Entrepreneur Who Lost Millions Breaks Down How To Come Back Financially | My First Million 5/18/2020

So the background here, by the way, Sean, is I was on James's show, um, 3 weeks ago. It actually aired today. I've been getting people reach out, reaching out to me. James, uh, 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—

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

I know about you. Yeah, I know about him. I've read a bunch of your stuff and I was like, this guy's the shit. And then 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 sells the latest thing? Like, oh, here's the new thing. Cool. I'll shill that. And I was like, oh, okay. I don't know how I feel about this. And then I read some of your stories 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, uh, if Tim Ferriss, you know, smoked a bunch of weed and was on the internet. I don't know, like, it was just like some, some variation of really interesting guy who po— you know, who's built his brand on the internet. 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, it's like you always have sort of unexpected things. That's what I have sort of come to like about you. But, you know, that's my admittedly very loose, uh, knowledge about, about you.

Do you wanna give some background?

Yeah. I mean, it's kind of like what you were both sort of referring to. I've, I've had for better or for worse, uh, 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, I sold something for a billion and I ended up with $10 million. This is horrible. No, I would sell something for millions and then end up with zero or less than zero in my bank account. Really just zero, actually. I wish 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. Oh, I owe you $10 million. Let's work it out. And you maybe give me some so I could build the— I don't know what it is, but like, I think it was a young man in the '90s named Donald Trump who said, if you owe $2 million to the bank, the bank owns you. But if you owe $2 billion to the bank, you own the bank. And, but anyway, I would often end up at $0 and be depressed. 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. And so I had nowhere to go and, and no idea and, and depressed. And I didn't know how to, in some cases, 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? Uh, how to be creative in 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. I started, I combined those two things and I started a company in the '90s making websites for entertainment companies. And then I became a venture capitalist. Then I started a hedge fund. I wrote some software to helped me invest in that. And then I started writing books about that. So I became a writer, then I became a podcaster. And then like you were saying, I started writing about much more personal stuff. And I think everybody who knew me couldn't believe it. Like it was almost like they had never seen anything like this before. Like why? They, people will call me up like, James, are you, uh, 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. I'm not going to do a deal with you again, or this is too embarrassing. And I, you know, and then I think since then people have, I don't want to say people copied it. People had their own versions of writing about failure 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, my audience was bigger than ever. Previously I'd written about finance. Now I was writing about all this personal stuff. My audience became 100 times bigger, and then I started getting more investment opportunities. I started getting a podcast, which became successful. I just started getting many more opportunities because of, because essentially I paid with my vulnerability for freedom, and that created a whole kind of career for me. And it wasn't intentional. I just was sick of writing about all the BS stuff I kept seeing everyone else write about. And if you want to, if you want to be unique, you kind of have to say what's unique to you. And what was unique to me was all the times I was scared to death and depressed and had to fight my way out of it. So on many things, to answer the question, I have 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 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 were you making money and how were 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 3 hits.

Yeah. I would say it's more like 5 or 6 hits again, for better or for worse, I needed all 5 or 6, but, um, the first one, again, I was working at HBO and I made their website. Uh, and at the, at the time, other entertainment companies and other companies, they didn't even know what this internet web thing was. This was in 1995. And companies like American Express, American— here's what would happen. American Express would call Arthur Andersen, which was their accounting firm. And, you know, Arthur Andersen famously went outta business, uh, in, in a scandal 6 years later. But American Express called Arthur Andersen, said, can you make us a website? Arthur Andersen said, sure, we're gonna charge you millions of dollars. Arthur Andersen would then call another software consulting company and they would say, yeah, we'll charge you $1 million. The software company would call me 'cause nobody knew how to make a website in 1994 or 1995. So I would say, sure, I'll do it. And then suddenly they'd pay me and my brother-in-law $250,000 to make americanexpress.com. So that was one of our first websites. And I, my salary at HBO at the time was $40,000 a year. So my brother-in-law and I, we made HBO.com. Then we made websites for everything from Warner Brothers, Sony, Disney, BMG, all the record labels. Like we did every gangster rap record label, Bad Boy, Loud Records, Jive, Death Row, Interscope. Uh, we did the movies for The Matrix, uh, 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?

