James Altucher: Why Gen Z Might Be the Most Talented Generation in History | DSH #1645

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 trivial to get into the top one percent.

Yeah, you debunked the 10,000-hour rule, you wrote a whole book about that one. 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, 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.
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. 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. Yeah, it's very, really true.
Right. Because you started 10 years ago.

It was way easier to get views back then, right? 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. Yeah.

These days, where are you directing a majority of your focus? Because you've worn a lot of hats. You've been a chess player, a comedian, you know, written many books, 20 books, podcasting.

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 it. 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. Yeah.
Because life's short. Do you have one you're most proud about? Is it the chess?

Because you're like top 0.01% in chess in the world. 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%, there's 800,000 people better.

So I suck compared to them. 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. 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 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 have written best-selling books, I'm in the top 0001%.

So if you, to get into the 1%, you just have to, you know,

find the intersection of two things you love, put them together, you're the best. And even to get into the top 1%, 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, it's like trivial to get into the top 1%.

Yeah, you debunked the 10,000-hour rule. You wrote a whole book about that one.
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.

Right. Mentorship, AI.
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 become, you could become an expert in anything. It's your mentor, it's your therapist, it's your health coach.
It's, it's a lot of things these days.

While I was sitting outside in the lounge, my daughter was telling me the name of her chat GPT. That's basically her friend and therapist now.
And it gives really good advice. I'm not going to lie.

Yeah. For personal stuff.
I've tried it. What did you try it 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. What's like a mental health thing?

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.

Oh, I'm not a lot, you know. I've been depressed, been lonely a majority of my life.
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 therapist for many years.

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. 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.

But maybe they'll also, like with anything, with like with any career, you know, 99% of the people who practice that profession suck at it.

It could be that too. Yeah.
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 going to solve. Yeah, I agree.
What's worked the best for you? Because I know super intelligent people struggle a lot with mental health.

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, you're, you're, 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. I agree.
I don't think you can think your way out of depression. Yeah.

I've always distracted myself with work. I don't know if that's the best way to handle it, but.
Yeah, but what if you don't have work? Because that could be a problem too.

Yeah, that'd be tough if I didn't have like a podcast or something to work on like all day, every day, you know? Like one time.

This was the first time this happened to me. I went completely broke.
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.

And because it's a muscle like anything else, you have to practice it. You have to, you have to be creative with it.
So I started writing 10 ideas a day down.

And then suddenly I noticed after like a week or two, 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 some stuff almost as if I was successful. Like my brain did a complete reversal just by putting it to work.
That is interesting.

So you were writing business ideas or just any ideas. Like it doesn't even matter.
And they're, 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 00s, like, oh, maybe you should try this strategy.

Maybe you should try this strategy. I don't know, ideas to 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 friend. So it's also ideas of how to make more friends.

I had zero friends at that point. So just ideas about anything.
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 to that, but.

Yeah, completely, because if you're 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 let's say okay you're just doing the nine to five 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 one you 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.

So if you combine those things, that's going to be the worst.

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Entrepreneurship, I know it's glorified on social media, but it's a tough lifestyle, man. Even if you're at the top, like you, you go through some shit.
There is not

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 going to suck now really bad for a good period of time. And you're never going to stop working.
It's 24 hours a day. And you're going to to get rejected.

People are going to laugh at you. People are going to 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 going to 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.
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. Yeah.

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 going to happen naturally. You're going to have an idea.
Oh, we should try this. And you're going to 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 something occurs to you, you, you will. 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. 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. So, you have to know, it's like poker.

You have to know when you're going to 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 going to be wrong some of the time. Like, I would say, in the past two months, I've

made and lost millions. And I've also, you know, 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 love and are a family to me. So it's, you know, it's a give and take.

It's inevitable, right, to have some business failures, business partnership breakups. 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 seem like they're going to go through won't go through.

You just have to be comfortable with that. Yeah.
What have been the big losses recently? Was it like an investment?

Yeah, or you think you're going to, 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.

So I like to diversify, you know, my future fortune. Do you believe in passive income? No, not really.

Do you even like a real estate property?

I don't personally. I know people are successful with that.

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

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 how about staking crypto?

