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Meet the Bettors: Kelly ‘In Vegas’ Stewart

“There’s so much free content out there. Like we have 38, 39 states about to be 40 states coming on board, and the more states that come on board, the more mainstream that gambling has gotten.”

Demetri Ravanos

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Kelly Stewart is the kind of person that the gambling media needs. She has thoughts not just on the players and results, but she thinks hard about the industry and what trends will be the next to rise to the top.

Maybe you first heard her name because of the controversy surrounding her hiring and firing from ESPN. Maybe you’ve never heard her name at all, because you only know her as Kelly in Vegas. 

What I can say for sure is that she isn’t hard to find. Her content is everywhere. She hosts shows for Outkick, the Superbook, and WagerTalk, a brand she also owns a piece of.

Kelly is the latest conversation in our Meet the Bettors series presented by Point to Point Marketing. We talk about the evolution of gambling Twitter, the challenges faced by media companies launching their own sportsbooks, and why customer service is so important for picks services.

Demetri Ravanos: Can you tell me how you learned to make your way, and I might even say conquer, gambling Twitter? I mean, that’s how most people came to know Kelly in Vegas in the first place. 

Kelly Stewart: Oh, boy. I don’t know if I’ve even still been able to navigate gambling Twitter. It is such an awesome place and very unique. I’m going to say that, because I have met some of my best friends in the world on gambling Twitter. But my brain also wants to say the word cesspool because that is also what it is, right? 

DR: Chris Fallica from FOX used that exact same word for it.

KS: There is so much hate and vitriol when in reality we all have the same goal. We’re all laying eleven to win ten. It’s all of us versus the bookmakers. These trolls on the internet, unless they’re bookies, which they could be, should not be mad at me. I’m not battling. You know, my good friend Hakeem has it pinned to the top of his page from years ago. “I’m not here to compete with anyone.”            

Once you kind of realize that the competition is you versus the books, this is a competition within yourself and you’re trying to be a better version of yourself every single day. Then you really start to look at Twitter a lot differently.            

I’ve muted several types of words. I muted tons of people. Unfortunately, I’ve had to block some people, but overall, I would say that is a great place to have some really cool discord, whether you agree on a team or you disagree on a team. I have gotten great information from absolute utter strangers in my DMs. “Hey, just so you know, this team’s flight is four and a half hours late.” I mean, this is years ago, before it became public knowledge like it was with the UConn team plane. It was stuff like “Oh, hey, I happened to watch practice today, and this is what happened to point guard A” or “Guy B got carted off.”          

Being able to get the best of the information is so critical. So, when you have that network and it works to your advantage, it can be a really beautiful thing. 

DR: So, whether it is because Twitter has changed or because the amount of access to gambling has changed, how have you seen gambling Twitter change? 

KS: Well, it’s crazy because when I got on Twitter in 2009, you just said whatever without any repercussions. Clearly, I was one of those idiots. You just got on and you just typed away.           

I could go on and say, “I don’t like Notre Dame for this reason,” and every Notre Dame person would be mad at you and tell you why you’re wrong. Then it became just such a bigger entity.    

You’re absolutely right. I think gambling Twitter, pre-PAPSA, was a little different. It was a lot more of a hateful place. Touts, people that sell picks, were all over it. It was like the tout world with the customers being able to talk back, and then there was a battle between touts. Who’s smarter? Who knows more? Who’s getting better information? Who’s got the best CLV (closing line value)?        

Now, it’s just such a free for all. There’s so much free content out there. Like we have 38, 39 states about to be 40 states coming on board, and the more states that come on board, the more mainstream that gambling has gotten. That’s really what’s happened to Twitter, too. It’s really brought out a younger demographic. I mean, some of these kids that produce content are barely old enough to place a legal bet, right? And they have more followers than I do! It’s because they’re objectively hilarious. They’re objectively more talented from the creative standpoint. No one is watching them because they win or lose. They’re watching them for entertainment.        

You even hear the word, wager-tainment, which my friend Nick Kostos coined. It’s really interesting because people are going to hate you even when you’re winning, right? They’re going to hate you when you’re losing, but they’re going to still hate you when you’re winning. But if they’re entertained, they’re going to stay around. It’s a really unique pair of words that he put together to describe what I think Twitter is really turning into. 

DR: Let’s circle back on something you said, regarding touts because I do want to ask you about that. But first, just sort of give me an idea of where all people can find your content these days because you’re not just at Wager Talk. 

