Encarta | Entrepreneur Who Lost Millions Breaks Down How To Come Back Financially

00:00

So the background here, by the way, Sean, is I was on James's show,

00:00

So the background here, by the way, Sean, is I was on James's show,

00:05

three weeks ago. It actually aired today. Yes. I've been getting people reaching out reaching out to me. James,

00:05

three weeks ago. It actually aired today.

00:07

I've been getting people reaching out to me. James,

00:11

James is an oddball. I like him. He's been around and done all types of interesting stuff. He's had books. He's got paid newsletters. He's

00:11

James is an oddball. I like him. He's been around and done all types of interesting stuff. He's had books. He's got paid newsletters. He's

00:18

I don't know what how you describe yourself, but you're just kinda all over the place and you've done all types of stuff and you have a really interesting life. And, we thought we'd get a we thought we'd get them on here. And we could talk about anything, but,

00:18

00:31

do you know about James, Sean? I know about you. Yeah. I know about him. I've read a bunch of your stuff. I was like, this guy's the shit. And then I read I read something that was like, I think you were talking about Bitcoin or crypto at the time. And I was like, wait a minute. Is this just a guy who just just sells the latest thing? Like, oh, here's the new thing. Cool. I'll shield that. And I was like, oh, okay. I don't know how I feel about this. And then I've read some of your stories where where you talk about how you made money and lost it all over and over and over again. And I was like, this guy is very interesting. You reminded me of, like, if Tim Ferris, you know, smoked a bunch of weed and was on the internet. I don't know. Like, is this, like, some some variation of really interesting guy who, you know, who's built his brand on the internet,

00:31

01:08

you know, you always had, like, something unexpected. Like, it wasn't the formulaic thing, like, even the fact that you own a comedy club is, like, you always have sort of unexpected things. That's what I have sort of come to like about you. But

01:08

01:19

You know, that's my admittedly

01:19

You know, that's my admittedly

01:21

very loose,

01:21

very loose,

01:22

knowledge about about you. Do you wanna give some background?

01:22

knowledge about about you. Do you wanna give some background?

01:25

Yeah. I mean,

01:25

Yeah. I mean,

01:27

It's kinda like what you were both sort of referring to. I've I've had for better or for worse,

01:27

It's kinda like what you were both sort of referring to. I've I've had for better or for worse,

01:33

a lot of different interests, which I turned into a lot of different careers, And I say for better or for worse because a lot of times I would have an interest. I'd build a business. I'd sell it. I'd make money. And then for some reason, I would just I don't know. I would totally shit the bed and lose everything. And I'm not talking about, like, oh,

01:33

01:54

I sold something for a billion, and I ended up with ten million. This is horrible. No. I would sell something for millions and then end up with

01:54

I sold something for a billion, and I ended up with ten million. This is horrible. No. I would sell something for millions and then end up with

02:02

zero or less than zero in my bank account,

02:02

zero or less than zero in my bank account,

02:05

really just zero, actually. I wish it sometimes it's better to be less than zero than to be zero. Because if you, like, are less than zero, then that means there's a deal you could work out with somebody. Like, oh, I owe you ten million. Let's work it out. And you maybe give me some so I could build an I don't know what it is. But, like, I I think it was a, a young man in the nineties,

02:05

02:26

name Donald Trump, who said, if you owe if you owe two million to the bank, the the the bank owns you. But if you owe two billion to the bank, you own the bank.

02:26

name Donald Trump, who said, if you owe if you owe two million to the bank, the the the bank owns you. But if you owe two billion to the bank, you own the bank.

02:36

And

02:36

And but but, anyway, I would often end up,

02:37

but but, anyway, I would often end up,

02:39

at at zero dollars and be depressed

02:40

at at zero dollars and be depressed

02:42

to the point of, like, suicidal. Like, I had kids to feed. I had myself to feed. And it's really true. When you go from having money and selling a business to broke, you find out who your real friends are. And for me, almost every time, it turned out I had zero friends.

02:42

02:58

And so I had nowhere to go and and no idea and and depressed. And I didn't know how, in some cases,

02:58

And so I had nowhere to go and and no idea and and depressed. And I didn't know how, in some cases,

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put food on the table for my kids after having millions. And so I had to learn very quickly over and over again. What are my interests? What can I pursue? What's an idea?

03:04

put food on the table for my kids after having millions. And so I had to learn very quickly over and over again. What are my interests? What can I pursue? What's an idea?

03:14

How to be creative and maybe a horrible environment and then figure out how to monetize it. So I was a software guy. I worked in the entertainment industry. I worked for HBO.

03:14

How to be creative and maybe a horrible environment

03:17

and then figure out how to monetize it. So I was a software guy. I worked in the entertainment industry. I worked for HBO.

03:24

I started I combined those two things, and I started a a company in the nineties, making websites for entertainment companies.

03:24

I started I combined those two things, and I started a a company in the nineties, making websites for entertainment companies.

03:31

And then I became a venture capitalist, then I started a hedge fund. I wrote some software to help me invest, and that and then I started writing books about that. So I became a writer. Then I became a podcaster.

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03:42

And then, like you were saying, I started writing about

03:42

And then, like you were saying, I started writing about

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much more personal stuff And I think everybody

03:46

much more personal stuff And I think everybody

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who knew me

03:50

who knew me

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couldn't believe it. Like, it was almost like they had never seen anything like this before. Like, why they people call me up. Like, James, are you, do you have cancer or are you about to kill yourself? Are you about to die? Like, why are you confessing to all these things? These these are horrible. No one's ever gonna

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couldn't believe it. Like, it was almost like they had never seen anything like this before. Like, why? They people call me up. Like, James, are you, do you have cancer? Or are you about to kill yourself? Are you about to die? Like, why are you confessing to all these things? These these are horrible. No one's ever gonna

04:06

and do a deal with you again, or or this is too embarrassing.

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and do a deal with you again, or or this is too embarrassing.

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And

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And

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I I you know, and then I think since then, people have I don't wanna say people copied it. People had their own versions of writing about failure and and so on. But and then those became I started writing books based on those articles, And it turned out I had not only was I building up even more as a writer, and my audience was bigger than ever previously I'd written about Finance. Now I was writing about all this personal stuff. My audience became a hundred times bigger, and then I started getting more investment opportunities

04:12

04:39

I started getting a podcast which became successful.

04:39

I started getting a podcast which became successful.

04:43

I just started getting many more opportunities because of

04:43

I just started getting many more opportunities because of

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because because essentially I I paid with my vulnerability

04:48

because because, essentially, I I paid with my vulnerability

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for freedom,

04:51

for freedom, and that created a whole

04:52

and that created a whole

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kind of career for me. And it wasn't intentional.

04:54

kind of career for me. And it wasn't intentional.

04:58

I just was sick of writing about

04:58

I just was sick of writing about

05:00

all the BS stuff. I kept seeing everyone else write about. And if you wanna If you wanna be unique, you kinda have to say what's unique to you, and what was unique to me was all the times I was scared to death and and depressed and and had to fight my way out of it. So many things to to answer the question. I've I've I have back background a lot of things. And also, I always like trying new things and experimenting, and I'm I was everything I'm passionately interested in, I like I like figuring out how to make money from it and and getting good at it. And so if somebody's listening and they're like, okay. Cool. You made millions. How did you go to zero? So what what what was happening? What how are you making money? And how are you taking it to zero? Were you just making wild bets or what happened? Yeah. Yeah. What were your, like, hits? I imagine you've had, like, three hits. Yeah. I would say it's more, like, five or six hits, again, for better or for worse. I needed all five or six. But,

05:00

all the BS stuff. I kept seeing everyone else write about. And if you wanna if you wanna be unique, you kinda have to say what's unique to you and what was unique to me was all the times I was scared to death and and depressed and and had to fight my way out of it. So on many things to to answer the question, I've I've I have back background on a lot of things. And also I

05:19

always like trying new things and experimenting, and I'm I was everything I'm passionately interested in, I like I like figuring out how to make money from it and and getting good at it. And so if somebody's listening and they're like, okay. Cool. You made millions. How did you go to zero? So what what what was happening? What how are you making money? And how are you taking it to zero? Were you just making wild bets or what happened? Yeah. Yeah. What were your, like, hits? I imagine you've had, like, three hits. Yeah. I would say it's more, like, five or six hits, again, for better or for worse. I needed all five or six. But,

05:50

the first one, again, I was working at HBO,

05:50

the first one, again, I was working at HBO,

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and I made their website.

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and I made their website.

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And

05:56

And

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at the at the time,

05:57

at the at the time,

05:58

other entertainment companies and other companies. They didn't even know what this internet web thing was. This was in nineteen ninety five. And

05:58

other entertainment companies and other companies. They didn't even know what this Internet web thing was. This was in nineteen ninety five. And

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Companies like American Express,

06:07

Companies like American Express,

06:09

American here's what happened. American Express would call Arthur Anderson, which was their accounting firm, And, you know, Arthur Anderson famously went out of business,

06:09

American here's what happened. American Express would call Arthur Anderson, which was their accounting firm,

06:14

And, you know, Arthur Anderson famously went out of business, in in a scandal six years later, but American Express called Arthur Anderson said, can you make us a website? Arthur Anderson said, sure. Well, they're gonna charge you millions of dollars. Arthur Anderson would then call another software consulting company, and they would say, yeah, we'll charge you a million dollars. The software company would call me because nobody knew how to make a website in nineteen ninety four and nineteen ninety five. So I would say, sure. I'll do it. And then suddenly,

06:18

in in a scandal six years later, but American Express called Arthur Anderson said, can you make us a website? Arthur Anderson said, sure. Well, they're gonna charge you millions of dollars. Arthur Anderson would then call another software consulting company, and they would say, yeah, we'll charge you a million dollars. The software company would call me because nobody knew how to make a website in nineteen ninety four and nineteen ninety five. So I would say, sure. I'll do it. And then suddenly,

06:41

They pay me and my brother-in-law,

06:41

They pay me and my brother-in-law,

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two hundred fifty thousand dollars to make american express dot com. So that was one of our first websites.

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two hundred fifty thousand dollars to make american express dot com. So that was one of our first websites.

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And I my salary at HBO at the time was forty thousand a year. So my brother-in-law and I, we made HBO dot com, then we made

06:50

And I my salary at HBO at the time was forty thousand a year. So my brother-in-law and I, we made HBO dot com, then we made

06:58

websites for everything from

06:58

websites for everything from

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Warner Brothers, Sony, Disney, BMG,

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Warner Brothers, Sony, Disney, BMG,

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all the record labels, like, We did every gangster rap record label. Bad Boy, loud records,

07:04

all the record labels, like, We did every gangster rap record label. Bad Boy, loud records,

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Jive, death row, interscope.

07:10

Jive, death row, interscope.

07:12

We did the movies for the matrix,

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We did the movies for the matrix,

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and many other movies. But anyway, that was And were these built up? Websites at that time? Like, if you looked at that website today, what would it look like? Is it like a Craigslist?

07:14

and many other movies. But anyway, that was And were these built up? Websites at that time? Like, if you looked at that website today, what would it look like? Is it like a Craigslist?

