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

Episode Date: November 16, 2023

On today's episode on the Digital Social Hour, we sit down with Jeff Gross to discuss how he built his poker empire, how he invests his money and his deep WSOP main event run. BUSINESS INQUIRIES/SPONSORS: [e-mail] APPLY TO BE ON THE POD: https://forms.gle/qXvENTeurx7Xn8Ci9 SPONSORS: Opus Pro: https://www.opus.pro/?via=DSH HelloFresh: https://www.hellofresh.com/50dsh Deposyt Payment Processing: https://www.deposyt.com/seankelly 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/ Learn more about your ad choices. Visit megaphone.fm/adchoices Learn more about your ad choices. Visit podcastchoices.com/adchoices

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There's, it's crazy. 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, you know, I think it's important to take a break, step back. There's a lot of different stakes. I don't imagine myself having four or five of those. Yeah. They probably outsource most of the though 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 that's what i'm saying though how they can do all that welcome to the digital social hour guys i'm your host sean kelly here with my co-host 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 I'm actually I'm a little burnt out I got you know I just had another kid two kids and I was in the WSOP main event went went to day five got 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, you know, you play 12 hours. Ryan Garcia was playing in it too, right? Yes, he made the money as well. Yeah, I've 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, so out of 10,000. That's amazing. Yeah. Oh, you started off at 10,000 left with 260? Yeah, there's 10,000 people. 10,043 entered, and I got $260,000. Oh, which is insane.

Yeah, it's just deep. So what do you leave with when you leave with anything? $50,000 for that. But it's $12 million to first, $12.1 million to first. So yeah, a little difference. Yeah, a little difference. Yeah, a little different. And you're playing 12 hours a day, right?

Yeah, you play five two-hour levels. You get a break, dinner break, and 20 minutes every two hours. But yeah, it's tiring. You wake up, and then you're 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 the head and lost. So, like, those are the ones that, you know, it's like a Super Bowl for a poker player, and you like imagine hitting the upright and and to win the Super Bowl like it's you know I mean like these types that you don't know when you're gonna get back like yeah that was 10 years ago wow 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 and 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 the main event i got kings and aces i had kings yeah 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 aces or i get drawn out but i forget you know it's like the ones where you get lucky you usually forget so interesting how the brain works that way right yeah yeah of course i actually got you into poker like what was your first intro to it uh so i played soccer my whole life played in college and then high school a person on the team craig fister i remember yeah he brought he brought uh poker chips like plastic chips to the 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 he won the main and his name is Moneymaker. He wins the main event. He beats a professional heads up. It was on 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.

So I don't know if you're familiar around that, that kind of that like the moneymaker effect, someone bringing the chips and playing in the camp and then that happening all at the same time. You fell in love with it. Honestly, I love games, board games, video games. So it was 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 twist the cap, they're playing a video game. He's like, what'd you win? You know, like, and he's winning some free something for Kevin. It's like, it's nice when you actually can win something for, you know, for playing a video game he's like what'd you win yeah you know like and he's winning some free something for kevin it's like it's nice when you actually can win something for um you know for playing a game so have you ever had a job or you just been playing poker uh that was your job yeah yeah yeah i played 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 and that was it like i played was it. Like I played college soccer at South Carolina and it was perfect too. Like we'll go to school, uh, play, but then I could go play online for, for a bit and then, you know, not have to have a actual, make a little bit of money, make a little couple bucks. And poker has changed a ton. Like back then, 2004, five, it was like, I mean, people were just giving away. It was literally, I didn't know what I was doing, but I was 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 got 10 034 i think the previous record was

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It's all day. 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 of 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 skill and luck where, you know, Baccarat, Blackjack, roulette, these games are fun. You know, 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 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 you know dictate your bet sizing so i think it's a it's a beautiful game and i was talking to sean earlier it's like a lot of my closest friendships are from uh you know poker directly or indirectly we contacts that i 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 uh phelps i met in windsor canada when i was 19 uh it was like 2006 um 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 a win and loss in those games. Even like you say, you throw these things, like whether you lose a little bit playing, it's nice to get to meet people and really see how they – I say it in golf too.

I don't know if you golf. It Like how do you if you if you golf, you know, it's like it doesn't really matter if you win or lose, but it's nice to see how people know people cheat. People do little stuff in golf. I mean, yeah, you could like, you know, that you. Yeah, you could hit it out or, you know, you're golfing, right? And like you're two different cards, you're not by each other. You could like people do it like that or they're gambling.

