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Meet the Bettors: Dave Sharapan, The Bostonian vs. The Book

Dave Sharapan should be dead. 

That’s not my opinion. I have nothing against the guy. He seems nice enough.

He suffered a very serious stroke in 2020, during the height of the Covid-19 pandemic. Thank God his daughters were home, like kids all across the world at that time. If they weren’t, Dave’s doctors are confident help would have arrived too late and he wouldn’t be with us today.

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Sharapan’s backstory is rich and it’s deep. Long before he was co-hosting The Bostonian Vs. The Book with Matt Perrault, the Pittsburgh native was learning the gambling business in one of the most unique ways you can imagine. He dropped everything in the late 90s to move to Curacao and help launch an offshore book. The experience set him up to make a life and a career out of sports betting.

In the Caribbean, Sharapan learned to write tickets, set numbers, you name it. Offshore startups kind of require every employee to know everything. The experience made him a coveted free agent when he returned to the States and began looking for work in Las Vegas.

To get from there to where he is now, it required a visit from his father, who passed away years earlier. Sharapan has no doubt that while he was in a coma following his stroke, the two had a conversation. His dad told him that his life wasn’t over and that he needed to trust that his risks and plans were going to work out. 

When he awoke, he didn’t know where he was, but he was ready to get back to work, not just in the gambling world or at home. He was ready to get back to working on making the life he wanted for himself, his wife and their daughters.

Dave Sharapan is in the spotlight this week in our Meet the Bettors series, presented by Point to Point Marketing. The guy has a lot to say about mixing information with entertainment, how much the audience knows about line movement, and anything else that I brought up.

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Demetri Ravanos: Tell me about how the hospital stay changed you. The moment you are released and ready to go home, do you have any thoughts at all about your professional life? Have you had any epiphany at that point about taking all you have learned from working in books and doing guest spots on podcasts and radio and turning it into something more?

Dave Sharapan: I became the mayor of that hospital after I woke up, because I was one of the only people talking. I saw a lot of people that were hurting, a lot of people that were probably never getting out of there. It was the most humbling experience that I’ve had in a long, long time. I sat there and thought, “what am I going to do when I get out of here?” I didn’t know, but I’m going to figure it out.           

So we go downstairs the day I am going home. I hug and kiss each one of these nurses goodbye, take a picture with each one of them because my wife brought my phone so that I was able to take pictures of everything and document it all.           

It was the best reunion I ever had in my life – the hugs, the cries, the tears. Pure joy.           

I’m alive. Alright, what do we do now? I said, “I don’t know, but everything looks different, smells different, sounds different. Let’s just go for a ride.” My wife drove. We went and got a nice steak dinner, and we went home and I said, “I don’t think I’m supposed to go back and book all these tapes and worry about the first half of the Saint Bonaventure game anymore.” So it became a media thing, and I did Perrault’s show on Thursday. The audio of that show is tremendous.           

He was still doing Pushing the Odds. He was one of my first calls when I got out.           

You know, Jess [Sharapan’s wife] was updating everybody. She had my phone, which for five days she’s like, “What am I supposed to tell this person?”           

I said she could tell them I had a stroke, but I’m okay, and that I’ll talk to them next week. She’s like, “Are you sure? Do you need to take time off?” I’m like, “I can’t. There’s no time off. It’s just like the book. Next day there’s gates. You got to show up and work.”           

So I did my show on Thursday, and it was pretty emotional. It was pretty good. It was right then. And I said, “Well, I guess we’re going to try this media thing next,” and I’ve been doing it since. My wife says. You know, “you went into the hospital unable to talk. And since you’ve come out, you haven’t shut up.” 

DR: That’s actually a good jumping off point to something I wanted to ask you, because I’ve watched a few of your different appearances in getting ready for this. You are always you. If you book Dave Sharapan, you’re not getting Dave Sharapan fitting into your show. You are getting a very distinct thing.           