07:23

You know what? That's a great question. So, no, it doesn't look like Craigslist. I wish it did, but,

07:23

You know what? That's a great question. So, no, it doesn't look like Craigslist. I wish it did, but,

07:28

design web design back in those days. So I was a software guy. My brother-in-law was a design guy.

07:28

design web design back in those days. So I was a software guy. My brother-in-law was a design guy.

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Web design back in those days was very heavy. So there would be, like, big, heavy images and animations

07:33

Web design back in those days was very heavy. So there would be, like, big, heavy images and animations

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using Flash or Yep. You know, some

07:40

using Flash or Yep. You know, some

07:43

mac I forget the company macro or something. And,

07:43

mac I forget the company macro or something. And,

07:47

they were they were very heavy designs, not that usable.

07:47

they were they were very heavy designs, not that usable.

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And but, yeah. I mean, they were okay. They're they were admired back then. So the website for the matrix was a great website,

07:50

And but, yeah. I mean, they were okay. They're they were admired back then. So the website for the matrix was a great website,

07:58

which, you know, on on archive dot org, you could find, or HBO's website was a great website, but it wasn't as functional as all websites are now. It wasn't very easy to navigate. And what did you walk away with at the end of that? About

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08:11

fifteen million. And then Holy fuck. Yeah. So cash. Not not like so a lot of people then, you know, went public or sold and they got paper. And then they died in the dot com bust. Because the paper went to zero. The stocks went to zero. So I had enough sense at like the peak in nineteen ninety nine. I cashed out and I had the cash in my checking account. Like, I didn't even wanna What do you mean cash out? Were you getting, like, stock in these comp? I mean, I was saying So so no. No. I sold the company to a company that was rolling up website for web agencies. And so we in a sense, that was how we went public. Like some company that made, I don't know, vacuum cleaners or whatever, decided to get into the internet business in nineteen ninety eight and acquired us. And so suddenly they were an internet company and the stock went from three to forty eight. And I cashed out with literally at the peak with about a little over fifteen million, almost sixteen million cash.

08:11

09:04

And

09:04

And

09:05

and here I was. I was smart every step of the way. Like, I knew that the web design development business

09:05

and here I was. I was smart every step of the way. Like, I knew that the web

09:10

design

09:11

development business industry was going away because they were teaching

09:12

industry was going away because they were teaching

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web you know, how to make a website in junior high school classes. I knew this was going away. I was smart. I sold the business. I cashed out as fast as I could. And then

09:16

web you know, how to make a website in junior high school classes. I knew this was going away. I was smart. I sold the business. I cashed out as fast as I could. And then

09:25

I became everybody, you suddenly when you when you make money at one thing, suddenly you think you're a genius at everything or at least this happened to me and everybody would come to me and say, hey, how can What what should we invest in? Or you know this internet thing. You you you have like curly hair and glasses. You must know how the all the this internet stuff. You're you look like a technology guy. What should we invest in? So I start thinking, oh, I must be really smart at this. And literally, I poured all this cash back into

09:25

09:56

internet investments

09:56

internet investments

09:58

after I cashed out of the internet.

09:58

after I cashed out of the internet.

10:00

And it it really went

10:00

And it it really went

10:03

And then I also I bought, like, a huge apartment in New York City. And the one thing I was doing that everybody thought I lost all my money on, but it wasn't I was I was gambling every single day. Like, I was playing poker for three hundred sixty five straight days. I played poker at least eight to ten hours a day. I was gonna ask you if you're a degenerate gambler because you kinda have that.

10:03

10:25

I mean, you you sound liked it before you even told me you're a gambler. But but but that's just it. Poker was the one thing I probably should have stuck with. Like, I was doing well at poker, and it was right before po the poker boom took off when I decided, you know what? I'm just gonna focus on starting new companies and internet investing, and I stopped playing poker like, in, you know, right at the end of nineteen ninety nine, I started a venture capital firm, and I just started investing

10:25

10:50

money. And Was was your firm all your money? So your firm No. No. We raised we raised two hundred million dollars. Like Holy fuck. That was the other thing too. I didn't have any experience.

10:50

money. And Was was your firm all your money? So your firm No. No. We raised we raised two hundred million dollars. Like Holy fuck. That was the other thing too. I didn't have any experience.

11:00

Doing any of this stuff. I didn't know anything.

11:00

Doing any of this stuff. I didn't know anything.

11:03

I I'm I'm trying to remember all investors.

11:03

I I'm I'm trying to remember all investors.

11:06

C s first Boston,

11:06

C s first Boston,

11:08

Deutsche Bank, Like, all these major banks gave us money. And then another company in Vescorp,

11:08

Deutsche Bank, Like, all these major banks gave us money. And then another company in Vescorp,

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which is a major private equity firm,

11:14

which is a major private equity firm,

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gave us a hundred million.

11:16

gave us a hundred million.

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And

11:18

And

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and then I started investing my own personal money side by side with the fund and then other investments, and I started buying stocks.

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and then I started investing my own personal money side by side with the fund and then other investments, and I started buying stocks.

11:26

All the way down. So how long till it was to zero? From fifteen to zero, how long was that?

11:26

All the way down. So how long till it was to zero? From fifteen to zero, how long was that?

11:32

I was losing about a million dollars a week in the summer of two thousand.

11:32

I was losing about a million dollars a week in the summer of two thousand.

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And

11:36

And

11:37

and I just didn't know what I was doing. And it wasn't even that I didn't know how to invest. I didn't know

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and I just didn't know what I was doing. And it wasn't even that I didn't know how to invest. I didn't know

11:42

There's so many other skills to investing than knowing what companies are good and what companies are bad. Like, I didn't understand risk. I didn't understand money management. I didn't understand

11:42

There's so many other skills to investing than knowing what companies are good and what companies are bad. Like, I didn't understand risk. I didn't understand money management. I didn't understand

11:52

you know, had a I really didn't understand anything then about investing. Like, I was an idiot. And I went to zero by

11:52

you know, had a I really didn't understand anything then about investing. Like, I was an idiot. And I went to zero by

12:00

right around mid two thousand one, I put up my I was desperately putting up my apartment for sale because maybe I would have some money left I stopped paying my mortgage, and maybe I would have some money left after putting this apartment up for sale. I lived two blocks, three blocks from

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12:17

a a little building called the World Trade Center. And we were getting an offer

12:17

a little building called the World Trade Center,

12:20

and we were getting an offer

12:22

on September eleventh And, of course,

12:22

on September eleventh And, of course,

12:25

many worse things happened that day than me not getting an offer from my house, but,

12:25

many worse things happened that day than me not getting an offer from my house, but,

12:30

nine eleven happened, and we couldn't sell then because we were part of the crime scene.

12:30

nine eleven happened, and we couldn't sell then because we were part of the crime scene.

12:34

And,

12:34

And,

12:36

you know, it just I went totally Were you home? Broke. Were you home now? I was at the World Trade Center.

12:36

you know, it just I went totally Were you home? Broke. Were you home now? I was at the World Trade Center.

12:42

So Oh my god. Which I don't really

12:42

So Oh my god. Which I don't really

12:45

I don't really talk about because a, it sounds unbelievable, but b, it also many worse things happen to people, to many more people than me that day, obviously. But My business partner and I were there was a Dean and Deluca in on the first floor of the World Trade Center. We ate breakfast there every day, and then we would day trade the markets.

12:45

13:02

And,

13:02

And,

13:04

at that point,

13:04

at that point,

13:05

I was starting to come back a little bit from day trading, and I had written some software and and so on. And

13:05

I was starting to come back a little bit from day trading, and I had written some software and and so on. And

13:12

Then we're walking

13:12

Then we're walking

13:14

to my home where I had my office, and we my partner turns to me and says, is the president coming into town today? Cause this I look up, and there's this plane

13:14

to my home where I had my office, and we my partner turns to me and says, is the president coming into town today? Cause this I look up, and there's this plane that's just, like, right overhead. And then, boom, we watched it go right into the, like, physically we watched it, not TV, but, like, physically, we saw it go right into the building, and everybody on the street instinctively

13:23

that's just, like, right overhead. And then, boom, we watched it go right into that, like, physically we watched it, not TV, but, like, physically, we saw it go right into the building, and everybody on the street instinctively

13:34

ducked.

13:34

ducked.

13:35

And

13:35

And

13:37

And your your brain does weird things. So my I started thinking to myself, like, my my business partner's name is Dan. He said, we're we're we're being attacked. And I'm like, no. No. No. That was that was just an accident. Like, and no one's no one's it's too early. No one's in the building.

13:37

13:52

Like, my brain was telling me this, even though it was a quarter to nine AM. And,

13:52

Like, my brain was telling me this, even though it was a quarter to nine AM. And,

13:56

you know, how do you remote control? Whatever it was, a seven forty seven into the World Trade Center, but that's what my brain was telling me. So we run to the buyer station,

13:56

you know, how do you remote control? Whatever it was, a seven forty seven into the World Trade Center, but that's what my brain was telling me. So we run to the buyer station,

14:06

and we say we wanna help.

14:06

and we say we wanna help.

14:09

And these guys throw two fireman suits at us and say, get this on. We're gonna go straight over there. And

14:09

And these guys throw two fireman suits at us and say, get this on. We're gonna go straight over there. And

14:16

we start putting it on, but then they say, wait a second. Are you guys Fireman. And we're like, no. We just wanted to give blood or whatever we could do. And they're like, no. No. No. Only fireman.

14:16

we start putting it on, but then they say, wait a second. Are you guys firemen. And we're like, no. We just wanted to give blood or whatever we could do. And they're like, no. No. No. Only firemen.

14:26

And that fire station was the Duane Street fire station. A hundred percent of those people died. It went to the World Trade Center that morning. And

14:26

And that fire station was the Duane Street fire station. A hundred percent of those people died. It went to the World Trade Center that morning. And

14:34

And then from, you know, it's there's a a bad day, but that kind of clinched me losing everything also because I had been invested in the stock market that morning and boom, everything kinda went to went to zero after that. And then I was just

14:34

14:51

desperate for, like, a year and a half. Couldn't sell the place.

14:51

desperate for, like, a year and a half. Couldn't sell the place.

14:55

Couldn't there were no jobs. I was an idiot. Nobody would I had no friends anymore.

14:55

Couldn't there were no jobs. I was an idiot. Nobody would I had no friends anymore.

15:01

And,

15:01

And,

15:02

you know, I had to

15:02

you know, I had to

15:03

I had to teach myself how to invest. So I wrote

15:03

I had to teach myself how to invest. So I wrote

15:06

some software

15:06

some software

15:08

where I, took every piece of data about every single stock stock since World War two and looked for patterns

15:08

where I took every piece of data about every single stock stock since World War two and looked for patterns

15:16

you know, when would I would have my software find statistically significant patterns

15:16

you know, when would I would have my software find statistically significant patterns

15:21

where trades were good. So I would try to model

15:21

where trades were good. So I would try to model

15:25

let's say fear and greed in the markets, and and and it worked pretty well. Doesn't it wouldn't I don't think that strategy would work now, but it worked then because there weren't there wasn't that many quantitative

15:25

15:34

investors in the markets then. This was kind of the beginnings of that. And so I was very successful with it, and that kind of kept me alive. And that's how I bit by bit I started

15:34

investors in the markets then. This was kind of the beginnings of that. And so I was very successful with it, and that kind of kept me alive. And that's how I bit by bit I started

15:46

learning about investing. This gave me time to actually learn the skill and and talk to people who were experts and professionals and and really learned that I started writing about investing.

