Leap Academy with Ilana Golan - James Altucher: Finding the Freedom to Start Over

Episode Date: June 11, 2024

After selling his first company, James Altucher went from having $15 million in his checking account to a balance of $143 within a short period. Then, he managed to build himself back up and sell another company only to lose it all again. Although he failed many more times, James never let fear stop him from taking action. His commitment to consistent experimentation led him to make several bold leaps, from web development to business, and from finance to standup comedy. In this episode, James and Ilana talk about how he is able to master new skills and reinvent himself quickly despite the fear of failure.  James Altucher is a bestselling author, serial entrepreneur, LinkedIn influencer, and venture capitalist. He has written over 20 books, including his most recent, Skip the Line.   In this episode, Ilana and James will discuss: - How he lost his fortune twice  - Lessons he learned from hitting rock bottom - The ‘10 ideas a day’ practice that changed his approach to life and business - The four areas he focused on to get himself out of a rut - Taking action in spite of fear - Execution as a subset of ideas - Hacking mastery by becoming the best at intersections - Having freedom no matter how many times you fail - The importance of being honest about imposter syndrome - Experimentation to prove your abilities to yourself - His crowdfunding experiment to buy Greenland - Thinking of luck in terms of experiments - His many leaps across diverse fields - The art of developing thick skin - And other topics…   James Altucher is a bestselling author, serial entrepreneur, LinkedIn influencer, and venture capitalist. He hosts The James Altucher Show, a popular business podcast. He has also authored over 20 books, including the Wall Street Journal bestseller Choose Yourself, ranked as the second-best business book of all time by USA Today. James has founded 20 businesses, 17 of which have failed, but continues to actively advise or invest in more than 30 companies across sectors such as technology, energy, healthcare, and biotech. Connect with James: James’s Website: https://jamesaltucher.com/  James’s LinkedIn: https://www.linkedin.com/in/jamesaltucher/  Resources Mentioned: Choose Yourself! https://www.amazon.com/Choose-Yourself-James-Altucher/dp/1490313370  James’s Books: Skip the Line: The 10,000 Experiments Rule and Other Surprising Advice for Reaching Your Goals: https://www.amazon.com/Skip-Line-Experiments-Surprising-Reaching-ebook/dp/B08BLLF3RD

If you want to hear from someone who really did big things, he actually really inspired me when I needed it the most about a decade ago. And I want you to meet him. I want you to see what's possible, but I also want you to see an incredible journey of ups and downs and failures and rejections because we all go through this. James, welcome to the show. Oh, thanks so much. I am honored to be here.

I'm so glad when you asked me to be on the show. This for me closes a little bit of a loop. I briefly told you, but about a decade ago, I found myself in a very tight, really hard spot. I was looking for my career direction. I was trying to figure out, ticked all the boxes, all the way to vice president. And then you came with this amazing book, Choose Yourself. And it was an eye-opening for me, James. So first of all, it's just so beautiful to have you on the show and inspire others with your amazing journey. When I wrote Choose Yourself, it wasn't that I was thinking,

oh, this book is going to inspire others. It was more like a healing for me because it was the events that happened to me when I needed inspiration. And I wish someone had given me the opportunity to be inspired, but they didn't. I suffered longer than I should have. And I want to talk about that because again, if people don't know you, now you're like this investor and entrepreneur and author of so many books and you have this really popular podcast and you're doing so many things. Choose Yourself was one of the top books, but you also have Skip the Line and Reinvent Yourself. But tell us about your story because that's not how it started, is it? It's interesting because what you write about later after the dust settles, it is a healing process to write and to describe your story and to describe things that happen.

And look, what simple things I've been through are nothing compared to what others have gone through. And we see this throughout the world. But everybody's pain is unique to themselves and you can't ignore your own pains. So around the mid-90s, I realized there was like maybe five or six people in New York City who knew how to build a website. And at the time, nobody even really realized you would need a website. Like, oh, what's this web thing? It's for academics. So part of the process was convincing people, you know, you need a website. Like, oh, what's this web thing? It's for academics. So part of the process was convincing people, you know, you need a website.

Like American Express, you need a website. So I was working a full-time job at HBO. I would work all day at HBO and then all night doing websites like AmericanExpress.com, Toshiba.com, TimeWarner.com. And slowly but surely, over years, I built a company making really big Fortune 100 websites. Now, of course, you could just go to Chachi PT and say, hey, make me a website that's for a rap label. And it'll just do it. And it'll make me a newsletter from it and a discussion forum and a place where all

the new artists could upload their song. And it just writes the code and does it. So fortunately, you have to recognize when to get out of a business too. And pretty early on, I realized, oh, I'm not going to be able to charge $100,000 for three pages of a website anymore because there's going to be tools that are built to do this. I will say a big mistake I made was not realizing I knew how to make the tools. I was making the tools to help me build the websites, but I didn't want to tell anybody because I didn't want them to realize how easy it was for me to make a website using software that I had written. So instead of making WordPress, I made a little internet services company building websites, but I still in the boom was able to sell it for

millions and millions of dollars. And then I realized too late, there's three skills to money, making it, keeping it, growing it. So I knew how to make it. At least I thought I did, but keeping it within two years of selling my first company for cash, I didn't have stock that went down or anything for cash. I lost all my money. What happened there? A, I bought a big house. That's not necessarily bad or good, but what I realized is, and what advice I give people much later is that, hey, you just made some money. Do not do anything. Oh, you want to know how to invest it?

