Become An Idea Machine With James Altucher: Create, Experiment & Adapt

The dystopia is here. Chaos, confusion, fear and anger. Horrific racism. Generations of pain fueling rioting and violence. Death and illness. Faltering systems and leadership failures. Market crashes and jobs lost. Communities are divided. Home lives are disrupted. Meanwhile, cities all across America are literally on fire. How we can right the ship? Deal with these cataclysmic shifts? And move forward productively? We can crash and burn. Or we can adapt -- a remaking of society that begins with personal reinvention. James Altucher is a virtuoso of this process. A prodigious intellect and abundantly talented polymath, James is a comic, chess master, entrepreneur, investor and prolific writer with over twenty books to his name, including the Wall Street Journal bestseller Choose Yourself. He's also a fellow podcaster and an unconventional thinker with an idiosyncratic lens on pretty much everything from creativity to finances. James and his writing have appeared in major media outlets including The Wall Street Journal, The New York Times, The New York Observer, Techcrunch, and The Financial Times. His blog, JamesAltucher.com, has attracted more than 20 million readers since its launch in 2010. And The James Altucher Show ⁠regularly appears in the top 100 podcasts on iTunes. On the subject of self-experimentation, James' latest unconventional move was releasing his latest self-published book, Think Like a Billionaire, on Scribd. Most compelling is James' relentless devotion to constant reinvention. Making his fourth appearance on the podcast, today we explore the importance of this trait ⁠and the habits that enable you to adapt and thrive in rapidly changing times ⁠— more critical now than ever. Recorded pre-pandemic in mid-February, this conversation is the last in my stash of episodes banked before quarantine. Nonetheless, I suspect you will find our discourse highly applicable to our current moment -- packed with tactics and strategies you can deploy to better acclimate to the rapidly changing circumstances that face us all. It's about how to make better decisions. And ultimately, how to create opportunity out of calamity. The visually inclined can watch it all go down on YouTube. And as always, the audio version streams wild and free on Apple Podcasts and Spotify. James is one of my most favorite people. He’s a natural and gifted conversationalist, his ideas are easily deciphered, and packed with the perfect amount of humor and data-backed insight. To some degree, we are all being called to reinvent ourselves right now. May this conversation help serve that process. Peace + Plants, Rich Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Rich Roll?

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• 0:44Rich Roll?

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• 1:05Speaker 01

  Vulnerability, like the kind you experience in AA, or one should experience in writing and maybe all forms of art, vulnerability sort of buys freedom. Like, when you're vulnerable, when you are able to admit to what can go wrong, what has gone wrong with you in the past, the mistakes you've made, now you're free. Like, if I'm writing something, I don't publish it unless I'm afraid of what people are going to think of me. I just ask myself at the end, right before I hit publish, am I really saying something new and unique here? Because I don't want to say something that everyone else has said. Or am I saying something where I'm really afraid, oh no, what are X, Y, and Z going to think of me? What are these people going to think of me? What are my friends going to think of me? What are my readers going to think of me?

• 1:48Speaker 01

  So I always have to double-check myself, because if you're not afraid of what you're creating, there's a chance then that, okay, everybody else has done it, because they weren't afraid either. And so there's got to be some resistance somehow that you get over. And yeah, I'm just being authentic, and that allows me to be as creative as I want in this area. I'm creative even about my mistakes.

• 2:09Rich Roll?

  That's James Altucher, and this is the Rich Roll Podcast.

• 2:24Rich Roll?

  The Rich Roll Podcast. Hey, everybody. How you guys doing? So, right now, as I record this, it's Sunday afternoon, May 31st, and I'm, once again, coming to you with a heavy heart because I'm bearing witness to riots and protests here in Los Angeles and all across America, growing in numbers, growing in intensity, cities literally burning, and it's as if the country is descending into this dystopian chaos. So, in an effort to collect my thoughts on our current state of affairs, I wrote a piece that I just shared on Instagram

• 3:08Rich Roll?

  a few moments ago, which I think I'd like to just loosely riff on here because it's difficult to know what the right thing to say is. And I know for myself, I feel somewhat paralyzed when it comes to publicly sharing a perspective on what's going on right now because I really, really don't want to get it wrong. This is a time in which I think it's much more important for somebody like me to listen than to just pontificate for the sake of pontificating. But there's a tension because I also feel a responsibility as somebody with a platform and an audience

• 3:47Rich Roll?

  to somehow participate in the process of provoking positive change. And the thing is, the truth that I really need to own is that I am, in so many ways, a beneficiary of systemic racism. I'm a white man. My life is the direct result and product of tremendous privilege. I can walk down any street without unease. I can run anywhere without any apprehension. And pretty much everywhere I go, doors swing open. And because of this, it doesn't really feel comfortable or right to weigh in on this historic moment of cataclysm.

• 4:32Rich Roll?

  And yet, what is the point of this privilege if it isn't used to help empower the voices that too long have gone unheard?

• 4:42Rich Roll?

  The world is in chaos right now in so many ways because we, as both individuals and as members of a collective society, have time and again failed to truly redress the toxic racial divide that is woven into the very fabric of this country, a nation that was birthed out of a violence not entirely dissimilar from what we are seeing today. This pot has been brought to its current dystopian boil by galling failures in leadership, countless infuriating miscarriages of justice, foundering efforts at true social reform,

• 5:25Rich Roll?

  the rise of brash authoritarianism buttressed by an increasingly militarized police state that perpetuates violence completely unchecked. We see the weaponization of media and broken economic and political systems that aggrandize power and accelerate the rapidly growing divide between the very few haves and the countless and invisible have-nots. This moment really should come as no surprise because disenfranchisement cannot be decoupled from the anger, the confusion, the fear, and the chaos that it creates, and the silenced must be heard. Now, look, I don't condone violence.

• 6:07Rich Roll?

  My heart grows heavier and heavier with each new report from the rioting frontlines, but I really think humanity is facing a choice: are we going to crash, or are we going to rise? Personally, I choose rise. My hope is that this burn is not for naught, that the ashes of this devastating upheaval will ultimately unite us to finally reimagine and recreate a society that values true equality and opportunity for all.

• 6:43Rich Roll?

  So that's the post. And one aspect of what I was trying to get at is that social change begins with personal change. We can't shift systems without shifting ourselves, without an honest, uncompromising, objective appraisal of ourselves and inventory of our behaviors. So, in admittedly very clumsy effort to now segue to today's conversation, which I think it's important to point out was recorded way back in mid-February, and therefore free of coronavirus or social unrest discussion, today's conversation pivots on the subject of personal change, the importance of being teachable, adapting to changing times,

• 7:27Rich Roll?

  and committed to constant growth and self-reinvention, which I think is more important now than ever. My cipher for this exploration is my friend James Altucher, who I consider in many ways a virtuoso when it comes to reinvention. Returning for his fourth appearance on the show, James is, well, James is many things. He's a prodigious intellect, he's an abundantly talented polymath, he's a comic, he's a chess master, an entrepreneur, a prolific writer, I think he's written over 20 books, including the Wall Street Journal bestseller Choose Yourself,

• 8:09Rich Roll?

  which is my favorite. He's a fellow podcaster, and a fairly unconventional thinker with an idiosyncratic lens on pretty much everything from creativity to finances. James and his writing have appeared in major media outlets, including the Wall Street Journal, the New York Times, the New York Observer, TechCrunch, and the Financial Times. His blog, jamesaltucher.com, has attracted more than 20 million readers since its launch in 2010. And his podcast, The James Altucher Show, regularly appears in the top 100 podcasts on iTunes. What's

• 8:49Rich Roll?

  most compelling to me about James is this drive that he has to constantly reinvent himself. So today, we're going to explore the importance of that trait. And the ability and the habits that allow one to adapt and thrive in rapidly changing times, something that I think is more critical now than ever. But first.

• 9:21Rich Roll?

  Okay. James, thinking differently, learning how to fluidly adapt to change and reinvention. These are the things that we're going to talk about today. This conversation was recorded back in February. It's the very last in what used to be a pretty large stash of episodes banked before we went into quarantine. However, I think you're going to find that much of what is discussed today is highly applicable and can be deployed to help you navigate our current circumstances. This moment in which we are all being required to adapt and to varying degrees reinvent ourselves.

• 10:06Rich Roll?

  This is about how to make decisions, how to find and create opportunity in uncertainty, how to cultivate creativity, and also it's about how to create financial stability. James is one of my very favorite people. He's a natural and gifted conversationalist. His ideas are easily deciphered and they're packed with the perfect amount of humor and data-backed insight. So here we go. This is me and James Altucher. It's nice to have interesting people come to your house and I think that they, my theory is that they infuse this place with their energy and there's a, there's a certain like

• 10:48Rich Roll?

  kind of permanence to that, that I feel like with every guest that comes, like this place becomes better.

• 10:56Speaker 01

  I like that.

• 10:57Rich Roll?

  And also, I think just having people in your home, it makes them relax a little bit.

• 11:01Speaker 01

  I think it makes them relax, and I think it makes them see, view you as, it makes it easier for this to be a conversation, because I'm in your home. I'm not just sitting back waiting for you to interview me like a reporter.

• 11:12Rich Roll?

  Exactly.

• 11:13Speaker 01

  This is your home. How long have you lived here?

• 11:15Rich Roll?

  Since we built the house, 2003.

• 11:18Speaker 01

  So 2003, so you were still doing the lawyering?

• 11:21Rich Roll?

  Yeah, yeah, I mean, I lawyered, I mean, I was slowly kind of weaning myself off of the law up until 2012. The last couple of years, I wasn't doing very much of it, but yeah, I was, I was, I was a lawyer here for the first several years.

• 11:35Speaker 01

  And you'd commute all the way into LA?

• 11:37Rich Roll?

  No, I mean, at that point, I had opted out of the big corporate law firm life, and then I had a variety of different iterations, like I was, I was a solo practitioner, and then I had a couple of partners for a while, and then I had a different partner. I had an office in Beverly Hills for a while, I had an office in Santa Monica, and then I just worked out of the house on and off as well, so.

• 12:00Rich Roll?

  But also, you know, in those iterations, like, I didn't really have a boss, so I had more flexibility, so it wasn't like the nine to five type of commute. But there are people that live around here that, that, that commute downtown every day, like, I don't know how they do that, because we live pretty far out there.

• 12:14Speaker 01

  How, how far away is downtown from here?

• 12:16Rich Roll?

  We, it depends, it's all about traffic, as you know. It can be two hours, or it can be 45 minutes, depending. But our eldest daughter, she's a sophomore in high school, she goes to a high school that's east of downtown now, and the commute is just too onerous, so we have an apartment that we rent in downtown, and my wife and I split the week staying down there with her, and we're homeschooling the other one.

• 12:39Speaker 01

  Good for you. I think that's the way to go.

• 12:42Rich Roll?

  Both of them were, have been homeschooled on and off, and I know you have lots of ideas and thoughts about education, specifically college and all of that. I think we've talked about that before.

• 12:52Speaker 01

  Yeah, although I'm, I'm just curious, as I say, like, probably the main question you're asked about this is the socialization, because obviously, homeschooling, she's going to learn more from you than in some crappy high school, but in terms of friends and socialization, does she get that?

• 13:06Rich Roll?

  Yeah, I mean, that's something that comes up all the time, and that, that's something I worry about the least, because our house is like... It's like a functioning studio. There's just people here all the time, like all different kinds of interesting people. So in terms of like, social stimulus, like, that's the least of my worries. I do get concerned occasionally about, you know, basically pure academics.

• 13:27Speaker 01

  Oh, no, I want to get worried about that. How much do you remember from high school?

• 13:31Rich Roll?

  I know. It is, it's basically just my, the programming of my upbringing that kicks up and creates resistance around it.

• 13:39Speaker 01

  Like, I always ask people, okay, I've even asked this to people who like majored in college in like, European history. And I say, okay, when was Charlemagne born? And this is the most, this is the guy who united Europe or whatever, is the first great king of Europe. And probably 95%, and by the way, we've studied it, it's been in textbooks every year since like, sixth grade. And if you majored in European history, you should definitely know it. But 95%, most, I would say almost 100% don't get it right within 500 years.

• 14:11Rich Roll?

  Right. I definitely could not answer that.

• 14:14Speaker 01

  I don't even really remember it right now. And I've asked, I've even written about it, and I've asked it a million times, but I think it was around 754, give or take. But people will say 1400, 1300, I won't, no. And, and I'm like, okay, well, what else have we learned in school every single year? There's nothing else. I took French for five years. I can't say anything other than bonjour, and I can't even count, I can't even count to 10. And I took it for five years, including in college.

• 14:37Rich Roll?

  Right. What we do need to do, though, is reconfigure the priorities of education around learning how to learn, and learning how to make decisions, and learning how to interact with people, like, life skills that transcend pure memorization. I mean, you were looking at Shane Paris's book here on, sitting on the table, he was in here the other day, and his whole thing about mental models was grown, was born out of this realization that nobody had ever taught him about the methodology of making good decisions. Like, it's just, there's no course in business school, or in college, or in high school about that. And yet, that's something that all of us need to do a zillion times every single day.

• 15:18Speaker 01

  Yeah, not only make decisions, but avoid the biases that are like, almost biologically built into our brains to prevent us from making good decisions. You know, and from an evolutionary point of view, there was a reason for it. Like, if you heard, if you were walking by a bush, and you hear this rustling, You would start running because for good reason. Maybe there's only a 1% chance of a lion and a 99.999% chance it's you just wind through the bushes, but you can't take the chance. So you just run. But we end up making, but we're staring at a screen all day now and we're getting those same instincts. And so we're making decisions based on those same instincts. There's no lion in the, in the computer, but like if a stock goes down a little bit and you're

• 16:03Speaker 01

  looking at the stock market, or if someone sends you an email you don't like, you get that same thing like, I'm gonna just kill somebody or run. And, and you don't know that these are just biases that have been there for a million years.

• 16:15Rich Roll?

  Yeah. Yeah. I mean, it's, it's certainly true. And I've been victim to that many times.

