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

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.

60, 60.

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.

I did 30 days.

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 were public one.

Okay.

No, of the Bellagio.

So that's still disgusting.

Isn't it 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 with 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.

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 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 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, lived together.

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?

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 $100 bills.

So there was no chips.

It was like you were playing Badugi Bidesi and it was like, you know, $2,500 clips, $10,000 wraps, $1,000 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, 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 wanted 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.

Like 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, mostly white dominant.

And they hit the alarm to like he was rocking the bank.

so that's a true story very bank yeah i'll tell you he was on my podcast

yeah this was back in the day a long time like maybe 15 years ago but that's a true story so dude that's crazy yeah i'm sure some of these home games get insane 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 uh 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 bolzerian bike ride bet

so brian rast he got bet if he could ride and i might mess the exact details up it was essentially that he could ride from vegas to uh 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 at action on it and bill perkins and dan bilzerian 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 Rast was like, couldn't, couldn't move.

And they had like a doctor like drive out.

They found him in the GPS, like ran him in the hills.

And he like took a, they like shot a shot at 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 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 bet him like a million and then bought out and just paid him.

He didn't even 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.

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 have 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 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, you know, 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 next day I was there and I had to call my friends and family.

I was kind of 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.

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.

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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.

You throw a number out.

Just market 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.

Yeah.

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

Okay.

Because the old ink is actually bad for you.

You're saying I might have a problem?

10 years.

I don't know what you got, bro.

There's a very tight.

I mean, I see people with full body arcs.

Yeah, it's just like a little bit like a very small one.

That's leeching in your skin.

Right.

So 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

little fundraising, 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 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 a pick, it'd probably be my girl or like her name or something.

Well, if you put a price out,

I'll crowdfund out here.

I'm pretty sure we get it done.

That's hilarious.

Dude, that's legendary.

Yeah, the poker guys, you guys are different.

There's some really wild prop bets.

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.

What's the craziest one you've heard?

Well, 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, 60, 60.

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 say it?

30 days.

Yeah, 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 but in the room for disgusting crazy yeah like you 30 days and this was probably like 2010 there was actually a way sicker one recently um 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 a hundred 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 or four 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

I'm sorry, there's been body fat ones where people have like got liposuction at the the end to try to get it done like get down to eight 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 staples and matt staples um two poker streamers good friends of mine they brothers and one jamie i'm again gonna get the weights wrong but one was like 350 pounds and one was like

uh Let me see if I don't mess this up.

Might have been like 120 or something.

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.

It was on a site, Poker Shares.

They posted at 30 to 1.

I bet it like, I got like eight different prices at 30 to 1.

I got some at 50 to 1.

Damn.

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

They pulled it off.

What weight did they meet up?

It's like 100 and let's see, 91, 320.

It might have been like 180 or one or 200 or something, 190.

So the guy actually, I think, I want to say the one guy, Matt might have been like 110 pounds.

They had to get like to 180 and 30.

Oh, Oh, crap, and they're brothers?

How are they so different?

110 and 100.

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, like two, this was like 2016 or 17.

And someone's like, how much for these guys to do it?

And Bill was there.

A lot of Bill Perkins propped up.

He loved it.

He was like, yeah, he was there.

He's like, you know, all right.

And then they threw out odds and they did it.

So yeah, that was probably one of like the cooler ones.

And that actually had been, oh, I, man, this is actually, we could do like

two more great great ones.

The best one I ever heard, and you can look this up as well.

I think his name is Svotni.

He's like Swedish or Danish.

And he got, he said, how much do you have to get paid to get breast implants as a man?

Oh, my God.

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, 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 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 there was one other I was just thinking of that I forgot.

But there's D-cops as a man.

Yeah.

That's no joke.

He said the chicks digged it.

So he has to wear a bra.

Allegedly.

I don't.

I have no idea.

I've never, but I, you know, that is is one, that is like a gambling lore.

Um,

gambling lore.

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 props.

Bill Perkins is hilarious because that's I was hero.

Has he been on yet or no?

No, I'd love to get him on.

But that book's great.

Yeah, he's.

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 go in.

Oh, yeah, he was all in at the lodge in Texas.

Doug Poland'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 and he ended up winning the guy folded a game like stuff like that savage He's uh he's got a lot of I mean poker is 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 was one that said he he actually lost a fair amount of money in poker originally.

He said that'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 he's on your phone or 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 very smart guy.

One of my best friends, amazing guy.

And again, die with zero.

I got it, got a plug in.

You got to have him.

He will

come on.

He's in Vegas fair amount.

And yeah, sure, he'll definitely come on you still playing off then you still streaming 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 uh every tuesday and then i do podcasts still do a lot of that um shout out to nathan charonik

and uh 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 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.

We'll get you there.

Yeah, I respect the process.

My clip guy's here.

I'm going to introduce you guys.

Max is here.

Shout out to Max.

Awesome.

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 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.

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 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, hopefully you make that a, like a quarterly stop where it's like, oh, yeah, I will.

I might come for Basil.

We'll see, but if not, I'll be there for F1 next year.

Have you been there for either of those?

I've been for Basil 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 is like the best time of the year.

Oh, is it Basel?

Yeah.

Oh, my bad.

Sorry.

That's a 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.

Messi's there now.

Sports are coming.

It's really changed in the last four years.

Imagine getting Messi on the pod.

That'd be nuts.

I mean, they put it out there.

Why not?

He's in the neighborhood.

I wonder how his English is.

It's not.

You learn Spanish for that.

Yeah, I might have to.

I would do it for Messi.

Yeah, I would learn Spanish.

Yeah, and Ronaldo.

Yeah, that's maybe...

We should do a bet.

Who can learn Spanish in a year?

Okay, let's do it.

Actually, that's not totally fair because I've been doing Duolingo Portugal.

Plus, you're in Miami, so you've got a home field advantage.

I'll give you a little bit of odds, but we can do a bet.

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 Messi was going to be on the pod in three months, how much time?

What would you do?

Would you cancel everything?

Oh, I would dedicate eight hours a day and just learn i would probably go to mexico and just walk the streets and like learn it that's damn messy man that's a that's a lot

messi's top 10 in the world in terms of like just fame and followers 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 uh 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 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's messed up so i still haven't seen him play which is sort of irresponsible to be in Yeah, that's a once-in-a-lifetime thing at this point.

He's probably only got a few years left.

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

They won the regular season, the best team out of 30, and then the first round they lost.

So, I was like, oh, 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 Suarez now, too.

Yeah, there's blew it.

Damn, yeah.

Well, dude, it's been fun.

Where can people check out the studio and check out your poker stuff?

So, Miami, you 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 MySuff, Jeff Grows Podcast, Jeff Grows Poker, YouTube, and all socials.

So, yeah,

it's great to see you coming up and killing it.

And

I get a kick out.

Like, the celebrity poker tour, this thing is awesome.

It's amazing how they have everyone here.

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 bit of a tour?

I'd rather do this than play just because I'm all about getting that content in.

Well, playing's fun, too.

Yeah, big, big credit.

I talked to Maury, who is, you know, Maury as well, doing amazing content here.

And they've just, they, like PokerGo, 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 it was, I assume you have Lake Wynn who started it, founded it.

So, 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 cool.

Yeah, we'll link your stuff below.

We'll link somebody poker tour below.

Thanks for watching, guys.

Peace.