Don't. Oh, you want to just buy a house? Just wait. Don't. Wait a year. Let it marinate a little bit in your soul before you do a single thing with it. So you understand a little bit what money means to your life. It doesn't mean you're done with being human. It doesn't mean you're done making money even. You

don't really know what it's like to have more money. So it's a different experience. And hopefully we all go through this experience. But I didn't know anything. So I figured, oh, I must be a genius since I sold a company. Oh, if I can make it here, I can make it anywhere. And so I thought, oh, since I'm a genius anyway, and I believe in the internet, I'm just going to quadruple down on every internet stock possible and buy a big house. And of course I did that and lost everything

almost instantly. Like you can't even describe how fast it was. It was like I was losing a million dollars a week for an entire summer and then was broke. And I remember I was so happy that I had made this. I was able to help my parents. I had little babies. As children, I'm going to be able to help their lives. But I didn't really understand anything about investing, for instance. I had to learn. This was over 20 years ago, but I had to really learn. And I didn't know how fast money can go. And it just disappears instantly. And at one point, I checked my ATM machine. I was afraid to look at it because I

was just scared of the bad news because all I would get was bad news. For years, I thought to myself, can I just have just one win in anything but it just seemed for a long time like things were going straight down and at one time I checked my ATM the same checking account that at one point had 15 million dollars in it now had 143 dollars in it like 143 I called up my parents and said can I just borrow a thousand dollars for a weekend because I was gonna you know we had to sell the house for much less than we paid for it. But I was able to extract a little bit to maybe live for a few months while I figured

things out. My parents wouldn't lend me $1,000. So I hung up and I just didn't know what to do. And fortunately, then the next week, I basically exiled myself from New York. I couldn't afford to live in New York. And I moved to a house way upstate, rented tiny place, and with my then wife and kids. And I was just so depressed. Like I had failed everyone.

I didn't know what to do. I didn't know what to do for a living. I had no job. Nobody wanted to talk to me. Everybody wants to talk to you on the way up. Nobody wants to talk to you on the way down. And that's a cliche, but it turned out to be surprisingly true. I had nothing going for me. People ask me, well, how did you get motivated to get out of the bed in the morning? I wasn't motivated. You can't get motivated when you're super depressed. I mean, I was depressed to the point where I was considering, look, I have babies. They won't remember me if I'm dead.

So maybe that's the better way to go with life insurance. And of course, couldn't legally do that. And I didn't want to hurt myself. So that ruled that thing out. I didn't want pain. But it's important to understand how today I can move forward. I don't need to be motivated because I'm not going to be motivated, but I just need to figure out how today to move the needle in my life a little bit. If I do that today, that's all I need to do. Tomorrow, I'll wake up and deal with this again. But I want to go there for a second, James, because we have so many people that really will resonate with what you just said. And I personally have shivers because I remember a time like this.

What was happening in your time? I basically lost my job. I was kicked out of my startup and left with nothing. And it was like a huge blow to my ego. And I was trying to, how the heck did I find myself in such a failed position? And what do I do now? And I think the hardest thing is for somebody who's driven, and that's why I want to go there with you for a second, for somebody who's driven in general, right? And we'll talk about your childhood because you were driven from day one. So for somebody driven to suddenly not know what's next, that's hard to breathe.

And I want to go there for a second because that takes a toll on everything in your life. It takes a toll on your sleep, on your relationship, on everything in your life. For me, like finally, I had all the time in the world to be with my kids and I wasn't present. For a change, I wasn't flying every week. I should have been the ultimate mom. And instead I was just grouchy and annoying. So for me, I want to go there for a second. What eventually got you to this clarity of what do you want to do?

And we'll talk also about experimentation and regenerate ideas. I think it all connects, but how did you get yourself out of this really hard spot? Because our listeners sometimes are right there with you, James. It's funny because I didn't really realize what I was doing until later in terms of how I was coming back. Many years later, I had built another company, built it up, sold it, made millions, and then went broke again. And I'm like, how could this be happening to me yet again? And I asked myself, what was always working for me on the way up? And what did I stop doing on the way down in order to go down? And it's almost like a cliche,

but I realized, like you mentioned to yourself, during this down period, you could have been building on your relationships or sleeping more instead of not sleeping at all. Like all the things we should be doing actually become worse when things are going poorly. But those are the exact things we should be focusing on. It's like the George Costanza Seinfeld episode where he does the opposite of everything he wants to do. I realized I had to do the opposite of what my entire mind and body was telling me. And it's not very hard to do the opposite. So I just focused on four areas, physical, emotional, creative, spiritual. Physical, because if you're sick, you're not going to have good

ideas and you're not going to start a new business or make money or whatever. Emotional, because if you're arguing with your spouse all day, you're not going to be successful at a business. Creative, because if you have no ideas, you might as well go back to being the janitor. Or I shouldn't make fun of janitors. I love my janitor from school. And spiritual, not in the sense that I'm going to go and pray every day. You could do that if you want. But just realizing, thinking about the past or worrying about the future are completely out of your control. But focusing on what you can do today is the only thing in your control. And so that's the only thing you should focus on.

And it's a practice, but you got to practice not letting, well, if I don't survive within the next six months, I'm just going to be in a homeless. Like if you start going down that path, there's only bad things down that path. If you go down the path of like, well, I shouldn't have invested in this. There's only bad things that happen in that. Sure, today I can learn from the past.

I won't make a mistake today that I did in the past. I don't have to think about it anymore. Very hard to do that, but you have to do that. So with physical health, okay, sleep better, maybe move a little bit more than you normally would, and eat well. Because if you're eating junk food all day, it affects your ability, your energy. Emotionally, again, just work on your relationships. Get in touch with people. Have lunch with somebody. Network a little bit. Just do one thing. Just move the needle 1%. 1% compounded every day for 365 days is actually 3,800%. So I don't know what that means in qualitative terms. Like if my emotional well-being is 3,800% better, it doesn't mean anything, but it has an effect.

