Jeff Gross On Playing Poker with Celebrities, Building a Poker Empire & Investing | DSH #159

Have there been times where you just were on insane losing streaks and you were just questioning, like, playing poker professionally?

Yeah, for sure.

I mean, I've had, you know, there's so much variance in poker.

There's, it's, it's crazy.

You could say it's win or lose.

There's times where I'm not playing great and I'm winning.

There's times where I think I'm playing great and I'm losing.

So it is tricky.

And, you know, that I think it's important to take a break, step back.

There's a lot of different stakes.

You can.

I don't, I don't imagine myself having four or five or just yeah.

They probably outsource most of it, though.

Outsource?

Yeah.

Well, Elon has 10 kids.

He's with him every day.

i didn't know he had 10 kids yeah that's crazy i thought he had like six but that's even

though how is he with this tate has a bunch too andrew tate yeah that's what i'm saying i don't know how you can do it all i don't know how they can do all that

Welcome to the Digital Social Hour, guys.

I'm your host, Sean Kelly.

Here are my co-wayne Lewis.

What up, what up?

And our guest today, poker legend, Jeff Gross.

Thank you for having me.

How's it going, man?

It's good, man.

I'm actually a little burnt out.

I got, you know, I just had another kid, two kids, and I was in the WSOP main event.

Went to day five, got a weekend yesterday.

Just got knocked out yesterday.

So today's day six.

I got knocked out yesterday, but there's long days, man.

You can't really put it into words.

It really is grueling.

Like, it's there.

You know, you play too far.

He was playing in it too, right?

Yes, he made the money as well.

Yeah, I seen him Saturday.

Yeah.

Yeah, I was actually, he was with us.

Yeah.

Yeah, you went deep, man.

Was that the farthest you ever made it?

I made it further once before, but

yeah, I got 260th out of 10,000.

It was deep, yeah.

Oh, you started off at 10,000 left with 260?

Yeah, there's 10,000 people.

10,043 entered, and there was, I got 260th.

I got money.

Which is insane.

So what do you leave with when you got that?

Do you leave with anything?

$50,000 for that.

But it was $12 million to first, $12.1 million to first.

So, yeah, a little difference.

Little.

Yeah, a little different.

And you're playing 12 hours a day, right?

Yeah, you you play five, two-hour levels.

You get a break, dinner break, and 20 minutes every two hours.

But yeah, it's tiring.

You know, you wake up and then you're excited when you get deep and you don't sleep good.

And

it's a process, but it was nice.

Are there ever any hands that just you have nightmares about when you look back at your career?

Yeah, a lot.

I've been heads up for a World Series bracelet before, you know, got it in a head and lost.

So like those are the ones that, you know, it's like a Super Bowl for a poker player, and you imagine hitting the upright and to win the Super Bowl.

Like it's, you know what I mean?

Like these type, you don't know when you're going to get back.

Like that was 10 years ago.

And I got second and then still I don't have a bracelet.

I have seven final tables.

And, you know, it's, you do think about hands.

There's a famous quote in that, you know, you just remember the, I don't know how it goes, but it's essentially you remember all the bad beats, right?

The ones when you get lucky, like even in the main event, I got kings and the aces.

I had kings.

This was on day after the money hit, but on day four and I won.

I got lucky, you know, like I have so many times where I lose with like the bad aces or I get drawn out, but I forget, you know, it's like the ones where you get lucky, you usually forget.

Interesting how the brain works that way, right?

Yeah, of course.

What actually got you into poker?

Like, what was your first intro to it?

So

I played soccer my whole life, played in college, and then high school, a person on the team, Craig Pfister, I remember high school.

Yeah, he brought poker chips, like plastic chips, to the soccer camp, and it was awesome.

Like, you know, this was 2003, Chris Moneymaker.

I don't know if you know poker at all.

Yeah, this guy he won.

I know him, yeah.

He won the main, and his name's Moneymaker.

He wins the main event.

He beats a professional heads up it was on the espn it was like the first kind of year that you know it started getting bigger and then it just like blew up overnight like everyone was obsessed with it and that was right around the time in the movie rounders too i don't know if you're familiar

so that that kind of that like the money maker effect someone bringing the chips and playing and uh camp and then and then that happening all the time

Honestly, I love games, board games, video games.

