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A
You know, there's the whole 10,000 hour rule thing, which is just total BS. I think it's so much easier of any one thing you're interested in if you're obsessed with it. And again, you shouldn't do something if you're not obsessed with it. It's very, like, trivial to get into the top 1%.
B
Yeah. You debunked the 10,000 hour rule. You wrote a whole book about that one.
A
Yeah. And like, to some extent, it's true, you have to have some experience, but there's ways to quickly generate a lot of experience to kind of literally skip over a lot of those 10,000 hours.
B
Right. Mentorship. AI. Okay, guys, got James here, fellow podcaster with as many episodes as me, which is pretty rare, so thanks for coming, man.
A
Well, thanks for having me. It's really a pleasure. Been watching your show and I watch your show and I see how different things are over the past 10 years. Like, podcasts have evolved so much and you kind of focus right in on, you know, controversial moments and opinions, and it's always very interesting watching your show.
B
Yeah. I'm always finding new ways to grab attention. I feel like it's changing so fast that if you keep doing the same thing you used to, you won't be relevant.
A
Yeah, it's really true.
B
Right. Because you started 10 years ago. It was way easier to get views back then. Right.
A
You know, I admit it. It was easier because there were, A, there were fewer podcasts. B, there were fewer people that other people were interested in. C, there were fewer topics. Like, now there's lots of topics. There's, there's, there's more. Subcultures have keep dividing. It's like, it's like this mutant explosion of subcultures out there. And you could get like the peak of any one subculture, get tons of views from that subculture. And no one else knows who that is. But they learn through your podcast.
B
Yeah. These days, where are you directing majority of your focus? Because you've worn a lot of hats. You've been a chess player, comedian, you know, written many books, 20 books. Podcasting.
A
Yeah. So I always worry, like, I've been like a jack of all trades, maybe master of none, but I've been always doing entrepreneurial stuff, always doing writing stuff. Comedy was a passion for a long time, and I had a stand up comedy club and I toured around chess. I'm not like, you know, I'm not like the greatest player in the world, but I love playing and I travel all over playing and writing. About it. So I don't know. I'm just. I'm interested in a lot of things, but I'm always of the feeling that if I'm not going to be obsessed with something, it's not worth doing.
B
Yeah.
A
Because life's short.
B
Do you have one you're most proud about? Is it the chess? Because you're like top 01% in chess, in the world.
A
Yeah. But when you're top 0.1%, that's when you suck. So that's when I know how much better everybody else is than me. So, yeah, okay, there's 800 million people who play. So if you're in the top 1%, you're in the top 8 million. That means, like, maybe there's 8 million people better. Even the top 1% is 800,000 people better. So. So I. I suck compared to them.
B
Interesting when you put it that way. I always tell people, and I don't mean to sound arrogant, but getting into the top 1% isn't that hard.
A
No, I agree with you that. Look, let's say you love something, find something unique about it. And you could say you're in the top 1% of, let's say, the intersection. Like, for instance, if I were to take the intersection of chess and poker, I would be in the top 001%. Or if I was to say, oh, take the intersection between entrepreneurs and people who've written bestselling books, I'm in the top 0001%. So to get into the 1%, you just have to find the intersection of two things you love, put them together, you're the best. And even to get into the top 1%, there's the whole 10,000 hour rule thing, which is just total BS. I think it's so much easier of any one thing you're interested in if you're obsessed with it. And again, you shouldn't do something if you're not obsessed with it. It's trivial to get into the top 1%.
B
Yeah, you debunked the 10,000 hour rule. You wrote a whole book about that one.
A
Yeah, and like, to some extent, it's true, you have to have some experience, but there's ways to quickly generate a lot of experience to kind of literally, you know, skip over a lot of those 10,000 hours.
B
Right. Mentorship AI.
A
Yeah, mentorship AI. Now, like, AI wasn't even a thing a few years ago. Now it's the only thing, like, that's your mentor, really. Like, you could just use AI and you could become an Expert in anything.
B
Your mentor. It's your therapist, it's your health coach. It's. It's a lot of things these days.
A
While I was sitting outside in the lounge, my daughter was telling me the name of her ChatGPT. That's basically her friend and therapist now.
B
It gives really good advice, I'm not going to lie. Yeah. For personal stuff, I've tried it. What did you try for just like, mental health? I've tried it. Physical health is really good. Like, you can import your blood results, I can import my dental scans, run it through AI it determined, like, I had some cavities. It's really good.
A
What's like a mental health thing?
B
I don't know. Like, I've had quite the mental health journey, so I'll just ask, like, personal questions about relationships, how I can improve as a. I'm getting married in two months.
A
Oh, wow.
B
Congratulations. You know, I've been depressed, been lonely a majority of my life.
A
You know, I kind of think it's hard to avoid those feelings. Like, and I wonder how much, you know, let's say therapy or mental health works. Like, I've gone to therapists for many years and. And at the end of the day, after, like, a few sessions, I don't know how much more it helps and how much they're just sort of getting money from you.
B
I agree. I'm on my fourth session coming up here, and I can't say I'm too impressed. You know, I just started, so we'll see. I'll give it a fair shot, maybe 10 sessions, but I'm not too impressed so far.
A
But maybe, though, also, like, with anything with, like, with any career, you know, 99% of the people who practice that profession suck at it.
B
It could be that too. Yeah.
A
So, yeah, you kind of also have to find a really good one. But even then, I sort of feel it should be just used for very tactical reasons, like, oh, you know, my girlfriend just broke up. How do I get over this? Or, oh, you know, I lost my job, what do I do next? Or whatever. Like, just something very tactical as opposed to. Oh, in general, I have this feeling of malaise. How do I get over that? Like, that I don't think they're gonna solve.
B
Yeah, I agree. What's worked the best for you? Cause I know super intelligent people struggle a lot with mental health.
A
I don't think anything's worked for me, really. I mean, again, on tactical stuff, like, let's say someone leaves me or I, you know, then it's sort of like, very tactical. Like, you have to. You're incapacitated for a second, so you have to block and tackle on just living life. So you have to basically get out of bed and eat and move forward. And sometimes that's hard at the lowest points. But really, the main thing that's worked for me at my deepest depressions is when I am doing something for myself. Like, thinking will never get you out of thinking bad thoughts. You can't think your way into good. From bad thoughts to good thoughts. You have to do something, and then doing things will make you feel good.
B
I agree. I don't think you can think your way out of depression. Yeah, I. I've always distracted myself with work. I don't know if that's the best way to handle it, but.
A
Yeah, but what if you don't have work that. Cause that could be a problem too.
