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Scott Kaplan Decided He Was All In

“I will tell you right now we were going in. We were on the goal line and going in. We were that close.”

Brian Noe

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The late Dennis Green, an NFL head coach for the Minnesota Vikings and Arizona Cardinals, had a great philosophy. Green said the following on NFL Network’s America’s Game that chronicled the 1998 Vikings: “Desire, dedication, and determination are the three D’s and they’re really for me the essence of life. Desire is establishing what you want; what do you want? Dedication is the price that you pay to get it. Determination is how many times can we be disappointed and still not lose the fire in our belly?”

Scott Kaplan definitely hasn’t lost his fire in spite of dealing with a lot of adversity. 

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Kaplan is a sports radio host that has carved out a very impressive 18-year run in San Diego. His level of determination has been greatly tested as his former radio home, the Mighty 1090, went off the air four months ago in April. It was never in Kaplan’s DNA to shrug his shoulders and say “well shucks” as he passively accepted a falling out between a radio company and the owners of a transmitter site. Kaplan went into fix-it mode and hasn’t looked back since.

The story of Scott Kaplan has many different layers. His view of the 1090 soap opera is fascinating as Kaplan details just how close the station was to being revived — we’re talking Seahawks on the goal line in the Super Bowl against the Patriots here. Yep, that close. Kaplan is an extraordinary example of how hosts should look at traditional radio in non-traditional ways. Using multiple platforms to distribute content to the public instead of solely relying on a terrestrial radio station makes a lot of sense. Kaplan believes that shows need to go to the people, not expect the people to come to you.

His ambition is admirable. His determination is unwavering. And his viewpoints are incredibly useful. Enjoy.

Brian Noe: What have the past few months been like since the Mighty 1090 went off the air?

Scott Kaplan: You know what, it’s been an amazing learning experience. It really has been. Listening to how this radio station crumbled. Understanding why it was. When you look at things like excessive executive salaries, a massive amount of office space that was wasted and hyper expensive, and a really bad deal that this radio company was in with the owners of the transmitter in Mexico. It was just not a financially sustainable model in any way.

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Unless you had a billionaire investor who just liked throwing money at it — which at one point this company had and it no longer did — there really was no oversight of management. It got to a point where they just couldn’t pay for the transmitter any longer and the transmitter owners took them off the air. Man, what a hard thing to learn when you’re an on-air talent and your ratings say that you’re the top in the business. Then you find out well we’re doing our job, but the other side of the building didn’t do its job. It’s been an amazing learning experience. It really has.

Noe: Has this been an angering process for you?

Scott: I’ve never been angry about all of this because really I look at myself and I think, I knew that I did not want my career to be in the hands of the management of 1090. I knew that for many years. I never really wanted to sit around and wait for these guys because I never believed in their leadership. I wasn’t angry. I just immediately went into fix-it mode.

For me, trying to fix the problem was let’s work a deal directly between me and the guys who owned the transmitter. I’ve got all of my winning teammates around me. I’ve got our morning show. I’ve got our midday show. The morning show took a job quickly across town and then in the last hours as I was trying to finish this deal off my colleague, Darren Smith, took a job with another radio station in San Diego.

Even though the lineup wasn’t going to be the same I still thought we could rebuild a winning brand. But ultimately the numbers don’t lie. Some guys in sports radio really love the statistical side of sports. I’m not really a fan of numbers unless I’m handicapping horse races.

I had to do a lot of learning about spreadsheets and real dollars and cents. Things that as a talk show host you don’t really learn about, you don’t really talk about all that often. But now we’re talking about big money and I needed to decide could we really make money? When the numbers got to the very end, the people who own the transmitter, they make a really nice amount of money. The people who work at the station, they all get paid. The company loses massive amounts of money and the investors don’t make back their money or profit. It’s just not a winning proposition.

This is stuff that I did not know and had to learn and then had to be unemotional about. As much as I wanted to employ all the people that worked at our station, as much as I wanted to rebuild this brand, and as much as I want to get back on the air not just in San Diego but all of Southern California, I couldn’t let the black and white numbers take over my emotions and do a deal that was going to be bad for everybody involved. Like I said, this has been a phenomenal business learning experience.

Noe: You mention Darren Smith and some of your other former co-workers. What was your reaction when your teammates joined other teams?

Scott: The first group of guys who went to the Padres home radio station, I wish they would have given us a little bit of time, but I understood their position. It was fine. They were a one-year show at our station. We were helping to cultivate them. So I kind of understood. They had the energy of a fresh, brand new show.

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With Darren Smith, Darren gave me a lot of time. He told me his goals were to get on the air by August 1st. He told me his goals and I knew what they were, but I wasn’t working for Darren. I wasn’t trying to meet his goals. I was trying to get us all back on the air as quickly as possible. Doing a good deal takes time is what I learned. This unfortunately took more time and didn’t turn into a good deal.

I wasn’t disappointed. I was happy for everybody. I’m happy for Darren Smith. He has what he wanted; he likes security. I’m happy for our morning guys because they have what they wanted, which is to be around the baseball team. You can never be upset and unhappy for other people’s success. I’m very happy for all of those guys.

Noe: As far as not trusting management at 1090, when things crumbled did you reflect back upon the situation relating to yourself? Were you like, man, I knew better than to be in business together?

Scott: I knew that 1090 was in financial trouble. I also knew who the leadership was and I didn’t have any faith in them. I also knew that everybody else in the place had no faith in them either. But people are scared and people don’t want to have a revolt if you will. If the parent company would have had any oversight over this management team, they would have attempted to fix this a long time ago. But they didn’t. The parent company took their hands off of it and said forget it, survive on your own is essentially what happened. The management of this company couldn’t survive on its own.