I wonder how many of the younger personalities on gambling Twitter or who came up through various sites get the appeal and importance of character. It’s very clear watching you on MLB Network, watching you and Matt interact on Bostonian vs. The Book, not only are you really into this, but you want people to know who Dave Sharapan is. Do you think people looking to make a go of it in the sports betting media get that you still have to entertain a little bit?

DS: Let me tell you this. I was doing a little podcast on the side called Cash Considerations with a couple other oddsmakers in town, and we were doing it without any media background, without any media guidance, and we were getting more and more and more people listening all the time. Every one of those people that you’re talking about on gambling Twitter, wanted to be on our show.            

I just simply asked them,”You want to be on the show? We’d love to have you,” and it was raw and it was real and it was great.           

I’m in the risk room at the book using Twitter to get information, not to entertain. I needed to know why guys were beating us, the numbers and getting injury information before we were. So, I started to just get on Twitter, just as someone who wanted to be a part of whatever community it was, but it wasn’t really a community. It was more a cesspool. It was just a mix of things that were mostly bad, but there were some good. It was a lot of nastiness.           

The problem with the whole business, and I don’t mean just sports gambling. I’m getting a light speed education in the media business. There’s a lot of ego involved. Everybody wants to be right. I said this in the books for years: the money is just the measuring stick. Everybody just wants to be right. And they want to tell everybody when they’re right, but they don’t tell anybody when they’re wrong.           

The greatest sports better in the history of the world, Billy Walters, will tell you 1% of the people win at this. Well, he’s about right. I’ve taken all of their bets. I’ve been in the books. I’ve seen a lot of these people and that’s where it is.           

I’m living the life every day. I love this business because of the business, but the stories and the characters are really what’s made it for me. I have been blessed to meet so many different people that have come to Vegas to blow it out, to come to Vegas to make a new life.This is one of the most transient places in the world, because people come here with the intention that they are going to conquer sports, or they’re going to conquer poker, or they count cards at blackjack. They have a system for roulette. Oh, okay. Great. The casinos are still open. The books never closed. Right?            

I was doing a hit every single week with Nick Kostos on You Better You Bet and Nick gave me a great piece of advice. He said, “Don’t change. Be yourself. Be authentic,” and it was a great piece of advice at the time.           

I’m telling you what we’re doing. “This is how the book does it. You can pick a side if you like the Steelers minus seven or you like the Browns plus seven, you pick. I can tell you why from both sides, and then I’ll tell you if you really want to know what I’m thinking.           

I took bets almost 20 something years. I never asked why anyone was betting anything. I just make sure the money was good and move the number if we needed to move the number. That didn’t matter to me. A guy’s bet only matters to him, so if you’re talking about it, it has to be entertaining, but it has to be real. 

DR: Tell me about your thought process as you are putting together a rundown. You and Matt are talking about what the show was going to be, or you and whoever you’re going on with are talking about what games it is you want to hit on. What do you think highlights what you do best? Would you rather make room for a game that is an interesting toss up or would you rather talk about a game where you are very confident about your position? 

DS: I’ve been in the book on a Tuesday in July, and have gone, “what would you have to talk about if you had to talk about something today?” and then I’ll look at the board, open up my screen and I’ll go, “Well, this is interesting. Washington Nationals are playing Oakland today.” I could find something interesting about any game and make it a betting opportunity.           

I’ve been in books throughout Vegas for years and had someone come up to me and go, “Look, I’ve never done this before. How do I do it?”.           

I’ll ask, “What are you thinking of doing?”           

“Well, I’m from Tennessee and I want to bet the Titans, but I don’t know how to do it. Should I bet them to win the Super Bowl or the AFC or what?”           

You can bet their season wins over, you can bet to win the division, you can bet them to win each week, so you have a bunch of different options. You can cater advice to the customer.         

