The following management's discussion and analysis is intended to provide the reader with an overall understanding of our financial condition, results of operations, cash flows and sources and uses of cash. This section also includes general information about our business and a discussion of our management's analysis of certain trends, risks and opportunities in our industry. In addition, we also provide a discussion of accounting policies that require critical judgments and estimates. This discussion should be read in conjunction with our Unaudited Consolidated Financial Statements and related notes appearing elsewhere in this quarterly report.

Note About Forward-Looking Statements

This report includes estimates, projections, statements relating to our business plans, objectives and expected operating results that are "forward-looking statements" within the meaning of the Private Securities Litigation Reform Act of 1995, Section 27A of the Securities Act of 1933, as amended and Section 21E of the Securities Exchange Act of 1934, as amended (the "Exchange Act"). Forward-looking statements often discuss our current expectations and projections relating to our financial condition, results of operations, plans, objectives, future performance and business. You can identify forward-looking statements by the fact that they do not relate strictly to historical or current facts. These statements may include words such as "aim," "anticipate," "estimate," "expect," "forecast," "outlook," "potential," "project," "projection," "plan," "intend," "seek," "believe," "may," "could," "would," "will," "should," "can," "can have," "likely," the negatives thereof and other words and terms. Actual events or results may differ materially from the results anticipated in these forward-looking statements as a result of a variety of factors. While it is impossible to identify all such factors, factors that could cause actual results to differ materially from those estimated by us include the impact of general economic conditions in the United States, or in the specific markets in which we currently do business, including as a result of the COVID-19 pandemic, (the extent of which will depend on future actions and outcomes that are highly uncertain and cannot be predicted, including the scope, severity and duration of the pandemic, the actions taken to contain the pandemic or mitigate its impact, and the direct and indirect economic and financial market effects of the pandemic, the containment measures and the pace of the economic and financial market recovery), any civil unrest or violence, the impact of several material weaknesses in internal control over financial reporting that have been identified, which resulted in the restatement of certain of our Consolidated Financial Statements and created additional risks and uncertainties, including limiting our access to certain capital markets activities and increasing litigation risk, industry conditions, including existing competition and future competitive technologies, the popularity of radio as a broadcasting and advertising medium, cancellations, disruptions or postponements of advertising schedules in response to national or world events, including the COVID-19 pandemic, our ability to develop and maintain digital technologies and hire and retain technical and sales talent, our dependence on key personnel, our capital expenditure requirements, our continued ability to identify suitable acquisition targets, and consummate and integrate any future acquisitions, legislative or regulatory requirements, risks and uncertainties relating to our leverage and changes in interest rates, our ability to obtain financing at times, in amounts and at rates considered appropriate by us, our ability to access the capital markets as and when needed and on terms that we consider favorable to us and other factors discussed in this section entitled "Management's Discussion and Analysis of Financial Condition and Results of Operations" in this report and under "Risk Factors" in our 2020 Annual Report on Form 10-K, as well as other risks discussed from time to time in our filings with the SEC. Many of these factors are beyond our ability to predict or control. In addition, as a result of these and other factors, our past financial performance should not be relied on as an indication of future performance. The cautionary statements referred to in this section also should be considered in connection with any subsequent written or oral forward-looking statements that may be issued by us or persons acting on our behalf. The forward-looking statements included in this report are made only as of the date hereof or as of the date specified herein. We undertake no obligation to publicly update or revise any forward-looking statements, whether as a result of new information, future events or otherwise, except as required by law.

Format of Presentation

Townsquare is a community-focused digital media, digital marketing solutions and radio company focused outside the Top 50 markets in the U.S. Our assets, as of June 30, 2021, include a digital marketing subscription business (Townsquare Interactive) providing websites, search engine optimization, social platforms and online reputation management for approximately 24,950 small to medium sized businesses, a proprietary digital programmatic advertising technology with an in-house demand and data management platform (Townsquare Ignite), a portfolio of 322 local terrestrial radio stations in 67 U.S. markets with more than 330 corresponding local news and entertainment websites and apps, along with a network of national music brands and websites. Many of our radio stations are considered market leaders and we also participate in the digital, mobile, video and social media arena. In addition, we create, promote and produce a diverse range of live events, including, concerts, expositions and other experiential events within and beyond our radio markets.


