As the sun takes its respite on the East Coast, Mark DeRosa is wide awake and locked in on the slate of Major League Baseball games across the country. There are usually no more than 15 games occurring on a given night, and he makes sure to select two or three contests on which to place extra emphasis and scrutinize ahead of MLB Central the next morning.

Once the clock strikes around 10 p.m. EST, he is on the phone with members of the production team at MLB Network to share his observations and deliberate potential topics. In addition to preparing for conversations with MLB Central co-hosts Lauren Shehadi and Robert Flores for the next morning, he also works to compile a nuanced, precise breakdown. Reaching the final product that airs on television in front of the display in Studio 21, however, takes collaboration and synergy from several different departments.

The breakdowns DeRosa presents are not always centered on clear highlights, but rather the granular details that affect causation with the potential to shift an outcome. In combining quantitative and qualitative means of study, he has established a reputation as a sharp baseball luminary with a production mindset.

“I always feel like my breakdowns and my analysis to be deeper than what you’re going to get in a highlight package,” DeRosa said. “There might be a pitch in the fourth inning that didn’t get called. There might be a stolen base in the fifth inning that no one saw that doesn’t show up necessarily in the box scores or plays that don’t show up necessarily in the box scores that I know have massive effects on the way the manager manages the rest of the game [and] the way the players attack the rest of the inning, so that’s how I try and approach it.”

DeRosa played college baseball at the University of Pennsylvania before embarking on a 15-year MLB career. The journey across the big leagues took him to various organizations, including the Atlanta Braves, Texas Rangers and Chicago Cubs, and firmly entrenched at a confluence of varying approaches tailored towards a common broad end goal. Communicating with perennial All-Star sluggers such as Chipper Jones, Albert Pujols and Michael Young added and refined his philosophy on hitting. DeRosa aims to convey these esoteric principles to viewers of MLB Central as he dissects the game.

“I just try and take you inside the mind of the great players,” DeRosa said. “I was a role player for a long time in my career, and I sat on the bench and had a firsthand experience with Hall of Fame pitchers and Hall of Fame managers and just kind of picked their brains throughout the course of the early parts of my career to try and formulate a plan and understand what they were thinking.”

When MLB Network revealed that it was going to be debuting a daily morning show on its airwaves, DeRosa was not sure how the logistics of such an endeavor were going to work. Matt Vasgersian had experience in the timeslot working as a co-host on Hot Stove during the offseason, which in turn allowed DeRosa to feel that he could stick to his baseball analysis in its early stages.

“When that red light’s on, I’m no different than when it comes off,” DeRosa said. “Everyone who’s ever played with me knows that. My heart’s in the right place; I’m not jealous; I’m proud of my career.”

Lauren Shehadi Rises Through the Ranks

From the onset of MLB Central, DeRosa has worked alongside Lauren Shehadi and observed her deft knowledge and professionalism. Shehadi remembers being present at Oriole Park at Camden Yards when Baltimore Orioles shortstop Cal Ripken Jr. played in his 2,131st consecutive game, breaking the historic games-played streak of Lou Gehrig. A 20-minute standing ovation and significance of the feat catalyzed her to find a way to stay around the sport in perpetuity.

In order to pursue her dream, Shehadi attended the University of Florida and immediately began to hone her craft. While attending school, she worked as an overnight editor at Suncoast News Network and also had production responsibilities, including listing birthdays and the winning lottery numbers. During her formative years in the business, she accidentally gave the wrong person a $250 lottery winning, an aberration that caused her to think she was not cut out for the role. Despite the blunder, Shehadi persisted and worked with the outlet’s sports director to create content for her demo reel, which she then sent to hundreds of broadcast outlets around the country.

“It’s so interesting because I was a waitress when I was young, and I always feel like you need to be a waitress to understand how to be a good guest at a restaurant,” Shehadi said. “You have to know what that waitress or waiter is doing and what they’re going through to understand how to be a kind guest at a restaurant. I feel the same way in television production.”

Working as a co-host on MLB Central is a role Shehadi considers a labor of love, but it took repetitions and a willingness to improve to be considered for such an opportunity. Despite being nervous to relocate to Minot, N.D. to begin her job at KXMC-TV, the outlet’s news director, Jim Olson, turned out to be an invaluable mentor. He helped her inject personality into the newscast while keeping the stories focused on the subject matter.

As a weekend sports anchor and weekday sports reporter, Shehadi would travel to capture footage from local sporting events and bring it back to the station. There was one instance when she carried her camera into Saskatchewan, Canada to film a junior varsity ice hockey game and then drove back, always ensuring her station wagon was fueled.

“You had to fill up your sole tank of gas because it was that cold,” Shehadi recalled. “If your car stalled out, you’d die of hypothermia, so you had to have full gas wherever you went. You had to be aware [and] you had to plug in your car at night.”