So it was when I when I found this, I was like, wow, you can actually win money.

I was like, this is, you know, it's like a sprite commercial.

I don't know if you ever saw this.

They're like, the twist the cap, they're playing a video game.

He's like, what'd you win?

Yeah.

You know, like, and he's winning some free something for Ken.

It's like, it's nice when you actually can win something for, you know, for playing a game.

So, have you ever had a job?

Or you've just been playing poker?

No, it's like, yo, that was your job.

Yeah.

Yeah, I played track, you know, soccer my whole life, so it was nice because I could go online, play cash games, just come in and out, you know, anytime.

So that was, that was sort of, I found that in high school, and that was it.

Like, I played, damn, that's crazy.

Yeah, played college soccer at South Carolina, and it was perfect, too.

I would go to school,

play, but then I could go play online for a bit, and then, you know, not have to have an actual

couple bucks.

And poker has changed a ton.

Like, back then, 2004, 2005, it was like, I mean, people were just giving away.

It was literally, I didn't know what I was doing, but I was free money.

Now, there's solvers, there's, you know, it's gotten tougher in general, but there's like a huge boom right now where there's like the numbers are records everywhere.

This year, the World Series main event had 10,000, 34, I think the previous record was like 8,700.

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54 years old.

Interested in poker.

Personally, I play baccarat.

Okay.

But poker seems like a lot.

It just seems like a lot.

Yeah.

It's slow.

It's all day.

It's honestly, I think it's the most beautiful game in the world because it's sort of like golf where you get to, you know, if you go with a couple buddies or a group and you get to know someone, how they handle winning, how they handle losing.

There's also, it's like a perfect amount of of skill and luck where you know baccarat blackjack roulette these games are fun you know that the the math is the math right on roulette you're losing 5.7 percent every spin on a double zero wheel if you bet a hundred dollars you're losing five dollars and seventy cents that's just what you lose every time now you might win that day but it's that's the math right and like poker you can actually have a significant edge if you're playing in a home game or you're playing in a spot you can you can kind of dictate how much you're risking in what spots, right?

You can make tight folds.

You can know that if you have top set, you have the best hand, right?

You know for sure that you have the best hand, and you can

dictate your bet sizing.

So I just think it's a beautiful game.

And I was talking to Sean earlier, it's like a lot of my closest friendships are from,

you know, poker directly or indirectly were contacts that I've met from playing.

So because Sean's into it, he throws tournaments.

I don't even play, but just the networking aspect.

I mean, you met guys like Bill Perkins, Michael Phelps from playing poker, right?

Yeah, no, Phelps I met in Windsor, Canada, when I was 19.

It was like 2006.

Yeah, we met playing and randomly and I had roommates for seven years.

And

that was back in

2006.

I mean, it's just like Bill Perkins, you mentioned these guys.

It's just funny to see people calibrate poker.

It's not necessarily win and loss in those games.

Like, even like you say, you throw these things, like whether you lose a little bit playing.

Like, it is just, it's nice to get to meet people and really see how they, I say it in golf too.

Like, how do you if you, if I don't know if you golf, um, you know, it's like, it doesn't really matter if you win or lose, but it's nice to see how people, you know, people cheat, people do little stuff.

I mean, yeah, you could like, you know,

you could hit it out, or, you know, you're golfing, right?

And like you're two different carts, you're not by each other.

You could like, people do shit like that, or they're gambling.

Yeah, but like, it's like in poker, too.

It's like, how, and also in golf, if someone hits a great shot, like, do you, do they, are they happy for you?

Are they, are they not?

You know what I mean?

Like, it's very similar in poker.

Like, you can take a bad beat.

If you see a guy, like, pounding the table, freaking out, that guy probably doesn't have his stuff together, you know, or maybe things aren't right.

So it's nice to kind of see how you handle your success, your wins, and and losses yourself personally and others and yeah i mean i obviously i'm biased i love the game it's a great game and you got good at reading people from playing the game yeah i think you naturally you you you put work in and you start understanding that there's this um so again i don't want to get too deep into like the poker side of things but it's gto right it's called game theory optimal that is um that means like kind of what the solvers say what the book says like on the board if the board is a specific board there actually is a right play similar to chess backgammon There actually is a best play, right?

