, TX 77027
Re: Direct Digital Holdings, Inc.
Registration Statement on Form S-1
Filed April 29, 2026
File No. 333-295414
Dear Mark D. Walker:
 This is to advise you that we have not reviewed and will not review your registration
statement.
 Please refer to Rules 460 and 461 regarding requests for acceleration. We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
 Please contact Cheryl Brown at 202-551-3905 with any questions.
Sincerely,
Division of Corporation Finance
Office of Trade & Services
cc: Andrew J. Terjesen, Esq.

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 Document Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310 Houston, Texas 77027   VIA EDGAR   February 10, 2026   Securities and Exchange Commission Division of Corporation Finance Office of Trade & Services 100 F Street, N.E. Washington, D.C. 20549 Attention: Scott Anderegg   Re:      Direct Digital Holdings, Inc. Registration Statement on Form S-1 File No. 333-293201     Request for Acceleration of Effective Date   Dear Mr. Anderegg: Pursuant to Rule 461 under the Securities Act of 1933, as amended, Direct Digital Holdings, Inc. (the “ Company ”) hereby requests that the Securities and Exchange Commission (the “ Commission ”) accelerate the effective date of the above-referenced Registration Statement on Form S-1 (the “ Registration Statement ”) so that the Registration Statement will be declared effective as of 4:01 p.m. Eastern time on February 11, 2026, or as soon as practicable thereafter. The Company hereby authorizes Rakesh Gopalan or David S. Wolpa, both of whom are attorneys at the Company’s outside legal counsel, Troutman Pepper Locke LLP, to orally modify or withdraw this request for acceleration. Once the Registration Statement has been declared effective, please orally confirm that event with Mr. Gopalan at (704) 916-2374 or Mr. Wolpa at (704) 916-2375.   Thank you for your assistance in this matter.                                          Very truly yours,                                              Direct Digital Holdings, Inc.                                              /s/ DIANA P. DIAZ                                      Name: Diana P. Diaz                              Title: Chief Financial Officer   cc (via email):    Rakesh Gopalan and David Wolpa, Troutman Pepper Locke LLP

February 10, 2026
Mark Walker
Chief Executive Officer
Direct Digital Holdings, Inc.
1177 West Loop South, Suite 1310
Houston, Texas 77027
Re:Direct Digital Holdings, Inc.
Registration Statement on Form S-1
Filed February 4, 2026
File No. 333-293201
Dear Mark Walker:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration. We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Scott Anderegg at 202-551-3342 with any questions.
Sincerely,
Division of Corporation Finance
Office of Trade & Services
cc:Rakesh Gopalan

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 Document Direct Digital Holdings, Inc. 1177 West Loop South, Suite 1310 Houston, Texas 77027   VIA EDGAR   November 25, 2025   Securities and Exchange Commission Division of Corporation Finance Office of Trade & Services 100 F Street, N.E. Washington, D.C. 20549   Re:      Direct Digital Holdings, Inc. Registration Statement on Form S-1 File No. 333-291106     Request for Acceleration of Effective Date   Ladies and Gentlemen:   Pursuant to Rule 461 under the Securities Act of 1933, as amended, Direct Digital Holdings, Inc. (the “ Company ”) hereby requests that the Securities and Exchange Commission (the “ Commission ”) accelerate the effective date of the above-referenced Registration Statement on Form S-1 (the “ Registration Statement ”) so that the Registration Statement will be declared effective as of 4:01 p.m. Eastern time on November 26, 2025, or as soon as practicable thereafter. The Company hereby authorizes Rakesh Gopalan or David S. Wolpa, both of whom are attorneys at the Company’s outside legal counsel, Troutman Pepper Locke LLP, to orally modify or withdraw this request for acceleration.   Once the Registration Statement has been declared effective, please orally confirm that event with Mr. Gopalan at (704) 916-2374 or Mr. Wolpa at (704) 916-2375.   Thank you for your assistance in this matter.                                          Very truly yours,                                              Direct Digital Holdings, Inc.                                              /S/ DIANA P. DIAZ                                  Name: Diana P. Diaz                              Title: Chief Financial Officer   cc (via email):    Rakesh Gopalan and David Wolpa, Troutman Pepper Locke LLP

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Document

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

Ladies and Gentlemen:

Pursuant to Rule 461 under the Securities Act of 1933, as amended, Direct Digital Holdings, Inc. (the “Company”) hereby requests that the Securities and Exchange Commission (the “Commission”) accelerate the effective date of the above-referenced Registration Statement on Form S-1 (the “Registration Statement”) so that the Registration Statement will be declared effective as of 4:01 p.m. Eastern time on January 28, 2025, or as soon as practicable thereafter. The Company hereby authorizes Rakesh Gopalan or David S. Wolpa, both of whom are attorneys at the Company’s outside legal counsel, Troutman Pepper Locke LLP, to orally modify or withdraw this request for acceleration.

Once the Registration Statement has been declared effective, please orally confirm that event with Mr. Gopalan at (704) 916-2374 or Mr. Wolpa at (704) 916-2375.

Thank you for your assistance in this matter.

                                     Very truly yours,

                                     Direct Digital Holdings, Inc.

                                     /S/ DIANA DIAZ

                             Name: Diana Diaz

                             Title: Chief Financial Officer

cc (via email):    Rakesh Gopalan and David Wolpa, Troutman Pepper Locke LLP

January 27, 2025
Diana Diaz
Chief Financial Officer
Direct Digital Holdings, Inc.
1177 West Loop South, Suite 1310
Houston, Texas 77027
Re:Direct Digital Holdings, Inc.
Registration Statement on Form S-1
Filed January 17, 2025
File No. 333-284344
Dear Diana Diaz:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration. We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Rucha Pandit at 202-551-6022 with any questions.
Sincerely,
Division of Corporation Finance
Office of Trade & Services
cc:Rakesh Gopalan

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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

Ladies and Gentlemen:

Pursuant to Rule 461 under the Securities Act of 1933, as amended, Direct Digital Holdings, Inc. (the “Company”) hereby requests that the Securities and Exchange Commission (the “Commission”) accelerate the effective date of the above-referenced Registration Statement on Form S-1 (the “Registration Statement”) so that the Registration Statement will be declared effective as of 4:00 p.m. Eastern time on November 4, 2024, or as soon as practicable thereafter. The Company hereby authorizes Rakesh Gopalan or David S. Wolpa, both of whom are attorneys at the Company’s outside legal counsel, Troutman Pepper Hamilton Sanders LLP, to orally modify or withdraw this request for acceleration.

Once the Registration Statement has been declared effective, please orally confirm that event with Mr. Gopalan at (704) 916-2374 or Mr. Wolpa at (704) 916-2375.

Thank you for your assistance in this matter.

Very truly yours,

Direct Digital Holdings, Inc.

 /s/ Diana P. Diaz

Name: Diana Diaz

Title: Chief Financial Officer

cc (via email):     Rakesh Gopalan and David Wolpa, Troutman Pepper Hamilton Sanders LLP

October 30, 2024
Mark D. Walker
Chairman and Chief Executive Officer
Direct Digital Holdings, Inc.
1177 West Loop South, Suite 1310
Houston, TX 77027
Re:Direct Digital Holdings, Inc.
Registration Statement on Form S-1
Filed October 22, 2024
File No. 333-282762
Dear Mark D. Walker:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration. We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Kate Beukenkamp at 202-551-3861 with any questions.
Sincerely,
Division of Corporation Finance
Office of Trade & Services
cc:Rakesh Gopalan

United States securities and exchange commission logo
January 31, 2024
Mark Walker
Chief Executive Officer
Direct Digital Holdings, Inc.
1177 West Loop South ,Suite 1310
Houston, Texas 77027
Re:Direct Digital Holdings, Inc.
Form 10-K for Fiscal Year Ended December 31, 2022
Filed April 17, 2023
File No. 001-41261
Dear Mark Walker:
            We have completed our review of your filing. We remind you that the company and its
management are responsible for the accuracy and adequacy of their disclosures, notwithstanding
any review, comments, action or absence of action by the staff.
Sincerely,
Division of Corporation Finance
Office of Trade & Services
cc:       Diana Diaz

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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.E.

Washington, D.C. 20549

    Re:
    Direct Digital Holdings, Inc.

    Form 10-K for Fiscal Year Ended December 31, 2022

    Filed April 17, 2023

    File No. 001-41261

Amy
Geddes and Lyn Shenk:

We are writing to respond
to the comments provided by the Staff (the “Staff”) of the Division of Corporation Finance of the U.S. Securities and
Exchange Commission in your letter dated September 18, 2023 (the “Comment Letter”), relating to the Direct Digital
Holdings, Inc. (“we”, “Direct Digital”, or the “Company”) Annual Report on Form
10-K for the fiscal year ended December 31, 2022 (the “Form 10-K”).

In this response, we may refer
to the analysis of our position regarding principal vs agent provided in our response letter dated September 18, 2023 (“Initial
Response”). The Company continues to believe that its accounting treatment is appropriate and consistent with our facts and
circumstances including our contracts and manner of operations. However, we acknowledge that we can provide additional clarity and update
certain disclosures identified by the Company and the Staff.

For ease of review, we have
set forth below the numbered comment of the Comment Letter in bold type followed by the Company’s response thereto.

Form 10-K for Fiscal Year Ended
December 31, 2022

Notes to Consolidated Financial
Statements

Note 2 - Basis of Presentation and
Summary of Significant Accounting Policies, page 73

1.
We note your response to comment 2 with regard to buy-side advertising. You state you offer “managed advertising campaigns”
to advertisers through Huddled Masses and Orange142. Your Huddled Masses website states you offer web design, marketing/sales integration,
conversion rate optimization, analytics audits, creative/copy development, and media planning and buying. In addition, your response refers
to “consulting services.” Please clarify whether these offerings are components of “managed advertising campaigns”
or separate offerings. If separate offerings (or available as separate offerings), it appears that your revenue recognition accounting
policy should address measurement and recognition of each material offering type. Please advise.

    Amy Geddes and Lyn Shenk

Securities and Exchange Commission

November 14, 2023

Page 2

Response to Comment:

The Company’s
Initial Response provided the types of contracts utilized by the buy-side segment of the business, as requested. Larger customers with
multiple tactics will generally execute a Master Service Agreement (“MSA”) and/or Statement of Work (“SOW”). Each
digital media campaign, which is part of a broader managed advertising campaign (MSA or SOW), will also have a specific Insertion Order
(“IO”) that details the terms of the specific digital media campaign. The Company’s buy-side business offers 50+ tactics
for services to customers. Of the top 80% of revenue (for 18 customers), the average number of tactics used per customer is 13 with a
high of 30 and a low count of three. The customers who make up the lower 20% of revenue (99 customers) average four tactics with a high
of 11 and a low of 1 (14 customers). As demonstrated by this analysis, it is unusual to offer only one service to customers on the buy-side.
Further, the total revenue identified as “consulting” made up less than 1% of the buy-side revenue and less than 0.2% of total
revenue.

2.
Please tell us whether, and the extent to which, the buy-side business derives revenue from programmatic purchase of advertising
by advertisers not under a “managed advertising campaign.” In this regard, we note your disclosure on page 73 that you offer
your buy-side service on both a fully managed and self-serve basis. If so, please provide us with your principal versus agent assessment
for these transactions, including your consideration of the definition of control (ASC 606-10-25-25), how control is obtained (55-37A),
and, if evaluated, the indicators of control (55-39). Please also tell us relevant contractual terms (rights and obligations) between
you and both the end consumer (advertiser) and the other parties involved in providing the specified goods or services for these transactions.

