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James Altucher - Choose Yourself: How To Turn Your Vulnerability Into Freedom

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The James Altucher Show

James Altucher is an American hedge fund manager, venture capitalist, entrepreneur, author, and podcaster. He has founded or co-founded more than 20 companies and written over 20 books.

Master of The Side Hustle

For this episode I flew to New York City to speak with James Altucher.

The best-selling author, chess master, comedian, cryptocurrency expert, entrepreneur and broadcaster, James Altucher is a truly fascinating guy. He’s always up to something new and today’s episode is proof as I got to sit down with James in his new comedy club.

This is what James is like. He just went ahead and bought a comedy club and now he actually practices as a stand-up comedian!

James Altucher’s podcast

James also where he interviews influential figures such as Sir Richard Branson and Mark Cuban. His show has been downloaded over 40 million times and James has written thousands of articles for the Wall Street Journal, TechCrunch & The Financial Times.

Along with his articles, James’ book “Choose Yourself”, was named by Business Week as one of the Top 12 Business Books of All-Time.

I love James. He’s got such a vulnerable writing style, is super curious and it was great to reconnect with him.

I know you’re going to enjoy this incredible new episode with James Altucher.

Join us as we discuss:

  • Transcendental meditation, psychedelics, and Ayahuasca experiences
  • Ido Portal, Dan Peña, and break dancing
  • Crazy Legs, writing, and the hero’s journey
  • Steven Pressfield, Joseph Campbell, and Star Wars
  • Christianity, his children, and masculinity
  • Stand up comedy, J.K. Rowling, and The Marvelous Mrs. Maisel
  • Idea sex, the price of Greenland, and Donald Trump
  • College, the power of no, and his upcoming projects

“Vulnerability is a way of trading some aspect of your privacy for freedom.”

In short: James Altucher is an American entrepreneur, investor, bestselling author, podcaster and stand-up comedian, best known for the book Choose Yourself. He returned to the London Real studio in 2019, speaking with Brian Rose in New York, to talk about vulnerability, the hero’s journey, comedy, his ten-ideas-a-day habit, the case against college and the power of saying no.

The conversation opened with James turning the tables on Brian, asking how London Real grew from a one-man show into a larger production. Brian described the fear that kept him from going all in, and the day he decided to hire and invest. James then explained why he believes vulnerability builds trust: your audience can sense whether you are telling the truth, and being open about private struggles can bring freedom.

From there James walked through storytelling as a hero’s journey, his decision to take up stand-up comedy after years of public speaking, and the idea that skill acquisition spills over into the rest of your life. He described reading the room, why laughter is partly a group effect, and why he now only tells jokes that matter to him.

The second half is about ideas and choice. James explained his habit of writing down ten ideas a day, how to test them cheaply before building them, why he thinks college no longer makes economic sense for most people, and why saying no creates room for the things you love.

Key takeaways

  • Vulnerability buys trust and freedom. James said your audience acts like an x-ray machine, and sharing hidden things, as Brian did about his addiction, trades privacy for freedom.
  • Make every day a mini hero’s journey. The ordinary world, a call, a challenge and a return can frame stories, adverts and your own week.
  • Keep a fear check on your writing. James only hits publish when he is a little afraid of what people will think, because otherwise he is repeating what everyone else says.
  • Train the idea muscle. He writes ten ideas a day. The first seven are easy, he said, and the last three take most of the time.
  • Test before you build. His example is a founder who could try her service manually with five friends before raising a million dollars for software.
  • Combine fields. James calls it idea sex: Uber plus babysitters, or Scott Adams combining drawing, business and humour to create Dilbert.
  • Say no to protect your time. Each no, he argued, carves out more freedom, though he admits saying yes to some uncomfortable things has also paid off.

Why vulnerability works

James said his early writing was more open than his peers’ and drew worried emails, but he found it built trust. He described vulnerability as a trade: you give up some privacy and in return get relief, a bigger range of things to talk about, and a closer relationship with those around you. He applied this to Brian’s decision to speak about his 2001 overdose, which Brian had kept from his wife for 16 years.

On masculinity, James said being open does not make a man less masculine. For him, being honest about who you are, and not hoarding things you are afraid to share, is the point, whether you are a man or a woman.

The hero’s journey, comedy and reinvention

James described every good story as an arc: you leave the ordinary world, face trials, and return with something to share. He applied that to adverts, where the customer is the hero, and to Brian’s career move from finance to broadcasting. Brian said he used the same structure in his films Iron Mind and Reconnect.

James said he tried stand-up comedy after audiences told him he was funny, and found the first attempts terrifying. He now owns a comedy club, has performed sets of up to 90 minutes, and says the craft taught him to read a room, watch for the unusual and relax when an audience goes silent.

Ten ideas a day, execution and idea sex

The idea muscle, James said, is like any other: it shrinks if you stop using it. He began writing ten ideas for people he admired, including Warren Buffett, when he could not get meetings with them, and replies followed. He tests ideas by writing a second list of simple execution ideas, such as speccing an app screen by screen and posting it on a freelance site.

His Going Steady app idea ended within an hour after a freelancer said it would not work on iPhone. His 2019 Greenland crowdfunding stunt was shut down by GoFundMe, but he said every small experiment teaches something. He described himself as risk-averse, writing smaller cheques because he wants to sleep at night.

College, saying no and choosing yourself

Brian and James compared notes on MIT and Cornell. James argued that rising tuition, student debt that is hard to discharge and a changed job market weaken the case for college, though he said he would still pay for his children if they chose to go. Brian pointed to the discipline and social growth he gained.

James described learning to say no after years of saying yes to everything, and tied it to the main idea of Choose Yourself: if you wait for gatekeepers, they decide for you. His advice to a 20-year-old was to write ten ideas a day, and to look for ways to skip the line using what he calls the 10,000 experiments rule.

Who is James Altucher?

James Altucher is an American entrepreneur, investor, bestselling author, chess master, podcaster and stand-up comedian. He hosts The James Altucher Show, writes a widely read blog, and is the author of Choose Yourself, The Power of No and other books. He told Brian his businesses brought in around $60 million in revenue in 2018, that he once ran a hedge fund, and that he owns the comedy club where the interview was recorded. He has a book due with HarperCollins in 2021.

Frequently asked questions

What is James Altucher's main message about vulnerability?