15:46

learning about investing. This gave me time to actually learn the skill and and talk to people who were experts and professionals and and really learned that I started writing about investing.

15:56

And I started going on CNBC, and I started a hedge funds, and I start I wrote my first book about investing. And so gradually, I built these two careers, one in the hedge fund business and the other in writing about

15:56

16:09

investing and going on CNBC.

16:09

investing and going on CNBC.

16:12

And then I built,

16:12

And then I built,

16:13

so I was doing deals also then and making money. And then I built a a website

16:13

so I was doing deals also then and making money. And then I built a a website

16:18

that combined my interest in web development with investing me, like, a social I called it the MySpace of Finance because MySpace was big then. And

16:18

that combined my interest in web development with investing me, like, a social I called it the MySpace of Finance because MySpace was big then. And

16:27

sold that site, and that was, like, my next big hit, sold that for ten million.

16:27

sold that site, and that was, like, my next big hit, sold that for ten million.

16:32

And

16:32

And

16:34

you know, and then a year later, I was broke again.

16:34

You know, and then a year later, I was broke again.

16:37

And that's the things like that just kept happening.

16:37

And that's the things like that just kept happening.

16:40

Alright. This episode is brought to you by Super side. Alright. So here's the deal. I'm incredibly impatient, like horribly horribly impatient. And if I get an idea at midnight, by eight AM the next day, I want it done. You know, but that's really hard because if something needs to be designed, where am I gonna find a designer at midnight to try to make this thing bring it to life? So, you know, I don't think I'm alone, other startups, even huge companies need design help fast, and they just don't have the internal resources or expertise to get it done. So how do you get reliable design done without dealing with expensive agencies and lots of freelancers,

16:40

17:11

you use superside. That's our sponsor for this week. Just go to superside dot com slash m f m and tell them what you want. They have a team of designers that can get it done fast. You know, they are twenty times faster than hiring a designer and fifty percent more affordable than a traditional agency. So If you need high quality design done fast, try super side. Lots of fast growing teams that are stretched, are using them already. Check them out super side dot com slash m f m. I've used them before. I love them. Check it out.

17:11

17:38

There's a lot going on here, but

17:38

There's a lot going on here, but

17:41

it's used to a two company so far? Well, you've also sold your newsletter business too. Right? Yeah. So so that was a third company. And I've also sold companies that I was,

17:41

it's used to a two company so far? Well, you've also sold your newsletter business too. Right? Yeah. So so that was a third company. And I've also sold companies that I was,

17:50

either

17:50

either I there's many companies I've been an investor of that have been sold by this point. And then some companies that I'm, like, a a cofounder of that I've that I've sold I was, like, involved. I've been involved with everything from, like, a mental rehab facility that sold for forty one million. And then that was in two thousand four. I did go broke after that.

17:51

I there's many companies I've been an investor of that have been sold by this point. And then some companies that I'm, like, a a cofounder of that I've that I've sold I was, like, involved. I've been involved with everything from, like, a mental rehab facility that sold for forty one million. And then that was in two thousand four. I did go broke after that.

18:09

And then was Stockpicker, the stock site. And then I was an early investor in Buddy Media,

18:09

And then was Stockpicker, the stock site. And then I was an early investor in Buddy Media. Which

18:15

which Peter Teel invested in. Mike Lazarusra was the CEO, Mark Pinkas, who started Zingo, was an investor in it. And we all were the seed investors

18:16

Peter Teel invested in. Mike Lazarusra was the CEO, Mark Pinkas, who started Zingo, was an investor in it. And we all were the seed investors

18:24

at a four million dollar valuation that's sold to Salesforce

18:24

at a four million dollar valuation that's sold to Salesforce

18:27

for about seven or eight hundred million.

18:27

for about seven or eight hundred million.

18:30

I had a I had a company today that I was a, investor and that just it just kinda did a re or they're they just announced the reverse merger. They're going public. So, hopefully, that will do well. But I've been I I've been an investor in a lot of companies that have done well. Cause I because I finally figured out the most important thing about investing

18:30

I had a I had a company today that I was a, investor and that just it just kinda did a re or they they just announced the reverse merger. They're going public. So, hopefully, that will do well. But I've been I I've been an investor in a lot of companies that have done well because, like, because I finally figured out the most important thing about investing

18:46

that I missed before.

18:46

that I missed before.

18:47

And that since then, my private investing has done very well, and I don't really do public investing. Well, what's that thing?

18:47

And that since then, my private investing has done very well, and I don't really do public investing. Well, what's that thing?

18:53

That one thing is that I am

18:53

That one thing is that I am

18:56

the worst idiot in the world. If if you're in a room with me, I'm the stupidest person in that room. And what I mean by that is,

18:56

the worst idiot in the world. If if you're in a room with me, I'm the stupidest person in that room. And what I mean by that is,

19:04

take Buddy Media as an example.

19:04

take Buddy Media as an example.

19:07

I didn't have to do any work once I invested because Peter Till was my co investor.

19:07

I didn't have to do any work once I invested because Peter Till was my co investor.

19:11

So it's not like they're gonna call me for advice. They're gonna call the people smarter than me. And also presumably, the first investor in Facebook

19:11

So it's not like they're gonna call me for advice. They're gonna call the people smarter than me. And also presumably, the first investor in Facebook

19:19

would know what he was doing when investing in a in a Facebook marketing agency, which is what Buddy Media was. So

19:19

would know what he was doing when investing in a in a Facebook marketing agency, which is what Buddy Media was. So

19:27

so I always

19:27

so I always

19:29

if someone a lot smarter than me says, hey, I'm investing in this company. I don't even have to do any more work. I just send the check. Because I assume and I'm always correct when I assume this, he's done or she's done all the due diligence,

19:29

19:41

all the hard work, He's he's got PhDs working for him that are a lot smarter than me.

19:41

all the hard work, He's he's got PhDs working for him that are a lot smarter than me.

19:46

Worse comes to worst,

19:46

Worse comes to worst,

19:48

he or she can make phone calls and get this company acquired, which is what happens And

19:48

he or she can make phone calls and get this company acquired, which is what happens And

19:53

I've done very well with just that one strategy that if someone a lot smarter than me is investing at the same terms as me, that's important too. Then I'm going to do well. And it's almost like a hundred it's not like a normal success rate. It's like a hundred percent success rate when you do And and the other rule is if they ever call me for advice,

19:53

20:12

then on my spreadsheet where I keep track of these, I assume their value is zero, and I never call them back. Because if they're if that if they've reached so far down the totem pole where they have to call me for advice, that means they're screwed. So and this secret works. Like, it's amazing how well that one technique works. And so that allows me to invest in

20:12

20:32

at companies ranging from oil companies to tech, to law enforcement,

20:32

at companies ranging from oil companies to tech, to law enforcement,

20:36

to the company today as an erectile dysfunction drug. I don't that I don't know anything about biotech, like, the

20:36

to the company today as an erectile dysfunction drug. I don't that I don't know anything about biotech, like, the

20:44

but as long as someone

20:44

but as long as someone

20:45

you know, if if someone calls me and says, look, hey, I've I've started the last

20:45

you know, if if someone calls me and says, look, hey, I've I've started the last

20:51

three erectile dysfunction drug companies, and they've all done well. Now I'm investing in this. Are you with me? Here's my check. I don't need to know anything else. I think, I think Sean's gonna wanna ask you questions on Angel Investing, and I wanna ask them I wanna hear his answer or your answers to those questions. But before we get to that, what about selling? I mean, so you've sold, more than a handful of businesses selling companies is hard. Most people will never sell one. How are you how are you able to,

20:51

21:17

sell so many you think? You know, that that's a that's a great question because and let me ask you, Sam, I don't know if we've talked about this. Have you ever sold a company?

21:17

sell so many you think? You know, that that's a that's a great question because and let me ask you, Sam, I don't know if we've talked about this. Have you ever sold a company?

21:25

I had a small, like, hundreds of thousands of dollars sale. For this company,

21:25

I had a small, like, hundreds of thousands of dollars sale. For this company,

21:30

the hustle, we had term sheets, and I walked away at the last minute. I've had two or three term sheets, and I've walked away from them, and I've never closed the deal.

21:30

the hustle, we had term sheets, and I walked away at the last minute. I've had two or three term sheets, and I've walked away from them, and I've never closed the deal.

21:38

Yes. So so And then I've bought I've also helped buy companies too.

21:38

Yes. So so I've bought I've also helped buy companies too.

21:42

Yeah. So it's a similar it's similar skills on both sides of of maybe slightly different, but

21:42

Yeah. So it's a similar it's similar skills on both sides of of maybe slightly different, but

21:48

people don't realize selling a company is very difficult. Like, it's there's three skills. There's starting a company. There's building it, and there's selling it. And Sean stole his company too to Twitch. Yeah. Last year. Congratulations for you. Yeah. And you so you know what I'm talking about. Like, you'll you'll your company's up for sale and everybody's

21:48

22:09

and you meet a bunch of people. I don't know if you met a bunch of people, but, like, I would meet a bunch of people each time.

22:09

and you meet a bunch of people. I don't know if you met a bunch of people, but, like, I would meet a bunch of people each time.

22:14

And,

22:14

And,

22:15

you kind of there's this courtship and you kind of fall in love with each other, like, just like in a courtship. And then there's

22:15

you kind of there's this courtship and you kind of fall in love with each other, like, just like in a courtship. And then there's

22:22

and then there's suddenly

22:22

and then there's suddenly

22:23

you move into a different period where lawyers take over and you're waiting. It's a waiting period and it's a due diligence period. And it's a very painful

22:23

you move into a different period where lawyers take over and you're waiting. It's a waiting period and it's a due diligence period. And it's a very painful

22:32

period. Because before you were in this, like, massive selling and dating mood, but now you're, like, living together and you're getting to know each other. And

22:32

period. Because before you were in this, like, massive selling and dating mood, but now you're, like, living together and you're getting to know each other. And

22:41

you know, you don't want her to figure this out too fast.

22:41

you know, you don't want her to figure this out too fast.

22:44

And, you know, before she really falls in love, and,

22:44

And, you know, before she really falls in love, and,

22:47

you know, and all that Dopa mean you get when you first meet has gone away. And it's By the way, that's when I started this podcast was during the due diligence period because I got so itchy. Because I was waiting. And I was like, oh my god. I'm I'm gonna jeopardize this deal either because I'm gonna push too hard,

22:47

23:02

just because I'm impatient. I'm gonna go start another business, which is the worst thing I could do while I'm trying to sell this one. So I was like, I need to do something. And so that's why I started the podcast was during that due diligence period. Yeah. That's smart because I would just do nothing but wait. And,

23:02

23:17

it's it's it's a painful process. And the way you sell is, first off,

23:17

it's it's it's a painful process. And the way you sell is, first off,

23:22

you have to

23:22

you have to

23:23

and this is not you have to be sincere the whole way through. You have to have a vision that matches

23:23

and this is not you have to be sincere the whole way through. You have to have a vision that matches

23:29

their vision very strongly, and it has to explain

23:29

their vision very strongly, and it has to explain

23:33

Why you would if this your business is so great, why do you wanna sell it? Like, there's that inherent contradiction in selling a business. And

23:33

Why you would if this your business is so great, why do you wanna sell it? Like, there's that inherent contradiction in selling a business. And

23:40

I was always aware that I would, you know, in every business I've sold, that I would be better off with a better capitalized

23:40

I was always aware that I would, you know, in every business I've sold, that I would be better off with a better capitalized

23:47

partner. And now maybe I would limit my upside.