Response to Comment:

As described
in response to comment 1, buy-side customers purchase multiple tactics, one of which may be the programmatic purchase of advertising.
The Company had at one time considered offering self-service advertising, however, all current programmatic advertising is sold on a fully
managed basis and the disclosure on page 73 of the Form 10-K is no longer consistent with our current practice. In response to the Staff’s
comment, in future filings the Company will modify its disclosure consistent with the following:

“… The Company offers its services
on a fully managed and a self-serve basis, which is recognized over time using the output method when the performance
obligation is fulfilled. ...The performance obligation is satisfied over time as the volume of impressions are delivered up to the contractual
maximum for fully managed revenue and the delivery of media inventory for self-serve revenue.”

3.
We note your response to comment 2 with regard to sell-side advertising. You state your contracts with publishers (i.e.,
suppliers):

 · provide you with “the right to sell” ads “in exchange for
a fixed rate for digital ad units sold.”

    Amy Geddes and Lyn Shenk

Securities and Exchange Commission

November 14, 2023

Page 3

 · you are required to pay the publisher “a fixed rate” for any ads
you sell and “that rate is unaffected by the price paid by the advertisers.”

The former
suggests your consideration does not vary based on the final price set in the marketplace while the latter suggests it does. In addition,
on page 51 of your annual report you state, “we pay publishers a fee, which is typically a percentage of the value of the ad impressions
monetized through our platform.” Please clarify how your consideration is determined and whether your use of the term “rate”
with regard to the amount you and the publisher retain means an absolute amount or a rate such as a percent of the auction price.

Response to Comment:

The Company
notes to the Staff that as used in the contexts described above, as well as certain other of the Company’s disclosures, “rate”
means a percent of the auction price. That rate does not change regardless of the auction price.

4.
With regard to sell-side business, you state you control the digital ad units before they are transferred to advertisers
because your contracts with publishers “permit [you] to sell the digital ad units” to advertisers. Please tell us why you
believe a right to sell provides you control based on the definition of control (ASC 606-10-25-25) and the explanation of how control
is obtained (55-37A). Please also tell us whether your right to sell is exclusive for the publishers you serve.

Response to Comment:

Our right
to sell digital ad units for our publishers is not exclusive, in that the publishers can sell their digital ad units to many different
trading partners. Even when a digital ad unit is assigned to the Company by the publisher, there are other parties who may have the opportunity
to offer the digital ad unit for auction. The Colossus SSP’s platform will evaluate the digital ad unit for its quality –
specifically to eliminate any invalid traffic. The platform will then combine this with more information, including context and other
features that make the digital ad unit more attractive and marketable. Multiple buyers may bid on the digital ad unit through the Company
or through other trading partners of the publisher. As specified in ASC 606-10-55-37A, if the reporting entity combines goods or services
into a combined output that forms a single performance obligation to the end consumer, the reporting entity is the principal for all of
the goods and services in that combined output. Based upon the activity of the Company, we believe this supports our control of the digital
ad units and our classification as principal. Further, if the digital ad unit is determined to be valid and purchased or used to display
a digital ad through the Company, then the Company is liable to pay the publisher for the display, regardless of whether the Company is
paid by the advertiser. As such, the Company is at risk, which further supports our belief that we control the digital ad units.

We also considered
the control scenarios described in ASC 606-10-55-333 related to meal vouchers. We believe that this scenario does not apply to us because:

 · As described within this response, the Colossus SSP combines the ad request from
the Publisher with other information into a combined offering that is then presented to customers of the Company. Further, the customer
does not interact directly with the Publisher.

    Amy Geddes and Lyn Shenk

Securities and Exchange Commission

November 14, 2023

Page 4

 · As described in the response to comment 6, the ad request is associated with a
specific time and a specific place where a digital ad unit can be displayed by the Publisher. The digital ad units exist before the transfer.

5.
With regard to the sell-side business, you state you are “responsible for fulfilling the promise to the customer”
and you “take responsibility for the acceptability of the digital ad units.” Please tell us what promise you are fulfilling
and explain how specifically you are primarily responsible for fulfillment. As part of your response, please tell us what your contracts
and other material (such as marketing) say about primary responsibility, whether you have discretion in selecting the supplier (i.e.,
publisher) for a requested ad placement, whether you are primarily responsible for the performance of the publisher, and any other analysis
relevant to the assessment of primary responsibility for fulfillment under 55-39a. Provide representative sell-side agreements with publishers
and advertisers if they may be helpful in illustrating relevant contract terms.

Response to Comment:

As detailed
in our Initial Response, the Company’s success is based on curating advertisers and increasing access to publishers with valuable
ad impressions as well as enhancing ad inventory quality. Our website and contracts specify certain obligations that we have with our
customers (advertisers) and suppliers (publishers).

Through the
operation of the Colossus SSP, the Company has discretion as to if or when we send a digital ad unit to a DSP, advertiser or agency to
consider for purchase.

The Company’s
Quality Guidelines for Creative (see Exhibit A for excerpts from the Company’s website) indicate that the Company will scan and
otherwise check all materials for compliance with quality guidelines, which benefits both our customers (advertisers) and suppliers (publishers).
Performing these tasks ensures that the digital ad units are of an acceptable quality.

The Company’s
standard Master Services Agreement for DSPs outlines a number of responsibilities for the Company including:

 · The Company (SSP) will customize and implement an online advertising exchange that
performs in accordance with specifications and allows the DSP (customer) to purchase deliverables (impression inventory delivered by SSP)
in near real time.

 · Bid requests are sent to the DSP by the SSP for bids on a Deliverable consistent
with the Company’s management of the exchange.

 · SSP provides reasonable instructions and support to DSP.

 · Impression and payment calculations are based upon the SSP’s measurements.

Each of these
items (operating the SSP, sending bid requests, providing support to the DSP (customer) and providing the impression and payment calculations)
are a component of the fulfillment activities performed by the Company.

    Amy Geddes and Lyn Shenk

Securities and Exchange Commission

November 14, 2023

Page 5

The Company’s
standard Publisher Master Services Agreement outlines a number of responsibilities for the Company including:

 · The Company and the Publisher agree that the Company buys advertising media (inventory
delivered by Publisher including impressions or other desired actions) and Publisher desires to sell and Company desires to purchase certain
Publisher products and services through Colossus SSP.

 · Colossus SSP means the supply side advertising platform owned and operated by the
Company that allows buyers to purchase, in real-time, impression inventory delivered by the Company.

 · Company will pay the Publisher revenue for advertising material actually delivered
by Publisher to each of Publisher’s Sites. To clarify, there is no sequential liability stated or intended in these agreements
 – nothing relieves the Company of its obligation in the event that the Advertiser does not pay the Company.

 · Approved monthly spend may be set by the Company in the Agreement as a spending
limit for which it will be liable for any calendar month.

 · Company may be responsible for calculation of statistics including impressions.
Note that this is our default contract provision. The Company does allow the Customer to utilize an ad server or their own systems to
validate volume statistics.

 · Company represents and warrants to Publisher that it shall use reasonable commercial
efforts to contractually bind its upstream Advertiser to ensure compliance with all obligations with regard to Advertising materials provided
by the Advertiser and to ensure that Company, Publisher and Advertisers comply with all applicable Data Protections Laws with regards
to end user’s data collection, tracking and processing.

A recent article
published about our industry (see Exhibit B) and quoting the Company on its obligations to its Publishers is consistent with our contracts
and manner of operations. It also highlights the differences between us and some of our counterparts in the industry. We present this
information to the Staff to demonstrate the consistency of our approach regarding our status as principal.

We believe
that the Company’s contracts, website and manner of operations all support the Company’s position that it is responsible for
fulfilling the promise of providing high quality digital ad units to the customer and that we take responsibility for the acceptability
of the digital ad units.

6.
With regard to the sell-side business, you state you “purchase” advertising inventory from publishers to sell
to advertisers. Please clarify whether the “purchase” and “sale” take place instantaneously at the time someone
loads a web or app page and you and other intermediaries find an advertiser desiring to place an ad for that individual. We note in your
response you state you do not have inventory risk and, on page 61 of your annual report, that your sell-side platform “allows publishers
to sell, in real time, ad impressions to buyers.” Therefore, please clarify whether you “purchase” the ad inventory
or instead facilitate its sale to the advertiser.

Response to Comment:

In response
to the Staff’s comment, the Company acknowledges that the disclosure on page 61 could be improved and clarified. In future filings
the Company will modify its disclosure consistent with the following:

“… The Company’s sell-side
platform allows publishers us to sell, in real time, ad impressions purchased
from our publishers to buyers.”

    Amy Geddes and Lyn Shenk

Securities and Exchange Commission

November 14, 2023

Page 6

As described
in the response to comment 5 and as stated in our contracts, the Company purchases the ad impressions from the publishers and sells them
to DSPs, advertisers and agencies.

For the Staff’s
information and assessment, we describe below the process for a digital ad unit that takes place within the Colossus SSP’s digital
technology:

 · The

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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.E.

Washington, D.C. 20549

 Re: Direct Digital Holdings, Inc.

	Form 10-K for Fiscal Year Ended December
31, 2022

	Filed April 17, 2023

	File No. 001-41261

Amy Geddes and Lyn Shenk:

Direct Digital Holdings, Inc.
(the “Company”) is sending this letter to confirm the extension of time to respond to the comment letter dated October
16, 2023 from the staff (the “Staff”) of the Securities and Exchange Commission’s Division of Corporation Finance
relating to the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2022. As per our counsel’s discussion
with Ms. Geddes on October 30, 2023, this letter confirms that the agreed deadline for the Company to file its written response to the
Staff’s comment letter is November 14, 2023. Please contact me at 832-402-1054 should you have any questions or concerns.

    Very truly yours,

    /s/ Diana P. Diaz

    Diana P. Diaz

    Chief Financial Officer

    cc (electronic):
    Mark Walker, Chairman & CEO

    Rakesh Gopalan, McGuireWoods LLP

United States securities and exchange commission logo
October 16, 2023
Mark Walker
Chief Executive Officer
Direct Digital Holdings, Inc.
1177 West Loop South ,Suite 1310
Houston, Texas 77027
Re:Direct Digital Holdings, Inc.
Form 10-K for Fiscal Year Ended December 31, 2022
Filed April 17, 2023
File No. 001-41261
Dear Mark Walker:
            We have reviewed your September 18. 2023 response to our comment letter and have the
following comments.
            Please respond to this letter within ten business days by providing the requested
information or advise us as soon as possible when you will respond. If you do not believe a
comment applies to your facts and circumstances, please tell us why in your response.
            After reviewing your response to this letter, we may have additional comments. Unless
we note otherwise, any references to prior comments are to comments in our August 17, 2023
letter.
Form 10-K for Fiscal Year Ended December 31, 2022
Notes to Consolidated Financial Statements
Note 2 - Basis of Presentation and Summary of Significant Accounting Policies, page 73
1.We note your response to comment 2 with regard to buy-side advertising. You state you
offer “managed advertising campaigns” to advertisers through Huddled Masses and
Orange142. Your Huddled Masses website states you offer web design, marketing/sales
integration, conversion rate optimization, analytics audits, creative/copy development, and
media planning and buying. In addition, your response refers to “consulting
services.” Please clarify whether these offerings are components of “managed advertising
campaigns” or separate offerings. If separate offerings (or available as separate offerings),
it appears that your revenue recognition accounting policy should address measurement
and recognition of each material offering type. Please advise.