• 16:21Speaker 01

  We all are. We can't help it. Like something in your body or mind is reacting to something in a visceral way. And so if you lean into that, there usually is some creative output that you could produce. So I remember one time, this is a crazy little experiment I did. I, I, I wanted to play around with what are formats to write an article. So everybody just writes and posts it on LinkedIn or their blog and they write a little, you know, 10 reasons to do this or whatever. And so I wanted to come up with, I've been playing around for 20 years, different formats of writing. So I said, I want to do something I never did before. And Donald Trump had just tweeted, I'm gonna buy Greenland.

• 17:04Rich Roll?

  Right.

• 17:04Speaker 01

  And I'm thinking to myself, that's really weird. Like, I didn't even know you could buy a country. And so I figured, okay, let's, that, something about this feels weird, of course.

• 17:15Rich Roll?

  Right.

• 17:16Speaker 01

  And then, and then the president of Denmark, or I don't know, the leader, prime minister of Denmark, he tweets back, it's not for sale. And this is like the weirdest auction I've ever seen on the planet. Like, the president of the United States like wants to buy this massive piece of land. And I didn't even know Denmark owned Greenland. And he's like, it's not for sale. So that also is a weird comment. Like, why did he?

• 17:37Rich Roll?

  Followed by the ultimate troll when Trump tweeted that picture of one of his hotels. Like, did you see that?

• 17:42Speaker 01

  Oh, no.

• 17:43Rich Roll?

  He basically tweeted like, I definitely won't do this. And it was a picture of like a Trump. Top tower like on a on a barren like Greenland landscape.

• 17:53Speaker 01

  That that's so funny that he that he did that. And so I'm thinking, but I didn't even see that, which would have definitely set me off. But just these two world leaders like bantering in this way like this about, you know, people live there. You know, it's this huge piece of land. There's all these natural resources. Where, what, how did Denmark end up owning Greenland? Is it from like Eric the Red a thousand years ago? Like, what is going on here? And so I started to research it and I thought, okay, there's some weird things going on with Greenland that I didn't know about. So I learned, I learned a lot about Greenland. And then instead of just writing an article, I had never done a Kickstarter before. So I decided to do a Kickstarter, which, so I said, okay, I'm going to raise a hundred million dollars so I could buy Greenland.

• 18:35Speaker 01

  And I wrote all, and instead of writing an article, I wrote just all the reasons why I want to buy Greenland, why people should let me buy it as opposed to Trump or some other country. And, and then I had, you know, with Kickstarter, you have to put all the rewards. Like, so I said, okay, fifty dollars, you could be a citizen. A hundred dollars, I'll make you an Earl. A thousand dollars, you could be a duke. And I get carving out all this like acreage for people. And, and, and then I was able to list, though, all the reasons why I thought this was interesting. Like, there's a lot, all these rare earth minerals. And there's a company called Greenland Natural Resources, which is actually a hundred percent owned by China.

• 19:08Rich Roll?

  Yeah, it's China.

• 19:09Speaker 01

  Yeah. So this is all, again, another weird, China now is entering the picture.

• 19:12Rich Roll?

  Right.

• 19:13Speaker 01

  And so there's all these weird things I didn't know. I didn't know Kickstarter. And, and, and so this article, quote unquote, that I had now published on Kickstarter versus a normal place was starting to get shared everywhere. And so that was interesting for me. And then Kickstarter shut it down. And so they shut it down because I'm obviously not, people started donating money.

• 19:33Rich Roll?

  Right.

• 19:33Speaker 01

  And Kickstarter and then GoFundMe, the same experience. They shut me down because I'm obviously not going to raise a hundred million. So they, and they're on, they have to pay all the chargebacks to the credit card companies. So it could be a big money loser for them. So they just shut it down. But then I had a second story, which is I was just shut down by Kickstarter and GoFundMe. And so the whole thing is, here's a little experiment. And I gained a huge amount. From it without any cost to me. So I learned all this stuff about Greenland. I learned about Kickstarter. I'd never done a Kickstarter before. So suddenly now I knew how to do a Kickstarter. I spent some time studying best crowdfunding practices and I learned about Kickstarter. And, uh, and then I learned this new format. I could write articles in, which was weird.

• 20:16Speaker 01

  And then I had a second story on top of it, which is that they censored me and here's what happened. So just that small impulse allowed me to experiment in ways that I wouldn't have been able to otherwise. And learn a whole bunch of things that now I can do a Kickstarter or now I can speak intelligently about buying Greenland or whatever.

• 20:33Rich Roll?

  And it's super funny.

• 20:35Speaker 01

  Yeah, and it's funny. Right.

• 20:36Rich Roll?

  Wait, what? Like, first of all, you know, can a country buy another country? Yes or no? Can an individual buy a country? And what's interesting is that you got shut down, not on the merits of what you were attempting to do, but on kind of a side technicality, which was probably motivated just by extreme discomfort.

• 20:54Speaker 01

  Right.

• 20:55Rich Roll?

  At what was going on and they're them trying to figure out like, we got to find a way somehow to shut this down.

• 20:59Speaker 01

  Yeah, and people were like, uh, sending money in, like they were like wiring money in. And so.

• 21:04Rich Roll?

  And the sheer audacity of the whole thing.

• 21:07Speaker 01

  Yeah.

• 21:07Rich Roll?

  It, it, it's not dissimilar from, uh, and I know you've talked about this as well. Richard Branson saying, saying, give me, you know, going to Boeing and saying, give me an airplane.

• 21:18Speaker 01

  Yeah, no, that's a great example.

• 21:19Rich Roll?

  It's so ridiculous that they would do that, but there's something about where naivete meets audacity, you know, an audacious, you know, dream and then some steps are taken. That that's how anything amazing is created.

• 21:33Speaker 01

  Well, there's so many layers of you can't do this involved in any creative act. Because if there, if there, if people weren't telling, if, if people weren't saying, Rich, you can't do this, then thousands of other people probably would have done it by now. So it's, it's, it's kind of finding where people are saying, you can't do this. But when you ask yourself why there's no real reason, might as well try it.

• 21:57Rich Roll?

  Right.

• 21:58Speaker 01

  So like with this, there's no reason why I couldn't start a Kickstarter, raise a hundred million dollars to buy Greenland. And I've learned something and, uh, you know, all the times like people say, oh, well, you know, you can't start a podcast. Have you ever done interviews before or a radio show? Like, leave it to the professionals. No, I think I can do it. Like, why can't I do it? And, uh, you know. I'll tell you another just quick experiment. It's not as interesting as Richard Branson. Richard Branson is really an interesting example because this is a 27 year old guy who was a magazine publisher and had no experience with anything relating to airlines. British Airways had a monopoly in England on airlines.

• 22:40Speaker 01

  Heathrow only dealt with British Airways and Richard Branson didn't have money. And he simply calls up Boeing and asks to borrow a plane. They give it to him. I mean, the details, I'm skipping over the details. They just lend him a plane for a year. Heathrow's like, yeah, you could use this one landing strip. We don't really use that much. Same with JFK. And suddenly he has a plane going back and forth. Like, you know, that every, I'm sure at every step of the way, people were saying to him, are you insane? And but what does it hurt to ask? And then, of course, there's subtleties, there's skills to asking. And how did he ask? And all these things that he used skills learned from being a music magazine publisher. But still, it's this combination of skills with audacity, with, you know, like, why can't

• 23:25Speaker 01

  I? And allows you to go forward on so many different, different things.

• 23:30Rich Roll?

  Right. I think both those examples, Greenland and the Richard Branson example are illustrative of, of both of these books. They, well, the, the book that you have out now, Think Like a Billionaire, and the book that you have coming out next year called Skip the Line, like, there are, there are lessons in both of those examples that could be pulled from both or either of those books.

• 23:52Speaker 01

  Oh, yeah, absolutely. Because let's say, well, let me ask you, when you were starting to run in marathons and then ultra marathons and Iron Man things, and you were, you were in your mid 40s, I bet you there were a lot of people saying to you, Rich, maybe you should just stick with a 6K or whatever.

• 24:10Rich Roll?

  Yeah, plenty of that, plenty of that. But I look at it as sort of the, the frog in the warm water that's coming to a boil slowly. Like, there is an incremental, like, sort of compounding path that you can take towards, towards like an athletic goal. That's different from, I mean, I guess I did skip the line in that I didn't do all that little stuff and I went right to like ultra distance and didn't pay my dues or didn't, didn't take that traditional route in that regard.

• 24:37Speaker 01

  Let's not forget, you didn't start with 5Ks, then 10Ks.

• 24:40Rich Roll?

  But I was an athlete, like, I can, I mean, look, I can minimize it. But. Yeah, I guess for somebody not steeped in this world, it does sound like a little insane and ridiculous.

• 24:52Speaker 01

  It was insane, Rich. Like, you weren't an athlete then, right?

• 24:57Rich Roll?

  No, I had a past as an athlete.

• 24:59Speaker 01

  Right, in high school.

• 25:00Rich Roll?

  But logically, yeah, like, rationally on paper, like, it didn't make sense.

• 25:04Speaker 01

  And so, and yet, look what happens. You ran, you know, I don't know the exact, the ultra iron, whatever, on every island of Hawaii, you know, one day at a time. You did these incredible feats that I'm sure many people, every step of the way, kept telling you, "You can't," but that's what put you on the other side, where you, suddenly, if you go past enough of, "You can't do this," then suddenly, you're the only one doing it. And so, you were the only one in the world who had the kind of resources and set of experiences and set of talents that you had, where you were running in all these races, but you were also, you know, going towards this vegan lifestyle, you had the experience of being a lawyer, so you were able to, you know, you had a better capability of writing about all these experiences than most people would.

• 25:48Speaker 01

  So, you were able to combine them all into being the only Rich Roll out there, doing these events, books, podcasts. You were, there's no one who can compete.

• 25:56Rich Roll?

  Yeah, well, I think it's an example of having all of these skills in a variety of disciplines that I tried over the years that weren't necessarily matched up with, like, my ultimate talents, and certainly not my passion or a sense of purpose, that when they finally found the right outlet, it all congealed to create, you know, an amazing result. In the same way that, you know, if somebody was to say to you, like, "You don't have the credentials to be a podcast host," but many years ago, you did your 3:00 AM show, you learned how to talk to people, you learned how to create something that's entertaining, you are doing stand-up comedy, like, you've done, you've been writing, you've, all of

• 26:38Rich Roll?

  these other areas, like, all contribute to your ability to sit behind a microphone and be engaging and be entertaining and be curious, all these skills that you've developed over the course of a lifetime. I mean, I would say, similarly, I took a million depositions as a lawyer. I learned how to ask questions, and I think that- My, my, the, my true skillset as a podcaster was developed through sitting in thousands and thousands of AA meetings, listening to people tell their stories and learning how to tell my own story. That was my training ground for being a public speaker and being a podcast host. You learn how to be empathetic, you learn how to listen, you develop this, this, this great capacity for compassion for the human condition that I think lends

• 27:21Rich Roll?

  itself towards creating a safe and, and interesting environment to explore those very themes with another person sitting across from you.

• 27:29Speaker 01

  Yeah, I think, I think that's so interesting because I think that does come across, like your compassion for your guests comes across so much in your podcast, I think because of your experiences. And, you know, I always wonder about this idea that vulnerability, like the kind you experience in AA, the kind you experience in, or one should experience in, in writing and maybe all forms of art, vulnerability sort of buys freedom. Like, when you're vulnerable, when you are able to admit to what can go wrong, what has gone wrong with you in the past, the mistakes you've made, now you're free. Like, nobody can say, well, you can't say this, you've done this. And I, yeah, I said that. I'm

• 28:11Speaker 01

  an idiot a lot of the time. Bring it on and you're free. You don't have to deal with people saying, well, Rich, you can't talk about health. You had this and this happened to you in your twenties. All right. Yeah. Read my book. It's in it.

• 28:27Rich Roll?

  I already told you about that.

• 28:28Speaker 01

  Yeah. So you're free from, from all that stuff. And the, and the more vulnerable, like, how can people, you know, attack that? Like, can't say, well, now you're not allowed to write about this because you experienced this. No, there's no rules. And, and yeah, I'm just being authentic and that allows me to be as creative as I want in this area. I'm creative even about my mistakes.

• 28:48Rich Roll?

  Well, your specific strain of authentic vulnerability was really a tipping point in your creative career. Like, when you finally made this decision that you were going to be honest and write about it, write about your life and your experiences in a very transparent way, I'm sure there was a lot of fear that preceded that. But when you mustered up the, the courage to do that. That's really when things change for you.

• 29:12Speaker 01

  Oh, yeah, completely. And to the point that now, I don't even, like, if I'm writing something, I don't publish it unless I'm afraid of what people are going to think of me. And I don't try to say something that's gonna, I just ask myself at the end, right before I hit publish, is this, am I really saying something new and unique here? Because I don't want to say something that everyone else has said. Or am I saying something where I'm really afraid, oh, no, what is, what are X, Y, and Z gonna think of me? What are these people gonna think of me? What are my friends gonna think of me? What are my readers going to think of me? So I, I, I always have to double check myself because if you're not afraid of what you're creating, there's a chance then that, okay, everybody else has done it because they weren't

• 29:53Speaker 01

  afraid either. And so there's gotta be some resistance somehow that you get over. Like even something I wrote recently, I, I was legitimately afraid, well, is this gonna shed a new light on everything I've written for the past 10 years because I'm admitting to this other thing? And I was, I was nervous, incorrectly so, but that's okay. That's, that's, that's how you learn, is, is getting over that every time.

• 30:17Rich Roll?

  Yeah, when I wrote, I think I've probably told you this previously, but when I wrote Finding Ultra, like, I really had to get into the mindset of, of writing in my private journal that no one was ever gonna read. Like, I had to get comfortable communicating things about my life that I'm ashamed of and that I'm embarrassed about. And I remember when I sent the manuscript to my editor at the publisher, I, I looked at my wife and I just, I said, I hope I'm making the right decision. Like, this could be the worst decision I've ever made. But I knew intuitively that the value of the book would be directly correlated to the extent to which I was willing to be vulnerable. Because why do it otherwise? You know, and I think-

• 31:02Rich Roll?