23:47

partner. And now maybe I would limit my upside.

23:51

But, you know, the first time you saw a company for millions, and then the second time, if you're broke the second time you slow a company for millions, and then the third time,

23:51

But, you know, the first time you saw a company for millions, and then the second time, if you're broke the second time you slow a company for millions, and then the third time,

23:58

it's okay to not sell for billions because you wanna get that initial

23:58

it's okay to not sell for billions because you wanna get that initial

24:03

chunk. But You also have to say, look, together, here's how it's one plus one equals three. And you have to be really persuasive

24:03

chunk. But You also have to say, look, together, here's how it's one plus one equals three. And you have to be really persuasive

24:10

24:11

on why one plus one equals three. Even for you personally, like, you have to be able to express that this vision is gonna benefit you personally

24:11

on why one plus one equals three. Even for you personally, like, you have to be able to express that this vision is gonna benefit you personally

24:18

if you partner with this other company and and

24:18

if you partner with this other company and and

24:21

and and it has to really make sense. And then and then, of course, you have to survive this waiting period You have to survive the initial period where they're still checking you out, but now you're together, and you have to integrate and get along, and you have to keep all your employees because usually there's some back end earn out or something like that. Like the every you have to understand deal structure so you're not ripped off. It's very easy to be ripped off by lawyers in a deal, and people don't realize that. And you have to be you have to have some skills at negotiation,

24:21

24:48

which negotiating is one of those things that nine out of ten people think that they're above average which is impossible. Like, you have to be four out of ten. Only could be above the median,

24:48

which negotiating is one of those things that nine out of ten people think that they're above average which is impossible. Like, you have to be four out of ten. Only could be above the median,

24:57

and only one out of ten is really good enough to to sell a company properly.

24:57

and only one out of ten is really good enough to to sell a company properly.

25:02

And so I had to learn the hard way how to negotiate.

25:02

And so I had to learn the hard way how to negotiate.

25:05

And then, like, when they come to you and they say, well, how much do you want for your company? That's a very hard question to answer.

25:05

And, like, when they come to you and they say, well, how much do you want for your company? That's a very hard question to answer.

25:11

Because you don't wanna sound greedy and you don't wanna sound desperate and you don't wanna sound and you don't wanna underprice yourself. So there's all sorts of negotiating techniques

25:11

Because you don't wanna sound greedy and you don't wanna sound desperate and you don't wanna sound and you don't wanna underprice yourself. So there's all sorts of negotiating techniques

25:19

that you have to use

25:19

that you have to use

25:21

to to help them answer that question in a way that works for both sides. Not just for you. Did you value your companies on a multiple of your profit or revenue, or was it, if you use our stuff with your audience or your current products, it it will create this much value. So That also is a really great question because

25:21

25:40

there's there's three ways to value a company. Right? The one is a a standard industry multiple on your earnings and cut it in half. By the way, because no one's gonna pay the maximum, you cut it in half so they everybody wants to get a deal. So, like, if if you have a profitable company and it's an industry that trades on the stock market for twenty times earnings, then your company is probably your last year's profits times ten, the twenty divided by two.

25:40

26:05

That's just a basic formula. Or you could do what you just said, which is, hey, and I learned this for my second company. I didn't live in this for my fur my first company was profitable. Unlike every other internet company. And so we sold for about

26:05

26:17

ten times earnings,

26:17

ten times earnings,

26:19

which was was was a mistake.

26:19

which was was was a mistake.

26:23

The second company

26:23

The second company

26:24

was, like, I did value it like how you said, which is,

26:24

was, like, I did value it like how you said, which is,

26:28

if if you

26:28

if if you

26:30

if we put ads all over here, and you're driving this amount of traffic. And, we monetize those ads, and then you cut that in half. This is what we're worth. And I the second company I sold on the basis of that.

26:30

26:44

The challenge there is with the other company, you work out this formula for how you're gonna value

26:44

The challenge there is with the other company, you work out this formula for how you're gonna value

26:49

your company based on their

26:49

your company based on their

26:52

their

26:52

their

26:53

them helping you build your earnings. And the challenges then you fill in all the variables

26:53

them helping you build your earnings. And the challenges then you fill in all the variables

26:58

they know the variables better than you. So you have to make sure when you're negotiating the formula

26:58

They know the variables better than you. So you have to make sure when you're negotiating the formula

27:03

that and you agree on the formula that you understand the variables enough to that it works out to what you want. I didn't do that part properly on my second negotiation.

27:03

that and you agree on the formula that you understand the variables enough to that it works out to what you want. I didn't do that part properly on my second negotiation.

27:12

And then the third way to value things is look at other companies acquired in the space. They sold for this. We're bigger. So we should be this. Now that's kind of a BS way to value a company, but that is how people value

27:12

27:24

companies often, particularly in the in the tech sector. Like, Giphy, I don't know what the how they value themselves, but certainly wasn't off of earnings. I don't think they had twenty million dollars in earnings. My guess is they were losing money. So,

27:24

27:37

so they probably valued off of something, some kind of comparable

27:37

so they probably valued off of something, some kind of comparable

27:40

deal in in the internet. Yeah. Because tenor sold tenor, which is if he's competitor just sold to Google a year before for a little less than that.

27:40

deal in in the internet. Yeah. Because tenor sold tenor, which is if he's competitor just sold to Google a year before for a little less than that.

27:49

Oh, who is their competitor? Ten a company called Tener, t e n o r. They were And and their competitor. Yeah. It it just as a side. Is it true that Giphy was the second largest attention in the world. That's what they're saying. Yeah. I don't think it's the largest is yeah. They love it. I thought YouTube was. Yeah. So YouTube is number two and Amazon is

27:49

28:08

three. Amazon four. Right? Like, so Yeah. Depends what you call a search engine.

28:08

three. Amazon four. Right? Like, so Yeah. Depends what you call a search engine.

28:12

But I I did interview the founder in New York and it is huge. It was just,

28:12

But I I did interview the founder in New York and it is huge. It was just,

28:19

there was no way to make money off of it, really.

28:19

there was no way to make money off of it, really.

28:21

Yeah. I had that issue. I was I was a seed investor and on the board of bitly.

28:21

Yeah. I had that issue. I was I was a seed investor and on the board of bitly.

28:26

So bitly had about five percent of the internet's traffic every day running through it. And for the life of us, we just could not figure out how to monetize it. Like, it was impossible. And they did exit the pro a private equity firm bought it, but it was like a a two or three x, which is not really what you're looking for in a angel investment. And so James, when you lose your you lose all your money the first time, you call back, you make money again, doing something else, you lose it again. I mean, obvious question, at some point where you're like, okay, rainy day fun. Two million bucks is going into this account, and, hey, I lost the, I lost the keys.

28:26

28:59

Just a, you know, like, just to stash some money away.

28:59

Just a, you know, like, just to stash some money away.

29:02

What? Yeah. Surely, your wife was like, come on, man. Yeah. How did you get away with not just saving some of money?

29:02

What? Yeah. Surely, your wife was like, come on, man. Yeah. How did you get away with not just saving some of money?

29:08

I got divorced.

29:08

I got divorced.

29:10

Alright. There we go. That was a problem. And I lost the second house that I bought. And,

29:10

Alright. There we go. That was a problem. And I lost the second house that I bought. And,

29:16

no. I I kind of finally, I think it was the third time or the fourth time. I finally looked back and I said, what was I always doing right on the way up? And what was I doing wrong on the way down?

29:16

no. I I kind of finally, I think it was the third time or the fourth time. I finally looked back and I said, what was I always doing right on the way up? And what was I doing wrong on the way down?

29:27

And

29:27

And

29:28

there were things in common, which is just that I kind of

29:28

there were things in common, which is just that I kind of

29:32

I kind of would just give up after I made a lot of money. I would kind of say, whew. I I did my job as a human. Now I can just let my health go away, my relationships. I don't care about it anymore. I don't need to be creative anymore.

29:32

29:45

You know, I don't need to have any kind of sense of spirituality,

29:45

You know, I don't need to have any kind of sense of spirituality,

29:49

and I would just whatever. And I just would lose all sense of things and and not take care of myself, and not just physically, but, like, emotionally and creatively.

29:49

and I would just whatever. And I just would lose all sense of things and and not take care of myself, and not just physically, but, like, emotionally and creatively.

29:58

And so I just made it a very concentrated effort. And it sounds sort of cliche and almost self help help me a little bit. But I really would make a concerted effort to keep myself physically healthy,

29:58

And so I just made it a very concentrated effort. And it sounds sort of cliche and almost self help help me a little bit. But I really would make a concerted effort to keep myself physically healthy,

30:10

to have only good people in my life and quickly eliminate

30:10

to have only good people in my life and quickly eliminate

30:13

any talks with people. Like, it's like the speed of light. No

30:13

any talks with people. Like, it's like the speed of light. No

30:17

second chances.

30:17

second chances.

30:18

And

30:18

And

30:19

creatively,

30:19

creatively,

30:20

I I just started writing down every single day ten ideas a day. Like,

30:20

I I just started writing down every single day ten ideas a day. Like,

30:26

and it could it could be business ideas. It could be writing ideas. It could be dumb ideas. It could be ideas for TV shows. It could be ideas for how Google could be a better search engine, and then I would arrogantly send them to Google. But the whole idea was not to have good ideas, but to just practice this creativity muscle or else it would atrophy.

30:26

30:46

And

30:46

And

30:47

literally,

30:47

literally,

30:48

like,

30:48

like,

30:49

I'm not I'm not trying to sell anything here. Like, literally within months of writing ten ideas a day down, it it it felt as my whole brain was rewired. And I would just I would bounce back so quickly with ideas.

30:49

31:02

It was just nonstop.

31:02

It was just non stop. And then the aspect of sometimes I would write ideas,

31:03

And then the aspect of sometimes I would write ideas

31:07

for for other companies, and I would send them these ideas if I thought they were pretty good. And you know, I would always get new opportunities because of that. Like, I would visit Facebook, Amazon, LinkedIn, Google,

31:07

for other companies, and I would send them these ideas if I thought they were pretty good. And you know, I would always get new opportunities because of that. Like, I would visit Facebook, Amazon, LinkedIn, Google,

31:18

Quora,

31:18

Quora,

31:19

Airbnb,

31:19

Airbnb,

31:21

And just

31:21

And just

31:22

just the this one process of writing ten ideas a day down for the past twelve years has been such an incredible

31:22

just the this one process of writing ten ideas a day down for the past twelve years has been such an incredible

31:28

thing for me. I can't even praise it enough. So the other day, just for fun, a friend of mine recently took a job at Disney plus,

31:28

thing for me. I can't even praise it enough. So the other day, just for fun, a friend of mine recently took a job at Disney plus,

31:36

And he was just like, because of this lockdown, we're not getting any good ideas pitched to us. So I'm like, well, what are you looking for? And he said we're looking specifically

31:36

And he was just like, because of this lockdown, we're not getting any good ideas pitched to us. So I'm like, well, what are you looking for? And he said we're looking specifically

31:45

for unscripted ideas that would cater to nine year olds. So I wrote my list of ten ideas the next day, and I sent it to him. He forwarded it to the I don't know how, like, he forwarded to the head of reality programming at Disney.