As Shehadi became more experienced in the industry, she cultivated versatility and built her skillset across different platforms of dissemination. While working for CBS Sports as a contributor to its website and college sports network, she learned how to convey information in a compendious manner and express her opinions.

From there, Shehadi secured an audition for MLB Network and perceived that she did not know as much about the game as was necessary. Because of this, she safeguarded against oblivion and studied every player, manager and ballpark around the league. In developing this erudition, she also combatted initial apprehension about speaking while listening to a talkback feed in her ear during a show.

“Why is Freddie Freeman so good at the plate? Because he’s able to slow the moment down,” Shehadi said, “and I think as broadcasters, that’s what you try to do. I think in my early years at MLB Network, I wasn’t able to [do that], and I work on it every day still.”

Displaying propensity and intelligence for baseball is not only achieved by accruing knowledge, but also a cognizance of when to ask questions. Shehadi considers herself a casual baseball fan and contributes to an environment that encourages open conversation and dialogue.

When former first baseman Carlos Peña referenced high-probability swings during his analysis, she thought she knew what it meant but was not entirely certain. Since she played softball and studied the game, she assumed that there could be someone watching from afar who may not know as well. As a result, she decided to ask Peña to confirm what entailed the concept he was discussing.

“I was just literally crossing my fingers in hopes that I wouldn’t end up on YouTube where it’s, ‘See, this girl that hosts a baseball show doesn’t know what this is,’ and he said, ‘You know, it’s a good question,’” Shehadi recalled. “I thought, ‘Okay.’ He said, ‘The bat stays through the zone [for] a longer time,’ which is what I thought it was. But you don’t always know, and the beauty of our show is that he can answer that question and someone at home learned something that day.”

Akin to DeRosa, Shehadi watches several baseball games simultaneously every night using her phone and television. Once the new day commences, she views Quick Pitch to see the rest of the action, reads articles on the league website and studies the network’s research packet. At the same time, she considers the discussions and perceptions made about players, some of whom come into the studio for live appearances.

Robert Flores’ Road to the Show

When Matt Vasgersian became the new play-by-play announcer for Sunday Night Baseball on ESPN, the MLB Network morning program named Robert Flores as the new co-host of the show. Flores, who formerly worked at ESPN, had been employed by MLB Network since 2016 hosting a variety of programming. DeRosa stated that he has brought a different element to the show through his love of the Houston Astros, leverage of social media and humorous witticisms. 

“I feel like Robert Flores kind of ties it all in a bow with his ability to host and his one-liners, and I just think [MLB Central] gives the fan at home everything they would need with a smile on their face,” DeRosa said. “They laugh, they learn and they can enjoy a nice breakfast and a cup of coffee and enjoy the visuals.”

Flores began his career while at the University of Houston, working as an associate producer within the KHOU sports department. From the beginning, he could ascertain the speed of the newsroom and adapted his workflow to fit in the breaking-news environment. Being amongst industry professionals within a top-10 marketplace prepared him to transition to Monroe, La. out of school with limited resources in a smaller locale.

From there, Flores moved to Waco, Texas to serve as the sports director for KWTX-TV where he was responsible for managing personalities under a departmental aegis. He worked in the same role later in Austin, Texas at KEYE-TV while also continuing to garner repetitions as a reporter. The experiences within his formative years in the industry helped shape him into a professional with the sagacity and foresight to plan ahead and optimize a roster of on-air personalities and production personnel.

“It’s managing people from it’s simplest things like scheduling to the more complicated, intrapersonal and taking into considerations what others’ needs and what their wants are as well and trying to kind of fit it all under the same direction of what you want your sports department to be and things like that, so it was a great experience,” Flores said. “Again, I met so many great people along the way and so many that I’m still friendly with and keep in touch with every now and then.”

Flores endured challenges within the industry when he lost his job in 2004 and ended up being out of work for six months. Four years earlier, he had lost his father and was trying to combat the trauma associated with both outcomes.

As he continued the job search, Flores began to think about alternatives and considered exploring the real estate and insurance industries. He remembers asking his wife if he should change career paths, and she urged him to give the process more time and remain patient. Everything changed when his agent called to deliver the news that ESPN was interested in hiring him for a job on the network, and he was able to inform his son minutes later when he arrived home from school.

While Flores enjoyed his time anchoring SportsCenter and contributing to other programming at ESPN, the era was different in that social media was not embedded within the fabric of modern society. Although he joined MLB Network in 2015 and was known by its viewers across programming, there existed a risk that moving to MLB Central could cause him to suffer from imposter syndrome. After all, Flores was expecting harsh criticism upon his debut on the show; however, he entered the role unfazed and focused on delivering for the audience.

