Core Insights - Orange 142, a division of Direct Digital Holdings, received two 2025 MarCom Awards for its digital marketing efforts with Emerald Isle Realty, achieving Gold for SEM Campaign and Platinum for Organic Social Media Strategy [1][2] Company Overview - Orange 142 is a digital marketing agency focused on mid-market brands, providing data-driven media execution across various channels including programmatic, search, social, and connected TV [5] - The agency specializes in high-growth sectors such as Travel & Tourism, Healthcare, Energy, and Financial Services, aiming to connect brands with valuable audiences [5] Campaign Performance - The integrated marketing campaigns led to a 19% increase in paid traffic and a 33% lift in total revenue for Emerald Isle Realty [3] - Direct bookings from organic social increased by 62%, while direct revenue driven by organic social saw an 81% increase, resulting in a 9,134% return on investment, which is up 32% year over year [3]

Core Insights - Orange 142, a division of Direct Digital Holdings, has launched a high-compliance practice aimed at advertisers in regulated industries such as energy, political, and governed consumer products, addressing the need for compliance and performance in complex regulatory environments [1][3] Group 1: New Practice Overview - The new practice leverages Orange 142's adtech stack, which includes compliance-aligned supply paths, privacy-safe targeting, and transparent ROI-driven measurement, combining advanced AI capabilities with high-touch client service [2] - This initiative aims to provide a more efficient and accountable media-buying approach for regulated verticals, setting Orange 142 apart in a competitive market [2] Group 2: Client Support and Compliance - Orange 142 will assist clients in defining category-specific requirements, establishing activation rules, and aligning measurement practices with regulatory expectations, ensuring compliance in audience targeting, data handling, disclosures, and message review [3] - The practice is designed to offer clients a predictable and transparent framework, enabling them to act swiftly without compromising compliance or performance [3][4] Group 3: Market Demand and Future Plans - There is a growing demand for clarity in regulated industries regarding campaign approval processes and result measurement, which the new offering aims to address [4] - The new service is available immediately, with additional guidance, vertical insights, and activation playbooks expected to roll out in early 2026 [4]

Form S-1 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 1 to As filed with the Securities and Exchange Commission on November 17, 2025. Registration Statement No. 333-291106 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Direct Digital Holdings, Inc. (Exact name of registrant as specified in its charter) (State or Other Jurisdiction of Incorporation or Organization) (Primary Standard Industrial Classification Code Number) Delaware 7370 87-2306185 (I.R.S. Emplo ...

Revenue Performance - Buy-side revenue increased 7% to $7.3 million in Q3 2025, compared to $6.8 million in Q3 2024, representing the majority of consolidated revenue[15] - Sell-side revenue decreased to $600,000 in Q3 2025 from $2.2 million in Q3 2024, primarily due to lower impression inventory[15] - The number of customers increased by 5%, but revenues declined by 70%, highlighting challenges in the sell-side[36] Financial Metrics - Gross margin for Q3 2025 was 28%, down from 39% in Q3 2024[16] - Operating expenses decreased by 25% to $6.1 million in Q3 2025, compared to $7.2 million in the same period last year[16] - Year-to-date operating expenses reduced by $5.4 million, approximately a 20% decrease compared to the first nine months of 2024[14] - Net loss improved to $5 million or $0.24 per share in Q3 2025, compared to a net loss of $6.4 million or $0.71 per share in Q3 2024[18] - Total cash plus accounts receivable as of September 30, 2025, was $4.5 million, down from $6.4 million at the end of 2024[18] Debt and Equity Management - Successfully converted $25 million of existing debt into Series A convertible preferred stock, enhancing financial flexibility[19] - Expanded equity line of credit facility to $100 million, raising $8.9 million since its inception in November 2024[20] - The company completed a $10 million conversion of debt to preferred equity, indicating a positive shareholder equity position post-quarter[39] Strategic Initiatives - New partnership with ReachTV aims to enhance data-driven marketing for travel and tourism, reaching over 50 million travelers per month[7] - The company expects 2026 to be a positive cash flow year, driven by optimization opportunities and a focus on the buy-side business[34] - The buy-side business remains profitable, while the sell-side is being streamlined to improve overall profitability[35] - AI initiatives are enabling growth on the sell-side without significantly increasing fixed costs[38]

