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From Records to Radio: Bill Wilson's Journey to Landing a Digital Media Empire


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The Interview Discusses:

  • Bill Wilson’s rise from a data-driven marketer at Arista Records to helming a digital-first local media empire.
  • The extraordinary experience of working with Clive Davis. 
  • How he utilized traditional radio as a “trojan horse” to build a digital media company.
  • The competitive advantage of  operating in smaller markets.
  • Why a local content strategy is so differentiated in today’s environment.
  • Bill’s thoughts on capital allocation.
  • His views on running a publicly traded company.
  • Why he believes Townsquare’s stock is intrinsically undervalued.
  • How he intends to unlock shareholder value if the stock price languishes.
  • And much more…

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About Bill Wilson:

Mr. Wilson joined Townsquare in September 2010 and previously served as Co-Chief Executive Officer and Executive Vice President and Chief Content & Digital Officer of the Company. Prior to joining Townsquare, Mr. Wilson was President of AOL Media from 2006 to May 2010 where he had overall responsibility for AOL’s global content strategy. In his nine years at AOL, he also served in a number of roles including President, AOL Programming & Studios and Executive Vice President; and under his leadership, AOL’s content sites grew to reach more than 75 million monthly unique visitors domestically and over 150 million worldwide.

Prior to joining AOL in 2001, Mr. Wilson served as Senior Vice President for Worldwide Marketing at Bertelsmann Music Group (BMG), which he joined in 1992, and was responsible for worldwide marketing including artist, digital and non-traditional marketing across more than 50 countries for the world’s biggest artists including Dave Matthews Band, OutKast, Foo Fighters, Whitney Houston, Annie Lennox, Santana and numerous major recording artists over his tenure at BMG.  Mr. Wilson started his career at BMG subsidiary Arista Records under the guidance of Clive Davis and Richard Sanders, where he was a product manager working with artists across numerous genres including Notorious B.I.G., TLC,  Sarah McLachlan, Kenny G and Spiritualized.

Mr. Wilson won an Emmy Award in 2006 for the record setting Live 8 program and was named to the Hollywood Reporter’s “Digital Power List” in 2008, which profiles the 50 people who most influence the creation and distribution of content online. In addition, he was profiled in Crain’s New York Business’ “40 under Forty” and Billboard’s “Power Players” in Digital Entertainment in 2005, as well as Hollywood Reporter’s “Next Generation” in 2003, and Radio Ink’s “Most Powerful in Radio” in 2018 - 2023. Mr. Wilson was voted the Radio Board Chair of the National Association of Broadcasters (“NAB”) in June 2021, after serving on the Executive Board of the NAB since 2020 and previously serving as a NAB Board Member. Mr. Wilson was also recently recognized as 2021 “Executive of The Year” by Radio Ink.

Mr. Wilson graduated summa cum laude from the State University of New York at Stony Brook with a B.A. in economics and a B.S. in business management and earned a M.B.A. with honors in finance and marketing from Rutgers University’s Graduate School of Management.


Click Below to Read the Interview Transcript

Transcript of the Interview With Bill Wilson:

Jonathan Boyar 00:05

Welcome to the World According to Boyar, where we bring top investors, bestselling authors and business leaders to show you the smartest ways to uncover value in the stock market. I'm your host, Jonathan Boyar. I'm really excited about today's special guest, bill Wilson, CEO of publicly traded company Townsquare Media. Prior to joining Townsquare. Bill Wilson, CEO of publicly traded company Town Square Media. Prior to joining Town Square, Bill was president of AOL Media from 2006 to 2010. Before working at AOL, bill started his career in the record industry, where he worked under the great Clive Davis. It's especially exciting to have Bill on the show today as, in full disclosure, I personally, as well as my clients, own shares in Town Square, and Bill and his team have done a fantastic job, both operationally and in terms of capital allocation, which I want to discuss with him. We also recently featured Town Square in our March 2024 Substack Report, stating that, in our opinion, it is intrinsically undervalued. Without further ado, bill, welcome to the show.

Bill Wilson 01:08

Jonathan, thank you so much for having me on the show.

Jonathan Boyar 01:11

As I said, I'm really excited and, before digging into Townsquare, just love to talk a little bit about your early career. You started in the record business after finishing your MBA. What was that like?

Bill Wilson 01:23

Well, I think I was very, very fortunate. Early on in my life I had a very distinct perspective on what I wanted to do, which is rare. I have two children now, one graduating college and one just in college as a freshman, and when I was in middle school. I grew up in Teaneck, new Jersey, which I think also influenced my career and who I became as a person, because it was the first town in the United States to voluntarily desegregate in 1965. And my parents moved there in 1968. So it was a very diverse community which I think helped form who I am today.


But in junior high school I read Clive's autobiography. I think it was a biography at the time. Clive Davis, that is, he had just started Arista Records after leaving Sony. Clive Davis, that is, he had just started Arista Records after leaving Sony and I was a big music fan. My family, I was never a musician in terms of capable skills in music, but I loved music and my family always listened to music and that had a profound impact on me. So, I remember reading that biography and saying one day I want to run an entertainment business, particularly a record label at the time.


So, fast forward, graduating with my MBA at Rutgers University for literally two years, Jonathan, I wrote everybody who got promoted in the record business. There was a trade publication called Billboard and there was a section called the Executive Turntable, and no exaggeration. For two years I would go to the public library because it was a very expensive subscription so I couldn't afford it at the time and I would literally write a letter to everybody who got promoted, if you were from mailroom to mailroom manager. And one of the people who got promoted was Jack Rovner. He had left Sony and joined Arista and I interviewed with Jack Rovner for about a year and I was fortunate enough to be hired as Richard Sanders assistant, who was an incredible mentor. I would not be in the position I am today without Richard Sanders' help. And it was a dream come true. I always wanted to work for either Clive Davis, who was at Arista, or Mo Austin at Warner Brothers, and I kind of manifested it and it happened.