And creativity, this one thing happened where I was just walking all around the city, not knowing what to do, but I didn't want to stay in my house because the house, I was losing it anyway, and it was depressing me more. So I walked into this restaurant supply store for some reason, and I saw this big box of waiter's pads. They looked nice, like just these light blue little pads that fit in your pocket. You can't write a novel on a waiter's pad, but you could bullet point stuff, and I liked it. So I bought these waiter's pads. The next day, I go out to a cafe, and I start just randomly writing ideas for books down on the waiter's pad. And then, oh, one book idea I liked. And the next day, I wrote 10 chapter ideas for this one book.

And then I just, every day, just for fun, I was writing 10 ideas a day. And I realized something after just a few weeks. For the first time in years, I was actually excited and happy. Like, something had woken up. And the only thing I was doing differently was every day writing 10 ideas down. And then the rest of the day, I'd go home and get depressed watching the stock market and then go to sleep. And it's interesting, I realized, oh, what's happening is the idea muscle, the creativity muscle is like any other muscle. If you don't walk, for instance, for two weeks, like let's say you have a bicycle accident, you go in bed for two weeks, you'll need physical therapy to walk. And so it's the same thing with

creativity. If you don't use your creativity in some way, after a very short amount of time, that creativity muscle, the idea muscle, atrophies. So I wasn't coming up with 10 good ideas a day. Like that first book that I was trying to outline, I never wrote that book. It was probably a bad book idea. But it was exercising this idea muscle. And so writing 10 ideas a day. And by the way, the 10 was an important number, I realized, because one through seven was always easy. 10 ideas for Ilana to improve her podcast. One through seven, I could do no problem. It's eight, nine, and 10.

It would take like the last, oh, did I make 10 yet? I'd be counting. Oh, no, I'm only at eight. I thought I was at 10 already. And then that's when your brain sweats. It's your exercising. And so you have to quickly get to the seven and then push yourself, eight, nine, 10.

And it's all bad ideas. You're not going to come up with 3,650 good ideas a year. You're probably going to come up with almost all bad ideas. Doesn't matter. It's exercise. What I love about what you're saying, and I think it's an important point, is also the clarity comes from action,

not just thinking about it, noodling about it, procrastinating about it. The clarity came from that action that you created. And I love that because it's about the action and getting there. You can't think your way out of bad thoughts. You know, meditation actually is sort of a way to kind of at least notice when you're having bad thoughts. But I would try that too when I was so depressed. I spent a long time like learning meditation and sitting in meditation and it was okay, but it wasn't really taking me to a new spot in my life. It was like

helped me recognize when bad thoughts were coming up, but then I would just get overwhelmed in them again because I had so many. But action, really, you get excited. Like, oh my God, here's an idea for a book. Maybe I'm going to write that book. Maybe I'll start today. Maybe this will be a new thing for me. And boom. Oh, here's 10 ideas for businesses. Maybe I'm going to do one of these businesses. Maybe I'm going to share this business idea with someone rich and famous, and then they're going to hire me to do the business, and on and on. So that's why I would get excited all of a sudden. And again, I didn't write that book that I first outlined, or I didn't start that first business I wrote ideas for. And often people say, oh, ideas are a dime a dozen, execution is everything. But what people forget is that execution is a subset of ideas.

Let's say, Ilana, you had an idea for a software company. Well, now you have to have execution ideas. Should I raise $3 million and then hire software engineers and get a marketing team ready, and then a year later launch the product? Or maybe I'll have ideas where I can manually do this idea for a friend and see if they're willing to pay for it and then start as a service and then scale it up as a product, which is the business model of many

companies. So there's a whole range of execution ideas, no matter what your original ideas are. So you have to be good at ideas to be good at execution. And I think it's this combination that you're talking about, which is ideas together with experimentation, right? Because it's not just about throwing the ideas. What I love about it is from time to time, you will latch on the idea and say, you know what, I'm going to experiment this a little bit. And we can do this with a book, we can do it with our life, we can do it with a career, with a startup, whatever it is. But if you actually take a few of them and say, you know what, let's experiment. I think this is a big thing that you've been doing, James. And I love that. That's huge. We've been doing this with companies. We've been doing this with individuals. I mean,

that was incredible. How many people have you interviewed, let's just say in the past six months, who they tell you the story of how they went from zero to a million? I did, but they all went through a lot of this on the way. Exactly. So imagine if you just took the transcripts of those interviews, stapled them together, wrote an intro and an outro for each transcript, and now you have a book, you have the first draft of a book. That's an experiment that you could do in the next seven days. You can make a full book on how to go from zero to a million. And look, it might not be good, but it's an experiment. It doesn't cost you much. And then you can decide, okay, I'm going to write a second draft or, okay, this is not a good idea, but maybe there's other ideas. You know, and this was, I saw that this was an easy process. So again, it's like, you have these

ideas, and then some of them, every now and then, you might say, I'm going to go the next step on this idea. Oh, I like this book idea. I'm going to write what the chapters are. Then for each chapter, I'm going to write what the subchapters are. Okay, three days later, wasn't so interesting. I'm kind of bored now. I'm not going to do it. But what you did do is you exercise that idea muscle. So that's always good. So at one point throughout this whole process, I was like, okay, I lost so much money by investing. I didn't go to business school. I don't know anything about finance. I didn't work for a hedge fund or Goldman Sachs, but I told myself, I'm going to learn everything there is to know about investing. And so I literally read every book I could about investing. I read every article. I read every

newspaper. I'd really studied. And then I was a software guy. I wrote software to find patterns in the markets. I wrote software to automatically trade those patterns with what little scraps of money I had left, or I would convince a friend to invest in these ideas and so on so I could establish a track record. But I really spent a lot of time, years and years, reading everything I could about investing so I wouldn't make the mistakes I had made again. And so at one point, I came up with 10 ideas of people I could meet or I should meet in the investing world. So I wrote emails to 20 different people. Hey, I'll buy you a cup of coffee. Can I

please meet you? I'll fly wherever. And nobody responded. And I was thinking about it. Well, of course, it's not like Warren Buffett is going to get my email and suddenly say to his secretary, Gladys, some guy named James Altucher wants to buy me a 60 cent cup of coffee, clear the schedule. Whenever he wants to come in, just let him come in because we got to make sure he's taken care of. So nobody responded. And so I did a lot more research on each person. And I wrote for each person, I wrote 10 ideas for Warren Buffett or 10 ideas for this financial writer, what articles he should write, 10 ideas for this hedge fund manager, what strategies he should do or what stocks he should look at.