Best reading a board.

Yeah, so if like, exactly,

there's a computer program that will tell you if the board is ace five nine with a heart, club, spade, versus if it was ace five, nine, heart, hard, heart, like there is a completely different situation on how much you should bet.

If there's $100 in the pot, you know, some people, like the bet sizing is so important.

You could bet $20 or you could bet $100, you could bet more than $100.

So like the computer will actually, there is a best play in every scenario.

So, like, nowadays, there's a lot of this stuff.

You even, Jungle Man, I think you've maybe even had on here or talk with him.

And, like, these guys, like, these guys are so good.

There's like people that are literally that are savants at the game.

But then there's something called exploitative.

Like, let's say you have a flush draw,

and I just know you'll never ever fold any amount in a flush draw, right?

I'd want to bet more because, exploitatively, I know you'll never fold a flush draw.

So, why would I bet $20 when I could bet $150 and make you call?

You know what I mean?

But the book would say bet $34

if there's 100 in the pot to get the right price.

But I'm going to bet 100 because I know you're not going to fold.

So that is an exploitative play.

You're exploiting your opponents.

And that's like guys like Negron you, Helm you, some of these bigger names in poker that have been around forever.

They're very good at reading people and knowing how to exploit in a given situation what to do.

Do you have the book memorized?

Wow.

I mean, there's a lot of poker books.

I've done, you know, look, I got two kids now, do a lot of content.

I'm busy, but I'm not, I can't say I'm studying a lot.

But it's, you know, the top points, it's like golf, man.

You see these guys in the PGA tour, like, what separates them?

They're shooting, like, they're so good, right?

There might be college golfers or guys on other tours that are like really good.

They're like scratch golfers, but the difference between scratch golf and like being a PGA tour, I mean, that's like, you know, I mean, it's a huge difference to get those little bit different.

Same thing in poker.

Like, look, I'm a good poker player, but am I,

you know what I mean?

The guys that are playing the 100Ks, 250K is the best, best in the world, like, they know every spot.

They know the bet sizings, the board textures.

They've run simulations on everything.

Board textures.

Yeah, like, you know, a rainbow board is three different suits.

You know, if it's Ace of Heart, King of Spades, Ten of Diamonds, that's a rainbow.

Monotone would be all three the same, diamond, diamond, diamond.

So, like, there's all these different.

I don't want to scare people away, but

it's crazy.

You know, backyaming got solved, right?

There's these programs that tell you the best play out.

Yeah, yeah.

So backgammon used to be big tournaments around the world.

People would travel around.

It's just gotten a lot less.

There's not as much money.

And actually, Gus Hansen, Phil Locks, and these guys that used to travel around, play

backgammon tours.

Like now, because of that programs and stuff solved, it got...

you know much less exciting and there was it sort of dried up but you know poker is a boom though there's so many people playing you're asking why i think the reason why is content creators out here there's so many people doing podcasts there's people doing um you you know, YouTube channels, Twitch streamers, and it's just, it's gotten, I think, it makes it a lot more accessible.

Miss Botez, I don't know if you're familiar with her.

I saw her make a good one.

She was at my table when she busted.

She took a sick beat.

So she had kings all in to King Jack offsuit and it came ace like 7-4.

So it had to go Queen 10 Perfect.

That's like 3%.

And it Queen 10 right there.

Yeah, that was right.

And yeah, she got knocked out of my table in the morning, but she's a huge person.

personality and now she plays chess but now she likes poker she's streaming hustler live live at the bike poker go.

There's all this content people are seeing and creators, you know, Ninja.

These guys are playing and they're firing, and it's great.

Poker's growing very fast.

And you got in on the content side early.

You were one of the first people to do that.

Yeah.

2015 got into Twitch.

I saw Jason Somerville, who was a very successful player, got into it.

And, you know, I love talking.

And

I have a podcast myself.

And I just was like, you know what?

Let me do this.

Because instead of playing on a poker site and just playing poker, like you could play and people watch you and you get to engage.

So it sort of uh yeah, it just naturally made sense to me and I started doing it and did it for a lot of years in a in a in a row.

So I loved it.

How did the poker mindset help you in business in general and get you established?

How do you feel like you benefited from it?

Definitely in business, I think you have to be able to you have to be able to dissociate results oriented, right?