Well, you know what? That's a great question. So no, it doesn't look like Craigslist. I wish it did. But, uh, design, web design back in those days. So I was a software guy. My brother-in-law was a design guy. Web design back in those days was very heavy. So there would be like big heavy images and animations using Flash or Yep. You know, some Mac, I forget the company, Macro something. And, uh, uh, they were, they were very heavy designs, not that usable. And, but yeah, I mean, they were okay. They, they were admired back then. So the website for The Matrix was a great website, which, you know, on, on archive.org you could find, or HBO's website was a great website, but it, 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?

Uh, about, uh, $15 million. And then cash.

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 1999, I cashed out and I had the cash in my checking account. Like I didn't even want to—

What do you mean cash out? Were you getting like— stock in these companies? I mean, I understand.

Yeah. So, so no, no, I sold the company to a company that was rolling up web design 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 1998 and acquired us. And so suddenly they were an internet company and the stock went from 3 to 48. And I cashed out with literally at the peak with about A little over $15 million, almost $16 million cash. And, and here I was, I was smart every step of the way. Like I knew that the web design development business industry was going away because they were teaching web, you know, how to make a website in junior high school classes. So I knew this was going away. I was smart. I sold the business. I cashed out as fast as I could. And then I became everybody, you You suddenly, 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, what should we invest in?" Or, "You know this internet thing. You have curly hair and glasses. You must know all this internet stuff. You look like a technology guy. What should we invest in?" So I started thinking, "Oh, I must be really smart at this." And literally, poured all this cash back into internet investments after I had cashed out of the internet. And it really went— 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 gambling every single day. Like I was playing poker for 365 straight days. I played poker at least 8 to 10 hours a day.

I was going to ask you if you're a degenerate gambler because you kind of have that. I mean, you sound like that before you even told me you were 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 the poker boom took off when I decided, you know what, I'm just going to focus on starting new companies and internet investing. And I stopped playing poker like in, you You know, right at the end of 1999, I started a venture capital firm and I just started investing money.

And was your firm all your money? So your firm?

No, no, we raised, we raised $200 million. Like, holy fuck. That was the other thing too. I didn't have any experience doing any of this stuff. I didn't know anything. Um, I, I, I'm trying to remember all investors. Uh, CS First Boston, Deutsche Bank, like all these major banks gave us money. And then another company, Investcorp. Uh, which is a major private equity firm, uh, gave us $100 million. And, and then I started investing my own personal money side by side with the fund and in other investments. And I started buying stocks all the way down.

So how long till it went to zero? From $15 million to zero, how long was that?

Um, I was losing about $1 million a week in the summer of 2000. And, 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. 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, you know, how to— I really didn't understand anything then about investing. Like, I was an idiot. And I went to zero by right around mid-2001. 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 2 blocks, 3 blocks from a little building called the World Trade Center, and we were getting an offer on September 11th. And of course, many worse things happened that day than me not getting an offer for my house. But 9/11 happened and we couldn't sell then because we were part of the crime scene. And, you know, just, I went totally, totally broke.

Were you home in that?

I was at the World Trade Center.

Oh my God.

Which I don't really, I don't really talk about because A, it sounds unbelievable, but B, it also, many worse things happened to people, to many more people than me that day, obviously. But my business partner and I, there was a Dean and DeLuca on the first floor of the World Trade Center. We ate breakfast there every day and then we would day trade the markets. And at that point, I was starting to come back a little bit from day trading and I had written some software and, and so on. And then we're walking 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 on TV, but like physically we saw it go right into the building. And everybody on the street instinctively ducked and, and your, your brain does weird things. So my, I started thinking to myself, like my, my business partner's name's Dan. He said, we're, we, 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. Like my brain was telling me this even though it was a quarter to 9:00 AM. And you know, how do you remote control a, a, whatever it was, a 747? Into the World Trade Center, but that's what my brain was telling me. So we run to the fire station and we say, we want to help. And these guys throw two fireman suits at us and say, get this on, we're going to go straight over there. And 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. And that fire station, it was the Duane Street fire station. 100% of those people died who went to the World Trade Center that morning. And then from, you know, it was 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 kind of went to zero after that. And then I was just, Desperate for like a year and a half. Couldn't sell the place. Couldn't, you know, there were no jobs. I was an idiot. Nobody would, I had no friends anymore. And, you know, I had to teach myself how to invest. So I wrote some software where I took every piece of data about every single stock since World War II and looked for patterns. You know, when would I would have my software find statistically significant patterns where trades were good. So I would try to model, let's say, fear and greed in the markets. And it worked pretty well. It 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 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 learning about investing. This gave me time to actually learn the skill and talk to people who were experts and professionals and really learn. Then I started writing about investing and I started going on CNBC and I started a hedge fund and I started, 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 investing and going on CNBC. And then I built, so I was doing deals also then and making money. And then I built a website that combined my interests in web development with investing. I made like a social, I called it the MySpace of finance because MySpace was big then. And sold that site. And that was like my next big hit, sold that for $10 million. And, you know, and then a year later I was broke again. And that's the things like that just kept happening.