And I sent them to everybody and I sent them cold. And I said, no need to respond. Knowing your style and doing some research into what you do, I thought this would be interesting ideas for you. No need to respond at all. I wanted zero pressure and zero friction on everybody. That is so brilliant, by the way, James. It is a strategy that I've been using ever since. And it is magic. So even on this first email out, out of 20, I got three responses. One person said, hey, these are great ideas for articles I should write, but how about you write them? And so that was finally, after 10 years of writing in my garage or whatever, I had my first paying gig to write articles. Mind you,

this was after I lost $15 million. I was so grateful. I was going to be paid $190 per article. Oh my gosh, what a wonderful thing. And then I wrote to a hedge fund manager who responded. I wrote to him, here's 10 software, 10 programs that model the markets the way I know your hedge fund models the markets. He was impressed. And I said, you could just show this to your programmers if they have questions for me, happy to help. I kind of had maybe more arrogance then than I do now about, well, of course he's going to be interested. And he did write back and said, ultimately he invested money with me and I started my hedge fund to trade money. And so all of a sudden,

out of this first batch of emails, I had two completely different career tracks, writing about investing, something I didn't know about a few years earlier than that, but now I feel I was an expert. And I was actually professionally managing money with a hedge fund. And it forced me to further learn about investing and the history of investing. And I find that even now, like I look on CNBC, which I rarely look at, and I see the talking heads talk, and I realize, oh, this person, he might know about stocks, but he doesn't know about bonds, or he doesn't know about options, or he doesn't know about how real estate works. People don't really study their craft.

The path to mastery is a great path to be on, and it involves knowing the history. People didn't know, weren't aware of the great investors in history. I would talk to famous talking heads on CNBC. They wouldn't know even Warren Buffett's history or other great investors or Benjamin Graham, his mentor, or Bernard Baruch from even before. They wouldn't know the real story about the South Sea bubble or things that were happening in the 1600s that are informative to learn and know now because history doesn't repeat. It rhymes, particularly in investing. But in any case, the career with writing, oh, then soon the financial times wanted me to be a columnist the wall street journal and then wiley called me hey could you write a book and so now

i was writing finance books and i had spent the prior 10 years being rejected as a novelist i wanted to write novels like i got thrown out of grad school because i was writing fiction all the time and i kept writing novel after novel but nobody would publish me because horrible but i novels. I got thrown out of grad school because I was writing fiction all the time. And I kept writing novel after novel, but nobody would publish me because it was horrible. But I got better in those 10 years. And so now I was a finance writer writing with a professional writer's aesthetic. So I was different from all the other writers. And often one thing you can do in life to be special in your area is to not be the best at finance and not be the best writer, but be best at the intersection of finance and writing.

So suddenly I had two careers out of this, and that kind of evolved into my next business, which I sold and then lost. And then I had to downsize again and so on. But I was able to repeat the process like, okay, 10 ideas a day, what am I coming up with? Even to this day. So I'll still come up with ideas for others. I'll cold send 10 ideas to Amazon, 10 ideas to Google, 10 ideas to wherever. And because of that, I've been cold invited out to Amazon, Twitter, Google, Facebook, LinkedIn, Quora, and Airbnb. And I've spoken at their conferences or at their buildings, or I've done consulting for them. And one time I cold emailed

Amazon, here's 10 ideas you should do for your self-publishing business. They were really into self-publishing. They still are, but they were just starting in 2012 or 2013 or 2014. And they said, hey, if you're ever in Seattle, we'd love to talk to you more about these ideas. I said, oh, it just so happens I'm going to be in Seattle next week. Now, I had never been to Seattle before in my life. I never had any plans to go to Seattle. I didn't have any plans that next week. You made plans. Yeah. They're going to talk to me about self-publishing and they're going to ask for my opinion and then I'm going to have contact with them. That's great.

So I dropped everything. I flew out there and became friends with them ever since. And I've self-published a bunch of books since then. And Amazon's always been great. So you build up bit by bit over years, the seeds, not the seeds necessarily for success, but the seeds that help prevent failure the next time it happens. Because there's always going to be bad things that happen, but you want a community around you and you want to learn things so that you can provide value for a community and freedom

so that if you fail again or if things happen again, you still have freedom in your life. You have people who are around you and you have skills you've mastered and so on. And that's real. It's not about getting money because money might not buy you freedom. It's really this combination of mastery, well-being, and a sense that you're making your own decisions in life and not waiting for someone else to choose you. What you just said, James, I think is so critical because it's not the challenges that stop most people, it's their belief about these challenges

that stop them, right? And that belief, I can't do it. See, I lost it all, so I will never make it again. So it's that belief that actually spirals you down and you somehow manage with those same ideas as when hustling and all of that, you managed to get out of that belief and just create a new belief of, I will make it anyway. So that is hard.

It is hard because I don't know if I could do that. I would say everybody's got a baseline of happiness. So you have this baseline, and if you break your leg, you're not as happy. But then a couple weeks later, I'll deal with it, and you're back to your baseline. Or something great happens to you, you make a million dollars, you're happy for a little bit, but then you're back to your baseline. And I think my baseline, honestly, is kind of lower than most people. So it's hard for me to not negative self-talk. But again, it's like what you were saying earlier. If you take action, it doesn't matter.