 FirstName LastNameMark Walker
 Comapany NameDirect Digital Holdings, Inc.
 October 16, 2023 Page 2
 FirstName LastNameMark Walker
Direct Digital Holdings, Inc.
October 16, 2023
Page 2
2.Please tell us whether, and the extent to which, the buy-side business derives revenue
from programmatic purchase of advertising by advertisers not under a “managed
advertising campaign.” In this regard, we note your disclosure on page 73 that you offer
your buy-side service on both a fully managed and self-serve basis. If so, please provide
us with your principal versus agent assessment for these transactions, including your
consideration of the definition of control (ASC 606-10-25-25), how control is obtained
(55-37A), and, if evaluated, the indicators of control (55-39). Please also tell us relevant
contractual terms (rights and obligations) between you and both the end consumer
(advertiser) and the other parties involved in providing the specified goods or services for
these transactions.
3.We note your response to comment 2 with regard to sell-side advertising. You state your
contracts with publishers (i.e., suppliers):

•provide you with “the right to sell” ads “in exchange for a fixed rate for digital ad
units sold.”
•you are required to pay the publisher “a fixed rate” for any ads you sell and “that rate
is unaffected by the price paid by the advertisers.”

The former suggests your consideration does not vary based on the final price set in the
marketplace while the latter suggests it does. In addition, on page 51 of your annual report
you state, “we pay publishers a fee, which is typically a percentage of the value of the ad
impressions monetized through our platform.” Please clarify how your consideration is
determined and whether your use of the term “rate” with regard to the amount you and the
publisher retain means an absolute amount or a rate such as a percent of the auction price.
4.With regard to sell-side business, you state you control the digital ad units before they are
transferred to advertisers because your contracts with publishers “permit [you] to sell the
digital ad units” to advertisers. Please tell us why you believe a right to sell provides you
control based on the definition of control (ASC 606-10-25-25) and the explanation of how
control is obtained (55-37A). Please also tell us whether your right to sell is exclusive for
the publishers you serve.
5.With regard to the sell-side business, you state you are “responsible for fulfilling the
promise to the customer” and you “take responsibility for the acceptability of the digital
ad units.” Please tell us what promise you are fulfilling and explain how specifically you
are primarily responsible for fulfillment. As part of your response, please tell us what your
contracts and other material (such as marketing) say about primary responsibility, whether
you have discretion in selecting the supplier (i.e., publisher) for a requested ad placement,
whether you are primarily responsible for the performance of the publisher, and any other
analysis relevant to the assessment of primary responsibility for fulfillment under 55-
39a. Provide representative sell-side agreements with publishers and advertisers if they
may be helpful in illustrating relevant contract terms.
6.With regard to the sell-side business, you state you “purchase” advertising inventory from

 FirstName LastNameMark Walker
 Comapany NameDirect Digital Holdings, Inc.
 October 16, 2023 Page 3
 FirstName LastName
Mark Walker
Direct Digital Holdings, Inc.
October 16, 2023
Page 3
publishers to sell to advertisers. Please clarify whether the “purchase” and “sale” take
place instantaneously at the time someone loads a web or app page and you and other
intermediaries find an advertiser desiring to place an ad for that individual. We note in
your response you state you do not have inventory risk and, on page 61 of your annual
report, that your sell-side platform “allows publishers to sell, in real time, ad impressions
to buyers.” Therefore, please clarify whether you “purchase” the ad inventory or instead
facilitate its sale to the advertiser.
7.With regard to the sell-side business, you state you have discretion to establish minimum
prices. You also state you enter into master service agreements with publishers which,
among other terms, set a fixed rate for content to be sold on Colossus SSP. In this regard,
it appears that the minimum prices may be set by negotiation between you and publishers
and that you can sell ads on behalf of the publisher-customers so long as the minimum
price is obtained. Please confirm our understanding. In addition, because ads are sold
through bids at auction, actual prices appear to be set by the market. If minimum prices
are set by negotiation with publishers and final prices are ultimately set by the market,
please advise why you believe you have discretion in pricing under 55-39c.
8.You disclose on page 11 of your annual report, “We charge a standard fee to our
publishers for providing access to a host of media buyers on a daily basis.” This appears to
differ from transaction-based sell-side revenue generated by specific ad
placements. Please quantify this revenue for us.
9.Please tell us whether, and to what extent, you recognize revenue on transactions
involving both your buy-side and sell-side platforms and, if so, how you recognize
revenue on such transactions (principal versus agent).
            Please contact Amy Geddes at 202-551-3304 or Lyn Shenk at 202-551-3380 if you have
questions regarding comments on the financial statements and related matters.
Sincerely,
Division of Corporation Finance
Office of Trade & Services

CORRESP
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    McGuireWoods LLP

    1251 Avenue of the Americas

    20th Floor

    New York, NY 10020

VIA EDGAR AND EMAIL

September 21, 2023

U.S. Securities and Exchange Commission

Division of Corporation Finance

Office of Mergers & Acquisitions

100 F Street, N.E.

Washington, D.C. 20549

    Attn:
    Mr. Perry Hindin

    Re:
    Direct Digital Holdings, Inc.

    Schedule TO-I/A/Schedule 13E-3

    Filed September 14, 2023

    File No. 005-93602

Ladies and Gentlemen,

On behalf of our client, Direct Digital Holdings, Inc.
(the “Company”), we submit this letter in response to a written comment from the staff (the “Staff”)
of the Securities and Exchange Commission (the “Commission”) contained in its letter dated September 20, 2023,
relating to the above-referenced Schedule TO-I/A/Schedule 13E-3 (the “Schedule TO”). This letter and a publicly filed
Amendment No. 2 to the Schedule TO-I/A/Schedule 13E-3 (the “Amendment”), which includes a Second Amended and
Restated Offer to Purchase as an exhibit to the Amendment, are being filed with the Commission via EDGAR concurrently. In addition to
addressing the comment raised by the Staff in its letter, we have revised the Second Amended and Restated Offer to Purchase to update
other disclosures.

Our response is set forth in ordinary type beneath
the Staff comment, which is set out in bold type. Except for page references appearing in the headings and Staff comments below
(which are references to the Schedule TO filed on September 14, 2023), the page references in our responses are to pages in
the revised Schedule TO and exhibits filed on the date hereof.

Schedule TO-I/A/Schedule 13E-3 filed September 14,
2023

Section 7.
Information Concerning Direct Digital Holdings, Inc., page 21

 1. In
                                            circumstances where the registrant elects to incorporate by reference the information required
                                            by Item 1010(a) and (b) of Regulation M-A, all of the summarized financial information
                                            required by Item 1010(c) must be disclosed in the document furnished to security holders.
                                            See Instruction 1 to Item 13 of Schedule 13E-3. In addition, please refer to telephone interpretation
                                            I.H.7 in the July 2001 supplement to our “Manual of Publicly Available Telephone
                                            Interpretations” that is available on the Commission’s website at http://www.sec.gov
                                            for guidance on complying with a similar instruction in the context of a tender offer. Please
                                            revise the disclosure to include the information required by Item 1010(c)(1), (2) and
                                            (3).

Response:

The Company acknowledges the Staff’s comment
and respectfully advises the Staff that it has revised the Second Amended and Restated Offer to Purchase in the Amendment to include
the information required by Item 1010(c)(1), (2) and (3) in “Section 7. Information Concerning Direct Digital Holdings, Inc.—Historical
Summary Financial Information” beginning on page 22 of the Second Amended and Restated Offer to Purchase.

Securities and Exchange Commission

Division of Corporation Finance

September 21, 2023

Page 2 of 2

Please direct any questions
regarding the Company’s responses or the Schedule TO to me at (212) 548-2122 or solder@mcguirewoods.com.

    Very truly yours,

    MCGUIREWOODS LLP

    /s/ Stephen Older

    Stephen Older

    Partner

    cc:
    Mark Walker, Direct
    Digital Holdings, Inc.

    Keith Smith, Direct Digital
    Holdings, Inc.

    Diana Diaz, Direct Digital Holdings, Inc.

    Andrew Terjesen, McGuireWoods
    LLP

United States securities and exchange commission logo
September 20, 2023
Mark D. Walker
Chairman and Chief Executive Officer
Direct Digital Holdings, Inc.
1177 West Loop South
Suite 1310
Houston, TX 77207
Re:Direct Digital Holdings, Inc.
Schedule TO-I/A/Schedule 13E-3 filed September 14, 2023
File No. 005-93602
Dear Mark D. Walker:
            We have reviewed your September 14, 2023 response to our comment letter and have the
following comments. In some of our comments, we may ask you to provide us with information
so we may better understand your disclosure.
            Please respond to these comments by providing the requested information or advise us as
soon as possible when you will respond. If you do not believe our comments apply to your facts
and circumstances, please tell us why in your response.
            After reviewing your response to these comments, we may have additional comments.
Unless we note otherwise, our references to prior comments are to comments in our September
5, 2023 letter.
Schedule TO-I/A/Schedule 13E-3
Section 7. Information Concerning Direct Digital Holdings, Inc., page 21
1.In circumstances where the registrant elects to incorporate by reference the information
required by Item 1010(a) and (b) of Regulation M-A, all of the summarized financial
information required by Item 1010(c) must be disclosed in the document furnished to
security holders.  See Instruction 1 to Item 13 of Schedule 13E-3.  In addition, please refer
to telephone interpretation I.H.7 in the July 2001 supplement to our “Manual of Publicly
Available Telephone Interpretations” that is available on the Commission’s website at
http://www.sec.gov for guidance on complying with a similar instruction in the context of
a tender offer.  Please revise the disclosure to include the information required by Item
1010(c)(1), (2) and (3).

 FirstName LastNameMark D. Walker
 Comapany NameDirect Digital Holdings, Inc.
 September 20, 2023 Page 2
 FirstName LastName
Mark D. Walker
Direct Digital Holdings, Inc.
September 20, 2023
Page 2
            Please direct any questions to Perry Hindin at 202-551-3444.
Sincerely,
Division of Corporation Finance
Office of Mergers & Acquisitions
cc:       Andrew J. Terjesen

CORRESP
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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.E.

Washington, D.C. 20549

 Re: Direct Digital Holdings, Inc.

Form 10-K for Fiscal Year Ended December 31, 2022

Filed April 17, 2023

File No. 001-41261

Amy Geddes and Lyn Shenk:

We are writing to respond
to the comment provided by the Staff (the “Staff”) of the Division of Corporation Finance of the U.S. Securities and
Exchange Commission in your letter dated August 17, 2023 (the “Comment Letter”), relating to the Direct Digital Holdings,
Inc. (“we”, “Direct Digital”, or the “Company”) Annual Report on Form 10-K for
the fiscal year ended December 31, 2022 (the “Form 10-K”).

For ease of review, we have
set forth below the numbered comment of the Comment Letter in bold type, followed by the Company’s response thereto.

