August 2019 - Investis Digital...Well-positioned to leverage in-market teams, digital DNA, local salesforce and first-party data insights to lead growth within its markets Significant

Investor Presentation August 2019

1 © Townsquare Media, Inc. 1

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.

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 filed on March 12, 2019, 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 “Equity 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 Operating Income, Adjusted EBITDA and Adjusted EBITDA Less Interest, Capex and Taxes. We define Adjusted Operating Income as operating income before the deduction of depreciation and amortization, stock-based compensation, corporate expenses, transaction costs, business realignment costs, impairment loss of goodwill and intangible assets, impairment loss on investment and net loss (gain) on sale and retirement of assets. Adjusted EBITDA is defined as net income (loss) before the deduction of income taxes, interest expense, net, repurchase of debt, transaction costs, depreciation and amortization, stock-based compensation, business realignment costs, impairment of goodwill and intangible assets, impairment loss on investment, net (income) loss from discontinued operations, net of income taxes, net (loss) gain on sale and retirement of assets, other expense (income) net, and gain (loss) on foreign exchange. Adjusted EBITDA Less Interest, Capex and Taxes is defined as Adjusted EBITDA less net cash interest expense, capital expenditures and cash paid for taxes. Adjusted Operating Income, Adjusted EBITDA and Adjusted EBITDA Less Interest, Capex and Taxes do not represent, and should not be considered as alternatives to, net (loss) income or cash flows from operations as determined under U.S. generally accepted accounting principles, or GAAP. For a reconciliation of these measures to net income, see Exhibit 99.1 to our Current Reports on Form 8-K filed with the SEC on August 6, 2019.


Introduction to Townsquare (NYSE: TSQ)

Owns and operates market-leading branded media

platforms: broadcast radio, digital, video, social, and

streaming

Brings national scale and expertise to 67 local markets

321

~12M 200

#1 or #2 radio position in 65 of 67 markets

radio listeners (1)

radio stations

Local live events per year

Townsquare Interactive

SMB customers (4)

Highly complementary media, marketing, and entertainment platforms Move customers and audience across platforms

Subscription-based revenue model

Organically built in 2012

Web and mobile sites

SEO, social media management

Reputation management and directory listings

Proprietary analytics and insights

~17M local website UVs (2)

Proprietary digital programmatic technology platform

Organically built in 2014

Precision customer targeting solutions

In-house Demand Supply Platform (DSP) and media buying and optimization

Townsquare Ignite

~17,300

300+ local websites /

local station apps

__________________________________________________ Note: UVs is defined as unique visitors. Branded Media and Digital Advertising Technology (Townsquare Ignite) make up our Advertising segment. 1. Represents the average of Townsquare’s Spring 2018 and Fall 2018 nationwide cume, P12+ M-Su 12a -12a, per Act 1 Systems (based on Nielsen data). 2. Represents average monthly global UVs on our local owned and operated websites in the six months ended June 30, 2019 per Google Analytics. 3. Average monthly campaigns in 1H 2019. 4. As of June 30, 2019.

We are the leading multi-platform branded media, digital marketing, and live events company focused primarily on small to mid-sized markets in America’s heartland

Diversified multi-channel growth strategy

Provides cutting edge digital marketing and advertising technology

solutions to a broad base of ~50,000 local and national advertisers

and SMBs

active campaigns per month (3) ~2,600

Annual recurring heritage events (e.g. WYRK’s Taste of Country is celebrating its 20th anniversary)

Focused on providing family friendly entertainment

Monetizes the audience relationship


Investment Highlights

#1 or #2 radio position in 65 of 67 markets

Stable cities with attractive fundamentals: lower economic volatility and competition

Reaches millions of people in the “Heartland” and connects this audience to local and national advertisers

Sales are generated through largely local and direct-to-client relationships

Local advertising spend is large (~$88 billion) and projected to grow at a ~8% CAGR (1)

Radio audience continues to grow, while digital is growing rapidly and taking share from traditional print-based mediums (e.g., newspaper and yellow pages)

Radio is the #1 reach medium in the U.S., reaching more than 90% of Adults 12+ each week (2)