  You know, my book Finding Ultra is it's an addiction recovery memoir. It's also like this sports story and it's also kind of like a health and wellness primer. But but ultimately, it could be categorized as a as a sports memoir. And like, I hate sports memoirs because they're all they're usually written by athletes in the twilight of their career and they're intended to kind of create a halo effect and and perhaps buy them a couple of years in the spotlight. And that's why they're not good because they're inherently less than honest. And I've never won a race. It's not like I went to the Olympics or anything like that. Like, why should anyone care what I have to say about this? The only reason that this the only way that this is going to be compelling is if I, you

• 31:44Rich Roll?

  know, take my specific experiences and try to connect with something more universal about the human condition. And that can only come through, you know, a profound level of honesty.

• 31:54Speaker 01

  Yeah, and that and that happened. You created something very unique, which was this sort of combination of kind of a sobriety memoir, health and wellness, athletic memoir, plus a reinvention memoir. So you were in your 40s, a time when people think, well, my knees are starting to hurt. Maybe I shouldn't run marathons anymore. There's a lot of people are thinking like this of slowing down and you were literally speeding up at that point. And I think you gave permission to to for people who were reading it to say, oh, yeah, he stopped being a lawyer to do this. He stopped, you know, he he became sober and then this started happening. He went vegan, this started happening. He's in his 40s and he's doing all these athletic competitions.

• 32:36Speaker 01

  It's sort of like you gave permission, not only for other people to be equally vulnerable, and I'm sure you got lots of messages like, man, I was in the same situation as you and so on. And but you also gave people permission to, hey, I could if he could do it, I could run a marathon or do something incredible when I'm 45 that I never thought I could do before. And I think that's something like I'm curious now, like when you're thinking that that was a very pivotal story for you, right? And it's an iconic story like I'm I was you were you were saying essentially, I was down and out, then this happened, and then I became a superhero. So it's like this iconic story. Do you feel do you ever feel like? Tied to that story, like you have to keep repeating it or find a new story?

• 33:19Speaker 01

  Do you ever do you ever grapple with the whole that story now has over you versus what the whole you originally had on that story?

• 33:26Rich Roll?

  Yeah, 100% and I've worked really hard to kind of transcend that a little bit. Certainly, I think, I think when the book came out, it was sort of characterized as a book about running, which it isn't. It's not about becoming an ultra marathon or it's very much a choose yourself story.

• 33:42Speaker 01

  Absolutely.

• 33:43Rich Roll?

  It's about the inherent power that we all have within ourselves to, you know, basically shift the trajectory of our life, even if we find ourselves in our 40s or in our later years, that that inherent capacity lives within all of us to tap into, you know, a more, a deeper reservoir of human potential in whatever way, you know, feels right to you. And I think it took, it took a long time for that message to kind of percolate out of what was considered to be a running book. But then, yeah, I felt, I wouldn't say trapped, I think that's too strong of a word, but, you know, this sense of being like, oh, you're the vegan ultra athlete. Like, yeah, that's something that I did, but it's only one aspect of who I am.

• 34:28Rich Roll?

  And the podcast very much is about, it's not about me, it's about my guests. It's about, it's about the next chapter. If the, if the book was going to have, you know, an epilogue, like, okay, now what? Like, I, I leveraged some tools to grow and manifested this thing that I talk about in this book, but that growth continues. That's not the end of the story. I want to continue to grow. If I could make these changes, what other areas in my life am I currently blind to? So let's go on a journey to explore that with the smartest, most interesting people that I can find. And that has nothing to do with my story and everything about, you know, the wisdom that's. Available in the world.

• 35:09Speaker 01

  And so now you've interviewed hundreds of really amazing guests, a lot of them kind of athletic, but not all of them, you know, a lot of it's about wellness, but again, not all of it, it's all people who have captivated you or interested you for various reasons. And I'm, I'm, I'm, let me ask you this, so I'm debating this. So I've also interviewed hundreds and hundreds of my heroes and, you know, authors who are, you know, passing through the city, so I get to interview them and so on. And I've interviewed many, you know, people I've just always looked up to. And I'm starting to wonder, okay, after 500 of those, maybe sometimes I want to just say what I think about things rather than

• 35:53Speaker 01

  just always interview people. And so I'm kind of going forth on that of mixing that up a little, not completely, but just mixing it up. So it's not, you know, there's 2 million interview podcasts out there now. And we were just talking about this earlier, when we were in 2014, there was like 100 interview podcasts, and now there's literally 2 million. I'm not even exaggerating it. And, okay, and we've also interviewed everybody. And so now we haven't interviewed the whole planet, but we've interviewed a lot of people. So people start repeating things or saying similar things. And then, but I'm sure your audience, they're listening to you for a reason, and maybe they want to start hearing more of what you have to say about a topic. And I wonder if you've ever debated doing kind of more solo stuff?

• 36:34Rich Roll?

  Yeah, I mean, a couple of thoughts. First of all, both of us have been doing this for a while. I started mine in late 2012. You've done more episodes than me, but I started a little bit ahead of you. There's been a lot of overlap in our guests. We've been on similar journeys. Indeed, when we started, it was not a competitive environment. Both our shows went right to the top and kind of stayed there. And in the intervening years, this medium has been adopted in a very mainstream way. So the ecosystem has matured tremendously around us. We were both lucky enough to grab a little piece of real estate and hold on to it. But, you know, I certainly wouldn't want to be somebody starting an interview based podcast now. I think it would be very, very difficult

• 37:19Rich Roll?

  to do that. So I'm extremely grateful to be in the position that I'm in, and I'm sure you feel the same way. But

• 37:28Rich Roll?

  You know, here we are, and I'm interested in your thoughts, too. I'm going to throw this back to you. Like, what is the State of Union with this medium? And as somebody who thinks about things in a counterintuitive way and with a different lens, like, what is the future of this? And I'll continue to answer your question and allow you to answer that when I'm done. I think that, you know, I had Kamal Ravikant over here yesterday, your good friend, and we were talking, and we were talking about your show. And I said to Kamal, I go, I tune into James. Like, James has lots of interesting people on his show, but I want to hear James. Like, I'm fascinated by your lens, your perspective on the world, and you're the reason that I tune in.

• 38:08Rich Roll?

  So I think that that is a smart and appropriate pivot for you to start to have more standalone episodes with just your reflections and your thoughts. In my own case, I have thought about that. The hardest part of this whole podcast thing for me is doing the introductions. Like, when I'm alone, talking into a microphone, I'm so up in my head, and it feels so unnatural. So the idea that I would sit down and just deliver a monologue spontaneously from whole cloth, even if I had an outline, that scares me, and I feel like that is a skill that I haven't yet honed, and perhaps that's a reason to attempt it.

• 38:45Speaker 01

  Or there's a way to experiment in the sense that, let's say, you have just someone sitting here who's listening, and occasionally, maybe, instead of, like, in an interview, it's, let's say, 50/50, but let's say, in this case...

• 39:00Rich Roll?

  You need a foil.

• 39:01Speaker 01

  Yeah, a foil. You need someone who you're just going to throw things against, and if something doesn't quite stick, they'll inform you of it.

• 39:06Rich Roll?

  Yeah, like, more than like, you know, a co-host, but somebody who, you know, can like, match your wits and push you to deliver a monologue here or there.

• 39:18Speaker 01

  Yeah, like, let's say there's...

• 39:19Rich Roll?

  I mean, go ahead, Simon.

• 39:20Speaker 01

  Well, let's say there's an issue that, you know, triggered that emotional impulse for you this week. So, something happened that bothered you, and you just wanted to, and you wanted to talk about it, but not necessarily the issue, but even more globally, like, what does this mean for either the world, or people, or what did I learn from this, or the economy, or whatever? And you just start ranting on it.

• 39:44Rich Roll?

  Yeah. And... I do have a little bit of an insecurity around it, I think.

• 39:51Rich Roll?

  Here's an example. So last year, we did our first like live podcast event. We booked this big theater and we sold it out. It was like 1,200 seats.

• 40:00Speaker 01

  That's great.

• 40:00Rich Roll?

  And the idea was to do a live podcast and but also produce a show that was very, you know, that kind of transcended this podcast format to create an entertaining experience for people. I had my sons play music and then in queue perform some live poetry. And then I did a live podcast with Paul Hawken, who's like this legendary environmentalist. And I conducted that podcast very much as if he was sitting across from me right now. Like, I kind of maintained that format. And after the show was over, I basically went, you know, out into the hallway and just talked to people for as long as they wanted to talk to me. And I was there for hours and hours and hours. And I realized in retrospect, oh,

• 40:42Rich Roll?

  these people, like, I think they're coming to see Paul Hawken, you know? And, and I realized like, oh, they, they're, they're, they are coming to see me, which makes me uncomfortable. Like, I doesn't feel like I, because I have profound imposter syndrome. Like, I can't imagine why anyone would want to come and see me. But, so the growth for me is in, is in owning that and, and, and, and living up to that on some level that, that, you know, I have had certain life experiences that have value and that there is something interesting about sharing, you know, my perspective.

• 41:15Speaker 01

  Yeah. Or what if you even went on Twitter beforehand and you said, listen, I'm gonna try this solo episode thing, but give me some fuel. Ask me a bunch of questions. And then you pick the four or five that you like the best and can even just do a 20 minute episode or, or attach a story from your life to each question along with the answer and or your answer. And that's an episode.

• 41:37Rich Roll?

  Right. Yeah, I think I'll probably try that. I think I'm, I'm, I wouldn't say I'm in a rut, but I had, we have like a routine now. And like, I know how it goes and it's working. And, and you're somebody who's coming in as, you know, like this disruptive force who's like always, you know, got the waiter pads and you're writing down the 10 ideas every day and you're like trying to buy Greenland and you're doing all this crazy stuff. And what I love and appreciate it, appreciate, appreciate about it, isn't just the, the kind of Courage to do it. It's your relationship with the outcome, I feel, is very healthy. Like, you're not, it's not about whether it works or not. You're just doing it.

• 42:14Speaker 01

  Right, because here's what I always think is that something's going to work. Some outcome will exist that I like, but it doesn't have to be the outcome of whatever it is I'm doing that day. So I'm doing something, let's say, today, or tomorrow, or the next day. I'm doing something to try something new, or try an experiment, or write something. Eventually, the outcome might be bad. Like, for instance, this Greenland Kickstarter thing, and again, this is a silly example, but that was essentially a failure. I didn't raise $100 million to buy Greenland. Kickstarter shut me down, and it was fast enough. It didn't really get as widely spread as I, as a successful outcome would have been. But

• 42:57Speaker 01

  it was interesting. I learned something. I learned a whole bunch of things, and then you move on. Because-

• 43:02Rich Roll?

  And you have this amazing story.

• 43:04Speaker 01

  Yeah, I have an amazing story, and now I have knowledge, okay, here's how to do a Kickstarter if I want to try something else. And so now I can do the next thing, which might be just as crazy or not, and the outcome may be good, maybe bad. Eventually, there'll be, some outcomes will be better than others, but whether the outcome is bad or good, I'm learning from each thing.

• 43:23Rich Roll?

  Right.

• 43:32Rich Roll?

  You've canonized this as the 10,000 experiments rule. We all talk about the 10,000 hour rule. You're like, that's nonsense. Let's focus on 10,000 experiments instead.

• 43:43Speaker 01

  Yeah, because I, so the 10,000 hour rule, which, you know, was developed by a great guy, Professor Anders Ericsson, he basically determined, if you devote yourself to 10,000 hours of what he calls deliberate practice at any field, you'll be among the best in the world at that field. And this was written about by Malcolm Gladwell in the book, Outliers, and it kind of became a popular phrase after that. I just couldn't wrap my head around it, though, because I feel like I've gotten good at a bunch of different things, and I don't think I've spent 10,000 hours at them. And I couldn't, and for some things, I couldn't figure out what does he mean by 10,000 hours. Like, I understand with, let's say you're, you know- Doing a golf putt.

• 44:27Speaker 01

  I can understand practicing that for 10,000 hours and you'll get better at golf putting. But for something like writing, what does it mean to spend 10,000 hours writing? Like, there's so many nuances in a creative field. And it's not repetitive. It's not like I can get a coach, after I write a sentence, I can get a coach to say, "Well, that sentence could have been better." So I didn't really, and I would write to him, and he's always very smart and he was always very friendly to respond. And I've read all these different theories, like, can I borrow hours from this other activity? So I was trying to get good at stand-up comedy. I started this, it's a random thing, I got passionate about it about five years ago, started going up on stage. And I was trying to figure out, can I borrow from my 10,000 hours public speaking and

• 45:11Speaker 01

  some hours from my writing and some hours from just, I don't know, being funny? Or how does it work?

• 45:19Rich Roll?

  The transferability of these skills in a variety of disciplines, can you aggregate them to come up with your 10,000 hours?

• 45:26Speaker 01

  Yeah, or at least give me some head start. And he kept writing about, "Well, what's the metric you're judging yourself with?" And there's really no metric. Like, how do you determine if something, for instance, is good writing or not? Is it book sales? No. Is it if your favorite professor likes it? No. It's hard, for creative efforts, it's hard to have a metric of success. For many, for sales ability, for business ability, there's so many like other factors like luck, environment, the people you're dealing with. It's hard to measure your success with these 10,000 hours. And it was confusing talking to him. So then I figured, well, maybe there are, and then the other thing that concerned me was, well, what if you take training methods now and go back to the 1920s?

• 46:10Speaker 01

  So for instance, if someone took people who, coaches who trained for marathons and took those same techniques back to the 1920s when coaching techniques were so, were not as advanced. Would it be then 100 hours to be the best in the world? You know, the hours change depending on how advanced the field is. So more things kept coming up that I didn't really understand. And that's when I started thinking of another model completely to measure my own success. And then to accelerate my own learning in different fields. And so I was very excited about that because it basically took me two or three years to be a good, solid professional investor, took me two years to achieve a level I wanted.

• 46:55Speaker 01

  And let's say a game like chess, which is normally a hard skill, or computer programming, which is a hard skill. And then with standup comedy also, I didn't, you know, I was 48 years old at the time. I'm 52 now. I didn't want to go 10,000 hours or 20 years to get good at something. It doesn't, I don't want to be on stage when I'm 68 years old trying to make a bunch of strangers laugh. Like it feels silly to me. I just wanted to get good at it now. I wanted to literally skip the line. Everybody kept telling me, don't think you can skip the line. Like we've all worked hard.

• 47:25Rich Roll?

  Especially in standup comedy, like they're very, you know, respect your elders. And that's very much a, you know, you got to grind and pay your dues.