Jonathan Boyar 03:17

That's amazing and shows the value of persistency for those who have been living under a rock. Persistency for those who have been living under a rock. You know Clive Davis is legendary, discovered Whitney Houston, helped with Billy Joel, Bruce Springsteen, Aerosmith, basically anyone who's been in the music business over the past 40, 50 years. Were you able to work with him at all?

Bill Wilson 03:41

Yeah, directly with him. So, you know, the book I read was published in 1975. It was called Inside the Record Business and it was fascinating. It's still on Amazon they're charging $50 these days but definitely worth reading. He's actually had a more recent autobiography and a movie on Netflix for those interested. But not only did I work directly with him, it was probably my earliest influence of a leader running a company.


The first thing that happened is SoundScan came about in 1991. And if you're familiar with the music industry, SoundScan was the first time it was actually tracking sales of records accurately. Before they would just ship them out and there would be some qualitative conversation on the phone how many of these did you sell by Sam Goody or the Wiz and so forth? And then SoundScan came out in 1991 and it was to the copy of how many CDs, how many vinyls were being sold. And I joined the company in 1992. And in the marketing department as an assistant, I started obviously at the bottom and working for Richard Sanders who was running marketing, and Clive would track everything you know visits to radio stations, visits to record stores, promo tours, concerts, and there'd be reports about every artist. And I had a economics background and I actually taught econometrics as an undergraduate at SUNY Stony Brook and so I started talking to Richard about hey, we can actually look at all these variables and come up with cause and effect. So, if an artist went on a promo tour or if they went to a radio station, did it have an impact and we could correlate that to the market. They did that in and the sound scan. And so, I started creating a report and I gave it to Richard and Richard a lot of people in these days wouldn't have done that he put my name on the report. He could have easily put his name on the report and sent it to Clive. So, he's like hey, just call it the Wilson Report. So, to Clive. So he's like hey, just call it the Wilson Report. So, I called it the Wilson Report.


And after two or three weeks I get a call from Clive's assistant, Rose, and she's like Clive would like you to come up. And she's like I come in and he's like what is this? How are you doing this? How are you calculating these variables and these cause and effects? And I walked him through a model that I had created and he was fascinated.


He gave me so much attention and in essence, every week he started distributing it to all of his leaders in the company and he has a very infamous luncheon meeting every week.


It was every Thursday, started at one o'clock and it would literally go from one until he was done, and he would go through every artist on the label and he started to use, obviously, some of the information that I provided, but obviously a lot of other information. So, going back to your original question, I had direct contact with him on a daily basis and it helped his level of detail, as you said in the introduction, from Whitney Houston to Sarah McLaughlin, to Kenny G, to Aretha Franklin, Carlos I mean, the list just goes on and on and on. When I was starting out, I was working with really small artists a band called Spiritualized out of London and what really struck me, Jonathan, is he cared just as much about an artist who was selling 20,000 copies as he did about Whitney Houston and he gave that the attention. And that struck me as a leader, that it's a responsibility. You have these brands and you're investing in these people's lives you have to put as much attention on each one of them and that stuck to me to this day.

Jonathan Boyar 06:42

That's amazing put as much attention on each one of them, and that stuck to me to this day. That's amazing. Besides that the attention to detail, because I'm always fascinated with what makes someone a fantastic leader, what else made him great? He's known as the man with the golden ear, or whatever it is, but why was he so much better than everyone else?

Bill WilsonHost06:59

I think his passion, first and foremost, his passion for the music, his passion for the artistry. I've never seen an individual work as hard as somebody did. And I remember talking to him at times and he didn't view it as work, he viewed it as almost a calling. I mean, I remember when Whitney Houston would go up against Mariah Carey back in 1993, 94. He would start the meeting by saying you know how are we doing with Whitney's new single? And the head of R&B or pop radio promotion would say we're doing great, We've got 99 spins on this station, We've got 67 on these.


And what also struck me, Jonathan, he never looked at any piece of paper and he said well, I don't understand how you could be pleased with 99 spins when Mariah, on that same station, has 102 spins for her song with Boyz II Men. How can you be pleased if Mariah Carey is on top? And literally, Jonathan, he would do this for like the top 15, 20 markets without ever looking at a piece of paper. And in this meeting we'd go literally from anywhere, the shortest four hours. Sometimes he'd have to order in dinner at six or seven o'clock. And I think it's that passion and that level of detail and he made everybody better in the room because they knew they needed to bring their A game every week. You couldn't walk into that meeting and not be prepared. So, I think it's him as a leader, but also the culture he built of accountability. We have an accountability to these people's lives and profession and we're not going to take that lightly.

Jonathan Boyar 08:17

For those of you who are not familiar with Townsquare maybe just give a brief background of what Townsquare is and what you do, etc.

Bill Wilson 08:26

Yeah. So, Townsquare is a local media company focused on really the whole premise of the company originally was use radio as a Trojan horse to build a digital first company, and this was formed in 2010, originally with about 17 markets, 60 radio stations and one of the important things, Jonathan was, the premise all along was A build a digital company on the back of a radio company and two focus on markets outside the top 50. For two reasons One, radio means a lot more in markets outside the top 50. And we can go through some of the statistics that bear that out. And two, the digital competition for digital advertising and digital marketing solutions is going to be a lot less competitive in markets outside the top 50 versus New York, LA, Chicago and Nashville. So we're very proud of the radio business and to me, we would never have had the success over the last 14 years in transforming into a digital first company without the DNA of radio.