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Our integrated and diversified product and service offerings enable local, regional and national advertisers to target audience engagement across multiple platforms, including on-air, online and at live events. We believe our product and service offerings, combined with our leading market position in small and mid-sized markets, enable us to generate higher total net revenue per audience member than radio station owners focused on larger markets.

The Company has identified three operating segments, which are Advertising, including broadcast and digital advertising products and solutions, Townsquare Interactive, our digital marketing solutions business and Live Events, including concerts, expositions and other experiential events.

Advertising

Our Advertising segment includes the broadcast operations of our radio stations, together with our owned and operated websites and the various digital advertising solutions we offer, including Townsquare Ignite, our digital programmatic advertising platform. Our primary sources of net revenue are the sale of advertising on our radio stations, owned and operated websites, radio stations' online streams and mobile applications. Additionally, we offer precision customer targeting solutions to advertisers through Ignite. Combining first and third-party audience and geographic location data, Ignite is able to hyper-target audiences for our local, regional and national advertisers, providing them the ability to reach a high percentage of their online audience. Ignite delivers these solutions across desktop, mobile, connected TV, email, paid search and social media platforms utilizing display, video and native executions.

Our sales of advertisements are primarily affected by the demand for advertising from local, regional and national advertisers and the advertising rates we charge. Advertising demand and rates are based primarily on our ability to attract audiences to our various products in the demographic groups targeted by advertisers, as measured principally by various services on a periodic basis. We endeavor to develop strong audience loyalty and believe that the diversification of formats on our radio stations and websites helps to insulate our radio stations and websites from the effects of changes in musical tastes of the public with respect to any particular format. We believe that the sale of our online and mobile advertisements, which currently have rates per advertisement that are less than those of terrestrial radio advertisements, has not negatively impacted our terrestrial radio advertising net revenue. Should a significant and sudden shift in demand for these products toward online and mobile occur, there could be a material adverse impact on our financial condition and results of operations if we are unable to increase rates accordingly. However, we believe that as a result of our strong brands and quality online and mobile offerings we are well positioned to increase rates as demand increases for these products.

Townsquare Interactive

Townsquare Interactive offers digital marketing solutions, on a subscription basis, to small and mid-sized local and regional businesses in small and mid-sized markets across the United States, including but importantly not limited to the markets in which we operate radio stations. Our primary source of Townsquare Interactive net revenue is traditional and mobile-enabled website development and hosting services, e-commerce solutions, search engine organic traffic and online directory optimization services, online reputation monitoring, social media management, appointment scheduling services, email marketing services, and website retargeting often packaged together as a comprehensive digital marketing solution.

Live Events

Our primary source of Live Events net revenue is ticket sales. Our Live Events also generate substantial net revenue through the sale of sponsorships, food and other concessions, merchandise and other ancillary products and services. Live Event ticket pricing is based on consumer demand for each event and the geographic location and target audience demographic of each event. Unforeseen events such as inclement weather conditions can have an adverse impact on our net revenue. In certain cases, we mitigate this risk with insurance policies, which cover a portion of lost revenue as a result of unforeseen events including inclement weather. Legislative and regulatory responses to the COVID-19 pandemic required us to cancel nearly all live events beginning in March 2020. We have resumed certain live events in the second quarter of 2021, however there continues to be uncertainty surrounding the scheduling of live events in light of the COVID-19 pandemic.

Overall

We strive to maximize our net revenue by managing our advertising inventory and adjusting prices based on supply and demand, and by broadening our base of advertisers and subscribers. Our selling and pricing activities are based on


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demand for our advertising inventory and, in general, we respond to this demand by varying prices rather than by varying our target inventory levels. The optimal number of advertisements available for sale depends on the platform and in the case of our radio stations, their online streams and mobile applications, the programming format of a particular radio station. Each of our advertising products has a general target level of available inventory. We seek to broaden our base of advertisers in each of our markets by providing a wide array of audience demographic segments across our platforms, thereby providing each of our potential advertisers with an effective means of reaching a targeted demographic group.