He says vulnerability trades some privacy for freedom. Being open builds trust with an audience, he argues, and frees you from carrying secrets.

What is the ten ideas a day habit?

James writes down ten ideas every day on a chosen topic to keep his idea muscle active. The ideas do not have to be good, and the last few are the hardest.

What is idea sex?

James uses the phrase for combining two ideas or fields to create something new, such as an Uber for babysitters or a cartoonist skilled in drawing, business and humour.

What does James Altucher think about college?

He argues that rising costs and student debt make college a poor economic choice for many people, while saying he would still support his children if they chose to attend.

What is Choose Yourself about?

James describes it as the idea that you should stop waiting for gatekeepers to give permission, and create and publish your own work instead.

When was James Altucher on London Real?

James Altucher spoke with Brian Rose in New York in 2019, and the full interview is free to watch on this page.

Chapters

3:53 | Brian’s introduction to James Altucher
5:21 | How London Real grew, and why Brian went all in
8:51 | Ayahuasca, the real world and Brian’s mission
14:08 | Breakdancing, addiction and healthy obsessions
18:05 | Vulnerability: trading privacy for freedom
23:13 | The hero’s journey in storytelling and ads
31:58 | Vulnerability and masculinity
36:22 | Reinvention: James becomes a stand-up comedian
40:10 | What laughter is and how to read a room
52:59 | Should everyone try five minutes of comedy?
57:47 | Offence, Dave Chappelle and the limits of jokes
1:01:04 | Ten ideas a day and the idea muscle
1:06:33 | Execution ideas and testing cheaply
1:11:55 | Idea sex: combining ideas
1:19:01 | Staying risk-averse and trying to buy Greenland
1:25:51 | Why James doubts college
1:36:15 | The power of no
1:40:51 | Choose yourself: stop waiting for permission
1:42:13 | Writing plans and rewriting tips
1:47:09 | James’s daily practice
2:01:59 | Advice to a 20-year-old
2:06:13 | Skipping the line and the 10,000 experiments rule

Downloads

Full transcript: James Altucher on London Real

3:53 This is London Real. I am Brian Rose. My guest today is James Altucher, the best-selling author, chess master, comedian, entrepreneur and broadcaster. You host two podcasts, The James Altucher Show and Ask Altucher, and your blog, The Altucher Confidential, has over 25 million readers. You’ve written thousands of articles for The Wall Street Journal, TechCrunch and the Financial Times, and your book Choose Yourself was named by Businessweek as one of the top 12 business books of all time.

4:17 James, welcome back to London Real. In New York City. Thanks for having me back, Brian. I’m glad to be here. I’m gonna take over your podcast or your video for the first 5 minutes.

4:26 Is that okay? Yeah, I’m assuming you would. Yeah, this is James Altucher. Oh, wait, I got to at least start the show. Are you…

4:33 I know, I guess this is James Altucher. Sure, taking over for five minutes. Brian Rose’s London Real. Brian, how are you doing? It’s been four years since we last got together.

4:42 Four and a half years. I’m great, man. It’s great to be back in New York City. It’s great to see you, and it’s great to watch you take your game to the next level. Well, Brian, I’ve been watching you take your game to the next level.

4:53 Like, I feel, so you’ve been doing this for a long time, like seven or eight years, but I feel like four years ago when we met and I was on London Real, you were just beginning to really ramp and put your full resources behind it, and you have done an incredible job. Like your audience is so much larger, and you’ve really taken advantage of YouTube even more than you’ve taken advantage of a podcasting aspect of what you do. What did you do specifically to grow your audience so big?

5:21 Good question. I mean, look, I started this as just a way to connect and communicate with people, and I literally walked out of my job in finance for ten years in London and started broadcasting, and it started off as a project, and then at one point I actually had someone on my show who’s become one of my mentors, and I just thought, you know what, if I’m gonna do this, I need to go all-in. So I just decided to invest myself and money and everything in the company and just to start pushing it as hard as we could.

5:48 Why do you think you weren’t going all-in? Like, what were you doing? It was fear, to be honest, James. I think part of me was, it was like grandpa in the woodshed, you know? I was like, there I was, one-man show, I was doing all the editing myself, and I just was being conservative, and I thought, I don’t, I, you know, I didn’t have an income, and I was like, I’m gonna spend all my banking savings on what, putting money into something I don’t know is, we kind of a business?

6:08 And I think it was just fear. And then when I decided, you know what, I’m just gonna go all in on this, I’m gonna hire people and we’re just gonna go big, and ever since I started that, it’s just been, yeah, it’s blown up, and I try to remind myself that every week, to just go bigger and bigger and bigger. And so what were some of the key hires you needed to do to kind of take that next step? Hiring the first person was a real weird thing, because like I said, I was in the wood shop like grandpa tinkering with his toys, and it’s a fun, comfortable place to be, but you don’t get challenged.

6:33 So doing my first full-time hire, a first, you know, salary, and then having someone there watching me, I thought I worked hard, but when you got someone watching you, you work harder. And then the next hire, the next hire, the next hire, that was big. Just doubling up our production, starting to make movies, just always doubling down, and that’s what we’ve been doing every year for the past few years, and it’s made a huge difference. You say you’re trying to improve each week?

6:56 Like, you do, you start the week thinking, okay, this is the new thing we’re gonna try this week? Well, if you look at all of our shows, and you can watch them for eight years now, just, sorry, eight-year anniversary, so I think it’s like 500-plus shows, each one I try to get better. So the first one, that was horrible lighting, I had horrible facial hair, I was wearing skateboarding clothes, the microphones were bad, we used to split the screen, like literally with people’s faces in a third, a third, a third.

7:18 And so then the next week was like, well, maybe we should get some lighting, maybe we should get some better microphones, maybe we should get a better studio. You came when we had the brand-new studio with the chairs and the flags. Maybe we should get this kind of camera, maybe we should hire someone to help us book guests, all of that stuff. Maybe we should hire someone to help us do thumbnails, hire more people on our video team, make a documentary film.

7:38 These were all big things just to try to take it to the next one. What’s this documentary about? So it’s our fifth one and it’s called Reconnect, and it’s about three of my ayahuasca ceremonies last year in Costa Rica and the subsequent 18-month integration process of coming back to the real world and realizing that all of your visions and all the things you see that you should be is not reality and no one around you understands what the hell you’re talking about, and trying to integrate the visions you have about your family, your personal life, your business into this crazy world.