Track record of successfully driving value through organic product development

Well-positioned to leverage in-market teams, digital DNA, local salesforce and first-party data insights to lead growth within its markets

Significant scale with diversified revenue streams built through successful organic initiatives and strategic M&A

Steady growth of ~5% 1H 2019 PF revenue and ~12% 1H 2019 PF Adjusted EBITDA (3)

Strong and stable cash flow, providing fuel for product development and innovation (24% LTM 6/30/19 PF Adjusted EBITDA margin (3))

Valuable tax benefits, including tax deductible amortization and net operating loss carryforwards

Deep local audience engagement through longstanding and powerful brands on the air, online and experiential

Demonstrable success leveraging traditional media core to build growth businesses through intimate understanding of audience and advertiser needs (e.g., live events, Townsquare Interactive, Townsquare Ignite etc.)

_____________________________________ 1. Source: SNL Kagan. 2018-2023 CAGR. 2. Nielsen Audio, RADAR Report 139, Mon-Sun, 12M-12M. 3. Pro forma for the acquisition of three radio stations in Princeton, New Jersey on July 2, 2018 as if it had occurred on January 1, 2018.

Market-leading position in small & mid-sized markets

Platform for growth and innovation

Strong financial profile

Diversified, multi-platform

products and audiences

Attractive industry dynamics reinforce growth

opportunity


Small and Mid-Sized Market Strategy is a Competitive Advantage

Townsquare 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

We reach a majority of the population in our markets

We have trusted relationships between our heritage brands and our audience and strong local relationships with our advertisers

Our 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

The Heartland is as much a mindset as it is a geographical definition, and many of our brands are significant influential institutions in this landscape that can help shape trends

“So many marketing programs are oriented toward metro elite imagery… Marketing needs to reflect less of New York and Los Angeles culture… and more of Des Moines and Scranton.”

— Wall Street Journal, November 21, 2016

Advertisers Seek Middle America Consumers

Townsquare operates in 67 small and mid-sized markets across the US, with virtually no presence in the top 50 markets

Average Townsquare market population ~300K (50K – 1M)


The Power of Our Brands and Talent

5

___________________________________________________ 1. Represents the average of Townsquare’s Spring 2018 and Fall 2018 nationwide cume, P12+ M-Su 12a -12a, per Act 1 Systems (based on Nielsen data). 2. Represents average monthly global UVs on our local owned and operated websites in the six months ended June 30, 2019 per Google Analytics. 3. Represents live and local morning shows that are ranked first in-format according to Nielsen’s A25-54 ratings.

Original content and influential local media personalities drive deep, multi-platform audience engagement and create compelling advertising and marketing solutions for clients

Strength in Country, News/Talk/Sports and Rock formats

Live and local personalities with strong ties to the community

Proprietary mobile radio app, radioPup, and individual station apps reach our audience on the go

We supplement our local content with national content from our portfolio of 9 music and entertainment focused websites, including Taste of Country, XXL, Loudwire, Ultimate Classic Rock, PopCrush, The Boot, The Boombox, Diffuser and ScreenCrush

Select Radio and Digital Media Brands

Townsquare owns and operates market leading media platforms: broadcast radio, digital, video, social and streaming

321 radio stations

330+ local, community websites

300+ local station apps

12M listeners (1)

17M UVs (2) per month

#1 or #2 share of radio revenue in 65 of 67 markets

77 top-rated live and local morning shows (3)

Key Stats


Townsquare Ignite (Programmatic Digital Advertising)

Townsquare Ignite is our proprietary advertising technology platform that enables us to fulfill our client’s entire audience demand, using:

TSQ digital inventory (on our owned and operated websites) AND

Third party advertising inventory across the Internet

Hyper-targeted online audiences are delivered across desktop, mobile, apps, connected TV, email, paid search, and social media platforms utilizing display, video and native executions

Clients paying for highly effective ads, delivered to the right people at the right time

Deliver far more precision and personalization of messaging and media, resulting in more efficiently targeted ad campaigns

____________________________ 1. For the six months ended June 30, 2019. 2. Represents management estimates.

Townsquare Ignite is an effective and efficient advertising solution that enhances our local market presence, brands and trusted relationships with sophisticated precision in-house audience targeting solutions