Our advertising contracts are generally short-term. In the media industry, companies, including ours, sometimes utilize barter agreements that exchange advertising time for goods or services such as travel or lodging, instead of cash.

Our most significant expenses are sales, programming, digital, marketing and promotional, engineering, and general and administrative expenses. We strive to control these expenses by closely monitoring and managing each of our local markets and through efficiencies gained from the centralization of finance, accounting, legal and human resources functions and management information systems. We also use our scale and diversified geographic portfolio to negotiate favorable rates with vendors where feasible.

A portion of our expenses are variable. These variable expenses primarily relate to sales costs, such as commissions, as well as certain programming costs, such as music license fees, and certain costs related to production. Marketing and promotions expenses are discretionary and are primarily incurred in an effort to maintain and/or increase our audience share. Other programming, digital, engineering and general and administrative expenses are primarily fixed costs.

Seasonality

Our net revenue varies throughout the year. Historically, our first calendar quarter produces the lowest net revenue for the year, as advertising expenditures generally decline following the winter holidays. However, due to the COVID-19 pandemic, the seasonality of our net revenue for the year ended December 31, 2020 was materially impacted and our second quarter produced our lowest net revenue for 2020. During even-numbered years, net revenue generally includes increased advertising expenditures by political candidates, political parties and special interest groups. Political spending is typically highest during the fourth quarter. Our operating results in any period may be affected by the incurrence of advertising and promotion expenses that typically do not have an effect on net revenue generation until future periods, if at all.

Macroeconomic Indicators

The U.S. economy and financial markets may continue to experience volatility due to the COVID-19 pandemic, including as a result of the development of COVID-19 variants, vaccination rates and government legislative and regulatory responses. The effects of the COVID-19 pandemic began to impact our operations in early March 2020, and included significant advertising cancellations and material declines in the purchase of new advertising by our clients. Declines in forecasted traditional broadcast revenue in the markets in which we operate, the impact of the COVID-19 pandemic on market and economic conditions, and the corresponding impacts to our risk premium, contributed to approximately $107.1 million impairments to the carrying values of our FCC license intangible assets during the first half of 2020, of which $28.7 million and $78.4 million was recognized during the three months ended June 30, 2020 and March 31, 2020, respectively. Additionally, we canceled nearly all live events beginning in March 2020. At the end of the first quarter of 2020, we reduced our workforce through the termination or layoff of approximately 135 full-time employees.

As local public health conditions have begun to improve, we experienced a recovery in advertising revenue, following the sequential improvements we observed during each of the third and the fourth quarters of 2020. However, revenue continues to remain below the levels we experienced during the same period in 2019, with the exception of our Townsquare Interactive segment. Net revenue for the Townsquare Interactive segment has increased $9.7 million, or 33%, as compared to the first half of 2019 due to continuing to achieve net subscriber growth throughout the COVID-19 pandemic. While we resumed certain live events during the second quarter of 2021, there continues to be uncertainty surrounding the scheduling of live events.

During the first six months of 2021, we continued to maintain the precautionary measures that were instituted in 2020 to address the potential impact to our consolidated financial position, consolidated results of operations, and liquidity, including wage reduction efforts such as the temporary suspension of the Company's match on employee contributions to the Company's defined contribution plan, the deferral of the payment of certain payroll taxes until December 31, 2021 and 2022 under the Coronavirus Aid, Relief, and Economic Security Act ("CARES Act") and controlling non-essential capital


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expenditures. Additionally, our board of directors determined to cease payment of quarterly cash dividends, following the payment of our 2020 first quarter dividend of $2.1 million, paid on May 15, 2020.

The full extent of the COVID-19 pandemic impact will depend on future actions and outcomes, all of which remain fluid and cannot be predicted with confidence, including the scope, severity and duration of the pandemic, the short-term and long-term economic impacts of the COVID-19 pandemic (including the continued effect on advertising activity, consumer discretionary spending and our employees in the markets in which we operate), further actions taken to mitigate the impact of the pandemic, and the pace of continued economic and financial market recovery when the COVID-19 pandemic subsides, among others.



