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

Summary

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

Release Date: January 19, 2025

Host: Sean Kelly

Guest: Jeff Gross

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Introduction

In episode #1125 of Digital Social Hour, host Sean Kelly engages in an in-depth conversation with Jeff Gross, a seasoned poker professional and entrepreneur. The discussion delves into how poker serves as a powerful tool for building billion-dollar business connections, exploring Jeff's personal experiences, memorable stories from the poker world, and the intricate relationship between high-stakes gaming and business networking.

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1. The Intersection of Poker and Business

Jeff Gross shares his journey into the world of poker and how it became a pivotal element in his business network.

• Business Connections Through Poker
  • Timestamp [01:17]: “It's probably one of the best things he's done because like as an investment, just from the relationships and business and things he's done, he got like a ton out of it.”

Jeff emphasizes that the relationships forged at the poker table often translate into valuable business partnerships and opportunities, highlighting poker as more than just a game but a strategic networking platform.

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2. Memorable Celebrity Poker Stories

Jeff recounts several high-profile poker anecdotes, showcasing the blend of fame and high-stakes gaming.

• Michael Phelps as a Poker Enthusiast
  • Timestamp [02:16]: “He loves poker. Actually, we're here yesterday and he was doing an event for Ferrari with global and Global poker. And he's like a poker addict. Right.”

Jeff's friendship with Olympic swimmer Michael Phelps illustrates how poker can bridge diverse worlds, fostering deep connections beyond the gaming table.

• Playing with Michael Jordan
  • Timestamp [02:45]: “...playing cash game with Michael Jordan at his house. It was in Park City and something I'd never seen before, whereas only 100 bills. So there was no chips.”

This story underscores the unique environments and unconventional setups that emerge in celebrity poker games, emphasizing trust and personal bonds over traditional gaming elements like chips.

---

3. The Thrill of Prop Bets

The conversation delves into the world of prop bets—unofficial wagers made on various events during poker games—and their impact on the culture and dynamics of the game.

• The Bulgarian Bike Ride Bet
  • Timestamp [03:50]: “Brian Rast, he got bet if he could ride from Vegas to Dan's house in Los Angeles in like 24 hours. And he got like 6 to 1 or 71 odds... he did it.”

Jeff highlights how prop bets add an extra layer of excitement and challenge, often leading to extreme feats and memorable stories within the poker community.

• Tattoo Dare
  • Timestamp [04:35]: “...Bill Perkins, like, how much would you have to be paid to get a tattoo?... I got it.”

This anecdote illustrates the personal risks and commitments players are willing to undertake, further strengthening bonds and adding a personalized narrative to the poker experience.

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4. The Evolution of Poker Streaming and Online Presence

Jeff discusses the rise of online poker streaming and its role in expanding the game's reach and influence.

• Building an Online Platform
  • Timestamp [14:30]: “I do a show once a week called GG Millions. It's a 10k buy in on Sunday... that's like for GG Poker.”

By leveraging streaming platforms, Jeff has created spaces where poker enthusiasts can engage, learn, and participate in high-stakes games, thereby fostering a global community.

• Establishing a Studio in Miami
  • Timestamp [15:14]: “I film all over the country... that studio in Miami is God tier.”

Jeff's investment in high-quality production facilities underscores the importance of professional content creation in attracting a wider audience and enhancing the viewer experience.

---

5. Personal Insights and Experiences

Throughout the episode, Jeff provides personal reflections on his poker journey, the lessons learned, and the future of the game in business networking.

• Balancing Poker and Business
  • Timestamp [13:37]: “It's a lot better live. But of course sometimes still do do them online. But I enjoy the podcast.”

Jeff emphasizes the importance of adaptability and balancing live and online engagements to maintain a thriving poker and business presence.

• The Value of Relationships Over Money
  • Timestamp [13:29]: “He literally went all in and left. And he was bluffing, I think, or he maybe had the...”