KS: No, I’m actually all over the place. So, unfortunately, with the layoffs that happened over the summer at Barstool Sports, I was one of those and I thought, “You know, it’s end of June. Football season’s right around the corner. I’ve got a lot of work to do, and I can’t be worried about scrambling to find another job. I’m just going to freelance.” So that’s what I’ve been doing since then.           

I have talked with several companies about what I want to do, and I have to make some decisions with my agents, but as of right now, I’m all over the place. I revived The Kelly and Murray Podcast because that was something that I really enjoyed doing. I’m doing a little bit more stuff for the Superbook. I’ve been friends with those guys for years, so that was a very natural fit. You already mentioned WagerTalk, which has been such an integral part of my career. I owe those guys the world, and they gave me a little piece of the company, so that didn’t hurt either. Then I even got into doing some more of what I would call daily fantasy stuff, but more from the player prop side, which is kind of in a gray area.  Some people say it’s gambling, some people say it’s not. It’s definitely gambling. Whether that’s Betr or the Prize Pick world.           

I was doing the rough with Betr. Those guys were super fun because they are hyper creative. Like, that entire office is just a creative vibe. Those guys and I parted ways after Super Bowl because, well, there’s not a lot for me to do until football season starts again. Then I partnered up with the Slash Sports guys. So, we’re doing survivor contests. My girlfriend Pam and I did a Masters pool, which was really tough for me because I have been slacking on the golf front, which is why I decided to partner with Pam. She’s such a great golf handicapper.

Now, I’m just trying to sift through all of it. Where do I want to be? I’m doing some of the stuff with Outkick, which, of course, is now owned by Fox. We’re in some negotiations about what is the bigger picture for me with them, but really, I’ve just been enjoying myself this whole season and saying, which is not something that when you’re under contract, you really ever get to do. You’re pretty much exclusive to that one entity, and that’s okay. That works for some people. I really like being able to kind of set my own schedule. I got to go to Mexico last week for one of my best friend’s birthdays. That would have never happened if I worked in a very rigid, corporate media position. They’d have been like, “you want to go where for March Madness?” I remember telling Clay I was like, “Oh, I’ll be in Mexico next week.” He goes, “Do you want to cancel the show?” I was like, “No, I’m doing it from the beach.” 

DR: As a gambling content creator, do you ever approach making a new video or podcast, whatever it might be, do you ever approach it with the idea of your goal being turning people into gamblers or are you always approaching it with the idea that you are talking to people that are already gambling? I don’t mean for that to sound nefarious, but is there ever stuff that you are putting out there in your mind, at least, part of the goal with it is to show people that might be interested that “hey, this doesn’t have to be as scary as you think it is?”

KS: That’s very interesting. A few years ago, we were filming a series at the Superbook on showing people how to bet. This was way before phones, right? Like we’re talking 2017, 2018. What it was, was “are you scared to walk up to the window? Well, here’s what you do before you walk up to the window.” So, you’re prepared, right? The videos did okay. Then phone apps came out. Now we don’t have to explain that to people because they just start typing on their phone and they figure it out, right?           

My boyfriend’s little sister, we live in Florida. She’s like, “I got a Hard Rock account.” I’m like, “why?” She got it because “I want to put money on the games with my boyfriend, and I want to have fun.” And I’m like, “how much money did you put in there?” She says, $200, and I go, “okay, what are you going to do when you lose that $200? Because it’s going to happen.” And she’s like, “Well, I haven’t thought that far yet.” I said, “Well, you should think that far.” You know, I hope at WagerTalk, what we do is educate people to become better bettors.           

I don’t think I actually have really done much in terms of growing people into gamblers. Maybe that’s something I should look at, because if you have somebody who’s green and doesn’t have any experience and you explain to them in the beginning, you are going to lose, you’re laying eleven dollars to win ten, and here’s the reality versus they’ve already been gambling for 50 years. Those people are like, “quiet lady, I’ve been doing this for a while and don’t need your opinion.” It’s kind of funny, because some of those people, you can’t educate them. There are other people who are willing to learn. I wish I had a better answer for you because I don’t think that I’ve ever gone into it. Like saying, okay, we need to get more gamblers, but definitely some companies I’ve worked for, that’s how they make money. 

DR: So, I want to circle back on the tout discussion because, especially in states where online is legal, getting information as you place your bet is very easy. In a lot of cases, the tout advertising that used to be all over local TV and radio at night has disappeared. The idea of those businesses has become almost like a bad word.

