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A Conversation with Sarah Spain

Demetri Ravanos

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Sarah Spain seems to be everywhere for ESPN these days, and that’s a good thing. As sports fans’ relationships with the hosts and reporters they follow has changed thanks to social media, Sarah is about as real as it gets.

Her show with Jason Fitz on ESPN Radio is built on long, thoughtful conversations instead of competing hot takes. Her podcast That’s What She Said is a window into her personality, a chance for her listeners to learn who and what Sarah finds interesting. Her writing reminds us all that there is a world beyond sports for anyone involved at any level of the industry.

Speaking as a consumer and sports fan myself, I have always found Sarah very easy to connect to as a viewer. She seems to embody the idea of entertainment over access. That doesn’t mean she isn’t very professional or isn’t good at what she does.

When I see Sarah Spain on TV or hear her voice on the radio, I can always tell that she is showing up with the goal of delivering for her audience. It could be funny. It could be informative. It really doesn’t matter. The point is you are going to be happy you invested time listening to what Sarah Spain had to say.

We spoke about a week and a half ago. She was on her way to the airport, leaving Bristol after a morning on First Take to make it home to Chicago in time for her radio show that evening.

Our conversation focused on the lessons she has learned from her experience in the sports media world, but along the way we made time to talk about Christmas-themed pub crawls, her rap skills and Bobcat Golthwaite.

D: When someone says they recognize you, what is it usually from?

S: Usually Around the Horn because it is visual, but a lot of LeBatard too, especially once I talk. It depends too, because if I am in Chicago it might be a lot of local radio and there are a few that know Spain and Fitz too, but mostly it is Around the Horn because it’s everywhere. You see it in every airport. It’s on at least one TV in every bar.

D: So when you meet someone that isn’t a sports fan, how do you describe what you do at ESPN? Like you said, you’re on everything.

S: If they want a short answer I just say “I’m a host and writer at ESPN.” Then if they ask “For what?” that’s when I’ll get specific with Spain and Fitz and I do a podcast once a week and then I write for espnW and I do some SportsCenter reporting for the Chicago teams. And then, of course, you have to mention Around the Horn twice a week and the LeBatard Show.

D: How does preparing for the radio show differ from podcast preparation?

S: Well, the podcast is really different. The podcast is where I get to talk to people that I find really interesting and explore their journey to how they got to where they are and became successful at what they do. That’s really just looking into the background of who they are and what their career has been like. I read. Sometimes I’ll listen to other podcasts they’ve been on.

For the radio show, you know, that’s mining through the news of the day to find out what we find interesting and decide what kind of conversations we want to have about them. Plus we look at the funny stuff or even the serious stuff that isn’t a major headline that we want to weave into the biggest news of the day.

D: How much of your day is devoted to prep? With a national show, and in particular a national night time show, I would imagine there are times you have to remind yourself to turn it off and spend time with your family.

S: No. I mean, there are days where I am swamped and I am working straight through until I get to show prep, which is an hour and a half before the show. The nice thing about having a regular show is you usually won’t have giant gaps of knowledge that have occurred over the course of one day or one weekend, unless you didn’t watch the game, didn’t read anything about it, and didn’t post anything.

The majority of days, I would say I am a big podcast listener between various activities. If I am going for a workout and it’s not a class where I have to listen, I’ll put on that morning’s Golic and Wingo or Dan (LeBatard) or Will Cain to see what those guys are talking about. I also read a lot of articles when I am in transit or sitting down before we start show prep to get a handle on the things that I am into.

It kind of depends too. If I am doing Around the Horn, that means the day starts with a call at 9:30 and then between getting to the studio, sitting down for makeup, and other prep, I usually only have about 45 minutes before the show meeting starts. On those days, I’ve spent my whole afternoon prepping, so I come into the radio show hot with all the stuff we’ve talked about on the TV show.

When you do a radio show every night until 8 pm, there isn’t a lot of time to get anything done after that. So sometimes that means my morning will be about running errands or taking care of my dogs or something to do with my family. On those days I get creative about how and where I do my prep.