Like you want to make a good bet, you want to make a good decision, and you can't be results oriented.

And I think that's the, ultimately the best thing that poker does is, you know, like crypto, for example, same thing.

Crypto's crazy.

You know, you know, it goes up and down like this, but you got to be able to detach.

Like you can't get emotional.

Yeah.

You got to know, hey, look, I made a bet.

A company, I like the people.

I like the

owner.

I like the founders.

And I'm going to make a bet size on it.

And it doesn't always work out.

And that could be a lot of factors.

Happens, right?

You invest in some businesses and that, you know, timing is so important.

And there's a lot of luck.

But I think that I am able to.

separate results to not be results oriented.

Like I'm okay with what happens.

And I think that's you know, people freak out.

They put money in the stock market, they put money in business, and something doesn't work out, and you freak out on someone, or like you blame people, or you're upset.

I just feel like I'm really able to

go with not be results-oriented, and

make a decision, and then be okay with whatever happens.

You keep your emotions separate.

Yeah, try to, of course.

No emotion actually.

Yeah, try not to.

We're all guilty of it.

In poker, there's something called tilt.

That's what they call it.

I used to be a sight full tilt.

But

everyone has tilt in life.

Like, you could get tilted right right now.

You run into a car, you get a little accident, or

your parents, something happens.

Like we all get tilt to some degree.

The best poker players are able to wipe off a bad beat, to shake it off and not be like that.

And it's like life, too, man.

Think about a girlfriend or your wife or your friend.

Something happens, right?

And it's like, and you can get like really tilted, right?

Or you can, you know.

you're able to just sort of uh take a breath and relax and that's very important i think again in life and in poker so yeah you just had your first exit man congrats i'd love to hear more about it yeah that was uh that was nice speaking of investments like i've done a uh a a bunch of um

you know i call it very similar to poker tournaments you might play a hundred dollar tournament and win it you might play the ten thousand main event win it you never know which one is going to be so it's it's uh different different check sizes different investments and It was nice to actually hit one, to actually see a wire come in and like, you know, work because it's hard.

I'm sure you know.

And investing, it's not not something that it's a celebration when you get an exit, so that was very cool.

Yeah, I haven't had any yet.

Most of my that was my first, yeah, it's a first.

I mean, a few have gone to zero, a lot are pending, but like it was it was cool.

That was a company, Playmaker, they own sports on Instagram and do a lot of content.

I think better collective is who bought them, I believe.

And

yeah, so you got it in pre-IPO?

Yeah,

I think I came in, it sold for 54.

I got in around 3.5.

Where I forget where the

crazy, Yeah, I forget where exactly what

you make on it.

It was

made a couple bucks.

Not crazy, not like game over stuff, but it was a great deal, and it was a good team.

And same thing.

It was just kind of nice networking.

You know, that great group of guys.

I still remember going to your house in Miami like five years ago, and you told me that story about you got paid out in crypto once on a tournament.

Yeah, so the biggest break I ever got was it was America's Card Room.

It was December 2016, $500 buy-in.

It was actually crazy because it was my longest Twitch stream ever so poker generally starts at like noon depending what time zone you're in and maybe you'll play like 10 12 hours if you were to like win a tournament or go deep but I was in Brazil my wife's Brazilian and I started a tournament at four there was a three-hour time zone in December gap so it was like a one o'clock start or no I'm sorry I started at four was like 7 p.m.

Brazil time I had started playing in Brazil at 9 in the morning and this tournament was

4 p.m.

Eastern so 7 Brazilian and then I ended up winning the tournament I streamed from 9 a.m.

till 9 a.m.

the next day.

25 hours I streamed on Twitch, and then I took it down for 141k from $500, but they pay in

crypto.

So Bitcoin was like $700 a coin in 2016 December.

So they got paid in, but I mean, obviously, I didn't keep all that.

Wait, wait, so you won $124,000?

$141?

Off of $500.

Right, but the real, yes, but the real kicker was you got paid in crypto.

Which was $700 a coin.

And so that was whatever, $141 divided by $700.

It's a lot of coins.

So he made more just holding it.

Yeah, just holding it.

I didn't, again, I did not hold, I didn't just like keep it all on Bitcoin, but that was sort of my like forced introduction to Bitcoin.

