Digital Social Hour - How Poker Builds Billion-Dollar Business Connections | Jeff Gross DSH #1125

Episode Date: January 19, 2025

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: [e-mail] 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/

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Must be 19 years of age or older to wager. Ontario only. Please play responsibly. If you have any questions or concerns about your gambling or someone close to you, please contact Connex Ontario at 1-866-531-2600 to speak to an advisor free of charge. BetMGM operates pursuant to an operating agreement with iGaming Ontario. There's a video of it. It was on live stream. How did he sleep? He was in a bathtub, he called room service. Wait, there's a bathtub? He was in a bathroom. Oh, I thought you meant the public one.

Oh, no, of the belayas. So that's still disgusting. It's crazy, yeah. 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've 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. That's awesome. 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 like 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 2015, 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 a hundred dollar bills. So there was no chips. It was like, you were playing Badoogie Badesi. 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. 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 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, you know, 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 his park city. It's Utah a little bit, mostly white dominant.

And they hit the alarm to like he was robbing the bank. So that's a true story. Very big story. He was on my podcast. Little racist? Yeah, this was back in the day, like maybe 15 years ago. But that's a true story. Very big. What? He was on my podcast. A little racist? Yeah, this was back in the day, like maybe 15 years ago. But that's a true story. Dude, that's crazy.

Yeah, I'm sure some of these home games get insane. Yeah, there's a lot of home games are different than the casino. There's a lot of credit. There's a lot of gambling. It gets a little wild. And for sure, there's been some interesting stories. And I'd say the prop betting is a little more,

that's where that's like the more exciting stuff, where you get some kind of like random bets come up, bike riding bets. I don't know if you heard about the Bolzarian bike ride bet. 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 that action on it and Bill Perkins and Dan Buzarian bet against him.

They got like an RV and we're trailing them 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 they had like a doctor drive out. They found him in the GPS, like random in the hills. And he like took a, they like shot a shot. Holy crap. 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 do, you know, 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 you got him like a million and then bought out and just paid him. You 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, no alcohol for a year. There's a famous one about a tattoo where I got offered a price for a tattoo. I don't want to say the exact amount, but it might've been north of half a million to

get a tattoo. And it was a mystery tattoo. So that happened. And you got it? Yes, I did get it. I didn't know you had a tattoo. Yeah, that's, 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, there

was a, it was a wager healthy and it was, it wasn't really a wager. It was more like a dare. 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, how much would you have to be paid to get a tattoo? And I set a number. Didn't think he would say yes. And he just snapped it off.

We were in Amsterdam. And then next day, I was there. And I had to call my friends and family. I was kind of like, hey, this is kind of crazy. I didn't think he'd say he would do it. And he 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 him? Yeah. Can't say the amount exactly. I won't confirm it. I never did. Looking for the ultimate online casino experience? Step into the BetMGM Casino app where every deal, spin and goal brings Las Vegas excitement into the palm of your hand.

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please contact Connects Ontario at 1-866-531-2600 to speak to an advisor free of charge. Bet MGM operates pursuant to an operating agreement with iGaming Ontario. Bet MGM is an official sports betting partner of the National Hockey League and has your back all season long. From puck drop to the final shot, you're always taken care of with a sportsbook born in Vegas. That's a feeling you can only get with BetMGM, and no matter your team, your favorite skater, or your style, there's something every NHL fan is going to love about BetMGM. Download the app today and discover why BetMGM is your hockey home for the season. Raise your game to the next level this year with BetMGM, a sportsbook worth a celly,

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Specialized Recruiting Group is ready to find the talent you need. So go to srgprose.com right now to get started. That's srgprose.com. Specialized Recruiting Group, a tailored approach to hiring. Some numbers thrown out there and it was a good wager, yeah. I wonder how much I would,

because I have no tattoos and I don't want them. So I wonder how much someone would have to pay me to get one. Be careful, if you throw a number out. I'll't want them. So I wonder how much someone would have to pay me to get one. Be careful. Throw a number out. I'll park it right here. What are you talking? What's in your neighborhood?

What do you think? Dude, it'd have to be at least six figures. Because first of all, there's a lot of new research on the ink. So I'd have to get like a holistic tattoo. Because the old ink is actually bad for you. You're saying I might have a problem? I don't know what you got, bro. It's a very tiny.

I see people with full body. Yeah, yeah. It's like a little, I got like a very small. That's leaching in your skin. Right. So. Yeah, it can't be great. Can't be the best.

