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. 

Matt Jones, founder of Kentucky Sports Radio, put on a clinic this past week on how to cover a sports story and keep your fans engaged. If you wanted the latest information on what was happening with Kentucky head basketball coach John Calipari resigning, Kentucky’s replacement search and the eventual hiring of Mark Pope, you didn’t have to go much further than Matt’s X account, @KySportsRadio.

While others may have been first to report certain parts of the story, Matt was on top of it all, and if there was new news, Matt would share it. Then he would generally give an opinion or two, some information or background and when necessary, special content to address a topic as a group.

I am not a Kentucky or Arkansas fan, but I am a fan of John Calipari. I like the “characters” in the sports world, and he is certainly one of them. In my very first management job, I was hired as the Program Director for WHBQ in Memphis. Cal was coaching the Memphis Tigers and I was introduced to him at a Memphis Grizzlies game. I spent about 20 minutes with him, and you would have thought I was a major recruit he was after (I’m 5-7, over 200 pounds so it wasn’t that he was confused). Turns out he had been trying to get some of his assistants a paid radio gig and although it didn’t end up going anywhere, that 20 minutes made me a fan.

So, I had some interest in the story, and I happened upon Matt’s first post which came at 8:42 p.m. on Sunday April 7:

A couple of minutes later Matt posted that nobody on the Kentucky side was confirming anything. A few hours later he posted more from the reporting coming out of Arkansas and then he announced their radio show the next day with Ryan Lemond and Billy Rutledge would go an extra hour.

A few minutes later he posts, “Calipari has informed Kentucky that he is negotiating with Arkansas, according to Matt Norlander.” That post received just under 700,000 views and was shared almost 800 times. At 9:43 p.m., one hour and one minute after posting about the news for the first time, Jones writes, “Twitter space in 10 minutes.”

I can count on one hand how many Twitter Spaces I have taken part in, but I clicked on it more to see how many others were on it. When I joined there were 14,000 people tuned in and Matt would later post they had 19,000 tuned in at once, on Twitter Spaces, on a Sunday night at 10:15 p.m.

Later, Jones would post that he thinks the show the next day “might be the biggest show we have ever done.” At almost midnight he wrote, “I can’t sleep, not gonna lie. The next 48 hours are gonna be wild.”

And he wasn’t kidding. The search for the new coach, the recruits, the portal, the lists of replacement names, the videos from Calipari and his wife, the video of Cal pushing the stroller and walking the dog, the prospective new coaches dropping out (Scott Drew stayed in Waco, Texas for goodness sakes!), the shock of Mark Pope’s name rising to the top and then the eventual hiring of Mark Pope, the press conferences. Holy moly.

And while all of this was going on, Matt Jones was posting and talking about his opinions, hunting for information, writing blog posts, doing interviews, responding to the Kentucky fans, creating extra audio content and keeping everyone in the loop on all of the fallout and aftermath.

I was exhausted keeping up with it, I can’t imagine how Matt must feel.

And what it made me think of is this; if you are a manager of sports media talent, how many of your people would have put in the effort Matt Jones put in and continues to put in on this story?

Matt kept his audience informed, gave them plenty to think about and continuously provided content and context. He brought his audience behind the curtains when he could, and he tried to answer legitimate questions that came up. He was attacked, at one point I believe being blamed for anything bad that has ever happened to Kentucky basketball.

And in the end, when a lot of fans, Matt included, were a bit disappointed when they found out Mark Pope was the guy, they worked through it together. Matt flat out said he was not happy with the hire at first, but now they had only one choice as a fan base and that was to support the decision and the new coach. Pope’s press conference was a sold-out event at Rupp Arena.

Programmers and talent, I encourage you to look back at Matt Jones’ X account timeline from April 7 to today. It’s a blueprint for how to cover a major story and bring your audience along for the ride.

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The Best Thing I Heard Recently

I really enjoyed the conversation Baltimore’s The Big Bad Morning Show had last week talking about the streaming situation. No. 1 prospect Jackson Holliday was set to make his home debut and the game was one which would be streaming only on Apple TV+.

Rob Long, Ed Norris and Jeremy Conn had an adult conversation about the fact that if you were an Orioles fan without Apple TV+ this one would sting. While they noted it is such a small percentage of baseball games, versus football games, that can end up streaming only, this one game would be one a lot of Orioles fans would want to see.

As they talked through it, they noted it is a younger audience which baseball is trying to target, and you are not going to reach that group on linear television. So, while it may stink for fans for that one game or the few the Orioles might have which are streaming only, the bottom line is this is the direction things are going and you need to get used to it.

As Conn said, “Either get in line or get left behind.”

You can listen to the segment in the last hour of the show by clicking here.