I was like, oh, what is this?

How does it work?

And gotten a fund.

Yeah.

And like, yeah, that was the year 2017 where everything couldn't miss.

Like everything was just like, it doesn't matter what you had.

Bitcoin

coin, this coin.

It would just go up.

But yeah, that was like, you know, again, that's like another very,

those type of things, like fortunate, sort of random, random, random thing, and you don't know which tournament you're going to win or how it's going to go.

And, you know, that was fun, though.

25-hour stream on Twitch, that was crazy, too.

Wow.

How do you stay immensely locked in for that long?

Like, you don't have to be a little bit more.

A lot of coffee, a lot of coffee.

My wife's parents are coffee farmers, and it was nice.

We had

a lot of coffee down there for that.

Because I know in chess, you wouldn't think this, but you burn like a thousand calories an hour playing chess.

Yeah.

Just playing chess?

Yeah, so I've never heard poker is similar with all the brain activity.

Maybe.

Yeah, sure.

I've never heard that stat, but that that sounds good.

Yeah.

Yeah.

That's why a lot of those chess players are pretty skinny.

Like, you never see a fat chess player.

You really don't see too many fat poker players either.

There's been a health kick in the last, I'd say, 10 years in poker, I've noticed, because

there is a lot of sitting around, and I would say there's now people have gotten a lot more health conscious in the industry, but there's definitely some heavy poker players, too.

Oh, there are?

Yeah.

But it's a good thing.

It's not going to be a game job, yeah.

It's a good mix.

Yeah.

And then how do you avoid the tilt?

Because that's something a lot of amateurs struggle with.

I just, you know, it's about, I always like to say it's not about what happens, how you react to what happens.

And again, it's easier said than done, but I just, you know, I realize it's a disadvantage.

Like, if you see someone at a table tilting or looking upset, you know, they kind of maybe you go after them a little more, and they just, again, I think it's just a disadvantage.

So it's something like actively working on.

We all tilt.

I tilt, but...

much less I'd like to think than than a lot of others.

So I just try to try to remember it's a new situation, right?

If you take a bad beat, that happened.

Now it's a new hit.

So now, okay, I had 100,000 chips, now I got 40,000.

So now I have, you know, 30 big blinds.

I don't have 100 big blinds anymore.

You have to be able to quickly reset, adjust, and do your best from that point on.

So, yeah, I mean, again, there's a lot of top poker professionals, but I think that's the biggest difference between amateurs and pros.

And again, A game, B game, C game.

You know, you can have a plan.

You know, you go to, you go to, you go, you go play, go pick a basketball.

Hey, today I'm going to make it, I'm going to pass a lot.

I'm going to play good defense or whatever.

And then, you know, someone elbows you

in the mouth.

And next thing, you know, you're ready to just go crazy and your whole plan shifts so I think it's a it's important to try to try to stay grounded and again the the the biggest thing in private poker games too is like a lot of the guys I would call recreationals their a game is like pretty good like fundamentally like okay I know I shouldn't open jack 10 off suit under the gun but like again they they lose a pot they take a bad beat next thing you know like oh they're down 20 grand yeah now it's oh jack yeah I'm not opening even Jack 10 I'm opening you know Jack 5 suited and I'm I'm calling three bets and playing bad so I think that's like people really in general, they have a hard time to be able to,

their C games are so much worse.

You know what I mean?

They play A games, but they can drop down very quickly.

Who would you say like your toughest opponent was that like frustrated you?

There's so many good players, but I know Antonio Esvandiari, who's one of my closest friends, he's known to, he won the $18 million one drop and $2,000 million buy-in.

He's just one of those guys, again, like exploitative versus GTO.

He's just tough.

He just feels like he knows what you have.

He's got the bull.

Like he does all the tricks and

kind of gets in your head.

And

he's very tough.

And he's also a guy, like in friendships, right?

He's your best friend.

He's one of my best friends.

But he wants blood.

Like, he wants to check raise.

He wants to show you a bluff.

And that's something that

he's got that kind of killer mentality and wants to punish.

So yeah, he's tough.

Yeah, that's tough to balance because when I hoop with my friends, I kind of don't play as aggressive.

Are you like that in poker?