31:45

32:00

And at right after this, I'm meeting they they got excited right after this. I'm meeting,

32:00

And at right after this, I'm meeting they they got excited right after this. I'm meeting,

32:04

with Disney

32:04

with Disney

32:05

to go over the ideas.

32:05

to go over the ideas.

32:08

That's wild.

32:08

That's wild.

32:09

What was there,

32:09

What was there,

32:11

as someone who's gone up and down and up and down, can you explain what your happiness levels went, like, what the range was from, like, let's say zero dollars to ten thousand dollars to a hundred to like one million to fifteen million.

32:11

32:24

Like, what what's the difference in your happiness and fulfillment and things like that? Oh my god. So and and, really, we're just talking about the first time because then there's different it's different each time. But,

32:24

32:36

I had zero dollars

32:36

I had zero dollars

32:38

in the bank, and I was living in a

32:38

in the bank, and I was living in a

32:41

studio in Astoria Queens, which is you know, was not in the nine early nineties. It was not a nice part of Queens. Before that, I had a a roommate in a in a apartment smaller than the room. You're seeing me in and

32:41

32:54

I was paying three hundred dollars a month. I was working at HBO for forty thousand

32:54

I was paying three hundred dollars a month. I was working at HBO for forty thousand

32:59

a year. I was I had a a a suit in a garbage bag that I would pull out every day and put on the same suit seven days in a row and walk over to HBO.

32:59

a year. I was I had a a a suit in a garbage bag that I would pull out every day and put on the same suit seven days in a row and walk over to HBO.

33:08

And then we did the very first site I did. Was this diamond dealer,

33:08

And then we did the very first site I did. Was this diamond dealer,

33:13

and,

33:13

and,

33:14

he gave me seventeen thousand five hundred dollars in cash. This is nineteen ninety four.

33:14

he gave me seventeen thousand five hundred dollars in cash. This is nineteen ninety four.

33:20

And I hadn't I had never had seen any money like this before. Seventeen thousand five like, almost was like, I couldn't believe this was actually happening.

33:20

And I hadn't I had never had seen any money like this before. Seventeen thousand five like, almost was like, I couldn't believe this was actually happening.

33:27

And I walked over to the Chelsea Hotel on twenty third street. It was, like, this sort of famous artsy hotel, but also really rundown

33:27

And I walked over to the Chelsea Hotel on twenty third street. It was, like, this sort of famous artsy hotel, but also really run down. And I gave the owner, like, the whole bag was a paper bag of seventeen thousand five hundred dollars and said, can I live here for a year? And he said, are you a drug dealer? And I said, no, I work at HBO and he let me live there. And I was just so happy, like, oh, I'm living in Manhattan now and in this cool hotel.

33:35

And I gave the owner, like, the whole bag was a paper bag of seventeen thousand five hundred dollars and said, can I live here for a year? And he said, are you a drug dealer? And I said, no, I work at HBO and he let me live there. And I was just so happy, like, oh, I'm living in Manhattan now and in this cool hotel.

33:53

And I felt like part of something. I felt like part of a scene. I felt magical.

33:53

And I felt like part of something. I felt like part of a scene. I felt magical.

33:57

And,

33:57

And,

33:59

that was an amazing moment. And then when I sold that first business,

33:59

that was an amazing moment. And then when I sold that first business,

34:02

I felt good,

34:02

I felt good,

34:04

but it was weird because it was so much pain closing that deal. Like, I was so stressed out in the months prior to that And I I got burnt out, and that's when I started playing poker every single night just to kind of escape burnout. So I don't know if I was happy or or just more escapist

34:04

34:18

then and then when I started losing and every time I've lost every single time I've lost everything, I was suicidal.

34:18

then and then when I started losing and every time I've lost every single time I've lost everything, I was suicidal.

34:25

And

34:25

And

34:26

in part for practical reasons, I thought maybe my my kids could live off my life insurance and particularly that first time there were babies So I figured they wouldn't remember me, but they'll definitely remember the

34:26

34:38

life insurance.

34:38

life insurance.

34:39

So,

34:39

So,

34:41

fortunately,

34:41

fortunately,

34:42

I I I couldn't figure out how to do it in such a way as to not hurt myself,

34:42

I I I couldn't figure out how to do it in such a way as to not hurt myself,

34:46

and I never did it. And,

34:46

and I never did it. And,

34:49

you know, I was very depressed though for long periods of time. But each time, the period of depression would get,

34:49

you know, I was very depressed though for long periods of time. But each time, the period of depression would get,

34:55

faster and faster.

34:55

faster and faster.

34:57

And, you know, I think one of the most probably

34:57

And, you know, I think one of the most probably important things I've been learning. You know, I used to think learning is like, you know, in school, it's like, learn math. And then as you get a little bit older, you're like, oh, maybe I should learn some skills, like sales or programming or whatever. And now I'm like, oh, fuck all that. The only skill that matters is sort of, managing my own psychology, my own emotions. And so I started to, you know, out what works for me. Right? Like,

35:00

important things I've been learning. You know, I used to think learning is like, you know, in school, it's like, learn math. And then as you get a little bit older, you're like, oh, maybe I should learn some skills, like sales or programming or whatever. And now I'm like, oh, fuck all that. The only skill that matters is sort of, managing my own psychology, my own emotions. And so I started to, you know, out what works for me. Right? Like,

35:21

cool. If I

35:21

cool. If I

35:22

exercise, here's how I feel. If I, you know, eat this, if I make this decision, if I listen to this song, whatever. I started to find different little ways,

35:22

exercise, here's how I feel. If I, you know, eat this, if I make this decision, if I listen to this song, whatever. I started to find different little ways,

35:32

to manage my own psychology.

35:32

to manage my own psychology.

35:34

Do you have a sort of any things that you've worked on or you figured that help you either, you know,

35:34

Do you have a sort of any things that you've worked on or you figured that help you either, you know,

35:40

boost up gratitude or, like, you know, get out of that depression funk.

35:40

boost up gratitude or, like, you know, get out of that depression funk.

35:44

What works for you or or or do you are you conscious about that?

35:44

What works for you or or or do you are you conscious about that?

35:47

Yeah. Very very much so. And that was part of this

35:47

Yeah. Very very much so. And that was part of this

35:50

realization that every single day, and I even I it it's I call it my specific daily practice, and it's it could be different for each person, but I always have to ask, what am I doing to eat, move, sleep. So that's physical health. I always try to stay healthy. Like, I'm not I don't I'm not an athlete. I'm not a,

35:50

36:10

you know, I'm not used to working out or I mean, I'm fifty two years old. I've gotta stay as healthy as possible.

36:10

you know, I'm not used to working out or I mean, I'm fifty two years old. I've gotta stay as healthy as possible.

36:16

And so eat every day, I have to make sure I'm eating well, sleeping eight hours, and and moving.

36:16

And so eat every day, I have to make sure I'm eating well, sleeping eight hours, and and moving.

36:22

And now with this pandemic lockdown is I have to go outside and make sure I have some outside time. And then emotional

36:22

And now with this pandemic lockdown is I have to go outside and make sure I have some outside time. And then emotional health

36:27

health,

36:30

Just what how much

36:30

Just what how much

36:32

are are the people around me toxic or not? And that is the key to emotional health, nothing else. And then creative health. Am I writing ten ideas a day down? Because creativity,

36:32

are are the people around me toxic or not? And that is the key to emotional health, nothing

36:37

else. And then creative health. Am I writing ten ideas a day down? Because creativity,

36:43

not only is it rewiring your brain to be more creative, you know, or that muscle atrophies, but it also

36:43

not only is it rewiring your brain to be more creative, you know, or that muscle atrophies, but it also

36:49

triggers a lot of dopamine when you're creative. And it just if I do it in the morning to work on my ten ideas of day list, I've got this surge of dopamine that carries me at least till, like, one or two in the afternoon. And then

36:49

triggers a lot of dopamine when you're creative. And it just If I do it in the morning, to work on my ten ideas of day list, I've got this surge of dopamine that carries me at least till, like, one or two in the afternoon. And then

37:02

spiritual health is just am I trying to control things I can't control?

37:02

spiritual health is just am I trying to control things I can't control?

37:06

So that's a very important part of spiritual health. So you see people on Twitter all day long.

37:06

So that's a very important part of spiritual health. So you see people on Twitter all day long.

37:11

Oh, man. They should open we need to open up this economy right now, or we need to lock down all the people over there. Like, on both sides, they're trying to control things they can't control, and they're all day long. They're twenty per hours a day on Twitter. And

37:11

37:23

even during this pandemic, I felt like I was getting a little into that, and then I pulled myself back and realized it just wasn't I can't control this, so

37:23

even during this pandemic, I felt like I was getting a little into that, and then I pulled myself back and realized it just wasn't I can't control this, so

37:32

it wasn't healthy for me. And so always avoiding trying to control things you can't control is is very important. And that really Just those four things, physical, emotional, creative spiritual, just those four things. If I attend to them every day, I I keep at a very high state. And even when I'm even when I lose money now or go up in money, I it keeps me very,

37:32

37:51

you know, contentment and well-being are much more important than happiness. Happiness is very as the cliche goes is very fleeting, but well-being,

37:51

you know, contentment and well-being are much more important than happiness. Happiness is very as the cliche goes is very fleeting, but well-being,

38:00

you build a real foundation of well-being, and that and that sticks with you. So what's your business now, James, that you're that, like, what's, like, your job now?

38:00

you build a real foundation of well-being, and that and that sticks with you. So what's your business now, James, that you're that, like, what's, like, your job now?

38:09

Well, I do I do lots of things. So

38:09

Well, I do I do lots of things. So

38:11

I mean, I I write every day, and I'm I just finished a book that will be published by Harper Collins in a year.

38:11

I mean, I I write every day, and I'm I just finished a book that will be published by Harper Collins in a year.

38:19

I do a podcast.

38:19

I do a podcast.

38:20

I I I'm still involved in my newsletter business, which I sold.

38:20

I I I'm still involved in my newsletter business, which I sold.

38:25

I'm a I'm a private investor in about two dozen private companies. So I'm I but I'm remember, I'm not active in those

38:25

I'm a I'm a private investor in about two dozen private companies. So I'm I but I'm remember, I'm not active in those

38:33

because they don't I don't want them to want my advice So it's very, very passive, but I have to make sure I'm enough in the deal flow that each year I can still put a little bit of money to work because you never know which year you'll find the next Uber or whatever.