Yeah. But I'm sure a small one wouldn't hurt. Listen, if you put a price out, I know there's a lot of gamblers out here. I'll do a little fund rate, a little group pool. I don't like that it's random, though. Like, you don't get to pick what it is. Well, no.

I mean, that's in negotiation. That particular one was random. It couldn't have been like, you know, something insane, but it was, it could be pretty much anything. Okay. Other than, you know. If I had to pick, it'd probably be my girl or like her name or something simple. If you put a price out, I'll crowdfund out here.

I'm pretty sure we get it done today. That's hilarious. Dude, that's legendary. Yeah, the poker guys, you guys are different. There's some really wild profits. Like, I mean, I'm just, those are just a few that people I know are a part of, but there really is some like, you know. What's some really wild profits. Like, I mean, I'm just, those are just a few that people I know are, were a part of, but there really is some like.

What's the craziest one you've heard? Well, the, the, in the dark or the, in the Bellagio, someone had to live in a bathroom of the Bellagio for, it was 30 days, 60, 60. That's a true story. You can look it up. It's a Google YouTube that there's, there's a video of it. It was on live stream.

How did he sleep? Yeah, he was in a bathtub. He'd call room service. Wait, there's a bathtub? Like he was in the, he was in a bathtub he'd call room service. Wait, there's a bathtub? Like he was in a bathroom. Oh, I thought you meant the public one. Okay. No, of the Bellagio.

So of the room. In the room. In the room for 30. That's still disgusting. It's crazy, yeah. Yeah, that's gross. Like 30 days and this was probably like 2010. There was actually a way sicker one recently.

You could Google it as wealth and get like video and the whole thing. And they did it where the guy, I think his name was Rory. And there was another guy and they were in Australia maybe. And they bet like 100,000 that he could live in a dark room, like no light for a month. Like kind of crazy, isolated like in there.

He could go out anytime he wanted if you want to give up. But he bet like it was 100 grand, if I'm not mistaken. And I think they let him out after like three weeks or they bought out for like 60 or 70K. Like they're worried, you know, health reasons, like being in a hole for 30 days with no light. Like it sounds crazy, but yeah. So there's stuff like that.

People kind of just dare each other. My buddy Hook, he did a two week fasting bet where he had like no, he didn't eat, didn't have any food for two full weeks. And he did that pretty, pretty crazy. Bill Perkins, he's like a master prop. Oh, there's like a master prop. There's been liposuction ones.

What? I'm sorry, there's been body fat ones where people have got liposuction at the end to try to get it done, like get down to 8% or 10%. Those are very common. I'll give you one more, actually. I just thought of one more, which I actually had a big bet on, was the Staple brothers, Jamie Staple

and Matt Staple, two poker streamers, good friends of mine, they brothers. And Jamie, again, going gonna get the weights wrong, but one was like 350 pounds and one was like, let me see if I don't mess this up, might've been like 120 or something like that. And they had to get to the exact same weight within a pound.

So not even, they couldn't even cross. They had to weigh in within one pound of each other after like a year. And they got like 50 to one odds on it. And that was a crazy bet. That was on a site, Poker shares. They post that 30 to one. I bet it like, I got like eight different prices at 30 to one, I got some at 50 to one.

I got like all these odds and then they did it. They pulled it off? What weight did they meet up? It's like a hundred and, let's see, mine need one 320, might've been like 180 or one, or 200 or something, 190. So the guy actually, I think I want to say that the one guy Matt 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 have been like 110 pounds.

They had to get like to 180 and 350. And they're brothers? How are they so different? 110 and one? The guy was like 300. 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 like 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 built a lot of bill Bergens proper he was like yeah, he was there He's like, you know, all right, and then they threw out the odds and they did it So yeah, though that was probably one of like the cooler ones and that actually had been oh I man This is actually we could use like he's coming. There's two more great ones the best one

I ever heard and you can look this up as well, I think his name was Svartny, he's like Swedish or Danish, and he said how much you have to get paid to get breast implants as a man. Oh my gosh. Yeah, 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, a year grand. 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. What? It was like a thing and he still has them today. No. That's true. At least as of year, five years ago,

it was probably like 20 years ago. That was like one of the original prop bets I heard. And I know it's real for sure. Like that is, it's like verified. It's been talked about seen. So that's a crazy one. And was like one of the original prop bets I heard. And I know it's real for sure. Like that is, it's like verified. It's been talked about seen. So that's a crazy one. And there was one other I was just thinking of that I forgot. But there's.