WagerTalk is a pay-for-picks service. So talk me through how it’s different from the days of calling a 1-900 number and having to wait five minutes to hear a lock of the day. Why does one work in 2024 and the other doesn’t?

KS: We’re definitely a pick service. The bottom line, yes, we have a YouTube channel with 100,000 plus subscribers where we give free information out every single day, but you’ve got to watch the shows to get it for free. You’ve got to follow the Instagram channel. You need to follow some of the guys themselves. They give out tons of free information and that I’m very proud of. As I mentioned, my goal is to make people better bettors and to lose less money. Something that used to get said in the industry a lot when I worked for Don Best in like 2013, 2014 was “People don’t stop buying picks. They stop buying picks from you.” Like, that’s kind of weird but not incorrect.           

I wonder though, as the generations get younger, if people are just going to stop buying picks, because here is what the other psychology of it is: why do people buy picks? Well, because they want to win or they want to think they’re going to win, but if they still lose, they want someone to blame. I find that also to be another interesting side of the psychological aspect of gambling.           

I’d also like to think that people are paying for information that they don’t have.  Let’s use Ralph Michaels, for example. He and I do a weekly show during football season called Bet on It. His segment is called “Trends and Angles,” and I only want actionable information from Ralph. I don’t want him to say, “well, the last ten games, UConn has covered the spread in the NCAA Tournament.” That stuff you can find everywhere. “Yeah. Thanks, Ralph. We know that, right?”  

He’s not going to do that. He’s going to dig deep into a database that goes back into the 90s. And he’s going to say, “here’s how double-digit home dogs have done in college football since 2003.” Like he’s got something to either play on a game or play against a game. When you’re getting his stuff, you’re getting a lot of that actionable information that might not only pertain to that game, but several others throughout the course of the season. There are other guys like Marco D’Angelo who don’t use a lot of power ratings. He’s looking for those sandwich spots. Sure, you can find those sandwich spots yourself, but are you going to scour through, you know, 313 NCAA basketball schedules to find them? It’s what he’s doing before the game tips off in November. He’s thinking, “Okay, here’s a really flat spot. This could be really interesting. Let me write this on my calendar so that it’s here.”           

We’ve got guys that are, you know, particularly in NBA circles, they get great inside information. A few weeks ago, I never knew this. I should have. It made sense as soon as one of our guys said it. Of course, the Pacers bus to Chicago, why the heck would they fly to Chicago, right? I never really thought about that. Well, their bus broke down. They had a flat tire. It took four hours. They walk into the gym and say screw it; we’re not doing shootaround. We’ll see you at game time. Guess what. They got the doors blown off, okay. They just were pissed off and annoyed. Those types of things, you’re not going to get all the time and those are the types of things, I think, that do still provide a value, but I am genuinely curious to see where the industry is going.           

We see a lot of different sites, they provide different analytics, whether it’s KenPom or Bart Torvic for college basketball or you hear from the shot selection guys. You have to kind of be able to dissect your information. I like to think that that’s what our handicappers at WagerTalk do for those guys that have full time jobs that can’t do this full time, because all of that data collection really is a full-time job. They’re going to give you your information and you can pick and choose. “Do I want to play all their stuff? Do I only agree with them here? Do I only agree with them there?”

We have a really great customer service team and I give them tons of kudos. We always like to take care of people, and if there’s somebody who’s unhappy, we always are, like, “Here you go. Here’s a refund or you can join up with another guy.”

So, I like to think that we are the, least tout-y of the touts, right? When it comes to a gambling scale, we only allow guys to do 1% to 5% of your bankroll. You should never bet more than 5% of your bankroll. We don’t allow them to have more than four five-percenters a month, because that would be 20% of your bankroll. There are limitations in place.            

I don’t sell picks. Have I sold picks? Yeah, absolutely. Have I thought about selling picks after the Action documentary? I definitely did. Plenty of guys made a lot of money selling picks, but I said, “No, I’m having a really good time. I’ve got plenty of media gigs where I give these all out for free.” 

DR: Because of the way you have been in the media, you have a little more freedom than your typical over-the-air network has had in terms of the way you cover sports and look at gambling angles. So, Fox started out covering betting, then launched its own book. Barstool starts out talking about betting, launches its own book. Now they’re both out just as ESPN has launched its own proprietary book. What are some of those traps or obstacles that come with trying to be both the media and the book that maybe even the companies just can’t avoid, because of how these business and the laws are set up?