8:07 And so, yeah. Well, it’s interesting, because on the one hand, you know, take something like ayahuasca or any kind of transcendental type of activity, whether it’s meditation or, you know, hallucinogenics or therapy or whatever, and you’re very much into Transcendental Meditation and so on, it seems like one goal is to discount the importance of everyday life, so you focus on your inner life, the idea that’s the only thing that’s truly real is your own ability to find well-being and some sort of peace. On the other hand, we live in the so-called real world where you have to have goals and you look at your traffic numbers and you have to make an income.

8:51 How do you bring those two sides into balance, because you’ve been doing both very well? Yeah, it’s a crazy question. And meditation is one thing, but like an ayahuasca experience, I mean, last year I had the single most profound experience of my entire life in my second ceremony. It was also painful, extremely emotional, physically challenging, a lot of vomiting, a lot of crying, but I saw this version of the world, of myself, and all these things I could be.

9:13 And then like you said, you come back and you’ve got YouTube numbers, you got bills to pay, you got people who don’t know what you’re talking about, you got kids to feed, so trying to deal with that every single day is difficult. And the truth is, James, we live in the real world, and that’s the problem I think at a lot of the psychedelic community is people go back for their 85th ayahuasca ceremony and I’m like, what are you doing? You know, it’s like, you got to try to process this in this real world that we live in.

9:37 And so, yeah, you kind of got this vision of where you want to go and then you got where you are today, and that delta is what, something you play with all the time. And if you have a really good mission statement, which I think now we have, you can stay on the course even when the numbers don’t make sense, the YouTube numbers don’t make sense. I mean, my accountants would come to me every year and they’re like, what are you doing, Brian? I’d like, trust me, I know what I’m doing.

9:57 And it’s like only recently they’re like, oh, I guess you know what you’re doing. But it’s just having that vision to stick to the course even when all the inputs are telling you you’re wrong. Well, what, what you say, what we have to have a personal mission. What’s your personal mission? So my mission, and it took me a while, and I made it really clear when I got back from Costa Rica last year, is we decided that first of all, what I’m doing with London Real, it’s where Brian Rose ends and London Real begins is not clear to me whatsoever.

10:23 And so for me, I am the show and the show is me, and I have to be very careful who I let in the studio, including you, because these people literally change the course of my life. I mean, I dress this way because I have a mentor called the 50 Billion Dollar Man. I move the way I move because of a guy named Ido Portal in Israel, who teaches fighters like Conor McGregor and the UFC how to move. I mean, like, everything about me has changed by people that have come on the show, and so it’s just become my life.

10:49 And so for me, we have a mission, and that’s simply to create a mass-scale transformation of humanity into a fully empowered, conscious and cooperative species. And we thought about those words: fully empowered, conscious and cooperative. And everything we do, whether it’s our London Real Academy or our movies or our broadcasts or anything, has to try to take someone’s life and get them to transform themselves, period. Yeah, that’s how I think we can solve all these bigger problems we’re talking about.

11:14 It’s not about pointing the finger, it’s not about, you’re doing climate change wrong. It’s like, what are you doing to get over your own fears and your own challenges? That’s what I think is the biggest problem of today. I think, I think that’s so important because, and I agree very much with your mission, and so let me, and I agree very much with, by the way, your philosophy and who you let in the studio, like where people don’t realize it, we’re not reporters.

11:36 Like, we’re not, if someone’s in the news, that doesn’t qualify them in my view for a podcast. That qualifies them to have a little article in a newspaper. To be on a good interview podcast, you should be doing something that elevates yourself and that we can absorb some of that and our listeners can absorb some of that so that they can be elevated. That’s the goal, I feel, of a good interview podcast. Yeah, yeah.

12:00 So you had, you were on Ice-T’s podcast, and I’m super jealous, by the way, ’cause he’s one of my dream guests, and he has a great saying. He said, Brian, it’s not about to come up, it’s about to come back. And so every guest on my show, I want to see what happened after they hit rock bottom. How did you come back from the loss? How did you come back from the struggle?

12:17 How’d you come back from the tragedy? That’s something I think we can all learn from. So I agree, I don’t care if you’re an Olympic gold medalist, honestly there’s thousands of those. I don’t care if you’re a rock star, there’s thousands, videos, but do you have a lesson you can teach us? That’s how I invite people on my show.

12:30 So with fat, with, and I deal with this as well, with over 500 guests on London Real and super performers from every area of life. I mean, I love your show. What, how do you think you’ve changed? Like, how do you do, it’s hard to know what you would have been like if you hadn’t had these 500 guests, there’s no way to speculate on that, but what do you do to make sure, I mean, you can’t take, like I’d say each of the five hundred people have ten suggestions, you can’t take five thousand suggestions and automatically incorporate it into your life.

12:58 How do you decide, okay, this is useful for me, I can practice this, I can try this, I can get better? I don’t think I consciously decide. I think a few years ago I looked at myself and I said, wait a second, something’s going on with you. And, you know, like I said, we had this Academy and we were teaching kind of a business accelerator course for a while, and then someone said, Brian, why don’t you teach something more about life? And I started looking at all of my habits that I picked up over the years, and I was like, wait a second.

13:22 And I deconstructed each one down to the person that came on my show, from Tim Ferriss talking about low media to someone talking about meditation to someone talking about gratitude, me and Alex, I contacted my gratitude and all these people, and then I deconstructed it. So I think it’s subconscious, I think you just picked these things up. But let me tell you a few truisms, James. I have two young boys, a two- and a three-year-old, they would not be born if it wasn’t for London Real, period.

13:44 There’s no way I would have allowed the love of these people in my life. Last year I made a movie called Iron Mind, where I did an Ironman race and I confessed about my heroin addiction and overdose in New York City in 2001. I hadn’t told my wife in 16 years that information, and now I talk about it freely. I would have never talked about that, and it would have been down inside me, is this thing I was holding on to, James, and I don’t think I would have been free to fully live my life.

14:08 So that’s another example. I’ve been sober now for two years, not having had a drink of alcohol, and again it wasn’t like I was completely out of control, but it was like, why am I doing that when I need to be more high-performance? So that’s the thing. I move every day, I’m a breakdancer now, I mean that’s crazy, I’m 48 years old, but I’m literally one, I’m a breakdancer. Good, man.