38:33

because

38:34

they don't I don't want them to want my advice So it's very, very passive, but I have to make sure I'm enough in the deal flow that each year I can still put a little bit of money to work because you never know which year you'll find the next Uber or whatever.

38:48

And,

38:48

And,

38:49

and a lot of my time, the past five years, until this lockdown has been on stand of comedy,

38:49

and a lot of my time, the past five years, until this lockdown has been on stand of comedy,

38:56

which makes,

38:56

which makes,

38:57

you know, which makes minimal at best. So then did did you're not your angel money, that came from, like, your initial sale.

38:57

you know, which makes minimal at best. So then did did you're not your angel money, that came from, like, your initial sale.

39:07

Really, really now most the way I make a living and the way I built up is just from private investing because pretty much every company I've sold, I ended up losing all or most of the money. But private investing is now the way I've been able to make a living most of all. So on the angel front, so what percent of your money do you of your, like, net worth do you put into angel deals

39:07

39:31

which is a risky illiquid thing. I'm very much now. And this is this was the key point

39:31

which is a risky illiquid thing. I'm very much now. And this is this was the key point

39:36

that made a big difference for me in investing. Is that risk is the most important part of investing. Whether you're investing money or you're investing time,

39:36

that made a big difference for me in investing. Is that risk is the most important part of investing. Whether you're investing money or you're investing time,

39:45

re risk

39:45

re risk has to be managed and thought about first and foremost. And the way I remove risk is two ways. One is, as I mentioned, I always invest with people who are smarter than me, because I let that I outsource

39:46

has to be managed and thought about first and foremost. And the way I remove risk is two ways. One is, as I mentioned, I always invest with people who are smarter than me, because I let that I outsource

39:57

some of the risk management to people who are professionals at it. And the other way I manage risk is position size. So I never invest more than

39:57

some of the risk management to people who are professionals at it. And the other way I manage risk is position size. So I never invest more than

40:07

one to two percent of my net worth is the maximum

40:07

one to two percent of my net worth is the maximum

40:11

I will ever invest in any

40:11

I will ever invest in any

40:13

company. Now I'll let I'll let the investment grow to much more than that. It's sort of like what Warren Buffett says, if you've got Michael Jordan on your team, you don't trade him just because he got better. So I I I like it when

40:13

40:26

good private companies don't exit.

40:26

good private companies don't exit.

40:28

Because that means they're growing still at like fifty to two hundred percent a year. And as long as they're doing that, I don't want them to exit. And what was your biggest Angel or private company win so far.

40:28

40:40

Which which company?

40:40

Which which company?

40:42

Yeah. It's it's it's hard to say because a lot of my investments are doing really well, but they're still private. Like, I have deals I invested in in two thousand nine, which are still doubling every year, but

40:42

40:52

they

40:52

they they're they're still private.

40:53

they're they're still private.

40:55

But

40:55

But

40:56

that buddy media one, you know, four million to

40:56

that buddy media one, you know, four million to

40:59

seven hundred million was pretty good. Ticketfly.

40:59

seven hundred million was pretty good. Ticketfly.

41:02

Was another one I invested in, which, I was in the seat round of that, and it sold for four hundred fifty million.

41:02

Was another one I invested in, which, I was in the seat round of that, and it sold for four hundred fifty million.

41:09

I invested in another one, which is public now, It's a law enforcement company. They have a a gun that if they

41:09

I invested in another one, which is public now, It's a law enforcement company. They have a a gun that if they

41:17

we I was sort of a cofounder of this. It started in the living room I was staying at And

41:17

we I was sort of a cofounder of this. It started in the living room I was staying at And

41:23

the there was a hashtag Black Lives Matter was the trending hashtag. And so we tried to solve that problem, basically. So we found an inventor who made a gun that fires a kevlar cable at you at the speed of sound and it wraps around you the more you try to struggle to get out of it, it squeezes tighter.

41:23

41:40

And so, like like a Batman. Yeah. That was gonna say straight out of Batman.

41:40

And so, like like a Batman. Yeah. That was gonna say straight out of Batman.

41:44

Yeah. And even the the of the founders of TASER is the president of the company now. He became the president of the company about a year ago, and we went public.

41:44

Yeah. And even the the of the founders of TASER is the president of the company now. He became the president of the company about a year ago, and we went public.

41:52

It's it's a really great company. It's still in in growth mode, but they're starting to to sell quite a bit. And,

41:52

It's it's a really great company. It's still in in growth mode, but they're starting to to sell quite a bit. And,

41:59

that that's been I'm not exited, actually. I'm I own shares of the public company. I'm not planning on exit, hopefully, ever because it's it's it's What's the name of it? No competition.

41:59

that that's been I'm not exited, actually. I'm I own shares of the public company. I'm not planning on exit, hopefully, ever because it's it's it's What's the name of it? No competition.

42:08

The company is called RAP Technologies. So I'm not trying to push stock or anything. So I don't wanna even mention the the stock stock symbol. But,

42:08

The company is called RAP Technologies. So I'm not trying to push stock or anything. So I don't wanna even mention the the stock stock symbol. But,

42:16

it's it's it's just such a great thing to invest in and be a part of the founding of something that's literally saves lives every single day. So so Can you, can you do you have the journal with you that you write your ten ideas? Can we can we get a random day? Let's Let's talk about the ideas. Like, what what are you what's interesting to you right now, James?

42:16

42:34

A lot of times, it's in my email. Oh, there's my pad. I do it all in waiters pads, or I do it in my email. So if I'm out at a cafe, I do it in a waiter's pad. And if I do it at,

42:34

A lot of times, it's in my email. Oh, there's my pad. I do it all in waiters pads, or I do it in my email. So if I'm out at a cafe, I do it in a waiter's pad. And if I do it at,

42:44

sitting at my computer, I'll do it in my email. Well, as a as an angel investor, and I don't know if you're ever gonna start another company again. Maybe you are, maybe you aren't, but as someone who's always scheming, what, what do you have your eye on now? Yeah. I have no problem even saying what I'm scheming at because,

42:44

sitting at my computer, I'll do it in my email. Well, as a as an angel investor, and I don't know if you're ever gonna start another company again. Maybe you are, maybe you aren't, but as someone who's always scheming, what, what do you have your eye on now? I have no problem even saying what I'm scheming at because,

42:58

so I've I I haven't considered starting a a new company in a very long time, but I have been considering it now.

42:58

so I've I I haven't considered starting a a new company in a very long time, but I have been considering it now.

43:05

And one of the ideas is I feel

43:05

And one of the ideas is I feel

43:08

it's a shame

43:08

it's a shame that

43:09

that content is not monetized.

43:10

content is not monetized.

43:12

Unless you're like the in the top one tenth to one percent of content creators. So you have to be like, you know, Logan Paul to monetize your YouTube channel.

43:12

Unless you're like the in the top one tenth to one percent of content creators. So you have to be like, you know, Logan Paul to monetize your YouTube channel.

43:21

And the other twenty billion people on YouTube,

43:21

And the other twenty billion people on YouTube,

43:24

even if they have one video that goes viral, they can't monetize it. So

43:24

even if they have one video that goes viral, they can't monetize it. So

43:29

or or, like, even if you have a if you have a tweet that twenty million people see, but you have only three hundred followers,

43:29

or or, like, even if you have a if you have a tweet that twenty million people see, but you have only three hundred followers,

43:34

you can't

43:34

you can't

43:35

monetize it. So I've been figuring out a way to use

43:35

monetize it. So I've been figuring out a way to use

43:39

these ecosystems

43:39

these ecosystems

43:40

to allow people to monetize content. So that's one idea I'm working on. Actually,

43:40

to allow people to monetize content. So that's one idea I'm working on.

43:45

Actually, physically working on it. And another one involves,

43:45

physically working on it. And another one involves,

43:49

making

43:49

making

43:50

a derivative of a of a board game that I like.

43:50

a derivative of a of a board game that I like.

43:53

But

43:53

But

43:54

in general, I don't I don't come up with business ideas. I come up with like like I said the other day, I had this challenge, like, of, oh, I'm gonna challenge myself to come up with TV show ideas that nine year olds would like. And I did that and I sent it off. And usually, I don't send it off. Or sometimes the ideas are ideas for books I could write or if I have an idea for a book I could write, I the next idea, I'll write a list of chapter titles.

43:54

44:17

And again,

44:17

And again,

44:19

Most of the ideas are supposed to be bad because you can't come up with three thousand six hundred fifty good ideas a year, and it'd be foolish to think so. So I'm just trying to come up with bad ideas, but I'm trying to make my brain sweat. So for instance, one idea list that is particularly hard and this is the one I wrote this morning is

44:19

44:38

ten good positive things that have happened to me personally because of this lockdown.

44:38

ten good positive things that have happened to me personally

44:41

because

44:42

of this lockdown.

44:44

Those aren't actionable ideas,

44:44

Those aren't actionable ideas,

44:46

but it was actually hard to come up with ten. Like,

44:46

but it was actually hard to come up with ten. Like,

44:50

one through seven is always usually pretty easy, but eight nine ten is usually makes I feel like my brain sweating.

44:50

one through seven is always usually pretty easy, but eight nine ten is usually makes I feel like my brain sweating.

44:56

And,

44:56

And,

44:57

but, yeah, but a lot of times, I'll come up with business ideas or I'll I'll start to say to myself what industries are gonna be attractive after this that are unexpected.

44:57

but, yeah, but a lot of times, I'll come up with business ideas or I'll I'll start to say to myself what industries are gonna be attractive after this that are unexpected.

45:05

So you can't say the obvious ones. Like, obviously,

45:05

So you can't say the obvious ones. Like, obviously,

45:08

you know, video communications technology is gonna be,

45:08

you know, video communications technology is gonna be,

45:13

attractive

45:13

attractive businesses after this Instead, I would think what are the ten ways I can improve on Zoom, which was the is the most popular one right now. So that will be how I exercise

45:14

businesses after this Instead, I would think what are the ten ways I can improve on Zoom, which was the is the most popular one right now. So that will be how I exercise

45:24

the idea muscle around zoom. And For your for your content idea, is there a comp out there? Like, is there somewhere something out there that you're like, man, this, like, little behavior that some people are doing, I think that if we just blew this up or systemize this, this could actually have legs.

45:24

45:40

Yeah. So sort of. So I'll do something what I'll call

45:40

Yeah. So sort of. So I'll do something what I'll call

45:44

what I call idea sex. So I'll take

45:44

what I call idea sex. So I'll take

45:47

ideas from two completely different industries. And again, I've been a professional in many different industries

45:47

ideas from two completely different industries. And again, I've been a professional in many different industries

45:53

again, fortunately or unfortunately,

45:53

again, fortunately or unfortunately,

45:55

and I'll combine

45:55

and I'll combine

45:57

ideas to see if

45:57

ideas to see if

45:58

after idea six, there's a little idea, baby,

45:58

after idea six, there's a little idea, baby, that could work in in what I'm doing. So for instance,

46:01

that could work in in what I'm doing. So for instance,

46:05

if I go to a restaurant and have a pretty good meal,

46:05

if I go to a restaurant and have a pretty good meal,

46:08

that meal could get monetized.

46:08

that meal could get monetized.