Form 10-K for Fiscal Year Ended December 31,
2022

ITEM 7. Management's Discussion and Analysis
of Financial Condition and Results of Operations

Results of Operations

Comparison of the Fiscal Years Ended December
31, 2022 and 2021, page 52

1. Please quantify each factor, circumstance,
or event leading to each variance cited in comparative analyses. For example, in your discussion of increasing revenue, you cite the increase
in your buy-side advertising revenue due to both expanded spending from your existing customer base as well as new middle market client
spending, and the increase in your sell-side advertising revenue due to a continued increase in impression inventory, as well as increased
publisher engagement across general market and underrepresented publisher communities without quantifying the value of any of these factors.
Refer to the guidance in the introductory paragraph of Item 303(b) of Regulation S-K and (b)(2)(i) therein, and section 501.04 of our
Codification of Financial Reporting Policies.

Response to Comment:

The Company acknowledges the
Staff’s comment and confirms that in future filings, beginning with the Company’s Form 10-Q for the quarter ending September
30, 2023, the Company will include both quantitative and qualitative discussions of each factor, circumstance, or event cited as the cause
or causes of changes in financial statement line items, to the extent such factors are reasonably quantifiable. An illustrative example
of our future enhanced discussion and analysis of revenue, depicted for the fiscal year ended December 31, 2022, is as follows:

Amy Geddes and Lyn Shenk

Securities and Exchange Commission

September 18, 2023

Page 2 of 5

Our revenues increased
from $38.1 million in 2021 to $89.4 million in 2022, an increase of $51.2 million or 134%. Buy-side advertising revenue increased $3.2
million or 12%, while sell-side advertising revenue increased $46.7 million, or 389% over fiscal year 2021. On the buy-side of the business,
we served the needs of approximately 218 small and mid-sized customers during the fiscal year ended December 31, 2022 and saw an increase
of approximately 9% in the average quarterly customer counts in 2022 compared to the prior year. The increase in our buy-side advertising
revenue was due to both expanded spending from our existing customer base as well as new middle market client spending. The increase in
our sell-side advertising revenue was primarily due to a continued increase in impression inventory, as well as increased publisher engagement
across general market and underrepresented publisher communities. The Company sold approximately 1.1 billion average monthly impressions
over the year ended December 31, 2022, an increase of 329% from the prior year. The Company increased its reach across the ecosystem of
buyers from an average of approximately 80,000 advertisers per month in 2021 to approximately 114,000 in 2022, an increase of 43% year
over year. For the year ended December 31, 2022, the Company processed approximately 111 billion average monthly impressions through its
sell-side advertising segment, an increase of 57% from the prior year. We expect continued organic growth in both our buy-side and sell-side
advertising segments over the next twelve months, with our sell-side advertising segment expected to report a higher percentage of our
consolidated revenue.

Notes to Consolidated Financial Statements

Note 2 - Basis of Presentation and Summary
of Significant Accounting Policies

Revenue Recognition, page 73

2. Please provide us with your analysis of
principal versus agent considerations under ASC 606 for buy-side advertising and sell-side advertising separately. Refer to ASC 606-10-25-25
and ASC 606-10-55-36 through 55-40. In your response, please tell us who your customers are and what the specified goods or services are
in each contract with the customer(s).

Response to Comment:

Below is our analysis and conclusions related
to the accounting treatment, under ASC 606, of our role as principal versus agent for buy-side advertising and sell-side advertising.
Based on our prior analysis and conclusions, we believe that our accounting treatment as reflected in our public filings is appropriate
in accordance with GAAP and applicable rules and regulations.

Buy-side advertising:

Background:

We generate revenue from customers that enter
into agreements with us to provide managed advertising campaigns, which include digital marketing and media services to purchase digital
advertising space, data and other add-on features.

Amy Geddes and Lyn Shenk

Securities and Exchange Commission

September 18, 2023

Page 3 of 5

Our customers include advertising space buyers,
including small and mid-sized companies, large advertising holding companies (which may manage several agencies), independent advertising
agencies and mid-market advertising service organizations. We serve a variety of customers across multiple industries including travel/tourism
(including destination marketing organizations (“DMOs”)), energy, consumer packaged goods, healthcare, education, financial
services (including cryptocurrency technologies) and other industries.

Digital media campaigns are initiated upon receipt
of an executed Insertion Order (“IO”). The IO is our contract with the customer that specifies agreed upon marketing tactics,
metric goals and campaign run rates. Consulting services are initiated upon receipt of a master services agreement (“MSA”)
and statement of work (“SOW”). The MSA and SOW specify contractual obligations, service types and timeframes with services
ranging from creative development of ads, management of social media accounts, strategic review of campaigns, employment of campaigns,
website/CRM development and website hosting.

Analysis of principal vs agent considerations:

We offer managed advertising campaigns to our
buy-side advertising customers. Under our customer contracts, we are the primary obligor in the delivery of the managed advertising campaign.
If we do not perform at the level of service required by the IO or MSA/SOW, we will not be paid, but we will still be obligated to pay
for any goods or services we purchase to service a customer’s managed advertising campaign. We are responsible for assisting our
customers with all service requests. Our customers do not interact with any suppliers.

We have evaluated the specified goods or services
and concluded that the managed advertising campaigns are the only specified good or service. Next, we considered whether we control the
managed advertising campaigns before they are provided to the customer. We concluded that we control the managed advertising campaigns
because we are the primary obligor. As part of this assessment, we also considered the three indicators of control in the standard and
made the following determinations that support our overall control evaluation:

 - We are responsible for fulfilling the promise to the customer,
and we take responsibility for the acceptability of the managed advertising campaigns.

 - We bear the financial risk of all costs incurred for the managed advertising
campaign regardless of whether the campaign achieves the campaign goal and results in revenue for us.

 - Pricing is set in the IO or MSA/SOW.

Based upon this analysis, we concluded that we
are a principal for the managed advertising campaigns sold through our buy-side subsidiaries, Huddled Masses, LLC and Orange142, LLC,
because we are the primary obligor in the agreement with the customer.

Sell-side advertising:

Background:

We generate revenue by selling advertising inventory
(digital ad units) that we purchase from publishers to advertisers through a process of monetizing ad impressions on our proprietary sell-side
programmatic platform operating under the trademarked banner of Colossus SSP.

Amy Geddes and Lyn Shenk

Securities and Exchange Commission

September 18, 2023

Page 4 of 5

Our customers include demand side platforms (“DSPs”),
agencies and individual advertisers. We generally enter into Supply Path Optimization agreements directly with customers which addresses
acceptable advertisements and data usage. As part of these agreements, we provide advertisers and agencies with benefits ranging from
custom data and workflow integrations, product features, volume-based business terms, and visibility into campaign performance data and
methodology. As a result of these direct relationships, our existing advertisers and agencies are incentivized to allocate an increasing
percentage of their advertising budgets to our platform.

We strive to retain existing publishers and add
new publishers. Establishing multiple header bidding integrations by leveraging our technology capabilities allows us to maximize our
access to publishers’ ad formats, devices and various properties that a publisher may own. We may also up-sell additional products
to publisher customers including our header bidding management, identity, and audience solutions. We enter into master service agreements
with our publishers which, among other terms, set a fixed rate for content to be sold on Colossus SSP.

Our success is based on:

 - Curating advertisers and increasing access to publishers with valuable ad impressions. We monetize digital
impressions by coordinating daily real-time auctions and bids. We continuously review our available inventory from existing publishers
across every format (mobile, desktop, digital video, OTT, CTV, and rich media). The factors we consider when determining which impressions
we process include transparency, viewability, and whether or not the impression is human sourced. By consistently applying these criteria,
we believe the ad impressions we process will be valuable and marketable to advertisers.

 - Enhancing ad inventory quality. In the advertising industry, inventory quality is assessed in terms of
invalid traffic (“IVT”) which can be impacted by fraud such as “fake eyeballs” generated by automated technologies
set up to artificially inflate impression counts. Through our platform design and proactive IVT mitigation efforts, we address and minimize
IVT on a number of fronts, including sophisticated technology, which detects and avoids IVT on the front end; direct publisher and inventory
relationships, for supply path optimization; and ongoing campaign and inventory performance review, to ensure inventory quality and brand
protection controls are in place.

Analysis of principal vs agent considerations:

Our Colossus SSP technology platform provides
a marketplace for customers to purchase digital advertising inventory (digital ad units). We have entered into contracts with suppliers
that provide us with the right to sell the digital ad units during a noncancellable period of time in exchange for a fixed rate for digital
ad units sold. We can set the minimum price for the digital ad units to be sold to customers on Colossus SSP, but the final price is determined
by buyers participating in the marketplace. We are contractually required to pay the publisher (supplier) a fixed rate for any digital
ad units we sell to our advertisers (customers), and that rate is unaffected by the price paid by the advertisers (customers). We are
responsible for assisting our advertisers (customers) with all service requests including issues with purchasing the advertising units
or properly displaying their ads with the publisher (supplier). Our customers do not interact with the publishers (suppliers).

We have evaluated the specified goods or services
and concluded that the digital ad units are the only specified good or service. Next, we considered whether we control the digital ad
units before they are transferred to the customer. We concluded that we control the digital ad units before they are transferred because
we have entered into noncancellable distribution agreements with our publishers (suppliers) that permit us to sell the digital ad units
to our advertisers (customers). As part of this assessment, we also considered the three indicators of control in the standard and made
the following determinations that support our overall control evaluation:

Amy Geddes and Lyn Shenk

Securities and Exchange Commission

September 18, 2023

Page 5  of 5

 - We are responsible for fulfilling the promise to the customer,
and we take responsibility for the acceptability of the digital ad units.

 - There is no inventory risk associated with the digital ad units, however
the other factors establish control and support the principal conclusion

 - We have discretion to establish minimum prices

Based upon this analysis, we concluded that we
are a principal for the digital ad units sold through our sell-side platform Colossus SSP because we control the digital ad units before
they are transferred to the customer.

⁕⁕⁕

Should any member of the Staff have questions
regarding our responses to the comments set forth above or need additional information, please do not hesitate to call me at 832-402-1054.
Thank you for your assistance in this matter.

    Very truly yours,

    /s/ Diana P. Diaz

    Diana P. Diaz

    Interim Chief Financial Officer

cc(electronic): Mark Walker, Chairman & CEO

Rakesh Gopalan, McGuireWoods LLP

CORRESP
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    McGuireWoods LLP

    1251 Avenue of the Americas

    20th Floor

    New York, NY 10020

VIA EDGAR AND EMAIL

September 14, 2023

U.S. Securities and Exchange Commission

Division of Corporation Finance

Office of Mergers & Acquisitions

100 F Street, N.E.

Washington, D.C. 20549

Attn: Mr. Perry Hindin

    Re:

    Direct Digital Holdings, Inc.

    Schedule TO-I

    Filed August 29, 2023

    CIK No. 0001880613

On behalf of our client, Direct Digital
Holdings, Inc. (the “Company”), we submit this letter in response to written comments from the staff (the
 “Staff”) of the Securities and Exchange Commission (the “Commission”) contained in its letter
dated September 5, 2023, relating to the above-referenced Schedule TO-I (File No. 005-93602) (the “Schedule TO”).
This letter and a publicly filed Amendment No. 1 to the Schedule TO-I (the “Amendment”), which includes an
Amended and Restated Offer to Purchase as an exhibit to the Amendment, are being filed with the Commission via EDGAR concurrently.
In addition to addressing the comments raised by the Staff in its letter, we have revised the Amended and Restated Offer to Purchase
to update other disclosures.

Each of our responses is set forth in ordinary
type beneath the corresponding Staff comment, which is set out in bold type. Except for page references appearing in the headings and
Staff comments below (which are references to the Schedule TO filed on August 29, 2023), the page references in our responses are to pages
in the revised Schedule TO and exhibits filed on the date hereof.

