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Investor Presentation November 2025 INVESTOR PRESENTATION
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FORWARD-LOOKING STATEMENTS AND NON-GAAP FINANCIAL MEASURES This presentation contains, and our other communications may contain, forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended. These statements can be identified by the fact that they do not relate strictly to historical or current facts. Forward-looking statements, written, oral or otherwise made, represent the Company’s expectation or belief concerning future events. All forward-looking statements are subject to assumptions, risks, and uncertainties, which may change over time and many of which are beyond our control. The forward-looking statements contained in this presentation include statements related to the Company’s current views and expectations with respect to its future performance and operations and other anticipated future events and expectations that are not historical facts. By nature, forward-looking statements involve risks and uncertainties that could cause actual results to differ materially from those projected or implied by the forward-looking statement. Forward-looking statements are based on current expectations and assumptions and currently available data and are neither predictions nor guarantees of future events or performance. You should not place undue reliance on forward-looking statements, which speak only as of the date hereof. Some of the factors that may cause actual results or other future events, circumstances, or aspirations to differ from those in forward-looking statements are described in the sections entitled “Risk Factors” and “Forward-Looking Statements” included in our Annual Report on Form 10-K, 10-K/A or other applicable documents that are filed or furnished with the Securities and Exchange Commission (“SEC”). We do not undertake to update any forward-looking statement to reflect the impact of events, circumstances, or results that arise after the date that the statement was made. You, however,should consult further disclosures (including disclosures of a forward- looking nature) that we may make in any subsequent Annual Report on Form 10-K, Quarterly Report on Form 10-Q, Current Report on Form 8-K, or other applicable document that is filed or furnished with the SEC, or in any document posted to the “Investors” section of the Company’s website. The unaudited estimates and statements included herein are the opinion of management and represent estimates and expectations based on the most current information available. While we believe that our assumptions are reasonable, we caution that it is very difficult to predict the impact of known factors and it is impossible for us to anticipate all factors that could affect our actual results. Our actual results may differ materially from these estimates due to the completion of our financial closing procedures, final adjustments and other developments that may arise between now and the time the financial results for our fourth quarter are finalized. This preliminary financial data has been prepared by and is the responsibility of management. Our independent registered public accounting firm, BDO USA, LLP ,has not audited, reviewed, compiled or performed any procedures with respect to the accompanying preliminary financial data. Accordingly,BDO USA, LLP does not express an opinion or any other form of assurance with respect thereto. As a result of the foregoing considerations and limitations, investors are cautioned not to place undue reliance on this projected financial information. This presentation includes non-GAAP financial measures within the meaning of the federal securities laws, including Adjusted EBITDA and Adjusted EBITDA (Excluding Political). We define Adjusted EBITDA as net income (loss) before the deduction of income taxes, interest expense, net, loss (gain) on repurchases, extinguishment and modification of debt, transaction costs, depreciation and amortization, stock-based compensation, business realignment costs, impairments, change in fair value of investment, net (income) loss from discontinued operations, net of income taxes, net loss (gain) on sale and retirement of assets and other expense (income) net. We define Adjusted EBITDA (Excluding Political) as Adjusted EBITDA less political net revenue, net of a fifteen percent deduction to account for estimated national representative firm fees, music licensing fees and sales commissions expense. Adjusted Operating Income by segment, Adjusted EBITDA, and Adjusted EBITDA (Excluding Political) do not represent, and should not be considered as alternatives to, net income or cash flows from operations as determined under U.S. generally accepted accounting principles, or GAAP. Reconciliations of certain of these measures to net income are included in the Appendix of this presentation and in Exhibit 99.1 to our Current Report on Form 8-K filed with the SEC on November 10, 2025. 2
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3 IS A COMMUNITY-FOCUSED DIGITAL AND BROADCAST MEDIA AND DIGITAL MARKETING SOLUTIONS COMPANY PRINCIPALLY FOCUSED OUTSIDE THE TOP 50 MARKETS IN THE UNITED STATES Townsquare Ignite, our robust digital advertising division, specializes in helping businesses of all sizes connect with their target audience through data-driven, results based strategies, by utilizing a) our proprietary digital programmatic advertising technology stack with an in-house demand and data management platform and b) our owned and operated portfolio of more than 400 local news and entertainment websites and mobile apps along with a network of leading national music and entertainment brands, collecting valuable first party data. Townsquare Interactive, our subscription digital marketing services business, partners with SMBs to help manage their digital presence by providing a SAAS business management platform, website design, creation and hosting, search engine optimization and other digital services. And through our portfolio of local radio stations strategically situated outside the Top 50 markets in the United States, we provide effective advertising solutions for our clients and relevant local content for our audiences