Would you consider something like that kind of passive like dividends on a stock stock something like that

No, because it's too small too small yeah like if you're gonna create wealth 3% a year and no matter how much it compounds is not 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, you know, $10 to $100,000. Like that's not just compounding.
So, so yeah, staking is a good idea.

If you're, for some types of businesses, if you're like a hedge fund or a mutual fund and you need to generate consistent returns, you know, the Wall Street prizes consistency.

So, 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 stake their Ethereum, then they'll borrow cash against it to buy more Ethereum. They'll stake that.
And that's called a looping leverage strategy where you can start to get like 15 to 20%.

Yeah, but you don't get wrecked if the price tanks, right? Yeah, yeah.

You're screwed. You get liquidated.
Yeah. Yeah, I see that.
It's called a looping strategy because it unloops also.

I love crypto, though, to be honest.

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.
In 2013, I released, so there was a book I was writing.

It was actually my best-selling 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 one-tenth of Bitcoin at the time.

So, and about 60, 70 people used this store and paid one tenth of a Bitcoin for a PDF of this book. Holy crap.
So I made about six Bitcoin when it was $60 a coin then. And you kept it all? Most of it.

So I used a little bit to pay for the developer. Well done.
Yeah. So you've, you diamond-handed it.
That's what they call it. And, and, and, you know, Bitcoin, everybody was, was laughing.

Like, I will, I would go on CNBC to talk about it. The anchors said, hey, did you just do this 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 marketer, 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.

I've talked to a lot of very smart people. They're convinced it's going to hit a million one day.
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 20,000 feet 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.
And, 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 of the United States and his cabinet or not, the president owns billions of dollars of Bitcoin.

Six cabinet members own, you know, crypto and Bitcoin. And these are the most powerful people in the world.
They're going to make crypto go up. 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 bet against the thing that the most powerful people in the world all own. Valid point.

You pay a lot of attention to politics these days? Not really, because it's so, it's so just stupid, everyone's opinion. Like, what's like a good opinion?

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 Biden.

We made money under Trump. Like, you know what I mean? 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 by the president of the 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? Yeah. And like, do tariffs affect you? Not really in the podcast space.

Now I know with luxury cars and even watches, it's affected their businesses. Yeah.
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.

So or they start making stuff in places that aren't 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 going to outsource all car manufacturing to China or Japan or whatever. That's that happened over a long time.

It had nothing to do with politics. Yeah, I think local politics matters way more.

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?

And they both told me, um, uh, Mamdani. No, they said Zoran.
And I'm like, you mean Mamdani? And they're like, who's that?

And I'm like, well, Zoran's his first name. Oh, my God.
And they're like, oh, we didn't know. And I'm like, well, how did you decide to vote for him?

And they said, and they both said they were given a cheat sheet. And they just went down the cheat sheet and the cheat sheet told them who to vote for on the ballot.

So that's how most people, I think, vote.

That's crazy to me. So he's going to win, it looks like.
Yeah. And I am.
I am glad he's going to win because I want to see how screwed up these policies get. And then 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, you know, starved. China, you know, what is it? 40 million people starved when they tried to freeze these prices.

So we'll see what happens. New York City, you know, we're both familiar with it from our different periods of our lives.
Like it's a hard city to run.

I just went back there to film at a 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. Yeah, it's really sad in that people, of course,

look,

I wanted New York City to be successful. I wanted 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. It 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.

Wow, he cut you off.

I think so, actually. Like, I even 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. Do you think it's because of your article about how?

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.
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.

Yeah. No,

everybody is so charismatic.

And I'm, I'm like, oh my, like, particularly like actors, like when they come on the show, and maybe you experienced this, like, I'll be thinking in the middle of the episode, oh my God, this is my new best friend.

Like, he's on my favorite TV shows, and now he's my best friend. And then I'll never hear from them again.
I'll like, I'll say, oh, I'm in LA. Now you said reach up and nothing.
Same.

It is a little disheartening because I feel like on podcasts, I'm pretty much myself. Maybe I alter it 5, 10%, but I'm genuinely myself.

But some people just have a switch and they're completely different and I got to admire that they're so good at it 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 it's an interesting thing because when you win an episode like look you 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 3 a.m.
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 3 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 podcasts. Helped you build that confidence.
Yeah, because I was really not confident at all doing that.