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There's a lot going on here, but you've sold 2 companies so far. Well, you've also sold your newsletter business too, right?

Yeah. So, so that was the third company. And I've also sold companies that I was, um, either, um, I've, I, there's many companies I've been an investor of that have been sold by this point. Um, and then some companies that I'm like a, a co-founder of that I've, that I've sold. I was like involved, I've been involved with everything from like a, a mental rehab facility that sold for $41 million. And then that was in 2004. I did go broke after that. And then was Stock Picker, the stock site. And then I was an early investor in Buddy Media.

Yeah.

Which Peter Thiel invested in. Mike Lazarow was the CEO. Mark Pincus, who started Zynga, was an investor in it. And we all were the seed investors at a $4 million valuation that sold to Salesforce for about 700 or 800 million. I had a company today that I was an investor in that just, it just kind of did a rev— or they just announced a reverse merger. They're going public. So hopefully that will do well, but I've been, I've been an investor in a lot of companies that have done well. Cause like, cause I finally figured out the most important thing about investing that I missed before. And that since then my private investing has done very well and I don't really do public investing.

Well, what's that thing?

That one thing is that I am 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. Take Buddy Media as an example. I didn't have to do any work once I invested because Peter Thiel was my co-investor. 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 would know what he was doing when investing in a Facebook marketing agency, which is what Buddy Media was. So, so I always. 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, all the hard work. He's got PhDs working for him that are a lot smarter than me. If worse comes to worse, he or she can make phone calls and get this company acquired, which is what happens. And 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 100%. It's not like a normal success rate. It's like 100% success rate when you do that. And the other rule is if they ever call me for advice, 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 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 companies ranging from oil companies to tech to law enforcement to the company today is an erectile dysfunction drug. I don't, I don't know anything about biotech, like the, but as long as someone, you know, if, if someone calls me and says, look, hey, I've, I've started the last 3 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, um, I think Sean's gonna want to ask you questions on angel investing and I want to ask some, and I want to hear his answer or your answers to those questions. But before we get to that, what about selling? I mean, so you've sold, uh, more than a handful of businesses. Selling companies is hard. Most people will never sell one. How are you? Yeah. What, how are you able to, uh, sell so many, you think?

Like, you know, 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?

Uh, I had a small, like hundreds of thousands of dollars sale, um, for this company, uh, The Hustle. We had term sheets and I walked away at the last minute. I've had 2 or 3 term sheets and I've walked away from them and I've never closed the deal.

Uh, yes.

So, and then I bought— I've also helped buy companies too.

Yeah. So it was a similar, it's similar skills on both sides of, of, uh, but maybe slightly different. But people don't realize selling a company is very difficult. Like it's, there's 3 skills. There's starting a company, there's building it, and there's selling it.

And Sean sold his company too, to Twitch.

Yeah.