If you looked at why that was, I can show you a million reasons — literally in dollars a million reasons — why that was. I was not mad at management. I knew in my own heart that this was not a team on the management side that had great leadership. We believed on the programming side we had tremendous leadership. We were insanely successful for a really long time. We felt like we were doing a very good job on our side of the building, not necessarily complimented from the other side of the building. And by the way if you know the characters involved you’re not really surprised.

Noe: What was that like for you on a day-to-day basis?

Scott: It was not a fun work environment. Not fun. Darren Smith and I would do this crossover every day where we’d spend 20 minutes on the air together. We’d probably spend 30 seconds before we even got on the air together, and we’d talk very openly and raw. It was not a place that people were having fun being there. It just filtered all the way down.

Management got rid of people whose jobs were important to the success of the radio station. Those folks were sacrificed so management could keep their jobs and their salaries. These are crazy realities that we don’t necessarily all encounter. Look, everybody’s got stories in the media business, but this was just one where I didn’t know a lot of what was going on and felt frankly a bit naive, but again I learned a ton along the way. It was not a great work environment. I can tell you that certainly at the very end.

I mean can you imagine? You have a guy who’s the president of the company who tells everybody we’re being pulled off the airwaves. Then for the next 20 days we’re broadcasting on our app — still by the way dominating in the ratings without even being on the air frankly — and at no time is there communication between the person steering the ship and the people who are out of control in the back of the ship who have no idea what’s going on. Zero communication. Zero leadership.

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Noe: That’s wild, man. You have a great resume, but not being a featured part of a radio station has to be a weird feeling, right? Do your past accomplishments make your current situation tougher?

Scott: The thing is you could sit on the sidelines or you can do something. What I did is I immediately sprung into action. Rather than sit around and not be heard, I was able to immediately work a deal with Callaway Golf to use their studios. I’ve been broadcasting on YouTube, on Twitter, on Facebook Live, on the TuneIn app, and I’ve been in communication with my audience through all social platforms. I have sponsors that have wanted to stay with me because I’ve spoken for them for many, many years. I have an incredibly loyal group of producers and teammates who want to keep the show alive.

I’ve said this all along; desperation has spurred innovation. We’re actually in the process right now of building a studio in my house where I can do all of these different things that I want to do. All of the things that I was planning on doing with the 1090 transmitter I still think I can do, only now rather than using a transmitter I can use an app as more of my central location.

As of right now, you say well you’re not a part of a radio station. That’s true. But my fulfillment comes from broadcasting and entertaining. I get that fulfillment every day I go on using these other platforms. By the way if you look at my YouTube show, I get calls from people all over the radio industry saying you’re show looks as good as what Dan Patrick has. It looks as good as Colin Cowherd. It looks better than Jim Rome.

The studio at Callaway is awesome and when they turn on the lights and the cameras, you’re broadcasting on all these platforms. For people that are savvy enough to Bluetooth an app from their phone into their car, for those folks who are already listening on an app, not even using the AM transmitter, there has been virtually no interruption for those people. In fact if anything the show is probably better because we don’t do any commercials.

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Noe: Has it been more rewarding doing it the way you have than simply having a typical radio shift on a typical station?

Scott: No, it has not been more rewarding because I haven’t been paid in four months. It’s been less rewarding because I’m making a whole lot less money. However, and now I’m being serious, it has brought my team closer together than ever before. We travel together — in other words we all get in a car together — we have a much longer commute than we used to have. So we are literally in the car together for about 60 to 80 minutes a day. We talk to each other differently now. We hang out with each other quite a bit differently now.

Everybody who has decided they want to be all in, they are coming up with their concepts and their ideas. By the way most of these guys are significantly younger than I am, and they all think I’m crazy for even wanting to get back on radio. Me, I love the medium of radio. I loved it when I was a little kid when it used to talk me to sleep. I loved it when I was a caller growing up. I loved it when I was able to work at a radio station and splice tape and feed it down a line. I loved it when I was producing at the Super Bowl as the Super Bowl was turning into what the Super Bowl is. I’ve loved broadcasting on radio for all these years.

Dude, I mean listen I’m an available free agent. If somebody calls me and says hey we want you to come and take this shift on a radio station in a market that I find very desirable with the teams I’d like to cover and a desirable place to live, I am all ears. I have a great team and we have a very successful product. But on the other hand I can’t wait around and wait for a radio station or a radio company to come grab me because I think hey I’ve had this amazing run in Southern California. Rather than wait around, I can continue to broadcast. I can continue to sell and who knows what the future brings?

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I have nothing but great things to say about radio, but my younger producer guys, they all think the future is now with all of these digital platforms. Going out to the people not just in your local market but literally all over the world and communicating to these people with all the social platforms we have at our disposal right now, there’s a whole new world out there for broadcasters.

We’re all sort of making it up as we go along in many instances. That goes for even big networks and big radio companies who are trying to figure out the podcasting side of the business and are trying to figure out where does video play into any of this. It’s a very exciting time. That’s for sure. And by the way probably a very nerve-racking time really in traditional radio.

Noe: Since you’ve operated your show as a digital play on YouTube, TuneIn, and Twitter among others, what has surprised you the most?

Scott: The amount of people that are watching and listening. The willingness of the listener to say you’re the guy who I like listening to on the radio. I can’t get in my car anymore and turn on the radio, but I still have access to your content. I’m blown away by the things that we’re doing now. Why weren’t we doing these things before?