Schedule TO submitted filed August 29, 2023

Minimum Tender Condition, page 6

 1. Disclosure in this section indicates that “[b]ased on the 3,217,800
Warrants outstanding as of August 28, 2023, 1,609,222 Warrants would need to be tendered in order to satisfy the Minimum Tender Condition
[the tender of more than 50% of the outstanding Warrants].” It would appear that only 1,608,901 Warrants need be tendered to satisfy
this condition. Please advise or revise.

Response:

The Company acknowledges the Staff’s comment
and respectfully advises the Staff that the Amended and Restated Offer to Purchase filed with the Amendment has been revised to clarify
that the Minimum Tender Condition for the tender offer is 50.1% or more of the outstanding Warrants. The Minimum Tender Condition is intended
to track the number of Warrants that are required to consent to effect an amendment to the Warrant Agent Agreement.

Securities and Exchange Commission

Division of Corporation Finance

September 14, 2023

Page 2 of 2

Based on the 3,217,800 publicly traded Warrants
outstanding as of September 14, 2023, the number of Warrants needed to be tendered in order to satisfy the Minimum Tender Condition is
1,612,118 Warrants. The 1,609,222 number in the Schedule TO filed on August 29, 2023 was the result of a mathematical error as it represents
50.01% of the outstanding Warrants, not 50.1%. The Amended and Restated Offer to Purchase has been revised on page 15 to reflect that
1,612,118 is the number of Warrants that will need to be tendered in order to satisfy the Minimum Tender Condition.

Forward-Looking Statements; Risk
Factors, page 20

 2. We note your reference to Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934. Note
that the safe harbor protections for forward-looking statements contained in those federal securities laws do not apply to statements
made in connection with a tender offer. See Section 21E(b)(2)(C) of the Securities Exchange Act of 1934. Please delete the reference or
clarify that it is not applicable to the tender offer.

Response:

The Company acknowledges the Staff’s comment
and respectfully advises the Staff that it has revised the Amended and Restated Offer to Purchase in the Amendment to delete the reference
to the Private Securities Litigation and Reform Act of 1995.

General

 3. In your response letter, please explain why this issuer tender offer is not subject to Exchange Act Rule 13e-3. We note that it
is an offer for all outstanding Warrants which are currently listed on the Nasdaq. To the extent that Warrants are not tendered but the
offer is consummated, the remaining Warrants will be subject to redemption at a reduced price as compared to the offer price. In the alternative,
please file and disseminate a Schedule 13E-3.

The Company acknowledges the
Staff’s comment and respectfully advises the Staff that it has filed the Amendment as a combined Schedule TO-I/13E-3 in response
to Comment 3.

Please direct any questions
regarding the Company’s responses or the Schedule TO to me at (212) 548-2122 or solder@mcguirewoods.com.

    Very truly yours,

    MCGUIREWOODS LLP

    /s/ Stephen Older

    Stephen Older

    Partner

    cc:
    Mark Walker, Direct Digital Holdings, Inc.

    Keith Smith, Direct Digital Holdings, Inc.

    Diana Diaz, Direct Digital Holdings, Inc.

    Andrew Terjesen, McGuireWoods LLP

CORRESP
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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.E.

Washington, D.C. 20549

 Re: Direct Digital Holdings, Inc.

Form 10-K for Fiscal Year Ended December
31, 2022

Filed April 17, 2023

File No. 001-41261

Amy Geddes and Lyn Shenk:

Direct Digital Holdings, Inc.
(the “Company”) is sending this letter to confirm the extension of time to respond to the comment letter dated August
17, 2023 from the staff (the “Staff”) of the Securities and Exchange Commission’s Division of Corporation Finance
relating to the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2022. As per our counsel’s discussion
with Ms. Geddes on September 11, 2023, this letter confirms that the agreed deadline for the Company to file its written response to the
Staff’s comment letter is September 18, 2023. Please contact me at 832-402-1054 should you have any questions or concerns.

    Very truly yours,

    /s/ Diana P. Diaz

    Diana P. Diaz

    Interim Chief Financial Officer

    cc (electronic):
    Mark Walker, Chairman & CEO

    Rakesh Gopalan, McGuireWoods LLP

United States securities and exchange commission logo
September 5, 2023
Mark D. Walker
Chairman and Chief Executive Officer
Direct Digital Holdings, Inc.
1177 West Loop South
Suite 1310
Houston, TX 77207
Re:Direct Digital Holdings, Inc.
Schedule TO-I filed August 29, 2023
File No. 005-93602
Dear Mark D. Walker:
            We have reviewed your filing and have the following comments. In some of our
comments, we may ask you to provide us with information so we may better understand your
disclosure.
            Please respond to these comments by providing the requested information or advise us as
soon as possible when you will respond. If you do not believe our comments apply to your facts
and circumstances, please tell us why in your response.
            After reviewing your response to these comments, we may have additional comments.
Schedule TO-I filed August 29, 2023
Minimum Tender Condition, page 6
1.Disclosure in this section indicates that “[b]ased on the 3,217,800 Warrants outstanding as
of August 28, 2023, 1,609,222 Warrants would need to be tendered in order to satisfy the
Minimum Tender Condition [the tender of more than 50% of the outstanding Warrants].”
It would appear that only 1,608,901 Warrants need be tendered to satisfy this condition.
Please advise or revise.
Forward-Looking Statements; Risk Factors, page 20
2.We note your reference to Section 27A of the Securities Act of 1933 and Section 21E of
the Securities Exchange Act of 1934.  Note that the safe harbor protections for forward-
looking statements contained in those federal securities laws do not apply to statements
made in connection with a tender offer.  See Section 21E(b)(2)(C) of the Securities
Exchange Act of 1934.  Please delete the reference or clarify that it is not applicable to the

 FirstName LastNameMark D. Walker
 Comapany NameDirect Digital Holdings, Inc.
 September 5, 2023 Page 2
 FirstName LastName
Mark D. Walker
Direct Digital Holdings, Inc.
September 5, 2023
Page 2
tender offer.
General
3.In your response letter, please explain why this issuer tender offer is not subject to
Exchange Act Rule 13e-3. We note that it is an offer for all outstanding Warrants which
are currently listed on the Nasdaq.  To the extent that Warrants are not tendered but the
offer is consummated, the remaining Warrants will be subject to redemption at a reduced
price as compared to the offer price.  In the alternative, please file and disseminate a
Schedule 13E-3.
            We remind you that the filing persons are responsible for the accuracy and adequacy of
their disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please direct any questions to Perry Hindin at 202-551-3444.
Sincerely,
Division of Corporation Finance
Office of Mergers & Acquisitions
cc:       Andrew J. Terjesen

CORRESP
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filename1.htm

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.E.

Washington, D.C. 20549

 Re: Direct Digital Holdings, Inc.

Form 10-K for Fiscal Year Ended December 31, 2022

Filed April 17, 2023

File No. 001-41261

Amy Geddes and Lyn Shenk:

Direct Digital Holdings, Inc.
(the “Company”) is sending this letter to confirm the extension of time to respond to the comment letter dated August
17, 2023 from the staff (the “Staff”) of the Securities and Exchange Commission’s Division of Corporation Finance
relating to the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2022. As per our counsel’s discussion
with Ms. Geddes on August 29, 2023, this letter confirms that the agreed deadline for the Company to file its written response to the
Staff’s comment letter is September 11, 2023. Please contact me at 832-402-1054 should you have any questions or concerns.

    Very truly yours,

    /s/ Diana P. Diaz

    Diana P. Diaz

    Interim Chief Financial Officer

cc (electronic): Mark Walker, Chairman & CEO

Rakesh Gopalan, McGuireWoods LLP

United States securities and exchange commission logo
August 17, 2023
Mark Walker
Chief Executive Officer
Direct Digital Holdings, Inc.
1177 West Loop South ,Suite 1310
Houston, Texas 77027
Re:Direct Digital Holdings, Inc.
Form 10-K for Fiscal Year Ended December 31, 2022
Filed April 17, 2023
File No. 001-41261
Dear Mark Walker:
            We have limited our review of your filing to the financial statements and related
disclosures and have the following comments.  In some of our comments, we may ask you to
provide us with information so we may better understand your disclosure.
            Please respond to these comments within ten business days by providing the requested
information or advise us as soon as possible when you will respond.  If you do not believe our
comments apply to your facts and circumstances, please tell us why in your response.
            After reviewing your response to these comments, we may have additional comments.
Form 10-K for Fiscal Year Ended December 31, 2022
ITEM 7. Management's Discussion and Analysis of Financial Condition and Results of
Operations
Results of Operations
Comparison of the Fiscal Years Ended December 31, 2022 and 2021, page 52
1.Please quantify each factor, circumstance, or event leading to each variance cited in
comparative analyses.  For example, in your discussion of increasing revenue, you cite the
increase in your buy-side advertising revenue due to both expanded spending from your
existing customer base as well as new middle market client spending, and the increase in
your sell-side advertising revenue due to a continued increase in impression inventory, as
well as increased publisher engagement across general market and underrepresented
publisher communities without quantifying the value of any of these factors.  Refer to the
guidance in the introductory paragraph of Item 303(b) of Regulation S-K and (b)(2)(i)
therein, and section 501.04 of our Codification of Financial Reporting Policies.

 FirstName LastNameMark Walker
 Comapany NameDirect Digital Holdings, Inc.
 August 17, 2023 Page 2
 FirstName LastName
Mark Walker
Direct Digital Holdings, Inc.
August 17, 2023
Page 2
Notes to Consolidated Financial Statements
Note 2 - Basis of Presentation and Summary of Significant Accounting Policies
Revenue Recognition, page 73
2.Please provide us with your analysis of principal versus agent considerations under ASC
606 for buy-side advertising and sell-side advertising separately.  Refer to ASC 606-10-
25-25 and ASC 606-10-55-36 through 55-40.  In your response, please tell us who your
customers are and what the specified goods or services are in each contract with the
customer(s).
            In closing, we remind you that the company and its management are responsible for the
accuracy and adequacy of their disclosures, notwithstanding any review, comments, action or
absence of action by the staff.
            You may contact Amy Geddes at 202-551-3304 or Lyn Shenk at 202-551-3380 with any
questions.
Sincerely,
Division of Corporation Finance
Office of Trade & Services

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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

Ladies and Gentlemen:

Pursuant to Rule 461 under
the Securities Act of 1933, as amended, Direct Digital Holdings, Inc. (the “Company”) hereby requests that the Securities
and Exchange Commission (the “Commission”) accelerate the effective date of the above-referenced Registration Statement
on Form S-3 (as amended, the “Registration Statement”) so that the Registration Statement will be declared effective
as of 4:01 p.m. Eastern Time, on May 4, 2023, or at such other time as the Company or its outside counsel, McGuireWoods LLP, may request
via a telephone call to the staff of the Commission.

Once the Registration Statement
has been declared effective, please orally confirm that event with Rakesh Gopalan of McGuireWoods LLP at (704) 343-2275, or in his absence,
David Wolpa of McGuireWoods at (704) 343-2185.

Thank you for your assistance
in this matter.

    Sincerely,

    Direct Digital Holdings, Inc.

