Slide 1: Investor Presentation
INVESTOR Investor PRESENTATION Presentation May 2026
Slide 2: Forward-Looking Statements and Non-GAAP Financial Measures
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.
Slide 3: Community-Focused Digital and Broadcast Media and Digital Marketing Solutions Company
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
Slide 4: An Introduction to Townsquare (NYSE: TSQ): Facts & Stats
AN INTRODUCTION TO TOWNSQUARE (NYSE: TSQ): FACTS & STATS KEY STATS ▪ 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. $23
Slide 5: Townsquare's Transformation
TOWNSQUARE’S TRANSFORMATION From 2010 → To Q1 2026 From local, ingrained teams in 13 local markets to 74 local markets From <1M UVs per Month to 25M UVs Per Month From No Social Platform to 46M Social Media Followers From No Video Platform to 4.9B YouTube Lifetime Views From 100% Broadcast Only Clie
Slide 6: Townsquare: A View From the Top
TOWNSQUARE: A VIEW FROM THE TOP DIGITAL BROADCAST $237M LTM 3/31/2026 Net Revenue $179M LTM 3/31/2026 Net Revenue (1) $60M LTM 3/31/2026 Segment Profit $45M LTM 3/31/2026 Segment Profit (1) 25% LTM 3/31/2026 Segment Profit Margin 26% LTM 3/31/2026 Segment Profit Margin (1) 56% / 56% LTM 3/31/2026 Ne
Slide 7: We Are a Digital First Local Media Company and Digital Is Our Growth Engine
WE ARE A DIGITAL FIRST LOCAL MEDIA COMPANY AND DIGITAL IS OUR GROWTH ENGINE • In Q1 2026, Digital contributed 59% of total net revenue and 63% of total Segment Profit • Strong digital margins (26% in 2025) are in-line with our broadcast radio, cash-cow business (also 26% in 2025) • First quarter adv
Slide 8: Only Local Media Company Solely Focused on Markets Outside the Top 50
TOWNSQUARE IS THE ONLY LOCAL MEDIA COMPANY SOLEY FOCUSED ON MARKETS OUTSIDE THE TOP 50 Leading Presence in 74 Small & Mid-Sized Markets More Attractive Competitive Landscape – Portfolio of 400+ local community websites, 380 mobile apps, and 340 radio − Very limited focus from larger media players, d
Slide 9: Being a Digital First Local Media Company Is the Right Position To Be In
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
Slide 10: Townsquare Digital Revenue vs Local Media Industry
TOWNSQUARE DIGITAL REVENUE VS LOCAL MEDIA INDUSTRY DIGITAL AS % OF TOTAL REVENUE 59% 56% 34% Average: 31% Average: 25% 24% 21% 19% Note: Q1 2026 Digital as % of Total Revenue per Company filings for Saga and Townsquare. FY 2025 for iHeart and Beasley. YTD September 2025 for Cumulus. For Lee Enterpri
Slide 11: Digital Advertising (Townsquare Ignite)
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 $164M LTM 3/31/2026 net revenue data management platf
Slide 12: Townsquare Interactive: Organically Built Subscription Digital Marketing Solutions
TOWNSQUARE INTERACTIVE: ORGANICALLY BUILT SUBSCRIPTION DIGITAL MARKETING SOLUTIONS 100% owned, subscription-based business that provides an all-in-one SAAS Key Stats solution that provides a suite of digital marketing services to underserved SMBs ✓ Employ ~300 dedicated professionals $73M LTM 3/31/2
Slide 13: Townsquare Interactive's Addressable Market
TOWNSQUARE INTERACTIVE’S ADDRESSABLE MARKET # of Viable Client Prospects 28,283,495 Businesses nationwide 11,571,443 Exclude largest 50 metro areas 10,633,051 Include only companies with 20 or fewer employees 9,788,501 Include only companies with $5M of revenue or less 9,480,816 Exclude Auto dealers
Slide 14: Townsquare Interactive: Helping Our Clients Succeed
TOWNSQUARE INTERACTIVE: HELPING OUR CLIENTS SUCCEED 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 t
Slide 15: Broadcast Advertising: The Power of Local Radio Brands, Personalities, and Sales Teams
BROADCAST ADVERTISING: THE POWER OF LOCAL RADIO Key Stats BRANDS, PERSONALITIES, AND SALES TEAMS $179M LTM 3/31/2026 Ex-Political Net Revenue(1) Our local broadcast brands power our portfolio of local websites and apps, and their corresponding social and video platforms. It is a robust multiplatform
Slide 16: Omnichannel Brand Strategy
1,778,465 OMNICHANNEL BRAND STRATEGY MONTHLY PAGE FACEBOOK VIEWS FANS 49,950 81,683 APP DOWNLOADS 1,622 INSTAGRAM FOLLOWERS MONTHLY UNIQUE VISITORS # OF PEOPLE LISTENING 274,680 TO WPDH ~150,000 TWITTER FOLLOWERS 2,611 TOTAL LISTENING HOURS 7,320 64,515 9,355 YOUTUBE POPULATION OF NEWSLETTER SUBSCRI
Slide 17: Solid Financial Performance With Healthy Margins, Even in a Challenging Year
SOLID FINANCIAL PERFORMANCE WITH HEALTHY MARGINS, EVEN IN A CHALLENGING YEAR ($ in millions) Net Revenue (YoY Growth %) Adjusted EBITDA (% Margin) (1) -14% 12% 11% -2% -1% -5% -5% 17% 25% 25% 22% 22% 21% 20% + $463 $454 $451 $105 $114 $418 $427 $425 $100 $100 $88 $86 $371 $62 2020 2021 2022 2023 202