Jeff illustrates that while high-stakes games involve significant financial risks, the true value lies in the relationships and trust built over time.

---

Notable Quotes

• “Poker is not just a game; it's a strategic networking platform.” — Jeff Gross [01:17]
• “Prop bets add an extra layer of excitement and challenge.” — Jeff Gross [03:50]
• “The relationships forged at the poker table often translate into valuable business partnerships.” — Jeff Gross [02:16]
• “Building an online platform is essential in expanding the game's reach and influence.” — Jeff Gross [14:30]
• “It's a lot better live. But of course sometimes still do them online.” — Jeff Gross [13:37]

---

Conclusion

In this episode of Digital Social Hour, Jeff Gross illuminates the symbiotic relationship between poker and business. Through captivating stories and personal insights, Jeff demonstrates how the game serves as a conduit for forming lucrative business connections, fostering trust, and creating a dynamic networking environment. The episode underscores poker's role not only as a high-stakes game but also as a strategic tool for business growth and relationship building.

Whether you're a poker enthusiast or a business professional seeking unconventional networking avenues, this conversation offers valuable perspectives on leveraging the game's inherent dynamics to achieve billion-dollar business connections.

---

Listen to the full episode on Digital Social Hour to gain deeper insights into the world where poker meets business excellence.

Transcript

[A]

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[C]

What's the craziest one you've heard in the Bellagio?

[D]

Someone had to live in a bathroom of the Bellagio for. It was 30 days. 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.

[C]

How did he sleep?

[D]

Hey, he was in a bathtub. He'd call room service.

[C]

Wait, there's a bathtub?

[D]

He was in a bathroom.

[C]

Oh, I thought you meant the public one. Okay, so that's still disgusting.

[D]

Crazy. Yeah.

[C]

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.

[D]

It is funny to see you with the Celebrity Poker Tour backdrop and everything. So you're now embracing poker. You get it. You have one of these and you like it.

[C]

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.

[D]

Now poker and podcast and you're doing all the fun stuff.

[C]

Absolutely, man. You got any fun celebrity poker stories?

[D]

Oh, yeah. I mean, I've been playing 20 years, so there's definitely. 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 poke world. So I could give a couple of those. I'll say one celebrity thing, which I've obviously mentioned before. And you know Michael Phelps, so I met him at a poker table in 2006 and then we did become roommates. So in 2008 till 15 live together. He loves poker. Actually, we're here yesterday and he was doing an event for Ferrari with global and Global poker. And. And he's like a poker addict. Right. He just loves it. He loves the game. Very. 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, whereas only 100 bills. So there was no chips. It was like you're playing badoogie bidet and it was like, you know, $2,500 clips, 10 grand raps, 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, and, and that was only cash on the table. And that eliminates the credit problem. Right? You know, no 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 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, they hit the alarm to like, like he was robbing the bank. So that's a true story.

[C]

Very big.

[D]

I'll tell you, he was on my podcast.

[C]

Little racist.

[D]

Yeah, this was back in the day, a long time, like maybe 15 years ago, but that's a story. So.

[C]

Dude, that's crazy. Yeah, I'm sure some of these home games get insane.

[D]

Yeah, there's, 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, little wild. And for sure there's been some interesting stories and I'd say the, 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 Bulgarian bike ride. 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 6 to 1 or 71 odds. A lot of our friends were betting. I think RAs end up making like a million or something, like. And yeah, there was a lot of people had action on it. And Bill Perkins and Dan Bazer bet against him. They got like an RV and we're trailing him, and they did this whole thing. And like, there was one point where rest was like, couldn't. Couldn't move and they had like a doctor, like, drive out. They found him, the gps like, ran him in the hills and he like took a. They like shot a. Shot him. He did it. It's a pretty famous one. There's. There's all kinds of these crazy bets, but, you know, 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 RAS 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 2 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.

[C]

Wow.

[D]

Yeah.