OVERVIEW OF OUR PERFORMANCE

Changes in our Business

Recent Developments

On January 6, 2021, the Company completed the private offering and sale of $550.0 million aggregate principal amount of 6.875% senior secured notes due 2026 (the "2026 Notes") at an issue price of 100.0%. The net proceeds from the 2026 Notes, together with cash on hand, were used to repay: (i) all outstanding borrowings under the 2015 senior secured credit facility, which included a seven year $275.0 million term loan facility (the "Term Loans") with $272.4 million principal amount outstanding and $2.1 million in accrued interest, (ii) all of the outstanding $273.4 million of principal amount of 6.5% Unsecured Senior Notes due in 2023 (the "2023 Notes"), a prepayment premium of $4.4 million, and $5.1 million in accrued interest, and (iii) fees and expenses related thereto. The Company also terminated its revolving credit facility and all other obligations thereunder were repaid effective January 6, 2021.

The Company incurred approximately $13.6 million of fees and expenses in connection with the issuance of the 2026 Notes, of which approximately $9.4 million were capitalized and are being amortized over the remaining term of the 2026 Notes using the effective interest method. The Company recognized a $4.9 million loss on the early extinguishment of debt during the three months ended March 31, 2021, due to a $3.1 million portion of the 2023 Notes prepayment premium and the write-off of $1.8 million of unamortized debt discount and deferred financing fees previously capitalized in connection with the senior secured credit facility and 2023 Notes. The Company recognized a $1.1 million loss on the modification of Terms Loans and 2023 Notes during the three months ended March 31, 2021, which is primarily related to a portion of fees and expenses incurred related to the issuance of the 2026 Notes.

Refer to Note 7, Long-term Debt, in the accompanying Notes to Consolidated Financial Statements for additional information related to our 2026 Notes.

Stock Repurchase

On January 24, 2021, the Company entered into a stock repurchase agreement with certain affiliates of Oaktree Capital Management L.P. ("Oaktree") to repurchase 606,484 shares of the Company's Class A common stock, 2,151,373 shares of the Company's Class B common stock and 7,242,143 warrants to purchase Class A Common Stock, or such greater number of securities as the Company may elect. On March 9, 2021, the repurchase was consummated and the Company elected to repurchase all of the outstanding securities held by Oaktree, including 1,595,224 shares of Class A Common Stock, 2,151,373 shares of Class B Common Stock and 8,814,980 warrants for an aggregate purchase price of $80.4 million, or $6.40 per security.

In connection with the closing under the stock repurchase agreement, on March 8, 2021, the Company and Oaktree entered into a settlement agreement (the "Settlement Agreement"), pursuant to which, among other things, the Company agreed to pay $4.5 million to Oaktree as follows: (i) $1.5 million on April 1, 2021; (ii) $1.0 million on July 1, 2021; (iii) $1.0 million on October 1, 2021; and (iv) $1.0 million on November 10, 2021. The Settlement Agreement also includes customary mutual releases from claims, demands, and damages related to the stock repurchase agreement.

Refer to Note 9, Stockholders' Equity, in the accompanying Notes to Consolidated Financial Statements for additional information related to the stock repurchase.


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Highlights of Our Financial Performance

Certain key financial developments in our business for the three months ended June 30, 2021 as compared to the same period in 2020 are summarized below:

•Net revenue increased $33.3 million, or 44.9%, primarily driven by a $28.8 million increase in our Advertising net revenue as a result of increases in the purchase of new advertising by our clients, an increase of $3.3 million in our Townsquare Interactive net revenue as a result of additional subscribers, and an increase of $1.2 million in our Live Events net revenue as we resumed certain live events.

•Excluding revenue related to political advertising of $0.8 million and $0.9 million and Live Events net revenue of $1.2 million and $32.0 thousand for each of the three months ended June 30, 2021 and 2020, respectively, net revenue for the three months ended June 30, 2021 as compared to the same period in 2020, increased $32.2 million or 44.1% to $105.4 million.