D: On days like that, how much are you leaning on your production staff for radio versus say a day on Around the Horn?

S: Well, Around the Horn is great, because they always have a packet full of stories and stats and interesting did bits, so you can pull out the stats and bits you think are most noteworthy. For radio, our producer puts together a shorter packet that Fitz and I will kind of add stuff to, so it kind of depends. For radio, you know, that more of what we find interesting or what we feel needs to be talked about, where Around the Horn is more about the producers.

When we get on the call (for Around the Horn), we certainly have the ability to say “I don’t think this is a great topic” or “can we tackle this differently?” and the producers listen, but they really are the ones driving the bus. The two are really different in that way.

D: What was your relationship with Jason Fitz like before you started doing a show together? Did you look at him as someone you liked and could be really successful working with, or did management view it as “Here are two people that have been on ESPN Radio. Let’s put them together and see what happens.”?

S: I was doing Izzy and Spain at the time and it was only two hours, and he was filling in a lot for Jalen and Jacoby and that was two hours. A couple of times, I think it was four times, our bosses decided to put the shows together and just do four hours of the shows together. So, that was really the first I had ever even heard of him or knew anything about him.

It was a blast. We had great chemistry together right off the bat. We really hit it off. I found his background super interesting. I liked his approach to things. He’s still really excited about the job and enthusiastic about sports in general. He’s very genuine in his thoughts. Jason isn’t very big on needing to be fabricated or needing to have a take that is going to make people go crazy.

So after that, they were going to change my show, They were looking around for who they were going to pair me with, and I had really enjoyed working with him and Mike Golic, Jr. So I thew out those two names. GoJo was already going to be doing his dad’s stuff, but the radio people really loved Fitz too. They thought he was an up and coming star, and so that was that.

We ended up meeting up in person once. My friends and I were in Nashville for a music festival and I messaged him to say if he and his wife wanted to meet us to go out for the night, that would be awesome. It was really nice to meet him in person and hang out socially. That was really it. We met one more time in Bristol for the photo shoot to promote the show. So we started the show really only having met those two times, but we really just hit it off like gang busters.

We have a ton in common, including really silly stuff. Like, we’re both into costume parties and Christmas pub crawls. I’m having an SNL-themed birthday party this year and his wife had the same kind of party last year. We’re both really obsessed with our dogs.

I like having someone else that comes in with just a lot of energy. We want our show to be thoughtful and fun and not like a lot of other shows.

D: You guys are still hooking up over ISDN, right? You’re not physically in the same space when you’re doing the show.

S: Right. I’m in Chicago and he is in Connecticut.

D: That may not make things harder necessarily, because like you said, you guys already have a raport, but it probably took some feeling out I would guess.

S: Certainly it would be easier to be together in person, but we do use cameras on our computer so we can look at each other and maybe hold up a finger to say “I want to jump in” or “I want to go next”.

Especially with radio from afar, I find that I have a lot of sarcastic asides that I want to get in. I don’t want to take the conversation back. I just have a sarcastic comment I want to get in or I want to make fun of you real fast and we can just keep going. That can be a little easier to do in person, but thankfully Fitz is on to me. He knows that I am just going to make fun of him real fast and let him get back to his point.

D: (Laughing) I have spent so much of my sports radio career as a third mic, where those sarcastic asides are one of my primary roles. It’s funny the way someone who doesn’t quite get your rhythm yet can be thrown off by that, where as I think people like you and me look at those kinds of comments like they are just part of a normal conversation.

S: Right. “Keep going! Of course I am going to make fun of you. I have funny things to say and need to be heard at all times!”

D: I do wonder how the way you prep for your podcast helped you get to know and understand Jason Fitz, because you don’t have to delve too far into his past to realize that it is so different from most people in sports media.

S: Yeah, I actually had him on my podcast pretty early on for that reason. He was so new to sports that I wanted to give listeners that wanted to know who he was the chance to meet him and learn who he is and what led him to this point.