Last year. Okay. 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 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. And, uh, 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, and then there's suddenly 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 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 you know, you don't want her to figure this out too fast and you know, before she really falls in love and, uh, you know, and all that dopamine 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 gonna jeopardize this deal either because I'm gonna push too hard just cuz I'm impatient or I'm gonna go start another business, which is the worst thing I can 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, uh, it's, it's, it's a painful process. And the way you sell is, first off, you have to, and this is not, you have to be sincere the whole way through. You have to have a vision. That matches their vision very strongly. And it has to explain why you would— if this, your business is so great, why do you want to sell it? Like there's that inherent contradiction in selling a business. And 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 partner. And now maybe I would limit my upside, but you know, the first time you sell a company for millions and then the second time, If you're broke the second time you sell a company for millions, and then the third time, it's okay to not sell for billions because you want to get that initial chunk. But you also have to say, look, together, here's how it's 1 1 3. And you have to be really persuasive on, on why 1 1 3, even for you personally. Like you have to be able to express that this vision is gonna benefit you personally if you partner with this other company. And, and, 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. 'Cause usually there's some backend earnout 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. Which negotiating is one of those things that 9 out of 10 people think that they're above average, which is impossible. Like you have to be 4 out of 10 only could be above the median and only 1 out of 10 is really good enough to sell a company properly. And so I had to learn the hard way how to negotiate. 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 because you don't want to sound greedy and you don't want to sound desperate and you don't want to sound, and you don't want to underprice yourself. So there's all sorts of negotiating techniques that you have to use to, to help them answer that question in a way that works for both sides, not just for you, but for both sides.

Did you value your companies on a multiple of your profit or revenue, or was it, uh, 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 there's, there's 3 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 in an industry that trades on the stock market for 20 times earnings, then your company is probably your last year's profits times 10, the 20 divided by 2. Uh, 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 learn this from my fir— my first company was profitable, unlike every other internet company. And so we sold for about 10 times earnings, which was a mistake. The second company was like, I did value it like how you said, which is if you, 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. The challenge there is with the other company, you work out this formula for how you're going to value your company based on their, their, them helping you build your earnings. And the challenge is then you fill in all the variables. They know the variables better than you. So you have to make sure when you're negotiating the formula, 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. And then the third way to value things is you 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 companies often, particularly in the tech sector, like Giphy. I don't know what they, how they value themselves, but certainly wasn't off of earnings. I don't think they had $20 million in earnings. My guess is they were losing money. So, uh, so they probably valued off of something, some kind of comparable deal in, in the internet.

Yeah. Cause, and then Tenor sold, Tenor, which was Giphy's competitor, just sold to Google a year before for a little less than that.

Oh, well, who was their competitor?

Uh, a company called Tenor, T-E-N-O-R.

They were, and, and.

Their competitor. Yeah.

It just says aside, is it true that Giphy was the second largest search engine in the world? That's what they're saying.

Yeah.

They, they love to say that. Yeah.

They love to say that.

I thought YouTube was.

Yeah. So YouTube is number 2 and Amazon would be Bing is 3, Amazon's 4, right? Like, so yeah, depends what you call a search engine.

But I, I did interview the founder in New York and, uh, it is huge. It was just, um, there was no way to make money off of it really.

Yeah, I had that issue. I was a, I was a, a seed investor and on the board of Bitly. So Bitly had about 5% 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 private equity firm bought it, but it was like a, a 2 or 3x, 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 claw back, you make money again doing something else. You lose it again. I mean, obvious question, at some point were you like, okay, rainy day fund, $2 million is going into this account, and hey, I lost the, I lost the keys, uh, just so you know, like just to stash some money away? What?

Yeah, surely your wife was like, come on, man.

Yeah, how did you get away with not just saving some amount of money?

I, I got divorced. All right, there you go, good answer. That was a problem. And I lost the second house that I bought, and, um Uh, no, 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? And there were things in common, which is just that I kind of, I kind of would just give up after I made a lot of money. I would kind of say, phew, 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. You know, I don't need to have any kind of sense of spirituality. 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. And so I just made it a very concentrated effort. And it sounds sort of cliché and almost self-help, helpy a little bit, but I really would make a concerted effort to keep myself physically healthy. Uh, to have only good people in my life and quickly eliminate any toxic people, like, like the speed of light, no second chances. And creatively, I, I just started writing down every single day, 10 ideas a day. Like, uh, 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. And literally, like, I'm not trying to sell anything here. Like literally within months of writing 10 ideas a day down, it felt as if my whole brain was rewired and I would just, I would bounce back so quickly with ideas. It was just nonstop. And then the aspect of sometimes I would write ideas, uh, for, for other companies and I would send them these ideas if I felt they were pretty good. And, you know, I would always get new opportunities because of that. Like I would visit Facebook, Amazon, LinkedIn, Google, Quora, Airbnb, and just, just the, this one process of writing 10 ideas a day down for the past 12 years has been such an incredible 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 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 for unscripted ideas that would cater to 9-year-olds. So I wrote my list of 10 ideas the next day and I sent it to him. He forwarded it to the I don't know how, like he forwarded it to the head of reality programming at Disney. And right after this, I'm meeting, they got excited. Right after this, I'm meeting, uh, with Disney to go over the ideas.