Targeting Methods

Advanced Audience

Contextual

Re-targeting

Video

Social

Geolocation

Hyper-local Mobile

Foot Attribution

Search

Native

In-house buying platform (DSP) integrated with 1,000+ exchanges accessing >250 billion impressions/day

~2,600 Ignite campaigns live each month (1)

Up ~72% from the prior year

2019 net revenue approaching $50M; $100M of revenue expected in 3-5 years (2)

Key Stats


11,750 13,650

17,300

Jun-17 Jun-18 Jun-19

Townsquare Interactive (TSI) (Digital Marketing Solutions)

TSI provides a wide array of digital services for a recurring monthly subscription fee, including:

Website design and management

Search engine optimization

Re-Targeting

Business listing

TSI targets SMBs in our 67 small and mid-sized markets leveraging our local sales teams, as well as small to mid-sized markets with demographics consistent with TSQ markets via our Inside Sales Team of over 100 sellers

Approximately half of our subscribers are outside of our local media market footprint

TSI is a leading provider of digital marketing solutions to SMBs

___________________________________________________ 1. As of June 30, 2019. 2. Represents management estimates.

~17,300 subscribers

~$300 average monthly subscriber fee

~$62M annual run-rate net revenue

$100M of revenue expected in 3-5 years (2)

Key Stats (1)

Social media marketing

Mobile optimization

E-commerce

Reputation monitoring

TSI Subscribers

+1,900 +3,650

Charlotte Business Journal’s “2018 Best

Places to Work” Winner

4 years in a row


Leading Research Firm, Borrell Associates, Singles out Townsquare as Top Digital Performer

Borrell points to Townsquare as a top digital performer among all local media companies. He bases that on what he calls “addressable” digital ad dollars, meaning those that are readily available to in-market media companies, like radio, TV, and newspapers

Companies like Townsquare Media should no longer be thought of as radio companies, he says, a belief shared by numerous broadcasters that have replaced the word “radio” in their company names with “media”

“Its digital ventures are fast-growing and quite impressive,” Borrell says, pointing to the company’s 300-person Townsquare Interactive workforce that focuses exclusively on digital ventures at the division’s base in Charlotte, NC

Townsquare Media has taken an approach “where the reps are truly marketing consultants, not radio reps who also have some digital products to sell,” Borrell says

Across its 67 markets, the company “holds a phenomenal share of addressable digital advertising”


Leading Research Firm, Borrell Associates, Singles out Townsquare as Top Digital Performer

__________________________ Sources: SEC Documents, company statements and Borrell Associates estimates, April 2019. Some data for Q1-Q3 2018 only. *Includes Salem’s non-radio ventures; radio-only percentage is 10.2%. Note: Represents Borrell estimates, and may make certain adjustments. According to the Company, In 2018, digital revenue represented nearly 30% of TSQ’s total net revenue.

© 2019 Borrell Associates Inc.

Percentage of Ad Revenue from Digital Sales for U.S. & Canadian Local Media Companies, 2018


Radio is a Stable Foundation

___________________________________________ 1. Nielsen Audio RADAR reports (127, 131, 135, 139), Mon-Sun, 12M-12M. 2. Edison Research, “Share of Ear,” Q2 2017, Q4 2017, Q1 2018 P18+. 3. Nielsen Total Audience Report Q2 2018. 4. Nielsen studies from 2014-2016, including Nielsen’s Catalina Radio Return on Advertising Spend studies.