• 47:33Speaker 01

  Yeah, that's what people tell me.

• 47:34Rich Roll?

  Every standup comedian will be like, you got to go up there and bomb a thousand times, you know, and just keep doing it and keep doing it and keep doing it. And in 10 years, you'll be good.

• 47:43Speaker 01

  Yeah, 10, 10 best case is what they would say.

• 47:46Rich Roll?

  And here you are, like you start basically telling jokes on the subway, right?

• 47:50Speaker 01

  Yeah.

• 47:51Rich Roll?

  And now you're headlining.

• 47:52Speaker 01

  Right.

• 47:53Rich Roll?

  What is the time period?

• 47:54Speaker 01

  It's basically about five years. But like four years since I started taking it super seriously, where I would go up two or three times a week and more recently, you know, up to 10 times a week. So, but yeah, I had to construct, I had to really be very analytical about it. And I would deconstruct every comedian's axle. I would understand what they were doing. And then I would explain it back to them and they were like, huh, I never thought of it like that, which is fine, like they were, they have their process. But then I started constructing experiments I can do to basically accelerate my learning. And I found every experiment really. Changed the way I would do comedy. So I would start really, people would see me from

• 48:36Speaker 01

  one month to the next and they're like, boy, when did you start doing X, Y, or Z? And I'm like, after this experiment I did where I saw these other things weren't working. And sometimes the experiments are very simple, like between jokes, what if you just lean back against the wall and look up at the ceiling for three seconds or for a half a second? Like, so just even an experiment like that, because there's this feeling on stage that you have to spit everything out as quickly as possible. Or, you know, you mentioned one experiment I did, I went on this, I wanted to tighten up my one liner. So I went on the subway and did stand up comedy on the crowded subway cars where nobody wants to hear you tell jokes, nobody likes you, nobody is, in the best case, I can't

• 49:21Rich Roll?

  The bar towards getting a laugh is very high.

• 49:23Speaker 01

  Right. They're not, they didn't just pay a cover charge to see a comedian, they just want to get home. Like, you're bothering them at that point. And they're not drinking. So they want to drink.

• 49:33Rich Roll?

  Some of them might be.

• 49:34Speaker 01

  Right. Some of them might be. And most of them want to drink. And then this person just gets out of the car and starts telling jokes straight at them. And it was, it's very difficult, but that.

• 49:45Rich Roll?

  Did you get some laughs, though?

• 49:47Speaker 01

  I did, yeah. Oddly, I would get on and I would say like, um, the one thing that got the most laughs is like, I was, I, is this, was this the six and a half stop? Like, is this, is this the train to Hogwarts? And so kids would laugh at that. And then I did another one. Hey, I ordered an Uber pool, but they sent me this subway car. So that got some laughs. Those are like the main two things that got laughs.

• 50:11Rich Roll?

  You have to be so comfortable with your vulnerability, though.

• 50:15Speaker 01

  But I wasn't.

• 50:16Rich Roll?

  It's like.

• 50:17Speaker 01

  I was with a friend of mine and this person brought on a video camera just so I could study it later. And I got on and I looked around, I'm like, forget it, we just wasted our time, Mike. You could just put the camera away. And I was like, and then I said, on second thought, just turn it on and let's just wait a second. So my friend turned on the video camera and then I just went off. So it just, I wasn't, I just went without thinking. And, and, you know, sometimes people will laugh and sometimes people were like, you know, boo, like, get out of here. So, but that happens.

• 50:48Rich Roll?

  You gotta be okay with either one, right?

• 50:50Speaker 01

  Yeah, you gotta be okay with either one.

• 50:51Rich Roll?

  I mean, that's the difference between true vulnerability and what I see a lot of now, which is, I call it performative vulnerability. It's sort of like, now it's cool to be vulnerable all of a sudden. And you see a lot of people using it in a very, I feel like, disingenuous way. Like, oh, like, when you're vulnerable online, that's how you get people interested in what you're doing, so I'm gonna do this. And it's like this weird, like, fake vulnerability.

• 51:21Speaker 01

  Yeah, and I see that, it's almost like you can't, if you pick up a recent self-help book, or any, almost any recent self-help book, and I'm not gonna throw the whole industry under the bus, but a lot of recent self-help books, you can't even, the author always starts off like, well, I was in my darkest moment, and then XYZ happened, and I started writing in my gratitude journal, and whatever, and then everything became better. And it's like, that's like a bad, and then even in Silicon Valley, it's like a badge of honor, like, yeah, I failed at my first startup, and blah, blah, blah, and then now, now I'm ready. And, yeah, I agree, I think it's a way to kind of almost buy, it's almost too transactional, the vulnerability.

• 52:02Rich Roll?

  Right, yeah, transactional, I think, is a good word. And hand in hand with that, I get, I'm sure you do too, like, I get all the galleys in the mail now, when you host a podcast, like, suddenly, books just arrive at your house all the time, like, I get like, six books a week in the mail. And generally, they'll be, you know, the upcoming self-help books, right? So I have so many self-help books being delivered on the regular here, that it's made me very cynical about all of it. You know, I just look at this, and I'm like, they're all, and I can't possibly read all of them, but maybe you can, but I just kind of page through them, and I'm like, they just feel like different flavors of the same thing, and it's made me, like, less interested in all of that.

• 52:47Speaker 01

  Yeah, that's why I think, well, look at, you know, for instance, Finding Ultra, or in my upcoming, you know, Skip the Line, I think about this. What are, forget about all self-help. What are my real stories, for better or for worse, and what did I learn from them? And what can I extrapolate? The extrapolation is what gives it the self-help categorization. Like, okay, I did this, this, and this. So that's a formula. But I always say I'm not giving advice. This is what worked for me specifically, but maybe it's broad enough, it could work for others. And I always want to make sure it's, it's just not like, there's a, not only is there a self-help genre, but they all kind of recommend the same thing.

• 53:29Speaker 01

  And, and you get this sense they're recommending it without real experience, or they're recommending it so they can start getting speaking gigs, talking about it, because you can make a lot of money talking, you know, motivating companies. And so I always try to make my, make sure I'm saying something really unique. Like this, this 10,000, you know, thinking about learning and the 10,000-hour rule and how I could succeed. Like, you went through this. In your mid-40s, you left a profession and kind of started, or you did start, new professions. And that, a lot of people are going through that, but they always think, well, I'm already 45. How am I gonna learn to be the best or the top 1% of some field so people, so I can make a living at this? Because you need to be in the top 1% roughly to, to make a living and to feed your family.

• 54:14Speaker 01

  And we're going through it just personally and as, and economy. And so, really grappling with that and how I challenged myself to learn different things and how I failed at many things in the, along the way, I had to think, well, what's, what's happening? And that's where I went from the 10,000-hour rule to, am I, can I borrow hours? Or is there like shortcuts or cheat sheets? Or what's actually happening? And you have to really think inside. What happened to me that I can bring out as a story? And I, I feel like you did that too with, with Finding Ultra, was your unique path to saying, hey, at 45, you could still be. A top world-class athlete and do these things and get over these issues and change careers and on and on and on.

• 54:59Rich Roll?

  Yeah, but I think my book was really just a story, whereas you look at these things that have happened in your life and you look at other successful people and you're trying to extrapolate the themes and the lessons and then figure out a way to communicate a path forward through a lens or a path that perhaps has never really been fully articulated. Like the Skip the Line book that you have coming up. Like, I haven't read it yet, but you've told me a little bit about it. And I think it's interesting because it's about this very thing of like, look, we're in a rapidly changing world where we're going to be compelled to have to reinvent ourselves. We're living longer, et cetera. And you don't

• 55:42Rich Roll?

  want to just have to switch gears and figure out a new career later in life and start at the bottom. You're somebody who has had success in a variety of disciplines without really having to do that, without putting in 10,000 hours and somehow found your way into that like top tier, that top 1% of these disciplines. So what was the differentiator here and what can be learned from that experience that could be helpful to other people?

• 56:08Speaker 01

  Yeah, and I think, and look, there's other things too that I've massively failed at. So you sort of learn along the way. I better restrict my failures so I don't lose everything on this failure. So you have to also construct ways to get better at something where you're not risking your entire life. And like you even said earlier, the transition from lawyer to everything else you're doing now, it took a while. Like, people kind of think, oh, well, I'm gonna quit being a lawyer and start being a podcaster and the money's just gonna roll in. It doesn't really work like that for anybody in the world. It's

• 56:48Speaker 01

  a process and it's a process of trying lots of different things. It's a process of transition. It's a process of finding more and more things that you enjoy and that you love doing and that your passions maybe lie. And maybe when you find something you're passionate about, you're able to double down on it enough so that, again, you're not risking too much, but you double down and you see how it works and how it feels. And it's a process.

• 57:14Rich Roll?

  So you've got this book about billionaires, Think Like a Billionaire.

• 57:17Speaker 01

  Yeah.

• 57:17Rich Roll?

  I feel like culturally, we're in a moment where we're fetishizing these people.

• 57:23Speaker 01

  And on both sides.

• 57:25Rich Roll?

  Yeah. Both sides, meaning what?

• 57:27Speaker 01

  Like, some people, you know, you'll see politically, people will say, well, banish all billionaires, or like, somebody in politics said, and this is not, I'm very apolitical, but someone in politics said, you know, billionaires have not earned the money, they took the money. So there's a very kind of almost violent revolutionary backlash against these people who have accumulated this one particular number or more. And on the flip side, you can say, well, these are people, perhaps, who have accumulated certain habits that maybe you'd want to emulate if you wanted success, even if it wasn't success about money. And then you can also say, okay, well, are there benefits to this class of people who have accumulated so much wealth? Are they giving to charity? Are they solving world problems?

• 58:12Speaker 01

  Are they creating impact more than if the money was being used in other ways? And I shouldn't even say being used, because often, money is created. That's something that a lot of people don't understand about the economy. There could be more money next year than there is this year, because people who are innovative use their innovations to create money, seemingly out of thin air. But, you know, if Elon Musk sells more Teslas, and he raises money by having an IPO, and his Tesla goes public, and whatever, money is basically created and put, to some extent, put into his pocket. So it's not like they took, they've created it out of their innovations. But sometimes they're bad guys, and sometimes they're good guys, like anyone else.

• 58:56Rich Roll?

  I mean, there is a sense, I think, that you don't get to that level of wealth and accumulation without stepping on a lot of people and having to do some dastardly things.

• 59:06Speaker 01

  Yeah, I think that's, I think that's kind of the sense, and it's easy to have that sense, because let's say there's a few thousand billionaires, and there's 300 million other people in the US. So we're all allowed to trash this, they're certainly not a minority, just because even though there's just a few thousand of them, they're very, they're people who are very privileged and benefitted. And and they have every advantage in society. And by the way, some of them are really bad people. But some of them are enormously charitable. Like you look at efforts like Bill Gates. And again, I don't know if whether you like Microsoft Windows or not, but you look at Bill Gates, he he has spent hundreds of millions or billions to try to eradicate malaria in Africa. And yeah, you ask yourself, well, if if the money had gone

• 59:51Speaker 01

  to a government instead of Bill Gates, would that government have been able to solve malaria as well? I don't know. I'm not an expert, but it seems like Gates has made a dent on it and nobody else historically has made a dent on it. And and I've I heard one interesting story where Bill Gates gave like a hundred million dollars to a government, just like the US might give a hundred million dollars to the government. Let's, you know, here's aid, solve malaria. And then that particular government was corrupt. The leaders left and the money was just gone, not spent, disappeared, probably into some Swiss account. The leaders moved away and whatever. So the next leader got in and Bill Gates said, OK, I'm going to give you a hundred million again, but now I'm going to have more control over it and see how you spend it and see where it's put.

• 1:00:35Speaker 01

  And he made a dent in eradicating malaria in this particular country. So you you have to look at instances too and see what's what's happening. What are these people doing with the money?

• 1:00:45Rich Roll?

  Right. But isn't Bill Gates more of an outlier in that regard? Like, there's a lot of, you know, there's a lot of guys with, you know, lots of yachts and things like that.

• 1:00:53Speaker 01

  I would say he is an outlier. But there's also, you know, there's thousands of billionaires. So let's even say there's a few hundred outliers who are trying to do charitable things. And by the way, I'm not trying to, really, the purpose was of that book was to say, OK, I've been so bad and such a failure at dealing with money. Maybe I could learn what did they do that I don't do that's I could learn from. So it really had nothing to do with whether they were good or bad. And so I always feel like I'm apologizing a little.

• 1:01:20Rich Roll?

  It's also not about making money. It's about habits and a and a perspective on on life and how they kind of live their day on the daily that that lead them in that direction.

• 1:01:30Speaker 01

  Right. Like, not not a single thing in that book is about, well, this is the kind of investing they did. And this is the kind of companies they would start and here's how they would boss people around. But but just on the the Bill Gates thing, yes, he's probably an outlier, but you do see lots of examples of of charitable things or even, let's say, not charitable, like. You know, Ken Langone, multi-billionaire, started Home Depot. He saw a problem, which is that many people didn't have access to the full range of home improvement tools that they would probably want. And he created Home Depot, it became big, and hundreds and hundreds of thousands of jobs were created. Just, you know, maybe millions of jobs over the 30 years Home Depot's been around.

• 1:02:13Speaker 01

  And, you know, over 100,000 people got very wealthy by being employees of Home Depot. So he created real wealth in society, solved lots of problems. Now, Ken Langone, almost every hospital in New York is named after him because he gives so much to charity. And I don't really know him, so I can't say good or bad. But, again, I ask myself, well, okay, it seems like both from the capitalist side, he created lots of jobs and he solved a big problem, he was also charitable, then I ask, what habits did he have that maybe are worth emulating? And if somebody else has a different opinion of him, that's fine, but then I can say, well, I like these habits, and I'll emulate them. Having a strong family, for instance, or having, you know, a strong ability to execute on ideas, which is something I didn't always have.

• 1:02:58Rich Roll?

  Right. I mean, you kind of break it down. You've got like obsession and, you know, overcoming resistance, persuasion, empathy, problem solving, and this idea of skill versus habit, which I thought was super interesting.