So if I go on the plane to Amazon and talk to them and bring my best to that meeting, that is a good thing, whether I believe I'm an imposter or not. I'm a living, walking imposter syndrome. It's a cliche to say I shouldn't even be on this podcast, but I'll give you an example. I was a Norway keynote speaker at the Norway Business Summit. And then afterwards, I was on the stage interviewing their top central bankers. It's equivalent to interviewing the Jerome Powell of the head of the Federal Reserve in the U.S., the Jerome Powell of the head of the Federal Reserve in the US, the Jerome Powell of Norway. And I even turned to the audience and I said, what you're watching now, this is an example of imposter syndrome, me talking to these

people who run the entire bank of this country. But you got to still do it. And it's okay to be honest about it. Don't be afraid. Be yourself because people appreciate that and they recognize authenticity. But you got to do the challenges. You're challenged in life for a reason. It doesn't mean say yes to everything, but take the challenges that are intriguing and live up to those challenges. Whether you believe in yourself or not, then you learn to believe in yourself. If you do it, you could believe you did it. Exactly. And you stack the evidence of why I can instead of why I can't, right? Which is so, so, so powerful. Yeah. Like now if the central bank of Nigeria wants me to talk to them, I know I could do it.

But I think the beautiful thing is with our achievements, every time we get to a new achievement and that becomes the new norm. And now we're as high achievers, we always going to try to aim higher. But the interesting thing is how we normalize it. Like now we got to a certain place and now it's like, okay, that's the norm. Now what else is possible? Okay. so let's say you're not so driven. You mentioned the word experiment. I really love the idea of doing experiments to show yourself, oh, I could do X, Y, or Z. So I'll just give you an example of an experiment. The experiment was a writing experiment. So I was tired of writing these first-person narratives, and I'd been experimenting with some second-person narratives, third-person narratives.

And then there's a structure where it's the epistolary style, where you write an article as if two people are writing letters back and forth to each other. But what about writing an article that's like a Kickstarter style, where the article itself is structured as if it was a Kickstarter campaign? I didn't know structured as if it was a Kickstarter campaign. I didn't know anything about Kickstarter or crowdfunding, so that's why I did all this. And then the article was my Kickstarter campaign, was a new way for me to experiment in writing in a different style. But along the way, I learned about Greenland.

I learned about crowdfunding. I learned about rare earth minerals. I learned that Kickstarter eats the chargebacks whenever a campaign shuts down. And then I learned, I expanded my horizons of my writing and I get a story out of it. And who knows, maybe it could have worked. God forbid, I could have raised a significant amount of money and then it becomes a big thing. So that's the great thing. The entire process, 24 hours, and yet so much I get out of it. So an experiment was like writing those emails saying, here's 10 ideas for articles

you should write. Here's 10 ideas for Amazon. Here's 10 ideas for Google. Another experiment. So for about six years, I got obsessed with stand-up comedy. And I got really involved to the point where I was performing 10 times a week, you know, multiple times a night often. And I traveled all over the U.S. I even did stand-up all around the Netherlands. And I was performing with very famous people. I mean, I'm cracking up here. I'm trying to not make noise, but I'm cracking up here as you talk.

So I get where that came from. Because it's so ridiculous, the idea of me doing stand-up. I'm trying to not make noise, but I'm cracking up here as you talk. So I get where that came from. Because it's so ridiculous, the idea of me doing stand-up. I get it. But at first, I wanted to practice. It's very hard if you're not a professional stand-up comedian to get on stage. So I wanted to practice against hostile audiences because invariably, you're going to be bad and you're going to have a bad audience. So I did an experiment. I went on the New York City subway and every stop I would change cars and I would do standup at rush hour on the subway. And that is a hostile audience, but it forced me to get really tight with one-liners and deal with negative feedback and try to get people to laugh.

So that was an experiment. But then I figured, you know what? What's the format of every late night TV show? Now, when you have a format, it's okay to change the format in subtle ways, but you keep the basic skeletal structure. So late night TV show has usually the late night host, Jay Leno, Jimmy Fallon, the classic late

night host. They would do a standup monologue. They would have a celebrity guest and they would have a musical guest. That's kind of the skeleton of a late night show. So I figured, well, I could do standup on a subway. I could interview someone on a subway and a musical guest could be one of the people just hitting garbage cans on the subway station. So that's what I did. I found a musical guest like that. A friend of mine had just published a book. So I interviewed him on the subway and we interviewed. I had audience reactions to what he was saying about what he was saying. It was very funny, actually, what these people were saying. And I put it together in a 25-minute video. I sent it to a TV agent. I said, I'm pitching a new idea for a late-night show that happens on a subway. And this agent wrote back and he said, it's not good.

And that was that. But who knows? A, he gave me this great experience. B, what if he had said, yes, this is great. And you never know when experiments, you learn something. At the very least, you learn something. At the second least, you have a story to tell. And at the third least, something amazing can happen. The more experiments you do, the more opportunities for something amazing to happen. We all sit there every day waiting for something amazing to happen to us, like magic. And you can't just sit there. I can't just sit in my backyard waiting for amazing to happen.

Create your own luck, right? Yeah. By thinking of luck in terms of experiments, you expand the horizon by which luck can happen to you. And you invite amazing into your life through simple one-day experiments, two-day, three-day experiments. You could start an entire company as an experiment, see what happens. If it doesn't work, you shut the experiment down. Totally resonate, James. I do see also two other themes. One is your level of curiosity, because you're not afraid of learning new things. You're not afraid of diving in. That level of curiosity is really, really interesting. And I think the other one is just not being afraid to

try because going into a cart and fishing like that sounds really scary to me, James. So that's incredible. I was scared to death. I went on the train. I went with a friend who was going to videotape me. And I said to my friend, you know what? I'm not doing this. We'll just take the subway and get off. I'm sorry I wasted your time. And then I, after a few seconds, I said, my friend, you know what? I'm not doing this. We'll just take the subway and get off. I'm sorry I wasted your time. And then after a few seconds, I said, you know, we're on the subway. Just turn on the video camera. I am not going to do this. There's no way.