[C]

Have you ever bet on a proper.

[D]

I've been in a lot of prop bets, like random ones, you know, no alcohol for a year. 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.

[C]

And you got it.

[D]

Yes, I did get it.

[C]

I didn't know you had a tattoo.

[D]

Yeah, that's. Yeah, that was. 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. And I, I don't have any tattoos. And it was basically, you know, Bill Perkins, like, 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, like, call my friends and family. I was kinda like, hey, Is this like. 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.

[C]

I mean, when you got money like that, what's a couple hundred thousand to him?

[D]

Yeah. Can't say them out. Exactly. I won't confirm it. I never did.

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[D]

Some numbers thrown out there. And it was. It was a good wager. Yeah.

[C]

I wonder how much I would. Because I have no tattoos. I don't want them, so I wonder how much someone would have to pay me to get one.

[D]

Be careful. Throw a number out right here. What are you. What are you talking. What. What's in your neighborhood? What do you think?

[C]

Dude, it has to be at least six figures because first of all, there's a lot of new research on the ink.

[D]

Yeah.

[C]

So I'd have to get like, a holistic tattoo.

[D]

Okay.

[C]

Because the old ink is actually bad.

[D]

For you saying I might have a problem.

[C]

I don't know what you got.

[D]

It's a very tight. I mean, I see people with full body art. Yeah, it's like a little. You know that, like, I'm a very.

[C]

That's leaching in your skin.

[D]

Right? So, yeah, it can't be great.

[C]

Can't be the best.

[D]

Yeah.

[C]

But I'm sure a small one wouldn't hurt.

[D]

Listen, if you put a price out, I know there's a lot of. Do a little. Little fun rate. Little. Little group pool.

[C]

I don't like that. It's random, though. Like, you don't get to pick what it is.

[D]

Well, no, I mean, we. That's the 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 other than, you know, if I had to.

[C]

Pick, it'd probably be my girl or, like, her name or something simple.

[D]

Put a price out. Yeah. I'll crowdfund out here. I'm pretty sure we get it done.

[C]

That's hilarious, dude. That's legendary. Yeah, the poker guys. You guys are. Are different.

[D]

There's some really wild prop bets. Like, I mean, I'm just. Those are just a few that people I know are. We're a part of. But there really is some, like.

[C]

What's the craziest one you've heard?

[D]

Well, the. The in the dark or the what? 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, there's a video of it. It was on live stream. How did he sleep days? Yeah, he was in a bathtub. He'd call room service.

[C]

Wait, there's a bathtub?

[D]

Like he was in the. He was in a bathroom.

[C]

Oh, I thought you meant the public one.

[D]

Okay, so of the room in the room in the room in the room.

[C]

That's still disgusting.

[D]

Crazy. Yeah, that's 30 days. And this was probably like 2010. There was actually a way sicker one recently. You could Google it as well and, and get like video and, 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 a hundred thousand that he could live in a dark room, like a no light for a month. Like kind of crazy isolated, like in there, you know, 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 3 weeks or they bought out for like 60 or 70k. Like they're worried, you know, health reasons. Like being in a hole for. Yeah, 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 no didn't eat, didn't have any food for a couple weeks. And he did that pretty, pretty crazy. Bill Perkins, he's like the, he's like a master proper. Oh, there's been liposuction ones. Like what? All right, I'm sorry. There's been body fat ones where people have like 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 started one more, which I actually had a big bet on was the Staple Brothers, Jamie Staples and Matt Staples, two poker streamers, Good friends of mine, they brothers and want Jamie. I'm again going to get the weights wrong. But one was like £350 and one was like, let me see if I don't mess this up. Might have been like 120 or something. Like, like. 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 1 odds on it. And that was a crazy bet that was on. There was on a site, poker shares. They posted at 31. I bet at, like, I got like, eight different prices. At 30 to 1. I got some at 50 to 1.

[C]

Damn.