YouTube has an ongoing comment section and I’m following the comments while we’re on the air. I’m interacting with these folks while we’re on the air. Why weren’t we YouTubing when we were broadcasting? Why weren’t we doing simple things like being on Facebook Live? We have thousands of viewers on Facebook Live. Why weren’t we doing that before? Really it fascinates me that people will say to me, listen if I know where you are, then I’ll come listen. I will come watch. I’m blown away by how people watch this stuff on their own time.

I’ve been really spending a lot of my own time plugging my phone into my car and listening to our daily show in podcast form because I really want to understand what is the listener experiencing? What am I asking the listener to do? What I found out is guess what? If I can do it, so can anybody else. It’s really just so simple. You go to the podcast app on your phone and you click in what you want. You turn it on and you’re going. In your dashboard — assuming you have a relatively new car — you see the name and date of the show and I’m listening to it on my own time. I find it absolutely fascinating.

Then on the other hand, I’m following what people are doing on YouTube. I’m watching YouTube videos at other times of the day to understand how other people are ingesting this content because we may only have 500 to 1,000 viewers live, but by the next day there are 3,000 or 5,000 viewers. The content lives on so people go back and watch it at their own leisure. This is all new stuff for me because I had been an AM radio broadcaster.

Noe: For the people on traditional terrestrial radio, how much would you stress to them the importance of putting their content in other places beyond the radio station?

Scott: If it were me and I were going back on to terrestrial radio, which I expect that someday I likely will, but when I go back on terrestrial radio, terrestrial radio will be an additive platform to all these other things that I’m currently doing. We live in a world now — and I hate to be such a philosopher — but I think we live in a place now where you have to go to the people, not expect them to come to you.

Honestly I got into an Uber here in Houston this evening and I asked the gentleman if you could turn the radio from the FM dial where he was playing smooth jazz, to the AM dial so I could hear sports talk. Well guess what? This guy had no idea and he had a brand new car. He had no idea how to go from FM to AM. I walked him through it. He got there — couldn’t figure out how to tune the radio up or down. 

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Look this guy is a professional driver. As a professional driver you should probably know how to use the radio. Millions and millions of people are listening to radio. There’s no doubt about it. But the phone is in your hand all day long. The radio is in your car. The phone is in your hand all day long. This is where I believe ultimately we have to communicate with people.

Noe: What’s been the hardest part of running the show the way you have these past few months?

Scott: Probably me having to be really chill about all the people who work for the show, or who have a role within the show, and their individual level of commitment. People had to put their other stuff in front of the show when the show is not paying them per se. For me that’s kind of a hard thing that we’re not all together every day 100 percent. We can’t all do it. I’m the person who has to do it. My producer, Alex Padilla, he’s kind of the second guy that has to do it to keep the show alive. Everybody else has their things that are going on in their lives that need to take a priority. That’s been kind of hard. We are not all 100 percent as in as we would have normally been. That’s kind of a tough thing.

The other part of it is when you want to put on a good broadcast, you prep. You work hard. You know what you want to talk about. You have ideas formulated and so on. I’ve been spending so much time on the business side and so little time on the content side. What’s fascinating about that is my producer, Alex Padilla, has done such a phenomenal job of handling the content knowing that my mind was elsewhere and that I wasn’t studying the way I should be. He made it super easy for me to just sit down and have enough content that you would not know that I hadn’t watched a game in a month. That’s really one of the most amazing things is the ability for the team to come together and still put on a quality broadcast even with all the mayhem and chaos swirling around.

Noe: You’ve spoken to Entercom recently about a position in Houston. How serious did those conversations get?

Scott: We were very serious. Entercom and I were very serious about 610 here in Houston. It was just a timing issue for me. I was still trying to put together the 1090 deal and they needed an answer. I couldn’t commit. It was that simple really. Their program director at 610 is a guy named Armen Williams. He is probably the sharpest, young program director that I know in the radio business. He’s a disciple of Bruce Gilbert, who is one of the most respected program directors in the industry.

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I was really, really interested in this radio station. They’ve got a great general manager. They’ve got amazing facilities. The talent that they have is really, really impressive. I loved the opportunity that was presented to me at 610. It was just a timing issue.

My being in Houston right now, I happen to be in town meeting with Gow Media. Gow owns a couple of radio properties, but I’m not really here talking as a broadcaster. I’m here talking as a CEO of my startup, which is called Sided. Sided.co is a platform that we built specific for radio, as a parallel ad platform for radio. So I happen to be down here in Houston meeting with Gow Media because I’m a huge fan of what they’ve done with their company and how they utilize radio to move listeners into content online. I’m just so impressed with what they’ve done so we’ve come down here to talk to them about partnering with what we do.

Noe: The other San Diego radio stations [97.3 The Fan and XTRA 1360] — do you view them as potential landing spots?

Scott: Oh, I definitely think that 97.3 and 1360 are both potential landing spots for this reason; if you’re one of those two stations and you’ve thought all along well we’re not going to spend the money and maybe it’s better that he’s off the air and neither of us are using him. When one of those two radio stations decides that they want to be the overwhelming dominant force in sports radio in San Diego, then one of those two radio stations will come and want to hire someone like myself with my 18 years of market equity, all of the advertisers that follow me, and the massive number of listeners that I’ve cultivated relationships with over the years. I definitely would not rule out those two radio stations.

The only issue is that San Diego is not the kind of sports market that big companies want to spend a ton of money on in sports talk radio. It’s not San Francisco. It’s not Chicago. It’s not Boston. It’s not Philly. Obviously it’s not New York.