KS: That’s really interesting. I’m not actually even sure what happened with Fox Bet, but I can tell exactly what happened to Barstool. They have been called the pirate ship for a reason. They are unapologetically, just completely out of their minds and say whatever they want with almost zero repercussions. Well guess what? Gaming is going to deal with 40 different states that are going to have something different to say about it. As somebody who grew up in the Nevada gaming world, Nevada has its own sets of rules and regulations.           

I sat in on three different Massachusetts gaming meetings, and I was appalled by some of the ideas and some of the things that these people who have no idea about gambling outside of a casino in regard to sports betting are upset about a can’t-lose parlay with Big Cat, but in the same breath, now we have Rece Davis saying the same thing on ESPN. That’s why I called a spade a spade. I know a lot of people were like, oh, you’re being ridiculous. I said, “When it comes to the law, it has to apply to everyone. And if it’s got to apply to some, it’s got to apply to all.”           

That’s literally what I think happened with Penn. They said, “Oh, shit. We maybe should have looked into this company a little bit more.”           

I think maybe they thought Dave was just going to ride out his contract and ride off into the sunset. I remember there were so many times with Penn where I’m like, “hey, guys, if you want me to go do this event, if you guys want me to do this, you guys want me to do that” and Dave’s like, “you’re not using my talent to do X, Y, and Z. This is what we agreed to.” And I’m like, “oh, okay, I volunteered, but if you don’t want me to do that, okay.”           

I’m guessing something similar happened at Fox, right? They had the show, they were in L.A., they, you know, had Todd they had Clay, they had Sal, and they were the first ones to launch. I did Fox in the Westgate Superbook in 2014, and it was a really fun show.  I’m guessing that it doesn’t always equate to players though, so it didn’t always equate to hard dollars. When you’re spending millions upon millions of dollars to acquire customers – only the certain kind of customers though. Don’t forget, they don’t want the sharp customers. It’s tough to do.           

WagerTalk is based out of Michigan. If there’s something that I want to bet, I can just make a call like, “hey, you have an MGM account and like, can you beat this?” It takes like five seconds because they have everything at their disposal versus in Nevada, which doesn’t allow DraftKings or FanDuel and probably will never. Then you’ve got Massachusetts that seems to be the strictest. New Jersey still can’t bet on college games. There are a couple other states that are now going “we may backtrack and rewrite the law and not allow you to bet on college games.” So, there’s a lot of hoops. There’s a lot of things to navigate, especially in multi-state situations. And I think that’s ultimately that’s what’s going to be the hardest for some of these operators, because you may be able to offer something in one state but not in another, and then you’re going to piss people off. It’s a muddy situation to try to navigate. 

To learn more about Point-To-Point Marketing’s Podcast and Broadcast Audience Development Marketing strategies, contact Tim Bronsil at [email protected] or 513-702-5072.

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Ryan Clark is Ready for ‘The Pivot’ to Grow with Channing Crowder, Fred Taylor and Fanatics

“We want to be a place where you can just be yourself and you can love yourself and truly tell your story and show people who you are.”

Derek Futterman

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Ryan Clark
Courtesy: The Pivot

Answering a call from Emmy Award-winning producer Alicia Zubikowsi, Ryan Clark learned of a potential new media venture in a niche space. Zubikowski had produced the I Am Athlete podcast for nearly two years, which rapidly proliferated in size, scope and prominence. A financial dispute among the colleagues, however, led to the departures of Channing Crowder and Fred Taylor from the roster, along with Zubikowski, and they branched out on their own to actualize a new vision. After speaking with Zubikowski, Clark met with Crowder virtually and evinced compatibility that compelled him to become involved in the project.

Less than two years later, The Pivot Podcast has quickly amassed notoriety and prestige within sports media. The athlete-driven podcast contains weekly conversations with contemporaries and luminaries alike, to talk sports, music and entertainment. Clark, Crowder and Taylor possess an evident rapport and retains the audience while encouraging prospective listeners to hear the genuine endeavor.

“We felt like there was some synergy there, we thought we could do some good things and we decided to give it a try,” Clark said. “I had already been doing my own podcast that I was funding myself, editing myself and cutting promos myself just because I understood what the space was and I knew that that’s where a lot of media was going, and at the time I didn’t have a partnership or anyone kind of showing me the way, but I was like, ‘These people have already been successful.’”

Since its launch in the winter of 2022, The Pivot Podcast has amassed over 158 million views and 870,000 subscribers on YouTube alone. The show has welcomed guests across a variety of professions, some of whom have included Caleb Williams, Snoop Dogg, Gayle King and Travis Kelce. During its time in circulation, it has made an indelible impact on the landscape and recently agreed to a multi-year partnership with Fanatics.