I'm terrified. I don't want to do it. And then she turned on the video camera, and I did it. And then that was it. Then I just did it from car to car. I saw I wasn't going to die. And sometimes people laughed, and that was fun. And sometimes people laughed and that was fun. And sometimes people were like, what the heck? Get out of my face. That didn't kill me. I was

scared though. Again, I used to wonder about this, like, oh, you have to avoid fear or you have to be motivated to do something. You don't have to be either of those things. You just have to know that doing things is better than not doing things. Sometimes it's actually okay to rest and not do something. But in general, you want to engage with life as much as you can reasonably. You don't want to burn yourself out. But life exists around us as an invitation. And so you want to accept that invitation as much as you reasonably can. Love that.

Richard Branson, by the way, has a quote I really love. It basically says, the brave don't live forever, but the cowards don't live at all, right? And I think what you're basically saying, be afraid and do it anyway, which is interesting. Yeah, because who wouldn't be afraid? You have to be crazy not to be afraid to do stand up on a New York City subway. And you have to be crazy to do most things. Even starting a company, you're going to be crazy because you're doing something that no one else has done before, which is why no one succeeded at that business idea before. But this is also, again, one of the things that I'm seeing about you, James, and if that's

okay, I want to take you back a little bit because what I'm noticing is that you have this theme since childhood of being bold, doing things anyway, and success leaves clues, right? Which is kind of interesting to see the clues throughout life. And if I'm looking with little that I know about you, first of all, I think you started a business in college or really young, and you also pitched something in HBO. So I would love to go there for a second because again, it's kind of who you were. I think when you were down in this downhill spiral, it's really easy to forget who we were, but it's also interesting to start looking back and connecting the dots, as Steve Jobs says. So connect the dots for us for a second. I think the dots might come out of insecurity. Like,

oh, I'll be liked if I'm successful at something instead of just being liked for who I am. But combine that with, I was always a little obsessed with things. Every year of my life, I was obsessed with something, starting from six years old on. And then I would be like that weird kid who only wants to talk about Greek gods when I was six years old, or astronauts when I was seven years old. I was obsessed with politics. In fourth grade, I was around 1978, I'm 56 years old. So in fourth grade. Fourth grade, I was around 1978. I'm 56 years old. So fourth grade, it was a few years after Nixon was impeached. So I read all of the House proceedings of the impeachment trials for Nixon. Even my teacher was like, what are you reading? It's this thick

thing called the presidential transcripts. And I just was obsessed with Nixon's impeachment and politics in general. And that lasted for a while. So I went to the Democratic National Convention when I was 12 in New York City. And then I was trying to interview the presidential candidates. So I called up the Federal Elections Commission. There was no internet sites then. They sent me a printout of all the candidates for president. There's hundreds of candidates for president every year. And I would just start calling them and interviewing all these crazy people who were writing for president, including some famous people. And so I would say I was writing for this newspaper. I was lying, unfortunately, because the newspaper then, the editor-in-chief called me and said, you can't claim to be from this newspaper. We don't even hire PhDs in journalism. We're not hiring you. You're 10 years old. But he gave me a tour

of the newspaper. And then another newspaper did publish my interviews. And every year, I got obsessed with things. And that really drove me to get good at different things, get good at computers when I was obsessed with computer programming, get good at different things. Get good at computers when I was obsessed with computer programming. Get good at chess when I was obsessed with chess and I became a chess master when I was relatively young. But sometimes it's not so good. Sometimes I look back like, why did I spend six years doing stand-up comedy instead of, oh, maybe starting another business and building that up? But I've done well. I've been successful. I'm still successful. I haven't slipped back for an eighth time, but I've never really been driven as much by money as maybe one normally is. You don't make any money for six years doing nothing but stand-up

comedy, for example, or playing chess, which I did for years. So what motivates you, James? I think only being interested in things and getting good at the things I'm interested in. It's the only thing that has ever been any motivation for me. And whenever I've been single, looking for someone to date and marry. I'm the marrying kind, so I've always wanted to date and marry quickly, but I've had a couple of marriages as a result. So from that point on, fast forward to this bestselling author, a podcast that people are knocking on your door, something took off. What do you think it is and how do you maintain it? Yeah. I don't know because again, I think my baseline of happiness is a little lower than most people's. I think I'm an optimistic person and I think I like to be happy, but it's always a little

bit more of a challenge. And I've had some ups and downs the past few years that have changed my life in various ways. Like in August 2020, in the middle of COVID, I lived in New York City. I was very concerned about what I was seeing in New York City in terms of economically, where things were going during the lockdowns. New York City needs a lot of money every year to open the doors. They need to have over $100 billion in revenues every year from taxes to open the doors and to pay for police, sanitation, teachers, healthcare workers, transportation

workers, in addition to what the state needs to run the subways and buses and bridges and so on. So I wrote an article to try to get people's attention that there are real problems because I thought everyone was in denial. So I wrote an article called New York City is dead forever. Here's why. In the article, I expressed my love for New York City, but I also said, look, these are the problems. And I always say to people, if I'm not afraid when I hit publish, then I don't publish. Because I know if I'm not afraid when I hit publish, I'm not saying anything really new or interesting. And so I wrote this article, and within minutes, I started getting so much hatred,

mostly from people in New York City, and I get it, because they lived there, and they wanted to defend their city. I made the mistake on Twitter of responding to people. I kept saying, I'm not, I love New York City. That's why I wrote this. I'm not some guy abandoning New York City and dancing on its grave. I wanted to succeed. That's why I wrote this, but everybody hated me,