B
Yeah, that'd be tough if I didn't have, like a podcast or something to work on, like, all day, every day.
A
You know, like one time, this was the first time this happened to me. I went completely broke. I went. I had sold. I started off broke, which was. It was great. It's great when you're broke and you're starting things and it's going well. Being broke then is great. Being broke after you make millions and then you lose it all, that is like suicidal. That's the worst. And so I was so depressed. And what really helped me, I couldn't do anything. I could barely get out of bed in the morning. What really helped me was somehow or other, I convinced myself to basically get a waiter's pad every morning and write 10 ideas a day. And the idea being is that most of the time our idea muscle has atrophied. Cause it's a muscle like anything else. You have to practice it. You have to be creative with it. So I started writing 10 ideas a day down. And then suddenly I noticed after a week or two, I. I wasn't coming up with good ideas, but I was feeling good. I was feeling better because now my brain was doing something. I was exercising my brain, so. So. And then it got me to start sharing those ideas with people, and then I was doing something. And then, even though I was just as broke, I was no longer depressed and I was able to actually do stuff almost as if I was successful. Like, my brain did a complete reversal just by putting it to work.
B
That is interesting. So you were writing business ideas or.
A
Just any ideas, like, it doesn't even matter. And by the way, they're Going to be all bad ideas because your idea muscle has atrophied, so it takes a while to exercise it. But I was writing ideas for books I could write business I could start investments I could make. You know, I had no money, but I was looking at investment strategies and I was pitching them to hedge funds. This was like in the early 0. 0. It was like, oh, maybe you should try this strategy. Maybe you should try this strategy. I don't know. Ideas of things I could do with my kids who were babies then. Ideas of what I would do if I did go absolutely to zero. Like, I was losing my house at the time. You know, of course, when you're on the way up, everyone's your friend. On the way down, no one's your friends. I was also ideas of how to make more friends. I had zero friends at that point, so just ideas about anything.
B
Yeah, yeah. I struggled with friendships going up, too. I feel like as I've gotten older, the peaks and valleys have been really crazy for me. I don't know if you can relate.
A
To that, but, yeah, completely. Because if you're going for it, if you're trying for something unusual in life, you're going to have extreme peaks and valleys. Like, let's say, okay, you're just doing the 9 to 5 job and I'm not putting that down. Like, that's a fine path for many people, but your peaks and valleys are going to be different. You're going to have, like, office politics and that's going to distress you. But if you're really, like, trying to succeed at something that no. 1. If you're going for a frontier of some sort, like you want to be the best at something, you're going to fail, like, so much and it's going to be depressing and it's going to be like, did I just waste four years, three years, one year at something I really loved and now it's not working, or did I just make all this money and then that whole entire time I was making that money and working so hard, now it's got zero. Did I just waste that whole time? Like, those peaks and valleys are really depressing. And then, of course, there's the usual relationship stuff because that's going to happen alongside that as well.
B
So you.
A
If you combine those things, that's going to be the worst.
B
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A
Being an entrepreneur is not pleasant. Like, it's not like, oh, my God, now I'm an entrepreneur now. Life is great. No, you just. It just means your life is gonna suck now. Really bad for a good period of time, and you're never gonna stop working. It's 24 hours a day, and you're gonna get rejected. People are gonna laugh at you. People are gonna hate you. By the way, if none of these things happens, it probably means you're not really doing a good job as an entrepreneur. It probably means your business is not gonna work out if these things don't happen. But it's very unpleasant. And I think what it is, you have to get kind of relaxed with that unpleasantness, or it'll just consume you.
B
Yeah. Yeah. These days, I'm looking for ways to get some more fire under my belt because I don't want to get too comfortable.
A
Yeah. So. So, yeah, the question is, how do you get. How do you push yourself to get uncomfortable? You don't always have to push yourself. Like, you're doing a really great thing, so you don't always have to push yourself. But it's gonna happen naturally. You're gonna have an idea, oh, we should try this. And you're gonna really think it works. And maybe it will, maybe it won't, but it'll be a risk. But you don't have to take risks every day. Just, you know, when. When something occurs to you, you will.
B
Yeah. Well, after making and Losing all my money twice already at my age, I'm not as risky as I used to be, but I still, I'd still take some risks.
A
And, and look, being risk averse is both important and not important. Like, you have to know when to take the risks. So like someone who's never an entrepreneur, they'll never take risks. But an entrepreneur, if you take too many risks, you'll just lose all the time.
B
Right.
A
So you have to know if it's like poker, you have to know when you're gonna bet and take a risk that, okay, this is a calculated risk. This is a calculated bet that I'm taking. So you have to kind of get a feel for when it's calculated and you're still gonna be wrong some of the time. Like I would say in the past two months, I've, you know, made and lost millions. And I've also, you know, and, and maybe made again. And also I've had partners of 20 years backstab me. So these things always happen. Like, they never stop happening. And I've had, I have plenty of successful partners too, that I, that I love and are family to me. So it's, you know, it's a give.
B
And take, it's inevitable. Right. To have some business failures.
A
Yeah.
B
Partnership breakups.
A
Yeah. And they happen all the time. Like. And also you have to get a sense that most things that seem like they're going to happen won't. So most deals that seem like they're going to go through won't go through. And you just have to be comfortable with that.
B
Yeah. What have been the big losses recently? Was it like an investment or.
A
Yeah, or you think you're gonna, you go all in on a deal and it's just, it just doesn't work out, but then the other deals do. So you have to have diverse. For me, I sort of reduce risk by doing many things simultaneously. Like, I don't, I don't think I would risk my financial life on one business.
B
Right.
A
So I, I like to diversify, you know, my future fortune.
B
Do you believe in passive income?
A
No, not really.
B
Like even like a real estate property or.
A
I don't personally. I know people are successful with that. I, I don't like, I don't like the idea. I don't think I have any expertise in real estate, for instance. I don't think I have any expertise in any kind of passive income now. Okay. If you have like, for instance, subscriptions to a podcast, that's passive income. And if you work really hard on the Podcast, that could work out or a newsletter. People always want information of some sort and some of that information could be gated. So, so you. So it's a subscription. So I think that's a relatively low risk type of business, like a subscription media business. So I do diversify, for instance, into that as well. I have financial newsletter businesses, for instance. Yeah, so, so, so a little bit of everything is good.
B
How about staking crypto? Would you consider something like that, kind of passive, like dividends on a stock? Stock, Something like that?
A
No, because it's too small.
B
Too small?