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$439M / $98M LTM 9/30/25 Net Revenue/ Adjusted EBITDA 45M / 11M Total Digital / Broadcast Audience(1) ~4x Digital Audience to Radio Audience AN INTRODUCTION TO TOWNSQUARE (NYSE: TSQ): FACTS & STATS KEY STATS 4 102% / 95% LTM 9/30/25 Net Revenue / Adjusted EBITDA as % of FY 2019 $238M LTM 9/30/25 Digital Net Revenue 18% / 27% % of LTM 9/30/25 Total Revenue and Adjusted EBITDA from Digital Subscription Solutions (Townsquare Interactive)(2) 54% / 53% LTM 9/30/25 Net Revenue / Segment Profit from Digital Note: Please refer to page 2 for definitions of non -GAAP measures. 1. Total digital audience represents average monthly global UVs on Townsquare’s owned and operated websites in the nine months ended September 30, 2025 per Google Analytics. Total broadcast audience represents the average of Townsquare’s Fall 2024 and Spring 2025 nationwide cume, P12+ M-Su 6a -6a, per Act 1 Systems (based on Nielsen data). 2. Excluding political revenue. 3. Townsquare’s Board of Directors approved a quarterly dividend payment of $0.20 per share, payable on January 26, 2026 to shareholders of record as of February 2, 2026. ▪ Townsquare is a community-focused digital and broadcast media and digital marketing solutions company, principally focused on hundreds of underserved small and mid- sized local markets outside the Top 50 markets across the U.S. ▪ Strong and fast-growing digital businesses with profitable revenue streams supported by mature “cash cow” local radio broadcast business with very strong cash flow characteristics ▪ Townsquare has invested in world-class technology and infrastructure to serve a broad base of local businesses and engage our loyal audiences and communities ▪ Presence and disciplined focus outside the Top 50 markets is a competitive advantage given the greater need for local content in markets outside the largest U.S. cities, and a much weaker digital competitive landscape ▪ Townsquare has successfully transformed into a Digital First Local Media Company, with 55% of all profit and revenue in September YTD’25 sourced and generated from our digital advertising divisions and our recurring subscription digital marketing solutions, which are greatly differentiated in TSQ’s markets vs. local digital agencies or other competitors ▪ Townsquare’s local communities turn to our local trusted media brands to stay informed and to be entertained ▪ Our digital audience to our owned and operated properties and brands is ~4x the size of our terrestrial radio audience ▪ Approximately 18% of our total net revenue(2) is monthly, recurring subscription digital marketing revenue $0.20 / ~13% +1% YoY Increase Announced in March 2025 Quarterly Dividend Per Share, $0.80 Per Share on an Annualized Basis(3) Representing ~13% Dividend Yield as of November 7, 2025
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TOWNSQUARE’S TRANSFORMATION From local, ingrained teams in 13 local markets to 74 local markets From Nearly 100% Radio Revenue/Profit to 50%+ Digital Revenue/Profit From <1M UVs per Month to 45M UVs Per Month From No Social Platform to 44M Social Media Followers From No Video Platform to 4B+ YouTube Lifetime Views From A Pure Radio Broadcast Company to a Digital First Local Media Company From 2010 → To Q3 2025 5 From No First-Party Data Platform to a Robust Platform with 24 million unique identifiers From No Broadcast Attribution to ~1,400 campaigns measured by Townsquare Analytics From 100% Broadcast Only Clients to >70% of Broadcast Clients Also Buying Digital Solutions
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Note: Please refer to page 2 for definitions of non -GAAP measures. TSQ also has $8M of Other (live events) revenue in the twelve mont hs ended September 30, 2025. 1. Excludes broadcast political revenue of $8M, and total political revenue of $8M. 2. See slide 15. TOWNSQUARE: A VIEW FROM THE TOP $238M $64M 27% 54% / 53% LTM 9/30/25 Net Revenue LTM 9/30/25 Net Revenue / Segment Profit Contribution LTM 9/30/25 Net Revenue (1) LTM 9/30/25 Segment Profit Margin (1) 341 Local Radio Stations DIGITAL BROADCAST LTM 9/30/25 Segment Profit Margin $185M $50M 27% 43% / 44% LTM 9/30/25 Net Revenue / Segment Profit Contribution (1) Reach 1 out of 2 Adults (50%) via our AM/FM in each local market 6 LTM 9/30/25 Segment Profit LTM 9/30/25 Segment Profit (1) Subscription Digital Marketing Solutions $32B Total Addressable Market (2) LTM 9/30/25 Net Revenue LTM 9/30/25 Segment Profit Digital Advertising Owned & Operated Digital Brands Data Analytics & Management Platform Digital Programmatic Technology Platform $162M $39M $76M $24M LTM 9/30/25 Net Revenue LTM 9/30/25 Segment Profit Mature, “Cash Cow” Business
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WE ARE A DIGITAL FIRST LOCAL MEDIA COMPANY AND DIGITAL IS OUR GROWTH ENGINE • Beginning with our YE 2021 reporting, we re -segmented our business to better align with how we view our Company and our strategy today • Provides greater visibility of the profitability of our digital businesses, and the mature, cash cow characteristics of our broadcast business • Provides relevant data to allow a sum-of-the-parts valuation for our high growth and subscription-based digital businesses Segment Net Revenue ($M) Segment Profit ($M) 7 Sep YoY % of Sep YoY % of YTD'25 Growth % Total YTD'25 Growth % Total Margin% Digital Advertising $119.5 2.6% 37% $27.4 (5.0%) 33% 23% Subscription Digital Marketing Solutions 56.4 1.1% 18% 18.6 19.4% 22% 33% Total Digital 176.0 2.1% 55% 46.1 3.6% 55% 26% Broadcast Advertising 137.6 (10.8%) 43% 37.0 (13.5%) 44% 27% Other (Live Events) 7.3 11.6% 2% 0.4 (261%) 1% 6% Total $320.9 (3.7%) 100% $83.5 (4.0%) 100% 26%
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− Very limited focus from larger media players, digital marketing solutions providers, and digital programmatic providers in our size markets outside the Top 50 TOWNSQUARE IS THE ONLY LOCAL MEDIA COMPANY SOLEY FOCUSED ON MARKETS OUTSIDE THE TOP 50 More Attractive Competitive Landscape 8 1. Source: Kristen Hare, ‘More than 90 local newsrooms closed during the coronavirus pandemic’, Poynter [website], https://www.poynter.org/locally/2021/the -coronavirus-has-closed-more-than-60-local-newsrooms-across-america-and-counting/, (accessed October 20, 2021). − Talented Local Sales Teams in each of our 74 local media markets with strong long-term community relationships − Often the largest media sales team in the local market − World-class Inside Sales Team (~85 sellers) in Charlotte and Phoenix to focus on under-served digital markets with population less than 1.5 million people outside the Top 50 markets and outside of our local media markets Large, Trusted Local Sales Team & Inside Sales Team Leading Presence in 74 Small & Mid-Sized Markets – Portfolio of 400+ local community websites, 380 mobile apps, and 341 radio stations – AM/FM broadcast alone reaches 50% of adults in our local markets – Healthy, stable markets with lower economic volatility and stabilizing institutions such as universities, military installations and state capitals – Average market population of ~300,000 people Filling the Content Void in Markets Outside the Top 50 − Starved for high quality local digital content given the retrenchment of newspapers in these markets − Since 2004, approximately 2,100 newspapers have closed in the U.S., and more than 100 local newsrooms closed during the pandemic (1) − Our On-Air DJs are Digital Content Creators & Local Social Influencers, creating approximately 20,000 pieces of local content each and every month - one of the largest producers of local content in the United States 1. 1. Source: UNC Hussman School of Journalism and Media, ‘Where Have Newspapers Disappeared?’ [website], https://www. https://w ww.usnewsdeserts.com/#1536249049294 -115f3533-f5e9, (accessed March 11, 2025).