When you’re in a somewhat smaller sports market with a limited number of pro teams, sometimes big companies are cautious about spending that kind of money on these types of radio stations. But I would argue this, you don’t have to have many pro sports teams. What you need are engaged sports fans. I’ll tell you right now San Diego for all the heat that it takes, San Diego has great sports fans. I know that because for 18 years I covered the teams. I’ve been in the stands with these people. I’ve been at the tailgate parties with these folks. I know that people who live in San Diego are great sports fans regardless of the fact that the Chargers left.

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Noe: If you were in Vegas placing a bet on if 1090 is going to come back, what do you think the odds would be of that happening?

Scott:I’d say today 40-1.

Noe: So you probably wouldn’t put a significant amount of money on that would you?

Scott: No, it’s a long shot. And it’s a long shot because we have two separate sets of economic understanding. My understanding is I see what a radio station sold for in New York City. I see what the folks in Mexico think their radio station or their tower is worth. A radio transmitter in New York City versus a radio transmitter in Baja, California are worlds and universes apart. What they thought their asset was worth versus what I think their asset is worth are two totally different things. Therefore we can’t do business together as of today.

If something were to happen where my colleagues in Mexico decided to change the numbers to where we both would be in a little bit of pain, but maybe we’re both enjoying some pleasure as well, then I would never count 1090 out. I wouldn’t count 1090 out because right now it’s broadcasting a tiny little FM radio station Ultra 104.9 FM from Brownsville, Texas on a powerhouse transmitter in Southern California. As long as they’re not making money with the asset, I wouldn’t count it out. But 40-1, on occasion 40-1 wins. I’ve seen 50-1 win the Kentucky Derby.

Noe: Were the odds of an agreement being reached ever better than 40-1 at any stage?

Scott: Yes, the odds were 2-1 as of two weeks ago. We thought we had a deal in place. Unfortunately I slept on it for like three nights. After sleeping on it for three nights, I realized I’m about to go ask a bunch of investors to put money into something that I’m going to show them is going to lose money for a long time. If I were them why would I want to do this? Why? Because they’re nostalgic about the 1090 brand? Or because they’re my friends and they want to support me?

I didn’t want to become the Alliance of American Football. I didn’t want to hire a bunch of people and think that hey everything is great and then five months later be out of business.

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I would say two weeks ago we were on the goal line and going in. Then I slept on it and slept on it and slept on it, and again back to learning, studied these spreadsheets and understood what the numbers really were telling me. It really wasn’t that hard of a decision to pull back and say this is a bad deal and I don’t want to do it. For me, for the employees, for the investors, I don’t want to do this deal. I respectfully bowed out. I will tell you right now we were going in. We were on the goal line and going in. We were that close.

Noe: I’m sure it got easier once the decision was made, but for those three days where you’re twisting with it — you put in a lot of work and the deal is right there — to not go through with it, what was that like for you?

Scott: Listen I put in a lot of time. I put in a lot of money. I gave up a phenomenal opportunity to go work for a company like Entercom in Houston. My children are asking me questions. Everywhere I go I’m being questioned. I didn’t realize everybody knew who I was. All of a sudden I’m off the air and everybody wants to ask me about it. A lot of time spent. A lot of money spent. All to ultimately find out that this was not a good deal and not a deal I could do.

Instead of looking at it as a failed deal I choose to look at it as the smart move. Sometimes the best deals are the ones that don’t get done. In this case this was one where it wasn’t going to make dollars therefore it did not make sense. It just didn’t. Yes, it was excruciating because I knew that there were people who had put their lives and their careers on hold under the expectation we were getting back on. I fully expected us to be getting back on. One side can’t get rich while the other side goes broke. That’s what was happening.

Noe: Hey man, I get it. That’s understandable. For the longtime fans of 1090, what message would you like to send to them who are left longing for 1090 to come back?

Scott: What’s been amazing about the 1090 listeners is that they didn’t just split in half and some went to one radio station and some went to another radio station. There were three sports radio stations in San Diego. 1090 had like 60 percent of the audience. So you would think the other two radio stations would then all of a sudden pick up 30 percent each. Well it didn’t happen. The 1090 listener has gone to podcasts. They’ve gone to their phone. They’ve gone to music. They’ve gone to whatever it is that’s occupying their time in their car. They are not going to those other two radio stations in droves. They may eventually, but they aren’t yet.

I think that it’s really amazing the brand loyalty that people have. 1090 was part of people’s lives. When the Chargers were terrible, 1090 told everybody they were terrible. When the Chargers became great, they were there to host the parties and drive the bandwagon. When the Padres had playoff teams, 1090 was there to be in the middle of all of that. A generation of people grew up with 1090. And then passed on yet another generation, which is why I’ve got tons of listeners who are 25 years old and guess what those 25-year-old guys have no problem listening on their phone via podcast or YouTube. That’s what they’ve come to know. It was when they were driving to school with their dad or their mom in the car that they were listening to the AM radio.

I just appreciate how loyal everyone was to that brand and when 1090 went away rather than the listener just going over to the big box, big company sports radio station, they just decided I’ll do other things with my time in my car. That’s pretty fascinating to me.

Noe: You’ve also had a steady presence on Westwood One’s NFL games. What’s your current status with them?