[D]

I got like, all these odds. And then. And they did it.

[C]

They pulled it off. What weight did they meet up?

[D]

It's like 100. Let's see, 91. 320. Might have been like 180 or 1 or 200 or something. 190. So the guy. Actually, I think I want to say that the one guy was Matt. Might have been like 110 pounds. They had to get like, to 180 and three.

[C]

Crap. And they're brothers. How are they so different? 110 and one.

[D]

That guy was like three. Jamie was over 300 pounds. And I have a picture of it. We were on twitch in. In St. Thomas, and someone on the chat threw out this idea. We're like, live on Twitch. Like 2. This was like 2016 or 17. And someone's like, well, how much for these guys to do it? And Bill was there. Bill, a lot of Bill Perkins brought back.

[C]

And he loves.

[D]

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, that was probably one of, like, the cooler ones that actually had been. Oh, I. Man, this is actually we could use.

[C]

They keep coming.

[D]

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 was Svatni. He's like Swedish or Danish. And he got. He said, how much you have to get paid to get breast implants as a man?

[C]

Oh, my gosh.

[D]

And so this. 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. 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. No, that's true. At least as of year. Five years ago. It's 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 scene. So that's a crazy one. And there was one other. I was just thinking of that. I forgot. Forgot but there's cops.

[C]

As a man.

[D]

Yeah.

[C]

That's no joke. So he. He has to wear a bra.

[D]

Allegedly. I don't. I have no idea. I've never. But I. You know, that is one that is like a gambling lore. There's another one I just thought of. There's a lot. There's a lot. These are telling. You could do a show on like the. Just the.

[C]

Bill Perkins is hilarious because that's the best.

[D]

Has he been on yet or no? No.

[C]

I'd love to get him on.

[D]

But that book's great.

[C]

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.

[D]

He was all in.

[C]

Yeah.

[D]

Lodge in. In Texas. Doug. Doug Pol. He's got that game. And he literally went all in and left. And he was bluffing, I think, or he maybe had the.

[C]

I think he was bluffing and he ended up winning.

[D]

The guy folded again. Like, stuff like that.

[C]

Savage.

[D]

He's. He's got a lot of.

[C]

I mean poker's probably just a side quest for him. That's not even like.

[D]

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 2013-15 played in a pretty high stakes cash game and I'd stay with Bill and he. He was one that said he. 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 like as an investment, just from the relationships and business and things he's done, he got like a ton out of it. But now he's like spent time and he's like studied and he's actually like if he wants to play well, you know, he knows really exactly what to like. He's tough, like he's a good player, but then again he's busy. He's like, you know, there's times you on your phone or you play a tournament, he plays a tournament 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 very smart guy. One of my best friends. Amazing guy. And again, die with zero. I got it. You got to plug in. You got to have him. He will not Dream guest. He's. He's. He's in Vegas Fair amount. And yeah, sure, he'll. Hell yeah. Come on.

[C]

You still playing often? You still streaming?

[D]

I do. I. So I do a show once a week called GG 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 GG Poker. That's. That's every Tuesday. And then I do podcast. Still do a lot of that. Shout out to Nathan Sharonique, videographer, and now in Miami. So we built a studio and do a lot of work there and. And I try to do live. I think it is a lot better live. But of course sometimes still do do them online. But I. I enjoy the podcast. I. I haven't quite put the formula like you where I'm you know, doing like a ton at a time and I want to. 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.

[C]

We'll get you there.

[D]

It's. Yeah, I respect the process.

[C]

Like my clip guys here, I'm 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. It's the best quality in Miami by far, but also one of the best in the country because, dude, it's a struggle getting good studios. Yeah, I filmed in Phoenix, I filmed in la. I filmed in like Salt Lake and New York. And the quality is just ass.

[D]

Yeah, I apprec. It is. 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. It's fun, man. So yeah, hopefully you. Hopefully you make that a. Like a. A quarterly stop where it's.