Group 1: RLX Technology Inc - RLX Technology Inc reported quarterly earnings of 3 cents per share on sales of $158.600 million [1] - Shares of RLX Technology rose 6% to $2.47 in pre-market trading following the earnings report [1] Group 2: Other Stocks in Pre-Market Trading - Cidara Therapeutics, Inc. surged 92% to $203.50 after a Schedule 13D Amendment revealed beneficial ownership of 3.37 million shares [4] - Binah Capital Group, Inc. gained 52.2% to $2.17 after posting stronger-than-expected third-quarter results [4] - Expion360 Inc. rose 42.4% to $1.81 following its third-quarter results [4] - Aspire Biopharma Holdings, Inc. surged 31.2% to $0.1380 in pre-market trading [4] - Invivyd, Inc. gained 28.8% to $2.28 after reporting better-than-expected third-quarter financial results [4] - Milestone Scientific Inc. surged 26.3% to $0.4801 after reporting better-than-expected third-quarter sales [4] - Lazydays Holdings, Inc. gained 23.3% to $1.85 after a previous surge [4] - Omeros Corp gained 12.5% to $7.08 following a narrower-than-expected quarterly loss [4] - Nouveau Monde Graphite Inc rose 10% to $3.25 after a decline the previous day [4] Group 3: Declining Stocks in Pre-Market Trading - TSS Inc tumbled 40.2% to $9.10 after reporting a year-over-year decrease in third-quarter results [4] - enVVeno Medical Corp declined 35.8% to $0.42 after an unfavorable FDA appeal decision [4] - Nuvve Holding Corp fell 29.3% to $0.34 after announcing third-quarter results [4] - ESS Tech Inc shares dipped 24.2% to $3.22 after reporting weak quarterly sales [4] - Direct Digital Holdings Inc fell 18.8% to $0.23 after a significant gain the previous day [4] - StubHub Holdings Inc fell 18.8% to $15.28 after worse-than-expected third-quarter EPS results [4] - Mangoceuticals Inc dipped 17.7% to $0.98 after a decline the previous day [4] - Red Cat Holdings Inc dipped 15.1% to $6.57 after worse-than-expected financial results and a lowered FY25 sales guidance [4] - WhiteFiber Inc fell 13.4% to $17.21 after reporting worse-than-expected financial results [4] - Sobr Safe Inc fell 12.4% to $2.21 after a decline the previous day [4]

Financial Performance - Total revenues for the three months ended September 30, 2025, were $7,984,000, a decrease of 12% compared to $9,075,000 for the same period in 2024[10] - Gross profit for the nine months ended September 30, 2025, was $8,169,000, down from $14,444,000 in 2024, reflecting a decline of 43%[10] - The net loss attributable to Direct Digital Holdings, Inc. for the three months ended September 30, 2025, was $2,680,000, compared to a net loss of $2,690,000 in the same period of 2024[10] - For the nine months ended September 30, 2025, the net loss was $15.136 million, compared to a net loss of $13.338 million for the same period in 2024, representing an increase in loss of approximately 13.5%[19] - The company reported a total operating loss of $1.091 million for the three months ended September 30, 2025, compared to an operating income of $1.1 million for the same period in 2024[124] - The net loss attributable to Class A shareholders for the three months ended September 30, 2025, was $3.043 million, compared to a loss of $2.690 million in 2024, reflecting an increase in loss of approximately 13%[128] Assets and Liabilities - Total current assets decreased to $6,603,000 as of September 30, 2025, down from $8,535,000 at the end of 2024, representing a decline of 23%[8] - Total liabilities decreased to $29,230,000 as of September 30, 2025, compared to $45,736,000 at the end of 2024, a reduction of 36%[8] - The company reported cash and cash equivalents of $871,000 as of September 30, 2025, down from $1,445,000 at the end of 2024, a decrease of 40%[8] - The accumulated deficit increased to $16,058,000 as of September 30, 2025, from $8,774,000 as of December 31, 2024, indicating a worsening financial position[8] - Total long-term debt as of September 30, 2025, was $16.3 million, down from $41.2 million as of December 31, 2024[68] Operating Expenses - Operating expenses for the nine months ended September 30, 2025, were $18,429,000, a decrease of 20% compared to $22,973,000 in 2024[10] - Operating expenses for the three months ended September 30, 2025, were $6,125,000, down from $7,172,000 in the same period of 2024, indicating a decrease of approximately 15%[10] - The company incurred corporate office expenses of $4.961 million for the three months ended September 30, 2025, significantly higher than $0.247 million in the same period of 2024[125] Stock and Equity - The company issued 25,000 shares of Series A Convertible Preferred Stock, raising $21,220,000 net of issuance costs[12] - The company raised $6.708 million from the issuance of Class A Common Stock during the nine months ended September 30, 2025[19] - The Series A Convertible Preferred Stock was established with a total amount of $25.0 million, carrying a cumulative dividend rate of 10% per annum[101][103] - The balance of Class A Common Stock increased to 3,795,199 units as of September 30, 2024, from 3,478,776 units at the end of 2023, representing a growth of 9.1%[16] Revenue Recognition - Revenue from the sell-side advertising segment is generated through the sale of digital ad units, while the buy-side segment focuses on managed advertising campaigns[28] - The Company recognized revenue on a gross basis, inclusive of all supplier costs, for both sell-side and buy-side advertising segments[30] - The Company’s revenue recognition follows a five-step process, primarily derived from sell-side and buy-side advertising[27] - The Company generated revenue from both sell-side and buy-side advertising, with the latter focusing on managed advertising campaigns and data services[28] Cash Flow and Liquidity - The company utilized $7.036 million in operating activities for the nine months ended September 30, 2025, which is slightly lower than the $7.095 million used in the same period of 2024[19] - As of September 30, 2025, cash and cash equivalents were $0.9 million, raising substantial doubt about the company's ability to continue as a going concern[63] - The company anticipates liquidity sources from cash flow from operations and potential sales of equity or debt securities[65] Debt and Financing - The Company entered into a Term Loan and Security Agreement with a principal amount of up to $32.0 million, consisting of a $22.0 million closing date term loan and a $10.0 million delayed draw term loan[69] - The Company entered into a Credit Agreement with East West Bank for a revolving credit facility of up to $10.0 million, maturing on July 7, 2025[82] - The Company made prepayments totaling $1.0 million upon execution of the Third EWB Amendment, with additional prepayments of $1.0 million by January 15, 2025, and $2.0 million by April 15, 2025[86] Customer Concentration - Two customers accounted for 30% of revenues for the three months ended September 30, 2025, while one customer accounted for 12% of revenues for the same period in 2024[47] Strategic Initiatives - The company has a plan to reduce expenses through staff reductions and cost-saving measures, executed on July 1, 2024[65] - The company completed the unification of its buy-side businesses, Orange 142 and Huddled Masses, in October 2024, aiming to enhance its advertising solutions[21]