I grew DNA of radio, I grew up on radio. It's one of the reasons I decided to take this opportunity is, you know, my parents would be watching TV upstairs, I'd be having headphones on downstairs listening to New York City radio, living in Teaneck, New Jersey, and I just know that companionship, that connection is unparalleled. There's nothing like that from watching a local newscaster on TV or reading a journalist, and so I really felt like harnessing that power of radio to build a digital connection and make sure people who joined radio to inform and entertain their communities were relevant for decades and decades and decades, no matter what happened with the radio audience, and thankfully, over the last decade we've transformed the company from a successful radio company to a digital-first company that also owns radio stations, with now over 50% of our revenue and 50% of our profits coming from our digital divisions. Can you?

Jonathan Boyar 10:16

Talk a little bit more about the hyper-local importance. Why is that so important in today's day and age?

Bill Wilson 10:25

Yeah, I mean you think about what's happened. We call them news deserts, right. So going back almost six, seven, eight years now, the newspapers, particularly in our size markets but I think across the US, but particularly in markets outside the top 50, have really been decimated. There's close to 2000 newspapers that have been folded in the last decade and the pandemic and COVID really accelerated some of those challenges. So, it's a great business for us, but it's also, we feel, like a calling to make sure that these smaller markets are informed and have trustworthy journalists.


You know a lot of our hires over the last five years have actually come from the local newspapers. As they shed jobs and focus more on national content. We've actually picked up those reporters to serve that need and we have them on the air. But we also have digital-only reporters creating content that if you go to any one of our 300-plus local websites, I think most people would look at them as almost like a local newspaper. They wouldn't recognize that a radio company was behind them. So, we think it's incredibly differentiated. We reach one in two adults listening to the AM FM stations of ours because they're so local.

Jonathan Boyar 11:33

Can you explain that again? That statistic is unbelievable.

Bill Wilson 11:37

Yes, so on average we're in 74 markets. On average we own four FM radio stations and two AM, so six markets in a station on average. When you look at those six markets on a weekly basis, we reach one in two adults just through the AM FM broadcast, so 50% of the adult population. You go back to asking about how I got from AOL to Townsquare earlier. That was Stephen Prices who at that time was the CEO. Stephen Prices and Stu Rosenstein were the co-founders of the company, had the vision early on. Stu's not only a co-founder but also our current CFO. And Stephen's kind of pitch to me was if I just walked into a room and told you that you could market for free to 50% of the adult population and you can go out and create any digital products over the next five to 10 years, would that be compelling to you? I'm like, yeah, of course, if you can market the 50% of the adult population, it goes. Well, that's what we can do, and we can do that through our AM FM radio stations and we have the benefit of a great cashflow business that we think is going to be relatively stable for the next five to 10 years. And, to your point. It's incredibly eye opening. In the top 50 markets, say New York City, where you're sitting the number one market share is probably about 20%, so reaching obviously two in 10 adults. So, our company reaches one in two adults. So that, in essence, is one of the reasons we've had so much success with our digital products is because we can market for free for 50% of the adult population.


And if anybody who's listening to your podcast knows, radio overall has been a great reach medium. It's actually now the number one reach medium in America because TV and cord cutting over the last five years has accelerated so much that TV used to be the number one reach medium. Now the radio is. The challenge for the radio industry at large is time spent listening has been decreasing. For Townsquare that's not the case. So, our reach is rock stable 50% of the adult population and our time spent listening is rock stable.


So that's one of the reasons we're generating so much free cash flow because we have a relatively stable, what I call a traditional cash cow. It is a declining business over time, but it has so many great characteristics. A: the 50% adult population and the 30% margin in terms of cashflow. It gets lumped into the rest of the industry which has struggled, when you're lumped into an industry that three of the largest players iHeart, odyssey and Cumulus have either all been in or are currently in bankruptcy. In the last three or four years we kind of just got lumped into that. I appreciate your time and research on the company because when you peel back and start to look at what we've actually done in terms of the transformation and recognize that when people look up in three to five years the price is going to be much higher. Let's take off what we can at this point with the cash on hand we have.

Jonathan Boyar 14:31

So why are your stations doing so much better than other ones, let's say, not the ones that are in the top 50 in the country, but why are your stations doing better than other kind of small and mid-sized markets?

Bill Wilson 14:46

Yeah, I think it's a combination of a couple of factors. First of all, what you said when you look at all the other major public radio companies, there's really nobody at scale public or private who focuses on markets outside the top 50. That's true not only of radio, but when you think about newspaper, if you think about television, there's nobody else with this strategy in local media, that's, that discipline not going into the top 50 markets. So that is a, I'd say, important reason to our success. The second reason is because we've had this digital success and this digital growth consistently year over year. It's allowed us to invest in local content and the fact that I can hire a DJ and they're going to do a great on-air show that's going to be hyper-local. But they're also creating content for all of our digital platforms. We call them the original social influencers, 360 degree content creators. So, when they're posting articles to our websites, we're obviously able to draw a big audience.


So, I just shared with your listeners that through our AM FM broadcast, we reach one in two adults. Through our local websites, we reach 70, seven zero of the adult population, so even more than our AM FM broadcast. And that's because we are creating credible, original, entertaining, and informing local content for our website. So, I want to encourage your listeners to go to any one of our websites to see that. So, with that business model, it would be very hard for a local broadcaster and nobody in the industry has the digital percentage of revenue we have. We're over 50% and no one's close to that. So, it has afforded us to continue to invest in local content where others don't have the wherewithal to do that because they don't have this digital growth engine to be able to do that. And I think that's a fundamental strategic competitive advantage for Townsquare and I think that only continues to widen as we look forward over the next three to five years.