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BEING A DIGITAL FIRST LOCAL MEDIA COMPANY IS THE RIGHT POSITION TO BE IN • In 2024, radio advertising was ~4% of all advertising dollars spent in the United States, while digital advertising solutions contributed ~70% • Radio is a mature and cash flow generative business – a quintessential “cash cow” business • It is estimated that digital advertising will grow to 80% of all advertising spend in 2029 • As a Digital First Local Media Company , TSQ’s growth engine has and will continue be digital Source: 2024 S&P Global Market Intelligence. 'Advertising Expenditure Forecasts,’ December 2024. Advertising expenditure and related data provided by Magna Global, 2024. 2024 2025 2026 2027 $268 $295 +10%+16% $323 +10% $352 +9% $381 +8% FORECASTED U.S. DIGITAL AD SPEND ($B) FORECASTED U.S. AD SPEND IN 2029 80% 11% 3%3%2% 0% Digital Television Radio Print Outdoor Cinema 9 $410 +8% 2028 2029
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Digital revenue has grown +13% YoY Since 2016 (2016-2024 CAGR) and +2% September YTD 2025 TOWNSQUARE DELIVERS CONSISTENT DIGITAL REVENUE GROWTH 2016 2017 2018 2019 2020 2021 $88M $100M +13% $124M +24% $159M +28% $167M +5%* *COVID year $199M +19% Note: Digital revenue includes the Subscription Digital Marketing Solutions segment and the Digital Advertising segment. 10 $231M +16% 2022 $232M +1% 2023 $234M +1% 2024
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TOWNSQUARE DIGITAL REVENUE VS LOCAL MEDIA INDUSTRY 24% 35% 55% 15% 21% 23% 54% DIGITAL AS % OF TOTAL REVENUE 11 Note: YTD September 2025 Digital as % of Total Revenue per Company filings for Townsquare, Cumulus and Saga. YTD June 2025 for iHeart and Beasley. YTD June 2024 for Audacy. For Lee Enterprises, represents the six months ending June 29, 2025.
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DIGITAL ADVERTISING (Townsquare Ignite) Our Digital Advertising segment’s products and solutions are a combination of our owned and operated digital properties, our proprietary digital programmatic advertising platform, and an in-house demand and data management platform collecting valuable proprietary first-party data, and is the fastest growing revenue and profit driver of Townsquare ▪ As an at-scale, large, digital content publisher, we are able to collect valuable first-party data on our audience (we do not rely 100% on third-party data sources) ▪ Proprietary advertising technology platform, with in-house, demand-side buying platform (DSP) ▪ Integrated with 15+ digital advertising buying platforms ▪ Access to all major advertising exchanges and mobile apps ▪ Access to >250 billion impressions/day ▪ Hyper-targeted solutions and white glove customer service ▪ Delivered across desktop, mobile, apps, connected TV, email, paid search, and social media platforms utilizing display, video, and native executions ▪ Full-service design and creative team to assist clients in crafting the right message and developing and building the creative for the campaign 400+ Local Websites 10 National Websites Note: As of September 30, 2025 unless otherwise noted. 1. Represents % of Digital Advertising segment revenue. 2. Represents average monthly global unique visitors (“ UVs “) on our owned and operated websites in the nine months ended September 30, 2025 per Google Analytics. 380 Mobile Apps ~45M Monthly UVs (2) 44M Social Followers 4.6B YouTube Lifetime Views Collect and analyze first-party data from our Owned & Operated portfolio of websites and apps (and then overlay with third-party data) Leads to detailed insights about consumer behaviors, audience interest, and purchase intent $39M LTM 9/30/25 Segment Profit (~24% profit margin) $162M LTM 9/30/25 net revenue (~37% of TSQ’s net revenue) OWNED & OPERATED PLATFORM (~40% OF REVENUE)(1) PROGRAMMATIC PLATFORM (~60% OF REVENUE)(1) DATA ANALYTICS & MANAGEMENT PLATFORM 24M USER PROFILES 12 2011 2016 Sep YTD 2025 1M 37M 45M *Average Monthly Unique Visitors on TSQ’s Owned and Operated Websites >40x Audience Growth Since 2011 ▪ Proprietary website / app platforms and in-house Content Management System (CMS)