So, I think when we do the show like tonight okay, there’s two NBA games. I don’t know what appeal each game has to other people individually. We will talk about them because it’s the event of the day. How much will we sell it? If I don’t have a strong opinion on it, I will say “I don’t have a strong opinion on this, but this is why someone might, or this is why someone would go against that opinion.” Why is the total 205 and a half? “Well, because based on their three previous meetings, the game styled around this number, this is why the number’s this and it might move up. I think, you know if anybody’s going to play this, they’re probably going to play it over.”           

When a guy walks into your joint and says, I want five dimes on the over, you have to respect it. What I learned in the business was when somebody walks in, probably with $20 in their pocket, and they’re betting $10 on over and $10 on the side, that’s actually determining whether they’re eating lunch today. So, you can see it from different perspective. So, when we do the content, we’re trying to talk about what’s important to the audience, not necessarily what’s important to us. 

DR: Do you think, on average, people are more educated about betting as it has become more mainstream, or do you think that because it is more accessible it just means that a higher number of people have just basic knowledge?

DS: I’ve been saying this for a decade. This goes back to, you know, when I even first went to the MGM in 2009. They had the backing of Cantor Fitzgerald and they came here to change the game. You could go back to when, like guys like Richard Shoots and Scottie Scheffler said, we’re going to make all of the information available to everybody at the Stardust. I went to the Stardust once in 1991 and I watched what they were doing. I think that’s probably ultimately what led me back to Vegas, because I was like, “This is so cool. There’s people full of cash, and there’s guys with $5 in their pocket, and they’re both waiting in line to make a play.”          

It’s amazing. The book is a meritocracy. You get what you earn every day.           

Information has never been more prevalent than it is now. The other side of the counter was at a disadvantage back in the day because if you put up a wrong number, you get immediate feedback that second. If you’re wrong again when you move it, you have to find out immediately. Everyone can bet. Not everybody can book. I always say that.           

I think now the information is more even keeled and people would probably be surprised. You know the expression that Vegas knows? I say nobody knows sh** all the time. I mean it! I mean it in life.

I’m telling you, like the amount of tools, the amount of things that you could use to help you either build models, learn algorithms, do all this stuff, it’s all out there. So, I think you have to wade through that cesspool. The good stuff’s all going to float to the top. The rest of it’s going to sink to the bottom. It becomes sedimentary waste at the bottom of the cesspool. So it is better. I’m not saying it’s great, but it is better. But there’s a lot of noise. 

DR: It’s something that I was telling a group of students recently here. I live in North Carolina, and I was talking to a friend’s broadcast journalism class, and we were talking about FOX starting that new basketball tournament in Las Vegas.          

I said, “No matter who you are interviewing with you are tempted to think they are smarter than you. As the NIT is dying, FOX just decided, to start a second NIT. Nobody in any business knows a goddamn thing about what they’re doing.”

DS: Well, it fits. I mean, when you look back at it, that’s kind of a lesson that came out of Covid. Everybody had to stay home. Everybody didn’t have the fancy corner office. I think it was a reset not just for business, but for life. Stay in touch with your family, listen to the people around you and educate yourself every day.          

I mean, I sat in books and have taken bets from everybody. I learned this in Curacao. We didn’t have faces. Everybody was a number. We had to learn who’s betting and who’s winning and why are we not.          

My career path is unique in that baseball is one of my true loves in life. I started in the batter’s box at Yankee Stadium down in Curacao, and when I came to Vegas, I was in Double-A, you know, Midland, Texas. I was like, “what are we doing here?” And it changed. But when CG came, they said, we’re going to change everything. We’re going to get accounts. We’re going to make it like trading on Wall Street. That was their big thing, and they were close. They were very, very close. 

DR: We are now in this time where digital products have to be podcasts. They have to be YouTube shows, they have to work across multiple platforms. So in your mind, as you and Matt are putting a show together, do you think of it as a YouTube show primarily or an audio show primarily? 

DS: We got lucky with having all the right conversations at G2E back in 2021 and a company called props.com said yes. You know, we’ve been telling everybody we can do this for a while, and they said yes. So they gave us an opportunity and said, all right, do it. It’s a show. We’re going to have video. We’re going to have audio. We’re available wherever you get podcasts.

