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townsquare INVESTOR PRESENTATION August 2026
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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 August 6, 2026. 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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$425M / $85M LTM 6/30/2026 Net Revenue/ Adjusted EBITDA 22M / 11M Total Digital / Broadcast Audience(2) ~2x Digital Audience to Radio Audience AN INTRODUCTION TO TOWNSQUARE (NYSE: TSQ): FACTS & STATS KEY STATS 4 $240M / $61M LTM 6/30/2026 Digital Net Revenue / Digital Segment Profit 17% / 31% % of LTM 6/30/2026 Total Revenue and Adjusted EBITDA from Digital Subscription Solutions (Townsquare Interactive)(1) 57% / 59% 1H 2026 Net Revenue / Segment Profit from Digital Note: Please refer to page 2 for definitions of non -GAAP measures. 1. Excluding political revenue. 2. Total digital audience represents average monthly global UVs on Townsquare’s owned and operated websites in 1H 2026 per Google Analytics. Total broadcast audience represents the average of Townsquare’s Fall 2025 and Spring 2025 nationwide cume, P12+ M-Su 6a -6a, per Act 1 Systems (based on Nielsen data). 3. Townsquare’s Board of Directors approved a quarterly dividend payment of $0.20 per share, payable on November 2, 2026 to shareholders of record as of October 26, 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 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 ~2x the size of our terrestrial radio audience ▪ Approximately 17% of our total net revenue(1) is monthly, recurring subscription digital marketing revenue $0.20 / ~13% Quarterly Dividend Per Share(3) / ~13% Dividend Yield as of August 5, 2026
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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 55%+ Digital Revenue/Profit From <1M UVs per Month to 22M UVs Per Month From No Social Platform to 46M Social Media Followers From No Video Platform to 4.9B YouTube Lifetime Views From A Pure Radio Broadcast Company to a Digital First Local Media Company From 2010 → To Q2 2026 5 From No First-Party Data Platform to a Robust Platform with 16 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 $7M of Other (live events) revenue in the twelve mont hs ending June 30, 2026. 1. Excludes broadcast political revenue of $3M, and total political revenue of $3M. 2. See slide 14. TOWNSQUARE: A VIEW FROM THE TOP LTM 6/30/2026 Net Revenue (1) LTM 6/30/2026 Segment Profit Margin (1) 336 Local Radio Stations TOWNSQUARE IGNITE BROADCAST $175M $44M 25% 41%/42% LTM 6/30/2026 Net Revenue / Segment Profit Contribution (1) Reach 1 out of 2 Adults (50%) via our AM/FM in each local market 6 LTM 6/30/2026 Segment Profit (1) Subscription Digital Marketing Solutions $32B Total Addressable Market (2) Digital Advertising Owned & Operated Digital Brands Data Analytics & Management Platform Digital Programmatic Technology Platform “Cash Cow” Business TOWNSQUARE INTERACTIVE LTM 6/30/2026 Net Revenue LTM 6/30/2026 Segment Profit Margin $72M $25M 35% 17%/24% LTM 6/30/2026 Net Revenue / Segment Profit Contribution LTM 6/30/2026 Segment Profit LTM 6/30/2026 Net Revenue LTM 6/30/2026 Segment Profit Margin $168M $36M 21% 40%/34% LTM 6/30/2026 Net Revenue / Segment Profit Contribution LTM 6/30/2026 Segment Profit White-Labeling Technology to Third-Parties TOTAL DIGITAL LTM 6/30/2026 Net Revenue LTM 6/30/2026 Segment Profit Margin $240M $61M 25% 56%/57% LTM 6/30/2026 Net Revenue / Segment Profit Contribution LTM 6/30/2026 Segment Profit
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WE ARE A DIGITAL FIRST LOCAL MEDIA COMPANY AND DIGITAL IS OUR GROWTH ENGINE • In 1H 2026, Digital contributed 57% of total net revenue and 59% of total Segment Profit • Strong digital margins (25% in 1H 2026) are in -line with our broadcast radio, cash-cow business (also 25% in 1H 2026) • Townsquare Interactive, our subscription-based digital business, achieved all -time high Segment Profit margins in Q2 2026 (38%) Segment Net Revenue ($M) Segment Profit ($M) 7 Jun YoY % of Jun YoY % of YTD'26 Growth % Total YTD'26 Growth % Total Margin% Digital Advertising $86.5 9.1% 41% $18.4 (2.1%) 35% 21% Subscription Digital Marketing Solutions 34.7 (8.2%) 16% 12.4 (0.5%) 24% 36% Total Digital 121.2 3.5% 57% 30.8 (1.5%) 59% 25% Broadcast Advertising 85.2 (6.0%) 40% 21.4 (9.3%) 41% 25% Other (Live Events) 5.8 (10.0%) 3% (0.1) NM (0%) (2%) Total $212.1 (0.9%) 100% $52.0 (6.2%) 100% 25%