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LOOKING DEEPER: O&O DIGITAL ADVERTISING ~40% of our Digital Advertising revenue comes from our Owned & Operated platform, composed of: ▪ Direct Sales (Social, Video, Display, Email etc.) ▪ Indirect Sales (Display) ▪ Online Radio (Streaming) Note: Represents year-over-year growth rates. 1. As reported by the Press Gazette. 2. Represents average monthly global unique visitors (“ UVs “) on our owned and operated websites in the three months ended September 30th per Google Analytics. DIRECT SALES (~11% OF 2024 DIGITAL ADVERTISING REVENUE) 13 ▪ Sales made by our feet-on-the-street sales team of social, video, display, etc. advertising on our local and national owned and operated digital platform ▪ Strong local growth, +10% in Q3’25 and September YTD’25 ▪ National continues to decline, but is a smaller piece of direct sales ▪ Total Direct Sales of O&O Digital Advertising is +6% in Q3’25 and +5% in September YTD’25 INDIRECT SALES (~13% OF 2024 DIGITAL ADVERTISING REVENUE) ▪ Sales of the remnant inventory on our local and national owned and operated digital platform sold programmatically ▪ Have experienced significant declines due to declines in search referral traffic, and therefore online audience, due to the explosion of AI ▪ Declines in audience translates to declines in the indirect revenue related to our remnant inventory ▪ Local -55% in Q3’25 and -34% in September YTD’25 ▪ National -30% in Q3’25 and -32% in September YTD’25 ▪ Total Indirect Sales of O&O Digital Advertising is -50% in Q3’25 (-$2.5M) and -34% in September YTD’25 (-$5.2M) 2025 vs. 2024 % of Total $ in millions Q3'24 Q3'25 % $ Q3'24 Q3'25 Direct $4.2 $4.5 6% $0.3 30% 38% Indirect $5.0 $2.5 (50%) ($2.5) 36% 21% Online Radio $4.8 $4.8 1% $0.0 34% 41% Total O&O $14.0 $11.8 (16%) ($2.2) 100% 100% Q3 2023 41M 41M 21M Local UVs(2) National UVs (2) Q3 2024 Q3 2025 Q3 2023 18M 14M 7M Q3 2024 Q3 2025 +1% -49% -35% -48% Declining search referral traffic is an industry-wide issue: in August 2025, 45 of the top 50 US news websites experienced YoY declines in search traffic (1)
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TOWNSQUARE INTERACTIVE: ORGANICALLY BUILT SUBSCRIPTION DIGITAL MARKETING SOLUTIONS 1. Subscription profit refers to TSI’s Segment. Profit 100% owned, subscription-based business that provides an all-in-one SAAS solution that provides a suite of digital marketing services to underserved SMBs Dedicated Inside Sales Team of ~85 sellers that prospect small to mid-sized markets across the U.S. outside the Top 50 markets Additionally, leverage our Local Media Sales Teams trusted and long-standing local relationships embedded in the community, and heritage brand recognition to sell within our 74 market footprint – a major competitive advantage ✓~60% of subscribers are outside of our local media market footprint ✓ Employ ~350 dedicated professionals ✓ Proprietary, internally developed software and customer support platform 14 ✓Offices in Charlotte, NC and Phoenix, AZ $24M LTM 9/30/25 subscription profit (1) (27% of TSQ’s Adjusted EBITDA ex political) $76M LTM 9/30/25 net subscription revenue (18% of TSQ’s net revenue ex. political) Product Suite Social Media Management Website Design and Hosting Online Reputation Monitoring Cloud-Based CRM E-Commerce Search Engine Optimization Appointment Scheduling Payment and Invoicing Customer Management Email and SMS Marketing Key Stats
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TOWNSQUARE INTERACTIVE’S ADDRESSABLE MARKET Source: D&B Hoovers. 15 Businesses nationwide Exclude largest 50 metro areas Include only companies with 20 or fewer employees Include only companies with $5M of revenue or less Exclude Auto dealers, Realtors, Banks Include only private, independently owned establishments 28,283,495 11,571,443 10,633,051 9,788,501 9,480,816 8,832,356 Target TSI Customers # of Viable Client Prospects 8.8M Target TSI Customers ~$300 Per Month Target ARPU ~$32B Total Addressable Market
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16 TOWNSQUARE INTERACTIVE: HELPING OUR CLIENTS SUCCEED https://townsquareinteractive.com/testimonials/ My experience has been nothing but wonderful. The traffic that has flown through the website because of its presence, its professionalism, has taken me to a next level… Some of my biggest contracts have come directly through the website. The fact that someone can put in roofer in Otego, NY and our name‘s pulled up first – it means a great deal Townsquare has been integral to the growth of our business. I would estimate it at 9% of our new clients were referred to us simply from the website.