and then people like Rush Limbaugh at the time, on its grave. I wanted to succeed. That's why I wrote this. But everybody hated me. And then people like Rush Limbaugh at the time, Glenn Beck, Joe Rogan started quoting. Rush Limbaugh read my article word for word on the air. And so, of course, New Yorkers hated this. I didn't have anything to do politically with any of this at all. But people, of course, said you're guilty by association and New York City's one way and Rush Limbaugh and Glenn Beck are another way and Joe Rogan. And so now it's getting double hate. Then Jerry Seinfeld, who was a comedian, but the comedian I admire most, wrote a full page op-ed, the first op-ed he's written in his entire life, just trashing me. He didn't even respond to my argument, just trashing me. Who

is this putz, James Aldrich? And then Andrew Cuomo read his article live and emailed it out to 10 million people. And it just became this thing. And people would remind me like, oh, it's to your credit that your writing is powerful and struck this nerve. This is like the last viral article ever at this point in history. But it basically drove me out of New York. The comedy club that I then became a part owner of was vandalized. My employees were being harassed in the street. So I ultimately moved out of New York. It wasn't pleasant for me. And I'm friends with the new mayor. I helped him figure out his campaign when he was debating running, Eric Adams. But the problems are very hard, as he's seeing, as the people are seeing. And I think I got depressed after that because family members were writing articles

against me. Ex-girlfriends were writing articles against me. Friends who I'd given their first job to were writing against me. Friends of mine were losing friends if they stood by me. Friends who I'd given their first job to were writing against me. Friends of mine were losing friends if they stood by me. I don't know why it became such a big deal, this one stupid article, but it did. And I shouldn't have let it affect me as much as it did, but I did get depressed. I kind of stopped writing. It was almost a subconscious thing where I couldn't write anymore because there was punishment in my brain for writing. And that's when I dropped out a little bit. And I hadn't played in chess tournaments for 25 years. And again, I was an accomplished chess master in like 1997. Then I stopped playing,

but I picked it up again because it's this intellectual pursuit that I could disappear into and I don't have to deal with people. I rationalized it like, oh, I'm going to prove that someone in their 50s could be as good as someone in their 20s, even after this break, which has not happened yet. and taking lessons and talking to neuroscientists about what's the difference between a 56-year-old brain and a 26-year-old brain and getting coaching and getting physical coaching and changing my diet and all these things just to get better at chess. And I still have not gotten back to my old level. I'm the Georgia senior chess champion, but it's not as good as being the New Jersey junior champion, which I once was. So yeah, I kind of think I got a little down and I kind of dropped out a little bit

and hasn't always been sheer success. But I think the big changing factor for me was being able and comfortable writing my own personal stories, which I started doing pretty early on. As opposed to just writing about stocks or investments, I started writing, hey, this is what happened to me when I went broke. And people were like, why are you doing that? No one's ever going to trust you with money again. I'm like, I don't care. And I just started writing all these authentic stories. It turns out I've had more opportunities than ever financially because I started writing in that manner. And now a lot of people write in that manner, but at the time, no. And I think that was a big change for me. And I think that's where I got to know of you because you spoke the language of

people that actually need to hear that because you always compare yourself to someone else's success, but it's really hard to understand what their journey is, which is why we're doing this podcast. I really want to show people the behind the scenes. Like it's not all pink and purple and beautiful, right? There's a lot of hard moments that really are what defines you. But I also want to talk a little bit about thick skin because I think as leaders, yes, we need to be authentic and we need the vulnerability of Brene Brown, et cetera. It's all very, very true.

And I think when you're in a better place and you're in peace with yourself, you can also be more vulnerable. And you've been just so humble. It's pretty amazing. But you also need a layer of thick skin, which I think I'm still working on. But I think it's just a level of how do you get better? And I think I get a lot of questions about that from people who are kind of leaping to C-suite or to entrepreneurship is how do you become better at absorbing these hard naysayers, people that bash you? You get a lot of this all the time.

How do you get better? I mean, it's very hard. The only way to get better is to get beaten up again and again, and that's how your skin gets tougher. I remember back in 2003, I had just started writing about stocks, and I had never had any bad feedback about anything in my life from the public because I had never been public about stocks. And I had never had any bad feedback about anything in my life from the public because I'd never been public about anything. Suddenly I got this message, oh, you're an ugly Jew. And I got offended. So stupid to get offended over a cliche anti-Semitic remark from an anonymous

person on the internet. But okay, I had to realize this is stupid to get offended about. And then gradually, you take opinions and more and more people listen to your opinions, but then more and more people hate your opinions. And some of them, the vocal minority, state he's a jerk or he's a goddamn idiot or whatever they say. And then they get more and more insulting. And I realized about every two years or so, something would hurt people and the hate would get even 10 times bigger than the last time. And then I got better and better at dealing with it. One time though, I was writing about Bitcoin in 2017 and a lot of people hated what I was saying. I was getting really upset. And finally, I said, it was like two in the morning

on a Saturday night. And I said, here's my phone. I tweeted, here's my phone number. If anyone has a problem with me, call me right now and I'll pick it up. And well, the rest of the night, I was just talking to people and people would even tweet afterwards. I just spoke to James. What he's doing is very reasonable. I changed my mind, whatever. So that's how I dealt with it at that time. But in 2020, again, it was 10 times higher and the hate was so much. I mean, I was trending on overall Twitter. There was something like 10,000 tweets a second coming out about hating me. And again, not just from anonymous people, but from people I knew also, even family members. So I made the mistake

of trying to argue again with everybody on Twitter, and that just fuels the fire. If you don't fuel the fire, I'm pretty sure it always disappears in 24 hours. Everything will disappear in 24 hours. But if you fuel the fire, it's like you're lending your entire audience to them. Somebody who's anonymous, like an anonymous guy in a mental institution in Canada is saying, James Alventer put a chip in my head and he's evil. And then if I say, no, I'm not, he just suddenly got all my followers or all my listeners or readers paying attention to him. So he just goes on and on. And then other people say, oh, well, that guy got a response and he's in a mental institution. I'm going to now express my hatred. So it just feeds, it's a fire that feeds itself. So basically the more successful you are, the more you're in the forefront. That's crazy.