Through the deal, The Pivot Podcast will feature Fanatics’ verticals surrounding commerce, betting, collectibles and events, and the Fanatics Sportsbook garnering the title of the “official sportsbook” of the show. Additionally, the program will be part of company events such as Fanatics Fest NYC and its annual Super Bowl party.

“Luckily for us, it’s been such a blessing,” Clark said. “Some of the stories we’ve been able to tell, the people we’ve been able to work with and have as guests on the show, and then obviously now having an opportunity to partner with Fanatics and be a part of Michael Rubin’s team and sort of head their media division, especially when you’re speaking of Alicia and what she’ll be able to do, it just makes so much sense.”

Fanatics itself had inked some deals in the sports media space over the last year, including agreements with Bleacher Report and Overtime, but they were largely under the aegis of merchandising and/or live events. The company also hired Ed Hartman as its chief strategy officer in media, trying to discover content that fits various key business sectors. For The Pivot, retaining creative control and autonomy over the content was essential and being involved in other ventures added more value to the proposition.

“To be a part of those things and bringing those things to the world, but also an opportunity to showcase the athletes and entertainers that are part of the Fanatics family – and I think that’s a different and a bigger opportunity than any podcast has ever had with any partnership, and that is why it was important for us to find the right partnership,” Clark said. “And if I’m being honest, our producer has turned down multiple deals saying that she believed that this was the one before this was ever even a thing that Michael Rubin was talking about.”

Reaching this point required hard work, consistency and confidence that The Pivot would ultimately resonate with audiences and establish a rapport in the space. Luckily for Clark, he had a viable fallback plan in that he was working at ESPN as an NFL analyst, a role he had positioned himself to attain while he was still an active player.

During his career, he had worked on 93.7 The Fan hosting a radio show from a hibachi restaurant in Pittsburgh and also appeared on local television. Clark played 13 years in the NFL as a safety and won a Super Bowl championship as a member of the Pittsburgh Steelers in the 2008 season.

Although Clark had been told as a player that he had a chance to thrive in sports media, his formative years in the business broadened his understanding of the landscape and how to achieve success. Upon retiring from the NFL, he signed a multi-year agreement with ESPN to appear on NFL Live, SportsCenter, ESPN Radio shows and additional network programming.

Over the last several years, he has been a consistent part of NFL Live. Clark explained that the show contains underdogs who have crafted chemistry that has coalesced into an on-air product and meaningful friendships. Laura Rutledge, Dan Orlovsky, Marcus Spears, Mina Kimes and Adam Schefter work with Clark and blend their football knowledge and expertise with entertainment.

“I could see how much work they all put into their craft, and I respected that, and then once you get that respect and you start to work together, now you get to know the people,” Clark said. “You get to know about their kids, you get to know about their home life, you get to know about what makes them tick and what makes them themselves, and then we care about each other.”

As members of the show watch NFL games every week, they remain in constant communication through a group chat. Additionally, Clark ensures that he is actively listening to what his colleagues say on the air so he can disseminate informed, substantive opinions that play a part in the overall product.

“The smartest of analysts understand what they have to be on each show based on who they’re working with,” Clark said. “I think you just also have to be versatile enough to do that. You have to know when you’re on NFL Live, that show is so heavy X and O; that show is so heavy, ‘Let’s educate – let’s talk about the things that are important in ball, even if they aren’t the most popular things.’”

Starting last season, Clark was added to Monday Night Countdown as a studio analyst as part of a revamped iteration of the program hosted by Scott Van Pelt. Joining Clark as analysts on the show were his NFL Live colleague Marcus Spears and incumbent analyst Robert Griffin III. While there were some memorable moments both in studio and on site throughout the year though, Clark felt that the show struggled to capture an essence on the air.

“I think the show is just hard because it’s sort of like rolled over the entire infrastructure and changed the people, and it happened so late that I don’t think we ever got an opportunity to find our voices on that show, and we tried to work through that throughout the season,” Clark said. “….I think last year was a learning experience where if I’m being really honest, we did bad TV sometimes, which was new for me because I felt like I haven’t done bad TV in a very long time, and it was embarrassing for me because I put so much time into it.”

Former Philadelphia Eagles center and Super Bowl champion Jason Kelce is joining the show and was formally introduced this week. During a charity golf outing this offseason, Clark had a chance to meet Kelce and learn more about him as a person while also answering questions about ESPN and the sports media business.