It was important for me too. I think chemistry can come very very quick, but people listening will be able to tell if you really know each other and are friends by the commentary and the jokes. Can they hear that you know each other’s lives? So, it was important to me to have that hour chat and just be able to pick his brain, but also Fitz and I are really open about our personal lives and our friends, so it makes it easier to know thing about each other without really having to pry.

D: With your podcast (That’s What She Said), what is the difference in your preparation for a sports guest versus a non-sports guest? One of the more fun conversations I have heard you have was with Dan Soder, who is a comedian and pretty far removed from the sports world.

S: It’s not very different, to be honest with you. It’s so similar, because I don’t really want to talk to people about the news of the day. I did one with Greg Wyshynski before the hockey season to talk about him just joining ESPN and give everyone a quick primer on what they needed to know to enjoy the season. Usually though, I am not talking about a specific place and time. I want to know about that person and how they got to where they are.

I think as I get to doing second time around pods, I may go back and listen to the first episode I did with that guest to see what I missed or follow up on stories they told before. Right now though, it’s really the same no matter what their job is.

It starts out with who they are, what their childhood was like, the decisions they made that got them to where they are, and if there are larger thematic issues I want to get to, we might do that at the end, but honestly, interviewing these people for the first time, I want to know what brought them to this place in their lives regardless of what that place is.

D: When you first joined ESPN, what did they tell you about wearing your Chicago fandom on your sleeve? Because that, I think, is a huge part of your appeal. It is part of Vn Pelt’s appeal the way he talks about the University of Maryland. What was that conversation like about being a fan versus…I don’t know, being a professional or whatever the word would be they use.

S: It didn’t come up for a little bit actually, because my first gig with ESPN was at ESPN 1000 in Chicago as an update anchor, so that is mostly just straight, although they did tell me they wanted me to add some personality. So that changed my delivery sometimes to something like “Blackhawks eliminated the Canucks with a game six win last night, so hand that golf bag right over to the Sedins” or whatever. So for the most part that was it. My appearances on the station were tinged with bias, as anything is in a local market.

When I joined espnW about 8 or 9 months later, that was less about my fandom and more about the specific assignments of that job. It wasn’t something I ever hid or that they asked me to hide. I think the first conversation I remember having about it was when they called me up and asked me to do some SportsCenter stuff, and that is only when those teams are hot, so the Blackhawks or Bulls playoffs, the Cubs’ run. Even just recently they sent me to cover Loyola.

In that case, I do like to have the conversation of what is my role. I’m not a bureau reporter. I’m not Josina Anderson or Michelle Steele. All I heard was “we want you to be you. We don’t want you to change or be ‘reportery’. We want Sara Spain’s reaction.” And then on top of that it is what is the mood? How does the city feel? What is the vibe?

It’s engrained. People would rather hear it from someone that is living it and gets the vibe rather than someone that is parachuted in to say “Well, Cubs fans seem very nervous.” That just doesn’t feel the same as me saying “Well, there’s a lot of puckering going on, and I’m not going to lie to you. It’s getting pretty real around here.”

That’s the difference in all outlets now, is that there is this understanding for certain jobs. It’s not going to work for Adam Schefter obviously. There is no harm in showing your allegiances, particularly if you can prove that you aren’t going to be too soft on your own squad. Sometimes I am more critical of my own guys and openly disappointed when they aren’t doing things right.

I think the Patrick Kane story is a good example of me getting simultaneously accused of going easy on him because I am a Blackhawks fan and also not giving him a chance to defend himself because I am a woman that has covered sexual assaults in sports. People are going to assume biases in any direction in sports anyway. I think the goal is to be as fair as possible at all times, so that can’t get you on anything genuinely if you’re covering things equally.

D: I started thinking about that a few months back. I live in Raleigh, NC, where Bomani Jones came up doing radio and he and I have been friends for a long time. He told this story on his show one time about the two of us watching the Bama/Texas National Championship game together and he said something on air to the effect that it broke his heart.

I immediately flashed back to being in college and listening to Dan Patrick. I distinctly remember him saying at one point that he was a Cincinnati Reds fan until he started doing this professionally. I think Bomani talking about Texas breaking his heart, you talking about the Cubs is a step more towards what sports radio should be as opposed to that old school demeanor of we wear a suit and tie and have no emotion about the outcome.