Yeah, I don't think you could learn confidence in a book. No.
Oh, no. I mean, I don't think you could, it's very hard to learn anything in a book.
Really? Yeah, like what have you learned in a book?

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? 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 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. Fair point.
So, or

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. 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.
Yeah.

So, or, or chess, like we were talking about chess earlier.

I, 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.

Yeah, I've accepted that. I don't think I'll ever get past 1600.

You never know. Like, it's just a matter of like.

I would have to spend money and hire a coach yeah 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 five percent but unless i like devoted a lot of my life towards it i don't think i like i do it on the side yeah like you could you would only do it more than that if you if you loved it like if like every waking moment and you know when i was a kid there was a period where every waking moment I had to play chess.

Like I would, I would not go to school for like days or even weeks at a time just to, just to play play all day. You're on the streets in New York City, just hustling.
Yeah, yeah.

And 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, you know, on some spectrum. And I'm going to 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 because that's what was going on.

And he would just play chess all day. So I'll just go over his house and we 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. That's nuts.
Yeah.

That was your mentor, right? 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.
Adopted.

Yeah. And, you know, we just had a fun time just analyzing the game and playing games all day.
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. 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

I'm going to analyze the game there. Like I don't care about your analysis.
I just care about the computer's analysis. 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 in a chess setting? In a tournament, probably not, but definitely like in Blitz and casual chess. Yeah.

I agree because I think that's an edge if you're good at talking, like it could help you win games. Oh, yeah.

Like in Washington Square Park and 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 got to be at least 50, 60% of the game. Wow.
Not necessarily like whether I'm going to 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 got to be mental.

Yeah, because you're the same skill level. Yeah.
So what separates you?

You know, 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.

That will affect whether you see certain moves later on in the game. Like

last tournament I played in,

and 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 them because you just shut down, 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.

Wow, and I try really hard, like, I know how important mindset is, but for whatever reason, this particular tournament, I didn't kick in at all. 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. Probably, yeah, yeah.

And, 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 as 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 going to 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 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. It's interesting.
I'm very hard on myself too. And sometimes I wonder if that's good or bad.

I don't think it's that good. I think 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 and the other side but uh but you you you have to just say okay that was a learning experience and and I'm gonna 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 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 post-mortems or investments.

You can never, the worst words are to say, oh, I just got unlucky or the other person just got lucky. Yeah.
Like then you ruin it. Wow.
So that actually worked with comedy, though.

You felt like you got better doing it. Oh, yeah.
Cause 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 was ignoring me.

And so I didn't sense that

during the performance. Or, oh, I talked too fast during this one part, or I didn't really commit to the joke.
Like, you could see I'm nervous.

Like, 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. Right.

So, so, oh, and if you, if I could see that in my videos of myself, then I know the audience could see it. So you have to really analyze.

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 oh yeah because 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 like like it's like business too There's no one skill like, oh, I have business skill.

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, your company and your efforts. That's a skill.
So there's all these like sub-skills to business. You know, writing's the same way.

There's, there's skills with storytelling, skills with

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, are really just, you you know collections of micro skills Yeah, and do you recommend when people are starting out to learn one skill at a time just to hone in on one?

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 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? Yeah.
So you won't be able to isolate the skill.

That's definitely a hot take because I know comedians hate when you take their jokes. 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 also.

Did you know public speaking is the number one fear in the world? Yeah, that'd be right.

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.

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.
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, and public speaking, you're exposing yourself completely and if 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. Is that why you wanted to get in comedy to get over that fear? I just loved comedy, but yeah, I was so afraid.

So actually, I was doing a podcast with Stephen Dubner, one of the authors of Freakonomics, and we challenged each other to rent out a hall in New York City and do stand-up 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 like 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.
Yeah. You got top 1%.

Yeah, I got top 1%. It's pretty good in comedy.
Yeah. Because in comedy, apparently, you got to devote 10 years, they say.
Oh, yeah.

I would say, look at all the comedians that are even like the next generation after like let's say the louis zays and chris rox like let's say andrew schultz chris destafano theobond i would say they're they're the next generation after like louis chris rock all of them a minimum you only heard about them after they were doing it for about 15 years yeah and that's amplified even faster because of social media too yeah if they didn't have that it would have taken probably 20 30 years and podcasts also help them like take someone like tim dylan 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 yeah i think comedy podcasts are number two out of every category yeah and i i would bet they're i mean what's first is like true crime true crime yeah so i would bet you that true crime and 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 um but like Theo Vaughn, Chris Dostoffano, Tim Dylan, they're great podcasters, and it's because of their comedy skills.