• 1:03:11Speaker 01

  Yeah, like, it's not, like, these people have, a lot of these people have real skills as opposed to just, oh, they're waking up at 6:00 a.m. every day, or they're, you know, going to the gym every day. These are all good habits and healthy habits to have, but how did Richard Branson persuade someone at Boeing to lend this 27-year-old nobody an entire plane, like a $150 million plane? I can't call up Boeing and just ask for a plane, like, they'll hang up on me.

• 1:03:38Rich Roll?

  What do you mean? You tried to buy Greenland, why not?

• 1:03:40Speaker 01

  Oh, yeah, it's true.

• 1:03:42Rich Roll?

  I mean, his ace in the hole was that there was an anti-competitive climate at the time.

• 1:03:46Speaker 01

  Well, was that his ace in the hole, or did he find that in the hole? Like, he was the one who brought that up to them. Like, he, they basically would said no, and he's like, well, listen, how else are you going to compete and get competitive pricing with British Airways? So he put this in their heads and convinced them. And so, it's interesting to see the little nuances of how these people achieve things because... It's, it is nuanced. Each, each skill they had, you know, their skills at persuasion or sales or execution or having creative ideas, or even the way they would do things. Like, so, you know, Damon John's an interesting example. He was, he was a waiter at Red Lobster,

• 1:04:29Speaker 01

  and on the weekends, he would sew these hats on his corner, and they had like hip hop logos on it. And then suddenly Macy's makes this hundred thousand dollar order. And he doesn't, he can't make a hundred thousand dollars worth of hats. He's worked, he works full-time as a waiter at Red Lobster. So what did he do? He said, of course, I will give you a hundred, give me a week, I'll get you a hundred thousand dollars worth of these hats. He had no reason to say yes. And, and then he goes to his mom, and he's like, Mom, I need to mortgage your house. And so he mortgages his mom's house, gets, you know, the money out, hires a bunch of seamstresses, and they work, you know, 24 hours a day in, in his

• 1:05:10Speaker 01

  mom's now mortgaged house. And then a few days later, he delivers the goods to Macy's, they give him the hundred thousand dollar check, he pays off the bank, gets the mortgage back, and now he has Booboo, which goes on for six billion dollars in sales. So what is the skill in that? That, that skill is what I call ready, fire, aim. So this kind of instinct to get all ready, like he knew he, he sold hats, a hundred thousand dollars worth of hats to Macy's, he hadn't yet aimed, he had no idea how he was gonna do it, but he fired. He said, yes, I'll do it. And, and that, this, why is that a skill? Because he knew there would be some way he can connect the dots. And he probably already had thought it out,

• 1:05:52Speaker 01

  but he knew no matter what, there would be some way he could connect the dots. And a lot of people would say, ah, I can't sell you a hundred thousand dollars worth of, maybe I could sell you a thousand dollars, we could do a test, or whatever. He, he just went right for it. And so Sarah Blakely, who, you know, she's the founder of Spanx, she had a similar thing. Jesse Yitzhak R. S. White. Jesse Yitzhak R. S. White. Jesse, I'm sure has been on, on this podcast, he's been on mine a bunch of times. And she was selling fax machines door to door. She had this idea for Spanx. She goes to sell them. She only has her one example, Spanx. The woman tried it on and said, "Yeah, I'll buy $300,000 worth of it." And Sarah Blakely's like, "Done. I'll get it to you."

• 1:06:34Rich Roll?

  Right.

• 1:06:35Speaker 01

  She had no manufacturer. She didn't know how to manufacture clothes at all. And it's not easy to convince some factory to manufacture all of these clothes for you. Are you gonna pay? Who are you? You're not a real company. And yet she found a manufacturer. She delivered the clothes and then Spanx was in business. So that was, again, this ready, fire, aim ability.

• 1:06:55Rich Roll?

  But ready, fire, aim has to be underpinned by a profound sense of belief in oneself, right?

• 1:07:02Speaker 01

  Believe in oneself.

• 1:07:02Rich Roll?

  You're not gonna move forward on ready, fire, aim unless you have some level of deep conviction about what you're doing.

• 1:07:09Speaker 01

  Yeah. And Sarah Blakely and Damon John, in this case, had had enough experience with, let's say, clothing and clothing design to roughly know how they were gonna connect the dots. Maybe they fully know, but more likely, they roughly knew how they could do this, how they could scale what they were already doing to something a hundred or a thousand times more. And so you needed this confidence, but you needed knowledge, too. So another example is Byron Allen. He recently, a few years ago, he bought the Weather Channel for $300 million. So he started out, he was a stand-up comedian, actually. He was the youngest guy ever on The Johnny Carson Show. And then he had all sorts of weird experiences in comedy. And he said, "You know what? I don't wanna be in front of the camera. I

• 1:07:52Speaker 01

  wanna be behind it. I wanna be the business guy. That's where the power seems to be." So he started pitching these shows, late-night shows, to television networks. And they're like, "Ah, no, this sounds kinda weak." And he said, "Don't worry about it. You don't have to buy the show. Let's just do a 50/50 split on the ads." And then he found the advertisers, and it cost- The the station's nothing. If he didn't come up with the money, they would never have aired his show. But he kept finding the advertisers. And it's like 25 years later, these shows are still running, and he's accumulated so much money from them that he's he bought the Weather Channel for 300 billion. He's bought other networks.

• 1:08:28Rich Roll?

  It's such a crazy story, because if you don't know that story, he's just the weird guy at 3am. You because that show is still on, I think. You turn it on like his interview show. And you're like, who that guy's still doing that? And it's kind of like.

• 1:08:42Speaker 01

  It's not really a quality show.

• 1:08:43Rich Roll?

  It's not a good show. And you're like, the show's been on for like 20 years. Like, how is this possible? Well, it's because he owns everything.

• 1:08:49Speaker 01

  Yeah, and he's he sold all the ads. And, you know, at that time, a lot of networks and still do they they just have infomercials for a half hour. So they basically say to him, if you we're we're running the infomercial unless you show up with like one penny more, we're running the infomercial. So he just went out there, got the advertisers and got syndicated all over the United States, created, you know, ES Networks, I think is the name of his company.

• 1:09:11Rich Roll?

  And yeah, he was like a fair to middling stand up comic, who was part of that whole like Comedy Store, you know, ecosystem. And I'm sure everybody told him he was insane for why, you know, why nobody would even think to do that.

• 1:09:26Speaker 01

  Yeah, and it's scary, too. In all these instances, there's a little bit of a fear factor like, oh, gosh, what if I don't raise the money? But he limits his risk. It's like, he doesn't have to put together the show either, really. First off, you see those shows, they're really cheaply done. It's just they're like a podcast on TV.

• 1:09:41Rich Roll?

  I know, I know.

• 1:09:42Speaker 01

  And and but he's he went out and sold the advertising. And again, that's ready, fire, aim. But there's also skills in sales, creativity, persuasion, and knowing what doors to knock on. And and if that didn't work, I'm sure he would have found some other thing. We think that's like their one idea. And if they didn't do that, they would have been a failure. No, my guess is all three of these people, Damon John, Sarah Blakely, Byron Allen, they probably would have succeeded at some other idea if that one hadn't worked.

• 1:10:08Rich Roll?

  Right. Well, on this theme of experimentation, you you decide to publish this book on Scribd.

• 1:10:16Speaker 01

  Yeah.

• 1:10:16Rich Roll?

  So that's so bizarre.

• 1:10:18Speaker 01

  Yeah, so.

• 1:10:18Rich Roll?

  Why would you do that?

• 1:10:19Speaker 01

  I've I've so I've published mainstream. Quite a bit. And then I've self-published quite a bit. So Choose Yourself was self-published and actually is my bestselling book.

• 1:10:29Rich Roll?

  That's the smartest thing you ever did.

• 1:10:31Speaker 01

  Yeah, that was, yeah, that was basically, I'm so glad I self-published that one. And I did what I called professionally self-published Choose Yourself. Like I hired a real cover designer, I hired real editors, I hired a real marketing company. And I really did it as if I was a publishing company, even even better than what I thought a publishing company would do. And it and it worked really well. But for this one, I felt like, ah, you know, I've already done one route, I've done another route. I want to experiment a little bit. And Scribd is like this Netflix for books. You sign up and whatever, there's million, yeah, you can read every book that's been published ever or close to it. And they just started doing, kind of like what Netflix did with shows, they started creating their own original books, Scribd originals.

• 1:11:12Speaker 01

  And so they approached me, I was, I was telling the CEO about this book. And he said, well, how about we publish it as a Scribd original? And I said, okay. And so it's an experiment and it's kind of six months exclusive there. And it's great. So I really enjoyed the experience. I've done, you know, part of the experiment was, what are the benefits? Well, they have a million plus subscribers that get their emails. Oh, so my name will be on an email to a million people. So just more, you know, this is not the last book I'm ever doing, or it's not the first book. But it's nice to have exposure to an additional million size audience. And to build a relationship with this Netflix of books, depending on, you know, they seem to be continue growing. And so, yeah, it's just another experiment.

• 1:11:57Rich Roll?

  And are you happy with how it's working out there? Like, is there a sense that this was the right move? Versus just putting it up on Amazon as a self-published work?

• 1:12:05Speaker 01

  Yeah, because on Amazon, again, I'm like every other book out there. And it's not like I'm against Amazon. I love publishing there and I love self-publishing there. But here's a case where I'm one of the only books in this category of Scribd originals in a website that, you know, maybe up to two million people go to all the time. So I figured, let's see if this is a real advantage. And you always want to go to the room least crowded. So when we were doing, when we started doing podcasts, and particularly when you started doing it. This was the room least crowded in media. Now it's very crowded, but like you said earlier, it's a good thing we got here when it wasn't crowded. So we could carve out our space. And here I'm on Scribd. That's in publishing.

• 1:12:47Speaker 01

  So I don't know, something like five million books a year are published now on Amazon. A lot of them self-published. Okay, here's a place where there's only four books published in this way.

• 1:12:56Rich Roll?

  Right.

• 1:12:56Speaker 01

  You know, they, they, all the mainstream published books are on Scribd.

• 1:12:59Rich Roll?

  The upside opportunity is much higher.

• 1:13:01Speaker 01

  Yeah.

• 1:13:01Rich Roll?

  For, for having something break out in a meaningful way.

• 1:13:04Speaker 01

  And if the book failed completely, okay, it'll be like 18 of my other 22 books that failed completely. So it's no big deal.

• 1:13:22Rich Roll?

  One of the things that I think we, we share in common is an aversion to setting long-term goals. Like, I don't know about you, but people ask me all the time, like, what's, what's your vision? Like, where do you see yourself in five years? Or, you know, what's, what's your life like in 10 years? And I honestly, like, I always feel guilty or perhaps even ashamed because I, I don't even think about that. Like, I can't, half the time I, I find myself like making something up to answer the question. And I've realized more recently, like, I'm just gonna be honest. Like, I don't, I have no idea. And I don't really expend mental energy in that way.

• 1:13:56Speaker 01

  That's funny, I didn't know that about you because I do think a lot of people talk in terms of, well, I want to be here in three years and then six years and then 10 years. And, and then, well, in order to be here in 10 years, I've got to do this today and like next month and whatever. And I think it makes no sense to have goals. It sort of implies that my knowledge now is so much greater than it might even be in 10 years from now. That my 10-year-from-now version of myself better listen to me now because I'm smarter now in terms of where I should be in 10 years. I don't know if this is all adding up, all the numbers, but. Basically, you're learning more every day. So tomorrow or next month, I might know something about myself and my interests and my passions

• 1:14:37Speaker 01

  or about the world that changes where I want to be in a month or two months or in a year. So you can't, I don't understand like how people could even figure out, how will they even know what they want to be in one year or five years?

• 1:14:49Rich Roll?

  Well, I think that goals have their place. Like if you say, you know, if you say like, this is something I want to manifest in the next year, then there are certain steps you're going to have to undertake to realize that. Like if I'm, if I want to do a crazy race, for example, or complete a book, like there you can set up benchmarks to lead you in that direction. And I think that's completely appropriate. But I think forecasting a vision for your life, I guess it works for some people. For me, it doesn't. Like everything that has been successful in my life has been, I wouldn't call it happenstance, but it didn't result from me, you know, putting it on a vision board.

• 1:15:26Speaker 01

  Yeah, like, like, you know, I think that's a good difference between goals and what was the word you just used?

• 1:15:35Rich Roll?

  Stepping stones?

• 1:15:36Speaker 01

  No.

• 1:15:36Rich Roll?

  Benchmarks?

• 1:15:38Speaker 01

  No, but, but, but like that.

• 1:15:39Rich Roll?

  Aspirations.

• 1:15:40Speaker 01

  You know, there's a difference between having something that you're moving towards today. So like, let's say you want to get a faster running time for a marathon. Okay, you could adjust things a little bit in how you're running. And today you're going to try this and see if your running is faster. But what if two months from now? And, and, and all of this could be because a year from now, you want to enter in this marathon and do it faster than a certain time. But what if two months from now, I don't know, Disney calls you up and says, Rich Roll, we want you to play Iron Man's father in the next Iron Man movie. And you're like, well, I was going to do this marathon and that's my goal. So like, call me back in a year. You wouldn't do that. You would just change. Now that's an extreme example, but yeah.

• 1:16:25Speaker 01

  So today you could say, well, I really want to benchmark myself against how I'm doing a race and I'm going to improve. Otherwise you would just, there's no reason to do anything. But things change and the things you love doing change. What if suddenly you decide, oh man, I really. Love writing cookbooks and decide two months into the year, I really just want to spend this year, all my creativity, writing cookbooks and that and your goals changed. So the year I started more passionately doing standup comedy, my goal, so to speak, for the year was I was gonna write a novel. That was where I was gonna put my creativity. But then I just started going up more than once a week on a stage and then I got heckled once and

• 1:17:07Speaker 01

  I'm like, you know what, I'm gonna just, next week, I'm gonna come back three times and I'm gonna figure out why I was heckled and I'm gonna talk to people and think about this. And it just never stopped. I never got back to writing that novel. Things change.

• 1:17:21Rich Roll?

  But ultimately, the fidelity is to your curiosity, right?

• 1:17:25Speaker 01

  Yes.

• 1:17:25Rich Roll?