That’s not to take anything away from Dan. His show is the reason I wanted to be in sports radio. I guess they way you allow yourself to be a fan feels a little more real and of the time.

S: Yeah, certainly for the sports radio medium, right? I still think there are absolutely elements of sports reporting where there is an appeal to the idea of what you are getting is absolutely unbiased. I think for the beat reporter, and the Schefter’s, and the breaking news people, that makes sense. But I think if you’re going to be a host, I don’t really see the point in trying to hide any fandom if you have it.

Now, I don’t think you need it. Particularly if you are a national host, there is no need to interject your fandom throughout, but if you have it and it’s natural and it’s passionate, it drives conversation in a way that’s interesting. So, why not? People are going to figure it out anyway.

Even someone like Mike Wilbon, who was on back when they were encouraging more neutrality, you know his teams. You know where he went to school. You know where he came up. So trying to hide it would be just kind of silly.

D: So when you’re coming up in sports radio and starting to host shows on a national platform and you’re so closely associated with the Dan LeBatard show, how do you go about trying to carve out your own identity? Because when you’re on that show listeners know you in the Commish role. What was your thinking in trying to trying to establish something different than that for Izzy and Spain or Spain and Fitz?

S: Actually, my first national radio exposure at all was on a weekend show called Spain and Prim.

D: Oh right. And then the Trifecta (alongside Jane McManus and Kate Fagan).

S: Yes, so when I did my first appearance on LeBatard was to discuss Patrick Kane. No, the first one was Mayweather and then maybe Patrick Kane. Maybe Ray Rice was somewhere in the middle. Anyway, it was always these very serious issues I was writing about for espnW.

I think during that time, Dan realized they had never had a woman come in as one of their regular guests and thought that I might be able to go toe to toe with them on some of those issues and give it a shot. So, when they first asked me to come in, I listened to that show occasionally, but I wasn’t a regular listener, and you need to listen to them on the regular, right? It is so of the time.

I walked in that day not knowing what to expect and not really able to keep up. I didn’t even know what The Club (the LeBatard Show’s weekly recap aired in the show’s final segment on Fridays) was. I didn’t know we were on the air when I was asking him to explain it to me.

Radio listeners in Chicago knew me already. Maybe there were regular listeners of Spain and Prim or the Trifecta that knew me already, but LeBatard was huge in terms of getting my voice out.

The Commish thing is funny. It just came out completely organically. It came out of either the second or third time I was on. Stugotz had to eat all the powdered donuts from the Grid of Death (LeBatard’s list of punishments he and his staff must complete for picking games incorrectly during the NFL season). I am a stickler for rules. I always have been, and I think it is a waste to do the grid of death if you are going to chicken out and a waste of people’s time if you are not going follow through.

So I was like “Wait, you’re crumpling the donuts up and brushing the powder off. You’re managing to get away with throwing away donut you should be eating. Keep your hands above the table!” And he was like “Jeez. She’s like the commissioner of the grid.” It sucks a little bit because I guess my personality is a little bit bossy, so it felt like the perfect role.

D: Well, the rap certainly helped.

S: Yeah, the rap took it over the top. It seemed natural to use that as my rap alter ego.

I think what’s very interesting is that there is a lot of feedback on the LeBatard show. It is a community. Dan’s very aware of it. Stu’s very aware of it. The guests are very aware of it, wanting to, as they say, “fit in don’t fit out,” and I got a lot of positive feedback early on. Then the guys that run the LeBatard reddit page asked if I would do an “Ask Me Anything”.

There were certain questions that made it feel like people that I was trying to act like I could be a certain way on that show. I think that was more just, they just weren’t used to hearing a woman be the way that I am. I am just not very stereotypically diminutive in any way.

I like to talk smack. I have a lot of opinions. So, they thought it was sort of fake. I think, and I hope, that most people have figured out that that is just sort of who I am all the time in any context. I think people who listen to me regularly know that’s who I am.