14:28 All right, I learned in London when I was 12. Really? Yeah, we got to talk. I had Crazy Legs on, the guy from the Bronx, he was in, he was in the movie Breaking, right? He wasn’t, he wasn’t Breaking, the other one that took place in New York City.

14:43 Yeah, yeah, was that the opening scene at the dance club? What was the breakdancing movie? Those in tears, beats me. Yeah, yeah, it was also in Flashdance, it was last when she did the back spin, at the last move. He was in the beginning of it, he also, he put a wig on and he was the girl in Flashdance when she did the back spin.

15:00 Now did I know that? I final dance performers in a sigh, he was an aside, a scene in Flashdance where she’s just walking by and it’s dancing on the street, the Rock Steady Crew was there. The last part of that act was Crazy Legs in that. Yeah, so crazy like that. Then there was, um, there was a couple like famous breakdancing names from the Rocks, no, the guy from the Rocksteady was there as well.

15:20 Yeah, so I’ve had him on, a guy named Storm, who’s a German breakdancer who kind of brought it all back about 10 years after Rocksteady did it. So yeah, I’ve been super blessed. You like popping? I’m John, he’s an LA-based guy, really good at, like, popping. No, I mean, no, and I’m not, I’m cool with the popping and I just focus on breaking.

15:34 Right, well, okay, I’m more in the popping than the breaking. And popping, it’s good to like distinguish the two, but breakdancing’s very hard, man, it’s such a physical thing. Yeah, and I’m on the floor all the time, but I got a windmill, I got some skills. I never could get to, in those three years to get a windmill, like I mean three years of training, three or four times a week. So yeah, I’m inspiring, I’m gonna try to do a windmill.

15:55 Yeah, I tried really hard back then, and I was a kid, I was a teenager, I should have been able to do it, but I couldn’t do it. So mentally challenging, it doesn’t make any sense, you’re rotating, everything’s flying around, it took me a long time again. But that’s me, I’m just kind of relentless on that, which can be good with breakdancing, bad with heroin. So you know, he got it, sometimes I don’t know when to quit. Well, well, that’s just it, is that clearly you have an addictive quality to you, and you know, some people, there’s all sorts of things you get addicted to.

16:27 Some people when there’s, when they’re trying to find meaning in their lives and they can’t, I think they fall to heroin or other drugs, but then there’s so many productive addictions, doesn’t mean those are great, it’s not good, like you could be addicted to something even healthy, for you to be addicted to reading, but that might not be unhealthy for you, that might be unhealthy for your life, like for instance if you’re avoiding, you’re failing because you’re reading too much. Yeah, that’s not a healthy addiction even though it seems that way. So you always have to be careful, like I always notice for myself if I’m playing, so I get addicted to stupid things, like I’ll get addicted to playing chess, but I’ll play it 24 hours a day, like one minute speed chess on the computer, and I usually am, I try to be meta aware that, oh, this has slipped into addictive territory, it means I’m avoiding something else in my life, even though everyone else would say, oh, that’s so smart, chess.

17:17 It’s not if you’re just playing it all day long, one-minute chess on the computer, and you can’t talk to your kids or family or whatever. Yeah, if you’re using it as something to not process feelings or to avoid the real world. Yeah, it can be shopping, sex, a Netflix, chess like you said, or it could be a drug, but if you, if you can just say, all right, what am I doing here? Am I doing this to not be present, to not be with these feelings? So, and I’m still learning, but there’s also healthy addictions and unhealthy addictions for sure, and the unhealthy ones are something I like to avoid.

17:47 Yeah, yeah, well, okay, I’ve taken over your podcast enough. I really wanted to at least make a dent in some of the questions I’ve had for you. We can’t go back, I don’t think so. I’m just gonna keep it rolling. Um, you know, James, something with you that I always teach my students is, you are our poster child for vulnerability.

18:05 And I have, like I said, an academy, and I teach people business and podcasting, public speaking, and I always say, you can’t get vulnerable, you’re not gonna be able to connect with the audience, and I always mention you, and it’s always like, look at James Altucher, look at almost every blog I’ve ever read of yours or anything, you’re always telling us about how you started off in a failing scenario, and I was one of you. Talk about why you’re so comfortable being vulnerable and how far that’s gotten you, and do you think it’s a good tool for people to use? Uh-huh, yeah, that’s such a great question and so interesting.

18:36 I don’t know if I’ve thought about it exactly that way since some time around 2010. I was always a little bit more vulnerable in my writing than a lot of my peers, but you know, if you go, I was a financial pundit for many years, you know, I’d go on CNBC, I would dress in my suit, and I would talk about, with four other people in this big box of people, I would talk about what my feelings were on the economy and so on. And once I started being more vulnerable, oh, these times I went broke, these times I was suicidal, these times the IRS closed down my house, or I lost my family or whatever, people would always write to me at first and say, are you about to kill yourself, or did you have a brain tumor, or no one’s ever gonna invest in you again, you’re revealing all this stuff.

19:24 And what I found though was several things. One is your audience is an x-ray machine. They know, your listeners know, even if they don’t know it consciously, they know if you’re telling the truth about yourself or not. People, you know, only ten percent of communication is verbal, the rest, 90 percent, is nonverbal. So people know there’s something else going on here but I can’t put my finger on it, and they’ll react that way whether they’re realizing it or not.

19:52 So, so to build, so a, to build trust and transparency, you have to be vulnerable, and then people say, oh, what you see is what you get, I see this guy and so I trust what he’s saying. But there’s another thing too, which is, you know, I think the word privacy has become this weird word lately. It’s almost this like legal word, like, oh, do you have privacy or no privacy? But vulnerability is a way of trading some aspect of your privacy for freedom. So for instance, when you talk about heroin, that was a very private thing for you, right?

20:29 You said you held on to it for 16 years and didn’t even tell your wife, let alone your audience. And so you traded that aspect of your privacy, and what did you get for it in return? You got freedom. Now there’s more topics that you could talk about, there’s more things that people know they can relate to you on, your your wife and family have a new comfort level with you, that they understand you at a deeper level. That’s real, and I’m sure you felt it.

20:52 This is freedom. And so you, it literally was a transaction. You took a chunk of your privacy, and you just, like you might trade, you know, dollars for some object, you traded the currency of your privacy for freedom, and I bet you felt that way. I bet you felt relief, because someone who is out of jail suddenly feels more relief, oh, I’m free. And I bet you your audience grew, because now people saw there was this whole extra dimension to you that you were hiding, and this discomfort that they might have felt with you before was gone.