Scott: I’ll be back on Monday Night Football this year. What we do with Westwood One is we book a schedule earlier in the year and then we kind of wait for things to move around and change. I’ll be on the opening night of Monday Night Football. I’ll be in Oakland for the Broncos and the Raiders. I was there last year when the Raiders and the Broncos played what we thought was going to be the final game in the Coliseum and it wasn’t. So here we are for the final season and this is the kickoff to the year. I’ve got the West Coast Monday Night Football game. It’ll be on September 9th and then I’ll travel as the year goes on. I’ll be in Dallas in Thanksgiving. I’ll be on the sidelines of playoff games. I will continue my work with Westwood One and hopefully expand my role with Westwood One as well.

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Noe: That, by the way, was the Marshawn Lynch blunt game, was it not?

Scott:It was. That’s right. (Laughs)

Noe: (Laughs) Only Beast Mode, man. What’s one thing that you’d like program directors and radio executives to know about you that they might not be aware of?

Scott: Just because I was on the radio in one place for 18 years and had a lot of autonomy, and just because I have an entrepreneurial spirit, don’t be scared off by that. I will tell you when somebody is the head coach, you follow their lead because they have to do things their way. The one thing about me is I’ve always been a team player. I’ve always been a team guy. When I had to tell the folks at Entercom that I couldn’t take the gig in May, I explained to them that it was because I’m a team guy. I have a team of people around me and they all were looking at me as a leader. I didn’t want to let down my team. 

Ultimately we didn’t get 1090 back on the air, and as much as I thought people were going to be let down by that, instead the feedback from my team has been we appreciate how hard you tried and the risk that you were willing to take.

My point would be hey I’m a team guy. I get it; a lot of people might look at me and go well he’s been in the business a long time and he worked at an independent station for a long time, can he come into a corporate environment and be what we need him to be? If someone has a plan and it’s a plan that they believe is going to work and they say can you execute this plan? My answer is I can do that.

I like to do a lot of things at once. I love being on the radio because those are the three or four hours where the outside world can’t get to me. During the day I just have one of these brains that likes to go in a million different directions and can’t sit still. Being entrepreneurial particularly in the field of media and specifically in the world of radio should never scare anybody off.

In fact I think people should say we need more innovator type people around us. That’s what I would say to people who get a little bit freaked out that this disease that I have called ambition can get in the way of doing great radio. I disagree. I think it’s all part of doing great radio.

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Jason Barrett Podcast – Dave LaGreca

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Evan Roberts, Self-Professed Sports Maniac, Thrives at WFAN

From an early age, Roberts knew that radio was the medium through which he wanted to express his fandom, especially WFAN.

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Evan Roberts made his first appearance on WFAN at just 10 years old, filling in for NBA play-by-play announcer Mike Breen delivering sports updates on Imus in the Morning. The opportunity came after he sent a letter on a whim to the station asking for a job since he enjoyed listening to the station with his father. Desiring to become a radio host was the result of dynamic career aspirations that transitioned from wanting to work as an architect to trying to become the play-by-play announcer for his favorite baseball team, the New York Mets.

“Listening to Mike and Chris, and Benigno in the overnights and Somers – I was like ‘That’s what I want to do’,” Roberts recalled. “….It couldn’t be any more specific when I’m listening to the Fan saying ‘I want to be on the Fan.’ About a decade and a half later, I was able to get it done and I’ve been there ever since.”

From an early age, Roberts knew that radio was the medium through which he wanted to express his fandom, especially WFAN. As a native New Yorker, Roberts connected with the teams in the area and sought the chance to talk about them for a living on a sports radio station with a storied history in the area.

Since 1989, WFAN has been one of the pillars of New York sports coverage and a place that helped pioneer the sports talk radio format. Getting there, though, required that Roberts had deft knowledge of sports, an ability to connect with fans, and experience that ensured he was ready for an opportunity in the number one media market in the world.

While attending school, Roberts was hosting a radio show called Kidsports on WGBB, a radio station based in Freeport, N.Y. serving Nassau County on Long Island. He then moved to Radio AAHS to host What’s Up With Evan Roberts and Nets Slammin’ Planet, the latter with famed high school basketball player Albert King and NBA insider Brandon “Scoop B” Robinson. Aside from being able to refine his hosting skills, Roberts made valuable connections in these roles including one that would help him land his first job out of high school: Danny Turner.

Before he was named the senior vice president of programming operations at XM Satellite Radio in Washington, D.C., Turner served as the engineer for Roberts’ shows on Radio AAHS. He helped to coordinate the technology associated with broadcasting since the shows were done remotely rather than from out of a studio.

“[He] ended up working at XM Radio and heard one of my tapes as it went on and said ‘I remember him. I like him,’ and then sent it to the right person and they ultimately hired me,” said Roberts. “It was my first real, real job working out of high school, and that was about meeting someone earlier on and remembering who that person was and sending as many tapes as I could.”

As a graduate of Lawrence High School, Roberts quickly made the move from Cedarhurst, N.Y. to Washington, D.C. to begin working at XM Satellite Radio, a place he would stay for the next two years. Then, he made the move down I-295 from D.C. to Baltimore, Md. where he worked at 105.7 The Fan WJFK-AM and had to adjust his sports consumption to align with the interests of those listeners. It taught him the importance of research and preparation, important aspects of working in sports media that he still utilizes to this day.

“When I was in Baltimore, I had to be Baltimore,” said Roberts. “I had to understand what makes the Orioles fan tick; what makes the Ravens fan tick. I didn’t grow up as an Orioles fan or a Ravens fan. The Ravens had won the Super Bowl years earlier. I know nothing about winning Super Bowls; I’m a Jets fan.”