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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 SOLELY 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 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 336 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 15,000 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 2025, radio advertising was ~4% of all advertising dollars spent in the United States, while digital advertising solutions contributed ~74% • Radio is a mature and cash flow generative business – a quintessential “cash cow” business • It is estimated that digital advertising will grow to 81% of all advertising spend in 2030 • As a Digital First Local Media Company , TSQ’s growth engine has and will continue be digital Source: 2025 S&P Global Market Intelligence. 'Advertising Expenditure Forecasts,’ December 2025. Advertising expenditure and related data provided by Magna Global, 2025. 2025 2026 2027 2028 $306 $340 +11%+14% $370 +9% $402 +9% $431 +7% FORECASTED U.S. DIGITAL AD SPEND ($B) FORECASTED U.S. AD SPEND IN 2030 81% 11% 3%3%2% 0% Digital Television Radio Print Outdoor Cinema 9 $463 +7% 2029 2030
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Average: 25% Average: 31% TOWNSQUARE DIGITAL REVENUE VS LOCAL MEDIA INDUSTRY 37% 57% 19% 21% 25% 56% DIGITAL AS % OF TOTAL REVENUE 10 Note: June YTD 2026 Digital as % of Total Revenue per Company filings for Townsquare, Q1 2026 for Saga, Beasley, and iHeart. YTD September 2025 for Cumulus. For Lee Enterprises, represents the three months ending March 29, 2026.
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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 ▪ Bring national scale and sophistication to small markets, including high impact solutions that are not available on programmatic exchanges (such as site takeovers, first impression full site coverage, mobile interstitials, sponsored social mentions and endorsements) ▪ Includes sale of digital advertising on our local and national websites and mobile apps, and online radio streams ▪ Proprietary advertising technology platform, with in-house trading desk ▪ Integrated with 15+ digital advertising buying platforms ▪ Access to all major advertising exchanges and mobile apps ▪ 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 ▪ White-label our digital programmatic advertising services on a contracted basis to third- parties through our Media Partnership division 400+ Local Websites 10 National Websites Note: As of June 30, 2026 unless otherwise noted. 1. Represents % of 1H’26 Digital Advertising segment revenue. 2. Represents average monthly global unique visitors (“ UVs “) on our owned and operated websites in the six months ended June 30, 2026 per Google Analytics. 380 Mobile Apps 22M Monthly UVs (2) 46M Social Followers 4.9B 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 $36M LTM 6/30/2026 Segment Profit (~21% profit margin) $168M LTM 6/30/2026 net revenue (~39% of TSQ’s net revenue) OWNED & OPERATED PLATFORM (~30% OF REVENUE)(1) PROGRAMMATIC PLATFORM (~70% OF REVENUE)(1) DATA ANALYTICS & MANAGEMENT PLATFORM 16M USER PROFILES 11 2011 Jun YTD 2026 1M 22M *Average Monthly Unique Visitors on TSQ’s Owned and Operated Websites >20x Audience Growth Since 2011 ▪ Proprietary website / app platforms and in-house Content Management System (CMS)