That's wild. What was there, um, 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 $0 to $10,000 to $100,000 to to like $1 million to $15 million? Like what was the difference in hap— 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, um, I had $0 in the bank and I was living in a studio in Astoria, Queens, which is, you know, was not in the ni— early '90s was not a nice part of Queens. Before that, I had a roommate in a, in an apartment smaller than the room you're seeing me in, and I was paying $300 a month. I was working at HBO for $40,000 a year. I was, I had a suit in a garbage bag that I would pull out every day and put on the same suit 7 days in a row and walk over to HBO. And then we did the very first site I did was this diamond dealer. And, uh, he gave me $17,500 in cash. This is 1994. And I had, I had never had seen any money like this before. $17,500. Like, it almost was like, I couldn't believe this was actually happening. And I walked over to the Chelsea Hotel on 23rd Street, 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 $17,500 and said, could 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. And I felt like part of something. I felt like part of a scene. I felt magical. And that was an amazing moment. And then when I sold that first business, I felt good, 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 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 just more escapist then. And then when I started losing, and every time I've lost, every single time I've lost everything, I was suicidal. And in part for practical reasons, I thought maybe my kids could live off my life insurance. And particularly that first time they were babies, so I figured They wouldn't remember me, but they'll definitely remember the life insurance. So, uh, fortunately I, I, I couldn't figure out how to do it in such a way as to not hurt myself, and I never did it. And, you know, I was very depressed though for long periods of time, but each time the period of depression would get, uh, faster and faster.

And, you know, I, 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, figure out what works for me, right? Like, cool, if I 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 to manage my own psychology. Do you have a sort of any things that you've worked on or you figured out that help you either, you know, boost up gratitude or like, you know, get outta that depression funk? What works for you? Or, or do you, are you conscious about that?

Yeah, very, very much so. And that was part of this 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, you know, uh, I'm not used to working out or, I mean, I'm 52 years old. I've gotta stay as healthy as possible. And so eat every day. I have to make sure I'm eating well, sleeping 8 hours and, and moving. And now with this pandemic lockdown is I have to go outside and make sure I'm, have some outside time. And then emotional health, just what— how much 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 10 ideas a day down? Because creativity, not only is it rewiring your brain to be more creative, you know, or that muscle atrophies, but it also triggers a lot of dopamine when you're creative. And it just If I do it in the morning to work on my 10 ideas a day list, I've got this surge of dopamine that carries me at least till like 1 or 2 in the afternoon. And then spiritual health is just, am I trying to control things I can't control? So that's a very important part of spiritual health. So you see people on Twitter all day long, oh man, they should open, we need to open up this economy right now, or we need to lock down all the people who open up, like on both sides, they're trying to control things they can't control. And they're all day long, they're 24 hours a day on Twitter. And 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 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 4 things, physical, emotional, creative, spiritual, just those 4 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, you know, contentment and wellbeing are much more important than happiness. Happiness is very, as the cliché goes, is very fleeting, but wellbeing, you build a real foundation of wellbeing and that sticks with you.

So what's your business now, James, that you're like, what's like your job now?

Well, I do lots of things. So I mean, I write every day and I just finished a book that will be published by HarperCollins in a year. I do a podcast. I'm still involved in my newsletter business, which I sold. I'm a private investor in about 2 dozen private companies. So I'm, but I'm, remember, I'm not active in those 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. And, um, and a lot of my time the past 5 years until this lockdown has been on stand-up comedy, which makes, you know, which makes minimal at best.

So then did, did your nut for your angel money, that came from like your initial sale?

Uh, 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? Um, which is a risky illiquid thing.