“In today’s society especially, I think fans are more apt to not like something, and I get it,” Flores said. “Matt Vasgersian was very popular [and] remains very popular with our fanbase… and I know there was some skepticism about me joining the show. I saw all of the, ‘Where’s Matty V?’ tweets and, ‘This guy stinks,’ and, ‘Get him off,’ and I understood it.”

In the five years that Flores has been part of the show, he has let his personality flourish and shared different ways he interacts with the game, including through playing MLB The Show video game series. Playing the simulation game over the years has helped him become more familiar with major-league rosters and prospects, granting him additional context and a different lens through which to talk about the league.

“To be fair, I do like to shoehorn dropping my Twitch handle and my Facebook page where I do my video game streams,” Flores explicated, “but I think it’s kind of looked at as kind of if I can get a joking eye roll from Lauren or from someone that says, ‘Hey, way to make the ‘reference’ to your gaming channel,’ I think it’s part of my charm, and I say that tongue-in-cheek.”

The Morning Commute

The composition of MLB Central as a studio show contrasts many of its counterparts in that it utilizes more hosts than analysts. Shehadi and Flores both view their role to serve as point guards to set up DeRosa for success in disseminating his opinions and insights.

“I think for me, the beauty of what we do is the fact now that the chemistry between the three of us is so strong,” DeRosa said. “I honestly know how to get Robert going, I know how to get Lauren going and vice-versa that I think the people at home – although I’m the former player that’s going to give the opinion – I still think that they’ve built this relationship at home with the three of us.”

The show also champions diversity and inclusivity, inspiring the next generation and trying to serve as role models. Flores is of Mexican-American descent and is honored when aspiring professionals reach out to share their gratitude for his work and how he represents what is possible. As a woman in the industry, Shehadi is aware of the misogyny and intransigence that can be faced, but she knows that there is respect for her work and that she belongs. Everyone on MLB Central is accepting of one another and attributes part of its success to strong chemistry.

Studio 21 is somewhat like Grand Central Station, especially since it houses multiple studio programs in addition to MLB Central, some of which include MLB Now and Quick Pitch. For Shehadi and DeRosa, it is one of their destinations on the travel itinerary, which involves both of them taking multiple flights per week.

Every week following the Tuesday morning show, Shehadi flies to Atlanta, Ga. to host studio coverage for MLB on TBS with Curtis Granderson, Pedro Martínez and Jimmy Rollins. Whereas MLB Central will focus on all 30 teams, MLB on TBS studio coverage primarily discusses teams featured within its Tuesday night doubleheader on its Pregame and Closer editions of the show. While Shehadi is in the TNT Sports studio, she is watching every game around the league and feels the most prepared for MLB Central the following morning. The key through it all is endurance and stamina, but she does not take the multifaceted role for granted.

“I feel so blessed to be able to do it, and it’s not lost on me that I get to host both,” Shehadi said, “so I just pray for no delayed flights and pray that I get everywhere on time.”

Similar to taking an extended road trip as an MLB player, DeRosa flies to the New York metropolitan area every week to be in studio for MLB Network. After the Friday morning show though, he boards a flight to return home to spend time with his family and coach his son’s baseball team. While he is away for the weekend, he still remains connected to the show by reviewing previous episodes and finding areas where he can improve, akin to a baseball player reviewing film.

“I like it when we go off-script occasionally – when we’re laughing; when things get a little funny at times and then we’re able to rein it in,” DeRosa said. “So I think for me, the idea of a good show to be honest with you is if I can get the people behind the cameras to start laughing, I usually think we’re doing something right.”

Flores believes that DeRosa is one of the most talented studio analysts in sports television and does not receive as much credit as he deserves in this regard. In formulating and constructing his breakdowns with the understanding of what will stand out to viewers with fluctuating interest levels and aptitude towards the sport, DeRosa tries to appeal to everyone. Last spring, he served as the manager of Team USA during the World Baseball Classic and had a chance to foster deeper relationships with several star players such as Mike Trout, Paul Goldschmidt and Mookie Betts. In turn, he discovered more about their personalities and work ethic.

“I thought Paul Goldschmidt – he is, he’s a silent assassin – but when I gave my first meeting the first day we met as a group, as soon as I finished, he asked me if he could address the team,” DeRosa recalled. “I did not expect that, so I walked away with a completely different mindset of [who] Paul Goldschmidt was.”

Beyond the Box Score

DeRosa, Shehadi and Flores provide authentic commentary about the topics at hand within a casual environment geared towards viewers with varying levels of proficiency and experience in baseball. The program attempts to spotlight as many different MLB teams as possible on the show and recognize the parity and emerging young talent within the game; however, there are signature teams discussed more often because of recent success. While MLB Central is situated in the mornings, the segments and topics are not proprietary to that daypart and could effectively function in different areas of the schedule.