21:28 Yeah, you know, very much so. It was scary as hell as well, but there, enough. Yeah, I try to always, whenever I write something, I just refuse to hit publish unless I’m afraid of what people will think, or at least what some people will think. So there has to be a fear component, else I’m just publishing the same thing everyone else is publishing, like, here’s my ten rules for leadership. A million other people have written that, so I can’t write that, I can’t, there’s no fear there.

22:04 I have to write like, here’s the ten ways I was the worst leader, people hated me, and what I learned from it. So now there’s some, I might be exposing some things in that that people might even find repulsive, he did that as a leader, but we’ve all been there to some extent in our own life. So, so again, you know, it’s part of also the art of storytelling, is to be a little bit afraid of, you have to surprise yourself in order to surprise the reader. And then there’s a third level, which is totally just about writing and storytelling, which is you want everything you do to have the arc of the hero.

22:43 So when I failed, living, you and I, as you know, I’ve kind of gotten broke and failed and been despondent several times over the decades. When I’ve been in a moment of failure, it’s because I was sort of really scared of what people would think. I was living the same, I was living in some other guideline, you know, some other path that somebody told me, like, oh, you have to go to college and then start a business and be successful, and once you’re successful, you’re smart, no one should ever know that you’re stupid.

23:13 So I was afraid to let people know that I didn’t go on this straight path. So that’s the ordinary world, and then you know, in the arc of the hero, you go from the ordinary world to the extraordinary. The extraordinary is when I admit failure, and now I have to go on this very unusual path to find my way back, and that’s going from the ordinary world to the extraordinary. And then along the way you have bigger and bigger problems, and you meet your new friends and people who will help you, until finally you have the greatest crisis of all, and you bring it back to tell the story.

23:49 Like, you bring it back and you have a podcast or you write an article or whatever, and that’s the full arc of the hero. So, so to some extent it’s also good storytelling. If I just say, hey, I’m the greatest person ever, listen to me, that’s a horrible story. Do you think, I just read a book by Steven Pressfield called Nobody Wants to Read Your, and I quoted him in my TED talk, because The War of Art was a big thing with that concept of resistance. Do you think every great story is a hero’s journey?

24:16 Absolutely. Yeah, think about this. What he says, too, yeah. And, and you know, he makes a good point in that book that, and also another book on the artist’s journey, where the artists themselves are going on a journey. You know, somebody starts off thinking, oh, I’m gonna write a best-selling novel, even though they’ve never had any experience, they just see this path that, oh, J.K.

24:37 Rowling made a billion dollars, and then they, now the call to extraordinary is, I’m gonna be an artist, and that is a brutal task. Even doing London Real for eight years, and it’s still an ongoing task to improve your artistry, and happens in every single area of life. And so the artist’s journey matches the hero’s journey, but if you think about it, even an advertisement is the hero’s journey, not for the company but for the viewer. So like, let’s say, I don’t know what the latest batch of ads is, but let’s say, you know, it’s a car ad and a handsome guy and a beautiful woman are driving in this car on the desert, and whatever, they fade off into the sunset.

25:20 So the company is not the hero in the story, the car is not the hero, the passengers who we relate to are the hero. So my ordinary world might be, I’m stuck at a job I don’t like, in a life situation I don’t like, but now here’s this call to the extraordinary: I could buy this car and suddenly I look better and healthier, I’ll be with someone who also seems great and healthy, and we’re driving off in the desert, escaping this bad life situation that I’m in. So, so look, even companies should think this way, not that they’re the heroes, but their customers are the hero, and their exposure to your product is their beginning on the hero’s, the call to the extraordinary is when they see your product for the first time.

26:07 Yeah, no, I totally agree. Do you think that’s in our DNA somewhere, like the hero’s journey? You know, I always wonder this. I mean, Joseph Campbell, who first kind of coined the term in his book The Hero with a Thousand Faces, he would argue it was primal because if you look at all the mythology going back 4000 years, I mean, Jesus perfectly models the arc of the hero. Yeah, you know, and we all know Star Wars is related to the birth of, you know, the story of Christianity.

26:36 Moses is the arc of the hero. There’s so many arcs of the hero going back thousands of years. You think maybe it’s primal, but I would not, I can’t even guess why it would be primal. I don’t know. Yeah, I think it’s why, because stories used to be our primary way of teaching, right, before books and academies and universities, and so it is something that resonates with people, with us, because it teaches lessons, those lessons allow us to survive.

26:58 So, and I had Dr. Jordan Peterson on the show, and he thinks, you know, he talks about the Bible, you know, that that is somehow in our DNA, this is just some biblical book, but it’s like stories for life that keeps us alive as a human species. Yeah, like I don’t know if you ever saw his video where he breaks down Peter Pan and how it all relates to our need to be a child, that comfort of first being in the womb and then being cared for by our parents, that feeling of fun and the sandbox, but that ultimately really the calls to the extraordinary needs to become an adult. And you know, I love how he breaks down every story into its kind of mythological elements, and he’s a genius.

27:39 Yeah, he’s really good, and I’ve thrown him in our latest film as well. So what I do is take the guests that come into London Real Studios and we’re making a film, they just become part of the films. That’s great. So yeah, so I used the hero’s journey as well, our movie last year Iron Mind. So I, the call to me was to come to New York City and train with John Joseph and do the Ironman.

27:56 Of course, I refused the call at first, ’cause like, what am I, I’m busy, I can’t do an Ironman race. Then I accept the call, I go through all the trials and tribulations, the training, difficulty with my family, and then I go run the race, I finished the race, then I come back with this new knowledge of, you know, getting over my shameful addiction and all this stuff in the past, and new questions. And we’re using the same structure with our latest movie, Reconnect, with ayahuasca being like the calling.

28:20 I refuse the call, then I go, I drink the medicine, I have all these trials and tribulations, then I come back with this new learnings of, okay, you know what, what do we all need to do to make this world a better place? So it’s a great structure, it’s typical, it’s I’m did in 2015 when I met you. You had a great arc, and I’m not saying it’s almost as when we kind of define it so much that it’s disingenuous, like we did it on purpose, but you had this arc of your, this Wall Street banker who was dissatisfied and decided to have a higher purpose in life and reinvent yourself and started London Real.