I think you have to be on LeBatard enough times that people can get used to you, because it’s hard for anyone to step in. So, you just do your best to fit in with their vibe and bring whatever you can to it.

I also have always said that I would rather be thoughtful and honest and speak up when I think something is wrong or offensive or even just stupid. You know, some people don’t want to hear opinions that don’t jive with theirs, but sometimes I am going to have those and that’s okay.

D: I would imagine just by virtue of being a woman in sports radio you have to deal with a lot of people that think they know more than you or are confident that you’re putting on an act.

S: Yeah, well what is interesting is the assumptions about me are so varied. It’s either people on Twitter telling to me quit pretending I am watching the game, which is like “What? You think I don’t even watch sports?”. They’ll respond with something like “They’re just going to give you some talking points anyway” and I’m like “That’s not how this works.”

So it’s either to that extreme or people going to the extreme of “Oh you’re not really like that.” And with that, all you can do is genuinely be yourself all the time and hopefully they see that is who this woman really is.

D: Yeah, but even trying to win people over in that way, I would think looking at Twitter must be tiring for you sometimes.

S: Yeah for sure, it can be super exhausting. Other assumptions about women in sports that can be super exhausting are like “you slept your way to the top” or “you’re only in it to meet athletes”. I remember my mom when I first started because they were really off base. Like, they go find a photo of me on vacation from like 15 years ago and be like “you’re always showing your boobs” and in actuality I never am.

Find a photo of me doing my job where you can see them or can even remotely tell I have them. I am constantly hiding them. You found a picture of me on vacation from more than a decade ago. Those are on Google because other people found them and made stupid lists, not because I’m putting that out there.

That happens because people make assumptions about others when they don’t know them. That absolutely happens to every woman with big boobs no matter what. There’s always going to be a whole bunch of assumptions being made just purely based on that.

I get less bothered by people insulting me, like saying something rude, than I do by feeling like I’m misunderstood. If someone wants to be like “you’re fat” or “you’re ugly” you can just think to yourself “oh that person’s not very nice,” whereas if I get “I can’t believe you said x,y,z” and I respond with “No, here’s what I actually said and here is the nuance to it” and they just give up because, frankly they aren’t smart enough to have the argument, that’s what infuriates me.

I shouldn’t be annoyed by some random person, but the fact that they misrepresent what I said because they don’t want to take the time to listen or understand is so annoying. Like just yesterday I was writing some tweets and making jokes about Jemele (Hill) directly to Jemele, and some people who didn’t get the context were asking Jemele “who is this bitch trying to get famous off of you” or telling me “You’re a coward Spain because you deleted what you tweeted.” I had to say “No, no, no. What I retweeted was deleted, so go talk to that person. And I was making fun of the clip! And I’m friends with Jemele. You’re confused!”

I’m more confused by lack of reading comprehension and not understanding sarcasm. I think that is true of most women trying to crack jokes on the internet. I think it has gotten a little better, but there is still that group that thinks “there’s no way she’s making a joke, because a woman wouldn’t get that”.

I remember the rap that I wrote for the Commish bit (on the Dan LeBatard Show) one of the comments I saw was “That was really funny, but there is no way she wrote that. She wouldn’t know all those show references.” What? I’m on the show! Of course I know all the show references!

D: For you it’s not only online though, right? I mean, look, I love sports radio. I love studying and writing about sports radio, but there is this segment of our audience, particularly in the older end, that doesn’t want nuance. The sports radio they like is a bunch of listener calls and have a take and don’t suck. Nuance isn’t something we have always done well in sports radio. So, forgive this term, but I from a radio perspective, I am sure there is a very dumb segment of the audience that you have to fight back against.

S: Tony Reali told me he is going to start muting me when I use the word “nuance.” He has his buzz words that annoy him. He doesn’t like “narrative.” He doesn’t like “optics.” He says “nuance” is going to be one of those words for me now too, because sometimes he’ll ask me a question and I say “Look, the answer isn’t as simple as a yes or no. There’s nuance to it, because it depends on x or y.”