•Excluding revenue related to political advertising of $0.8 million and $0.9 million for the three months ended June 30, 2021 and 2020, respectively, net revenue for the three months ended June 30, 2021 as compared to the same period in 2020 increased $33.4 million, or 45.7% to $106.6 million and Advertising net revenue increased $28.9 million, or 51.4%, to $85.2 million.

•Operating income increased $57.5 million from an operating loss of $33.7 million for the three months ended June 30, 2020 to operating income of $23.8 million for the three months ended June 30, 2021. Operating income increased due to an increase in net revenue of $33.3 million; $28.7 million as a result of impairment charges incurred during the three months ended June 30, 2020, primarily pertaining to FCC licenses in 35 of our 67 local markets that were not repeated in 2021; and $2.1 million as a result of lower corporate expenses primarily due to lower professional fees, partially offset by a $7.2 million increase in direct operating expenses. Our Advertising segment reported operating income of $25.7 million which represents an increase of $53.5 million as compared to an operating loss of $27.8 million for the three months ended June 30, 2020, primarily due to a $28.8 million increase in net revenue and $28.7 million as a result of impairment charges incurred during the three months ended June 30, 2020 that were not repeated in 2021, partially offset by $4.2 million increase in direct operating expenses. Townsquare Interactive's operating income for the three months ended June 30, 2021 was $5.7 million, an increase of $0.7 million from the same period in 2020, primarily due to growth in net subscribers. Our Live Events segment reported operating income of $0.5 million, as compared to an operating loss of $0.2 million for the three months ended June 30, 2020, an increase of $0.6 million due to the scheduling live events.

Certain key financial developments in our business for the six months ended June 30, 2021, as compared to the same period in 2020 are summarized below:

•Net revenue for the six months ended June 30, 2021 as compared to the same period in 2020, increased $28.6 million, or 17.1%, primarily driven by an increase of $24.0 million in our Advertising net revenue as a result of an increase in the purchase of new advertising by our clients, an increase of $5.8 million in our Townsquare Interactive net revenue due to additional net subscribers, partially offset by $1.2 million decrease in our Live Events net revenue as a result of fewer live events during the first six months of 2021 as compared to the same period in 2020, due to the COVID-19 pandemic.

•Excluding revenue related to political advertising of $1.2 million and $2.2 million and Live Events net revenue of $1.2 million and $2.4 million for each of the six months ended June 30, 2021 and 2020, respectively, net revenue for the six months ended June 30, 2021 as compared to the same period in 2020 increased $30.8 million, or 18.9%, to $193.7 million.

•Excluding revenue related to political advertising of $1.2 million and $2.2 million for the six months ended June 30, 2021 and 2020, respectively, net revenue for the six months ended June 30, 2021 as compared to the same period in 2020 increased $29.6 million, or 17.9% to $194.9 million and Advertising net revenue increased $25.0 million, or 19.3%, to $154.5 million.


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•Operating income increased $138.4 million as compared to an operating loss of $105.8 million for the six months ended June 30, 2020 to operating income of $32.6 million for the six months ended June 30, 2021. Operating income increased for the six months ended June 30, 2021 due to an increase of $28.6 million in net revenue as discussed above; a decrease of $107.6 million of total impairment charges; and $4.4 million as a result of lower corporate expenses primarily due to lower professional fees. Our Advertising segment reported operating income of $40.4 million which represents an increase of $133.7 million from the six months ended June 30, 2020 due to a $24.0 million increase in net revenue as discussed above; total impairment charges of $107.7 million in 2020 that did not repeat in 2021; and a decrease in direct operating expenses of $2.1 million. Townsquare Interactive's operating income for the six months ended June 30, 2021 was $11.0 million, an increase of $1.7 million from the same period in 2020 due to net subscriber growth. Our Live Events segment reported operating income of $0.3 million, an increase of $0.1 million from the six months ended June 30, 2020.

•Cash and cash equivalents decreased $58.1 million from $83.2 million as of December 31, 2020 to $25.1 million as of June 30, 2021. Excluding the $80.4 million in cash consideration paid for the repurchase of the Oaktree securities, cash and cash equivalents increased $22.3 million at June 30, 2021, as compared to December 31, 2020.


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