At 21 years old, Roberts made the move back to “The Big Apple” when he was hired by WFAN as an overnight host, a role he stayed in for the next two-and-a-half years. Simultaneously, Roberts was working on Maxim Radio doing a night show on the Sirius Satellite Radio channel. Balancing those two roles, while it may have seemed daunting, gave Roberts the chance to broadcast in his home market and talk about the teams he grew up rooting for; the aforementioned Mets and Jets, along with the then-New Jersey Nets and New York Islanders.

Then in 2007, Roberts got his big break when he was named the midday co-host with Joe Benigno on the program Benigno & Roberts in the Midday. Benigno, who got his start on WFAN as a regular caller, had grown a rapport with listeners since joining the station in 1995, making the task for Roberts, a 23-year-old at the time, more difficult in terms of fitting in. Roberts is grateful that Benigno, a host he grew up listening to on WFAN, was accommodating and amicable towards him – plus it helped that they aligned in their rooting interests as Mets and Jets fans.

“He was very welcoming, and he didn’t have to be because I was a lot younger; he had no idea who the hell I was,” said Roberts. “….Right out of the gate, I think he saw my passion [and] my knowledge; he saw a little bit of himself in me, and we were able to bond right away.”

To make a name for himself in the new midday time slot, Roberts stuck to the principles that had been given to him from his early days of radio; that is, to be himself. From the start of his foray into sports media, Roberts and most people around him knew that he was, in his own words, “a sports maniac”, and he needed to maintain that genuine identity on the air. His relatability and passion for the teams as a fan made him an ideal fit for the station synonymous with New York City bearing those iconic call letters and an unbeatable afternoon duo.

“I think as time [went] on and Joe and I developed even more and more chemistry, the audience knew who we were,” said Roberts. “They certainly knew who he was, but they learned ‘Evan’s a die-hard Mets fan. He doesn’t miss a game.’”

While it was important for Roberts to emulate his fandom for the teams he roots for, he quickly developed a cognizance for trying to talk about other teams impartially while on the air. It is a challenge, to a degree, to maintain objectivity daily with intrinsic fandom for certain teams, but being able to understand how other fan bases feel after monumental victories or crushing defeats renders the art of appealing to the listening audience easier. It also upholds WFAN’s commitment to serve as an outlet for all New York sports fans rather than just certain cohorts of them.

“We’re trying to appeal to everybody,” said Roberts. “We want everybody listening. Not just Yankees fans; not just Mets fans; not just die-hard sports fans; not just casual fans. How do you keep every single person wanting to listen to the radio?”

When Roberts first joined the station in 2004, most New York sports teams were rebuilding aside from the Yankees. Today, the preponderance of professional teams in the New York Metropolitan area are contending or at least have the chance to appear in their league’s playoffs, something that is exciting for fans like Roberts but presents a challenge in doing effective sports radio that accurately depicts the emotions of listeners.

“I think what’s going to be a real challenge… is [when] the Mets are in the playoffs, the Yankees are in the playoffs, the Jets look competent, and the Giants look competent, and it’s a Monday,” Roberts expressed. “You’ve got four monstrous fan bases that care about their team. How the hell do you find a way to keep them all entertained?”

To express the true extent of his fandom for niche sectors of the audience, Roberts turns to another form of aural consumption: podcasts. There has been much discussion over the ability of traditional radio and podcasts to coexist in this digital age of media; however, Roberts believes that the two mediums provide a unique combination that was previously nonexistent.

In his opinion, podcasts are a method to delve deeper into topics or teams that do not garner as much time on the radio, specifically those that do not generate as large of a market share or which are not as representative of the interests of the majority of listeners.

“I do a Mets podcast specifically – I called it Rico Brogna because I loved Rico Brogna as a kid and I figured ‘Why the hell not?’”, Roberts said. “…I do an hour breaking down the Mets in a hard-core way that I’m not going to do on WFAN for an hour. I may do it for a couple of minutes. I think those two things work perfectly side-by-side.”

Still, most listeners, according to Roberts, will likely turn to terrestrial radio to get their sports fix, especially if they do not express allegiance to solely one team. 

“The majority of people are still going to turn on WFAN and say ‘Okay, entertain me. I don’t know what I want to hear. You just entertain me’,” said Roberts. “I think those two forms of entertainment can work side-by-side. That’s why we do it.”

When Mike Francesa signed off WFAN in December 2017, the station had to make changes in the afternoon drive-time slot which it did with the debut of Carlin, Maggie & Bart. The show was eventually disbanded though when Francesa ended his retirement just over four months later, returning to afternoons. His return to WFAN did not last long though, departing the station again in December 2019. Again, WFAN had to make a change in afternoons, this time moving Joe Benigno and Evan Roberts to do a 2 to 6:30 p.m. show renamed Joe & Evan.

For Roberts, the opportunity to host in the afternoon slot that he had grown up listening to Mike Francesa and Christopher “Mad Dog” Russo make famous with their program Mike and the Mad Dog was an opportunity he did not hesitate to accept. Yet the change in time also required a change in approach regarding topic selection; after all, since the show would be starting later in the day, it was more important to preview the forthcoming action than recap that of the previous day.

“Even though you’re doing the same thing because you’re the same person, you’ve got to realize the audience is thinking about things a little bit differently; they’re not always analyzing what happened last night,” said Roberts. “I always find that interesting [trying to] balance the two [and] it’s almost like a game.”

When Benigno retired from the station in November 2020, Craig Carton made his return to the New York City airwaves pairing with Roberts to form the new afternoon duo Carton & Roberts. Carton had previously been with the station hosting mornings with Boomer Esiason on Boomer and Carton from 2007 until his arrest in 2017. He served time in prison for fraud-related charges, and ultimately sought and received help for addiction related to gambling.