28:55 That was a call from the ordinary to the extraordinary, and then you, like you said, you started hiring people and building it up, and you know, finally lived to return to tell a story of what happened, and through London Real and your documentaries and so on. So that’s the perfect arc of the hero. And I think, I think it’s not so much to say, fit your life into an arc on purpose, it should just, you should just ask yourself, baby, am I, am I the hero of my journey?

29:23 Like, how can I, what can I do today to have, even in a microscopic way, something that is a mini call from a mini ordinary to a mini extraordinary? I think it’s an interesting challenge to the addressing exercise. I think it’s a great exercise and something I ask all my, and my students to do on our public speaking course. I’m like, tell me your hero’s journey, and most people say, I don’t have one, I’m not a hero, I’ve been mediocre my whole life. It’s like, no, you actually have a hero’s journey, so just tell me one.

29:50 And if I really think about it, I guess that one time I did this and I win, I learned and I came back, and so it’s a good exercise to show everyone that they are a hero in some way, and I think everyone has multiple hero’s journeys. I was like, say I could tell the hero’s journey about me trying to get here today and, like, woke up, I was like, I gotta go see James, oh man, what are we gonna take, the subway or my gonna take the taxi? I struggled here, and then I got here, and then boom, I’ve got this great knowledge of the transit system, you know?

30:15 So there’s so many different ones. It’s right, oh, I think that’s a great exercise, which I’m gonna start doing today, which is how to make every day a mini arc of the hero, because it’s there, it’s always there, and if you think that way, I think, well, I don’t know, we’ll have holes, see what happens, it’s that’ll be my next experiment. So this is writing tips from James Altucher: is vulnerability forces you to basically follow the hero’s journey arc, because when you start with some vulnerability, you’re kind of putting yourself in that position.

30:44 Yeah, hopefully you teach someone by that vulnerability, I got to this level, and you come back out, the gyro, right, those two, it’s kind of when you were sharing a vulnerability, there’s two arcs in here. Oh, there’s the initial one that you’re vulnerable about, you know, going from a heroin addiction to it to not being a heroin addict, and then there’s the being secretive about it to not being secretive about it, because that’s a whole other journey. And then there’s this idea again, not just on storytelling but just in terms of your own personal freedom, which we all aspire to, being vulnerable again trades some aspect of your privacy that you were holding tight to, like you were hoarding it in the bank for no reason, it wasn’t gaining any interest for you, it was almost like negative interest.

31:27 So you were hoarding this aspect of your privacy and you trade it for freedom, which has so many more benefits than hoarding it. So, so I think that’s an important thing to realize, also like particularly with privacy being such a, this regulatory catchphrase now. Let me ask your question. There’s a bunch of people that are talking about masculinity these days, and I’ve had people like Elliott Hulse on my show and I’ll have more people in the future, and some of them, I’ve seen them on Instagram saying, you know, men shouldn’t be vulnerable for the sake of being vulnerable, and they should still be masculine.

31:58 How do you, what do you say to that? Well, when they’re saying it, they’re probably right, like they shouldn’t be vulnerable for the sake of being the opposite of masculine. Seems like they’re kind of relating vulnerability to the opposite of masculinity, and without defining things like, you know, toxic masculinity, femininity, messaging, I think, you know, being free allows you to be yourself. So if you’re a man, then you know, being who you are and honest about it allows, like for this, I’m not gonna run an Ironman probably anytime soon.

32:37 Does that make me more or less masculine? In some ways it makes me less masculine, so I’m not gonna have the same testosterone, you know, when you’re running an Ironman. And yet I feel very masculine just in that I’m very, well, I don’t know, the whole gender definition thing is very weird and it’s so much in the news these days, but I feel very masculine just by being exactly who I am, being myself, saying who I am. It doesn’t mean saying who you are is masculine.

33:06 If you’re a woman, being who you are and being free and being vulnerable, that’s feminine for you, and for me it means being masculine. I don’t really, I don’t really like all the fact that there’s, or something, it’s not that I disapprove of this, but I don’t believe in 63 shades of gender. There’s, I saw one poll, there’s, they identified 63 different genders out there, and I think that’s interesting to observe, but I can only be who I am, and I don’t know where I am on that gender scale.

33:38 I view myself as a man, and I think being vulnerable just simply allows you to maximize who you are before you die. You don’t want to, you don’t want to die, it’s just like you don’t want to die with a billion dollars in the bank. Like, you worked so hard to make a billion dollars and then what for, when you die and it’s still in the bank and you didn’t do anything with it, it was just all sort of pointless. You don’t want to die with all of these, all of this privacy in the bank when you could have instead experienced all the freedom it could have gotten you if you had shared it.

34:11 And I think that’s very important, to be the best who you are, whether you’re a man or a woman. Probably there’s some toxicity in general in life by hoarding all of these vulnerabilities and not letting people see who you really are. I think that’s probably toxic, rather than toxic masculinity or toxic femininity. I think toxicity in general comes from, you know, keeping, hiding things and and not trying to improve and so on. Yeah, and I’ll just say, if anybody’s out there that thinks that they have something they could never tell someone, I had this big dark black hole that was down in my belly for like 16 years, and I thought that that horrible experience I had in New York City would never ever be anything but bad, and then once I expressed it, it became this source of light for so many people.

34:58 And someone, he wrote me emails and said, yeah, I started with, struggled with pills, and my father struggled, and all these things, and it became this way to uplift all these people, and I never thought that would have been possible, James. Yeah, because self-help is meaningless, but when other people see how you helped yourself, that becomes meaningful, because then they can see, then they’re, their mirror neurons say, oh, he did it, and he’s sharing this story, and he’s doing fine, and it was my, it might have been uncomfortable to share those things, he maybe he lost friends, he maybe lost family, he maybe lost his friends from back in the day, but he gained something new by sharing this. So, so again, I think it’s this act of sharing makes you better, and people are helped by seeing how you helped yourself, then they get this sense of what to do, rather than reading a self-help book, oh my gosh, I gotta clean up my room now and make my bed and do this, this and this because someone says so.

35:55 They, they get, they get to decide for themselves. Ultimately you can’t improve unless you’re deciding for yourself, rather than just, you know, absorbing information from someone else. Let’s talk about reinvention, which is something you’ve been talking about for a long time, and you as well, you’re a great reinventor, breakdancer, what the hell, how did I expect that? It’s so much fun, reinvention, but like we’re literally sitting in a place that kind of is, just described your reinvention in a big way, because it’s a comedy club.