Slide 18: Our Strategy Delivered Financial Results, Even in a Challenging Environment
OUR STRATEGY DELIVERED FINANCIAL RESULTS, EVEN IN A CHALLENGING ENVIRONMENT Q1 2026: WHAT WE SAID… AND WHAT WE DELIVERED Q1 2026 Statistic WHAT WE SAID… WHAT WE DID… Net Revenue $96M - $98M $96.8M Adjusted EBITDA $16M -$17M $16.4M 18
Slide 19: Q1 2026 Highlights
Q1 2026 HIGHLIGHTS ✓Net Revenue and Adjusted EBITDA met guidance ✓Generated $4 million of Cash Flow from Operations in Q1 2026 ✓Q1 2026 Net Revenue of $97M -2% vs. prior year (with and without ✓Net leverage of 5.27x as of March 31st political) ✓Announced $0.20 per share payable on August 3, 2026 to
Slide 20: 2026 Guidance
2026 GUIDANCE Q2 2026 Guidance FY 2026 Guidance Net Revenue ($M) Net Revenue ($M) $427 $420 - $440 $115.4 $114 - $116 -2% to +3% -1% to +0.5% -3% to +2% -2% to -0.5% Ex. political Ex. political Q2 2025 Q2 2026 2025 2026 Guide Guide Adjusted EBITDA ($M) Adjusted EBITDA ($M) $88 $87 - $93 $26.4 $24 -
Slide 21: Balance Sheet & Ownership
BALANCE SHEET & OWNERSHIP Balance Sheet Ownership (as of 5/6/26) (2) • $2M cash balance at 3/31/26 # of (shares in millions) Votes Primary Holders • On February 19, 2025, entered $490M Credit Agreement (including $470M Term Class A Common Stock 16.6 1 Public & MSD Loan at S+500bps, and $20M Revolvin
Slide 22: Appendix: Key Investor Highlights
APPENDIX: KEY INVESTOR HIGHLIGHTS 22
Slide 23: Key Investor Highlights
KEY INVESTOR HIGHLIGHTS I Attractive Free Cash Flow Profile with Significant Subscription Component Supporting Shareholder Return 2 Success in Digital Businesses Diversifying Revenue Base and II Driving Revenue and Profit Growth 3 III Attractive Radio Industry Dynamics IV Leading Position in Small a
Slide 24: Attractive Free Cash Flow Profile
I ATTRACTIVE FREE CASH FLOW PROFILE • Fast growing, profitable digital revenue is complemented by mature broadcast revenue base with attractive margins (digital ~59% of Q1 2026 net revenue) • Strong contribution from subscription-based Townsquare Interactive segment (TSI) = $73M LTM 3/31/2026 revenu
Slide 25: Success in Subscription Digital Marketing and Digital Advertising Solutions
II 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 Townsquare Interactive Townsquare’s Digital Advertisi
Slide 26: Radio: A Stable Foundation With an Attractive Value Proposition
III RADIO: A STABLE FOUNDATION WITH AN ATTRACTIVE VALUE PROPOSITION Radio Reaches Everyone Radio’s Audience is Stable • Radio reaches >80% of Americans 18+ (1) • Unlike certain other traditional media, radio’s audience is stable • Radio dominates ad-supported audio, with 67% vs. podcasts’ 18%, ad- •
Slide 27: Small and Mid-Sized Market Strategy Is a Competitive Advantage
IV SMALL AND MID-SIZED MARKET STRATEGY IS A COMPETITIVE ADVANTAGE Townsquare operates in 74 small and mid-sized markets across Opportunity in Small and Mid-Sized Markets(1) the US, with virtually no presence in the top 50 markets (Count of Townsquare Markets by DMA Rank) Average Townsquare market po
Slide 28: "Best in Class" Product and Engineering Team
V “BEST IN CLASS” PRODUCT AND ENGINEERING TEAM 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) p
Slide 29: Experienced Management Team
VI EXPERIENCED MANAGEMENT TEAM Bill Wilson Stu Rosenstein Claire Yenicay Erik Hellum Chief Executive Officer EVP, Chief Financial Officer EVP, Investor Relations EVP, COO Local Media (In current role since 2017) (In current role since 2010) (In current role since 2015) (In current role since 2017) ▪
Slide 30: Appendix: Non-GAAP Reconciliations
APPENDIX: NON-GAAP RECONCILIATIONS 30
Slide 31: Segment Reporting: Q1 Results
Segment Reporting: Q1 Results ($ in 000s) Note: Segment Profit is defined as revenue less direct operating expenses, excluding depreciation, amortization, and stock-based compensation. 31
Slide 32: Q1 Segment Reporting: Calculation of Segment Profit
Q1 Segment Reporting: Calculation of Segment Profit ($ in 000s) 32
Slide 33: Q1 Reconciliation of Net Income To Adjusted EBITDA
Q1 Reconciliation of Net Income To Adjusted EBITDA and Adjusted EBITDA (Excluding Political) ($ in 000s) (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 meas
Slide 34: FY 2019-2025 Reconciliation of Net Income (Loss) to Adjusted EBITDA
FY 2019-2025 Reconciliation of Net Income (Loss) to Adjusted EBITDA ($ in millions) 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) ($9.8) Provision (benefit) for income taxes (14.6) (23.9) 10.4 (0.6) (6.1) 1.3 4.
Slide 35: Q1 Reconciliation of Net Revenue Excluding Political Revenue
Q1 Reconciliation of Net Revenue to Net Revenue Excluding the Effects of Political Revenue ($ in 000s) 35
Slide 36: Townsquare
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