Radio Reaches Everyone Radio’s Audience is Growing

Radio Delivers Results at an Attractive Price Radio Delivers a Local Connection

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

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

Reaches all the key demographics advertisers want (>90% reach among P18+, P18-34, P35-49, P50-64)(3)

Drives consumer action and positive ROI (~10x return on advertiser spend) (4)

Lower CPM than other forms of traditional media

New attribution tools, such as Analytic Owl, are providing ways to measure broadcast campaigns that have historically not existed

Unlike certain other traditional media, radio’s audience is growing

The introduction of streaming, mobile apps and smart speakers have helped to increase radio’s total audience

Radio usage has remained substantially unchanged since 1970, reaching >90% of Americans 12+ (1)

Radio dominates listening hours, with 47% vs. SiriusXM’s 7%, Pandora’s 5%, and Spotify’s 4% share of listening (2)

Radio reaches more people per week than any other media

Radio

PC

TV

Smartphone

Tablet

227M

216M

192M

112M

133M

Weekly Reach (P18+) (3) Radio’s Weekly Reach (P12+) (1)

244M 247M 247M 248M

2015 2016 2017 2018


Live Events

Live events are a natural extension of Townsquare’s core advertising offerings

Expands our audience and reinforces media brands through association

Unrivaled local presence and marketing strength

Complementary advertiser offering without cannibalizing other revenue streams

Monetizes the listener/consumer relationship

Expertise in local markets and ability to syndicate events across Townsquare markets

Townsquare creates, promotes and produces approximately 200 live events per year that are local, family oriented and community based in nature

Our events are largely perennial with strong customer loyalty

Low ongoing fixed cost, principally driven by innovation and human capital

Include concerts, expositions and other experiential events

Townsquare monetizes our audience relationships with profitable, recurring local live events brands

Select Local Live Event Brands


Key Financial Metrics

24.0%

LTM 6/30/19 PF Adjusted

EBITDA Margin

Steady Growth Strong Profit Margins

~$49M LTM 6/30/19

PF Adjusted EBITDA Less

Interest, Capex and Taxes /

$1.75 Per Share (2)

Stable Capital Structure Cash Generation

5.0%

YTD 2019 PF Net Revenue Growth

11.9%

YTD 2019 PF Adjusted EBITDA

Growth

____________________________________________________ Note: Please refer to page 1 for definitions of non-GAAP measures. Pro forma for the acquisition of three radio stations in Princeton, NJ on July 2, 2018 as if it had occurred on January 1, 2018. 1. Based on current LIBOR rates as of August 5, 2019. 2. Based on 27.9 million shares and warrants outstanding as of August 5, 2019.

5.9%

Weighted Average

Interest Rate (1)

No Maturities until 2022

$0.30

Annualized Dividend Per

Share, $0.075 Quarterly

Dividend Per Share

Current Equity Return


August 6, 2019 Earnings Call Highlights

_______________________________________________ Note: Please refer to page 1 for definitions of non-GAAP measures. All growth rates as compared to the prior year period. 1. Pro forma for the acquisition of three radio stations in Princeton, NJ on July 2, 2018 as if it had occurred on January 1, 2018.

YTD June 2019 net revenue increased 7.0%, and 5.0% on a pro forma basis (1)

Excluding political, net revenue increased 7.7%, and 5.7% on a pro forma basis (1)

YTD June 2019 Adjusted EBITDA increased 14.6%, and 11.9% on a pro forma basis (1)

YTD June 2019 Townsquare Interactive net revenue increased 31.2%

Townsquare Interactive’s subscriber base grew by 1,100 subscribers in Q2, to ~17,300

YTD June 2019 Townsquare Interactive Adjusted Operating Income increased 40.9%

Adjusted Operating Income margin of 31.9%

YTD June 2019 Advertising net revenue increased 5.0%, and 2.8% on a pro forma basis (1)

Excluding political, net revenue increased 5.9%, and 3.6% on a pro forma basis (1)

Declared next quarterly dividend payment of $0.075 per share, payable on November 15, 2019 to shareholders of record as of September 26, 2019


Q2 2019 Segment Financial Results

____________________________________________________ Note: Please refer to page 1 for definitions of non-GAAP measures. Pro forma for the acquisition of three radio stations in Princeton, NJ on July 2, 2018 as if it had occurred on January 1, 2018.