Sea Cops as a man. Yeah. That's no joke. That's like. So he has to wear a bra. Allegedly. I don't know. I have no idea.

I've never. But you know, that is one. That is like a gambling lore. Wow. Or there's another one I just thought of. There's a lot, there's a lot. These are, I'm telling you, you could do a show on, like the, just the profits alone.

Bill Perkins is hilarious. Cause I've seen- He's the best. I was zero. Have you been on yet or no? No, I'd love to get him on. Oh, we got him. 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 see- Oh yeah, he was all in. At the lodge in Texas at Doug, Doug Polk. He's got that game and he literally went all in and left. And he was see. Oh yeah, he was all in at the lodge in Texas. Doug pulled in, he's got that game and he literally went all in and left and 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 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 him. 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 go to Houston twice a week from 2013 to 15, played in a pretty high stakes cash game, and that's David Bill. And he was one that said he actually lost a fair amount of money in poker originally. He said it's probably one of the best things he's done,

because as an investment, just from the relationships and business and things he's done, he got a ton out of it. But now he's spent time, and he's studied, and he's actually, if he wants to play well, he knows really exactly what to do. He's tough. He's a good player.

But then again, he's busy. He's like, there's times you're on your phone or you play a turn. He plays a turn or something. He's like not fully focused. But like, yes, he knows like really up to date on solvers and done deep work on the game. And that's a smart guy.

One of my best friends, amazing guy. And again, Dai was zero. I got to plug in. You got to have him. He will definitely come on. That's a dream guess. One of my best friends, amazing guy. And again, Dai was zero. I got to plug in. You got to have him. He will definitely come on. That's a dream guest. He's in Vegas, fair amount. And yeah, sure.

He'll definitely come on. You still playing often? You still streaming? So I do a show once a week called Gigi Millions. It's a 10K buy-in on Sunday. It pauses. And then Tuesday is the final table. And they then do play to a winner.

So I have a guest every week with me on that. That's like for Gigi Poker, that's every Tuesday. And then I do podcasts, still do a lot of that. Shout out to Nathan Cherenek, the videographer. And now in Miami, so we built a studio and do a lot of work there. And I try to do live. I think it is a lot better live,

but of course sometimes still do them online. But I enjoy the podcast. I haven't quite put the formula like you where I'm doing like a ton at a time. And I would like to do that, right? It's fun. And I think that that's something in Miami. There's a lot of people, there's interesting people.

I could definitely do it. But it's like, yeah, I respect the process. My clip guys here, I'm gonna introduce you guys. Max is here, shout out to Max. And the studio in Miami. So I filmed all over the country. I film in a new city every month. That studio in Miami is God-tier. I mean, it's the best quality in Miami, so I filmed all over the country. I film in a new city every month. That studio in Miami is God dear.

I mean, it's the best quality in Miami by far, but also one of the best in the country. Cause dude, it's a struggle getting good studios. I filmed in Phoenix, I filmed in LA, I filmed in like Salt Lake in New York and the quality is just ass. Yeah, I appreciate it. I appreciate it.

It is cool. It's more like a, it's got not just a studio, it's more of like a, it's a cool place to kind of just relax. You could bring people there, hang out. And you know, we do games there, poker games, and it's got not just a studio, it's more of like a, it's a cool place to kind of just relax. You could bring people there, hang out, and you know, we do games there, poker games, and it's fun, man. So yeah, hopefully you make that like a quarterly stop

where it's coming and doing it. Oh yeah, well, I might come for Basel, we'll see, but if not, I'll be there for F1 next year. Is, have you been there for either of those? I've been for Basel once, I haven't been for F1 yet in Miami. Was it good last year or this year, I guess? It's awesome.

I think our Basel's like the best time of the year. Oh, is it Basel? Yeah. Oh, my bad. Sorry, that's good clip, Basil. People are going to like that. No, but it's fun. It's a great time and it's F1 and that are awesome. So Miami's got a lot of stuff going on.

Messy's there now, sports are coming. It's really changed in the last four years. Yeah, imagine getting messy on the pod. I'd be nuts. I mean, they put it out there, why not? He's in the neighborhood four years. I'm actually getting messy on the pod. I'd be nuts. I mean, they put it out there. Why not? He's in the, he's in the neighborhood. I wonder how his English is.