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MEDIA PARTNERSHIPS: A SIGNIFICANT GROWTH OPPORTUNITY We currently have 16 Media Partners reaching 41 incremental markets, and expect to generate $12M of revenue in 2026 12 16 Media Partners $6M 2025 Revenue / >2x 2026F Growth 250+ AEs in Media Partner Markets 41 Incremental Markets to TSQ’s Footprint KEY STATS 2024 2025 2026F 2030F <$1M $6M $12M+ $50M ▪ Through our Media Partnership division (launched in early 2024), we white-label our digital programmatic advertising services on a contracted basis to third-parties ▪ These services include: ▪ We are now beginning to license our in-house, award-winning CRM (Blueprint), to interested partners as well (1 partner to date) ▪ Our goal is to become the chosen provider of digital programmatic advertising to broadcasters and digital agencies in local markets outside of major cities ✓ Creative Development ✓ Media Buying ✓ Optimization ✓ Customer Support ✓ Sales Training & Mentoring ✓ Campaign Strategy ~20% Profit Margin SELECT PARTNERS 2 Partners 5 Partners 16 Partners (to date) ✓ Omni Channel Reporting MEDIA PARTNERSHIPS REVENUE
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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 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 ~300 dedicated professionals ✓ Proprietary, internally developed software and customer support platform 13 ✓Offices in Charlotte, NC and Phoenix, AZ $25M LTM 6/30/2026 subscription profit (1) (31% of TSQ’s Adjusted EBITDA ex political) $72M LTM 6/30/2026 net subscription revenue (17% 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. 14 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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15 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 336 radio stations 11M listeners (2) ______________________________________________________________ 1. Including political, LTM 6/30/26 Broadcast Net Revenue, Segment Profit and profit margin were $178M, $46M, and 26%. 2. Represents the average of Townsquare’s Spring 2025 and Fall 20 25 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. 16 50% Reach of Adults in Our Markets Just via AM/FM Listening (over 70% reach with digital audience) $175M LTM 6/30/2026 Ex-Political Net Revenue(1) $44M LTM 6/30/2026 Ex-Political Segment Profit (25% profit margin)(1) Key Stats Stable Listening Trends (3) 11M 11M 11M 11M 11M 0:00 2:24 4:48 7:12 9:36 12:00 14:24 M 5M 10M 15M 20M Fall 2023 Spring 2024 Fall 2024 Spring 2025 Fall 2025 Cume TSL
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MONTHLY UNIQUE VISITORS 265,856 1,770 INSTAGRAM FOLLOWERS 1,773,417 MONTHLY PAGE VIEWS 83,626 APP DOWNLOADS TOTAL LISTENING HOURS 77,195 8,481 NEWSLETTER SUBSCRIBERS 7,390 YOUTUBE SUBSCRIBERS TWITTER FOLLOWERS 2,618 FACEBOOK FANS 51,295 OMNICHANNEL BRAND STRATEGY POPULATION OF POUGHKEEPSIE ~900,000 # OF PEOPLE LISTENING TO WPDH ~150,000 17 _______________ Statistics as of June 2026, except for Monthly Page Views and Monthly Unique Visitors (represents average monthly page views and unique visitors in the six months ended June 30, 2026).
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($ 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, EVEN IN A CHALLENGING YEAR 4% 76% 17% 18 3% 88% 25% + -14% 12% $371 $418 2020 2021 2022 $62 $105 2020 2021 2022 $15 $12 2020 2021 2022 $47 $93 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 2025 2025 $427 4% $15 -5% 2025 21% $88 2025 83% $73 LTM 6/30/26 $425 -5% LTM 6/30/26 20% $85 LTM 6/30/26 3% $14 LTM 6/30/26 83% $71
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WHAT WE DID… OUR STRATEGY DELIVERED FINANCIAL RESULTS, EVEN IN A CHALLENGING ENVIRONMENT Q2 2026: WHAT WE SAID… AND WHAT WE DELIVERED 19 Net Revenue $114M - $116M $24.8MAdjusted EBITDA $24M -$25M $115.4M WHAT WE SAID…Q2 2026 Statistic
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Q2 and 1H 2026 HIGHLIGHTS 20 ✓Net Revenue and Adjusted EBITDA met guidance ✓Q2 2026 Net Revenue of $115M approximately flat to prior year ✓Q2 2026 Adjusted EBITDA of $25M -6% vs. prior year ✓June YTD 2026 Digital Revenue ~57% of total and Digital Segment Profit ~59% of total ✓Total Q2 2026 Digital Revenue +5% vs. prior year ✓Driven by Digital Advertising revenue growth +11.0% vs. prior year, offsetting Townsquare Interactive revenue decline of -8.5% vs. prior year ✓Total Q2 2026 Digital Segment Profit +1% vs. prior year ✓Total Digital Segment Profit Margin 27% ✓TSI Segment Margin of 38% (all-time high) Note: Please refer to page 2 for definitions of non -GAAP measures. Represent year-over-year (2026 vs. 2025) growth rates unless otherwise specified. ✓Generated $8 million of Cash Flow from Operations in 1H 2026 ✓Net leverage of 5.44x as of June 30th ✓Announced $0.20 per share payable on November 2, 2026 to shareholders of record as of October 26, 2026 ✓Represents ~13% dividend yield as of August 5, 2026