A
Yeah, like if you're going to create wealth, 3% a year, no matter how much it compounds, is not even, even 10% a year is not gonna compound what you need. Look at the people who got wealthy on bitcoin. That's because it went from $10 to $100,000. That's not just compounding. So yeah, staking's a good idea for some types of businesses if you're like a hedge fund or a mutual fund and you need to generate consistent returns. Wall street prizes. Consistency and dividend yields or staking are good for consistency. But even like take Ethereum. Ethereum has, if you stake Ethereum, it's 3% yield. So people use more aggressive strategies. Like they'll, they'll, they'll stake their Ethereum, then they'll borrow cash against it to buy more Ethereum. They'll stake that. And that's a, called a looping leverage strategy where you can start to get like 15 to 20%.
B
Yeah. But you can get wrecked if the price tanks right.
A
Yeah, yeah, you're, you're, you're, you're screwed.
B
You get liquidated. Yeah, yeah, I see that.
A
It's called a looping strategy because it unloops also.
B
I love crypto though, to be honest. Yeah, me too. It's how I became a millionaire. I used to buy fake IDs with it in high school. I wish I kept all that. Oh my God. I would have been set.
A
In 2013, I released so there was a book I was writing. It's actually my bestselling book ever. It was called Choose Yourself. I released a book before it was the official release. I made a bitcoin only store that only accepted bitcoin and I sold a PDF of this book for about 1/10 of Bitcoin at the time. So. And about 60, 70 people use this store and use paid 1/10 of a Bitcoin for a PDF of this book.
B
Holy crap.
A
So made about 6 Bitcoin when it was $60 a coin then.
B
And you kept it all?
A
Most of it. So I used a little bit to pay for the developer.
B
Well done.
A
Yeah.
B
So you, you diamond handed it. That's what they call that.
A
And, and, and you know, bitcoin, everybody was, was laughing like, I, I would go on CNBC to talk about it. The anchors said, hey, did you just do this? And as a marketing stunt. And I said, well, look, I'm on national tv, so it worked like you had to do, you know. And you know who helped me come up with this idea was Ryan Holiday. Like back then, Ryan was a market and he still is, but he was focused on, he was a marketing genius. So he came with all these strategies and that was one of them.
B
I've talked to a lot of very smart people. They're convinced it's going to hit a million one day.
A
Oh, yeah, it definitely is. Like, look, here's one thing for sure, it's not going to stay at 100,000. It's either. Let's just looking at it from 20,000ft above, it's either zero or it's millions. And I happen to think it's useful. So it's going to be in the millions, but it's not going to stay here. Like, this is just a temporary spot. Like this is. And by the way, whether you like the President United States and his cabinet or not, the president owns billions of dollars of bitcoin. Six cabinet members own crypto and bitcoin. And, and these are the most powerful people in the world. They're going to make crypto go up that you can't. There's a saying, don't fight city hall. They're city hall and if you don't buy bitcoin, you're fighting them. So it's just like a stupid strategy to like, to bet against the thing that the most powerful people in the world all own.
B
Valid point. You pay a lot of attention to politics these days.
A
Not really, because it's so, it's so just stupid. Everyone's opinion. Like what's, what's like a good opinion.
B
I just feel like it doesn't affect people as much as they think. I know that could be kind of hard for people to hear, but, like, we're going to make money no matter what. We made money under, under Biden, we made money under Trump. Like, you know what I mean?
A
When was the last time. And look, for some people, they will have a real answer to this, but like, when was the last time you were personally affected by a Policy made.
B
By the president, United States, nothing major. Like when the car depreciation went from like 100% to 80%, I lost, like, 10K. But it's like, whatever, you know.
A
Yeah. And like, the tariffs affect you.
B
Not really. In the podcast space now, I know with. With luxury cars and even watches, it's affected their businesses.
A
Yeah. So. So, okay, so some businesses it affected temporarily. It doesn't affect them. They don't go out of business. Tiffany's is not going out of business. So it affects them a little bit, and then they figure it out, so. And they use marketing to make other things more attractive.
B
Right.
A
So. Or they start making stuff in places that are in tariffs that don't have tariffs. It doesn't really affect that many people. If you worked in Detroit, the change in that industry years ago affected those people. But that wasn't like, one president deciding, okay, we're gonna outsource all car manufacturing to China or Japan or whatever. That happened over a long time. It had nothing to do with politics.
B
Yeah. I think local politics matters way more.
A
Yeah. And then so I was talking to my daughters who live in New York City, and I'm like, who did you vote for for mayor?
B
Yeah.
A
And they both told me.
B
No.
A
They said, zoran. And I'm like, you mean Mamdani? And they're like, who's that? And so I'm like, well, Zoran's his first name.
B
Oh, my God.
A
And they're like, oh, we didn't know. And I'm like, well, how did you decide to vote for him? And. And they said. And they both said they were given a cheat sheet, and they just went down the cheat sheet and the cheat. She told them who to vote for on. On the ballot. So that's how most people, I think, vote.
B
That's crazy to me. So he's gonna win, it looks like.
A
Yeah. And I am glad he's gonna win because I want to see how screwed up these policies get. And then just once, although nobody ever pays attention to history, but you could say, look, this policy didn't work. You can't freeze rents. You can't freeze grocery prices. It's impossible. So, I mean, the Soviet Union, they tried it, and they all starved. China, what is it, 40 million people starved when they tried to freeze these prices. So we'll see what happens. New York City, we're both familiar with it from different periods of our lives. It's a hard city to run.
B
I just went back there to film at Spotify Studios. I still feel like it hasn't fully recovered. I know you went famous and viral for that article five years ago saying it would never recover, but I agree with you.
A
Yeah, it's really sad in that people, of course. Look, I wanted New York City to be successful. I want it to be successful. I was good friends with Eric Adams before he was mayor. I remember the first meeting when he decided to run for mayor was me and, like, three other people in the meeting. You know, I haven't spoken to him, actually. Maybe to his credit, he hasn't spoken to me since he's become mayor, but.
B
Wow, he cut you off.
A
I think so, actually. Like, I wrote an article supporting him. I liked him. He was over my house for Thanksgiving. He has not responded to me since he became mayor.
B
Do you think it's because of your article about how.
A
No, because we spoke afterwards and he actually wanted me to endorse him after I wrote that article. And I don't know what it is. Maybe he just didn't really like me that much. I don't know.
B
Well, I saw you on another show saying how you'll get along with these politicians on the show, and then they'll never hit you up after.