    /s/ Susan Echard

    Susan Echard, Chief Financial Officer

United States securities and exchange commission logo
May 1, 2023
Mark Walker
Chairman and Chief Executive Officer
Direct Digital Holdings, Inc.
1177 West Loop South, Suite 1310
Houston, TX 77207
Re:Direct Digital Holdings, Inc.
Registration Statement on Form S-3
Filed April 21, 2023
File No. 333-271382
Dear Mark Walker:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration.  We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Taylor Beech at 202-551-4515 with any questions.
Sincerely,
Division of Corporation Finance
Office of Trade & Services
cc:       Rakesh Gopalan, Esq.

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February 8, 2022

VIA EDGAR TRANSMISSION

Division of Corporation Finance

United States Securities and Exchange Commission

100 F Street, N.E.

Washington, D.C. 20549-6010

    Attn:

    Ms. Claire DeLabar

    Mr. Robert Littlepage

    Mr. Austin Pattan

    Ms. Kathleen Krebs

    Re:
    Direct Digital Holdings, Inc.

    Registration Statement on Form S-1 (Registration No. 333-261059)

    Request for Acceleration of Effective Date

Ladies and gentlemen:

In accordance with Rule 461
under the Securities Act of 1933, as amended (the “Act”), The Benchmark Company, LLC and Roth Capital Partners, LLC, as representatives
of the several underwriters, hereby join Direct Digital Holdings, Inc. (the “Company”) in requesting that the Securities
and Exchange Commission (the “Commission”) take appropriate action to cause the Registration Statement on Form S-1 (File
No. 333-261059) (the “Registration Statement”) to become effective on February 10, 2022, at 4:30 p.m., Eastern Time,
or at such other time as the Company or its outside counsel, McGuireWoods LLP, may request via a telephone call to the staff of the Commission.

Pursuant to Rule 460
under the Act, please be advised that we will take reasonable steps to secure adequate distribution of the preliminary prospectus to underwriters,
dealers, institutions and others prior to the requested effective time of the Registration Statement.

The undersigned, as representatives
of the several underwriters, have complied and will comply, and we have been informed by the participating underwriters and dealers that
they have complied with and will continue to comply with the requirements of Rule 15c2-8 under the Securities Exchange Act of 1934,
as amended.

[Signature Page Follows]

    Very truly yours,

    THE BENCHMARK COMPANY, LLC

    By:
    /s/ Michael Jacobs

    Name:
    Michael Jacobs

    Title:
    MD/Head of ECM

    ROTH CAPITAL PARTNERS, LLC

    By:
    /s/ Aaron M. Gurewitz

    Name:
    Aaron M. Gurewitz

    Title:
    Head of Equity Capital Markets

    cc:
    Mark D. Walker, Chief Executive Officer, Direct Digital Holdings, Inc.

    Susan Echard, Chief Financial Officer, Direct Digital Holdings, Inc.

    Phyllis Young, Esq., McGuireWoods LLP

    Stephen E. Older, Esq., McGuireWoods LLP

    Rakesh Gopalan, Esq., McGuireWoods LLP

    Ben A. Stacke, Esq., Faegre Drinker Biddle & Reath LLP

CORRESP
1
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February 8, 2022

VIA EDGAR TRANSMISSION

United States Securities and Exchange Commission

Division of Corporation Finance

Office of Technology

100 F Street, N.E.

Washington, D.C. 20549

    Attn:
    Claire DeLabar

    Robert Littlepage

    Austin Pattan

    Kathleen Krebs

    Re:

    Direct Digital Holdings, Inc.

    Registration Statement on Form S-1, as amended
    (File No. 333-261059)

    Request for Acceleration of Effective Date

Ladies and Gentlemen:

Pursuant to Rule 461 under
the Securities Act of 1933, as amended, Direct Digital Holdings, Inc. (the “Company”) hereby requests that the Securities
and Exchange Commission (the “Commission”) accelerate the effective date of the above-referenced Registration Statement
on Form S-1 (as amended, the “Registration Statement”) so that the Registration Statement will be declared effective
as of 4:30 p.m. Eastern time, on February 10, 2022, or as soon thereafter as practicable. Once the Registration Statement has been declared
effective, please orally confirm that event with our counsel, McGuireWoods LLP, by calling Rakesh Gopalan at (704) 343-2275 or David Wolpa
at (704) 343-2185.

Thank you for your assistance
in this matter.

    Very truly yours,

    Direct Digital Holdings, Inc.

    /s/ Mark Walker

    Name:
    Mark Walker

    Title:
    Chairman and Chief Executive Officer

    cc:

    (via email)

    Keith Smith, President, Direct Digital Holdings, Inc.

    Susan Echard, Chief Financial Officer, Direct Digital Holdings, Inc.

    Phyllis Young, McGuireWoods LLP

    Stephen Older, McGuireWoods LLP

    Rakesh Gopalan, McGuireWoods LLP

    Ben Stacke, Faegre Drinker Biddle & Reath LLP

CORRESP
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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 client,
Direct Digital Holdings, Inc. (the “Company”), we submit this letter in response to comments from the staff of the
Division of Corporation Finance (the “Staff”) of the Securities and Exchange Commission (the “Commission”)
contained in its letter dated February 3, 2022, relating to the above referenced Amendment No. 3 to the Registration Statement on Form
S-1 (the “Amendment No. 3”). This letter and our Amendment No. 5 to the Registration Statement on Form S-1 (the “Amendment
No. 5”) are being filed with the Commission via EDGAR electronically today. In addition to the electronic filing, we are delivering
via email a copy of this letter, along with a courtesy copy of the Amendment No. 5 marked to indicate changes from the Amendment No.
3 filed on January 31, 2022.

Each of our responses is set
forth in ordinary type beneath the corresponding Staff comment, which is set out in bold type. Except for page references appearing in
the headings and Staff comments below (which are references to the Amendment No. 3), the page references in our responses are to pages
in the Amendment No. 5.

Amendment No. 3 to the Registration Statement
on Form S-1 filed January 31, 2022 Capitalization, page 63

 1. Disclose in a separate column after the actual information, the capitalization
                                            of Direct Digital Holdings on a pro forma basis to give effect to the Organizational Transactions,
                                            excluding the effects of this offering.

Response:

The Company advises the Staff that the Company
has revised the disclosure on page 63 of Amendment No. 5 to add a column disclosing the capitalization of the Company on a pro forma basis
to give effect to the Organizational Transactions (as defined in Amendment No. 5), excluding the effects of the offering.

Securities and Exchange Commission

Division of Corporation Finance

February 7, 2022

Page 2 of 3

Unaudited Pro Forma Consolidated
Financial Information, page 68

 2. Disclose why you are presenting a pro forma consolidated statement of
                                            operations for the nine months ended September 30, 2020. Also, revise your introductory disclosures
                                            to indicate that you are giving effect to the acquisition of Orange142 as if such transaction
                                            had occurred on January 1, 2020, not 2021, in the unaudited pro forma consolidated statement
                                            of operations for the nine months ended September 30, 2020.

Response:

The Company advises the Staff that the Company
has revised Amendment No. 5 to remove the pro forma consolidated statement of operations for the nine months ended September 30, 2020.
In its place, the Company is including (i) an actual consolidated statement of operations for the nine months ended September 30, 2021,
(ii) a consolidated statement of operations for the nine months ended September 30, 2021 giving pro forma effect to the Organizational
Transactions, excluding the offering, and (iii) a consolidated statement of operations for the nine months ended September 30, 2021 giving
pro forma effect to the Organizational Transactions, including the offering. Because the acquisition of Orange142, LLC (“Orange142”)
was completed during the fiscal year ended December 31, 2020, Orange142’s financial results of operations were included in the Company’s
consolidated results for the entirety of the nine-month period ended September 30, 2021, and accordingly, any additional pro forma effect
of the acquisition of Orange142 for such nine-month period is unnecessary.

Pro Forma Consolidated Statements
of Operations, page 71

 3. Disclose pro forma earnings per share data for all periods. This information
                                            should be referenced to a sufficiently detailed footnote explaining the calculations.

Response:

The Company advises the Staff that the Company
has revised Amendment No. 5 to add pro forma earnings per share data for all periods presented.

 4. Provide a pro forma income statement for the nine months ended September
                                            30, 2021 to give effect to the Organizational Transactions as if such transactions occurred
                                            on January 1, 2020.

Response:

As noted above in our response to comment number
2, the Company advises the Staff that the Company has revised Amendment No. 5 to remove the pro forma consolidated statement of operations
for the nine months ended September 30, 2020. In its place, the Company is including (i) an actual consolidated statement of operations
for the nine months ended September 30, 2021, (ii) a consolidated statement of operations for the nine months ended September 30, 2021
giving pro forma effect to the Organizational Transactions, excluding the offering, and (iii) a consolidated statement of operations for
the nine months ended September 30, 2021 giving pro forma effect to the Organizational Transactions, including the offering. No additional
adjustments to such nine-month period are necessary due to the reasons set forth in our response to comment number 2.

Securities and Exchange Commission

Division of Corporation Finance

February 7, 2022

Page 3  of 3

Pro Forma Balance Sheet, page 73

 5. Limit your presentation of the pro forma balance sheet to the most recent
                                            historic balance sheet date.

Response:

The Company advises the Staff that the Company
has revised Amendment No. 5 to remove the historic balance sheet information, actual and pro forma, as of December 31, 2020.

 6. In a separate pro forma adjustment column, quantify each pro forma balance
                                            sheet adjustment giving effect to the Organizational Transactions and reference each to a
                                            sufficiently detailed footnote.

Response:

The Company advises the Staff that the Company
has revised Amendment No. 5 to quantify each pro forma balance sheet adjustment giving effect to the Organizational Transactions, including
a reference to sufficiently detailed footnotes thereto.

***

Please direct any questions
regarding the Company’s responses or the Amendment No. 5 to me at (704) 343-2275 or rgopalan@mcguirewoods.com.

    Very truly yours,

    /s/ Rakesh Gopalan

    Rakesh Gopalan

    Partner

cc (via email):

Mark Walker, Direct Digital
Holdings, Inc.

Keith Smith, Direct Digital
Holdings, Inc.

Susan Echard, Direct Digital
Holdings, Inc.

Phyllis Young, McGuireWoods
LLP

Stephen Older, McGuireWoods
LLP

Ben Stacke, Faegre Drinker
Biddle & Reath LLP

CORRESP
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February 3, 2022

VIA EDGAR TRANSMISSION

Division of Corporation Finance

United States Securities and Exchange Commission

100 F Street, N.E.

Washington, D.C. 20549-6010

    Attn:

    Ms. Claire DeLabar

    Mr. Robert Littlepage

    Mr. Austin Pattan

    Ms. Kathleen Krebs

    Re:
    Direct Digital Holdings, Inc.

    Registration Statement on Form S-1 (Registration No. 333-261059)

    Withdrawal of Prior Acceleration Request

Ladies and gentlemen:

Reference is made to our
letter, filed as correspondence with the U.S. Securities and Exchange Commission via EDGAR on February 2, 2022, in which we requested
the acceleration of the effective date of the above-captioned Registration Statement, as amended, to 4:30 p.m., Eastern Time, on February 3,
2022. We are no longer requesting that the Registration Statement be declared effective at that date and time, and we hereby formally
withdraw our prior request for acceleration of the effective date of the above-captioned Registration Statement, as amended.