46:10

And if the waiter or waitress treats me nice,

46:10

And if the waiter or waitress treats me nice,

46:13

they might get they they have they they have better chances of monetizing their behavior.

46:13

they might get they they have they they have better chances of monetizing their behavior.

46:18

Than otherwise.

46:18

Than otherwise.

46:20

So there's lots to learn from how monetization works

46:20

So there's lots to learn from how monetization works

46:23

in the bottom third of

46:23

in the bottom third of

46:25

the economy in other industries. So a waiter

46:25

the economy in other industries. So a waiter

46:29

is the bottom third of the is in the bottom third of people who work in restaurants or involved in the restaurant industry. So how do they monetize

46:29

is the bottom third of the is in the bottom third of people who work in restaurants or involved in the restaurant industry. So how do they monetize

46:36

themselves?

46:36

themselves?

46:38

And there's a lot there's a lot of industries where you can say, hey, the bottom third of this sector or this space or this country. They don't make any money, but but they could maybe. And you could look at that as examples of

46:38

46:51

you know, how do I how do I

46:51

you know, how do I how do I

46:53

lighten up this third by allowing them to collect money This last is gonna be always a huge industry. Square is a great example.

46:53

lighten up this third by allowing them to collect money This last is gonna be always a huge industry. Square is a great example.

47:01

Square took the mom and pop store that couldn't accept credit cards

47:01

Square took the mom and pop store that couldn't accept credit cards

47:05

because no bank would trust them and Square enabled them to accept credit cards. So Square is the only company in the world that does that And they became, I don't know, a twelve billion dollar company because they were able to monetize the bottom third of, you know, mom and pop retail stores.

47:05

47:22

And so that's one model for creating a billion dollar company. And then I might use idea sex to generate the ideas. Like, oh, how does every other industry monetize their bottom third Let's apply it to YouTube and see what happens.

47:22

47:35

You know, and then I'll look at competitors, like, okay. There's Patreon, but you have to Patreon has various hurdles. You you have to already know you're gonna be a good content creator, and you have to come up with awards, and you have to interact, and create content specifically for Patreon. And so, so, Patreon has problems.

47:35

47:50

So I try to look at I hate Patreon. I think Yeah. Like So stupid. If you're a content creator,

47:50

So I try to look at I hate Patreon. I think Yeah. Like So stupid. If you're a content creator,

47:56

Patreon could be a great way to make money, but it's it I find a lot of content creators once they have a big audience find Patreon to be more annoying than helpful. But advertising also is annoying. So,

47:56

48:07

you know, finding advertisers yourself and outsourcing all your advertising to YouTube could also be annoying. So you know, there's various problems in the current ways people monetize. I mean, you guys monetize a newsletter. So subscription's another way, but that puts us, some friction in front of your subscribers.

48:07

48:23

And,

48:23

And,

48:24

so, you know, I've done newsletters. I've done, you know, advertising

48:24

so, you know, I've done newsletters. I've done, you know, advertising

48:27

support in media, like, podcasts or websites.

48:27

support in media, like, podcasts or websites.

48:31

And so I'm familiar with all these types of monetization.

48:31

And so I'm familiar with all these types of monetization.

48:34

And, I don't know, all these things together helped me make my ideal list. What's your favorite wave ways for monetizing content?

48:34

And, I don't know, all these things together helped me make my ideal list. What's your favorite wave ways for monetizing content?

48:44

For me right now, I don't think I've ever

48:44

For me right now, I don't think I've ever

48:48

really

48:48

really

48:49

monetize content

48:49

monetize content

48:51

the way I would like to. Like, subscription

48:51

the way I would like to. Like, subscription

48:53

but okay. So but I'll let me ask you a question. Subscription is the best way to monetize

48:53

but okay. So but I'll let me ask you a question. Subscription is the best way to monetize

48:58

most content.

48:58

most content.

48:59

But, again, you have to plan for that in advance. So you have to say I'm gonna make a subscription

48:59

But, again, you have to plan for that in advance. So you have to say I'm gonna make a subscription

49:04

called the, subscription product called the hustle with with new ideas and trends,

49:04

called the, subscription product called the hustle with with new ideas and trends,

49:09

every week made by my great analysts and people are willing to pay a dollar a month or whatever, ten dollars, whatever it is. And subscription's a great way to monetize because you're not always chasing advertisers.

49:09

49:19

It's this annuity that comes in and helps you even survive in a recessionary environment or, like, right now. So I love I think subscription

49:19

It's this annuity that comes in and helps you even survive in a recessionary environment or, like, right now. So I love I think subscription

49:28

is a whether it's an online newsletter or an online course or

49:28

is a whether it's an online newsletter or an online course or

49:33

subscription community, like, you know, let's say the trends Facebook community. I think subscription's my favorite way to monetize but it doesn't solve the problem of monetizing

49:33

subscription community, like, you know, let's say the trends Facebook community. I think subscription's my favorite way to monetize but it doesn't solve the problem of monetizing

49:43

when you're not already in the top one third of content. Like, like, you guys are in by in the top one tenth of one percent of content, you're going to monetize and do very well no matter what model you choose, whereas

49:43

49:55

the the bot someone who writes a newsletter about,

49:55

the the bot someone who writes a newsletter about,

49:58

I don't know,

49:58

I don't know,

50:00

you know,

50:00

you know,

50:02

some obscure

50:02

some obscure

50:04

kind of Taekwondo or whatever, they're not gonna be able to monetize a newsletter necessarily where someone who's gonna monetize how to mow the lawn better is not gonna be able to monetize but might have one piece of content that really stands out.

50:04

50:15

And if you were, you know, I think you're you're pretty much,

50:15

And if you were, you know, I think you're you're pretty much,

50:19

one of the top one percent or or better of people at building

50:19

one of the top one percent or or better of people at building

50:23

new businesses or,

50:23

new businesses or,

50:25

audiences. Right? I think you've you've done an amazing job of building up audiences that will follow you through one medium podcasting,

50:25

audiences. Right? I think you've you've done an amazing job of building up audiences that will follow you through one medium podcasting,

50:31

blogging, email, whatever you want. Let's say you're twenty one years old again today. You know everything you know now, but nobody knows your name.

50:31

blogging, email, whatever you want. Let's say you're twenty one years old again today. You know everything you know now, but nobody knows your name.

50:40

How would you go about building an audience today? Yeah. Today, I well, first off, let's assume I have something to say. You have to have something you have to have a unique perspective. And again, I'll I'll I'll take

50:40

50:51

I'll take the this podcast as an example. It's my first million. It's the name of this podcast. Right? Yep. So there are other podcasts about

50:51

I'll take the this podcast as an example. It's my first million. It's the name of this podcast. Right? Yep. So there are other podcasts about

50:59

There's a there's a podcast. The eventual millionaire, which talks to millionaires about it. But most of these other podcasts

50:59

There's a there's a podcast. The eventual millionaire, which talks to millionaires about it. But most of these other podcasts

51:06

Unlike you, most of them are started by people who haven't yet sold their first business or haven't made that first million. So their unique thing is they're approaching people almost as if they're asking for advice. How can I do it? You did it. How can I do it? So that's a a different your perspective is You've done it, so you're able to morph in a different type of nuance drilled down on that. And you have something unique to bring out of people and and say to people and so on. And and and Sam, for you, you've spent so much time studying

51:06

51:35

trends and side hustles and the gig economy.

51:35

trends and side hustles and the gig economy.

51:37

The hustle is like the best email newsletter out there because it's your your the voice of it is so unique. It's it's the go to, particularly during this lockdown. It's it's amazing

51:37

The hustle is like the best email newsletter out there because it's your your the voice of it is so unique. It's it's the go to particularly during this lockdown. It's it's amazing

51:48

people ask me, Hey, what are some side gigs we could do from home? The first thing I always say is check out the hustle, and you'll get a ton of ideas, even in our podcast, I mean, you're just, like, spitting out ideas that I've I've I've run with and completely stolen from you. So

51:48

people ask me, Hey, what are some side gigs we could do from home? The first thing I always say is check out the hustle and you'll get a ton of ideas, even in our podcast, I mean, you're just, like, spitting out ideas that I've I've I've run with and completely stolen from you. So

52:03

That's the other thing about having good ideas that you could steal them from people. But,

52:03

That's the other thing about having good ideas that you could steal them from people. But,

52:09

you know, I think you have to something you have to have something unique to say. So at the age of twenty two, you question. Well, do I really have something unique to say? And often when I write something, I don't hit publish unless I'm afraid of what people will think about me after I hit publish because otherwise that I'm probably not saying something new or different

52:09

52:27

or, you know, there has to be I have to challenge myself in some way to create unique content. But give it let's assume you have something unique to say or some expertise you built up by the age of twenty two. I would go on Quora

52:27

52:38

and just answer every question I could. I would participate

52:38

and just answer every question I could. I would participate

52:42

on LinkedIn groups again answering every question I could. I would go on,

52:42

on LinkedIn groups again answering every question I could. I would go on,

52:46

groups like the trends group or other Facebook groups. And, you know, a lot of people ask questions. I'll go on Podcast's Paradise, which is a subscription community about podcasting. I would a lot of people say, hey. What you know, how do you get good guests, or how do you what kind of microphone should I use? I would answer every question I could. And establish

52:46

groups like the trends group or other Facebook groups. And, you know, a lot of people ask questions. I'll go on Podcast's Paradise, which is a subscription community about podcasting. I would a lot of people say, hey. What you know, how do you get get good guests, or how do you what kind of microphone should I use? I would answer every question I could. And establish

53:05

expertise.

53:05

expertise.

53:06

And then

53:06

And then

53:07

I would again, I'm thinking if I'm a twenty two year old, I'm not thinking this way now. And then

53:07

I would again, I'm thinking if I'm a twenty two year old, I'm not thinking this way now. And then

53:12

Once I had some expertise, I would branch out. So now I've you just you just saw me. Everywhere you looked, you saw me, Quora, LinkedIn, Facebook, there's there's James again answering questions. Now I'll start going on sites where there's a little bit higher

53:12

Once I had some expertise, I would branch out. So now I've you just you just saw me. Everywhere you looked, you saw me Quora, LinkedIn, Facebook, There's there's James again answering questions. Now I'll start going on sites where there's a little bit higher

53:26

barrier to create content. So, like, a forbes dot com or inc dot com or

53:26

barrier to create content. So, like, a forbes dot com or inc dot com or

53:32

TechCrunch or whatever.

53:32

TechCrunch or whatever.

53:34

And and this is what I did do. And I started would start writing or Yahoo Finance. I'd start writing articles

53:34

And and this is what I did do. And I started would start writing or Yahoo Finance. I'd start writing articles

53:39

for them. So now people see me in a more of a position of authority. So it's not just to have, like, a number of certain number of followers on either quora or Twitter or LinkedIn or whatever. It's like, oh, I I just saw James on quora. Now I see him on c n n dot com.

53:39

53:53

What's he doing there? And so

53:53

What's he doing there? And so

53:56

so I establish an authority,

53:56

so I establish an authority,

53:57

then

53:57

then

53:58

you gotta create an email newsletter that's free ninety nine percent of your content has to be free.

53:58

you gotta create an email newsletter that's free ninety nine percent of your content has to be free.