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BROADCAST ADVERTISING: THE POWER OF LOCAL RADIO BRANDS, PERSONALITIES, AND SALES TEAMS A SAMPLING OF LOCAL MEDIA BRANDS Our local broadcast brands power our portfolio of local websites and apps, and their corresponding social and video platforms. It is a robust multiplatform content ecosystem with each component adding strength to each other. A significant competitive advantage in markets outside the Top 50 cities in the U.S. On-air talent = the Original Social Influencers • Drive deep, multiplatform audience engagement and create compelling advertising and marketing solutions for local clients across broadcast and digital platforms • Command incredible authority, trust and engagement with their followers, readers, listeners, and with our entire local communities Large, trusted, local salesforce with direct relationships with local advertisers and businesses AM/FM terrestrial broadcast alone reaches 50% of adults in our markets; with digital, over 70% reach Stable listening trends and audience given “Local First” strategy (local DJs and local content) Mature, “cash cow” business with very strong cash flow characteristics 341 radio stations 11M listeners (2) ______________________________________________________________ 1. Including political, LTM 9/30/25 Broadcast Net Revenue, Segment Profit and profit margin were $193M, $57M, and 29%. 2. Represents the average of Townsquare’s Spring 2025 and Fall 20 24 nationwide cume, P12+ M -Su 6a -6a, per Act 1 Systems (based on Nielsen data). 3. Cume data represents nationwide cume, P12+ M -Su 6a-6a, per Act 1 Systems (based on Nielsen data). TSL data represents nationwide TSL, P12+ M -Su 6a-12m, based on Nielsen’s Nationwide Regional Database. 17 50% Reach of Adults in Our Markets Just via AM/FM Listening (over 70% reach with digital audience) $185M LTM 9/30/25 Ex-Political Net Revenue(1) $50M LTM 9/30/25 Ex-Political Segment Profit (27% profit margin)(1) Key Stats Stable Listening Trends (3) 11M 11M 11M 11M 11M 0:00 2:24 4:48 7:12 9:36 12:00 14:24 M 5M 10M 15M 20M Spring 2023 Fall 2023 Spring 2024 Fall 2024 Spring 2025 Cume TSL
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MONTHLY UNIQUE VISITORS 474,371 1,160 INSTAGRAM FOLLOWERS 3,039,621 MONTHLY PAGE VIEWS 78,254 APP DOWNLOADS TOTAL LISTENING HOURS 74,598 26,257 NEWSLETTER SUBSCRIBERS 7,250 YOUTUBE SUBSCRIBERS TWITTER FOLLOWERS 2,599 FACEBOOK FANS 46,043 OMNICHANNEL BRAND STRATEGY POPULATION OF POUGHKEEPSIE ~900,000 # OF PEOPLE LISTENING TO WPDH ~150,000 18 _______________ Statistics as of September 2025, except for Monthly Page Views and Monthly Unique Visitors (represents average monthly page v iews and unique visitors in the nine months ended September 30, 2025).
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($ in millions) 1. Adjusted EBITDA is a non-GAAP financial measure. Please refer to page 2 for the definition of Adjusted EBITDA. 2. Unlevered Free Cash Flow is defined as Adjusted EBITDA less Capital Expenditures. % Conversion is defined as Adjusted EBITDA less Capital Expenditures divided by Adjusted EBITDA. SOLID FINANCIAL PERFORMANCE WITH HEALTHY MARGINS 5% 4% 81% 76% 24% 17% 19 3% 88% 25% + 5% -14% 12% $431 $371 $418 2019 2020 2021 2022 $102 $62 $105 2019 2020 2021 2022 $20 $15 $12 2019 2020 2021 2022 $83 $47 $93 2019 2020 2021 2022 Net Revenue (YoY Growth %) Adjusted EBITDA (% Margin) (1) Capital Expenditures (% of Total Revenue) Unlevered Free Cash Flow (% Conversion)(2) 11% $463 2023 3% $16 2023 25% $114 2023 86% $98 2023 -2% $454 3% $15 22% $100 85% $85 2024 2024 $451 4% $17 -1% 2024 22% $100 2024 83% $83 LTM 9/30/25 LTM 9/30/25 $439 4% $15 -2% LTM 9/30/25 22% $98 LTM 9/30/25 84% $82
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WHAT WE DID… OUR STRATEGY DELIVERED FINANCIAL RESULTS, EVEN IN A CHALLENGING ENVIRONMENT Q3 2025: WHAT WE SAID… AND WHAT WE DELIVERED 20 Net Revenue $106.5M - $108.5M $22.0MAdjusted EBITDA $22M -$23M $106.8M WHAT WE SAID…Q3 2025 Statistic
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Q3 and YTD 2025 HIGHLIGHTS 21 ✓Net Revenue and Adjusted EBITDA met guidance ✓Q3 2025 Net Revenue of $107M -7% vs. prior year (-4.5% excluding political) ✓Q3 2025 Adjusted EBITDA of $22M -14% vs. prior year (-2.0% excluding political) ✓September YTD 2025 Digital Revenue and Digital Segment Profit each ~55% of total ✓September YTD 2025 Digital Revenue +2.1% vs. prior year ✓Digital Advertising revenue growth +2.6% vs. prior year ✓Townsquare Interactive revenue growth +1.1% vs. prior year ✓September YTD 2025 Digital Segment Profit +3.6% vs. prior year ✓Digital Segment Profit Margin 26% Note: Please refer to page 2 for definitions of non -GAAP measures. Represent year-over-year (2025 vs. 2024) growth rates unless otherwise specified. ✓Generated $18 million of Cash Flow from Operations YTD 2025 ✓Refinanced debt in February 2025 by entering into a new $490 million Credit Agreement due February 2030 ✓Net leverage of 4.71x as of September 30th ✓Repaid $17 million of debt since the refinancing, including $12 million of term loan (including $6M repurchased at a discount in Q3 2025) ✓Announced $0.20 per share payable on February 2, 2026 to shareholders of record as of January 26, 2026 ✓Represents ~13% dividend yield as of November 7, 2025