I'm very much now, and this is, this was the key point 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. 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 them, I outsource 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 1 to 2% of my net worth is the maximum I will ever invest in any company. Right now, I'll let the, 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 good private companies don't exit because that means they're growing still at like 50 to 200% 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? Um, which, which company?

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 2009, which are still doubling every year. But they, they're, they're still private. Uh, but that Buddy Media one, you know, $4 million to $700 million was pretty good. Ticketfly was another one I invested in, which, um, I was in the seed round of that and it sold for $450 million. Uh, I invested in another one, which is public now. It's a law enforcement company. They have a, a gun that if they, We, I was sort of a co-founder of this. It started in the living room I was staying at and 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 and the more you try to struggle to get out of it, it squeezes tighter. And so like, like a Batman thing.

Yeah, that was gonna say straight outta Batman. Yeah.

And even the, the one of the founders of TASER is the president of the company now. He, he became the president of the company about a year ago, and we went public. Uh, uh, 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, uh, that, that's been— I'm not exited actually. I'm, I own the shares of the public company. I'm not planning on exit, hopefully ever, because it's, it's— what's the name of the competition? Uh, the company's called Wrap Technologies. I'm not trying to push the stock or anything, so I don't want to even mention that.

Sure.

The stock, stock symbol. But, um, it's, it's, it's just such a great thing to invest in and be a part of the founding of something that literally saves lives every single day.

So, so can you, um, can you, do you have the journal with you that you write your 10 ideas?

Can we, can we get a random day? Let's, uh, let's talk about some ideas. Like what, what do you, what's interesting to you right now, James?

A lot of times it's in my email. Oh, there's my pad. I do it all in waiter's 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 a, 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, uh, what do you have your eye on now?

Yeah, I have no problem even saying what I'm scheming at because, uh, so I've, I, I haven't considered starting a, a co— new company in a very long time, but I have been considering it now. And one of the ideas is I feel It's a shame that content is not monetized unless you're like the top, in the top 1/10 of 1% of content creators. So you have to be like, you know, Logan Paul to monetize your YouTube channel and the other 20 billion people on YouTube, even if they have one video that goes viral, they can't monetize it. So, or, or like even if you have a, if you have a tweet that 20 million people see, but you have only 300 followers. You can't monetize it. So I've been figuring out a way to use these ecosystems to allow people to monetize content. So that's one idea I'm working on, actually physically working on it. And another one involves making a derivative of a board game that I like. But in general, I don't come up with business ideas. I come up with, like I said the other day, I had this challenge of, Oh, I'm gonna challenge myself to come up with TV show ideas that 9-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, like the next idea, I'll write a list of chapter titles. And again, most of the ideas are supposed to be bad because you can't come up with 3,650 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, uh, one idea list that is particularly hard is, and this is the one I wrote this morning, is 10 good positive things that have happened to me personally because of this lockdown. Those aren't actionable ideas, but it was actually hard to come up with 10. Like 1 through 7 is always usually pretty easy, but 8, 9, 10 is usually makes my, I feel like my brain sweating. And, uh, uh, 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? So you can't say the obvious ones, like obviously, you know, video communications technology is gonna be, uh, uh, uh, uh, attractive businesses after this. Instead, I would think, what are the 10 ways I can improve Zoom on Zoom, which was the, is the most popular one right now. So that will be how I exercise the idea muscle around Zoom.

And for your content idea, is there a comp out there? Like, is there somewhere something out there that you 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.

Uh, yeah, so sort of. So I'll do something what I'll call, uh, what I call idea sex. So I'll take ideas from two completely different industries. And again, I've been, a professional in many different industries, uh, again, fortunately or unfortunately, and I'll combine ideas to see if after idea sex there's a little idea baby that could work in, in what I'm doing. So for instance, if I go to a restaurant and have a pretty good meal, that meal could get monetized. And if the waiter or waitress treats me nice, they might get— they have, they, they have better chances of monetizing their behavior than otherwise. So there's lots to learn from how monetization works in the bottom third of the economy in other industries. So a waiter 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 themselves? 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 they could maybe. And you could look at that as examples of, you know, how do I lighten up this third by allowing them to collect money? That's gonna be always a huge industry. Square is a great example. Square took the mom-and-pop store that couldn't accept credit cards because no bank would trust them, and Square enabled them to accept credit cards. So Square's the only company in the world that does that, and they became, I don't know, a $12 billion company because they were able to monetize the bottom third of, you know, mom-and-pop retail stores. And so that's one model for creating a billion-dollar company. And then I might use IdeaSecs 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. 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. So I try to look at, I hate Patreon.