Yeah, but like it's like in poker, too. It's like and also in golf, if someone hits a great shot, like, 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 take a bad beat,

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 losses, yourself personally and others. And yeah, I mean, 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

naturally 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 so like that's reading the board that's yeah so it's like exactly there is there's a computer programs that will tell you if the board is ace five nine with a heart club spade versus if it was ace five, nine, heart, heart, heart.

Like there is a completely different situation on how much you should bet. There's a hundred dollars in the pot. You know, some people, like the bet sizing is so important. You could bet $20 or you could bet a hundred dollars. You could bet more than a hundred dollars. 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've even jungle, maybe I think you've maybe even had on here

or talked with him. And 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 in this, if there's a hundred in the pot to get the right price. But I'm going to bet a hundred because I know you're not going to fold. So like that, that is an exploitative play.

You're exploiting your opponents. And that's like guys like, know negron you uh helm you some of these bigger names in poker they've been around forever they're very good at reading people and knowing how to exploit in a given situation what to do so you got the book memorized um i mean there's 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 the top points it's like golf, man. Well, 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, it's like, you know what I mean? It's a huge difference to get those little bit different, same thing in poker. Like I'm a look at, I'm a good poker player, it's like, you know what I mean? It's a huge difference to get those little bit different, same thing in poker. Like I'm a look at, I'm a good poker player, but am I,

you know what I mean? The guys that are playing the 100Ks, 250Ks, 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. Yeah, like, you know, a rainbow board is three different suits. You know, if it's a Ace of heart, King of spades, Ten of Diamonds, that's that's a rainbow.

Monotone would be all 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. It's crazy. You know, backgammon got solved, right? There's these programs that tell you the best play out. 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, like Gus Hanson, 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 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 know youtube channels twitch streamers and 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 yeah 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 off and it came Ace like seven four so I had to go Queen 10 perfect it's like three percent and it Queen 10 right there and uh yeah she got knocked out of my table in the money but she's a huge 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 and they're firing and it's 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 uh 2015 got into twitch i saw jason somerville who was a very successful player got into it and you know i love talking and that's i have a podcast myself and i just was like you know what let me

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 get engaged so it's sort of uh yeah just naturally made sense to me and i started doing it and did it for a lot of years 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 better company i like the people i like the the the owner i like the founders and i'm gonna 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 i'm okay with the what happens and i think that's really you know people freak out they put money in stock market they put money in business and something doesn't work out and freak out on someone or like you blame people or you're upset i just feel like i'm really able to um go not be results oriented and and and make a decision and

then be okay with whatever happens nice keep emotions separate yeah try to of course yeah try not to the we're all guilty of it in poker there's something called tilt that's what they call those they should be a sightful tilt but uh it that everyone has tilt in life like you could get tilted right now you know you're getting a fence like you run into a car you get a little accident or you know your your parents something happens like we all get tilt some degree the best poker players are able to to wipe off a bad beat to shake it off and not be like that it's like life too man think about you know a girlfriend your 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 bunch of um you know i call it very similar poker tournaments you might play a hundred dollar tournament and win it you might play the 10 000 main event win it. You might play the 10,000 main event and win it. You never know which one is going to be. So it's, it's a 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, it's hard. I'm sure, you know, in investing, it's not a, not something that it's a celebration when you get an exit. So that was a very cool yeah I haven't had any yet most of my that was my first yeah it was the 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 um yeah so you got into pre-ipo yeah um I I think I came in. It sold for $54.

I got in around $3.5. I forget where the – That's crazy. Yeah. I forget where exactly. How much did you make on it? It was – I 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, like it was just kind of nice networking 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 i was december 2016 500 buying 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 uh gap so it was like a one o'clock

start or no i'm sorry i started four was like seven pm brazil time i had started playing in brazil at nine in the morning and this tournament was uh 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 um in in crypto so bitcoin was like 700 a coin in 2016 december so they got paid in but i, obviously I didn't keep all that. Wait, wait. So you, 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. I didn't, I, again, I didn't, I did not hold,