36:22 Yeah, you own that you regularly perform at, I’ve seen your videos, and I mean, years ago I don’t think anyone would have thought James Altucher would have been a stand-up comedian, though although people were laughing at my public talks. Everyone was saying to me, you know, everybody, ever talking, I don’t know, 2008 to like 5,000 people about finance, and at the end, a lot of people came up to me and said, oh, you should be a stand-up comedian. And then in 2014 or 2013 I gave a talk, and a very famous stand-up comedian was right after me, and everyone came up to me afterwards, I said, oh, you were so much, I’m not, I’m not bragging when I say this, that’s why I’m not saying his name, you were, you were so much funnier, you should definitely try this.

37:00 So I tried it and it was horrific, not that I was worth it, but just the, the terror was, I’ve been doing public speaking for 15 years at that point, that terror was unbelievable to do five minutes of stand-up comedy. And here I write humorously, I do public talks, I’m sometimes funny on TV, but doing stand-up in a club, but to a bunch of strangers, that is or was extremely terrifying. And I, Joe, I’ve always been a fan of comedy, I even worked for HBO, which is a well-known channel in the US, I worked for HBO Comedy for a while, and I always respected it as an art form, but I was always too terrified to actually do it.

37:46 And then I felt like, oh, I could do what everyone says I could do, it’s just totally a different thing. And then once I realized that, and I realize I still love it, I figured, you know what, I’m gonna, I love skill acquisition for things that I love doing, and so I really wanted to get better at this very unique art form. And so it’s just been, you know, I keep, I keep track of everything else, like my business, am I writing, my podcast, my family, but this skill acquisition has become so important to me, and I’ve seen it reverberate into all other areas of my life as well.

38:23 How such a pleasure, well, with stand-up comedy, and you’ve seen this more lately with the intersection between stand-up comedy and a lot of the political and public conversation about what’s important in life, but with stand-up comedy you’re kind of training yourself first and foremost to observe unusual things. And so a lot of people will just live life and this is normal, this is, you take shortcuts so that life, so that your thinking is as easy as possible, you won’t notice the interesting or the unusual because it’s usually not so important to notice these things. But when you start to make it a practice, like that, everything around you could have the unusual in it, the world becomes a different place, and you, and it gives you more material to think about, to talk about, to write about, to observe in yourself.

39:15 And then if you take that extra stretch of, you could communicate in unusual things in two ways: you could just write about it, and that’s fine, or you can put this weird punch line on it that connects it all the way back to something else, and everyone listens and they laugh, because you just took something that they didn’t think was unusual, you made it unusual for them, so now they’re tense, and then a punch line releases the tension, so now they’re comfortable with this unusual thing you brought up, and at the same time they have more knowledge, if you’re doing it right. Sometimes you can just tell a fart joke and that’s funny also, and that makes people laugh, and laughter is good for health. But the best stand-up comedians are taking something they find fundamentally unusual in society or in life and they stretch it to the point of tension, and it may twist it so that everyone laughs, everyone relaxes, but they leave with something new.

40:10 What’s happening when people laugh? Uh, you must have thought about this. Yes, and there’s a lot of research as well. So for me, one thing I’ve noticed too is that I was able to take other, as I learned stand-up comedy, I was able to take other aspects of my life and kind of skip the line in terms of learning stand-up comedy faster. It takes a long time to get to, get good at this art form, but I was able to, you know, take my analytical skills that I’ve learned from doing hundreds and hundreds of podcasts or starting businesses or investing, you have to be very analytical, as you know, to be a good investor, to be a good writer, you have to really analyze, like, every word, you know, you have to read other stories, what are they doing?

40:53 And so I watch other professional comedians analyze every aspect of what they’re doing, then the benefits of a podcast, I get to have them then on my podcast and ask them all the questions I didn’t understand about their recent performances. So I’m very analytical, and I was able to bring that into my stand-up comedy skills, and part of being analytical is understanding what laughter is, and I think what it is is that millions of years ago, chimpanzees, which don’t speak a normal language as we know, they would hear rustling in the bushes and they would all jump up into the trees, and then once they realized the rustling was just the wind and not like a lion or a bear or whatever, they would start making a noise that sounded like laughter, and that would relax everybody, they would come down from the tree.

41:47 So I think that’s the evolutionary roots of laughter, and so as a consequence we’ve evolved that laughter becomes this really healthy thing. The more, and there’s a lot of research on this, the more you laugh, the less inflammation you have in the body, the less disease is related to old age that you have. And I think it’s, I think it’s because we’re, body rewards us for these times millions of years ago when we were safe, this, but the chimpanzees that paid attention to laughter survived, and then we evolved as a result of that.

42:21 And there’s a group dynamic as well, which is why they put laugh tracks in the TV shows we used to watch when we were kids. I mean, when other people are laughing, you kind of also want to laugh, right? And so, so that’s a great thing to, like, when you’re about to perform in front of a group of strangers, first off, every room is different, every, you can’t do the same act twice in a row. When you walk into a room full of strangers that, they don’t know you and you’re going on stage and their only expectation is that you might make them laugh, and your expectation is nothing because you hope to make them laugh but you have no idea, so you have to, so, so a, you have to have this, you build a skill of reading the room, which was very different when I was just public speaking.

43:05 You still have to read the room, but not as much. Like, I only had to read the room enough to know, okay, they’re interested in this topic, here’s an approach to this topic that will keep them interested. But you have to very carefully read almost every, like if there’s a thousand people in the room, you kind of have to see each person and who’s gonna laugh, who’s gonna be a problem. But sometimes a room is seated in such a way that there’s like empty spaces, you know, if the club is not crowded, and it’s not just this club, I’ve even performed in The Comedy Store in London and all over the country and all other clubs in New York City.

43:39 You know, sometimes the way people are seated will prevent laughter from going viral. Sometimes if these people are tourists from Sweden and these people are tourists from Venezuela, they might not, you know, their laughter might not go viral, so you have to figure out how to build, literally it’s called try building, you have to figure out how to build a try between these two tables so their laughter could go viral. So all of these kind of persuasion techniques, you know, play into how you’re gonna get people to laugh, even if you know your material is exactly the same.