Jonathan Boyar 16:41

So, I know you're trying to at least from the stock market narrative, pivot away from being a radio station, but it's still a good business and it helps obviously grow the digital footprint. So, you have 370 radio stations or so across the country. Correct? Yes, how many out there besides those that you own? Like, how big can you get in terms of radio, because it seems like it's the return on investment would be fantastic.

Bill Wilson 17:08

You're exactly right and listen, we're not trying to pivot away from radio. We just don't want to be perceived as a radio only company and, as your piece in March noted, our multiple is actually less than other public radio companies at a six times multiple. So, we're not pivoting away from it. We embrace it, we love radio. We wouldn't be where we are without it. But we are not a radio company. We're a digital first local media company and therefore we think we should be valued on a multiple of traditional radio at six times and digital businesses at 10 to 12 to 14 times. So that's really the story we're trying to continue to gain understanding of. But, going back to your question, there's so many regional smaller players, mom and pops there's hundreds to be able to be acquired, if not over a thousand.


We actually recently did an acquisition, Jonathan, a small-scale company called Cherry Creek, coming up on two years ago, so it was June of 2022. And we bought that at call it, five and a half times, six times multiple, but they had no digital business. So, when we look at acquisitions, we look at leading market share. So, we want stations and brands that are in the top five, beloved by the community, with great local leadership, great sales teams, so they had their ingrained in that community and, obviously, markets outside the top 50.


But we knew when we bought Cherry Creek that we'd be buying it let's just call it a six times multiple and that within five years that would be the two to three times multiple because of the growth in digital and I actually was just doing our first quarter financial review yesterday and the growth in Cherry Creek in the last two years has been exactly as we expected. So, there is a lot of opportunity for acquisition and taking what I would call traditional radio companies and building digital businesses alongside them, which is how Townsquare has done it for 14 years. And there's also the opportunity for organic growth. Even without acquisitions, we expect to be a high single-digit revenue growth driver and mid-single-digit profit driver over the next five years. Acquisitions would just be on top of that.

Jonathan Boyar 19:12

Does the government prohibit you from growing to a certain percent, or are you free to keep on buying radio stations?

Bill Wilson 19:19

Yeah, so I was actually the executive chair of the National Association of Broadcasting. On the radio side they represent radio and TV, an amazing organization led by Curtis Legette. I just came back from the conference in Vegas, second largest conference outside of CES out there, and unfortunately my views are the FCC is antiquated in their rules. The quadrennial rule 20 years ago has a cap where we're restricted from owning more than four FMs and two AMs in any of our markets. And 20 years ago you didn't have Meta and you didn't have Google and you didn't have you name, your device or your platform. That competes for people's attention and we're limited and I think that's unfair.


I expect at some point those limits will be taken away and it'll be very accretive for us because we can add more distribution, more content, more AM FM signals with really the infrastructure we have already of a sales team and a market president. But we're not limited from going out and acquiring additional markets, we're just limited to having more stations in the market. We are so Cherry Creek we were able to add a number of markets that we didn't have, which is going to shape up quite nicely because we have a good presence in Montana, which is going to be a great political year for us. And then we picked up a station and a market in Sierra Vista, Arizona, which again should be a great political market for us. So, we are limited to how many we can own, but we're not limited to the number of markets we can operate in, so there's plenty of room on the growth side there, 100%.

Jonathan Boyar 20:45

You were talking about not getting the multiple you deserve. One way to do that is by having artificial intelligence in your name. You have been talking a little bit about how you're using AI. Just curious how you're using it in your business today?

Bill Wilson 21:01

Yeah, I couldn't be more excited about artificial intelligence just from a business perspective efficiency, productivity, as well as just being a citizen, and what's going to transpire over the next five years I'm just incredibly fascinated. But we actually, over the last 12 months, have been starting to leverage artificial intelligence for business processes. This gentleman by the name of Sun Sax he actually just won the Digital Leadership Award from the National Association of Broadcasting a couple days ago in Vegas. Sun and I go back over 20 years. He was my head product at AOL and he brought over a team of 15 to 20 people, including Anibal Rosado and Juan Sarri and many others. So, I had the benefit when I joined. It wasn't just myself, it was almost 40 colleagues from AOL at the time, and he is really leveraging a lot of artificial intelligence. So, I'll give you a couple examples.


One would be when we create creative or we create a website. Traditionally we would start from scratch. I would call Boyar Value and say okay, what assets do you have? What can you provide me so I could start to create digital advertising for you, be that a display ad or a video ad or anything else of that nature. He's created some AI that will plug in the name of the business. You plug in the URL of their website and it'll scrape that website. Come back with draft creative. Then the human is involved and they do the extra 10 or 15% on top of that to make it great. Show you, Jonathan, as the client. Here's your creative, you sign off on it. Then they use AI instead of a human to put that across multiple sizes and platforms. Where before it would take somebody, say, an hour to create multiple sizes of a display ad, we now use AI to do that. So obviously an amazing, efficient way to save time and energy and put that time and energy into other returns on those people's times.


The other thing we're doing is Townsquare Interactive. We're using AI to listen to all the clients who call in, as well as all of the outbound sales calls we do, and we used to have a manager sit there and listen or transcribe and get some key takeaways from calls. Now we're using AI to go okay, if a client is upgrading, what are the things they're upgrading for? If someone's looking to downgrade or if they have a problem with their service, what are those commonalities? When a sale pitch goes well and closes, what are those commonalities? We're using AI for all of that, where before it would literally be hundreds of hours of listening to calls. So those are just two examples of maybe 10 or 15 today that we're using. So, when I think about the next two, three, four years, I think it's going to have a profound impact on our business. But, quite honestly, I think it's going to have a profound impact on everybody's business.