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2026 GUIDANCE 21Note: Please refer to page 2 for definitions of non -GAAP measures. Q3 2025 Q3 2026 Guide $106.8 $108 - $110 +1% to +3% -0.5% to +1% Ex. political Q3 2025 Q3 2026 Guide $22.0 $22.5 - $23.5 +2% to +7% 2025 2026 Guide $427 $425 - $431 -1% to +1% -2% to -0.5% Ex. political 2025 2026 Guide $88 $87 - $90 -1% to +2% Net Revenue ($M) Net Revenue ($M) Adjusted EBITDA ($M) Adjusted EBITDA ($M) Q3 2026 Guidance FY 2026 Guidance
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BALANCE SHEET & OWNERSHIP $ in millions Maturity Pricing Cash $1 Revolver ($20M capacity) 12 Feb-30 S+375bps Term Loan 450 Feb-30 S+500bps Total Debt(1) $462 Total Net Debt $461 Total Leverage(2) 5.46x Net Leverage (2) 5.44x Note: Please refer to page 2 for definitions of non-GAAP measures. 1. Total debt also includes $0.7M of vendor financing obligation. 2. Adjusted EBITDA for the twelve months ended June 30, 2026 was $84.7 million. 3. Class B (high vote) and Class C (no vote) shares revert to Class A (1 vote) shares upon a sale. • On February 19, 2025, entered $490M Credit Agreement (including $470M Term Loan at S+500bps, and $20M Revolving Credit Facility at S+375bps) 22 Significant historical share buyback activity: • 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 77% Management & Board 17% MSD Capital 7% 4.65x 7.45x 4.75x YE 2019 YE 2020 YE 2021 Balance Sheet Net Leverage Ownership (as of 8/3/26) (3) 4.29x YE 2022 4.43x YE 2023 4.33x YE 2024 (shares in millions) # of Votes Primary Holders Class A Common Stock 16.9 1 Public & MSD Class B Common Stock 0.8 10 Management Class C Common Stock 0.5 0 MSD Total Shares 18.2 5.14x YE 2025 5.44x 6/30/26
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23 APPENDIX: KEY INVESTOR HIGHLIGHTS
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KEY INVESTOR HIGHLIGHTS 2 3 Leading Management TeamVI 24 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 ~57% of 1H 2026 net revenue) • Strong contribution from subscription-based Townsquare Interactive segment (TSI) = $72M LTM 6/30/2026 revenue; 17% of total net revenue (excluding political) = 35% LTM 6/30/2026 Segment Profit margin; 31% 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 • Quarterly dividend of $0.20 per share, $0.80 on an annualized basis, with implied dividend yield of ~13% (2) delivering current cash returns to shareholders 25 I Unlevered Free Cash Flow Conversion (1) 2020 2021 2022 76% 88% 86% 2023 85% 2024 83% 2025 83% $ Unlevered FCF $47.2 $92.7 $97.9 $85.0 $82.9 $72.9 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 8/5/26. LTM 6/30/26 83% $70.7
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1. Represents Segment Profit Margin for the twelve months ended June 30, 2026. 2. Represents average monthly global unique visitors (“UVs “) on our owned and operated websites in the six months ended June 30 , 2026 per Google Analytics. 3. Represents 1H 2026 digital revenue for TSQ. Industry Average represents YTD Sep 2025 for Cumulus and Q1 2026 for iHeart, Bea sley and Saga. Townsquare’s Digital Evolution Key Stats TSQ’s Digital Revenue ($M) and Growth Trends Townsquare Interactive 1H 2026 Revenue2018 Revenue Percentage of Revenue from Digital Sales (3) ✓ Programmatic Digital Advertising Platform ✓ In-house trading desk 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 ✓ White-label our digital programmatic advertising services and other tech on a contracted basis to third-parties through our Media Partnership division ✓ Owned & Operated Platform ✓ Owned and operated network of digital brands, made up of over 400 websites and 380 mobile apps, and online radio ✓ 22 million unique visitors (2) ✓ Total Addressable Market: 8.8M U.S. SMBs and >$32B ✓ ~35% 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 57% 26 +18% 5-Year CAGR $73 $167 2015 2020 $236 2025 (Industry Average) 57% 25% Townsquare Radio Broadcasters II 2011 Q1 2026 1M 22M *Average Monthly Unique Visitors on TSQ’s Owned and Operated Websites >20x Audience Growth Since 2011 +7% 5-Year CAGR