[C]

Oh yeah, I will. I might come for Basil. We'll see. But if not, I'll be there for F1 next year.

[D]

Is. Have you been there for either of those?

[C]

I've been for Basil once. I haven't been for F1 yet in Miami. Was it good last year or this year?

[D]

I guess it's awesome. I think our Basel is like the best time of.

[C]

Oh, is it Basel?

[D]

Yeah.

[C]

Oh, my bad.

[D]

Sorry. That's A good clip. Basil. People are gonna like that. No, but it's fun. It's a great time. And it's. It's F1 and, and that are awesome. So.

[C]

Okay.

[D]

Miami's got a lot of stuff going on. Messi's there now. Sports are coming. It's. It's really changed in the last four years.

[C]

Imagine getting messy on the pod. I'd be nuts.

[D]

I mean, they put it out there. Why not? Yeah, he's in the. He's in the neighborhood.

[C]

I wonder how his English is.

[D]

You learn Spanish for that?

[C]

Yeah, I might have to. I would do it for Messi.

[D]

Yeah. I would learn Spanish.

[C]

Yeah. And Ronaldo.

[D]

Yeah, that's. Maybe we should do a bet. Who can learn Spanish in a year?

[C]

Okay, let's do it.

[D]

I'll. I'll. I'm not actually. That's not totally fair because I've been doing duolingo Portuguese.

[C]

Plus, you're in Miami.

[D]

Yeah.

[C]

So you got a home field advantage.

[D]

Give you a little bit of odds, but people we can do about.

[C]

Yeah, I would need odds on that because people practically speak Spanish there on the streets.

[D]

Yeah.

[C]

And it's like the main language there.

[D]

If. All right, let me. If Messi was going to be on the pod in, in three months, what. Well, how much time would you do? Would you cancel everything?

[C]

Oh, I would dedicate eight hours a day and just. I would probably go to Mexico and just walk the streets and, like, learn it.

[D]

That's damn messy, man. That's. That's a lot.

[C]

Messi's top 10 in the world in terms of, like, just fame and followers.

[D]

I mean, he's. I mean, I played soccer my whole life, obviously. I'm. I agree. He's. That would be. That's a. He's definitely. It's cool to have him in Miami. I've. I actually went to one game, and it was a final where they made it last, like, last season, he didn't play, and it was. That's like a big sweat because he's like, you know, he's getting older and he messed up, so I still haven't seen him play, which is sort of irresponsible to be in.

[C]

Yeah, that's a once in a lifetime thing at this point. He's probably got a few years left.

[D]

Well, it's crazy because they lost in the playoffs just now, and they were. 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.

[C]

Wow.

[D]

They blew it.

[C]

They got Suarez now, too.

[D]

Yeah, they're blew it. Yeah.

[C]

Damn.

[D]

Yeah.

[C]

Well, dude, it's been fun work, people. Check out the studio and check out your poker stuff.

[D]

So Miami, you can go to mediographer.com and rent a spot or talk with Nathan there. He, you know, you obviously know Nathan does your man. He is. He's 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. It's great to see you. You coming up and killing it. And this is, this is. I, I do. I get a kick out, like the celebrity Poker tour. This thing is awesome. It's amazing how they have everyone here. I've, 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.

[C]

I'd rather do this than play just because I'm all about getting that content in. So. Yeah, well, playing's fun too.

[D]

Yeah. Big, big crowd. I talked to Maury, who is, you know, Maury.

[C]

Yeah.

[D]

Doing amazing content here, and they've just, they like poker Go. They've given it a ton of praise. People I talk 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 was, I, I assume like a Blake win, who. Yep. Started it, founded it, you know, whoever actually like saw this through. It's. 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. So.

[C]

Absolutely.

[D]

Yeah.

[C]

We'll link your stuff below. We'll link Celebrity Poker Tour below. Thanks for watching, guys. Peace.

[A]

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