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2025 GUIDANCE 22Note: Please refer to page 2 for definitions of non -GAAP measures. Q4 2024 Q4 2025 Guide $117.8 $105 - $109 -11% to -7% -6% to -2% Ex. political Q4 2024 Q4 2025 Guide $31.2 $21.5 - $23.5 -31% to -25% -17% to -9% Ex. political 2024 2025 Guide $451 $426 - $430 -6% to -5% -3% to -2% Ex. political 2024 2025 Guide $100 $88 - $90 -12% to -10% -3% to -1% Ex. political Net Revenue ($M) Net Revenue ($M) Adjusted EBITDA ($M) Adjusted EBITDA ($M) Q4 2025 Guidance FY 2025 Guidance
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BALANCE SHEET & OWNERSHIP $ in millions Maturity Pricing Cash $3 Revolver ($20M capacity) 5 Feb-30 S+375bps Term Loan 458 Feb-30 S+500bps Total Debt $463 Total Net Debt $460 Total Leverage(1) 4.74x Net Leverage (1) 4.71x Note: Please refer to page 2 for definitions of non-GAAP measures. 1. Adjusted EBITDA for the twelve months ended September 30, 2025 was $97.8 million. 2. Class B (high vote) and Class C (no vote) shares revert to Class A (1 vote) shares upon a sale. • $3M cash balance at 9/30/25 • On February 19, 2025, entered new $490M Credit Agreement (including $470M Term Loan at S+500bps, and $20M Revolving Credit Facility at S+375bps) • Repaid $17M of debt since refinancing ($12M Term Loan, $5M Revolver) 23 • On March 9, 2021, TSQ used $80M of cash to repurchase 100% of Oaktree Capital’s majority ownership stake in TSQ • On June 16, 2023, TSQ used $15M of cash to repurchase ~50% of MSG’s ownership stake in TSQ • On April 1, 2024, TSQ used $15M of cash to repurchase ~90% of MSG’s remaining ownership stake in TSQ Others 79% Management 13% MSD Capital 7% 5.12x 4.65x 7.45x 4.75x YE 2018 YE 2019 YE 2020 YE 2021 Balance Sheet Net Leverage Remains <5x Ownership (as of 11/5/25)(2) 4.29x YE 2022 4.43x YE 2023 4.33x YE 2024 (shares in millions) # of Votes Primary Holders Class A Common Stock 15.1 1 Public & MSD Class B Common Stock 0.8 10 Management Class C Common Stock 0.5 0 MSD Total Shares 16.5 4.71x 9/30/25
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24 APPENDIX: KEY INVESTOR HIGHLIGHTS
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KEY INVESTOR HIGHLIGHTS 2 3 Leading Management TeamVI 25 Attractive Free Cash Flow Profile with Significant Subscription Component Supporting Shareholder ReturnI Success in Digital Businesses Diversifying Revenue Base and Driving Revenue and Profit GrowthII Attractive Radio Industry DynamicsIII Leading Position in Small and Mid-Sized MarketsIV “Best in Class” Product & Engineering TeamV
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ATTRACTIVE FREE CASH FLOW PROFILE • Fast growing, profitable digital revenue is complemented by mature broadcast revenue base with attractive margins (digital ~55% of September YTD 2025 net revenue) • Strong contribution from subscription-based Townsquare Interactive segment (TSI) = $76M LTM 9/30/25 revenue; 18% of total net revenue (excluding political) = 32% LTM 9/30/25 Segment Profit margin; 27% of total Adjusted EBITDA (Excluding Political) • Diverse segments and operating scale contribute to greater net revenue and Adjusted EBITDA growth • Low, predictable capex requirements (<5% of revenue) • Substantial tax shields related to the tax amortization of intangible assets • Announced initiation of a dividend in 2023, a +5% raise in 2024, and a +1% raise in 2025 ($0.20 quarterly dividend per share, $0.80 on an annualized basis), implied dividend yield of ~13% (2) delivering current cash returns to shareholders 26 I Unlevered Free Cash Flow Conversion (1) 2019 2020 2021 2022 81% 76% 88% 86% 2023 85% 2024 83% LTM 9/30/25 84% $ Unlevered FCF $82.7 $47.2 $92.7 $97.9 $85.0 $82.9 $82.3 Note: Please refer to page 2 for definitions of non-GAAP measures. 1. Unlevered Free Cash Flow defined as Adjusted EBITDA less Capex, and Unlevered Free Cash Flow Conversion defined as (Adjusted EBITDA – Capex) / Adjusted EBITDA. Unlevered Free Cash Flow, Unlevered Free Cash Flow Conversion, and Adjusted EBITDA are non-GAAP financial measures. Please refer to page 2 for the definition of Adjusted EBITDA and the appendix of this presentation for a reconciliation of Adjusted EBITDA to Net (loss) Income, the most directly comparable GAAP measure. 2. Based on TSQ share price as of 11/7/25.