A
Yeah, no. Everybody's so charismatic, and I'm like, oh, my. Particularly like actors when they come on the show, and maybe you experience this. I'll be thinking in the middle of the episode, oh, my God, this is my new best friend. He's on my favorite TV shows, and now he's my best friend. And then I'll never hear from them again. I like. I'll say, oh, I'm in L. A now. You said reach out, and nothing.
B
It is a little disheartening because I feel like on podcasts, I'm pretty much myself. Maybe I alter at 5, 10%, but I'm genuinely myself. But some people just have a switch.
A
And they're completely different, and I got to admire that. They're so good at it.
B
So, yeah, so I got it. Yeah, I got to give them props because you would never know off camera if that's who they were or not. You know, it's.
A
It's an interesting thing because we went on an episode like, look, you meet somebody for the first time, and you kind of have to build rapport very quickly. You know, I did what I will call kind of an example of a podcast back in the 90s. So I used to do this website. I did HBO.com's website, so HBO, the TV network, and I pitched him on this idea. Hey, just like you have you know, gritty, original TV shows. Let's do a gritty, original web show for the website. They don't do this anymore, but they let me do whatever I wanted. So I did this web show called 3am about what happens in New York City at 3 in the morning, like, on a Tuesday night, a random night. And I had to get comfortable with just walking up to people at three in the morning in not necessarily the best areas, and just talk to them and find out what was going on in their lives. And so that helped me build up that skill that was useful much later on for podcasting.
B
Helped you build that confidence.
A
Yeah. Cause I was really not confident at all doing that.
B
Yeah. I don't think you can learn confidence in a book.
A
No.
B
Oh, no.
A
I mean, I don't think it's very hard to learn anything in a book.
B
Really?
A
Yeah. Like, what have you learned in a book?
B
I guess, directly, you still need to implement what you learn. So do you mean, like, it's hard to take action on what you learn in a book?
A
Yeah, like, okay, like, let's say a book about entrepreneurship. What are you going to really learn that? I mean, you really have to learn it on the job. Experience. Like, everybody already thinks they're a good judge of people. Yeah, most people are. I. I know for a fact now I am not a good judge of people. And I had to learn that from experience. Like, no book would have taught me how to be a good judge of people.
B
Fair point.
A
So.
B
Or, yeah, I could see that angle. I think books should be, like, supplemental. Like, you should learn through experience first and then supplement with books and podcasts. I don't think it should be the main thing because people read hundreds of books and they're not successful.
A
Yeah, right. Like. Like, you know, you could read books about sales. It's not going to tell you how to sell one thing or even, like, in a. You know, like, you're not going to read a book about tennis and suddenly be a good tennis player. You have to, like, swing the racket a bunch of times, so. Or chess. Like, we were talking about chess earlier. I study chess books all the time, but it's mostly now just for pleasure. Like, you know, as opposed to, like, learning something really new that's going to help me win a game.
B
Yeah, I've accepted that. I don't think I'll ever get past 1600.
A
You never know. Like, it's just a matter of, like.
B
I would have to spend money and hire a coach.
A
Yeah.
B
I'm saying, like, on my Own because I'm self taught from YouTube videos, I don't think. I think my peak is like 13, 1400, which is really good. It's decent. It's like top 5%. But unless I like devoted a lot of my life towards it, I don't think I do it on the side.
A
Yeah, you would only do it more than that if you loved it. Every waking moment when I was a kid, there was a period where every waking moment I had to play chess. I would not go to school for days or even weeks at a time just to play all day.
B
You were on the streets in New York City just hustling?
A
Yeah, yeah. Not necessarily hustling, sometimes being hustled. But I remember actually down the street from me there was this guy who was probably a little schizophrenic, like kind of on some spectrum. And I'm gonna say his name in a second, doxing him, but people already know this. And anyway, I skipped school. He had a PhD in math from Rutgers, but just was living at home with his parents. Cause that's what was going on. And he would just play chess all day. So I would just go over his house and we'd play chess all day. His name was John Nash III and his dad was the John Nash, so. So nobody knew who his dad was. Then it was just like, oh, I'm going over John's house and playing chess.
B
That's nuts.
A
Yeah.
B
That was your mentor, right?
A
He wasn't necessarily my mentor, but he was a little better than me. We would play in these like father son competitions together. Even though he wasn't my dad.
B
Adopted.
A
Yeah. And you know, we just had a fun time just analyzing the game and playing games all day.
B
And back then you didn't have the AI to analyze the games. Now I play a game on Chess.com. it shows me what I did wrong immediately.
A
Yeah. Now, now it's funny, which makes the game less social. Like you used to play games with people and then you could talk to them about it. Now I don't want to talk to you. I'm just going to go up to my hotel room and, and I'm going to analyze the game there. Like I don't care about your analysis, I just care about the computer's analysis.
B
Yeah. So I'm a fan of the mental side of sports. I consider chess a sport. Do you think table talk should be allowed a chess setting in a tournament?
A
Probably not, but definitely like in blitz and casual chess.
B
Yeah, I agree because I think that's an edge if you're good at talking, like, it could help you win games.
A
Oh yeah. Like in Washington Square park in the city as I was growing up, like that's how people would play. And you know, the mental side of chess. I was just talking about this with my coach, actually. The mental side of chess, it's gotta be at least 50, 60% of the game. Not necessarily like whether I'm gonna beat someone who's, let's say a beginner or whatever, but at my. If you're playing someone you're rating, then whether you win or not, 50 or 60% of that's gotta be mental.
B
Yeah. Cause you're the same skill level.
A
Yeah.
B
So what separates you?
A
It could be some piece of knowledge, you know, that the other person doesn't. But let's say you start losing. There's a difference between the kind of person who really kicks in when they're losing, and this is true for business too. The kind of person who kicks in when they're losing and the kind of person who says, oh, there I go again, I'm such a loser. Like that will affect whether you see certain moves later on in the game. Like last tournament I played in and my coach was so upset at me, he's like, look, every single game you had a winning move after you were losing and you didn't see any of.
B
Them because you just shut down.
A
Yeah. Just shut down. So I lost like, you know, most of my games because I was just like self talk. I couldn't get out of the self talk. And I try really hard. Like I know how important mindset is, but for whatever reason, this, this particular tournament, it didn't kick in at all.
B
That's interesting. I wonder if that's like a. Because a lot of the stuff I'm learning now comes from childhood. Like all your traumas in adult life. So I wonder if when you were growing up you had some self doubt issues or something.