I didn't just like keep it all in 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 doesn't matter what you had bitcoin coin this coin it was uh it was it would just go up but but yeah that was like uh you know again that's like another very um those type of things like fortunate sort of random random random thing and you don't know which tournament you're gonna win or how it's gonna go and um you know that was fun though 25 hour stream on twitch that was crazy too how do you stay mentally locked in for that long like a lot of coffee a lot of coffee i i my um yeah my wife's parents are coffee farmers and it was nice. Like they got,

we had a lot of coffee down there for that. Yeah. Cause 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'm assuming poker is similar with all the brain activity. Maybe. Yeah, sure. I've never heard that stuff, but 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. It's, you know,

there's been a health kick in the last, I'd say it's 10 years in poker. I've noticed. Cause there is, there is a lot of sitting around and I would say there's, um, now people have gotten a lot more health conscious in the, in the industry,

but there, there's definitely some heavy poker players too. Oh, there are. Yeah. But it's, it's a mix. Yeah. It's a, it's a good mix. good mix um yeah and then how do you avoid the tilt because that's something a lot of amateurs

struggle with uh 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 they 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 it 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 that happened now it's a new hand so now okay i had a hundred thousand chips now i got forty thousand so now i have you know thirty 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 can have a plan. You go play, go pick a basketball. Hey, today 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. Your whole plan shifts. So I think it's important to try to stay grounded. And, again, 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 offsuit under the gun but like again 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 five suited and 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 to their their c games are so so much worse you know i mean they play a games but they be able to to their their c games are so so much worse you know i mean they play games but they they can drop down very quickly who's who would you say like the your toughest uh pony was that like frustrated you like good man there's a there's there's so many good players but i i know you know antonio esfandiari who's one of my closest friends he's known it he won the 18 million dollar one drop in $2,000 million buy-in.

He's just one of those guys, again, like exploited versus GTO. He's just tough. You just feel like he knows what you have. He's got the bulls**t. He does all the tricks and kind of gets in your head. And he's very tough. And he's also a guy in friendships. He's your best friend.

He's one of my best friends. But he wants blood. He wants to check 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, you know? 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, 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 that's not 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 i mean like there's uh there's there's definitely i would say i'm not as cutthroat, you know what I mean?

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, yeah. 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 in poker there's it's it's crazy you could be 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 uh have a losing World Series you could you could play a lot of events and not do well so for sure I've gone through through patches and it's hard not to be results oriented right like if you're 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? Because 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-ins, 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? 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 are 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 it's just easy to say oh i got unlucky and and be it's just hard to be honest with yourself really that's the hardest part in poker yeah so yeah i mean there's so much strategy to it like you said so many different variables it's like where what spots honest with yourself. That's the hardest part in poker. I mean, there's so much strategy to it. Like you said, so many different variables. It's like what spots are you messing up in? For sure. It's hard.

Are you studying film after your sessions? No, I'm not. I mean, look, I got two kids. I got the podcast. I do YouTube content. I'm like... You're semi-retired at this point. Yeah, I don't play as much anymore, honestly.

I love the game, but it's a lot of other passions. 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. I'm an ambassador for GG Poker, which is the spot. I don't know if you see the World Series.

That's like on all the tables over GG. Oh, yeah. GG poker. So 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 they've they've like 10 X. They're the biggest by far.

Best best software, best tournaments, best guarantees. They just put on like a 200 million guarantee month series online uh 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 uh yeah man just content poker poker podcasts and uh had the 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 you're how old are you 34 okay 36 yeah it's yeah i'm thinking like around 30 it changes man it just 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 how they can like yeah probably outsource most of the time yeah that's crazy I thought he had like six but that's even that's insane so how is he how can you tell me he's a present and like great father right like he's he's saving the world doing 10 different he has 10 kids right what does he tate has a bunch too andrew tate yeah i don't know how you can do it all i don't know how they can do all that every day there but 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 it is a it just seems tricky right i don't know i'm learning as i go but i it's also i think the time the just seems tricky right i don't know i'm learning as i go but

i 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 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 40 42 44 it's like you know i mean robert de niro just had another one after 70. that's too late though because you want to enjoy it too i mean who knows how long he i mean that's his legacy i guess yeah i don't think he's too much thinking about how long he's going to be here that's true yeah his girlfriend's 28. yeah she's 28. yeah that's all right that's a little that's different i get it i can't wait what are you are you supposed to have a baby by 70 year old yeah no no you're right you're right

but i'm just saying that you get my point it's like you have 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 once without talking to each other because we're both just so i mean that's the wild part like it's you know 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 go to school and like you're it's just it's just interesting to see bill wrote that book die with zero and it talks a lot about that about your different different parts of life where it's like you know you're not gonna go

hell skiing when you're when you're 65 right there's certain things you've got to do at 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 gonna 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 that is that is uh useful and it makes sense then so yeah i've heard people in their 30s and 40s have a midlife crisis have you experienced anything they do i've heard i don't know uh midlife crisis i don't know i'm not like 50s yeah i think it's I've heard. I don't know. Midlife crisis. I don't know.