I am still learning. When I first started doing radio I would answer questions with “Well, we’ll see,” and my program director was like “No, that’s not a take,” and I would say “Yeah, but we will see!” and he was like “Nope. That’s not how this works”.

So I’ve learned to have stronger takes, but I am still never going to be one of those people that thinks I’ve gotta pick a side and I have to hammer it home like I’ve never believed anything more in my life if there’s a part of me that thinks there really is some grey area there.

That’s one of the things I really like about my show with Fitz. It’s what I like about LeBatard’s show. It doesn’t feel like anyone is coursing their way through takes. It feels like there is time to have intelligent conversations.

Now look, not everyone is going to like that. Absolutely there are sports fans that just want the yelling. They don’t want to think too hard. I did Second City Improv, the conservatory in LA. They would always say about our improv “Always assume your audience is smart. Make them come up to your level, do not ever think you need to play down because they aren’t going to get this joke.”

I feel that way about sports radio. I think there are plenty of intelligent and smart and thoughtful sports fans who want to hear real conversations and not just back-and-forth yelling on a take. I hope they’re the ones listening, and if there are other that don’t like it, that’s fine. They can find other places to go get their sports.

D: What sort of advice would you give a host about diversifying their media presence? You’re on TV and on the radio and you write and you host a podcast. Let’s take it a little bit at a time for the guys on the local level. What would be the advice you would start with for establishing a podcast presence outside of the radio show?

S: I tell people coming up that they need to be diverse in their skills. Even if you grew up all your life thinking “I want to be a TV person,” well you better still know how to write. You better be willing to give radio a shot. I never thought I wanted to be on the radio and now I love it. It is a huge part of my career.

The writing thing is one of the most important things I tell up and coming people, because texting and social media has turned people’s English into garbage. It’s such a bad representation of you as a professional if you can’t write an email or a letter that comes across as remotely intelligent.

I always tell this story and it is so random, but when I first moved to LA and was trying to be an actor I found this book that was one of those things that you do when you go to LA. You get an agent and you go to Samual French and you get this book.

There was an anecdote in it from Bobcat Golthwaite. Most people I talk to don’t even know who that is. I don’t know how old you are, but do you remember Bobcat Golthwaite?

D: I’m almost 37. Prime Hot to Trot age.

S: Okay perfect. You’re on my level then. I usually have to say “kinda like Pee Wee Herman.” He’s just someone who’s different and weird and doesn’t quite fit in. I can’t think of a modern equivalent, because the way our media has changed, it is full of weird and quirky people, but it didn’t used to be.

Anyway, the point of the anecdote was that there wasn’t anyone in Hollywood going “Man, we really need someone that half wheezes and half talks and his face screws up into this weird look and he never seems to make any sense” and Bobcat Golthwaite walked in and said “here I am!”.

No, he showed up. He was uniquely and strangely himself, and he created a space that no one even knew they needed. Same with Pee Wee Herman, right? No one knew they were looking for that, so he created his space. The advice was don’t try to be a version of what you have already seen. You’ll just be a copycat. Instead, be yourself and if you need to, create a space.

I really took that to heart in my comedy and when I was getting into sports. I took all that I learned in Second City into the sports world, because I thought it didn’t seem like women were allowed to be funny in sports. All they could be was bubbly sideline reporters or serious anchorpeople, and I thought I think there is a place for women to be funny if they know their shit.

That’s my advice. Figure out what it is about you that’s unique. Don’t worry about filling a space that exists. Especially if you want to be diversified, people need to know who you are and what strengths they are getting out of you even in spaces where they may not make the most sense. Stugotz is Stugotz on the radio and he’s Stugotz on SportsCenter.

That’s what was great about ESPN telling me with SportsCenter they wanted me to be me. My first appearance on SportsCenter I said the Bears were a garbage fire. I didn’t say “well, the team is struggling this year”. I was myself. The Bears are a garbage fire.

If that’s not who you are, that’s fine. If you’re someone that prides themselves on being professional and serious, there is a model to follow in Bob Ley, but whatever it is, I think the key is if you want to be on all these different platforms, people need to know what to expect no matter the space or place.

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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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