“I told him to be himself because being himself is what got him here,” Clark said. “He’s a first-ballot Hall of Famer in my opinion, so he has so much knowledge, experience and wisdom that people will crave, and he can give it to them uniquely with his personality, with his honesty [and] with the openness and vulnerability about who he is. Other than that, he’s going to have to learn.”

Akin to Clark hosting The Pivot and working at ESPN, Kelce hosts the New Heights podcast with his brother, and will now be joining Monday Night Countdown on ESPN. Clark anticipates that Kelce will be a huge addition, referring to him as the “hottest free agent ever,” and hopes to grant him longform chances to express himself on the air. Being on the show for a second season, however, nearly was not a reality for Clark amid an expiring contract at ESPN.

“I was gone,” Clark said. “I wasn’t considering – I was done. Normally they extend your contract until it gets done most times. I was out – my contract had ended.”

Clark took part in discussions with other people in the business, some of which included having his own show and organizations starting networks around him. Throughout the process, he was cognizant about the relationships and memories he had built at ESPN and was appreciative for various personalities speaking up for him, including Mike Greenberg and Stephen A. Smith. In the end, Clark signed a multi-year extension with the network that implemented a raise and additional responsibility while also continuing his other projects.

“Obviously my family is the NFL Live crew,” Clark said. “Scott Van Pelt and I probably share one of the most memorable nights in television when Damar Hamlin went down. And so those relationships were things that I didn’t want to leave unless there was a good enough reason to leave, and I don’t think that’s just money.”

Clark started hosting Inside the NFL last season on The CW, a storied sports franchise that presents highlights, analysis and interviews every week during the NFL season. After spending approximately four decades on HBO and subsequent years on Showtime and Paramount+, the program moved to broadcast television for the first time. Clark conceptualizes his role as a point guard who is able to score when necessary and successfully facilitate his colleagues Jay Cutler, Chad “Ochocinco” Johnson, Chris Long and The Pivot co-host Channing Crowder.

“I think that was the hardest adjustment with Inside the NFL initially was like, ‘Okay, how do I set these guys up for success while still doing something I’m really good at, which is analyzing football?,’” Clark said, “and it’s taken some time to really sort of find a space for it, but I think I did find that on Inside the NFL.”

In working on The Pivot, Clark built relationships organically through conversations surrounding strategy, content creation and lifestyle. One episode in particular that stands out to him is when the show interviewed former NBA forward Michael Beasley where he opened up about his mental health struggles and hardships he has endured throughout his life. Furthermore, he talked about struggling to find the right people and explained that everyone stole from him except his kids. Clark, Crowder and Taylor sympathized with Beasley and offered him assistance, underscoring the unscripted, genuine nature of the show.

“Everybody wants The Rock to be able to come on their show and talk about his battles with depression, but we also want Kevin Hart to be able to come on the show and invite him to nudist camp too,” Clark said. “We want to be a place where you can just be yourself and you can love yourself and truly tell your story and show people who you are. And I don’t necessarily know if it’s distinctive in effort or goal; I think it’s been distinctive in execution, which, in the end, is what we deliver to people.”

Through the new partnership with Fanatics, Clark looks forward to continuing to take part in candid conversations and storytelling on The Pivot while continuing to thrive in his work with ESPN and The CW. As someone who attained a successful NFL career after signing as an undrafted free agent, he maintains a mentality built on an indefatigable work ethic and resolute dedication towards his professional endeavors. Once the show signed the partnership with Fanatics, it had an opportunity to interview Tom Brady, who discussed topics including his experience being the subject of a Netflix roast and the lessons he learned playing in the NFL.

“Not everybody understands Tom Brady, right?,” Clark said. “Who knows that story? Who has ever lived that, ‘I’m the greatest to ever do something’? But everybody has understood what it’s like to struggle; what it’s like to doubt yourself, right? And so we bring them that story, and in bringing them that story, we talk about the things that Fanatics is doing and the ways that they are now moving in the sports world.”

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Christopher ‘Mad Dog’ Russo Making the Most of His Resurgence with the Help of ESPN

Far from a close-minded fuddy-duddy. He is an open-minded observer of sports, one of the greatest of all time.

John Molori

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Screengrab of First Take on ESPN with Chris Russo
Screengrab from ESPN/First Take

The true essence of Christopher ‘Mad Dog’ Russo, Version 2024 can be found in the open to the May 15 edition of First Take on ESPN.