Since his return to WFAN, Carton has been vocal about his struggle to overcome addiction and the lessons learned from his time serving in prison, hosting a special weekend program titled Hello, My Name Is Craig to discuss these issues in-depth. On Carton and Roberts, the duo has experienced immense success, recently topping ESPN New York 98.7 FM’s The Michael Kay Show in the spring ratings book. From the onset of Carton and Roberts working together though, there was some trepidation as to whether their personalities would blend well together on sports talk radio.

“I remember the first time I was told ‘Hey, there’s a possibility of you and Craig together.’ I was like ‘What?,’” Roberts said. “My first reaction was ‘Really?’”

Now nearly two years in, Roberts enjoys working alongside Carton and learning more about his perspectives and thoughts on the radio industry. Following advice he was given from both Russo and Esiason on working with Carton, Roberts has let him take the lead and discover how the show can effectively inform and entertain its vast listening audience.

“Let’s take a step back; don’t have an ego,” Roberts recalls thinking when he started the new show. “Watch this magician figure out how this show is going to work and then lean into it. I think that’s what I did and it has worked, and I feel very comfortable, I know he feels very comfortable and we’ve got a successful thing going on now.”

Roberts views Carton as an informed talent in the radio industry, aware of the changing nature of the medium and the potential it has to serve its audience. Roberts indeed experienced success in his previous roles, most notably when working in middays with Benigno; however, he is always willing to try new things and form new approaches towards jaded industry practices and show formats.

“I know that I have a guy who I’m working with who knows the medium as well as anybody,” said Roberts. “If he has a vision on how this could work with his personality and my personality, I’m going to listen; I’m going to follow along.”

WFAN and SportsNet New York (SNY), the flagship network for the New York Mets and New York Jets, agreed last year to simulcast Carton and Roberts from 4 to 6 p.m. on weekdays. While the move, which has been made with various other WFAN programs over the years including Mike and the Mad Dog and Boomer and Gio puts the radio program on a visual medium, Roberts’ approach to the show did not change.

The thought always was that he would be doing a radio show with the curtain pulled back, giving longtime listeners the chance to see the two co-hosts during their discussions and on-air interactions.

“They’re listening to the radio, and it’s cool sometimes when you get to peek in and say, ‘Oh, look at Craig’s expressions. Look at Evan’s expressions. Look at the way they’re looking at each other. Boy, they hate each other right now,’” Roberts said. “I think it’s people looking in on a radio show, and that’s what I always try to remind myself. It’s on TV – that’s great – but we’re a radio show first, and I think a lot of people kind of like to eavesdrop on that.”

One of the challenges of doing a radio show whether or not it is simulcast is in taking calls, and various hosts and producers have differing opinions when it comes to their value on the air. Still, while the hosts, producers, and caller themselves may enjoy their interactions, it is fundamental awareness is placed on the audience that does not call in and their enjoyment of listening to a caller.

“I think when you’re talking [to] somebody, you’re not just thinking about the conversation you’re having with them,” said Roberts. “You’re thinking about the 98% of the audience that doesn’t call in and if this is entertaining or not; if this is informative or not; what are they getting out of this?…. I love callers – it’s a big part of WFAN – but as I interact with them… I think the thought that I always try to have is ‘How is everyone else listening feeling about this discussion?’”

While Carton and Roberts continues to do well in afternoon drive among the demographic of men 25-54 years old, the way the ratings are interpreted by each person and entity in radio differs. Something the Nielsen ratings do not take into account is the number of people listening to the show on-demand as a podcast or watching its simulcast on SNY. During his time with Benigno, Roberts scrutinized the numbers, looking at copious and exiguous details, similar to how he consumes professional sports.

The difference is that while it may be good to have a complete understanding of show performance, getting caught in the minutiae of ratings and trying to improve in weaker areas can sometimes be, according to Roberts, a means without an end.

“I think I realized as time went on that’s going to give you a headache and it’s not going to really help anything,” said Roberts. “I think I learned a little more that you still look at numbers but maybe with a broader view of things; not as specific. I look at [them] a lot, but sometimes it’s tough. I don’t think you want to alter a show too much based on what you think is a pattern but may not necessarily be a pattern.”

This fall, both Carton and Roberts will be starting new roles in media while continuing to host their afternoon show. Carton is going to begin hosting a new national morning show on Fox Sports 1 with a co-host yet to be determined, a move that will place him primarily on television in mornings against WFAN and CBS Sports Radio’s simulcast of Boomer & Gio. Roberts will continue to stay on WFAN, adding a new Saturday program with his former co-host Joe Benigno beginning on September 10.

“It’s like getting back on a bicycle,” Roberts said of working with Benigno. “It’s always comfortable…. It’s going to be [like] our old show – just once a week on a Saturday.”

WFAN was the sound of Evan Roberts’ childhood, and a large reason he became as invested in professional sports as he considers himself to be today. Throughout his time at the station, he has worked with various hosts and recently welcomed new program director Spike Eskin to the station. He says the contrast between Eskin and previous program director Mark Chernoff is stark – yet they are similar in where it matters most: being able to effectively lead WFAN.

“I think they both very much understand radio, and that’s the most important thing,” said Roberts. “You’re the program director of WFAN; I think you have an idea of what good radio is… [They are] both very, very intelligent radio guys that I trust, but everything else about them is probably polar opposite.”

For aspiring professionals looking to pursue a career in sports media, Roberts advises them to take advantage of the innovations in media and communications especially when it comes to podcasts. With widespread evolution and progression in technology coupled with altering consumption habits and means thereof, putting in the time allows novices to hone their skills and position themselves well in sports media. That and always being willing to learn and study to be the most prepared and informed host as possible – especially when talking to listeners, many of whom have seen teams in their ebbs and flows.