Yeah. Okay. Elon Musk, obviously 200 million followers on Twitter. He owns Twitter. And he's the richest guy in the world too. So he gets a lot of hate. And he, I would say, has a very tough skin. Not everybody's perfect. When he breaks his toughness, when he slips a little bit and you could see, people say, oh, well, how could Elon Musk respond? Then people jump on him for the few moments he shows weakness. And I was showing weakness all the time. I was just trying to argue with everybody and say, no, you're wrong. I'm really a good guy. Nobody cares if you're a good guy or not.

They just want to get hurt. And this is a vehicle. You become a vehicle by which they get hurt. So you have to remove the oxygen from any fire. And that's the only way to do it. So I don't know if my skin got tougher, but my techniques got better. So now I still get a lot of hate. I don't respond to anybody who gives even the slightest degree of hate. I mute the conversation. I mute the person. I don't block them because then you give them energy because

they see you block them. I just mute it so I don't see it. And I'll respond to disagreement if it's smart and I can discuss. But if something's stupid, I don't respond to it all because I see that it's very damaging to me. I don't care about them. It's damaging to me. It's not getting you closer to your goal. So why bother? I totally get that. But that's beautiful. I mean, it's hard because the more you're out there, the more you know it's coming. For me, it's easier to a little bit remember my why and get a little better about the thick skin because I remember why I'm doing what I'm doing and that's just not going to take it away from me. But it is still hard and it is still painful. Sometimes I see someone say something insulting like, oh, this guy's a whatever. And I feel like

this one time I'm going to just say, no, here's why you're wrong. And then I realized he just got 12 views on his tweet. And my tweets, for better or worse, might have 20,000 views. And so why would I respond? Not that he's not worth it, but he didn't say anything that's worthwhile to respond to. He just insulted me. And it's not that I developed a thicker skin, but now that I don't respond and give oxygen to it, I actually have fewer tweets, emails, posts, whatever, hating on me. So I have fewer haters. And then I don't need a tougher skin. And also remember that usually they're hating because of something in their life.

It's unrelated to you. They're taking it off on you, but it's not related to you. So it's basically like noise in the system, move on. Like how many people who are successful, their families don't talk to them for some reason. Many people, because people get jealous. Old friends get jealous. Some family members get jealous, some don't.

That's how you know who's really behind you. You don't know that though, if you try to respond to them and argue with them, you only know that by ignoring them and see who survives. I love this. James, we have a little tradition in our podcast, and I would love to run it by you. So I always like to hear really successful people and what would they advise their younger self and whatever that is.

That could be a decade ago. It could be two decades ago, whatever that is for you. But what would be one advice that when you really needed that, you would tell yourself? It's so hard to say because of cliche reasons. Like on the one hand, you could say, oh, I'm happy where I am. So I'm glad everything that's happened to me has happened to me. Maybe if I didn't have some failures, I would be more arrogant or I wouldn't know how to have a tougher skin or I wouldn't have started writing the way I do. But if I could just give advice in general,

think of success and goals in terms of not your net worth, but your relationship to your community and the people around you, your feelings of mastery. Always try to get better at the things you love doing. The side effect of that, of course, is money in many cases. And try to make more decisions for yourself instead of having other decisions made for you. We spend a lot of our times waiting. Will so-and-so choose me for a job? Will this publisher publish my book? Will this man or woman like me? Will I get promoted at the job? Will this venture capitalist fund me? So we're waiting for other people to make decisions that affect our lives.

So freedom is the opposite of that. The side effect of all these things, community, mastery, freedom, is going to be things like money. It's going to be better relationships. It's going to be more happiness. It's going to be being in different subcultures because you're going to master multiple areas of life and skills. So that immerses you in different subcultures that could be fascinating. And again, maybe sometimes I

regret, oh, maybe I should have put $10,000 into Uber and have $80 million five months later. But okay, I've done well. You don't have to be a billionaire to be happy. And I think a big mistake I made early on was thinking I needed more and more money in order to be happier. And that was a big mistake. So I guess that's the advice I would give. These learnings are really, really important, which I wish somebody would have told a decade or two ago, maybe even as a teenager. Because again, I think these are the things that shape us.

That extreme ownership that you talked about is not looking for who's to blame, but always look at yourself. What can I do better? Right. What can I take action? So I love everything that you just talked about, James. Yeah. And you can always get like more specific, like, Oh, if you're an entrepreneur, understand the difference between a service business and a product business, because they have different valuations when you sell a company, like then you get rid in investing position size is more important than what stocks you pick,

because risk management is more important than picking a good stock. On writing, write your whole article, cut out the first paragraph and the last paragraph, and then submit the article. That almost 99% of the time makes your article better. So there's finer advice. I like the broad advice too. And I think it boils down to what you just said is there's a lot of layers that you don't know that you don't know. Find the information. Don't lean on the fact that you're supposed to know everything. The information is out there. The mentors are out there. The people that have done it like James are out there. how do you find the answers and not

just go blindly assuming that you know? So I love that, James. It's just such an honor to have you on this show, James. For me, it's a personal closing loop a little bit. Again, you caught me in a really hard time in my life. And you gave me personally a lot. I know you're giving all our listeners a lot right now. This is really honest and humble and beautiful conversation. Because again, you're such an authority in your space. You are very humble, but you've been so successful. You inspired a lot of people with your words and with your stories and with your personal

ventures and journeys. So first of all, just wanted to say thank you. Thank you for coming. Alana, thank you for having me on. I really always enjoy talking about these things and everybody goes through something and whatever a little bit we as communicators could do to help people, I feel really grateful that we could do so that maybe someone who could have told us these things could have saved us from some hardships. And it's good to be able to help you help others. And I'm glad you invited me.

Thank you so much, James.