In the aftermath of the Knicks defeating the Pacers in Game 5 of the Eastern Conference Semifinals, superstar showstopper Stephen A. Smith opened the program with an emotionally joyous soliloquy lauding his favorite New York basketball team. Smith was jubilant, ebullient, and thrilled.

The segment ended with Smith walking over to panelists Russo and Kendrick Perkins and hugging them in glee. After the show’s open, the Knick rapture continued, that is, until “Mad Dog” was let out of the kennel.

Russo brought things back down to earth, predicting that Indiana would win Game 6 of the series. He then went through a mental historical timeline of the Knicks choking in playoff games at home. This level of historic context is largely lost on modern sports fans, many of whom believe that nothing existed before LeBron James or Tom Brady.

Russo’s beautiful dose of reality ticked off the jovial Smith but set the discourse on a more levelheaded road. Russo is a talking history book, and let’s face it, not everybody likes history class. The difference, however, is that Christopher Russo lived this history, and indeed, made history himself. A 2022 National Radio Hall of Fame inductee, he has uniquely entertained sports fans for more than four decades, becoming one of the most memorable and imitated personalities ever.

He created Mad Dog Sports Radio on SiriusXM in 2008 and headlines the channel with his popular Mad Dog Unleashed show. In addition, he hosts the daily High Heat program on MLB Network. Still, it is one of Russo’s earliest and most recent gigs that set him apart.

Beginning in 1989 and for the next 19 years, Russo and Mike Francesa hosted the landmark Mike and the Mad Dog afternoon driveshow on WFAN radio in New York. It was a ratings mammoth and ensconced Russo as a stone-cold sports media legend.

I am going to make the case that Russo’s latest incarnation as a First Take Wednesday regular is just as significant. It has exposed a whole new audience to the Russo experience. On a more basic level, it is just really special to see a classic radio guy like Russo welcomed into the most progressive and popular sports talk show on the air right now.

Kudos to Stephen A. Smith for making Russo a regular on his program. You can tell that Smith, author of an historically significant media career himself, truly respects those who came before him and blazed the trail. In fact, to a certain extent, Smith is a media offspring of Russo. They both possess riveting personalities, unquestioned bravery, and on-air dominance. Like or dislike, agree or disagree, these are two men who must be listened to and respected.

With Max Kellerman’s 2021 exit from First Take, I was doubtful as to what would happen to the program. My worst thought was that Smith would bring in a bevy of co-hosts who would bow to his greatness – like Jerry Jones’ Cowboys’ coaching hires since Jimmy Johnson. Thankfully, Smith went in the other direction. Russo has the same cache as Smith, so there is no hero worship. He says what he feels and talks straight – real talk in a colorful and exciting manner.

As the Knicks discussion continued, Smith wanted to tap into Russo’s New York sports sensibilities and emotion asking Russo if he felt Madison Square Garden shaking during the Knicks’ Game 5 win. It didn’t work. Russo responded that at 65 years-old, he has been in the Garden for many big games and then cautioned Smith to take it easy with the Knicks.

He again harkened back to New York’s less than sparkling history in big games and menacingly joked that it is his job to “spoil Stephen A’s fun.” Russo then spectacularly took the air out of the building with an ominous What If asking what the Knicks would do if it came down to a Game 7 and the game was tied with the clock winding down.

Russo is also self-deprecating. When host Molly Qerim asked him for a prediction on the Nuggets-Timberwolves series, Russo said that he predicted that the Bills would blow out the Giants in Super Bowl XXV – the famed Scott Norwood missed field goal game. Qerim, who does an excellent job in controlling Hurricane Christopher, acknowledged the obscure reference.

While Russo has a database of past stats and stars, he is not lost in history. In fact, on this edition of First Take, he made a bold statement that the Nuggets’ Nikola Jokić has the greatest offensive skill set of any center in the history of the NBA. These are not the words of a stodgy curmudgeon whose mind cannot be changed.

Russo is an astute observer of our games. He sees greatness and gives that greatness credit. Far from a close-minded fuddy-duddy. He is an open-minded observer of sports, one of the greatest of all time. His opinions are not to be chided. They are to be listened to and appreciated.

During First Take’s Quick Takes segment, Russo ably put his encyclopedic knowledge to use. The question posed was whether the Celtics or Lakers are the greatest franchise in NBA history. Russo’s analysis was spot on and long overdue. First, he discounted the Minneapolis Lakers’ five titles as part of the pro-Lakers argument. He also cited the Celtics’ overall dominance when the two franchises have met in the NBA Finals over the decades.