Core Insights - Direct Digital Holdings, Inc. reported a quarterly loss of $0.24 per share, which was worse than the Zacks Consensus Estimate of a loss of $0.16, but an improvement from a loss of $0.71 per share a year ago [1] - The company posted revenues of $7.98 million for the quarter ended September 2025, missing the Zacks Consensus Estimate by 44.94% and down from $9.07 million year-over-year [2] - Direct Digital shares have declined approximately 79.5% year-to-date, contrasting with the S&P 500's gain of 15.6% [3] Financial Performance - The earnings surprise for the recent quarter was -50.00%, while the previous quarter saw a positive surprise of +76.04% with an actual loss of $0.23 against an expected loss of $0.96 [1][2] - Over the last four quarters, the company has only surpassed consensus EPS estimates once [2] Future Outlook - The current consensus EPS estimate for the upcoming quarter is -$0.17 on revenues of $19 million, and for the current fiscal year, it is -$0.90 on revenues of $51.8 million [7] - The estimate revisions trend for Direct Digital was mixed ahead of the earnings release, resulting in a Zacks Rank 3 (Hold), indicating expected performance in line with the market [6] Industry Context - The Advertising and Marketing industry, to which Direct Digital belongs, is currently in the top 41% of over 250 Zacks industries, suggesting a favorable outlook compared to the bottom 50% [8]