I think that's like 50. We're not mostly for men, though. I don't think men have that. Men, right? Mainly men. We do? Yeah. I don't say 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 as a man, you want to help. You want to be present, but you also need to provide, you wanna earn, you wanna work, you wanna build your stuff. And it's not easy to find that mix. Yeah, that's good to know. Yeah.

Cause I want one, but I don't ever think about sacrifice. I'll have to make it. Well, I mean, you gotta choose your regrets. What do you mean? Well, I mean, there's costs to opportunity. Yeah. 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. Yeah, so it's always greener on the other side too. Oh, do you have a girlfriend? Do you have a wife? Are you single? There's like, all right, you got your buddies that are single, partying, traveling, a golf like, all right, you got your buddies that are single party and travel a golf trip.

What do you bachelor party this stuff? And then it's like, oh, I got it. I'm with, you know, it's hard, man. But you got to exactly got to choose your regret. That's facts. I can't go out with my single friends anymore. Right? Yeah. That's I had to get that up.

I mean, you can't. No, no, but you can't. But it's not it's just not like everyday thing. It's like, all right, once in a while or, you know, it's just hard. Yeah, I'm going to I'm going to the going with my buddies tonight and 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 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 grid run like a lot of fun i was out i was partying traveling doing all that yeah i do think that is you know it is important to have that because i've got these people that have got you know 18 19 and they 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 twenties and 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 yeah 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 this stuff no more because you experienced it already yeah but again everybody's yeah but at the same time it's the other thing you meet your the 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 absolutely absolutely I mean I've seen guys like yo your girlfriend's cool as hell yeah like she's out with the boys she you don't even feel her. It's true. And there are some girlfriends that are like bosses like, no, he can't go. Yeah. Well, yeah, that but for and you're 2026 year. Yeah, man, 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. Honestly, like sophomore year of college, I was like, I don't even want to drink anymore. Yeah, that's you figured i mean again it teaches on not saying it can't every it can't work or be great i just think that that is it is uh it's important to understand that at least make a decision and understand like what you you know make a conscious choice yeah but yeah jeff what's next for you man uh going to bra Brazil from here. Am I going to be there for a few weeks? And then I am, yeah, wife's Brazilian. So it's nice.

It's a nice, it's like farmland, man. Just out in the middle of nowhere. Enjoy to disconnect. And then go to London for Triton. They got the, these like high roller poker series. I do commentary and interviewing for that. And then a podcast, man. Also, I 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 a little more professional production, have the live feel to that. And then, I mean, man, I'm just been nonstop. I love investing. I think I mentioned to you Skyfi. Yeah, Skyfi. Bill Perkins started that satellite imagery where you can sort of uh you're

able to purchase photos and and it's it's available to anyone right so it's like you it's a business side of it as well for seeing overhead shots and uh you gotta check it out skyfi.com it's very very cool uh that i'm helping with and then hybrid which got the hat on that's uh sort of like a more solver gto sort of friendly version though because like the po 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 especially 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 it'll give you like it'll

give you a game tree so it'll say 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 I'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 it's a really nice product so

yeah i've been helping with that working on that and uh just just staying busy man i had two kids and and it's been it's been hectic so i'm looking to relax you're stopping at two two's good my wife is good my wife turns 40 next week i'm 36 36, and I think that's a good number. A little cougar action there. Yeah. Exactly right. I don't think she's a cougar yet. It's, yeah.

No. Mount Lion. Mount Lion. No, not quite. Not that. Not quite there. Cougar would be 60. Yeah, no.

She's a mountain lion. No, she's young, man. She's young and fun. We met at Burning Man, and she's got a good spirit. It is a blessing to have kids, and yeah, just keep them busy. All right. Thanks for coming on, man, and she's got a good spirit. It's a blessing to have kids. Yeah, just keep them busy, man. All right. Thanks for coming on, man.

That was sick. Yeah, I appreciate it. Thank you. Thanks for watching, guys. Nice to meet you, man. I'll see you next time. Peace.