A
Probably. Yeah. Yeah. And I mean, I remember again I took a break from playing chess for something like 25 years. So I played as a kid and then as soon as I hit like the master level, I stopped because I knew this was going to be good for business. Like, it's good because it has. Chess has such a cultural impact. It's good to be able to say, oh, I'm a chess master also. Like, there's always some effect. And so I stopped playing completely. And then more recently, I've started again like an idiot, thinking I'm gonna be as good as I was then. And you know, I would though I wouldn't be if I lost a single game in a tournament when I was a kid, I wouldn't be able to go to school the next day. Like, I was so upset at myself and I probably never really got over that feeling of just being disappointed in myself with a loss.
B
It's interesting. I'm very hard on myself too, and sometimes I wonder if that's good or bad.
A
I don't think it's that good. I think it's, it's good to analyze and to be self critical, to not think, oh, he just got like, I never think to myself, he just got lucky. Like that's the worst thing of, of, of optimism in the other side. But, but you, you have to just say, okay, that was a learning experience. And, and I'm going to really dissect. Like for instance, I used to do, I owned a stand up comedy club for a while and I would do stand up comedy almost every night for years and I would take a video of every single time and I would look at it and particularly when I did poorly. And then you say, oh, okay, this is why they didn't laugh, or this joke's not funny, or I said too many ums and ahs or I, or I spoke over the laugh so I couldn't really get to the real punchline. And so you see, you have to analyze the things you do. Even in business. You have to analyze postmortems or investments. You can never. The worst words are to say, oh, I just got unlucky or the other person just got lucky.
B
Yeah.
A
Like then you ruin it.
B
Wow. So that actually worked with comedy though. You felt like you got better doing.
A
Oh yeah, because then you know which jokes a, which jokes work and which don't. You know, Oh, I wasn't taking care of this part of the audience, like this part of the crowd. I was focusing too much on this part of the crowd. This part of the crowd were ignoring me. And so I, I didn't sense that during the, during the performance or I talked too fast during this one part or I didn't really commit to the joke. Like you could see I'm nervous. In comedy, the audience is an X ray machine and they know when you're just performing as opposed to saying something real to them.
B
Right.
A
So if I could see that in my videos of myself, then I know the audience could see it. So you have to really analyze.
B
That's interesting because to me I always thought being funny was like something you had or not. But you're saying you trained it?
A
Oh, yeah. Cause I, you have to. Okay, like being funny, maybe that is something that's either natural or not. But for comedy, there's so many other skills too. There's, there's storytelling, there's how you move your, your voice. There's how you play with the crowd. There's how you use the mic, how you play with the stage. Like, there's, there's all these other, what I call micro skills.
B
Got it.
A
Like, like it's like business too. There's no one skill like, oh, I have business skills. There's sales, marketing, management, product execution, you know, all sorts of other. You know, there's, there's raising money. That's an entire skill. There's, there's how you value your company and your efforts. That's a skill. So there's all these like subskills to business. You know, writing's the same way. There's, there's skills with storytelling skills with your, the actual poetry of your words. There's skills with, you know, how do you structure an idea, how you weave an idea through a story? So there's all these different sub skills and every, all these things that people think are mega skills are really just, you know, collections of micro skills.
B
Yeah. And do you recommend when people are starting out to learn one skill at a time just to hone in on one?
A
Yeah, absolutely. So I'll give you an example which is, which is kind of a frowned upon example, but one of my daughters was going to do an open mic just for fun. And so I said, here's what you should do, and no one else is going to give you this advice is steal a bunch of jokes from your favorite comedian and, and then do those jokes because then you've isolated. You know, the joke works. So that part you've isolated. And now you can see if your performance skills, what aspect of your performance skills need to be better. But if you just go up there and try to write your own jokes and you're. The first time you're going up there, you won't know which part is bad. You don't know, oh, you need to be a better joke writer. You need to be funnier. You need. Or is it, was it just something you did in the performance?
B
Yeah.
A
So you won't be able to isolate the skill.
B
That's definitely a hot take because I know comedians hate when you take their jokes.
A
Yeah, yeah, no. And I don't think any comedian would give that advice. But that's why. Okay, let's say You're a public speaker. Do the same thing. Steal, like, jokes from your best comedian. And I'm not saying do this every time. I'm just saying as you're getting better, as you're developing the skill, you want to be funny. Don't worry about the joke part. There's so many other parts that you need to work on.
B
Also, did you know public speaking is the number one fear in the world?
A
Yeah, I think Jerry Seinfeld has the joke where he says people are more afraid to be speaking at the funeral than to be the dead person at the funeral.
B
Yeah, it's so weird to me, but I think it kind of makes sense because, like, being in public school, I hated it. So I think you're kind of low key, taught to hate it growing up.
A
Yeah. And also, I think it's an evolutionary thing. Like, you know, if you're seen as weak in the tribe, they might kick you out of the tribe and then you're dead. So in public speaking, you're exposing yourself completely and you could be seen as weak. So it's just. That's why it's this prime. Almost like fear, like death, I think. I think it's this evolutionary thing.
B
Is that why you wanted to get in comedy? To get over that fear?
A
I just loved comedy, but, yeah, I was so afraid. So actually I was doing a podcast with Stephen Dumer, one of the authors of Freakonomics, and we challenged each other to rent out a hall in New York City and do standup for five minutes each. And we did it. And I was so scared I wasn't even going to show up. Like, I was literally like, you know, I couldn't handle it. But then I did it, and I thought to myself, oh, my God, that was just the best thing ever. And so I got obsessed. And I would say for the next five or six years after that, that's all I did, was stand up comedy. Like, all day I would watch comedians just to learn. And then at night, I would find different comedy clubs who would let me perform. And then until eventually I bought a comedy club, which is the worst investment ever. And then I would do it every night, and I sucked for a long time. And then I would say, I got mediocre. I got good enough where I could. Like, other clubs would ask me to perform around the country. I did some stuff internationally. Like, I got okay, not, like, great.
B
Yeah, you got top 1%.
A
Yeah, I got top 1%.
B
It's pretty good in comedy. Yeah, because in comedy, apparently you got to devote 10 years, they say, oh.
A
Yeah, I would say look at all the comedians that are even like the next generation after. Like let's say the Louis CK's and Chris Rox, like let's say Andrew Schultz, Chris Di Sapphano, Theo Vaughan. I would say they're. They're the next generation after. Like Louis C. Hate, Chris Rock, all of them. A minimum. You only heard about them after they were doing it for about 15 years.
B
Yeah. And that's amplified even faster because of social media too.
A
Yeah.
B
If they didn't have that, it would have taken probably 20, 30 years.
A
And podcasts also helped them. Like take someone like Tim Dillon. He. He was already like a great comedian, but nobody knew who he was. He was just like a local comedian in New York City. But the podcast really put him above the top.