“I think there’s a very fine line walking the three kinds of tenants if you will of informing and providing context and entertaining,” Flores said. “I think you’ve kind of got to be very careful not to do one more of the other, but I really think that our show is portable, I really do.”

Although MLB Central does not implement live callers from consumers akin to sports talk radio, it still finds ways to interact with the audience and impart sentiments of conviviality and revelry. Whether it be through poll questions or replies to a segment earlier in the program, there is a recognition and respect for consumers watching across multiple platforms.

“We have a bunch of really great viewers who have been with us for almost a decade, and we constantly highlight them on X,” Shehadi said. “We constantly put their tweets on the screen, and some of them we disagree with all the time.”

DeRosa, Shehadi and Flores hosted their 750th episode of MLB Central last summer and all remain committed to the program. Everyone leaves their ego at the door and approaches the show in a manner resembling a player arriving at the ballpark for a game.

Concurrent with rules changes across Major League Baseball that led to augmented attendance, greater offensive output and a hastened pace of play, MLB Central remains aware of the latest innovations in sports media and looks to continue innovating within the dynamic landscape. Although there is an early wake-up call to arrive at the studio and prepare beforehand, DeRosa, Shehadi and Flores are able to effectuate a morning show of which they are proud and hope to continue for years to come.

“I love what we have both on screen and maybe more importantly what our show unit has off screen,” Flores said. “It’s a very collaborative effort. We have so many talented men and women behind the scenes in our research department; in our control room; from the producer to the director to our assignment desk, [which] plays a vital role in booking guests. It’s just everyone pulling in the same direction. I can honestly say it’s the most enjoyable professional experience I’ve ever had.”

If you have prospects who are open for business between Midnight and 5 am, why not have them make it worthwhile and help them develop an advertising strategy? They might be surprised how inexpensive it can be.

Many companies operate 24/7:

– Convenience stores, gas stations, and truck stops.

– Fast food chains like Taco Bell, Jack in the Box, and McDonalds.

– Hospitals and Emergency Care clinics.

– Hotels, motels, and grocery stores.

– Airports, bus depots, and cabs.

With an effective marketing strategy, “it’s gonna be all right on the night shift.” Here are some insights and tips to give these prospects to help them attract and retain customers to their 24/7 business:

Understand the Night Owl

At night, customers seeking services or products often prioritize convenience, speed, and availability. Sometimes, price isn’t the controlling factor, nor is it even the best quality they seek. Make offers and go to market with these needs to better cater to your target audience and keep them returning for more.

Advertise: Digital Billboards

Digital billboards are great for visibility, especially at night when there’s less competition for attention. Consider strategically placing advertisements along busy freeways or nightlife hotspots to capture the attention of passersby and promote your business’s offerings and operating hours. If you can buy :15 ads on Times Square in NYC for $40, you may be shocked at what you will pay locally for rotating ads from Midnight to 5 am. 

Radio Ads on the Cheap

Radio is a powerful medium for reaching customers during the late-night hours. Larry King was America’s most listened-to-talk radio program in the late 80’s. For 16 years, he broadcast live between Midnight and 5:30 am from coast to coast. Select radio stations with programming tailored to your target audience’s preferences and air ads during peak nighttime listening hours. Pop music stations for night clubbers at 2 am or News Talk for late-night drivers wanting to stay engaged. Give incentives to overnight listeners to visit your business NOW. While the audience may only be 10% of the daytime crowd, so are the prices. And let’s face it, if they are driving and listening to the radio, that’s your #1 prospect! Expect rates at most stations under $25 per commercial in major cities and less in other areas. Promote late-night specials, highlighting convenience and speed of service. If you are a hospital, airport, or bus company, brand your business with the overnighters, reminding them you are open when they need you.

Mobile Digital Advertising

Target potential customers in the vicinity of your business during late-night hours. Use geotargeting to deliver ads to mobile phone users in high-traffic areas like concerts, ballgames, or nightlife districts. Drive foot traffic right through your front door. Promote time-sensitive offers or exclusive late-night deals through mobile ads. Don’t expect a price break, though, when purchasing them.

Easily Monitoring KPI’s

Regularly monitor the performance of your efforts and adjust as needed. Your late-night business is probably way less than daytime, and tracking key metrics such as foot traffic, sales, and customer feedback will be easier. If an offer is working on your radio campaign, look into buying more stations and cut back on areas that don’t work. Apply the 70-20-10 rule to your ad budget.

With lower ad costs aimed at the audience who makes staying open late worth it, you can be ringing in the profits on the night shift.

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.