[Signature Page Follows]

    Very truly yours,

    THE BENCHMARK COMPANY, LLC

    By:
    /s/ Michael Jacobs

    Name:
    Michael Jacobs

    Title:
    MD/Head of ECM

    ROTH CAPITAL PARTNERS, LLC

    By:
    /s/ Aaron M. Gurewitz

    Name:
    Aaron M. Gurewitz

    Title:
    Head of Equity Capital Markets

    cc:
    Mark D. Walker, Chief Executive Officer, Direct Digital Holdings, Inc.

    Susan Echard, Chief Financial Officer, Direct Digital Holdings, Inc.

    Phyllis Young, Esq., McGuireWoods LLP

    Stephen E. Older, Esq., McGuireWoods LLP

    Rakesh Gopalan, Esq., McGuireWoods LLP

    Ben A. Stacke, Esq., Faegre Drinker Biddle & Reath LLP

United States securities and exchange commission logo
February 3, 2022
Mark Walker
Chief Executive Officer
Direct Digital Holdings, Inc.
1233 West Loop South, Suite 1170
Houston, TX 77027
Re:Direct Digital Holdings, Inc.
Amendment No. 3 to Registration Statement on Form S-1
Filed January 31, 2021
File No. 333-261059
Dear Mr. Walker:
            We have reviewed your amended registration statement and have the following
comments.  In some of our comments, we may ask you to provide us with information so we
may better understand your disclosure.
            Please respond to this letter by amending your registration statement and providing the
requested information.  If you do not believe our comments apply to your facts and
circumstances or do not believe an amendment is appropriate, please tell us why in your
response.
            After reviewing any amendment to your registration statement and the information you
provide in response to these comments, we may have additional comments.
Amendment No. 3 to Form S-1
Capitalization, page 63
1.Disclose in a separate column after the actual information, the capitalization of Direct
Digital Holdings on a pro forma basis to give effect to the Organizational Transactions,
excluding the effects of this offering.
Unaudited Pro Forma Consolidated Financial Information, page 68
2.Disclose why you are presenting a pro forma consolidated statement of operations for the
nine months ended September 30, 2020.  Also, revise your introductory disclosures to
indicate that you are giving effect to the acquisition of Orange142 as if such transaction
had occurred on January 1, 2020, not 2021, in the unaudited pro forma consolidated
statement of operations for the nine months ended September 30, 2020.

 FirstName LastNameMark Walker
 Comapany NameDirect Digital Holdings, Inc.
 February 3, 2022 Page 2
 FirstName LastName
Mark Walker
Direct Digital Holdings, Inc.
February 3, 2022
Page 2
Pro Forma Consolidated Statements of Operations, page 71
3.Disclose pro forma earnings per share data for all periods.  This information should be
referenced to a sufficiently detailed footnote explaining the calculations.
4.Provide a pro forma income statement for the nine months ended September 30, 2021 to
give effect to the Organizational Transactions as if such transactions occurred on January
1, 2020.
Pro Forma Balance Sheet, page 73
5.Limit your presentation of the pro forma balance sheet to the most recent historic balance
sheet date.
6.In a separate pro forma adjustment column, quantify each pro forma balance sheet
adjustment giving effect to the Organizational Transactions and reference each to a
sufficiently detailed footnote.
            You may contact Claire DeLabar, Senior Staff Accountant, at (202) 551-3349 or Robert
Littlepage, Accounting Branch Chief, at (202) 551-3361 if you have questions regarding
comments on the financial statements and related matters.  Please contact Austin Pattan, Staff
Attorney, a (202) 551-6756 or Kathleen Krebs, Special Counsel, at (202) 551-3350 with any
other questions.
Sincerely,
Division of Corporation Finance
Office of Technology
cc:       Rakesh Gopalan

CORRESP
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February 3, 2022

VIA EDGAR TRANSMISSION

United States Securities and Exchange Commission

Division of Corporation Finance

Office of Technology

100 F Street, N.E.

Washington, D.C. 20549

    Attn:
    Claire DeLabar

    Robert Littlepage

    Austin Pattan

    Kathleen Krebs

    Re:

    Direct Digital Holdings, Inc.

    Registration Statement on Form S-1, as
    amended (File No. 333-261059)

    Withdrawal of Prior Acceleration Request

Ladies and Gentlemen:

Reference is made to our letter,
filed as correspondence, with the U.S. Securities and Exchange Commission via EDGAR on February 2, 2022, in which we requested the
acceleration of the effective date of the above-captioned Registration Statement, as amended, to 4:30 p.m., Eastern time, on February 3,
2022. We are no longer requesting that the Registration Statement be declared effective at that date and time, and we hereby formally
withdraw our prior request for acceleration of the effective date of the above-captioned Registration Statement, as amended.

    Very truly yours,

    Direct Digital Holdings, Inc.

    /s/ Mark Walker

    Name:
    Mark Walker

    Title:
    Chairman and Chief Executive Officer

    cc:

    (via email)

    Keith Smith, President, Direct Digital Holdings, Inc.

    Susan Echard, Chief Financial Officer, Direct Digital Holdings, Inc.

    Phyllis Young, McGuireWoods LLP

    Stephen Older, McGuireWoods LLP

    Rakesh Gopalan, McGuireWoods LLP

    Ben Stacke, Faegre Drinker Biddle & Reath LLP

CORRESP
1
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February 2, 2022

VIA EDGAR TRANSMISSION

Division of Corporation Finance

United States Securities and Exchange Commission

100 F Street, N.E.

Washington, D.C. 20549-6010

    Attn:

    Ms. Claire DeLabar

    Mr. Robert Littlepage

    Mr. Austin Pattan

    Ms. Kathleen Krebs

    Re:
    Direct Digital Holdings, Inc.

    Registration Statement on Form S-1 (Registration No. 333-261059)

    Request for Acceleration of Effective Date

Ladies and gentlemen:

In accordance with Rule 461
under the Securities Act of 1933, as amended (the “Act”), The Benchmark Company, LLC and Roth Capital Partners, LLC, as representatives
of the several underwriters, hereby join Direct Digital Holdings, Inc. (the “Company”) in requesting that the Securities
and Exchange Commission (the “Commission”) take appropriate action to cause the Registration Statement on Form S-1 (File
No. 333-261059) (the “Registration Statement”) to become effective on February 3, 2022, at 4:30 p.m., Eastern Time,
or at such other time as the Company or its outside counsel, McGuireWoods LLP, may request via a telephone call to the staff of the Commission.

Pursuant to Rule 460
under the Act, please be advised that we will take reasonable steps to secure adequate distribution of the preliminary prospectus to underwriters,
dealers, institutions and others prior to the requested effective time of the Registration Statement.

The undersigned, as representatives
of the several underwriters, have complied and will comply, and we have been informed by the participating underwriters and dealers that
they have complied with and will continue to comply with the requirements of Rule 15c2-8 under the Securities Exchange Act of 1934,
as amended.

[Signature Page Follows]

    Very truly yours,

    THE BENCHMARK COMPANY, LLC

    By:
    /s/ Michael Jacobs

    Name:
    Michael Jacobs

    Title:
    MD/Head of ECM

    ROTH CAPITAL PARTNERS, LLC

    By:
    /s/ Aaron M. Gurewitz

    Name:
    Aaron M. Gurewitz

    Title:
    Head of Equity Capital Markets

    cc:
    Mark D. Walker, Chief Executive Officer, Direct Digital Holdings, Inc.

    Susan Echard, Chief Financial Officer, Direct Digital Holdings, Inc.

    Phyllis Young, Esq., McGuireWoods LLP

    Stephen E. Older, Esq., McGuireWoods LLP

    Rakesh Gopalan, Esq., McGuireWoods LLP

    Ben A. Stacke, Esq., Faegre Drinker Biddle & Reath LLP

CORRESP
1
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February 2, 2022

VIA EDGAR TRANSMISSION

United States Securities and Exchange Commission

Division of Corporation Finance

Office of Technology

100 F Street, N.E.

Washington, D.C. 20549

    Attn:
    Claire DeLabar

    Robert Littlepage

    Austin Pattan

    Kathleen Krebs

    Re:

    Direct Digital Holdings, Inc.

    Registration Statement on Form S-1, as
    amended (File No. 333-261059)

    Request for Acceleration of Effective Date

Ladies and Gentlemen:

Pursuant to Rule 461
under the Securities Act of 1933, as amended, Direct Digital Holdings, Inc. (the “Company”) hereby requests that
the Securities and Exchange Commission (the “Commission”) accelerate the effective date of the above-referenced Registration
Statement on Form S-1 (as amended, the “Registration Statement”) so that the Registration Statement will be declared
effective as of 4:30 p.m. Eastern time, on February 3, 2022, or as soon thereafter as practicable. Once the Registration Statement
has been declared effective, please orally confirm that event with our counsel, McGuireWoods LLP, by calling Rakesh Gopalan at (704) 343-2275
or David Wolpa at (704) 343-2185.

Thank you for your assistance
in this matter.

    Very truly yours,

    Direct Digital Holdings, Inc.

    /s/ Mark Walker

    Name:
    Mark Walker

    Title:
    Chairman and Chief Executive Officer

    cc:

    (via email)

    Keith Smith, President, Direct Digital Holdings, Inc.

    Susan Echard, Chief Financial Officer, Direct Digital Holdings, Inc.

    Phyllis Young, McGuireWoods LLP

    Stephen Older, McGuireWoods LLP

    Rakesh Gopalan, McGuireWoods LLP

    Ben Stacke, Faegre Drinker Biddle & Reath LLP

CORRESP
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    McGuireWoods LLP

    201 North Tryon Street

    Suite 3000

    Charlotte, NC 28202-2146

    Phone: 704.343.2000

    Fax: 704.343.2300

    www.mcguirewoods.com

    Rakesh Gopalan

    Direct: 704.343.2275

    rgopalan@mcguirewoods.com

    Fax: 704.805.5026

VIA EDGAR AND EMAIL

November 12, 2021

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.

    Draft Registration Statement on Form S-1

    Submitted October 18, 2021

    CIK No. 0001880613

On behalf of our client, Direct Digital Holdings, Inc.
(the “Company”), we submit this letter in response to comments from the staff (the “Staff”) of the
Securities and Exchange Commission (the “Commission”) contained in its letter dated October 29, 2021, relating
to the above-referenced Draft Registration Statement on Form S-1 (the “DRS”). This letter and a publicly filed
revised version of the Registration Statement (the “Registration Statement”) are being submitted with the Commission
via EDGAR concurrently. In addition to the electronic filing, we are delivering via email a copy of this letter, along with a courtesy
copy of the Registration Statement marked to indicate changes from the DRS confidentially submitted on October 18, 2021. In addition
to addressing the comments raised by the Staff in its letter, we have revised the Registration Statement to update other disclosures.

Each of our responses is set forth in
ordinary type beneath the corresponding Staff comment, which is set out in bold type. Except for page references appearing in
the headings and Staff comments below (which are references to the DRS submitted on October 18, 2021), the page references
in our responses are to pages in the Registration Statement.

Draft Registration Statement on Form S-1
submitted October 18, 2021

Unaudited Pro Forma Consolidated Financial Information

Unaudited Pro Forma Consolidated Balance Sheet, page 67

 1. In regard to your response to prior comment 6, we note in the event of a redemption election by the Continuing LLC Owners, Direct
Digital Holdings Inc. may effect a direct exchange of Class A common stock or make a cash payment. Since you will be controlled by
Direct Digital Management, LLC, the decision to redeem for cash will be made by them. Revise to present outside of pro forma permanent
equity the LLC Units to be held by Direct Digital Management, LLC or advise us.