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In Case You Missed It

Sean McManus retired this week from CBS Sports and David Berson took over as the president and chief executive officer. Before he stepped away our Derek Futterman had the chance to talk with him and look back on some highlights of his career, this year’s Super Bowl and a look at what Berson will inherit and how things look for the future.

About the success of this year’s Super Bowl, McManus told Derek, “We far exceeded our sales expectations and budgets. The number that’s been written is $700 million, and we exceeded that – obviously the overtime helped – but I think from the time we came on the air at 11:30 with the Nickelodeon Slimetime show until we went off the air at approximately 10:30, it was an unqualified success in every way. The most-watched television program ever; maybe the best Super Bowl ever in terms of the quality.”

You can read Derek’s feature on Sean McManus by clicking here.

No, the NBA play-in tournament won’t save the league. But that’s not the same as saying it doesn’t matter.

In truth, the PIT, as we’ll call it, has done almost exactly what the league’s owners had hoped it would. It drives up a little interest in the NBA’s product before the playoffs proper begin this weekend. It’s sort of an appetizer for the courses to come.

It also drives a few bucks into the pockets of the league’s broadcast partners, and for Adam Silver & Co., that’s the point, of course. Aesthetics aside, if the PIT wasn’t a moneymaker, we’d never speak of it again, very happily.

This creature, after all, is a bit of a mess. It’s clearly contrived. It was hatched during the pandemic as the NBA tried to figure out how to survive its 2020 bubble summer, which tells you most of what you need to know about the motives.

And it can skew ugly. This week’s offerings featured two solidly sub-.500 Eastern Conference teams, Chicago and Atlanta. Under the NBA’s previous top-8 format, the East’s lowest-qualifying playoff team would’ve been Miami at 46-36. That’s respectable.

But the PIT isn’t about respectable; it’s about spectacle. As this year’s version got underway, there were a couple of tantalizing storylines – only a couple, but that’s all you usually need.

In the West, teams featuring LeBron James and Anthony Davis, Steph Curry and Klay Thompson, Zion Williamson, and De’Aaron Fox were all jockeying for their post-season survival. Why? Because their respective teams were merely okay for most of the season, never great.

But you can see why Silver and the NBA owners favored adding a few more playoff possibles in the first place. Again, going back to the top-8 grid of playoffs past, both the Golden State Warriors and Sacramento Kings would’ve been on the outside looking in. Instead, viewers got a Warriors-Kings elimination game on Tuesday night.

The notion of seeing Curry and his crew go out in a one-game tire fire is generally going to be worth a few eyeballs – and that’s the whole ballgame here. Last year’s six PIT games, broadcast on ESPN and TNT, averaged 2.64 million viewers, a 5% increase from the year before.

That’s how this works. By most estimates, the PIT has added millions of dollars in value for the league’s broadcast partners. You can argue that, depending upon the year, the 7-8-9-10 configuration also heightens interest in the last couple of weeks of the regular season, simply because nobody wants to be relegated to the 9-10 elimination game.

It all matters to a league that, like most sports enterprises in America, is trying to figure out the viewer landscape amid a rapidly changing market. Silver acknowledged as much last fall in an interview with Yahoo Sports, saying that the decline in cable subscriptions “has disproportionately impacted the NBA” because the league’s fan demographic trends younger but the remaining cable audience is older.

“Our young audience isn’t subscribing to cable,” Silver told Yahoo, “and those fans aren’t finding our games.”

There’s no doubt the NBA is addressing that issue as it negotiates with TNT and ESPN, whose rights expire in 2025. While cable options might be cut back, the league has to find a way to expand its reach through a significant streaming partnership. It could be part of the impending ESPN/Fox/Warner platform or something else, but it needs to be easily identifiable and easily accessed.

You’d go a little crazy trying to figure out where the NBA stands in terms of viewership. Its opening night last fall was a bust, but the new in-season tournament was a ratings hit. The league got smoked by the NFL on Christmas Day, enjoyed a huge uptick on All-Star Saturday Night, then played a desultory All-Star Game only to see viewer numbers go up from the year before. (Granted, that was a rise from an all-time ratings low.)

Silver, who’s wrapping up a contract extension that will keep him in the commissioner’s job through the end of the decade, has been warily eyeing the TV numbers for years. He isn’t new to any of the concerns, and he has been forcefully behind both the in-season tournament and this PIT creation, which everyone involved has no problem labeling a blatant viewership ploy.

That’s because, for lack of a crisper phrase, it is what it is. The play-in is every bit as basic as it looks, and it was put in place for no reason other than to expand the playoff field and generate a little extra heat through the schedule’s final few weeks, along with these early days of the post-season.

And it generates millions. For Silver and Co, that’s the end of the conversation.