I think Patreon is so stupid.

If you're a content creator, 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, uh, 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, uh, some friction in front of your subscribers. And, uh, so, you know, I've done newsletters, I've done, you know, advertising support and media like, uh, podcasts or websites. And so I'm familiar with all these types of monetization and I don't know, all these things together help me make my idea list.

What's your favorite way, ways for monetizing content?

Uh, for me right now, I don't think I've ever really monetized content the way I would like to, like subscription, but okay. So, but let me answer your question. Subscription is the best way. To monetize most content. But again, you have to plan for that in advance. So you have to say, I'm gonna make a subscription called the, a subscription product called The Hustle with, with new ideas and trends, uh, every week made by my great analysts. And people are willing to pay a dollar a month or whatever, $10, whatever it is. And subscription's a great way to monetize because you're not always chasing advertisers. 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 is a, whether it's an online newsletter or an online course or a, a 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 when you're not already in the top 1/3 of content. Like, like you guys are in by, in the top 1/10 of 1% of content. You're going to monetize and do very well no matter what model you choose. Whereas the, the bo— someone who writes a newsletter about, I don't know, uh, you know, some obscure kind of taekwondo or whatever, they're not gonna be able to monetize a newsletter necessarily. Or 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.

And if you were, you know, I think your, your pretty much, uh, one of the top 1% or better of people at building new businesses or, uh, audiences, right? I think you've done an amazing job of building up audiences that will follow you through one medium, podcasting, blogging, email, whatever you want. Let's say you're 21 years old again today. You know everything you know now, but nobody knows your name. Um, how would you go about building an audience today?

Yeah, today I will— 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, 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, um, there's a, there's a podcast, The Eventual Millionaire, which talks to millionaires about it. But most of these other podcasts, 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 different— your perspective is you've done it, so you're able to more in a different type of nuance drill 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 trends and side hustles and the gig economy. 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. 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 on our podcast, Sam, you're just like spitting out ideas that I've, I've, I've run with and completely stolen from you. So that's the other thing about having good ideas is you could steal them from people. But, um, uh, uh, you know, I think you have to something, you have to have something unique to say. So at the age of 22, you have to 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 then I'm probably not saying something new or different. 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 22. I would go on Quora and just answer every question I could. I would participate on LinkedIn groups, again, answering every question I could. I would go on groups like the Trends Group or other Facebook groups. And you know, a lot of people ask questions. I would go on Podcasters 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 expertise. And then I would, again, I'm thinking if I'm a 22-year-old, I'm not thinking this way now. And then 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 barrier to create content. So like a forbes.com or. Inc.com or TechCrunch or whatever. And this is what I did do. And I started, would start writing, or Yahoo Finance, I'd start writing articles for them. So now people see me in a more of a position of authority. So it's not just I have like a number of certain number of followers on either Quora or Twitter or LinkedIn or whatever. It's like, oh, I just saw James on Quora. Now I see him on cnn.com. What's he doing there? And so I established some authority. Then you gotta create an email newsletter that's free. 99% of your content has to be free. 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 20 Hustles for 2020, and just for free. And, 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 for-pay subscription newsletter. Like whether it's about trends or stocks or some physical activity or—

and, and this is the exact thing you did. I mean, I think that, um, from an outside perspective, I mean, it looks like your newsletter business makes tens of millions in subscription revenue.

Yeah. So, so I did do that. And again, it wasn't the first business I started. That would've been a good first business. If the question was, if I was 22, what would I do? That is how I did do that, that latest business that I sold. Um, 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. 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. And she priced it at $700. She sells, she opens it up for like 3 days every year, sells another 1,000 and makes $700,000 a year. And, and, you know, lives in a cheap country. She moved there just to keep expenses down. And, you know, this is a, and it was, and it's just a course, so it's not an ongoing newsletter. I think an online course is better actually than newsletters. 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, uh, 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. How many times have you been asked this during this lockdown? Man, what, what show should I watch? I feel like I've watched everything. Content— people always want more content. All the big content creators spent hundreds of billions on content just on sitcoms this year. So, uh, there's so much demand for, for content and you can provide value. Like if you really, again, 99% 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. Yeah.

