Digital Social Hour
How Poker Builds Billion-Dollar Business Connections | Jeff Gross DSH #1125
Sun, 19 Jan
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Discover how poker isn't just a game—it's a gateway to building billion-dollar business connections! 🃏💼 In this episode of the Digital Social Hour, Sean Kelly sits down with poker pro Jeff Gross to uncover jaw-dropping stories from the poker world. From playing cash games with Michael Jordan to insane prop bets like living in a Bellagio bathroom for 60 days and biking from Vegas to LA, this episode is packed with valuable insights and unbelievable moments. 🤯 Learn how poker fosters networking, sharpens strategy, and creates life-changing opportunities. Whether you're a poker fan or curious about its impact beyond the felt, you won’t want to miss this! Watch now and subscribe for more insider secrets. 📺 Hit that subscribe button and stay tuned for more eye-opening stories on the Digital Social Hour with Sean Kelly! 🚀 Join the conversation and let us know: What’s the wildest poker story you’ve heard? 🗣️🎙️ #philgalfond #pokerbusinessconnections #livepoker #highstakespoker #pokerstrategy CHAPTERS: 00:00 - Intro 00:27 - Jeff Gross Influence on Poker 04:59 - Specialized Recruiting Group Insights 05:56 - Tattoo Cost Discussion 09:58 - Best Prop Bet Ever 11:05 - Bill Perkins Overview 12:30 - Jeff's Poker Career Update 12:51 - Tour of Jeff's Miami Studio 13:57 - Jeff's Future Plans in Miami 15:44 - Nathan's Role 15:58 - Would You Rather Scenario 16:59 - Outro APPLY TO BE ON THE PODCAST: https://www.digitalsocialhour.com/application BUSINESS INQUIRIES/SPONSORS: [email protected] GUEST: Jeff Gross https://www.instagram.com/jeffgrosspoker SPONSORS: SPECIALIZED RECRUITING GROUP: https://www.srgpros.com/ LISTEN ON: Apple Podcasts: https://podcasts.apple.com/us/podcast/digital-social-hour/id1676846015 Spotify: https://open.spotify.com/show/5Jn7LXarRlI8Hc0GtTn759 Sean Kelly Instagram: https://www.instagram.com/seanmikekelly/
Chapter 1: What is the craziest prop bet story shared?
What's the craziest one you've heard? In the Bellagio, someone had to live in a bathroom of the Bellagio for, it was 30 days. That's a true story. You can look it up. It's a Google YouTube that. There's a video of it. It was on live stream. How did he sleep? Hey, he was in a bathtub. He'd call room service. Wait, there's a bathtub? He was in a bathroom.
Oh, I thought you meant the public one. No, of the Bellagio. That's still disgusting. It's crazy, yeah. All right, guys, we're at Celebrity Poker Tour. We got Jeff Gross here and he's the guy who got me into poker. So it feels like a full circle moment actually right now. It is funny to see you at the Celebrity Poker Tour backdrop and everything. So you're now embracing poker.
You get it. You've played one of these and you like it. Absolutely. I remember going on your show like five years ago and you asked me what I know about poker and I was like pretty much nothing. Now poker and podcasting. You're doing all the fun stuff. Absolutely, man. You got any fun celebrity poker stories?
Oh, yeah. I mean, I've been playing 20 years, so there's definitely some that I can say, some I can't. But I would say I have a lot of great gambling stories as well from prop bets. That's something that's kind of not normal to, I'd say, the outside poker world. So I could give a couple of those. I'll say one celebrity thing, which I've obviously mentioned before, and Michael Phelps.
So I met him at a poker table in 2006, and then we did become roommates. So in 2008 till 15, lived together. He loves poker. Actually, we were here yesterday, and he was doing an event for Ferrari with Global and global poker and he's like a poker addict, right? He just loves it. He loves the game, the competition.
So that was cool to live with him for eight years during sort of the peak of the Olympics and everything that was exciting. And I'd say the other cool, notable celebrity thing would be playing cash game with Michael Jordan at his house. It was in Park City and something I'd never seen before was only hundred dollar bills. So there was no chips.
It was like, you're playing, but do you, but AC and it was like, you know, $2,500 clips, 10 grand wraps, thousand dollar things. And it was literally like, you bet, like I bet 4,000 and you got, you know, you got to count it out and throw the clips. And that was only cash on the table. And that eliminates the credit problem, right? You know, cash, no credit, no problem. That wasn't the case.
You had to pony up cash and sit down and, and, uh, I actually have another story about that in Park City. This Barry Baker, who was the reason we were there. Phil Ivey came once, was in town, and won a poker game. And they let him go to his game. And he went to a... Phil Ivey needed cash. They said, hey, no problem. You can buy in. They let him not have credit at this game.
But he was like, you know what? No, I don't know you. I like to pay and go. He's like, where's the local bank? He went to the bank. He went in. It's Park City. It's Utah. A little bit, you know, mostly white dominant. And they hit the alarm like he was robbing the bank. So... That's a true story. He was on my podcast. A little racist.