Lastly, he remarked that the Celtics have had four eras of greatness: Russell in the 1960s, Havlicek-Cowens in the 1970s, Bird in the 1980s, and Pierce-Garnett in the late 2000s, while the Lakers have only two: Magic-Abdul-Jabbar in the ‘80s and Shaq-Kobe in the 2000s. It was the best analysis of a longtime debate.

In a debate about Bronny James and his NBA hopes, Russo again was the voice of reason giving a very realistic analysis of why he is not a top pro prospect. It is clear that Russo has nothing to prove, nobody to impress, and no apple to polish. He made his bones years ago, and his takes are refreshing and objective.

The cherry on top of Russo’s First Take sundae was his What Are You Mad About? segment. Viewers tuning into this part of the program are no doubt wondering who the hell, and at times, what the hell they are watching. Russo pushes the limits of his angst, heart rate, blood pressure, and decibel level picking apart several news items from the week in sports. At times, he closes his blurbs screaming to the heavens, “May God strike me down!”

In this particular segment, he went off on late NBA playoff start times, the intrigue surrounding the 2024 NFL schedule release, and his distaste towards the vulgar humor in the Tom Brady roast. Russo gets up close to the camera and goes off in a boisterous way. It is simultaneously fantastic and frightening.

In his last piece on the roast, Russo looked into the camera and yelled to Brady, “How stupid can you be!” This is the same question I will pose to anyone who dismisses Russo as an out of touch old guy. This cat is no curmudgeon. He is a killer. Elderly? No, epic. Bygone? How about straight up bad ass. That is Christopher “Mad Dog” Russo, Version 2024.

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How to Renegotiate Your Annual Sports Radio Advertising Contract

Reducing expenses within an annual radio agreement takes a strategic negotiation and budget management approach.

Jeff Caves

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Graphic that shows two people negotiating
Graphic Courtesy: Soject.com

If you are a small to medium-sized business, there is no doubt you are facing rising costs, and making ends meet is a top priority. Sometimes, that means cutting expenses on things you have committed to via contract, like a 2024 annual radio advertising agreement with level monthly payments. You are on the air each month and appreciate the value of advertising consistently. You understand the necessity to maintain a market presence within the budget you laid out last year. You negotiated a win-win contract and are happy with it. However, with your costs spiraling to deliver your services, cost-cutting measures have become critical for financial viability in the long term and better cash flow in the short term. You are now tasked with the need to reduce expenses wherever you can, and your sports radio advertising is next on the list. The station doesn’t want to lessen your committed budget. It’s time for strategic negotiation and decision-making. Here are some effective strategies to accomplish this objective while keeping your annual budget intact:

Pricing and Rates

Initiate negotiations on pricing and rates for ad spots with the radio station. They know where they have more demand than supply and could even make more money by freeing up some of your commercials to be sold to other clients, sometimes at higher rates. This is typically during the weekday drive time periods; you probably got an annual rate for your commitment. If the station is willing, you could move into off-peak nighttime buys or weekends. Off-peak hours typically come at a lower cost and can still reach a substantial audience, enabling you to stretch your budget further. Give the station 30 days to see if they can accomplish this, and if not, go to plan ‘B.’

Longer Commitments

Consider committing to a longer-term contract, like a multi-year agreement, to potentially lower your monthly cash commitment. Maybe you could move off $2,000 per month from July to December and move it to the first six months of 2025. Emphasize your dedication to maintaining a consistent advertising presence over time, which can incentivize the radio station to continue the partnership.

Frequency and Unit Length

If the station allows you to reduce the monthly budget, focus on maximizing frequency by strategically choosing the length of ad units. Instead of running only thirty and sixty-second ads, opt for :15 slots to increase frequency without exceeding your budget. Shorter units are more cost-effective per spot and can deliver well-known messages repeatedly.

Budget Reallocation and Trade

Explore avenues for reallocating funds within your annual budget to optimize expenses. For instance, negotiate a reduction in the monthly budget and allocate the saved funds to months where your cash flow is strongest. Having a payment schedule that matches your cash flow will give you the best chance to meet expenses. Furthermore, explore opportunities for service or trade to offset your monthly bill, leveraging resources you have already paid for that may match up well with what the station needs.

Reducing expenses within an annual radio agreement takes a strategic negotiation and budget management approach. Concentrating on pricing, rates, contract length, frequency, and budget reallocation can keep your station relationship intact, honor your contract, and increase cash flow.

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