54:04

So I would create an email newsletter and always just at the end of my articles, I would say, hey. Do you wanna hear more from me? I have an email newsletter. Sign up now, and I'll give you my book the top twenty hustles for twenty twenty. And just for free. And,

54:04

So I would create an email newsletter and always just at the end of my articles, I would say, hey. You wanna hear more from me? I have an email newsletter. Sign up now, and I'll give you my book the top twenty hustles for twenty twenty. And just for free. And,

54:19

you know, just and then I would just start putting all my articles on my free email. And then I'd start at some point, my level of expertise should be big enough that I can start a four pay so subscription newsletter, like, whether it's about trends

54:19

54:32

or stocks or some physical activity or And and this is the exact thing you did. I mean, I think that

54:32

or stocks or some physical activity or And and this is the exact thing you did. I mean, I think that

54:39

from an outside perspective, I mean, it looks like their newsletter business makes tens of millions in subscription revenue.

54:39

from an outside perspective, I mean, it looks like their newsletter business makes tens of millions in subscription revenue.

54:45

Yeah. So so did do that. And again, it wasn't the first business I started. That would have been a good first business. If the question was if I was twenty two, what would I do? That is how I did do that that latest business that I sold,

54:45

54:57

and and it worked. That model works. And I encourage other people start an online course. Like, A friend of mine has an online course that she started.

54:57

and and it worked. That model works. And I encourage other people start an online course. Like, A friend of mine has an online course that she started.

55:05

This person is the most introverted shy person I know, and she started a course on how to be noticed by the media, how to become a media expert.

55:05

This person is the most introverted shy person I know, and she started a course on how to be noticed by the media, how to become a media expert.

55:14

And she priced it at seven hundred dollars. She sell she opens it up for, like, three days every year. Sells another thousand and makes seven hundred thousand a year. And and, you know, lives in a cheap country. She moved there just to keep expenses down. And know, this is a and it was and it's just a course. So it's not an ongoing newsletter.

55:14

And she priced it at seven hundred dollars. She sell she opens it up for, like, three days every year. Sells another thousand

55:21

and makes seven hundred thousand a year. And and, you know, lives in a cheap country. She moved there just to keep expenses down. And know, this is a and it was and it's just a course. So it's not an ongoing newsletter.

55:33

I think an online course is better actually than newsletters.

55:33

I think an online course is better actually than newsletters.

55:37

And I think affiliate deals are better than also creating an online newsletter. So so if I were to redo my business, I would do it over slightly

55:37

And I think affiliate deals are better than also creating an online newsletter. So so if I were to redo my business, I would do it over slightly But,

55:45

But,

55:46

you know, that that's what I would do if I was starting completely from scratch. I think I've seen that methodology work over and over again, and it is the advice I give people because Content creation is is king. Like, that is always there's a demand.

55:46

56:01

How many times have you been asked this during this lockdown? Man, what what shows should I watch? I feel like I've watched everything.

56:01

How many times have you been asked this during this lockdown? Man, what what shows should I watch? I feel like I've watched everything.

56:06

Content people always want more content.

56:06

Content people always want more content.

56:11

All the big content creators spent hundreds of billions on content just on sitcoms this year. So,

56:11

All the big content creators spent hundreds of billions on content just on sitcoms this year. So,

56:17

there's so much demand per per content, and you can provide value. Like, If you really

56:17

there's so much demand per per content, and you can provide value. Like, If you really

56:22

again, ninety nine percent of your content will still be free, that's key. But you could provide extra value that it's worth paying for. Like, For instance, I forget if I get I think I get the hustle for free. Right? Like, that's a free newsletter. Free trends is not. Trends is not. But but the hustle, you convince I love the hustle, and that's where most of your content is. Yeah. But it's it's the quality and the voice in the hustle that convinced me. Okay. I need to get trends, and I'm happy to always pay for it. And it's or I mean, it just We gotcha. We gotcha.

56:22

56:52

Yeah. But but but there's value. Like, if if you don't provide value, then people are gonna realize pretty quickly that you're useless. Like, you always have to provide value and have something and have a unique perspective.

56:52

57:01

Yeah. I think that is the key and the hardest part is having the unique perspective. Everything after that is sort of the textbook.

57:01

Yeah. I think that is the key and the hardest part is having the unique perspective. Everything after that is sort of the textbook.

57:07

You know, you run the playbook after that of how do I get it out there for free? How do I collect of, you know, of a customer relationship, and then how do I monetize

57:07

You know, you run the playbook after that of how do I get it out there for free? How do I collect of, you know, of a customer relationship, and then how do I monetize

57:14

for the most hardcore? But the unique perspective is is hard. How do you shape that?

57:14

for the most hardcore? But the unique perspective is is hard. How do you shape that?

57:19

I'll I'll give you another example. Like, do you guys play Fantasy Sports at all? Yep.

57:19

I'll I'll give you another example. Like, do you guys play Fantasy Sports at all? Yep.

57:22

Okay. So I do not play Fantasy Sports. I knew I I don't even know the roles of football,

57:22

Okay. So I do not play Fantasy Sports. I knew I I don't even know the roles of football,

57:27

but,

57:27

but,

57:30

Matt Berry, who's the Fantasy Sports

57:30

Matt Berry, who's the Fantasy Sports

57:32

anchor at ESPN. He also hosts this TV show, the Fantasy show at ESPN.

57:32

anchor at ESPN. He also hosts this TV show, the Fantasy show at ESPN.

57:37

That guy was a Hollywood screenwriter. He was writing movies and TV shows, and he hated his life, and he quit that. It's making a ton of money. He quit that.

57:37

That guy was a Hollywood screenwriter. He was writing movies and TV shows, and he hated his life, and he quit that. It's making a ton of money. He quit that.

57:47

Started writing blog. He just loves sports and fantasy sports. He started blogging about that for a hundred dollars a blog post. Just kinda broke after all this and quitting Hollywood, moved away. And

57:47

57:59

a hundred dollars of blog posts was the most he can get because he had this writing scale from his Hollywood times,

57:59

a hundred dollars of blog posts was the most he can get because he had this writing scale from his Hollywood times,

58:05

he's he had a he quickly got a huge audience in Fantasy Sports. Then he built a four pay subscription site. And, you know, after producing most of this content for free, ESPN bought it, and he kept moving up the ranks there and boom. He's he's done so much better

58:05

58:21

doing what he loves

58:21

doing what he loves

58:23

at fantasy sports and monetizing in almost the same way I just described. And he's so much happier than when he was writing movies, which is a lot of people consider the dream job.

58:23

at fantasy sports and monetizing in almost the same way I just described. And he's so much happier than when he was writing movies, which is a lot of people consider the dream job.

58:33

I love it.

58:33

I love it.

58:35

We should we should wrap up in a second. James, this was awesome. I I gotta admit you were way more legit than I, expected. You know, I thought you were What? Did you expect me not to be legit? Well, he I've already I already called him out on this, which last time or he called himself out. He goes, so when his company was acquired, Sean,

58:35

58:52

James is like, Dude, my content's legit. I'm legit. I do it all, but the acquiring company admittedly is incredibly aggressive with the advertising. And sometimes that, kinda makes me appear as though I'm one thing when I'm not. Yeah. And and and and by the way, it's it's a very interesting topic. How aggressive you should be with your advertising

58:52

59:09

And there so Alain Debiton, who's this French philosopher,

59:09

And there so Alain Debiton, who's this French philosopher,

59:13

he has this theory that even the good guys need to use Machiavellian

59:13

he has this theory that even the good guys need to use Machiavellian

59:18

tactics.

59:18

tactics.

59:19

They need to use the because otherwise,

59:19

They need to use the because otherwise,

59:21

if I just said, hey, guys, I have a unique perspective on Bitcoin. Please listen to me.

59:21

if I just said, hey, guys, I have a unique perspective on Bitcoin. Please listen to me.

59:26

There was so much aggressive advertising out there that they would have drowned me out. And I would have not succeeded in my mission, which was to inform people what I thought was a correct view of Bitcoin.

59:26

59:37

And then what would have been the point? Right. So sometimes

59:37

And then what would have been the point? Right. So sometimes

59:41

And But but it did it did cost me though. Like, doing because my ads were so good,

59:41

And But but it did it did cost me though. Like, doing because my ads were so good,

59:47

we dominated. I mean, that was the reason Facebook, Google, and every place shut down. Crypto ads is because of my ads. Yeah. The the, you know, that was definitely a little piece of it, but what I actually meant was most of the time when a guest comes on,

59:47

59:59

I think to myself, well, this is a really successful person, but man, they're they're, you know, they don't tell a great a great story. You know, they they do not bring know, sort of energy stories, and also, you know, some unique,

59:59

01:00:11

insights of the audio, you know, I'm imagining

01:00:11

insights of the audio, you know, I'm imagining

01:00:13

I'm a listener, right? Like, during this interview, you talked for most of us. I was actually, you know, listener number one for this podcast episode, and I would have liked this one. And so I I can't always say that that's the case with all of our guests. But you brought that. That's all I really meant when you're legit, which is, you know, you raised the bar for the podcast, which was great. Excellent. Thank you so much.

01:00:13

01:00:33

So, James, this was awesome. If people wanna say hi to you, is Twitter your your go to method? No.

01:00:33

So, James, this was awesome. If people wanna say hi to you, is Twitter your your go to method? No.

01:00:39

I'm James Alcatcher on TikTok.

01:00:39

I'm James Alcatcher on TikTok.

01:00:42

Oh my gosh. Nice. That's where that's where you could find my absolute best content now. It's TikTok. No one wants to see a fifty year old dude dancing to Brianna.

01:00:42

Oh my gosh. Nice. That's where that's where you could find my absolute best content now. It's TikTok. No one wants to see a fifty year old dude dancing to Brianna.

01:00:51

No. I'm not dancing.

01:00:51

No. I'm not dancing.

01:00:54

I did do one one time. I danced, and someone said,

01:00:54

I did do one one time. I danced, and someone said,

01:00:58

someone literally said, commented,

01:00:58

someone literally said, commented,

01:01:00

dude, this is not why we follow you. Stop this. Yeah. And so I took that one down and I haven't danced since. Although,

01:01:00

dude, this is not why we follow you. Stop this. Yeah. And so I took that one down and I haven't danced since. Although,

01:01:07

If if push came to shove and I was drunk, I when I was twelve years old, I was a semi professional break dancer, but that was a long time ago. The comedian Bitcoin

01:01:07

If if push came to shove and I was drunk, I when I was twelve years old, I was a semi professional break dancer, but that was a long time ago. The comedian

01:01:15

Bitcoin

01:01:16

break dance there.

01:01:16

break dance there.

01:01:18

Well, that's not ass, man. We appreciate you coming. I, I'm looking forward to joining you again and you coming back to us and and developing a friendship. That's them. Excellent. Yeah. And and and Sean. Yeah. Definitely, let's have you on the podcast as well. So I'll I'll I'll Cool. I'll let you go ahead. Change emails, and we'll figure it all out. Sounds good. Thank you. Alright. Alright. You guys. Thanks a lot. Talk to you soon. Bye. Bye.

01:01:18

00:00 01:01:47