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Chapter 2: How did Jeff Gross get into poker?
No, what happened? So Brian Rast, he got bet if he could ride, and I might mess the exact details up, but it was essentially that he could ride from Vegas to Dan's house in Los Angeles in like 24 hours. And I think he could use a recumbent bike. And he got like six to one or seven to one odds. A lot of our friends were betting. I think Rast ended up making... like a million or something on it.
And yeah, there was a lot of people had action on it and Bill Perkins and Dan Bilzerian bet against him. They got like an RV and were trailing him and they did this whole thing. And like, there was one point where Rast was like, couldn't move. And they had like a doctor like drive out. They found him the GPS, like random in the Hills. And he like took a, they like shot a shot.
He did it, it's a pretty famous one. There's all kinds of these crazy bets, but Dan did that, right? He trained with Lance Armstrong and he did one himself, but it was like longer time and he could have a little more time to train. But Rast was one of the more famous ones and he actually got paid to do like the PCH, I think Pacific Coast Highway. And one guy bet him,
gave him crazy odds and then two days later bought out for like 400k so he got him like a million and then bought out and just paid him he didn't have to do it so there's all these type of bets like that wow but yeah have you ever bet on a prop bet i've been in a lot of prop bets like random ones you know no alcohol for a year i i there's a famous one about a tattoo where i got a offered a price for a tattoo i don't want to say the exact amount but it might have been north of half a million to get a tattoo on and it was a mystery tattoo so that that happened and you got it
Yes, I did get it. I didn't know you had a tattoo. Yeah, that was a long 2013. And yeah, you got to look that one up. But I won't confirm the amount. But it was a wager healthy. And it wasn't really a wager. It was more like a dare. And I don't have any tattoos. And it was basically, Bill Perkins was like, how much would you have to be paid to get a tattoo? And I said a number.
Didn't think he would say yes. And he just snapped it off. We were in Amsterdam. And then the next day I was there and I had to like call my friends and family. I was kind of like, hey, is this like, this is kind of crazy. I didn't think you'd say you would do it and you did it. And then it went through and I got it. Damn.
I mean, when you got money like that, what's a couple hundred thousand to them? Yeah.
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Chapter 3: What are some wild celebrity poker stories?
They pulled it off? What weight did they meet up? It's like 100, or let's see, 91, 320. It might've been like 180 or 200 or something, 190. So the guy actually, I think, I want to say that the one guy, Matt might've been like 110 pounds. They had to get like to 180 and 350. Holy crap, and they're brothers? How are they so different? 110 and 150?
Jamie was over 300 pounds, and I have a picture of it. We were on Twitch in St. Thomas, and someone on the chat threw out this idea. We were live on Twitch. This was like 2016 or 17, and someone was like, well, how much for these guys to do it? And Bill was there. A lot of Bill Perkins props. He loves these. Yeah, he was there. He was like, all right.
And then they threw out the odds, and they did it. So yeah, that was probably one of the cooler ones. And that actually had been... Man, this is actually, we could use- They keep coming. No, there's two more great ones. The best one I ever heard, and you can look this up as well. I think his name is Svatni. He's like Swedish or Danish.
And he said, how much do you have to get paid to get breast implants as a man? Oh my gosh. And so this is also true. $100,000, he got the implants, C-cups, and C-cup breasts as a man, and it was one year he had to have them. He got paid, and the best part is he, after a year, he enjoyed them. He didn't take them out. He said that the women loved them.
It was like a thing, and he still has them today. That's true. At least as of five years ago. It was probably 20 years ago. That was one of the original prop bets I heard, and I know it's real for sure. It's verified. It's been talked about scene. So that's a crazy one. And there was one other, I was just thinking of that. I forgot, but there's C cops as a man. Yep.
That's no joke. So he has to wear a bra. Allegedly. I don't know. I have no idea. I've never, but I, you know, that is one that is like a gambling lore. Wow. Yeah. There's another one I just thought of. There's a lot. There's a lot. You could do a show on like the, just the profits alone. That's so nice. Bill Perkins is hilarious. He's the best. Die with zero. Has he been on yet or no?
No, I'd love to get him on. But that book's great. I've read that book. I saw a clip of him. He had to catch a private jet flight. He bet like 500K and left. He didn't even see. Oh yeah, he was all in at the lodge in Texas. Doug Polkin, he's got that game. And he literally went all in and left and left. He was bluffing, I think, or he maybe had the, I think he was bluffing.
He was bluffing and he ended up winning. And the guy folded a game, like stuff like that. That's savage. He's, he's got a lot of. I mean, poker's probably just a side quest for him. That's not even like.
Yeah, he does it for, he's actually someone that he's gotten really good. He put a lot of work in his game and he's actually like a really good player. I used to, I used to go to Houston twice a week when I, from like 2013 to 15, played in a pretty high stakes cash game and I'd stay with Bill. And he, he, he was one that said he actually lost a fair amount of money in poker originally.
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