Jonathan Boyar 23:34

Okay, Townsquare AI. You get an AI multiple. The stock will rip. I hope you've been enjoying the interview. To read Boyar Research's report on Townsquare, please visit And now back to the show you had mentioned Townsquare Interactive. Can you briefly explain what that business is?

Bill Wilson 23:56

Sure. So, we have two significant digital businesses. One is Townsquare Interactive and one is Townsquare Ignite. Townsquare Ignite is advertising and Townsquare Interactive is digital marketing solution. So, I'll talk about Townsquare Interactive.


It was interesting, Jonathan, coming from AOL and New York City and big city media One of the things when I started at Townsquare that Stephen Price and Stu Rosenthal. They were very dedicated to go to every market back then it was 35, grew to 50, today 74, but literally go to every market every year. I joined this chief content and digital officer back in 2010, and I would join them on these trips and as we started to transform our digital websites. When I joined the company, we had no digital websites. We created digital websites. We created this audience that I told you earlier reaches 70% of the adult population.


In one of our town halls, we'd always go in and we'd give an update on the company, but really the benefit to us was hearing what was going well, but also the challenges and how we could do better for our clients, our community. What could we do better at corporate to help and empower the teams? So, it was a two-hour town hall, open questions and an account executive in St Cloud, Minnesota it's about 90 minutes outside of Minneapolis raised her hand and said we've done such a great job for our own brands and created tremendous value on our websites. Why aren't we doing that for our clients? And I'm like, well, tell me more, because I'm coming from New York. I'm thinking everybody's got a website and they're good to go. And long story short, after hearing her and then doing market research in five of our markets, we realized there was a significant opportunity to provide digital marketing solutions. So, building websites, helping people with search engine optimization, doing social media, helping them set up their profile on LinkedIn anything you would think of for a business. So, we started that business organically in the markets we were in back then when we were in less than 50 markets. This is in 2013, roughly that business, in essence, over the past decade has added almost 10 million top line once it got it started and 3 million bottom line every year. So, I think last year was over 80 million in revenue at roughly a high 20% margin.


After a few years of only being in our markets, Jonathan, we realized I wouldn't call it by mistake but there was a seller in our Fort Collins market in Colorado, which is about an hour outside of Denver, who started selling the same product and solution to small SMBs. Our target was businesses with less than 20 employees, less than 5 million in revenue, so pretty small businesses. And they were going home one day or on a trip to Colorado Springs, which isn't a market we had radio stations in, and they say, hey, I see there's a need here for the same thing. Can I sell it? I'm like, of course. So, then all of a sudden, we started testing a call center in Charlotte and started calling into like-sized markets so again, markets outside the top 50 and offering the same service. And today 70% of our Townsquare Interactive clients are outside of our radio footprint and roughly 30 are inside. And it's a monthly subscription business. So as a small business owner, you're giving us your credit card. On average, we're charging you about $300 a month and it's a recurring revenue stream and that's almost 20% of the company's revenue and profits today. And we see significant, significant opportunity over the next 10 years to continue to grow that business and grow that first over $100 million, then over $200 million, and then keep going. We have a great slide in our investor deck that talks about there's 9 million target customers here with a $32 billion TAM opportunity, so a lot of runway for us.


We did take a step back last year. First time ever, we lost some subscribers and that was really two things that happened Self-inflicted wound of having a return-to-work mandate, because coming out of COVID Charlotte was our largest office with over 500 employees and they all were working remotely for a couple of years. And in 2022, we had a return to work decision that if you were either a new employee or not, a tenured high performer, you needed to come back at least hybridly, and we lost more people in 24 months in that division than we had lost in the first nine years and that created a lot of turmoil with our customer base and our client base. And then, obviously in 2023, there was significant inflation wage pressures on these small businesses. So last year we took a step back in that business and, as I said recently on our earnings call in March, my expectation is we return to a subscriber growth in Q2 of this year.


As I said recently on our earnings call in March, my expectation is we return to a subscriber growth in Q2 of this year and then, after subscriber growth, you'll also start to see month-over-month revenue growth and I expect that in Q2 this year and that'll be followed by month-over-month profit growth Really depends on how quickly we're investing. Given what we're seeing now, we're investing quite heavily in the business. We opened the second location in Phoenix last year and, given the runway and our current metrics, we're investing quite heavily. So, profit will return month over month growth either in Q3 or Q4, depending on how much we can invest right now.

Jonathan Boyar 28:45

So, you had a bunch of employees who essentially quit when you told them they had to actually step foot in an office, and that made customer service deteriorate and some of these subscribers left. Is that basically what happened?

Bill Wilson 28:58

Yes, exactly that's exactly what happened and, to be honest with you, obviously it was a somewhat unexpected in terms of the magnitude of that. Truthfully, I believe it made us a stronger company. We got knocked out let's call it what it was. Literally every quarter for many, many years we were adding roughly 800 net subscribers, sometimes 1,000, but very, very consistent. All of a sudden last year we lost, I call it 7,000 subscribers. We cut that Q4 to Q1. We told people we'd cut that in half, we'd be under 800 losses in Q1 and return to growth in Q2, as I just said.


But we took it on the chin. So, we said, okay, let's take this opportunity and really attack ourselves. We built a company from zero to $90 million with a call it a 30% profit margin. What would we do differently to take a company from 90 million in revenue to make it 250 million in revenue? And so, one big change we did is we used to have a one-to-one customer service model.