Yeah, you know what listen they always you want to talk about check raise your grandma and go at you know for for no friends at the poker table, but I definitely you know, I do feel I that's not him.

I am a little more I'm not gonna soft play.

I'm not gonna you know not go for it, but I'm also just not gonna go out of my way.

Like there's spots where like, oh, I have ace five suited.

You know, you should three bet, but maybe just flat.

You know what I mean?

Like there's a, there's, there's definitely

I would say I'm not as cutthroat.

You know what I mean?

I don't go, I don't go out of my way to try to like punish my friends.

And some people do.

And hey, listen, it's not right or wrong.

Again, it is fair.

It's all fair at the poker table, but I'd say I'm a little less aggressive.

Have there been times where you just were on insane losing streaks and you were just questioning

playing poker professionally?

Yeah, for sure.

I mean, I've had, you know, there's so much variance in poker.

It's crazy.

You could be a world-class player.

There's 95 events at the World Series this year.

I mean, you could be the best player in the world and have a losing World Series.

You could play a lot of events and not do well.

So, for sure, I've gone through patches and it's hard not to be results-oriented, right?

Like if

you go play 10 cash games and you lose eight of them, you could play great, and that's possible you could lose.

So it's very tricky to be honest with yourself, right?

It's win or lose.

There's times where I'm not playing great and I'm winning.

There's times I think I'm playing great and I'm losing.

So it is tricky.

And I think it's important to take a break, step back.

There's a lot of different stakes you can play, right?

You can buy in 10K buy-in, 5K buy-ins, 25K, there's 100Ks.

like when you're hot feeling good you know press and when you're not like it's important to sort of take a look back step back and really understand am i playing well am i running bad right and be honest like everyone wants to say they got bad beat oh i got unlucky but you know even like when i busted the main event like i you know i i uh I think I could play better, right?

For sure.

It's five days.

There were spots where I should have maybe pulled the trigger or the bet wasn't right or I made, you know, I made a mistake.

And it's just easy to say, oh, I got unlucky.

And it's just hard to be honest with yourself really that's the hardest part in poker yeah so yeah I mean because there's so much strategy to it like you said so many different variables it's like where what spots are you messing up in for sure yeah it's hard it's hard to get are you studying film after your sessions no I'm not I mean look I got two kids I got I got the podcast I do YouTube content I'm I'm I'm like um you're retired semi-retired at this point yeah I haven't play I don't play as much anymore honestly I I I I love the game but it's a lot of other passions and you know it's um again I'm not playing every day.

If I was, I'd need to be studying more, but I play sort of more home private games when I do play, which isn't a lot.

And then I love to come out to the World Series.

And I'm an ambassador for GG Poker, which is the spot.

I don't know if you see the World Series.

That's like the

tables.

Poker GG.

Oh, yeah.

GG Poker.

So like five years ago, four years ago, Poker Stars had, I believe, like 65% of the market share.

GG had six.

Now GG has like 65 and stars has like 30.

So they've like 10x.

They're the biggest by far.

Best software, best tournaments, best guarantees.

I just put on like a 200 million guarantee month series online.

I do a weekly show for them on YouTube called GG Millions.

It's a 10K buy-in on Sunday, and then it plays down to the final table.

And then on every Tuesday, I do the final table commentary.

So that's like my set role with them.

And then, yeah, man, just content, poker, poker podcasts, and

had a son three months ago, second one, and that's it's changed a lot.

You guys have kids?

I don't have any kids.

I want one soon.

Yeah.

How old are you?

34.

Okay.

36.

Yeah.

Yeah, I'm thinking like around 30.

It changes, man.

It's great, but it's like that.

I always actually wonder how people, you see people like super successful, have like four or five kids.

I just don't know how they can like.

I don't imagine myself having four or five kids.

Yeah.

They probably outsource most of it, though.

Outsource?

Yeah.

Well, Elon has 10 kids.

Do you think he's with them every day?

I didn't know he had 10 kids.

Yeah, that's crazy.

I thought he had like six, but that's even though he's not.

That's what I'm saying, though.

How can you tell me he's a present and like great father, right?

Like he's saving the world, doing 10 different.

John has 10 kids?

Yeah.

Andrew Tate has a bunch, too.

Andrew Tate?

Yeah.

That's what I'm saying.

I don't know how you can do it all.