Financial Data and Key Metrics Changes - Consolidated revenue for Q3 2025 was $8 million, down from $9.1 million in Q3 2024, reflecting a decline in overall revenue [12] - Sell-side revenue decreased to $600,000 from $2.2 million in the same period last year, primarily due to lower impression inventory [12] - Buy-side revenue increased by approximately 7% to $7.3 million compared to $6.8 million in Q3 2024 [12] - Gross margin for Q3 2025 was 28%, down from 39% in Q3 2024 [12] - Operating expenses decreased by 25% to $6.1 million from $7.2 million in the prior year [13] - Total operating loss for Q3 was $3.9 million, slightly worse than the loss of $3.7 million in Q3 2024 [13] - Net loss improved to $5 million or $0.24 per share, compared to a net loss of $6.4 million or $0.71 per share in Q3 2024 [13] - Adjusted EBITDA for Q3 was a loss of $3 million, consistent with the loss of $2.9 million in the prior year [14] Business Line Data and Key Metrics Changes - The buy-side segment saw a revenue increase of 7% to $7.3 million, which constituted the majority of consolidated revenue [5] - The sell-side segment faced challenges with revenue significantly impacted by lower engagement levels and impression inventory [6] Market Data and Key Metrics Changes - The company is focusing on rebuilding publisher relationships and onboarding new customers in the sell-side segment [6] - The partnership with Reach TV aims to enhance inventory and data targeting for the buy-side business, reaching over 50 million travelers monthly [5] Company Strategy and Development Direction - The company is adopting a dual approach by leveraging its unique position in both buy-side and sell-side operations to create integrated solutions [6] - AI is being utilized to drive innovation and operational efficiencies, with a nearly 40% growth in feature sets due to new AI modules [9] - The company aims to minimize costs while driving growth, with a long-term goal of returning to strong year-over-year revenue growth [11] Management's Comments on Operating Environment and Future Outlook - Management acknowledged the challenges faced in the sell-side business but remains committed to rebuilding and growing the business [11] - The company anticipates 2026 will be a positive cash flow year, driven by optimization opportunities and a focus on the profitable buy-side business [33] Other Important Information - The company successfully converted $25 million of existing debt into Series A convertible preferred stock, improving its equity position [14] - An additional $10 million debt-to-equity conversion was completed post-quarter-end, enhancing financial flexibility [15] - The equity line of credit facility was expanded to $100 million, providing additional financing capacity [16] Q&A Session Summary Question: Concerns about sell-side results and integration with DSPs - Management sees a combination of traditional business models and ecosystem platform play as viable paths for growth [20] Question: Impact of platform approach on buy-side outreach - Advertisers in alpha testing have responded favorably to the new platform approach, seeing benefits in performance and ROAS [23] Question: Details on the Orange 142 and Reach TV partnership - The partnership is viewed as strategic, complementing existing advertisers and enhancing the company's offerings in the travel sector [25] Question: Revenue from new verticals and customer attrition - The company is focusing on larger customers in new verticals to reduce churn and improve stability [29] Question: Inflection point towards positive cash flow - Management believes 2026 will be a positive cash flow year, with ongoing optimization efforts in the sell-side business [33] Question: Focus on buy-side versus sell-side - The sell-side is seen as important for overall profitability due to favorable operating leverage once past the break-even point [34] Question: Current status of shareholder equity - The company believes it is now positive in shareholder equity following recent debt conversions [38]

Core Insights - Direct Digital Holdings reported a 7% increase in buy-side revenue for Q3 2025 compared to Q3 2024, reaching $7.3 million, while consolidated revenue decreased by 12% to $8.0 million [1][12] - The company successfully reduced operating expenses by 15% in Q3 2025 and 20% for the first nine months of 2025 compared to the prior year [1][12] - The sell-side segment faced challenges with revenue dropping significantly due to lower impression inventory and engagement levels [3][12] Financial Performance - Buy-side advertising revenue increased by 7% from $6.9 million in Q3 2024 to $7.3 million in Q3 2025 [12] - Sell-side advertising revenue fell from $2.2 million in Q3 2024 to $0.6 million in Q3 2025, a decrease of 73% [12] - Gross profit for Q3 2025 was $2.2 million, representing 28% of revenue, down from 39% in Q3 2024 [12] - Operating loss for Q3 2025 was ($3.9 million), slightly worse than the ($3.7 million) loss in the prior year [12] Strategic Initiatives - The company is focusing on evolving into an AI-first organization, enhancing operational efficiency and developing new customer solutions [4][8] - Direct Digital Holdings is actively exploring strategic opportunities to support growth initiatives and enhance shareholder value [5][8] - The buy-side segment served approximately 220 customers in Q3 2025, with $2.1 million of revenue coming from new verticals [12] Capital Structure - The company issued $25 million of Series A Convertible Preferred Stock at a conversion price of $2.50 per share [6] - An additional $10 million of Series A Convertible Preferred Stock was issued on October 14, 2025 [7] - As of September 30, 2025, cash and cash equivalents were $0.9 million, down from $1.4 million at the end of 2024 [12]

Core Points - Direct Digital Holdings, Inc. has expanded its Equity Reserve Facility capacity from $20 million to $100 million, reflecting a strategic move to enhance liquidity and support business growth [1][2][3] - The proceeds from the sale of Class A Common Stock are intended for general corporate purposes, indicating a focus on operational flexibility and capital management [3][4] Group 1 - The amendment to the Share Repurchase Agreement with New Circle Capital allows for a total capacity of $100 million in gross proceeds [2] - CEO Mark Walker emphasized the importance of this expansion as a good capital management strategy to optimize access to capital and strengthen the balance sheet [3] - The company has filed a Form 8-K with the SEC for further details regarding the amendment [4] Group 2 - Direct Digital Holdings operates through its subsidiaries, Colossus Media, LLC and Orange 142, LLC, providing advertising and marketing technology solutions [1][10] - The company focuses on delivering data-driven digital media strategies for brands, agencies, and publishers, enhancing reach and performance across various platforms [10][11] - The company aims to humanize technology by providing dedicated support and tailored digital marketing solutions, generating billions of monthly impressions [11]