Actual Pro Forma

$ in millions Q2 2018 Q2 2019 Growth % Q2 2018 Q2 2019 Growth %

Advertising net revenue $86.3 $91.5 6.0% $88.3 $91.5 3.6%

Advertising net revenue ex. political

$85.0 $91.0 7.1% $86.9 $91.0 4.6%

Advertising Adj. Operating Income $27.7 $30.9 11.3% $28.5 $30.9 8.5%

Advertising Margin % 32.1% 33.7% 32.2% 33.7%

TSI net revenue $11.7 $15.3 30.8% $11.7 $15.3 30.8%

TSI Adj. Operating Income $3.4 $5.0 46.8% $3.4 $5.0 46.8%

TSI Margin % 29.2% 32.8% 29.2% 32.8%

Live Events net revenue $7.3 $6.3 -13.8% $7.4 $6.3 -14.9%

Live Events Adj. Operating Income $1.5 $1.6 10.9% $1.5 $1.6 9.5%

Live Events Margin % 19.9% 25.6% 19.9% 25.6%


YTD June 2019 Segment Financial Results

____________________________________________________ Note: Please refer to page 1 for definitions of non-GAAP measures. Pro forma for the acquisition of three radio stations in Princeton, NJ on July 2, 2018 as if it had occurred on January 1, 2018.

Actual Pro Forma

$ in millions YTD 2018 YTD 2019 Growth % YTD 2018 YTD 2019 Growth %

Advertising net revenue $157.8 $165.8 5.0% $161.3 $165.8 2.8%

Advertising net revenue ex. political

$155.8 $165.0 5.9% $159.3 $165.0 3.6%

Advertising Adj. Operating Income $46.6 $50.3 7.9% $47.6 $50.3 5.6%

Advertising Margin % 29.5% 30.3% 29.5% 30.3%

TSI net revenue $22.5 $29.5 31.2% $22.5 $29.5 31.2%

TSI Adj. Operating Income $6.7 $9.4 40.9% $6.7 $9.4 40.9%

TSI Margin % 29.7% 31.9% 29.7% 31.9%

Live Events net revenue $13.0 $11.5 -11.5% $13.1 $11.5 -12.4%

Live Events Adj. Operating Income $2.9 $2.9 -2.6% $3.0 $2.9 -3.1%

Live Events Margin % 22.7% 25.0% 22.6% 25.0%


Balance Sheet, Liquidity & Ownership

Capital Allocation Priorities Ownership (as of 8/5/19)

6/30/19 Balance Sheet & Liquidity

Invest in organic growth opportunities

Reduce net leverage

Prudently pursue attractively valued acquisition opportunities

$ in millions Maturity Pricing

Cash $62.8

Revolver ($50 million) 0.0 2022 (1) L +250bps

Term Loans 282.3 2022 L +300bps, 1% Floor

Capitalized Obligations 0.0

Total Secured Debt $282.3

Senior Unsecured Notes 278.1 2023 6.500%

Total Debt $560.5

Secured Debt Leverage (2) 2.8x

Total Debt Leverage (2) 5.5x

Net Debt Leverage (2) 4.9x

__________________________________________________ Note: Please refer to page 1 for definitions of non-GAAP measures. 1. On April 30, 2019, the Company entered into an amendment under its existing credit agreement to extend the maturity date of the existing Revolver to April 1, 2022, with a springing maturity six months inside of the Term Loan maturity date. 2. Pro forma Adjusted EBITDA for the twelve months ended June 30, 2019 was $101.3 million. Pro forma for the acquisition of three radio stations in Princeton, NJ on July 2, 2018 as if it had occurred on January 1, 2018. 3. Each warrant is exercisable for one share of Class A common stock, at an exercise price of $0.0001 per share. The aggregate exercise price for all warrants currently outstanding is $898.

(shares in millions) # of

Votes Primary Holders

Class A Common Stock 14.3 1 Public & MSG

Class B Common Stock 3.0 10 Oaktree & Management

Class C Common Stock 1.6 0 MSD

Class A Warrants (3) 9.0 0 Oaktree

Total Shares + Warrants 27.9 ~$113M of liquidity (including cash and undrawn revolver)

Extended revolver maturity from April 2020 to April 2022 Townsquare’s multi-class structure is driven largely by FCC considerations

Class B (high vote) and Class C (no vote) shares revert to Class A (1 vote) shares upon a sale

Equity Ownership

Others 31%

Mgmt 6% MSD

Capital 6%

MSG 12%

Oaktree Capital

Management 45%