  And I think when you, when you double down on your curiosity and you have the willingness and the tenacity to follow that, like to continue to pull on that thread, it creates a compounding interest that, that in a real world context, shows up in opportunities that you couldn't have predicted or imagined.

• 1:17:42Speaker 01

  Yeah, like, let's say, for instance, Greenland, suddenly.

• 1:17:47Rich Roll?

  James, we, now we're interested.

• 1:17:50Speaker 01

  Yes, suddenly, suddenly, or let's say, suddenly, somebody says, you know, this is a great idea. How about we write a movie about somebody who buys Greenland and what happens?

• 1:18:00Rich Roll?

  Right.

• 1:18:00Speaker 01

  And, okay.

• 1:18:01Rich Roll?

  Like, what if it actually worked?

• 1:18:02Speaker 01

  Yeah, like, well, I would say yes to any of the possibilities. Instead of going back to a standup stage, you know, it just, because you sort of fall in love with different things and you experiment enough with enough things that, you know, you figure out, oh, yeah, this is pulling me a little bit more, so I'm gonna double down on it. And then everyone say, well, what, wait a second, you were just doubling down on this other thing. No, no, no. Now, I really feel more passionate about this. So again, as long as you don't say, ah, no, I'm not gonna take care of my kids anymore, I'm gonna backpack around the world, there are certain responsibilities that you have to do. But, again, with, given, our creativity is very free. We could do, we could spend it, in most cases, how we want. And you should try lots of things and, and see where your, your, your heart is kind

• 1:18:47Speaker 01

  of compelling you to go further. Even whether you're failing or succeeding at that point doesn't matter. It's like where you, ah, I wanna get better at this. This is fun when I'm doing it and it's not fun when I'm doing other things.

• 1:18:59Rich Roll?

  Right. In thinking about this podcasting space, I think there's, how many podcasts are there now? Like,

• 1:19:06Speaker 01

  I think two million.

• 1:19:06Rich Roll?

  Two million.

• 1:19:07Speaker 01

  Yeah.

• 1:19:07Rich Roll?

  Two million podcasts, like, how many hours of people talking spontaneously about whatever's going on in their mind? And I thought the other day, I thought, what if podcasting existed in like 1780, you know, what if, what would podcasting look like in 18, like, if we could go back and just listen to people talking about the times in that time, what an incredible historical record that would be, that would shape and, and, and change how we think about history and how we consume history and how we synthesize world events. And now we're creating that now, like 100 years from now, this will all still be, you know, available to people to look back on and, and try to better understand, you know, this moment in time.

• 1:19:51Speaker 01

  Yeah, I mean, uh, you know, imagine back in the 1780s, like just Benjamin Franklin and John Adams would be having like,

• 1:19:58Rich Roll?

  Right. What if Marcus Aurelius, instead of like, you know, writing his meditations, was doing a podcast about it?

• 1:20:04Speaker 01

  Yeah, a podcast that was like, Seneca, can you please come on my podcast? I'll promote your notes of Seneca. We'll talk about it everywhere. And, uh, yeah. And, you know, I wonder about now with two million, how do you separate out the good from the bad? And I don't like to call any of them bad. Like everyone's trying, but I'm, again, it's like we were talking about earlier, I'm trying to just always understand formats and how much, you know, how can I change the format just slightly even from my usual one? And I, you've been doing a lot of great stuff with YouTube and videos, like you've been combining kind of your, your podcast voice with a kind of more conceptual video about what you're talking about.

• 1:20:47Rich Roll?

  Yeah, we just started doing that and I want to do more of that. But that's, that's an experiment.

• 1:20:52Speaker 01

  Yeah, it's totally an experiment. How long will you do it? Maybe you do 10 of them, five of them, 50 of them. And people will say, well, no, you've got to be consistent and focused. That could be true. Maybe you need to do 1,000 of them and then it just suddenly you have millions of views per video. But you might get tired of doing them after 20. And you say, no, let's focus on TikTok instead. So, or whatever you focus on next. And so, yeah, it's just a matter of, I'm always, it's interesting now too, because another thing that's happened in the media world that's changed, which is that I think followers don't matter anymore. So people have, you know, X number of Twitter followers, YouTube subscribers, Instagram followers, Facebook followers. I don't think that matters anymore because I think algorithms have basically ruled over followers.

• 1:21:37Speaker 01

  So, so the algorithm will decide where your, who sees your video or who sees your photo, not so much your followers. Because if you have, let's say you have 100,000 followers or even 10,000 followers. And let's say a lot of them have hundreds of followers and they're on Instagram for three minutes. The algorithm's got to pick which one of their followers are going to be rewarded with their eyesight. So I think it's very hard in today's world to come up with good, appealing content that rises to the top. It's, in a good way, it's much more equalitarian. Everyone's got an equal footing because followers don't matter as much. On the second hand, it's harder to curate, I think.

• 1:22:15Rich Roll?

  Well, it, it makes it rife for trying to manipulate. It becomes about manipulating the algorithm. I think that leads to substandard content in order to game the system. But I think it is true, like the follower count thing. I mean, there was a day, you know, in 2009, if somebody with a million followers like retweeted your tweet, you would, you would get, like in five minutes, you would get 30,000 new people following you. Like now, every once in a while, somebody of that stature will share something that I've done at zero impact on anything. You know, it's like that ship has sailed and I don't have a huge Facebook. Following, I think it's like 130,000 or something like that.

• 1:22:55Rich Roll?

  It's substantial, but I'll post the podcast on Facebook and it'll get like two shares.

• 1:23:01Speaker 01

  Yeah.

• 1:23:02Rich Roll?

  Like it'll, and it'll show you how many people it sees it and it'll be like 400 people. It's like unless you pay to boost this stuff or create ad campaigns around it, they just choke it.

• 1:23:11Speaker 01

  So I try, I try that too. I, I, I pay ad campaigns sometimes around the podcast. Does useless, doesn't work.

• 1:23:18Rich Roll?

  Like, so I'll have 50,000 people view it magically.

• 1:23:21Speaker 01

  I don't know who these 50,000 people are.

• 1:23:22Rich Roll?

  But it doesn't matter.

• 1:23:23Speaker 01

  Yeah, still five people clicked on it.

• 1:23:25Rich Roll?

  Right.

• 1:23:25Speaker 01

  So, so it's not even, has nothing to do with the content. I don't know what it has to do with. And, and I'm pretty sure I'm structuring these ads right, but I don't know all of that. It's always important to still have as high quality as possible, but other things are sort of rising to the top of importance. And it's, they're harder to, to figure out. And I don't like the idea, it's even hard to game the algorithm, but I don't even like thinking in that way somehow.

• 1:23:48Rich Roll?

  I never think about it.

• 1:23:49Speaker 01

  Yeah.

• 1:23:50Rich Roll?

  Ultimately, like, I think, you know, people will say, oh, you should do this and you should that. Here's the strategy and here's how you should lay out your Instagram. And I just can't, I can't wrap my head around any of that. And I just believe to this day, even if it's hard, that ultimately, you know, the highest quality content will rise to the surface and it will find its audience. And that means that you have to be in it for the long run and you have to be patient. And you can't be upset if it's not getting the, you know, the, the level of attention that somebody else who's, who's specifically crafted content to create some level of virality is going to get.

• 1:24:28Speaker 01

  Yeah. And so, so what's interesting there is you have a specific point of view also. So you're, you're not, you're not just hoping that the quality is, is going to get a lot of people. You have a point of view that people, if they, if they want your point of view, they have to listen to you. And so it could be you get. Let's say a hundred thousand super loyal people listening to your podcast. And you say to yourself, well, why does this other person have a million people? Well, they're just talking about, I don't know, the election every day. And then those people are going to disappear. They're not, they're not saying anything unique. It's just they're getting, giving the latest news or whatever. And, you know, so I think sometimes even measuring the number is the wrong metric, but we're used to it in this social media world. How many followers? How many subscribers? How many downloads?

• 1:25:13Speaker 01

  And you have to get back to like, well, if only a thousand people liked me, but they really love it. I mean,

• 1:25:19Rich Roll?

  I think that's more valuable.

• 1:25:20Speaker 01

  Yeah.

• 1:25:20Rich Roll?

  Like, I honestly, yeah, that my ego always wants something to be bigger and to be growing at a certain trajectory. But ultimately, what's meaningful about this work that, that you do and that I do is the capacity to impact people. And to the extent that you can improve the quality of the work to, to exacerbate that impact in a positive sense, so that they're left with something substantial that really can move the needle and how they're live their lives. That's, that's the opportunity there. And so I try my best to like, remain focused on that.

• 1:25:53Speaker 01

  Yeah. And, and, and so let me ask you this. Has anyone ever walked up to you and said, oh, my God, Rich Roll, your Instagram changed my life?

• 1:26:05Speaker 01

  Like, has anyone ever said that to you?

• 1:26:06Rich Roll?

  No.

• 1:26:07Speaker 01

  Right, but they'll come up to you. I bet you they have come up to you and said, oh, Rich Roll, your podcast changed my life.

• 1:26:12Rich Roll?

  Yeah, that happens a lot.

• 1:26:13Speaker 01

  Yeah.

• 1:26:14Rich Roll?

  And sure. It happens to you.

• 1:26:15Speaker 01

  Yeah. And, and again, no one's ever said to me, oh, man, your Instagram, I love it. I check it out every day. Like, no one said that. And I have just as much followers there maybe as anyplace else. And you start to realize, okay, well, why am I pursuing that? Is it just for the numbers? Or like, really, where, where, I know where people are being impacted because they tell me. And so why am I trying to get TikTok followers or whatever?

• 1:26:41Rich Roll?

  I know. You, you joined TikTok, right?

• 1:26:42Speaker 01

  Yeah, I joined TikTok. And by the way, that's a very creative medium. I'm not knocking TikTok.

• 1:26:47Rich Roll?

  My daughters, they, they specifically prohibited me from joining TikTok.

• 1:26:51Speaker 01

  Now, do they use it and they don't want you on it?

• 1:26:52Rich Roll?

  Yeah, they use it. They use it. My younger one more than my older one. But she was just more, I, because I was joking with her the other day. I was, I'm going to join TikTok. I gotta check this out. You know, half joking, like, that's kind of where I draw the generational line. You know, it's like,

• 1:27:06Speaker 01

  But TikTok's really creative, actually. I love the scrolls and the videos.

• 1:27:09Rich Roll?

  So I was like, I was kind of playing around with it. And, and, and, and my youngest daughter was just appalled. She's like, please don't, please don't.

• 1:27:16Speaker 01

  Yeah, I mean, I was playing around with it. And then I put, I didn't have any followers and I put up one video. I put up a couple of videos and one video got something like 200,000 views. And so I thought that was interesting that, okay, they're, they're treating the algorithm differently than other places.

• 1:27:32Rich Roll?

  Well, it's, it's Twitter in 2007. Like, the opportunity to grow rapidly is available on that platform because it's a new platform.

• 1:27:39Speaker 01

  Right, but then I looked at the video that did get me the 200,000 views and I thought, man, that is the stupidest video I've ever done. And so it's just meaningless.

• 1:27:47Rich Roll?

  Right, right.

• 1:27:48Speaker 01

  So I'd rather just do the podcast and not get.

• 1:27:51Rich Roll?

  Were you like dancing or something? What were you doing?

• 1:27:53Speaker 01

  Well, that one, people begged me to take down and I did. Like that, I decided, okay, this is beyond being afraid of what people will think of me. I'm making a fool of myself. So, so I took that one down.

• 1:28:04Rich Roll?

  Were you telling, you could tell, you could test out your material, though.

• 1:28:07Speaker 01

  I, I could, and I've seen people do that and kind of comedians. It's interesting because I saw kind of what I would say were regular club comedians in New York City, go on TikTok and suddenly get millions of views and 250,000 followers. And that actually was an indicator to me that this person was funny and appealing to a certain audience. And that, that was a data point for me when sort of seeing, because I own a comedy club too. So that was a data point for me in seeing, oh, should this person perform more here or not or whatever? But for me, I just put up some articles that, like, an article I wrote in 2011. I took it and just basically said it in a TikTok kind of fashion and it got 200,000 views.

• 1:28:49Speaker 01

  And another one that was against college got like 100,000 views or 80,000 views. So I thought, okay, it's interesting a little bit, but not enough. But it would took a lot of time, even doing a 15 second video. So I figured, okay, it's not, this is not worth really doubling down on. It's an experiment and it wasn't worth doubling down.

• 1:29:06Rich Roll?

  I appreciate the experimentation. And I also think it speaks to something that like Gary Vee talks about all the time, which is not being romantic about the platforms. Like, whatever's working, move in that direction. Like, you, you do lots of things, but fundamentally, I think of you as a writer, right? And this is, you know, you really developed your audience through your blogging on your website. But then kind of blogging, you know, really it's not like a thing anymore, right?

• 1:29:31Speaker 01

  No.

• 1:29:31Rich Roll?

  You pivoted to podcasting.

• 1:29:33Speaker 01

  And that's the problem with writing is that.

• 1:29:35Rich Roll?

  But like, writing should never go out of style. And yet, nobody is a blogger anymore.

• 1:29:39Speaker 01

  Yeah, no, there's no destination blogs. Like, it used to be the case, there's no destination websites.

• 1:29:44Rich Roll?

  Trying to get people to go to your website is futile. You have to go where everyone already is.

• 1:29:48Speaker 01

  Yeah, and so I think, I mean, then for a while, like, places like LinkedIn and Medium worked, but I don't really see that as much now. So I don't know, again, it's like, when people come up to me and say, "Oh, I love X", it's usually the podcast, and then one out of 10 will be writing, and it's never anything else.

• 1:30:06Rich Roll?

  And what do you think, how do you think about iterating on that going forward? Like, forecasting where podcasting is going? And perhaps, you know, being an early adopter of whatever the evolution of that is?

• 1:30:19Speaker 01

  I think it's, well, it's always hard to predict. Like, if you look at what's happening now, I mean, so we were doing the interview format, and a lot of people do that, and, look, the best, the most popular podcast in the world, The Joe Rogan Show, is the interview format. So that's kind of staying, but.

• 1:30:37Rich Roll?

  Two people talking, I would, I can't imagine is ever gonna go out of style if it's a substantive, interesting, entertaining conversation.