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1. Represents Segment Profit Margin for the twelve months ended September 30, 2025. 2. Represents year-over-year revenue growth trends. 3. Represents average monthly global unique visitors (“UVs “) on our owned and operated websites in the nine months ended Septem ber 30, 2025 per Google Analytics. 4. Represents September YTD 2025 digital revenue for TSQ. Industry Average represents YTD June 2025 digital revenue for iHeart and Beasley, YTD Sep 2025 for Cumulus, and 1H 2024 for Audacy. Townsquare’s Digital Evolution Key Stats TSQ’s Digital Revenue ($M) and Growth Trends(2) Townsquare Interactive Sep YTD 2025 Revenue2018 Revenue Percentage of Revenue from Digital Sales (4) ✓ Programmatic Digital Advertising Platform ✓ In-house buying platform (DSP) integrated with 15+ buying platforms and all major advertising exchanges accessing >250 billion impressions/day ✓ In-House Digital Agency managing creative to campaign insights and everything in between to deliver strong Digital Advertising ROI ✓ Owned & Operated Platform ✓ Owned and operated network of digital brands, made up of over 400 websites and 380 mobile apps ✓ ~45 million unique visitors (3) ✓ Total Addressable Market: 8.8M U.S. SMBs and >$32B ✓ ~32% Segment Profit margin(1) ✓ Approximately 60% of TSQ subscribers are outside of TSQ’s local media market footprint Townsquare’s Digital Advertising Key Stats SUCCESS IN SUBSCRIPTION DIGITAL MARKETING AND DIGITAL ADVERTISING SOLUTIONS HAS DRIVEN THE COMPANY’S DIGITAL TRANSFORMATION Digital businesses support long-term growth and revenue and profit diversification, including subscription-based profit Digital 30% Digital 55% 27 +5%+13% +24% +28% +19% $88 $100 $124 $159 $167 $199 2016 2017 2018 2019 2020 2021 2022 $231 2023 $232 $234 2024 +16% +1% +1% (Industry Average) 55% 26% Townsquare Radio Broadcasters II 2011 2016 Sep YTD 2025 1M 37M 45M *Average Monthly Unique Visitors on TSQ’s Owned and Operated Websites >40x Audience Growth Since 2011
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RADIO: A STABLE FOUNDATION WITH AN ATTRACTIVE VALUE PROPOSITION 1. Nielsen Audio RADAR reports (139, 143, 147, 151, 155, 159, 163), Mon-Sun, 12M-12M. 2. Edison Research, “Share of Ear,” Q4 2024. Persons 18+. 3. Nielsen Audience Insights Q4 2023. Persons 18+. • Radio megaphone with proven ability to activate audience to action • Large, local salesforce with direct relationships with local advertisers • Compelling live and local content on heritage brands delivered by local personalities • First party audience data collection and insights • Ability to produce curated local content absent from national and social media platforms • Radio is still one of the most cost-effective and efficient ways for local advertisers to reach the masses and local communities • Attribution tools, such as Townsquare Analytics, provide ways to measure broadcast campaigns that have historically not existed • Unlike certain other traditional media, radio’s audience is stable • The introduction of streaming, mobile apps and smart speakers have added to radio’s total audience • Radio reaches >80% of Americans 18+ (1) • Radio dominates ad-supported audio, with 67% vs. podcasts’ 18%, ad- supported streaming audio services 12%, and ad-supported satellite radio’s 3% (2) • Radio boasts highest weekly reach among traditional media Radio’s Weekly Reach (P12+) (1) 28 Smartphone TV (Live + Time-Shifted) Radio TV-Connected Devices Computer 83% 82% 75% 62% 74% Weekly Reach (P18+) (3) 41%Tablet III 2019 2020 2021 248M 238M 235M 235M 2022 Radio Reaches Everyone Radio’s Audience is Stable Radio Delivers a Local Connection Radio Delivers Results at an Attractive Price 2023 232M 227M 2024
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Townsquare operates in 74 small and mid-sized markets across the US, with virtually no presence in the top 50 markets ✓ More attractive competitive landscape – Limited focus from larger media players – Starved for high quality media and entertainment experiences – Limited competition from advertising technology and digital marketing solutions providers ✓ Healthy, stable markets with lower economic volatility and stabilizing institutions such as universities, military installations and state capitals TSQ reaches a majority of the population in its markets ✓ TSQ has trusted relationships between its heritage brands and its audience and strong local relationships with its advertisers ✓ TSQ’s ability to bring national products, technology and practices to small and mid-sized markets is unique ─ Our national scale and expertise allows us to develop market leading products and services, and provide training and support to our local markets ✓ On average, lower level of unemployment versus the national average (Count of Townsquare Markets by DMA Rank) Average Townsquare market population: ~300k (50K – 1M) 1. Source: Nielsen, Fall 2021. 2. Bureau of Labor Statistics; TSQ averages based on simple average of local market MSA unemployment rate. SMALL AND MID-SIZED MARKET STRATEGY IS A COMPETITIVE ADVANTAGE ✓ Inside Sales Team in Charlotte focused on serving cities with under 1.5 million people 29 31 No Presence 7 8 15 12 1 0-50 51-99 100-149 150-199 200-249 250+ Unranked IV Opportunity in Small and Mid-Sized Markets(1) Unemployment Rate(2) 2016 2017 2018 2019 2020 2021 4.6% 4.9% 4.2%4.4% 3.8% 3.9% 3.6%3.7% 7.4% 8.1% 5.0%5.3% 2022 3.6%3.6% 2023 3.6%3.6% June 2024 4.0%4.3%