B
Yeah. I think comedy podcasts are number two out of every category.
A
Yeah. And I would bet there, I mean, what's first is like true crime.
B
True crime.
A
Yeah. So I would bet you that true crime during the pandemic, maybe comedy probably tipped to number one a little bit. And then, you know, but because Joe Rogan's a comedian as well and so. But like the Ovan, Chris Dufano, Tim Dillon, they're great podcasters and it's because of their comedy skills.
B
What show is your category in?
A
I don't even know because I just.
B
What category is your show in?
A
I said that backwards. I think it went back and forth for a while between business, but then they realized I hardly had any businessmen on and then it would be in like self help. But I wasn't really. I wrote books that were categorized in the self help category and. And I kept trying to tell people I'm really more self hurt, but. But you know, it became self help. So I was. It goes back and forth between those.
B
Categories in those two too. I started with marketing business, self help. Now I'm in education. I don't. I have so many different guests, it's hard to.
A
Yeah, same with me. It's more general.
B
Yeah, it's more like who do I think is interesting. Yeah, that's exactly what I promise of my show.
A
Do you ever worry that that makes you too general?
B
I do. It is an issue because some people say to niche down, but I'm doing this for fun. Like the pot. It makes good money too. But like I don't care about sponsors or whatever. I've lost a ton of sponsors. I've lost guests having on controversial people. But it's part of the game.
A
Yeah. You know, it's so funny. Like people when you have controversial people on. Like, I think you and I both have had. Like on Andrew Tate, for instance. Okay, who, who cares that I spoke to somebody for 45 minutes or an hour? You know, if you don't want to listen to somebody, just shut. Don't listen to that episode facts. But don't judge me. Like, I'm not giving an opinion. Even if I gave an opinion, who cares? Like, I have some good opinions. People like some. They don't. Like, everybody hates each other now.
B
No, it's very divisive. And the argument I hear is like, why are you platforming this person? Yeah, but I don't like that argument because half the time they have a bigger platform than me.
A
Right.
B
It doesn't even make sense to me.
A
Right. Like, yeah, I'm really, you know, delivering Andrew Tate's message to the world. Like, thank. He should thank God for me because finally now the world hears who he is.
B
Yeah, yeah, I don't like that. I'm big on free speech. Like, you decide how you feel. But why do you have the need to mass report my account? Like, I'm banned on TikTok right now.
A
Oh, I didn't know that.
B
Yeah, lost it last month trying to get it back. But yeah, politics is a very. People just report you if they don't agree with you. So.
A
Yeah, and like, what was it would, you know what, what was it that.
B
It was the Israel stuff, you know.
A
Yeah.
B
But the thing is, I have on both sides, but if one side only sees one certain clip, they'll just mass report it, get my account banned.
A
I mean, and look, that's one of those issues too, where there's. By the way, there's a million war situations happening around the world, but everyone is like fixed on that hyper fixed one war situation. And probably like people on, on every side have some degree of misinformation, so it's hard to really know what's truth. The history is very complicated. If you say, oh, this started here. No, really, Someone else could say, no, it started 10 years earlier. And so. And then no one's ever gonna agree. No one's gonna change their mind. So you're not. So what's the point of. You know, I could see if somebody says, you know, death to all this group or death to all this group. That's extreme. But you know, for everything else, it's just, it's just kind of. I don't wanna say it's entertainment. Cause that makes a mockery of it. But I Don't know. It's just hard to really know.
B
Well, political commentary has turned into entertainment at this point. There's no doubt. Like, if you watch Piers Morgan and you watch some of these political commentary shows, it's just a screaming match. It's just, like, stirring up drama.
A
Yeah. And like. And again, who are they convincing? Like, what good are they doing in the world?
B
Yeah. So I think politics is. I think many people focus on it, and it's not worth the time they're putting in.
A
Like, I sort of Ms. 2012 in the sense that Barack Obama and Mitt Romney, they were the same person, actually. Pretty much like, they're like, you know, the issue was Obamacare, but Mitt Romney was the one who was the test when he was governor of Massachusetts. He created Romneycare. It was the same thing. So they were not really different. Nobody was gonna stop any war that was going on. They were both in favor of all the wars that were happening. And so there were. So it was sort of like a pleasant time to focus on other things other than politics.
B
I agree. I think when Trump ran the first time, he just brought a whole new set of eyeballs into the politics. Right.
A
And. And. And look, he was funny. There was a little different.
B
That's what won him the election.
A
Yeah, exactly. And, you know, people like. Like, oh, okay, this stands out. It's not just like every single other person saying the exact same thing. So it was funny, it was entertaining, and that's what it still is.
B
Yeah. Are you still in Jersey? I know you were growing up in North Brunswick.
A
Yeah, no, I'm. I lived my whole adult life in New York City. Most recently, though, I've been living a little outside of Atlanta, Georgia. Just wanted to.
B
Wanted some.
A
Yeah.
B
Some land.
A
Yeah, some land. I didn't want to smell things all day long.
B
There's, like, studies on life expectancy. Have you seen these?
A
No.
B
For people that live in major cities, especially New York, it's, like, a few years lower than the average. That's really interesting, all the pollution and I guess the. I don't know if you believe in this, but, like, the WI fi and the 5G towers and all that stuff.
A
I would believe that the pollution, because it really does smell different in New York City. So, like, I would believe that. And of course, I would also believe. I don't know how crime is related to, like, nobody gets murdered in my town. Oh. At now. So some. Some might be. Some of those statistics might factor in, like, murders, although there really isn't that many murders. And there's more just like violent crimes more than murders, but. Yeah, but you know what? Here's the thing about New York City, though. It's very stressful. It's a hard place to live. Like, you can't. You can't live in a nice apartment, for instance, unless you have a lot of money. It's just a fact.
B
Yeah. It's like 10k a month, right?
A
Yeah. Like, to get an acceptable apartment is like, almost minimum that otherwise you're gonna have roommates or it's a little too small for you and your wife and two kids. And so, you know, and I think also it's a very transactional city. Like, like, everybody. Because it's. Everybody's hungry there. It's. It's if. If you. If. If you do something for everybody's. Doing something for everybody else, but it's in a very transactional way, which I. Which I didn't like.
B
I think that's most cities these days. Right. Because that could be it too.
A
Yeah.
B
Yeah. My. My plan is to, like. Because obviously we need to be close to a major city for what we do with the podcast. So my plans to, like, to have a getaway and just go back and forth when I. Oh.
A
The funny thing is, Las Vegas is like a getaway. Like, if you go outside again, you've got the beautiful desert, like, minutes from here.