• 1:30:44Speaker 01

  Yeah, and then, and then what's, what's interesting is that storytelling is hitting the top 10, or the top 50, or the top 100, so like, true crime stories. So it's like back to 1920s dime novels about crime. That's what's shooting up the fastest right now in podcasting. And then I would say also, podcasts, and I look at Joe Rogan as an example, podcasts with a bunch of comedians talking is interesting. And again, Joe Rogan's got the most popular podcast in the world, and he's, he is a stand-up comedian. Often, he has his comedian friends on, that's who he's interviewing. And so I wonder if that's because it's a safe place to, to have extreme opinions, but not be accused of being polarized in one way or the other? So like.

• 1:31:29Speaker 01

  Joe and other people like that will say whatever they want. Like, it's just insane what they'll say. And if they were like a big, you know, intellectual or whatever, people say, you can't say that. It's this. You can't say that about climate change. It's this about climate change. You can't say this about the Republicans or the Democrats. It's the other way. But Joe, you can't ever figure out what he's talking about.

• 1:31:51Rich Roll?

  Well, because he, his genius is that, you know, he's the first, he'll just say like, well, I'm a dummy comedian. Like, you're, you're, you're, why are you believing anything I have to say? Like, that's always his refrain.

• 1:32:01Speaker 01

  Jon Stewart said the same thing throughout the entire, even though everybody admitted they got all of their news from The Daily Show. Jon Stewart would always say, oh, I'm not a news guy. I'm just a comedian. But he, we, he knew we all got our news from The Daily Show.

• 1:32:12Rich Roll?

  Right. Well, in the way that, that, that the porn industry drove technological innovation on the internet, comedians really are responsible for the birth of podcasting. Like, they were the, they were the early adopters. They were the

• 1:32:27Speaker 01

  Oh, yeah. Marc Maron, Adam Carolla.

• 1:32:29Rich Roll?

  Those are the guy, yeah. And like, the early days of podcasting, it was almost entirely comedians. And you're correct in that now, what's capturing people's attention, beginning with serial, are these longer, highly-produced stories. You know, our friend Neil Strauss did To Live and Die in L.A. did tremendously well. And those are the ones that are kind of rising to the top. So, does that leave you thinking, like, maybe I'll do something in that space? Like, the amount of work that goes into crafting that. Like, even if you took one interview and you, like, chopped it up and then you put voiceover review, contextualizing it, kind of like some of how the Gimlet shows do it. Like, I thought about that and I thought, that's just gonna take up too much time. Like, this is already taking up too much of my time?

• 1:33:09Speaker 01

  Oh, I'm sorry about that, Rich.

• 1:33:11Rich Roll?

  Well, yeah. And you've gone to, you're going to four times a week with your show now.

• 1:33:15Speaker 01

  But, but because two of those episodes, and maybe even three, is just going to be me bothered by something and talking about it, perhaps with a foil, perhaps someone's in there to tell me I'm wrong. But it's not going to be the standard, okay, gosh, I've got to read 12 books, you know, this week to prepare for my interview subjects and

• 1:33:36Rich Roll?

  It's exhausting.

• 1:33:37Speaker 01

  Yeah, it's exhausting. So, I kind of wanted to say, it's like what you were saying about, somebody said, you know, why were people listening to you? They weren't listening to see what you were asking the other person. They really wanted to hear you. And so, I figured, okay, let me just try this. I'm gonna say what I think is important to me this week and why, and how I'm being impacted and Kind of storytelling about me a little bit, or a big need people have is like, say, say when Iran happened. So January 3rd, you know, we attacked this guy, we killed this guy. And, and my kids were saying to me, is, are we getting drafted? Is there, is World War III about to happen? So there was this real fear among everybody. And I see it even

• 1:34:19Speaker 01

  my kids. And so I called up a big military expert. And I said, just, I don't know anything. And there's just a bunch of what I call spectators out there arguing all day long on Twitter and Facebook like they know something. Just let me ask you a bunch of questions, answer them. And now I'll know some more. And so that's what I did. And I think calming people down is a good role for podcasters with an audience. If you can get those guests and not have a traditional guest, but like, this is really scaring me right now. Let's break down what's happening. I think that's an easier format to prepare for because I know what I'm scared of. And I'm going to try doing that a little bit more as well.

• 1:34:56Rich Roll?

  Yeah, I think that with that, then you have to embrace the idea of doing this contemporaneous with current events. Like, I'm trying to do interviews that withstand the test of time and have an evergreen nature to them. And, you know, I've banked a bunch of interviews. And sometimes there's a long waiting period between they go. And I, and then I feel bad about it because

• 1:35:18Speaker 01

  Yeah, no, I know.

• 1:35:19Rich Roll?

  Wait, are you ever going to put that thing up that we did? And trying to find a way to be more facile with it. So from time to time, like, I can make, I, you know, I can do a more current event oriented kind of show.

• 1:35:31Speaker 01

  I've always, so I've done, I think I'm at 543 right now. It's all been evergreen. But I'm trying every now and then to, to be a little current event, just because sometimes people are scared. And there's no one, the media isn't properly addressing their fears because everybody's one side or the other side. And they're not just looking at facts. And also, the, the media has incentive to kind of exaggerate certain facts, or change certain facts. And I'm not blaming the medium, it's everybody. And so sometimes I just want to know, should I be afraid, or not afraid? So for instance, you know, there's a lot of discussion lately about, well, is AI and technology going to wipe out 30 million jobs in the US? Like, like all these people are saying. And so I've

• 1:36:16Speaker 01

  Been in the computer science industry a long time ago, but I called up current experts in AI and automation just to see where things were at. And I found out and got less afraid and was able to communicate that. So that's not going to be evergreen, but it's good to answer this question for the next six months or year that people have it.

• 1:36:35Rich Roll?

  Right.

• 1:36:35Speaker 01

  And so sometimes now I'm just, again, playing to see, maybe I need to be a little bit more current just to calm people down on really super important issues.

• 1:36:43Rich Roll?

  Of all these ideas that you've put out in the world, what idea stands out as the one that people went the most crazy about? Is it like you shouldn't go to college?

• 1:36:54Speaker 01

  Okay, no, the most controversial, well, the college one has gotten me death threats.

• 1:37:01Rich Roll?

  Really? Death threats?

• 1:37:03Speaker 01

  Death threats. So this is crazy. This guy wrote me, like, you know, he said all these things, I'm gonna, I'm gonna kill you. And his IP address or whatever was on the email. Somehow I was able to figure out his IP address. Turned out to be Brown University. So he was writing from Brown University and he put his name. So I called up, so my whole thing was is that I don't think kids in today's day and age, not necessarily 30 years ago or 40 years ago, but in today's day and age, kids shouldn't go to college because it's reinforcing the system of higher and higher tuitions. An entire generation of 30 million kids are going more and more in debt, which is going to increase income inequality and more and more bad things will happen. And you could learn these skills now from all these online sites and, but there's a societal pressure.

• 1:37:48Speaker 01

  Anyway, that's my whole thing on college. And this guy wrote me a death threat. And so I called Brown University Police. They put me in charge of the, the chief of police. And I should say allegedly Brown. I don't know if Brown will get upset at me. So, and, and, and I read the email and I said the name of the guy and the chief of police says, yeah, that's pretty bad. And, oh, by the way, yeah, we, we know that guy. He did a similar thing with the school librarian. And I'm like, well, shouldn't you do something about this? And he's like, come on, it's, it's March. Do you really want, he's in his senior year, just let him graduate. And I'm like, well, he's gonna graduate, maybe.

• 1:38:30Rich Roll?

  Yeah, that's the situation where, you know, two years from now, he does something really bad and nobody did anything.

• 1:38:35Speaker 01

  Right. And but there was nothing I can do, really, like, uh, but the the thing that's gotten people the most antagonistic of all was homeownership. So I would write, there's a lot of financial reasons why you shouldn't own a home. There's a lot of reasons why it's a really bad idea. And and people got really upset about that. I did it on Yahoo Finance. It got over 10,000 comments. I got, you know, millions of views and shares. And and I've written it as an article. I've done it as a podcast. Because that's the biggest financial decision you make in your life, there's all this.

• 1:39:10Rich Roll?

  It's also a source of tremendous pride for a lot of people. So you're you're basically challenging people's sense of themselves.

• 1:39:16Speaker 01

  Yeah. And and if you also spend that kind of money, your brain's not gonna let you think the day afterwards.

• 1:39:22Rich Roll?

  You're too invested.

• 1:39:22Speaker 01

  Yeah, yeah, you have investment bias. It's a mental model. And, uh, uh, so your brain's not gonna let you think you made a stupid decision. So people will fight that to the bone. Like, I've lost friends over that. I've lost friends over the college thing. I lost the most friends over, though, an article I wrote on, um, there should, you should, no war is ever really justified. And and I said, I don't know anything, I'm not a historian, but clearly, like, you go back to the past four or five wars, they're ridiculous. And I'll even go as far as to say, why did we do the Revolutionary War? Like, clearly, Canada didn't suffer because they didn't have a revolutionary war. And somebody would start writing me, well, what about the Peloponnesian War?

• 1:40:05Speaker 01

  I'm like, I don't even know what that is. So clearly, it doesn't matter to me. And but then I did lose friends. Like, somebody called me up a month. I realized I hadn't heard from a friend in a while. And I called him, like, what's, what's, what's wrong? And he's like, you're for, you're obviously pro-slavery. And I'm like, what are you, how, what are you talking about? How can I be pro-slavery? And he said, you, you said no war can be justified. So that means the Civil War can't be justified. Well, slavery justifies it. And I said, You could have just called me and asked me if I think minorities should be slaves. Like, clearly I don't. And I said, well, look at the, you know, England got rid of slavery in 1831. Maybe if we hadn't done the Revolutionary War, there wouldn't be slavery because we would have been part of England. And I said, I don't know history.

• 1:40:50Speaker 01

  I just feel like when 20% of the country has died shooting each other and it's all 17-year-old kids, it's probably not the best idea. There maybe would have been another way to do it. But I said, I don't know. I just think kids shooting kids is a bad idea.

• 1:41:03Rich Roll?

  Well, two things. I mean, first of all, they, these friends that you've lost couldn't have been, you know, great friends.

• 1:41:09Speaker 01

  That one was like a 20-year friendship. I was really surprised. But he, but he was of Indian descent and, you know, took kind of personal.

• 1:41:19Rich Roll?

  I understand.

• 1:41:20Speaker 01

  And, and I'm Jewish. I said, look, I don't think World War II should have happened.

• 1:41:24Rich Roll?

  Right. But this is, like, to know you is to know that, that you're very much a provocateur in the sense, like, when I see, oh, like, here's another crazy idea that James has been thinking about, you know, it's like, you put it out there and I think there's a, you know, a perhaps slightly unconscious, like, glee that you get from, like, let's see what happens with this.

• 1:41:45Speaker 01

  Yeah, a little bit, but I don't try, I don't say things, for instance, I don't, you know, I don't blindly disbelieve, like, you know, you take, you, there's enough research to basically connect the dots. Like, the theory is, first, it's probably not a good idea to send 18-year-olds to kill other 18-year-olds because bad things will happen. And then you have to look at, there's all sorts of ways to, to look at every war, but I also know history's written by not just the winners, but a very tiny percentage of the winners write history and they kind of make the facts fit what happened. Now, all of these situations, obviously, everything was horrible. Who knows what the right solution was?

• 1:42:27Speaker 01

  War turned out to be the solution to some big catastrophic problems. It's just a thought experiment. What, if there was never a war, what would, what would it be like? Less people would die, so.

• 1:42:37Rich Roll?

  It's, it's, it's leveraging a couple of the mental models that, that Shane Parrish talks about. It's thought experiment, but it's also first-order thinking. Like, you're, here's something we accept that's just kind of locked in our awareness as being true or just the way it should have been, or, you know, should be or, or is, right? And you're saying, well, let's forget about that and look at it completely differently. And then taking kind of a counterintuitive position on it.

• 1:43:03Speaker 01

  Yeah, just a slight thing, you know, we dropped the atomic bomb twice because the theory was that, oh, and this is how history's been written, a million American lives would have been lost if we did a full-scale land invasion of Japan. I don't know if that's true. No one's ever told me how, where, how those numbers add up to a million. And also, there was a lot of people arguing back then that maybe we should just contain Japan until they give up. They're already kind of almost giving up. And so it's very unclear what would happen.

• 1:43:35Rich Roll?

  Or why drop two bombs?

• 1:43:36Speaker 01

  Yeah, why drop two bombs? They were literally about to capitulate. You can argue, nah, they're gonna hold out, but we didn't need to invade them at that point. A million lives wouldn't have been lost. So who knows? You always have to question, you know, why are people doing things in a certain way? What's the, there's gotta be a backstory and a backstory to that and a flip story and all this stuff we have no clue about.

• 1:43:57Rich Roll?

  Right. All right. Well, we gotta round this down, but let's talk a little bit before we end about your perspective on the biggest ways in which people get in their own way.

• 1:44:09Speaker 01

  Yeah, that's a good question. Let me ask you, like, what do you, you know, what do you think is the biggest way you get in your own way? You've mentioned a couple. You feel imposter syndrome?

• 1:44:18Rich Roll?

  Yeah, imposter syndrome. I'm insecure. I'm, you know, sitting here looking at you, but I'm thinking like, do I sound like a dummy? You know, like, what's the next question? Can I keep the momentum of this? You know, like, I get up in my own head and I'm my own worst enemy.

• 1:44:34Speaker 01

  By the way, it's really hard being a podcaster, right? You have to kind of always think of questions ahead.

• 1:44:39Rich Roll?

  That's when I said, wow, you're doing four of these a week. Like, I've done Saturday, Tuesday, Wednesday. This is the fourth one that I've done in five or six days.

• 1:44:49Speaker 01

  It's hard.

• 1:44:49Rich Roll?

  And I'm like, tired. You know, and I'm like, okay, but James is coming. Gotta be on my game. So I can't imagine doing four every week. So that's a stamina, stamina, endurance contest in its own right. But in terms of how I get in my own way, like, I think.

• 1:45:06Rich Roll?

  Yeah, I'm profoundly insecure. You know, like, I have tools to keep those things at bay, and I'm very self-aware of a lot of these limitations. But they still infect my ability to, you know, kind of optimize my, what I'm trying to accomplish.