Response:

The Company acknowledges the Staff’s comment
and respectfully advises the Staff that it has determined to remove the feature of the Direct Digital Holdings, LLC limited liability
company agreement that permits the Company to elect to make a cash payment for each LLC Unit redeemed. Accordingly, the Company believes
that under Accounting Standards Codification 480, the LLC Units held by Direct Digital Management, LLC are not redeemable at the option
of the holder thereof and accordingly that such LLC Units are properly characterized as permanent equity.

Atlanta
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Securities and Exchange Commission

Division of Corporation Finance

November 12, 2021

Page 2 of 2

 General

 2. We note your responses to prior comments 1 and 14 and that you have included in your prospectus graphics 2020 pro forma revenue
information and pro forma revenue growth. We also note that you intend to include in the prospectus graphics revenue information for the
required interim period when you publicly file the Form S-1. In light of the fact that the Orange 142 acquisition occurred on September 30,
2020, and the operations of Orange 142 are included within the fiscal year 2020 and interim 2021 financial statements, please remove the
pro forma revenue information from the prospectus graphics. If you choose to include financial information, include only financial information
from your consolidated financial statements. Furthermore, to present a balanced picture of the company’s financial health, provide
net income (loss) for the same periods with equal prominence. Refer to Securities Act Forms C&DI 101.02.

Response:

The Company acknowledges the Staff’s comment
and respectfully advises the Staff that it has removed all references to pro forma revenue information from the prospectus graphics.

Please
direct any questions regarding the Company’s responses or the Registration Statement to me at (704) 343-2275 or rgopalan@mcguirewoods.com.

    Very truly yours,

    MCGUIREWOODS LLP

    /s/ Rakesh Gopalan

    Rakesh Gopalan

    Partner

    cc:
    Mark Walker, Direct Digital Holdings, Inc.

    Keith Smith, Direct Digital Holdings, Inc.

    Susan Echard, Direct Digital Holdings, Inc.

    Phyllis Young, McGuireWoods LLP

    Stephen Older, McGuireWoods LLP

    Ben Stacke, Faegre Drinker Biddle & Reath LLP

United States securities and exchange commission logo
October 29, 2021
Mark Walker
Chief Executive Officer
Direct Digital Holdings, Inc.
1233 West Loop South, Suite 1170
Houston, TX 77027
Re:Direct Digital Holdings, Inc.
Amendment No. 2 to
Draft Registration Statement on Form S-1
Submitted October 18, 2021
CIK 0001880613
Dear Mr. Walker:
            We have reviewed your amended draft registration statement and have the following
comments.  In some of our comments, we may ask you to provide us with information so we
may better understand your disclosure.
            Please respond to this letter by providing the requested information and either submitting
an amended draft registration statement or publicly filing your registration statement on
EDGAR.  If you do not believe our comments apply to your facts and circumstances or do not
believe an amendment is appropriate, please tell us why in your response.
            After reviewing the information you provide in response to these comments and your
amended draft registration statement or filed registration statement, we may have additional
comments.  Unless we note otherwise, our references to prior comments are to comments in our
October 8, 2021 letter.
Draft Registration Statement on Form S-1 submitted October 18, 2021
Unaudited Pro Forma Consolidated Financial Information
Unaudited Pro Forma Consolidated Balance Sheet, page 67
1.In regard to your response to prior comment 6, we note in the event of a redemption
election by the Continuing LLC Owners, Direct Digital Holdings Inc. may effect a direct
exchange of Class A common stock or make a cash payment.  Since you will be controlled
by Direct Digital Management, LLC, the decision to redeem for cash will be made by
them.  Revise to present outside of pro forma permanent equity the LLC Units to be held
by Direct Digital Management, LLC or advise us.

 FirstName LastNameMark Walker
 Comapany NameDirect Digital Holdings, Inc.
 October 29, 2021 Page 2
 FirstName LastName
Mark Walker
Direct Digital Holdings, Inc.
October 29, 2021
Page 2
General
2.We note your responses to prior comments 1 and 14 and that you have included in your
prospectus graphics 2020 pro forma revenue information and pro forma revenue growth.
We also note that you intend to include in the prospectus graphics revenue information for
the required interim period when you publicly file the Form S-1. In light of the fact that
the Orange 142 acquisition occurred on September 30, 2020, and the operations of Orange
142 are included within the fiscal year 2020 and interim 2021 financial statements, please
remove the pro forma revenue information from the prospectus graphics.  If you choose to
include financial information, include only financial information from your consolidated
financial statements.  Furthermore, to present a balanced picture of the company’s
financial health, provide net income (loss) for the same periods with equal prominence.
Refer to Securities Act Forms C&DI 101.02.
            You may contact Claire DeLabar, Senior Staff Accountant, at (202) 551-3349 or Robert
Littlepage, Accounting Branch Chief, at (202) 551-3361 if you have questions regarding
comments on the financial statements and related matters.  Please contact Austin Pattan, Law
Clerk, at (202) 215-1319 or Kathleen Krebs, Special Counsel, at (202) 551-3350 with any other
questions.
Sincerely,
Division of Corporation Finance
Office of Technology
cc:       Rakesh Gopalan

United States securities and exchange commission logo
October 8, 2021
Mark Walker
Chief Executive Officer
Direct Digital Holdings, Inc.
1233 West Loop South, Suite 1170
Houston, TX 77027
Re:Direct Digital Holdings, Inc.
Draft Registration Statement on Form S-1
Submitted September 10, 2021
CIK 0001880613
Dear Mr. Walker:
            We have reviewed your draft registration statement and have the following comments.  In
some of our comments, we may ask you to provide us with information so we may better
understand your disclosure.
            Please respond to this letter by providing the requested information and either submitting
an amended draft registration statement or publicly filing your registration statement on
EDGAR.  If you do not believe our comments apply to your facts and circumstances or do not
believe an amendment is appropriate, please tell us why in your response.
            After reviewing the information you provide in response to these comments and your
amended draft registration statement or filed registration statement, we may have additional
comments.
Draft Registration Statement on Form S-1 Submitted September 10, 2021
Prospectus Summary, page 1
1.Please balance your disclosure of revenue growth in 2019 and 2020 with disclosure of
your net income (loss) for each of those periods.
2.Please disclose how you define small and mid-sized clients.
3.Please clarify whether there is a distinction between clients and customers. For example,
you state on page 5 that you had 150 direct customers on the buy-size but served 27,800
clients on the sell-side.

 FirstName LastNameMark Walker
 Comapany NameDirect Digital Holdings, Inc.
 October 8, 2021 Page 2
 FirstName LastName
Mark Walker
Direct Digital Holdings, Inc.
October 8, 2021
Page 2
Our Industry and Trends, page 3
4.Please use the same scale for the four graphs that present information about ad spending.
Our Competitive Strengths, page 6
5.Refer to your disclosure of Growing and Profitable Business Model on page 7.  Please
expand the disclosure to present the most directly comparable GAAP measure along with
your disclosure of Non-GAAP Adjusted EBITDA.  Please expand your disclosure of
Adjusted EBITDA on page 91 accordingly. Refer to Item 10(e)(1)(i)(A) of Regulation S-
K and Non-GAAP CD&I Question 102.10 for guidance.
Unaudited Pro Forma Consolidated Financial Information
Unaudited Pro Forma Consolidated Balance Sheet, page 67
6.In light of the LLC Unit redemption right, please tell us how you considered ASC 480-10-
S99-3 in determining that the Units should be presented as pro forma permanent equity.
In your response please address who makes the decision to redeem in cash rather than
Class A shares and tell us how this is within control of the Company.  In this regard, we
note on page 46 that you are considered a “controlled company.”
Management Discussion and Analysis of Financial Condition and Results of Operations , page
68
7.We note your disclosure that you have a 90% retention rate among the customers that
contribute to 80% of your revenue. Please disclose the time period you used to calculate
this measure. If this retention rate is for 2020, balance this disclosure by noting that your
top two customers accounted for 41% of your total revenue and that your top ten
customers account for 75% of your revenue.
8.Please describe and provide any related key metrics used for monitoring your ability to
retain customers, acquire new customers and expand sales to existing customers. For
example, we note that you highlight in your prospectus graphics the amount of revenue
per customer and average customer tenure for 2020. Tell us your consideration of
disclosing these or other metrics for each period presented and any related trends that
affect your revenues or results of operations. We refer you to Item 303(a) of Regulation S-
K and SEC Release No. 33-10751.
Components of Our Results of Operations, page 72
9.Please expand your disclosure to clarify how you generate revenues from each of your
segments.  For example, discuss the types of fee arrangements with buy-side clients and
the transactions that generate revenues for you in connection with your sell-side
operations.

 FirstName LastNameMark Walker
 Comapany NameDirect Digital Holdings, Inc.
 October 8, 2021 Page 3
 FirstName LastName
Mark Walker
Direct Digital Holdings, Inc.
October 8, 2021
Page 3
Results of Operations, page 73
10.We note on page 24 that your success is dependent on regularly adding new customers
and increasing your customers' usage of your platform.  We also note on page 74 that the
increase in sell-side advertising revenue was the result of bringing on more DSP
customers, as well as an overall increase in advertising spend by your customers.  Please
expand your discussion of buy-side and sell-side revenues to quantify the changes in
revenue from period to period due to new and existing customers.
11.We note on page 70 that clients often transition to your managed services delivery model,
which in turn drives higher profitability.  Please expand your discussion of revenues from
period to period to include any trends in revenues between self-service and managed
service for the segment revenues and the impact of such changes on profitability.
Principal Stockholders, page 109
12.Please disclose the natural persons who have voting or investment power over the Class A
and Class B shares to be held by USDM Holdings, Inc.
Financial Statements - Orange142, LLC, page F-45
13.Please provide unaudited financial statements for the corresponding interim period of the
preceding year pursuant to Rule 8-04 of Regulation S-X.
General
14.In the prospectus graphics following the prospectus cover page, you indicate that on the
buy-side, customer tenure averages 5.2 years based on the top 20 buy side customers by
2020 revenues. To provide context, disclose the percentage of total revenues attributable
to these top 20 customers. In addition, you indicate that the total number of clients for
Direct Digital Holdings as of June 30, 2021 was 27,950. Please revise to also disclose the
number of clients attributable to the buy-side versus the sell-side. Lastly, please balance
your presentation of revenue and revenue growth with the corresponding net income
(loss).
15.Please supplementally provide us with copies of all written communications, as defined in
Rule 405 under the Securities Act, that you, or anyone authorized to do so on your behalf,
present to potential investors in reliance on Section 5(d) of the Securities Act, whether or
not they retain copies of the communications.

 FirstName LastNameMark Walker
 Comapany NameDirect Digital Holdings, Inc.
 October 8, 2021 Page 4
 FirstName LastName
Mark Walker
Direct Digital Holdings, Inc.
October 8, 2021
Page 4
            You may contact Claire DeLabar, Senior Staff Accountant, at (202) 551-3349 or Robert
Littlepage, Accounting Branch Chief, at (202) 551-3361 if you have questions regarding
comments on the financial statements and related matters.  Please contact Austin Pattan, Law
Clerk, at (202) 215-1319 or Kathleen Krebs, Special Counsel, at (202) 551-3350 with any other
questions.
Sincerely,
Division of Corporation Finance
Office of Technology
cc:       Rakesh Gopalan