So, Jonathan, if you called in, you would get Johnny and Johnny's manager would be Susie, and so obviously, when Johnny left, that was very disruptive for you. You start talking to Johnny. He was your marketing consultant. So, we decided to go to a pooled model where when you call in today you may not get Johnny, you're going to get somebody who knows your business, knows why you called before and handle whatever your questions or your needs are, and to your question earlier, we're starting to use artificial intelligence on those calls as well.


I think that's a much more efficient model. Our answer rates have gone up almost 100% because before, if you called in and you were talking to Johnny, Johnny used to handle 200 businesses. When I called in as another client, I may go to voicemail because Johnny's on the phone. So, this is a much more efficient in terms of how to scale and, I think, a better customer service model for our subscribers. So, there were many things like that. We don't have enough time to go through them all in this podcast, but I am incredibly confident. Townsquare Interactive is a stronger company today because of the setback we faced last year.

Jonathan Boyar 31:01

In terms of the Townsquare Interactive piece of your business. I mean you said now a large percentage of it is not in your traditional radio markets. How do you leverage having the radio stations in those markets, like, how do they go together?

Bill Wilson 31:16

So, in the 70% of the clients who are outside the market has nothing to do with radio. There's no overlap. In the 30% where we are selling Townsquare Interactive. We're utilizing our existing sales teams to provide referrals to our Townsquare Interactive team. So, I think, going back to one of your questions like why are you performing so much better just radio to radio companies? Putting aside the success you've had in growing a very profitable digital business, part of it is we have full funnel marketing solutions. So, meaning clients don't want to deal with multiple vendors.


Well, Gordon Burrell has done a number of studies where 10 years ago, a small business would work with, quite honestly, 10 different providers, be it the yellow pages, the newspaper, television, radio, outdoor company. Today they want to work with one or two providers who could really handle their advertising and marketing needs. So, you want to be really one of one and the only way to do that is to have full funnel solutions. So, the fact that we've got radio, which is the best cost-effective reach medium, but then we've got this programmatic digital business, and then we could also help you with your website. Build your website, make sure you're on the front page of Google for the appropriate search terms. That is highly differentiated and a competitive advantage. So, going back to your question, in the 30% of the sales where they're coming from our markets it's part of the same pitch that we're pitching advertising, so it is one ecosystem in those markets.

Jonathan Boyar 32:38

Yeah, but Wall Street hasn't been as kind to you as it should be, at least in our opinion. In terms of the valuation, it seemed like the Timesquare Interactive would get a higher multiple. Have you ever considered spinning out that portion? Would that make sense?

Bill Wilson 32:51

We get a lot of questions about that. Is that a possibility one day? It could be, but the characteristics of helping the radio division and that overlap is powerful. So, could that happen? Yes, because they could obviously be an arm's length relationship. But my view is we are going to get that value, particularly as we today call it 50% of our revenue, 55% of our profits coming from digital. Fast forward, just two or three years, I expect that to be over 60% and then think five years, I expect that to be 70% revenue of digital and 70% digital profit.


So, we're extremely patient I mean just like you are, as investors, like I read a lot of your materials. We have the same approach where, as long as we stay disciplined, consistent, I think we have a culture of high performance and accountability. We're not worried how we're valued today. We're trying to unlock value. We're de-levering. We get the advantage of our stock price being so undervalued. We're able to retire millions and millions of shares at what we think is a ridiculously slow price.


I think part of the story, Jonathan, is A: we're lumped in with radio traditionally and I think we're starting to break out of that box Two: we've been highly levered. We stated for a little while that we were going to come down from six times. We stayed above six times for quite some time. We've got our lowest net leverage, in essence, in quite a while at 4.4 times. We expect that over the next 18 to 24 months to come down to three times. So, I expect that to be a material difference in the eyes of investors. As you know, we just initiated a dividend a year ago. We increased that dividend by 5% in March on our year-end call. It's now, I think it's about a 6.5% yield.


You talked about pivoting from the radio business before. What I think we're doing is pivoting to really putting a spotlight on our cash flow generation. We continue to do amazing in terms of growing our cash flow from operations, to do amazing in terms of growing our cashflow from operations and by initiating the dividend based on the investor meetings I've had that new investors who discovered the company. I think it's clear that was a great, almost a marketing strategy on its own to get people to recognize the company. So, we're just going to stay disciplined. We're going to continue to de-lever, we're going to continue to grow our overall profits and the mix is going to be more and more digital revenue, more and more digital profits and, to your point, the intrinsic value I think in your piece was called $25. We think not only are we going to get there, our aspirations are much higher, as long as we continue to execute and grow the overall business.

Jonathan Boyar 35:17

I mean you've done a fantastic job in terms of capital allocation, and I think it helps that you personally own a lot of the company because you have skin in the game. I mean, I think, at least in our calculation, you've purchased about 60% of shares and warrants outstanding. You know an average price of a little over $7. Its share price now is 12, which is great, assuming the shares are undervalued. But does the leverage keep you up at night in an uncertain world?

Bill Wilson 35:47

Not at all, because I mean, just think about our cash flow generation. Obviously, if we were concerned at all about that, we wouldn't be buying back as aggressively as the share. We'd just be hoarding the cash, and you noted this in your piece. If you just look at the free cash flow yield and you look at the free cashflow versus the market cap, and I don't know if that's three or just incredibly undervalued we talked about multiples before of EBITDA. I would encourage people just look at our free cashflow.