• 1:45:22Speaker 01

  I think, I think, but I think you nailed it, though, with being self-aware. And not necessarily, you know, it's, everybody could say, "Oh, you need to be more self-aware, self-aware, self-aware." And it's hard to do. You have to really be honest with, what are my weaknesses? What are my strengths? So I know, I have like huge weaknesses and psychological issues around, let's say, money. I've gone broke so many times, I'm like literally afraid to look at my bank account.

• 1:45:52Rich Roll?

  But you have this ability to, to create money as well.

• 1:45:55Speaker 01

  Yeah.

• 1:45:55Rich Roll?

  You've done it many times. There must be conflict.

• 1:45:57Speaker 01

  Because I lose it, too.

• 1:45:58Rich Roll?

  If you lose it all, like, you're like, "Yeah, but I figured this out so many times."

• 1:46:01Speaker 01

  It's always a disaster every time, though. So I'm knocking a lot on wood right now. But also, I think, knowing, being aware of what you're interested in doing. So at one point, this is about a year ago, I was pitching a TV show, and, and a network picked it up. And I thought to myself, huh, this TV show idea is good, but do I really want to do it? This is going to take thousands of hours of time. I don't think I want to do it. And so knowing, knowing when your heart wants to do something, when your heart doesn't want to do something, I think is really important part of that self-awareness.

• 1:46:36Rich Roll?

  Was that like a narrative show, or a...

• 1:46:38Speaker 01

  No, it was like a kind of social experiment reality show. I'll tell you the idea, since I'm not, totally not doing it. But I was going to take six random people off the street, and the premise of the show was, if they followed my advice exactly, I would make them a millionaire within six months. So... But you know, some would bail, some would succeed, someone would like beat me up or whatever, like you know, typical reality show stuff. And but I thought to myself, they won't, network's not really gonna know if this is good until it's over, until I've done it. And what if it doesn't work? Or it's just gonna take a huge amount of time flying all around the country. They wanted people in every city and and they wanted more than six, it's just they picked the best six.

• 1:47:20Speaker 01

  So it'd be so much work and I felt myself like afraid of doing that much work. So ultimately, it didn't happen. But I think also being aware of like what you're willing to do, what you're not willing to do.

• 1:47:32Rich Roll?

  So the self-awareness piece in that is is the understanding like this isn't really what I want to do and then following that up with pulling the plug on it, even though it could be this huge amazing opportunity.

• 1:47:43Speaker 01

  Yeah, yeah, because, look, if if there's a lot of ways to go for making money, making a TV show or doing a podcast or going into stand-up comedy or not, or even being a writer, those are not ways to make a lot of money. You don't go into those thinking, man, I'm gonna make billions now. Forget being a plumber, now I'm gonna be a podcaster. It's just gonna start rolling in. That just doesn't happen. So so I think a lot of it is about just being aware of what your capabilities are, what you really want to do versus what you're what you don't want to do, understanding what skills you don't know. So somebody could say, I want to be an entrepreneur. Well, what's what's entrepreneurship? There's no skill called entrepreneurship.

• 1:48:25Speaker 01

  Entrepreneurship is this bag of other skills like sales, ideas, execution, marketing, motivation, leadership, there's all these other skills and added together, it equals this, you could call it this one meta-skill entrepreneurship, but that's not really a skill. So understanding what, if you want to do something, what micro skills you need to learn, you have to avoid, you know, in whatever you're doing, you have to avoid smoking your own crack. Like you could think, well, I'm doing this, so it must be great. And I see that all the time among entrepreneurs or even podcasters. I'm doing this idea, it must be the best idea in the world. Why aren't people coming to it? I'm gonna have to advertise now. You should try to always ask if if you're smoking crack on your ideas, because I think

• 1:49:09Speaker 01

  that's a real easy bias also. That's a mental model as well.

• 1:49:12Rich Roll?

  Right, right, right. What do you think is your your greatest strength? Like, what is the secret James Altucher sauce that that has propelled you to this place?

• 1:49:22Speaker 01

  I'm not, I'm not sure because I'm not so sure I've done, I'm not sure so sure I've been propelled anywhere. But I think I'm, I think I have a lot of fun coming up with ideas.

• 1:49:34Rich Roll?

  Yeah.

• 1:49:34Speaker 01

  So that's the thing I've written about the most is like, I write down 10 ideas a day. And it just, I realized kind of shortly after I started doing this, that, that just writing 10 ideas a day, and it could be about anything. It could be about just, oh, 10 ideas for Valentine's Day gifts tomorrow, or 10 ideas that Google could do to be better. And they could all be bad ideas, but if you just kind of exercise this idea muscle, it really will get better. And if you don't exercise the idea muscle, it will atrophy. So the times when I was like, losing all my money, I was letting my idea muscle atrophy. Instead of no matter what, no matter how bad things seemed, I started always exercising this idea muscle,

• 1:50:15Speaker 01

  writing 10 ideas a day down. Like I wrote ideas the other day for, I wanted to make this card game. Again, it's an experiment, and I just wrote the rules. And that was my 10 ideas of the day. And, and so-

• 1:50:28Rich Roll?

  And of how, of those ideas, how many of them do you take action on?

• 1:50:33Speaker 01

  One out of a thousand. So people say like, how do you keep track of the ideas? And how do you know which ones are going to be good? You never take action on them because it's really just like, if you exercise by lifting weights, it's not like you think the next day, well, I don't have to lift today because I lifted really good weights yesterday.

• 1:50:49Rich Roll?

  Yeah.

• 1:50:49Speaker 01

  Yeah, it's just practice. And, and you'll know the good ones because the next day, you'll figure out 10 more ideas that are about that. It might be 10 execution ideas about one of the ideas from the day before, or a week before, or a month before.

• 1:51:01Rich Roll?

  One of the ones I heard you talking about recently was trying to pay for stuff with North Korean currency.

• 1:51:07Speaker 01

  Oh, yeah, yeah.

• 1:51:09Rich Roll?

  And Iranian currency?

• 1:51:10Speaker 01

  Yeah, so I, on a, on a fluke, I wandered into this random auction house that had currency. And I just, this guy had like this bag of money, like just in the, it was like this old dusty store. You could picture it with all, all these garbage bags, all this stuff. And I started finding like North Korean currency, Saddam Hussein currency, Idi Amin currency. So there was all this like weird dictator money. And so I would, I bought a bunch of it and I started, um, I figured it'd be fun idea to video to me trying to pay for things like, hey, I'm, I'm at, I'll go buy a cup of coffee. Hey, I'm out of money, but I have this, you know, Kim Jong Il currency. It's valid in North

• 1:51:53Speaker 01

  Korea and nobody ever has taken the money. So

• 1:51:58Rich Roll?

  They won't even touch it, right?

• 1:51:59Speaker 01

  Yeah. Some people, some people, it's weird. Some just, uh, I think maybe they're afraid it's infected with something or there's some poison. I have no idea.

• 1:52:07Rich Roll?

  I think, I think, well, if it's a gnarly dictator money, it, it, if it almost feels like you're complicit in that regime, if you touch it.

• 1:52:16Speaker 01

  Yeah.

• 1:52:16Rich Roll?

  And I think with a vendor, they think if they touch it, then that constitutes an agreement.

• 1:52:21Speaker 01

  Or maybe also because there's like sanctions, like we have sanctions against North Korea. Maybe if you're holding on to a bill from North Korea that's against the law.

• 1:52:29Rich Roll?

  Yeah, but I don't think anyone thinks about that. It is weird. It is an interesting thing though.

• 1:52:33Speaker 01

  Yeah. Cause I always ask people, why did you not, here, touch it? And they're like, no, I, they specifically don't want to touch the money.

• 1:52:40Rich Roll?

  They don't have a, a good answer for why.

• 1:52:43Speaker 01

  Yeah. They don't, nobody has given me an answer.

• 1:52:44Rich Roll?

  Yeah.

• 1:52:45Speaker 01

  They just don't want to. It like creeps them out.

• 1:52:47Rich Roll?

  What's the next crazy experiment? And then we'll finish this thing.

• 1:52:50Speaker 01

  Well, uh, uh, there's a lot really. Um, there's this skip the line book that's coming up. Uh, and

• 1:52:59Rich Roll?

  You're doing that with a traditional publisher.

• 1:53:00Speaker 01

  Yeah. So almost an experiment to do, go mainstream.

• 1:53:03Rich Roll?

  What a crazy experiment. James is actually going to go the traditional route.

• 1:53:07Speaker 01

  Well, I really wanted to see how things have changed in that world. And I think they have a little bit, but they, and everything I thought initially was that they rely on your marketing ability as well is true. So, but now they just, everybody sort of knows the story. Like that's the, they know you have to do that and you know, you have to do it. And, and yeah, a lot of things I'm experimenting with, like I've been playing around with doing this card game. And now I know how to do a Kickstarter because of Greenland. So I'm going to Do a Kickstarter for this card game once I print up the first version of it. And that's just a fun thing. The key with an experiment is it shouldn't take up too much time or money. Another thing I've been doing is I've been putting what I call anti ads on the backs of cabs in New York City. You ever go to New York City and you see on

• 1:53:52Speaker 01

  the back, there's a little TV show and there's ads. And the ads will be for real products. So I've been creating these ads that don't advertise anything. So there's just like, it's just like a picture of me saying hi. And they called me up, they called me up and they said, you have to put a URL, or don't you want to put a URL or a Twitter handle or something? And like, no, that's the whole point. No URL, no Twitter handle.

• 1:54:16Rich Roll?

  But that's like, that's like performance art.

• 1:54:18Speaker 01

  Yeah, it's a little like that. And I kind of want to see what happens, though. Like, does it? And I've had at least one instance, because I did this for a couple of months, I'm doing this for a couple of months. And one guy now did come up to me last week, and he's like, you're that, you're that Taxi TV guy. My nine-year-old loves you. And he took a selfie with me. He didn't know my name.

• 1:54:37Rich Roll?

  He didn't know anything, other than you said hi and a little sticker.

• 1:54:41Speaker 01

  Yeah. And the Taxi TV people said, we can't run this, because originally it didn't even have hi on it. And they said, we can't run this.

• 1:54:48Rich Roll?

  Just a picture of your face?

• 1:54:50Speaker 01

  Yeah, it was just a picture of my name. And by the way, it was really like, I was wearing a white t-shirt, and I was standing next to a white background. So it was the worst possible way to structure a photo. And the Taxi TV people said, we have to have a certain bar. We have, you know, professional advertisers advertising on this. We can't run this. So they made me, and they had a good idea. So I can't say they made me. But they said, make it a little bit of a story. So I put hi on the first one, and like, hi again on the second one. And I forget what we put on the third one, like a math puzzle or something. But, so that's an experiment. And I have like

• 1:55:24Rich Roll?

  So those are up in New York right now, cruising around?

• 1:55:27Speaker 01

  Yeah.

• 1:55:27Rich Roll?

  Oh, my God.

• 1:55:28Speaker 01

  And I have like 20 of these experiments going on, these different types of things like this. That all seem small. And, you know, also working on another TV show, which would be much less work, and experimenting with the format of the podcast. And it's just things I do all the time to figure out, okay, if it doesn't take time or that much money, I can do it. And so I do it.

• 1:55:48Rich Roll?

  I love it. And I love you. You're fantastic. I love the work that you do. And you know what? Let me just say this. You look great and you seem really happy.

• 1:55:56Speaker 01

  I am.

• 1:55:57Rich Roll?

  It makes me happy to see.

• 1:55:58Speaker 01

  Thank you, Rich. I've been, um, uh, I wish I could say how I've been living your healthy lifestyle, but you're always there.

• 1:56:05Rich Roll?

  I know you've taken stabs at it.

• 1:56:07Speaker 01

  Yeah, I've taken stabs. I remember one time you visited me and you were talking and my, my daughter, my red haired daughter was about to turn full vegan. And I think you actually, listening to you actually put her over the edge. Like she was just like, listen, sitting there like rapt while you were talking. And now she's been like literally a vegan ever since. It's almost four years later.

• 1:56:26Rich Roll?

  I love it.

• 1:56:27Speaker 01

  So, so at least she's living that lifestyle, but I try to be healthy.

• 1:56:31Rich Roll?

  Well, we're working on, this is, this is, this is perhaps a new experiment for you.

• 1:56:34Speaker 01

  Yeah, it could be. Could be.

• 1:56:35Rich Roll?

  All right, man. Well, to be continued.

• 1:56:37Speaker 01

  Yeah, definitely. Thank you, Rich, as always. And I look forward to our, our next get together on, on the air.

• 1:56:42Rich Roll?

  Sooner rather than later, I hope.

• 1:56:44Speaker 01

  Yeah.

• 1:56:44Rich Roll?

  Cool. Peace.

• 1:56:49Rich Roll?

  Always, always a super good time with James. Hope you guys enjoyed that. Some good gems in there for sure. And I hope you find it useful as well as entertaining. Do me a favor. Let James know what you thought of today's conversation. For more on him, check the show notes on the episode page on my website. You can go to his website, jamesaltucher.com, and you can follow him @altucher on Instagram and @jaltucher on Twitter. If you'd like to support the work we do here on the show, subscribe, rate and comment on it on Apple Podcasts, on Spotify and on YouTube. Share the show or your favorite episodes with friends or on social media. And you could support us on Patreon at ritual.com/donate. Thanks

• 1:57:31Rich Roll?

  to everybody who helped put on today's show. Jason Camiolo for audio engineering, production, show notes and interstitial music. Blake Curtis and Margot Lubin for videoing the podcast. Jessica Miranda for graphics. Ally Rogers for portraits. Georgia Whaley for copywriting and DK for advertiser relationships. As always, the theme music is by my boys Tyler Piot, Trapper Piot and Hari Mathis. Side note, I've got Tyler working on some new music for the pod, so stay tuned for that. And with that all being said, thank you for the love, you guys. I will see you back here in a couple of days with who knows what, when, where and why. Like I said, I've gone through my stash of episodes recorded prior to the pandemic,

• 1:58:13Rich Roll?

  so I gotta figure out what's next. But I can promise you this, it's gonna be good. So until then, peace.

• 1:58:21Speaker 01

  Almost a reinvention.

• 1:58:52Speaker 01

  Yeah.