At the time I’m working for Sports Grid as well. I’m on Sports Grid everyday Monday through Friday various roles on various shows. And through the two of us, we came together with being on Sports Grid, a re-air of a TV show every day, on Sirius XM radio 159 every night at the same time. So, they take our live show and they put it on their platforms there. So, we’re both a TV show and a radio show. We’re a podcast. We are on YouTube. We are on Twitter. We put it out wherever you can get it. What we’ve learned is that people consume media on their time, right?

So where we grew up with ‘Must See TV’ on Thursday nights, Seinfeld was on at 9:00 eastern. If you missed it, you either recorded it with your VHS tape and watched it later, or you didn’t know what everybody was talking about at work on Friday. So, now we do the show specifically at the same time every day. We call it the “ish time.” We start at 11:15 Pacific-ish. Sometimes it’s 11:20. Sometimes it’s 11:10.           

Last week, two weeks ago, The Athletic called me and said, “Dave, we want to talk to you about Ohtani. Do you have a couple minutes?” I called Matt and said, “Listen, the reporter from The Athletic wants to talk to me. Can we move back a short time in the show?” He’s like, of course. So we do that.           

It’s everything, but this is our biggest hurdle right now. “What are you guys. Why did you call it Bostonian vs the Book?” We call it that because Matt’s from Boston. I’m from a book. They gave us the logo. Like, it wasn’t some well-thought-out, deep conversation. It was like “We need a name. What are we calling this?”. The guy needed an idea and a name to do the graphics. That was it.           

What I’m finding now is I’m 53 and, you know, had a stroke. I came out of it better. All I want to do is kind of be nine years old again. I love Pittsburgh. Growing up in 1973 was so much fun. The Steelers won the Super Bowl after the Pirates won the World Series. We were the City of Champions. Jack Ham was literally my next door neighbor. I thought this was the greatest thing in the world.           

So now this is why if someone tells me “we want you to come on the show” I say “well, can I wear a jersey? Because I’m just trying to be myself.”          

That’s what our show is. It’s Matt being Matt. It’s me being me. And it’s a community of people that show up at the same time every day.           

Our biggest show of the week every week is what we call Roll Call Friday. The last 15 minutes of the show we acknowledge every single person from every single place that they’re from, by calling out their name in their three-digit area code. We make a number because that’s what we do in life, right? What I do, we make a number. Let’s say 39.5. That many states plus four and a half countries. We have people show up every week from Canada, from Mexico, from somewhere in the Caribbean, because I know guys that are down there that I still maintain relationships with. They watch the show and love it. Some kid shows up every single week from Croatia to watch our show every day in the middle of the night. So that’s what we’re doing, where it leads to, I have no idea.

DR: Yeah. That’s the beauty and fear of digital media, right? It can be anything. 

DS: It really can. It’s a two man show. It’s Matt and I. We’ll do sales calls, we’ll do interviews, we’ll cut the clips, we do the rundown, and we book the guests.           

I’m not really competing with anybody. I’m just trying to do what I’m doing and make it like it’s not the scariest thing in the world. 

To learn more about Point-To-Point Marketing’s Podcast and Broadcast Audience Development Marketing strategies, contact Tim Bronsil at tim@ptpmarketing.com or 513-702-5072.

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Demetri Ravanos
Demetri Ravanos
Demetri Ravanos is a columnist and features writer for Barrett Media. He is also the creator of The Sports Podcast Festival, and a previous host on the Chewing Clock and Media Noise podcasts. He occasionally fills in on stations across the Carolinas in addition to hosting Panthers and College Football podcasts. His radio resume includes stops at WAVH and WZEW in Mobile, AL, WBPT in Birmingham, AL and WBBB, WPTK and WDNC in Raleigh, NC. You can find him on Twitter @DemetriRavanos or reach him by email at DemetriTheGreek@gmail.com.

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