You've noted in your piece the three-year average. In that it's consistent. It's not like one year was great and a couple of years were subpar. Each and every year, even after last year, which I would call a subpar year for the company overall because of the step back in subscribers at Townsquare Interactive, we still had a great year second highest revenue, second highest profit in the company's history. So, going back to your question, not at all, I think. As I moved into this role putting aside COVID in 2019, I became the sole CEO when, I think, we were about over six times levered and we've marched that down to about 4.4. And we said we were going to do that. We're going to continue to do that I think, as I said earlier, we'll get that under four and closer to three over the next two years.

Jonathan Boyar 36:49

Do you like being CEO of a public company?

Bill Wilson 36:53

I like being CEO. I'm blessed. I have an incredible family. This is a dream come true for me in terms of the job and the people I work with, the culture we built. I'm incredibly proud of the Townsquare team. I feel it's an honor to represent the team. They're obviously doing all the work. The corporate office is extremely small. We're talking about even with the accounting team, we're talking about less than 50 people. So, with over 2,200 employees, the people doing the work are all in the markets, serving their communities and their clients, and to me, that's what Townsquare is about. It's like how do we serve these tremendously underserved communities, how do we help these clients? And that's what we're really, really proud of helping these business owners reach their dreams.


So, I love being the CEO of Townsquare. I look forward to doing this for as long as the board will have me. The board couldn't be more supportive, as a first-time CEO has given me tremendous advice. They have long-term vision. I can't say enough about the Townsquare board, but obviously, being a public company, you spend a lot of time on things that maybe aren't the most effective. It's just sometimes there's things you got to do that are a waste of time. Thankfully, I have an amazing corporate team, our COO, Eric Hellum, a tremendous business partner. He actually started in the radio industry, so it's been a great combination of somebody like myself with the digital background. He started decades ago and been in the radio industry the whole time, and we wouldn't be where we are without Eric Hellum. So, I love being the CEO of Townsquare. I could see us being private or public and being just as happy.

Jonathan Boyar 38:19

Would you be doing anything different if you were a private company now?

Bill Wilson 38:23

Nothing in terms of strategic decisions or decisions. So, I'm sure everybody says this, but, as I said, going back to the board, they have impressed on me from day one. As we plan, say, 2025, we're thinking about what's the right thing for 2030. And that should be factored into your plan for 2025. So, we're never making short-term decisions for the next quarter or, quite honestly, even the next 12 months.


If that was the case, Jonathan, we would have actually stopped our investment in Townsquare Interactive last year while we had an off year and said, okay, let's take a step back, let's make sure we've got this right. They were like if you're confident, continue to invest. We continue to hire throughout this significant downturn where our revenue is down 15% in Q4 for Townsquare Interactive. So no, being a public company, we're not making decisions that are different than if we were private. It's just there's a lot of auditing and a lot of the stuff around SOX compliance and things we have to do. That we wouldn't necessarily do, we definitely wouldn't do, if we were a private company. They just added personnel for SOX compliance that we wouldn't have. They just added personnel for SOX compliance that we wouldn't have.

Jonathan Boyar 39:25

Would it shock you one day if you were part of another company or if the company was private?

Bill Wilson 39:29

Not at all. I think about it one of two ways. As you said, a lot of my compensation personally has been part of stock-based compensation. When I joined in 2010. In essence, Stephen Price said I can't pay you what you make at AOL. My salary back then was public because I was an officer of AOL as a public company, so I took about a 50% cash comp step back and my wife was a big part of that decision, obviously because we had a family and I got that in stock-based comp before I was CEO. And then now about third to 40% of my compensation is stock-based versus cash and a lot of that is performance-based, meaning I earn the RSUs only if there's different hurdles hit in terms of shareholder value.


So, I think, all in, if you look at unvested and invested, I probably have a million shares in the company. So, it's significant to your point of making sure the business is run right and that's why we're going to make long-term decisions and never short-term decisions. But I think one of two things is going to happen. Let's say, five years from now, just to pick a number, Our stock is either going to be significantly higher not only what you said at 25, but significantly higher above that in five years, or we'll have the wherewithal to go private. That's the way I look at things. If we were sitting here in three, four years at the same stock price, given our cashflow generation and our ability to in essence, de-lever, we could take the company private.

Jonathan Boyar 40:45

So, I just wanted to talk a little bit about digital advertising and the Ignite piece part of the business. It's a little bit harder for people to, I guess, understand. You gave us a fantastic demonstration, I think, probably two years ago, of the power behind that. Can you explain what it is for people who might not be as digital savvy?

Bill Wilson 41:08

Yes, thank you, Jonathan, for asking so for your listeners. We have a division in the company called Townsquare Ignite. So, we talked earlier about Interactive, which was the subscription business for a website building and SEO and things like that. Ignite is our digital advertising business and within that there's really two components. There's monetizing the significant scale of audience we have on our property. So, we have over 300 websites, over 300 mobile apps and there's a significant size at scale audience there. We collect first party data on that audience. So, in a world where cookies go away, it's highly valuable.

Jonathan Boyar 41:41

What’s first party data just for those who don't understand?

Bill Wilson 41:42

So, first party data would be getting information when they come to your website about their interests. So, are they reading a personal finance article? Are they reading an article about real estate? Are they reading an article about nutrition or medical? And knowing that about an individual, you can get that data on the open marketplace from third parties and you pay an effective CPM for that data. But, as I said earlier, we reach 70% of the adult population, so I believe nobody has as much data on the people in our 74 markets than Townsquare has.


So that's a very, very significant competitive advantage in the digital advertising landscape. So that's one component of Townsquare Ignite. The other component of Townsquare Ignite is programmatic advertising, so we're able to buy inventory across the internet. We are integrated with all of the major exchanges. If you're familiar with Trade Desk, Simplify, Zander, Madhive, there's literally dozens and dozens of companies that aggregate inventory across any connected device. So not just a traditional PC or laptop, but you're watching your Samsung TV and you're watching Netflix, now added advertising, Hulu, Disney Channel. If you're watching ESPN, all of these are now being served advertising through a connected device.