The Hustle's free. Trends is not.

Trends is not, but, but the hustle, you convinced me. I love the hustle and that's where most of your content is, 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 it, I mean, it just launched, but we gotcha.

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.

Yeah, I think that is the key and the hardest part is having the unique perspective. Everything after that is sort of the textbook. Uh, you know, you run the playbook after that of how do I get it out there for free? How do I collect a customer relationship? And then how do I monetize for the most hardcore? But the unique perspective is hard. How do you shape that?

I'll give you another example. Like, do you guys play fantasy sports at all?

Yep.

Okay. So I do not play fantasy sports. I knew, I don't even know the rules of football, but, um, Uh, uh, Matt Barry, who's the fantasy sports anchor at ESPN, he also hosts the TV show, The Fantasy Show at ESPN. That guy was a Hollywood screenwriter. He was writing movies and TV shows and he hated his life and he quit that. He was making a ton of money. He quit that. Uh, uh, started writing blog. He just loved sports and fantasy sports. He started blogging about that for $100 a blog post. Just kind of broke after all this and quitting Hollywood, moved away, and $100 a blog post was the most he can get. But because he had this writing skill from his Hollywood times, he had a, he quickly got a huge audience in fantasy sports. Then he built a for-pay subscription site and, you know, after producing most of his content for free, ESPN bought it and he kept moving up the ranks there and boom, he's got, he's done so much better doing what he loves at fantasy sports and monetizing it 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. I love it.

Uh, we should, we should wrap up in a second. James, this was awesome. I, I gotta admit, you were way more legit than I, uh, expected. You know, I thought you were—

what? Why 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, uh, so when his company was acquired, Sean, James was 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, uh, kind of makes me appear as though I'm one thing when I'm not.

Yeah, and, and, and, and by the way, it's a very interesting topic, uh, how aggressive you should be with your advertising. And there, so Alain de Botton, who's this French philosopher, He has this theory that even the good guys need to use Machiavellian tactics. They need to use the— because otherwise, if I just said, hey guys, I have a unique perspective on Bitcoin, please listen to me, uh, there was so much aggressive advertising out there that they would've drowned me out and I would've not succeeded in my mission, which was to inform people what I thought was a correct view of Bitcoin. And then what would've been the point, right? So sometimes— and but, but it did, it did cost me though, like, doing— because my ads were so good, we dominated. I mean, that was the reason Facebook, Google, and every place shut down crypto ads is because of my ads.

Yeah, 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, um, I think to myself, well, there's a really successful person, but man, they're, they're, you know, they don't tell a great story, you know. They, they do not bring you know, sort of energy stories and also, you know, some unique, uh, insights that the audience— you know, I'm imagining I'm a listener, right? Like, during this interview, you talked for the most of us. I was actually, you know, listener number 1 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 is great.

Excellent. Thank you so much.

So, uh, James, this was awesome. If people want to say hi to you, is Twitter your, your go-to method?

No, um, I'm James Altucher on TikTok. Oh my gosh, that's where, that's where you could find my absolute best content now is TikTok.

No one wants to see a 50-year-old dude dancing to Rihanna.

No, it's his unique perspective.

Oh yeah, I'm not dancing. I did do one, one time I danced and someone said, someone literally said, commented, dude, this is not why we follow you.

Stop this.

And so I took that one down and I haven't danced since. Although, if push came to shove and I was drunk, when I was 12 years old, I was a semi-professional breakdancer, but that was a long time ago.

Oh, really? Got it. A comedian Bitcoin breakdancer. Well, that's badass, man. We appreciate you coming. I'm looking forward to joining you again and you coming back to us and developing a friendship. That's awesome.

Excellent. Yeah. And Sean, yeah, definitely let's have you on the podcast as well. So I'll— Cool. I'll email you. Let's exchange emails and we'll figure it all out.

Sounds good.

Thank you.

All right, all right, you guys, thanks a lot. Talk to you soon.

Bye.