I don't know how they can do all that.

They learn every day there.

There's a balance.

I think you like being more hands-on and you spend quality time with them.

Yeah, you try to, but

it just seems tricky, right?

I don't know.

I'm learning as I go, but it's also, I think, the time, the period of life you're in.

You know, I'm 36, kind of like in my, like, I've i've been pushing and want to keep going and it's just you know that's why i think as a man we have time right if we're at 40 42 44 it's like

man i mean robert de niro just had another one at 70

that's too late though because you want to enjoy it too i mean who knows how long he's i mean it's that's his legacy i guess yeah i don't think he's too much thinking about how long he's gonna be here that's true

his girlfriend's 28.

she's 28.

yeah that's all right that's a little that's a little covered i get it i can wait

what do you are you supposed to have a baby by a 70 year old woman yeah no no no you're right you're right but I'm just saying that you get my point It's like you have the same thing you do content, you got your podcast, you got a hundred different things going It is once you do it's just like a whole different yeah we go months without talking to each other because we're both just so I mean that's that's the wild part like it's you know you you have your buddies right now you have your routine and then next thing you know it's like you're just it's completely different like you start hanging out with people around you that have that are that have kids or you know they're they go to school and like you're it's just it's just interesting to see bill wrote that book die with zero and he talks a lot about that about your different parts of life where it's like, you know, you're not going to go hella skiing when you're, when you're 65, right?

There's certain things you got to do

at the time in your life, and also you can't take the money with you.

It's like you want to, you know, if you're, if you're going to, if you have kids, you want to give them something, you know, it doesn't make sense if you're 85 to give your 60-year-old a million dollars if you have that, right?

You know what I mean?

Like you want to give in their 30s, 40s, you want to give stuff that

is useful and makes sense then.

I've heard people in their 30s and 40s have a midlife crisis.

Have you experienced anything like that?

I do?

I've never heard.

I don't know.

Midlife crisis.

I don't know.

It's like 50s.

It's mostly for men, though.

I don't think men have men, right?

Mainly men.

I wouldn't say I've had luckily knock on wood somewhere.

I don't know.

I haven't felt the midlife crisis, but I definitely feel with kids, it gets a bit overwhelming.

It's just like a bit like you want to, as a man, you want to help, you want to be present, but you also need to provide.

You want to burn, you want to work, you want to build your stuff.

And it's not easy to find that

yeah that's good to know yeah because i want one but i don't ever think about the sacrifice off the board i mean you gotta choose your regrets what do you mean uh well i mean

the it's cost there's cost to opportunity yeah right so when you're not having kids right you regret

like when you don't have kids you regret not having them at a certain age but you may have this success so it's just a cost of opportunity right it's always greener on the other side oh do you have a a girlfriend?

Do you have a wife?

Do you have to be single?

There's like, all right, you got your buddies that are single, partying, traveling, a golf trip.

What do you, yeah?

Bachelor party.

This stuff means like, oh, I got to, I'm, I'm with, you know, it's hard, man, but you got to exactly.

You got to choose your regrets.

No, that's facts.

I can't go out with my single friends anymore.

Right.

I had to keep that up.

I mean, you can't, no, no, but you can, but it's not, it's just not like an everyday thing.

It's like, all right, once in a while, or, you know, it's just hard.

Yeah, I'm going to go to, I'm going to go with my buddies tonight.

And you're,

it's, I know exactly what you're saying.

it's just it's different it's just different it's not like you're just not hanging out all the time it doesn't feel like I belong there you know well no I mean I just feel like obviously in life like again you got to choose your regrets so at some point you'll start to

you're supposed to enjoy it because you said I mean we all have a clock I mean so it's like what are you going to choose to enjoy because you're going to live and then you're going to regret not going out and then you're going to want to go out now.

So it's going to, trust me, everything that you're not doing will eventually be knocking at your door like, like, hey, it's time for you to start doing this.

You know, I met my wife at Burning Man when I was 27, and I was single from like 20 to 27.

But so I had a, you know, I had a good run, like a lot of fun.

I was out, I was partying, traveling, doing all that.

And I do think that is, you know, it is important to have that because you got these people that have got, you know, 18, 19, and they're with someone and then they get married and all that.

Like, it's not saying it can't work, and that's great.