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“BEST IN CLASS” PRODUCT AND ENGINEERING TEAM 30 Complete end-to-end product, design and engineering team ‒ 50+ person team organized around Design, Engineering and Q&A disciplines ‒ Winner of the NAB’s 2022 PILOT Technology Innovation Award for in- house built Customer Relationship Management (CRM) platform Collaborative, yet structured team focus allows for rapid innovation and stable environment at scale Annual hackathons and periodic meet -ups foster teamwork and accelerate innovation Developed countless products and tools for TSQ, including: ✓ Content Management System that supports 400+ TSQ websites, ~20,000 articles per month, SMB websites (TSI) and is used daily by 1,000+ employees ✓ Mobile app platform for 380 brand/station apps and an aggregator app ( radioPup) ✓ Premium digital advertising products ✓ Sales tools including the Blueprint app and CRM V
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EXPERIENCED MANAGEMENT TEAM ▪ President of AOL Media ▪ SVP,Worldwide Marketing at Bertelsmann Music Group ▪ 10+ years at Townsquare ▪ Owner and Managing Principal of AMG Financial ▪ EVP and CFO of LiveWire Ventures ▪ EVP and CFO of PriCellular Corporation (sold in 1998 for $1.4bn) ▪ 10+ years at Townsquare ▪ Associate at Bear Stearns and Brown Brothers Harriman ▪ Analyst at JP Morgan ▪ 10+ years at Townsquare ▪ President of GAP West ▪ Leadership roles at Bonneville Communications, Clear Channel and Katz Radio ▪ 10+ years at Townsquare ▪ Vice President, Design and Product at AOL Media ▪ 10+ years at Townsquare ▪ Director of Revenue Management at Clear Channel ▪ 10+ years at Townsquare ▪ Associate at Oak Hill Capital Partners ▪ Analyst at Merrill Lynch ▪ 10+ years at Townsquare ▪ Talent Acquisition Partner at Yodle ▪ 10+ years at Townsquare 31 Bill Wilson Chief Executive Officer (In current role since 2017) Stu Rosenstein EVP, Chief Financial Officer (In current role since 2010) Claire Yenicay EVP , Investor Relations (In current role since 2015) Erik Hellum EVP, COO Local Media (In current role since 2017) Sun Sachs SVP , Product & Engineering (In current role since 2010) Cristina Cipolla SVP , Data & Analytics (In current role since 2013) Scott Schatz EVP, Finance & Operations (In current role since 2015) Heather Hagar SVP , Human Resources (In current role since 2021) ) VI
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32 APPENDIX: NON-GAAP RECONCILIATIONS
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Segment Reporting: Q3 and September YTD Results ($ in 000s) 33Note: Segment Profit is defined as revenue less direct operating expenses, excluding depreciation, amortization, and stock-based compensation.
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Q3 Segment Reporting: Calculation of Segment Profit ($ in 000s) 34
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September YTD Segment Reporting: Calculation of Segment Profit ($ in 000s) 35
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Q3 and September YTD Reconciliation of Net Income To Adjusted EBITDA and Adjusted EBITDA (Excluding Political) ($ in 000s) 36 (a) Other includes net (gain) loss on sales and retirements of assets and other expense (income), net. Note: Adjusted EBITDA and Adjusted EBITDA (Excluding Political) is a non-GAAP financial measure. Please refer to page 2 for a definition of this measure.
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LTM September 30, 2025 Reconciliation of Net Income To Adjusted EBITDA ($ in 000s) 37 (a) Other includes net (gain) loss on sales and retirements of assets and other (income) expense, net. Note: Adjusted EBITDA is a non-GAAP financial measure. Please refer to page 2 for a definition of this measure.
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FY 2018-2024 Reconciliation of Net Income (Loss) to Adjusted EBITDA ($ in millions) Note: Adjusted EBITDA is a non-GAAP financial measure. Please refer to page 2 for a definition of this measure. 1. In 2019 and 2020, TSQ took significant non-cash impairment charges to the value of its FCC licenses, primarily due to a change in valuation methodology adopted after discussion with its new auditors. Beginning with the 2019 audit, TSQ no longer utilizes the revenue and cash flows from Townsquare Ignite, Townsquare Interactive and Live Events to support the intangible assets and goodwill that is associated with the radio stations, which is significantly different than how the Company valued TSQ’s intangible assets and goodwill since the inception of TSQ in 2010. In 2023, TSQ took significant non-cash impairment charges to the value of its FCC licenses due to rising interest rates, decreases in third party broadcast revenue forecasts, and higher initial capital costs due to rising prices. As a reminder, impairment charges are purely non-cash charges and do not impact TSQ’s net revenue, direct operating expenses, Adjusted EBITDA or cash balance. 2. Includes impairment loss on investment, net loss from discontinued operations, net loss (gain) on sale and retirement of assets and other (income) expense 38 Year Ended December 31, Ending March 31, $ in millions 2018 2019 2020 2021 2022 2023 2024 Net (loss) income ($97.3) ($65.7) ($80.6) $18.8 $14.4 ($43.0) ($10.9) Provision (benefit) for income taxes 30.8 (14.6) (23.9) 10.4 (0.6) (6.1) 1.3 Interest expense, net 34.3 33.9 31.4 39.8 39.8 37.2 36.2 Gain (loss) on repurchase of debt (0.1) 0.0 (1.2) 0.0 (0.1) (1.2) 0.0 Loss on extinguishment and modification of debt 0.0 0.0 0.0 6.0 0.0 0.0 0.0 Depreciation and amortization 19.6 25.8 20.1 19.1 19.0 19.2 19.7 Stock-based compensation 1.6 2.6 2.1 3.7 3.8 8.0 17.2 Transaction and business realignment costs 2.9 1.7 5.7 5.3 4.4 1.2 4.9 Impairment of intangible assets, investments, goodwill and long-lived assets[1] 48.2 108.7 109.1 1.9 31.1 90.6 37.7 Other [2] 54.7 9.9 (0.7) 0.1 1.8 (5.8) (5.7) Adjusted EBITDA $94.7 $102.4 $62.1 $105.1 $113.7 $100.0 $100.4
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Q3 and September YTD Reconciliation of Net Revenue to Net Revenue Excluding the Effects of Political Revenue ($ in 000s) 39