One of the fastest growing parts of the company is serving programmatic digital advertising highly targeted. So, as Jonathan, you described a couple of years ago when we met in your office, you're like you know, I think I understand this. Can you demonstrate this for me? So, we actually, with Jonathan and his team, walked through a presentation where he was a small business in one of our markets and we gave him a pitch and I think all the light bulbs went off, which is great. So, you tell me you're a business, say you're an HVAC company in Tyler, Texas.


Who is your ideal customer? What's their household income? Where do they live? What are their interests?


I then go find those customers. First, I create the advertising for you. I A B test that to make sure the creative is the best that can be continually optimizing that creative. And then I serve that ad to the right individual, the right individual being that target demographic you described. And then I optimize where that ad shows up. Should it show up on a Hulu show? Should it show up on a Disney show? Should it show up on the Weather Channel?


And we see which one performs best. And performs best is really defined by the client. What is their key performance indicator? Are they looking for awareness? Are they looking for a form fill. Are they looking to convert to a paying subscriber for e-commerce?


It's incredibly powerful and when you think about what we've been talking about, Jonathan, where Townsquare is focused on markets outside the top 50, my belief is no one can do this better than we can, and we're quite pleased with the growth where we are.


It's the fastest growing part of the company in terms of revenue and profit for the last five years. But when we think about the next decade, you think about 69% of all advertising today in the United States, local advertising is digital advertising. That is expected to grow almost to 80%. In the United States, local advertising is digital advertising that is expected to grow almost to 80% in the next five years. So, we've got this tailwind behind our back of growth in digital advertising. We believe we're highly differentiated in that space and then, even if it wasn't growing as much as it is, based on our data from Gordon Burrell and Associates today, in 2023, we captured less than 15% of the addressable digital market in our markets. So, there's so much more share shift that can happen and then you have share shift plus the benefit of a growing market, and that's why we're as excited as we are about Townsquare. Ignite our digital advertising arm.

Jonathan Boyar 45:18

Is there a big overlap between the customers of Townsquare Ignite and Townsquare Interactive?

Bill Wilson 45:23

Very little overlap. I think part of the reason is our Ignite customers. There is some overlap, but I'd say less than 20%, because the Ignite customers are usually much larger in scale, have a lot more money to spend than the smaller customers that we're focused on for Townsquare Interactive. So incredible opportunity with Townsquare Ignite and it's performed extremely well year in and year out and we're excited for the next five to 10 years in that space.

Jonathan Boyar 45:47

Your competitive advantage, I guess on Ignite and please correct me if I'm wrong is you have all these websites that you created in those smaller towns and you're able to target people in small communities, and that's why someone would want to use your marketing agency. Is that?

Bill Wilson 46:06

That's one component of it. The other component is A we've got all this first party data. Two we have a team there's roughly a hundred people who buy media, optimize media. The creative is a big part of this in terms of the messaging and the visuals we're doing now. In essence, we're doing television advertising for clients. We weren't able to do that five years ago because we didn't own television stations, but now, with cord cutting and as much inventory with streaming television, we're in essence competing with cable television and network television. So part of the differentiation there is we've got this huge scale of hundreds, if not sometimes thousands, of campaigns for lawyers, doctors, plastic surgeons, hvac you name a vertical and quite honestly, I could sit down with you we're doing this in the home improvement space and particularly HVAC, and I could sit down with you and say we've done this campaign for over 500 customers across the US that look just like you. This is what they did prior to working with Townsquare and this is what they're doing today. So having that scale and that expertise in verticals is highly differentiated. Again, particularly in markets outside the top 50.


In addition, we're often competing with local agencies. There's a digital agency in every one of our 74 markets they're utilizing usually free exchanges. They go on Facebook. My son buys ads on Facebook. There's no barrier to entry. You could buy display advertising through Google there's no barrier to entry.


But we're sitting at exchanges that have six or seven figure minimums per month in spend. So, a local agency wouldn't be able to do that necessarily in Tyler Texas. But because we're bringing this, I call it national sophistication to small town America, it gives us outside differentiation in terms of purchasing power for inventory, as well as just the ability to see the amount of inventory we can. And that may matter less in New York, but when you're in Tyler Texas with 300,000 people and you want to reach somebody with a household income of 75,000 who has two kids, drives a Honda Odyssey and loves MMA, there's only so many opportunities you have to do that. So, the more inventory you have to not only reach that person but to optimize that creative, make sure that you're reaching them on the right platform. We take great pride in that, and we live and die by the results we provide our clients. So, I view that as highly differentiated for Townsquare versus others that we're competing with in our size markets.

Jonathan Boyar 48:33

Bill, I want to thank you for your time. It's been fantastic learning about your career, working with Clive Davis to AOL to then going to Townsquare, where you took kind of a big risk in terms of a pay cut to try and build something great. I look forward to monitoring your progress and following Townsquare, and I think the best days are still ahead.

Bill Wilson 48:55

I agree, Jonathan. Thank you so much. It's been an honor, it's been a pleasure and I look forward for all your listeners, hopefully to learn more about Townsquare, spend some more time understanding the company, and if anybody has any questions, they could always reach out to me at any time. My email address is, and thank you again, Jonathan.

Jonathan Boyar 49:11

Thank you. I hope you enjoyed the show. To be sure you never miss another World According to Boyar episode, please follow us on Twitter @boyarvalue.Until next time.



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