It's not his first. You learn Spanish for that. Yeah, I might have to. I would do it for messy. Yeah, I would learn Spanish. Yeah. And Ronaldo. Yeah, that's me. We should do a bet.

We can, who can learn Spanish in a year? Okay, let's do it. I'll, I'll, I'm not, actually, that's not totally fair. Cause I've been doing Duolingo Portuguese. Plus you're in Miami. Yeah. So you got a home field advantage. Give you a little bit of odds, but we can, we can do a bet. Yeah, I'm not, actually, that's not totally fair because I've been doing Duolingo Portuguese. Plus you're in Miami. Yeah. So you got a home field advantage. Give you a little bit of odds, but we can do it better.

Yeah, I would need odds on that because people practically speak Spanish there on the streets. Yeah. And it's like the main language there. If, all right, let me, if Messi was going to be on the pod in three months, what, how much time, what'd you do? Would you cancel everything? Oh, I would dedicate eight hours a day.

I would probably go to Mexico and just walk the streets and like learn it. That's damn, Messi, man. That's a day. I would probably go to Mexico and just walk the streets and like learn it. That's damn Messi, man. That's a lot. Messi's top 10 in the world in terms of like just fame and followers. I mean, I played soccer my whole life. Obviously I agree.

That would be, he's definitely, it's cool to have him in Miami. I actually went to one game and it was a final where they made it last season and he didn't play. And that's like a big sweat because he's getting older and he's messed up. So I still haven't seen him play, which is sort of irresponsible to be in my game.

Yeah, that's a once in a lifetime thing at this point. He's probably only got a few years left. It's crazy because they lost in the playoffs just now. And they won the regular season, the best team out of 30. And then the first round they lost. So I'll go to another round. Like I'm going to go in one of the upcoming games. And then somehow they lost.

Wow, they blew it. They got Swarovski now too. Yeah, they're stuck. They blew it. Damn. Well, dude, it's been fun working with people. Check out the studio and and then somehow they lost. Wow, they blew it. They got Swarovski now too. Yeah, they're stuck. They blew it. Damn. Well dude, it's been fun working with people. Check out the studio and check out your poker stuff. So Miami, you can go to mediagrapher.com

and rent a spot or talk with Nathan there. He, you know, you obviously know Nathan does your man. He is great and he can handle that. And then on my stuff, Jeff Gross podcast, Jeff Gross poker, YouTube and all socials. So yeah, it's great to see you coming up and killing it. And this is, I get a kick out like the Celebrity Poker Tour. This thing is awesome.

It's amazing how they have everyone here. Like so many people have been, I've seen or known in poker and it seems like it's growing, getting bigger, better every time the prize pool is bigger. And would you rather be here or there? Do you have a little- I'd rather do this than play. Just cause I'm all about getting that content in. So.

Yeah. Well. Playing's fun too. Yeah. Big, big crowd. I talked to Mori who is, you know, Mori's all doing amazing content here and they've been like, like poker go, they've given it a ton of praise. People I talked to like, wow, this is literally like, this is for poker. What I think is one of the best things that could happen. You have all these, these top influencers and people that are then streaming on their channels, people that aren't as into poker maybe or don't know about it, they're getting awareness to it. So yeah, whoever's idea it was, I assume like a Blake

Wynn who started it, founded it, you know, whoever actually like saw this through it's genius and it's I think it's probably one of the best things going in poker at the moment to get new people in and new audiences. Absolutely. Yeah, we'll link your stuff below. We'll link Celebrity Poker Tour below. Thanks for watching guys. Peace Bet MGM is an official sports betting partner of the National Hockey League and has your back all season long from puck drop to the Final shot you're always taken care of with a sportsbook born in Vegas That's a feeling you can only get with bet MGM and no matter your team, your favorite skater or your style There's something every NHL fan is going to love about Bet MGM

Download the app today and discover why Bet MGM is your hockey home for the season Raise your game to the next level this year with Bet MGM, a sportsbook worth a celly and an official sports betting partner of the National Hockey League. BetMGM.com for terms and conditions. Must be 19 years of age or older to wager, Ontario only. Please play responsibly. If you have any questions or concerns about your gambling or someone close to you, please contact CONNECT ONTARIO at 1-866-531-2600 to speak to an advisor free of charge. BetMGM operates pursuant to an operating agreement with iGaming Ontario.