B
Yeah. Yeah, it's pretty. I like Vegas a lot, honestly. It's hard to be Vegas because you get good bang for your buck out here too.
A
Yeah. Oh, yeah. Even, like, staying in hotels and stuff is like one third the price of New York City.
B
Yeah. I do a staycation every three months. There's so many hotels out here, man. Which one are you at?
A
I'm at the. I think it's pronounced Vera Verdara. Verdara.
B
Yeah. Next to Aria.
A
Yeah. I didn't want to stay at a casino, so I got a gambling addiction. Well, I used to play a lot of poker, and I just don't want to be any. I'm just not interested at all being tempted by anything.
B
Did you get wrecked?
A
No, I. Actually, it was one of those things that I got obsessed with. So I did the usual things I like, I. It was the only thing I could function at. Like, I would do it all day long. I would study it. I would memorize out all the statistics. I had a coach. And then all night, from 8pm to 4am, every single night, I would play like 365 straight days, like a year. And my. My wife would even tell her friends, look, at least I know where he is, and he's not, like, cheating or something. So she didn't mind. And I would say, again, it was one of those things where at first I was bad, and then I got probably pretty good, you know, again, good enough that I could. I could handle myself in Atlantic City. Couldn't quite handle myself in Las Vegas, but I think Las Vegas had the best players in the world.
B
We still do right now.
A
Yeah. And so. And you have to be very honest with where your skill set is. Probably if I kept working at it, it would have been good. And then what really got me wrecked is I decided to be an entrepreneur again. And then. Then I got wrecked.
B
Got it. So poker is a very interesting game because you could be really good but still lose.
A
Yeah.
B
Like a lot of money.
A
Yeah.
B
You got to pick the right games. You know what I mean? You can't let your ego get in the way.
A
Yeah. Like, I. You know, there's a great player, Gus Hansen, who went all the way to tens of millions, all the way back down to zero, I think. I think he's like an accountant somewhere now.
B
And that's common with a lot of the poker guys.
A
I want that. And that's really the depressing part about losing money. It's better to not have a lot of money than to have it and then lose it, because it's hard to go back to where you were once.
B
You get a taste of it. Because I grew up pretty, like, broke, honestly. Like 0 to 20.
A
Yeah.
B
Just relying on my parents. And then I didn't. I wasn't depressed. I mean, I was, but that was college. I was different. But then when I lost all my.
A
Money, that's the worst.
B
That was rough.
A
Yeah. Like. Like when I was. When I first, as an adult, moved to New York City, then you're hungry, then you're curious, then you're finding out where all the opportunities are. And then as you're growing for the first time, it's like, oh, my gosh, I could. I could buy a vacation. I could buy a television set. Like, I could afford these things. And it feels so good. There's so much dopamine. And then you get clients, your universe expands. You realize, oh, I could actually be successful. And you believe in yourself at that point. And then the first time you lose everything and happens to everybody. First time you lose everything, it's just the worst feeling in the world. You feel like you won the lottery, and you're never gonna be able to win the lottery again. And you don't know how you're going to get out of it. And now, at the very least, I've gone. I've made money and gone broke so many times that I. Even though it's still depressing, I tell myself, okay, I know I've been here before. I know I'm going to get out of this if I just stay positive.
B
Because you got the skill set and the mindset.
A
Yeah. And I have to remind myself of it because it still feels depressing.
B
Yeah.
A
And I still have to tell myself I've got to do things. I've got to keep writing these 10 ideas a day, keep it healthy, you know, everything. Like now I'm in the Olympics, because now if I don't do everything right, I'm going to just stay broke. And so that's what keeps me going. But I know I can do it again. Like, there's three skills to money. There's, there's. And they're completely different skills. There's making it, keeping it, growing it. So for a long time, I realized I was good at making it, but I was horrible at keeping it and growing it.
B
What do you think's the hardest out of the three?
A
I don't know, because I think in general, people think making it is the hardest, but for me, keeping it was. Was really hard.
B
I agree. I think making it for me is the easiest, but for most people, it's the hardest.
A
Yeah. Because you have to, like, you have to know how to do things. You have to know you have to have some talent at doing things, and then you have to get very quickly good at the things that you're bad at or at least know what you need. Like, for instance, I know I'm a poor judge of people, so I don't. I don't try to make decisions based unless I have a second or third opinion on the people I'm doing deals with. So you have to know where you're weak so you could, you know, try to get stronger at it or at least hire for that.
B
That makes sense. And then keeping it, that's just a matter of controlling your. Your vices.
A
Yeah. And. Yeah. And understanding risk, too. Like, I would take enormous risks that I should not have with. With money. With. With money that I had worked really hard to make.
B
Right.
A
So you can make some risk. You have to. But. But I can't take too much risk.
B
Yeah, that was my issue, too. I invested all over the place and stuff I knew nothing about. That's how I lost it.
A
Right. People think it's like, oh, did you spend money on, like, drugs and hookers? No, it was really just trying to. I had 10 million. Trying to make 100 million is the mistake I made.
B
I've never been able to make that jump.
A
Yeah, no, I. I'm. You know, without saying too much, I have not been able to make that jump either.
B
I don't. I also think the jumps don't hit the same, if that makes sense. Like, 0 to 100k was crazy. I felt like a baller, like in college, making that money. A hundred K to a million felt really good. A million to ten was. Was. All right. But, like, now I feel like money's kind of lost its. I don't know how to word it.
A
Yeah, I mean, now it's. Right. Because that's why you could. That's why now. First off, when you have a good number, it's easier to make and lose millions, and it's not gonna affect you as personally. Although I try to have it affect me so that I still feel that hunger. And I always remind myself of other people who I'm responsible for and other obligations I have. And usually you're not in a world by yourself. Let's say you make a lot of money on a business. There's employees, there's investors, there's customers, and you're doing something for all of them. They all depend on you. So I try to. I try to always make the stakes very high.
B
I like that. Yeah. When I used to, like, I guess, make money, it impacted my lifestyle a lot, like when I was first buying a house and doing all that stuff. But now when I make more money, there's not much I can buy that's going to change my happiness and fulfillment. You know what I mean?
A
When you first made a lot of money, how were your relationships?
B
Really bad. Really terrible. Yeah, because I was all in on making money. I was obsessed like you were.
A
Yeah. And then. And then. Did you lose a lot of relationships?
B
Yeah, tons. Now I'm, like, rebuilding them, I'd say.