What show is your category in?

I don't even know.

What category is your show in? I said that's 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 I kept trying to tell people I'm really more self-hurt.

But, you know, it became self-help. So it goes back and forth between those categories.
I went 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 know. Yeah, same with me.
It's more general. Yeah, it's more like, who do I think is interesting? Yeah.
That's exactly what I do.

I promise on my show. Do you ever worry that that makes you too general? 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.

Yeah, and 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 am 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.
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. Right.
It doesn't even make sense to me. 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 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 tick tock right now oh i didn't know that 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 yeah and like what was it would you know what uh what was it that it was israel stuff you know yes but the thing is i have on both sides but if one side only sees one one certain clip, they'll just mass report it, get my account banned.

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

one war situation. And probably like people 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, it really, someone else could say, no, it started 10 years earlier.

And so, and then no one's gonna, no one's ever gonna to agree, no one's going to change their mind. So you're not, so, so what's the point of,

you know, I could see if somebody says, you know, death to all of 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 want to say it's entertainment because that makes a mockery of it, but I don't know. You know, it's just hard to really know.

Well, political commentary has turned into entertainment at this point. There's no doubt.

Like, if you watch Pierce Morgan and you watch some of these political commentary shows, it's just a screaming match.

It's just like stirring up drama yeah and like and again who are they convincing like what good are they doing in the world yeah so i think politics is i think many people focus on it and it's not worth the time they're putting in like i sort of miss 2012 in the sense that barack obama and mitt romney they were the same person actually pretty much like they're like like you know the issue was obamacare but mitt romney was the one who who was the test when he was governor of massachusetts he created romney Care.

It was the same thing. So they were not really different.
Nobody was going to 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. I agree.

I think when Trump ran the first time, he just brought a whole new set of eyeballs into the politics, right? And

look. He was funny.
It was just a little different. That's what won him the election.
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.
Yeah. Are you still in Jersey?

I know you were growing up in North Brunswick. Yeah, no, I lived my whole adult life in New York City.
Most recently, though, I've been living a little outside of Atlanta, Georgia. Okay.
Just wanted

to be a break. Yeah.
Some land.

Yeah. Yeah, some land.
I didn't want to smell things all day long. There's like studies on life inspectancy.
Have you seen these? No.

For people that live in major cities, especially New York, it's like a few years lower than the average.

that's really interesting the pollution and uh 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 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

yeah 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 uh

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.
Yeah, it's like 10K a month, right?

Yeah, like to get a, to get an acceptable apartment is like almost minimum that. Otherwise, you're going to 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.

I think that's most cities these days, right? Because a state

too, yeah. Um, yeah, 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 plan is to like to have a getaway and just go back and forth when I oh, the funny thing is, Las Vegas is like a getaway. Like, if you go outside,

you have the beautiful desert like just minutes from here.

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.

Yeah, oh, yeah, even like staying in hotels and stuff is like one-third the price of New York City. Yeah, I do a staycation every three months.
There's so much

hotels out here, man. Which one are you up? I'm, I'm at the, the, I think it's pronounced Vrada, Vadera, oh, Vedara, Vedara, yeah, next to Aria.

Yeah, I didn't want to stay at a casino, so I got a gambling addiction. Well, I used to, I used to play a lot of poker, and I just don't want to be any,

I'm just not interested at all in being tempted by anything. Did you get wrecked? Uh, 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 8 p.m.

to 4 a.m., every single night, I would play like 365 straight days, like a year.

And 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.

We still do, right? 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 I got wrecked.
Got it. So poker is a very interesting game because you could be really good, but still lose.

Yeah. Like a lot of money.
Yeah. You got to pick the right games.
You know what I mean? You can't let your ego get in the way.

yeah like i you know there's a great player gus hanson 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 and that's common with a lot of the poker guys i wonder that 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 you get a taste of it because i grew up pretty like broke honestly like zero to 20.

yeah um just relying on my parents and then i didn't i wasn't depressed i mean i was but that was college that was different But then when I lost all my money,

that's the worst. That was rough.