“My wife knows that I’m going to watch every pitch of the Yankees and Mets game,” said Roberts. “I may do it on DVR, and I may do it at 2 in the morning because we need to have a life; I don’t want to get divorced, and I want my kids to love me, but she also knows that I want to be as informed as anybody on the radio and that’s not going to stop.”

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Jake Paul, Betr Pair Micro-Betting With Media

There are plenty of hurdles, though, that still need to be overcome before this takes over the betting landscape.

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I’ll be completely honest: I can’t get into TikTok. I’m closing in on 40 years spent on this planet, and it’s simply not my thing. It’s not meant to be, though. The current generation is one with shorter attention spans, the kind that wants a quick highlight of a sporting event so they can shift their focus to something else. When I tell folks a decade younger than me stories about how I–and others of my age group–would sit around and watch an entire SportsCenter, they look at me like I’m crazy. Not sure how they’d look at me if I told them we used to often watch the rerun an hour later, but that’s another discussion.

It’s a big reason why micro-betting is considered the “next big thing” in sports betting. Similar to in-game betting, micro betting goes a step further and focuses on individual events within a sporting event, such as the outcome of a drive, whether a baseball player will get a hit in his upcoming at-bat, or even something such as a coin toss at the Super Bowl. A perfect example of micro-betting is the rise in popularity of betting on whether or not a run will be scored in the first inning of a baseball game. For a generation that wants a quick resolution to their bets, it makes total sense. You place a bet, you find out how it did, and then you move on–whether that’s to another bit of action or something else entirely.

Something else I can’t get into is the whole hoopla surrounding the Paul brothers. Logan and Jake Paul have built an empire for themselves on the back of YouTube, with Jake Paul having more than 70 million followers on social media. For various reasons, I’m not a fan of either individual. Again, though, they aren’t coming after my demographic. Like them or hate them, you have to respect their grind –and you have to admire their business acumen — as they parlay their notoriety and success into sports entertainment by way of boxing and the WWE, as well as a new sports drink company that has already partnered with Premier League side Arsenal. 

Monday’s announcement by Jake Paul of a new micro-betting site simply furthers the narrative and does so in a manner that can’t be ignored by those in the sports betting space. Betr, a joint venture between Paul, sports betting entrepreneur Joey Levy, and the sports betting company Simplebet, was announced yesterday morning. Backed by a $50 million investment from multiple venture capital firms, the new company is backed by ownership groups of franchises such as the Boston Celtics and San Francisco 49ers, and also has financial backing from current and former NFL players including Dez Bryant, Ezekiel Elliott, and Richard Sherman. Musician Travis Scott has also put his financial backing behind the product.

The other very interesting tidbit from the press release was the announcement of a media company that would feature, among other shows, “BS w/ Jake Paul”. Their new YouTube channel, which already has over two million subscribers despite not a single video being posted as of Monday afternoon, will feature sports-betting content from Paul and other content creators and will focus on micro betting. In an interview with Axios, Levy said that consumers can “expect 10+ videos a day from emerging content creators we’ve brought into the company,” but that things would begin with a focus on “premium content natives, starting with Jake’s show.”

Sports radio and television have long been focused on making their products more appealing to younger generations. Just take a look at ESPN, where they’ve long been doing “SportsCenter” episodes on Snapchat. This could be a game-changer, provided they can help drive micro-betting into a wider market. 

There is plenty of potential in the space, a big reason Paul was able to acquire such high amounts of funding. Just last year, JP Morgan estimated that more than $7 billion per year would be wagered on micro bets by the year 2025. And earlier this year, the CEO of Oddisum stated in an interview that micro-betting would account for the majority of wagers placed on sporting events within the next three years. Even DraftKings CEO Jason Robins has talked about plans on how his company expects to embrace the trend.

There are plenty of hurdles, though, that still need to be overcome before this takes over the betting landscape. The biggest one is the delivery of data. As we move more towards a society that streams sporting events and other digital content, the delay between real life and what shows up on your mobile phone can be the difference between placing a wager or not. For some services (I’m looking at you, Peacock) there’s often a delay of more than 90 seconds, which means the play I want to bet on is still two or three plays away from being seen with my own eyes. That makes it difficult to place a bet with any sort of confidence.

The other major obstacle will be getting their gambling service legalized. In their press release, Betr stated they will start as a “free-to-play” app in all 50 states, and eventually they will add real money gambling services as they become licensed to operate within individual states. That’s not going to be so simple, though, as gambling addiction concerns continue to rise and multiple state legislatures are already having discussions regarding the matter. 

As addictive as betting on sporting events can be, micro-betting is often exponentially more. A study last year from CQ University in Sydney, Australia indicated that micro bettors are more likely to be younger players and that they usually “have high trait impulsivity”. An author of the report also stated, “there’s a very strong link between micro betting and gambling problems”, and pointed out that the short amount of time between placing a bet and having it resolved leaves little time to evaluate performance or track one’s bankroll. 

Whether or not those things are overcome in every state possible is a discussion for another day. The fact is, micro-betting is more likely than not to become a huge growth market for sports betting companies over the next two to three years, and Paul and Levy have become the first big players to jump into the media space. It’s not a question of if, but when, others will follow them into the realm of micro betting sports content, but their announcement on Monday raises the stakes. It also reminds those of us in business, especially sports media, that while we may not fully understand the allure of what the younger generation enjoys, we ignore it at our peril. 

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