But then you're like, then you may start wondering, wow, I never got to really like party or do anything.

So I do see that happen a bit where I've had friends that have been, that they've hit that point and they get kind of like stuck.

That is the midlife crisis.

What?

The regrets.

Yeah.

Because you're not enjoying your life in your 20s and your 30s, and then you get to 40-something and now you want to start to experience these things that you didn't experience.

So it knocks at your door.

So again, it's all about choosing your regrets.

I think that you should kind of get everything out of the way, experience it so you're desensitized and you don't really too much care about none of the stuff no more because you experienced it already.

Yeah, but again, everybody's both, yeah.

But at the same time, it's the other thing: you meet your love of your life, you meet someone, and you got to be with them.

It's like you can't, yeah.

But sometimes the love of your life can be just as fun as the friends for sure.

Your girlfriend can be just as fun as.

I mean, I've seen guys like, yo, your girlfriend's cool as hell.

Like, she's out with the boy, she you don't even feel her.

It's true, and there's some girlfriends that are like bosses, like, no, he can't go.

Yeah, that boy can't.

Yeah, that, but for in your 20s, 26

yeah, man, you're, you're young, but you've been, how long have you been in five years, but I had a year or two of that, that phase where I was partying every weekend.

Okay, and I got out of my, I got out over it quick, yeah, college, college, yeah, honestly, like, sophomore year at college, I was like, I don't even want to drink anymore.

Yeah, that's good.

You figured, I mean, again, teach his own, not saying it can't work or be great.

I just think that that is, it is, uh, it's important, it's important to understand that at least, make a decision and understand, like, what you, you know, make a conscious choice on that.

But, yeah, Jeff, what's next for you, man?

Uh, going to Brazil from here.

My gonna be there for a few weeks, and then I am good.

Yeah, my wife's Brazilian, so it's nice.

It's a nice, it's a like farmland, man.

Just out in the middle of nowhere.

Enjoy it, disconnect, and then go to London for Triton.

They got these like high-roller poker series.

I do commentary and interviewing for that.

And then

podcast, man.

Also, I love love that you guys have a studio.

You know, I do a lot of podcasts.

I've done more of the

on-the-call stuff.

I do want to get set up and make it more, a little more professional production,

have the live feel to that.

And then,

I mean, man, I'm just

been non-stop.

I love investing.

I think I mentioned you Skyfy.

So I'm helping with that.

Bill Perkins started that, satellite imagery, where you can sort of, you're able to purchase photos and it's available to anyone, right?

So it's like, it says there's business side of it as well for seeing overhead shots.

And

you got to check it out.

Skyfy.com.

It's very, very cool.

That I'm helping with.

And then Hybrid, which got the hat on, that's sort of like a more solver GTO sort of friendly version, though.

Because like the P.O.

solver stuff, right, where you got to like plug in hands, it's very tedious.

So I'm like, hey, you want to get good at poker?

You're not going to want to go.

I don't want to do it.

And I play professionally.

It's a lot of work.

But this is more, you know, it'll basically give you hand examples.

You play, and then you get to learn visually because

it'll give you a game tree.

So it'll say, like, oh, you don't play this spot well.

You basically play hands, you make a choice, and then based on that, it does a game tree, and it'll say, Okay, you're big blind defense.

You don't know what you're doing here.

You're absolutely wrong.

And then it'll just give you those examples to work on.

So it's like a really AI study

tailored to someone who's like a recreational or beginner that can learn advanced principles very quickly.

He put a lot of money into it, and it's a really nice product.

So, yeah, I've been helping with that, working on that, and just staying busy, man.

I had two kids, and

it's been hectic.

So, I'm looking to relax.

You're stopping at two?

two's good

my wife my wife turns 40 next week i'm 36 and i think that's uh you know

cougar action there yeah

exactly right i don't think she's a cougar yeah it's yeah

mountain lion mountain lion no not quite not that not quite there cougar would be 60 yeah no

she's she's young man she's young and fun we met at birdie man and you know she's got a good spirit and that that uh it it is it is it's a blessing to have kids and yeah just keeping busy man all right thanks for coming on man that was sick yeah i I appreciate it.

Thank you, man.

Thanks for watching, guys.

Nice to meet you, man.

And I'll see you next time.

Bye.