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 going to 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. Because you got the skill set and the mindset.
Yeah, I and I have to remind myself of it because it still feels depressing. Yeah.

And I still have to tell myself I've got to do things. I've got to write, 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. Yeah.

Like there's three skills to money. There's, there's me, 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. What do you think is the hardest out of the three?

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. I agree.

I think making it for me is the easiest, but for most people, it's the hardest. 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 to.

Like, for instance, 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. That makes sense.

And then keeping it, that's just a matter of controlling your vices. 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. Right.

So you can make some risk you have to but but i can't take too much risk yeah that was my issue too i invested all over the place in stuff i knew nothing about that's how i lost it right people think it's like oh did you spend money on like drugs and hookers no it was really just trying to

you i had 10 million trying to make a hundred million is the mistake i made i've never been able to make that jump yeah no i i i'm you know Without saying too much, I have not been able to make that jump either.

I also think the jumps don't hit the same, if that makes sense. Like zero to 100K was crazy.
I felt like a baller like in college making that money. 100K to a million felt really good.

A million to 10 was all right. But like now I feel like money has kind of lost its,

I don't know how to word it. Yeah, I mean, now

it's right, because that's why you could, that's why now, first off, when you have like a good number, it's easier to make it and lose millions and it's not going to affect you as personally.

Although I try to have it affect me so that I still feel that hunger. Right.
Like, and I always remind myself of, you know, other people who I'm responsible for and other obligations I have.

And usually you're not in a world by yourself. Like, 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 always make the stakes very high. 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? When you first made a lot of money, how were your relationships?

Really bad. Really? Terrible.
Yeah, because I was all in on making money. I was obsessed like you were.
Yeah. And then did you lose a lot of relationships? Yeah, tons.
Now I'm like rebuilding them.

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 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 yeah yeah i sacrificed a lot to get early success for relationships my physical health was my mental health was awful uh i wouldn't recommend it honestly for most people i barely made it through i was in the er like it was yeah it wasn't fun Yeah, it's not fun.

I had panic attacks all the time. 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.
Valid. There's pleasure in improvement.

And there's, I, 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.
Same.

Because I think if you're not improving, you're declining. So for me, I have to constantly be improving.
Yeah, or else it kind of loses flair. But

I'm told that's a big mistake in life. 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? Yeah.

So diminishing returns, I think that's what they call it. Yeah.
And that's painful. Yeah, it is.
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 Carlson, the rest of them are all, I would say, mildly depressed. Yeah, because they don't make money.
Yeah.

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.
It is crazy, that comparison game that we all play.

And social media plays a role in that too, I think. Yeah, like, look, social media is so hierarchical that, you know, and look, every day I'll do it.
Like if two people follow me,

okay, I'll follow the person back with more followers. Like it's just very hierarchical.

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 was so non-important. Yeah.

But then later on, it's like not important to me now. So I'm glad it's lost meaning, to be honest.
Followers only matter now for getting DMs, but they don't matter to get views.

Yeah, because the algorithm now is better.

Yeah, it's way better. I love it.
I get more views from non-followers on my show. 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? The only for you, yeah.

I don't want to see what I'm people I'm following proposed. What the hell? Yeah, exactly.
Like, I already know what they do, yeah, and they're not superheroes.

I'd rather look at the super, the Gen Z superheroes on TikTok. 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.

Like, I can't believe every day when I look at social media, 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.
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 um.

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 yeah i think it's the access to information because it's so easy to learn these days and maybe they're better at learning too like just learning quickly because they got they're so used to it well i know i am now with ai i'm learning so fast these days 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 i 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 yeah no judgment no judgment yeah that's a good point man well james this has been super fun i can't wait to uh do another episode with you one of these days.

Where can people find your show and everything?

James Alter's show,

you know, or

listen to me here on Sean's excellent show. So, anywhere you want to find me, you can find me.
We'll have to play chess, but you can't start with a queen to make it fair. How about I'll do Blindfold?

Oh, that'd be fun. Let's do it.
I've been practicing that lately. That's my training now.
One game a day, Blindfold. Let's do it.
All right, man. Check them out.
See you next time. Peace.
Thanks.

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