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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) 27 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 28 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 29 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, ~15,000 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 $1.4bn) ▪ 10+ years at Townsquare ▪ Associate at Bear Stearns and Brown Brothers Harriman ▪ Analyst at JP Morgan ▪ 10+ years at Townsquare ▪ President of GAP West ▪ Leadership roles at Bonneville Communications, Clear Channel and Katz Radio ▪ 10+ years at Townsquare ▪ Vice President, Design and Product at AOL Media ▪ 10+ years at Townsquare ▪ Director of Revenue Management at Clear Channel ▪ 10+ years at Townsquare ▪ Associate at Oak Hill Capital Partners ▪ Analyst at Merrill Lynch ▪ 10+ years at Townsquare ▪ Talent Acquisition Partner at Yodle ▪ 10+ years at Townsquare 30 Bill Wilson Chief Executive Officer (In current role since 2017) Stu Rosenstein EVP, Chief Financial Officer (In current role since 2010) Claire Yenicay EVP , Investor Relations (In current role since 2015) Erik Hellum EVP, COO Local Media (In current role since 2017) Sun Sachs SVP , Product & Engineering (In current role since 2010) Cristina Cipolla SVP , Data & Analytics (In current role since 2013) Scott Schatz EVP, Finance & Operations (In current role since 2015) Heather Hagar SVP , Human Resources (In current role since 2021) ) VI
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31 APPENDIX: NON-GAAP RECONCILIATIONS
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Segment Reporting: Q2 and June YTD Results ($ in 000s) 32Note: Segment Profit is defined as revenue less direct operating expenses, excluding depreciation, amortization, and stock-based compensation.
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Q2 Segment Reporting: Calculation of Segment Profit ($ in 000s) 33
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June YTD Segment Reporting: Calculation of Segment Profit ($ in 000s) 34
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Q2 and June YTD Reconciliation of Net Income To Adjusted EBITDA and Adjusted EBITDA (Excluding Political) ($ in 000s) 35 (a) Other includes net loss (gain) on sales and retirements of assets and other expense (income), net. Note: Adjusted EBITDA and Adjusted EBITDA (Excluding Political) are non-GAAP financial measures. Please refer to page 2 for a definition of these measures.
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LTM June 30, 2026 Reconciliation of Net Income To Adjusted EBITDA ($ in 000s) 36 (a) Other includes net loss (gain) on sales and retirements of assets and other expense (income), 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 2019-2025 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 37 Year Ended December 31, $ in millions 2019 2020 2021 2022 2023 2024 2025 Net (loss) income ($65.7) ($80.6) $18.8 $14.4 ($43.0) ($10.9) ($9.8) Provision (benefit) for income taxes (14.6) (23.9) 10.4 (0.6) (6.1) 1.3 4.7 Interest expense, net 33.9 31.4 39.8 39.8 37.2 36.2 47.9 Gain (loss) on extinguishment, modification, repayments and repurchase of debt 0.0 (1.2) 6.0 (0.1) (1.2) 0.0 1.2 Depreciation and amortization 25.8 20.1 19.1 19.0 19.2 19.7 18.4 Stock-based compensation 2.6 2.1 3.7 3.8 8.0 17.2 13.8 Transaction and business realignment costs 1.7 5.7 5.3 4.4 1.2 4.9 11.7 Impairment of intangible assets, investments, goodwill and long-lived assets[1] 108.7 109.1 1.9 31.1 90.6 37.7 8.9 Other [2] 9.9 (0.7) 0.1 1.8 (5.8) (5.7) (8.7) Adjusted EBITDA $102.4 $62.1 $105.1 $113.7 $100.0 $100.4 $88.1
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Q2 and June YTD Reconciliation of Net Revenue to Net Revenue Excluding the Effects of Political Revenue ($ in 000s) 38