A
Yeah. I feel like that's always a process for me because also along the way, different people, they react to you and they don't really know why they're reacting to you. But a little bit is obviously jealousy and a little bit might be their own personal frustrations. And also sometimes if you're always the hero for somebody and then suddenly you're distracted and you're not the hero for them anymore, that they could get very disappointed.
B
Yeah. Yeah. I sacrificed a lot to get early success relationships. My Physical health was shit. My mental health was awful. I wouldn't recommend it, honestly, for most people. I barely made it through the er. Like, it was. It wasn't fun.
A
Yeah, it's not fun.
B
I had panic attacks all the time.
A
But what is worth it? That is also fun because let's just take even like, you know, something trivial like stand up comedy or playing a game or I'm not going to say writing a book, but they're not. None of these things are fun. Like, getting great at something is not fun.
B
Valid.
A
There's pleasure in improvement and there's ple. My problem is I think I don't know how to enjoy things unless I'm improving. I kind of have to get better at enjoying things just for the sake of it.
B
Same. Because I think if you're not improving, you're declining. So for me, I have to constantly be improving.
A
Yeah. Or else it kind of loses flair. But I'm. I'm told that's a big mistake in life.
B
It gets to a point where you can't improve because you're so at the top that in order to improve you would have to like go even more all in, you know?
A
Yeah.
B
So diminishing returns, I think that's what they call it.
A
Yeah. And it's. And that's painful.
B
Yeah, it is.
A
I mean, think of these guys. We were talking earlier about the top 10 in tennis, and I know this for a fact. Like, let's say in the top, let's say 10 or 20 in the chess world. Unless you're like the number one guy, you know, which is Magnus Carlsen. The rest of them are all, I would say, mildly depressed.
B
Yeah. Because they don't make money.
A
Yeah.
B
And.
A
And also they're just, they're so great. Like, they're the best in history by far. And yet they're not the best.
B
It is crazy, that comparison game that we all play. And social media plays a role in that too, I think. Yeah.
A
Like, look, social media is so hierarchical that, you know, and look, every day I'll do it, like two people follow me. Okay. I'll follow the person back with more followers. Like, it's just very hierarchical. And, and so that's. If you, if you really like. I remember in like let's say 2010. So I'm a bit older when I was really first trying to get followers on social media. And I would say I'm not as obsessed with that now, but if there was a day where I didn't like increase followers, I would be getting a Little depressed. So even though it's so not important. Yeah. But then later on it's like not important to me now, so I'm glad.
B
It'S lost meaning, to be honest. Followers only matter now for getting DMs, but they don't matter to get views, so.
A
Yeah, because the algorithm now is better.
B
Yeah, it's way better. I love it. I get more views from non followers on my show.
A
Yeah. And when you're looking on your feeds, do you ever look at the for you or do you look at. Or you don't look at the followed you look at the for you, only for you.
B
Yeah, I don't want to see people I'm following post. What the hell.
A
Yeah, exactly. Like I already know what they do.
B
Yeah.
A
And they're not superheroes. I'd rather look at the super. The Gen z superheroes on TikTok.
B
They're just posting their highlights. Oh, you had an interesting take on Gen Z. So you think they're the most superior generation by far.
A
Like, I can't believe every day when I look at social media like, like let's say Instagram, you see anything like a skateboarder, like skateboarding off of a mountain, doing a flip and then potentially dying or landing. Exactly right. I mean, do these people die or. I don't think they're all fake. Like, I think some of these people are like amazingly skilled.
B
Yeah. Rarely. But yeah, there's some pretty insane videos. I think it's a very talented generation. I know they get a lot of hate, but.
A
And like if you see like on music, like piano, for instance, there are some of these Gen Z kids are so amazingly talented and skilled or you know, anything. Like any skill you could possibly think of is. Gen Z already has the. It used to be that older people were the best in the world. Now the Gen Z, there's somebody who's Gen Z, who's the best in the world at almost every skill imaginable. I would even say like math or physics, like some. Something that you wouldn't expect. You need to be a little older. It's already. Gen Z is already somebody. Gen Z is already the best in the world at it.
B
Yeah, I think it's the access to information because it's so easy to learn these days.
A
And maybe they're better at learning too, like just learning quickly because they got. They're so used to it.
B
Well, I know I am now with AI. I'm learning so fast these days.
A
Yeah. If you're interested in anything with AI and if you're the great thing with AI is you don't have to be embarrassed about any questions that you ask. You could ask the stupidest questions in the world. Like, look, I've been talking about bitcoin and doing crypto stuff for. Since 2013, and the other day I asked AI, hey, can you explain to me again what blockchain is? Like, you could ask just the dumbest question. You don't have to be afraid. Like, hey, weren't you supposed to know that already?
B
No judgment.
A
No judgment.
B
Yeah, that's a good point, man. Well, James, this has been super fun. I can't wait to do another episode with you one of these days. Where can people find your show and everything?
A
James Altucher show, you know, or listen to me here on Sean's excellent show. So anywhere you want to buy me, you can find me.
B
We'll have to play chess, but you can't start with a queen to make it fair.
A
How about I'll do blindfold?
B
Oh, that'd be fun. Let's do it.
A
I've been practicing that, lady. That's my training now. One game a day. Blindfold.
B
Let's do it. All right, man. Check them out. See you next time. Peace.
A
Thanks.
B
I hope you guys are enjoying the show. Please don't forget to like and subscribe. It helps the show a lot with the algorithm. Thank you.
Episode: Why Gen Z Might Be the Most Talented Generation in History | DSH #1645
Host: Sean Kelly
Guest: James Altucher
Date: November 28, 2025
In this engaging episode, Sean Kelly welcomes entrepreneur, podcaster, writer, and chess enthusiast James Altucher for a candid conversation about personal growth, overcoming adversity, and the evolution of talent across generations. The discussion weaves through topics like mental health, entrepreneurship, failure and resilience, the impact of AI and technology, financial wisdom, and Altucher’s bold take on why Gen Z might be the most talented generation ever.
The dialogue is refreshingly unfiltered, with both host and guest sharing vulnerable moments, lessons from hard-won experience, and unconventional advice for navigating an ever-changing world.
This episode is a blend of practical wisdom and raw honesty about the real costs of achievement and reinvention. James Altucher’s unconventional advice, humility about personal failures, and genuine admiration for the next generation make this a must-listen for anyone interested in entrepreneurship, personal growth, or the evolving talent landscape.
Find James Altucher:
Memorable Closer:
“We’ll have to play chess, but you can’t start with a queen to make it fair.” – Sean (52:41)
For those seeking inspiration, comfort, or provocation, this conversation delivers on all counts.