44:09 You have to do different things to kind of make your material work, or you don’t use your material and you just play with the audience. You have to read the room very carefully, but, but yeah, and the other thing is to hear, like here’s an interesting thing, if you’re making jokes that are a little bit edgy, you have to make sure the women in the room are laughing, particularly if they’re there with a date, because the date will look toward, is my, is the woman laughing? So that gives me permission to laugh.

44:36 So, so you, you know, and there’s another interesting two to it, which is, um, kids laugh three hundred times a day, but the average adult laughs just five times a day, and you know, because I guess we have more responsibilities, we’re not just playing pranks on each other anymore, we have more fears, we, we deal with more stressful people, we have more stresses in our lives. So when a group of people come in to a club, and let’s say you’re the first act, they’re not yet warmed up. Now you’re asking them to laugh another 300 times, it just laughed only four or five times during the day total.

45:10 So you have to understand where you are in the lineup and where the audience is. So there’s so many factors that come into play, and in just that one thing you said, laughter, and sometimes you have to also realize they might be enjoying the act, they’d be smiling, and you might be killing it even though they’re silent. And so there’s all sorts of things you have to be aware of. Then you have to be aware of, am I panicking right now because they’re silent?

45:34 They’ve been silent for 15 seconds, am I doing something wrong? And then you have to make sure, you know, you relax your shoulders, you slow down. The tendency when you panic is to speed up and to crouch over, but you have to do the opposite of that. You have to be self-aware. Yeah, you mentioned kids, like, I have two and three-year-old boys and they laugh all the time.

45:53 I mean, they’ve taught me that it’s just a natural human thing, but you forget. Yeah, I mean, you, the streets of New York City, there’s not people laughing all the time, so you know, you forget it is a really natural human emotion, and we like to see the discrepancies and things and things that resolve, and that makes us laugh. And yes, and they laugh over just the stupidest things too, which is funny. Like, I like silliness on stage and, you know, trying different things, like, you know, comedy, like any other art form, I don’t like it when comedians just do the same jokes over and over again for years, because it gets, because they even get bored themselves saying those jokes, they’re just trying now to survive rather than really you know, engage in the art form.

46:36 So you see even someone like, you know, and this is a trap for any art form, like podcasting or writing or TV, like you see J.K. Rowling, you know, after so many Harry Potter novels, she had to reinvent her art form by writing a mystery novel. You know, I’m sure over the years you’ve evolved, you know, the way you interview and how you interview and what you’re looking for in an interview, and maybe even whether or not you interview, like you started doing documentaries.

47:02 So you know, every art form has to evolve so that you, that you grow personally, you know, and again you have to always increase those powers of observation, powers of looking for the unusual, the technique of twisting something into a laugh. It’s just, it’s just a fascinating art form. So about ten years ago I took a stand-up comedy course in London, this is before London Real, and I took it at night over like six weeks, one of the hardest things I ever did.

47:29 I’m not naturally someone that goes on stage, I’m more introverted than extroverted by far, and I remember getting up and the guy’s like, why do you want to be a comedian? I said, if you can do stand-up comedy, you can do anything. I remember saying that because again, like you said, you’re going in front of a cold audience trying to make them laugh, and I remember some of the things they said is that right away they said, if you don’t address your American accent in London in the first 30 seconds, you’re gonna die.

47:53 And there was another girl with super short hair and they said, if you don’t address the fact that you look like a lesbian, you’re gonna die. And it was just like, funny how they said that. You got at least called alpha in the room and then break the tension and get to where you’re going. Yeah, you have to always address what the crowd’s thinking, right? So for instance, if they’re simply ordering drinks and you’re trying to talk over them, it doesn’t work.

48:14 You have to, you have to almost make a joke out, you just have to say, you know, I hope by the end of tonight I’m as drunk as you are, keep on ordering, or something, you know, something stupid that just calls it out, and it breaks the tension of everyone realizes you’re trying to talk over these people. So you have to, like, address the elephant in the room. Or sometimes I’ve done a very serious podcast, you know, on the stage, and then immediately after there’s a comedy show that I’m on, and so I have, the elephant in the room is, I was just really serious in a podcast, now I have to tell you know, these jokes about something completely different.

48:45 I have to address that. Yeah, yeah, so you got to really be comfortable. How are you doing when it comes to stand-up? Uh, I think I, I think I am doing well. I think there’s always the danger in anything, there’s something called the Dunning-Kruger effect, where you start an activity and your cognitive bias is to think you’re better than you are.

49:04 So like most people think they’re better, you know, I think there’s a study, 9 out of 10 drivers think they’re above-average drivers, and for any activity that people care about, they think they’re better than they are. So I think it was a hard learning experience. I thought comedy was about just humor, but it’s not, it’s about reading the room, it’s about stage presence, it’s about likability, it’s about all the different types of humor, you know, crowd work, you know, how you tell a story, how you’re gonna end.

49:37 So there’s all these sub-skills that were mutually exclusive to each other and I had to learn each one of those, and I think just now, really, let’s say in the past few months, I’m starting to get to the point where I got to the point where I was doing well regardless of the audience, and I can go up on a lineup of pros or semi-pros and the average person couldn’t tell which was which, but I wasn’t happy. I was telling, I still thought I was telling jokes just for the humor and they weren’t quite meaningful to me. So now I’m being very strict with myself by only telling jokes that are meaningful to me, because then if they don’t respond, at the very least I’m saying something I think is important, like a social commentary.

50:23 Yeah, okay, and then I can go back and then I watch the video of what I did, I can go back and work on the punchlines, but as long as I’m saying things that are meaningful to me, it’s probably meaningful to someone else as well. So now I hear much more often in the audience someone laughing and saying to whoever they’re with, oh, that’s so true, that’s so true. So I’ll talk about something I never used to talk about, like I used to write about this all the time, which is I don’t think my kids should go to college, and but I think for some reason I never, the first three or four years I didn’t have that in my stand-up comedy even though it’s been in a lot of my writing, and so now I’ve been being able to incorporate it into my writing, into my comedy, and it’s much more interesting.

51:04 I got able to make jokes out of it, people laugh, everybody relates, so it’s fun. So stuff like that. So I have like twenty issues that I’m outraged by, and I’m finally able to bring it into my comedy as opposed to just some dumb joke that I know will make people laugh but I don’t care about. Yeah, is the Netflix special coming soon? You know, that’s the other thing too, is I have no goals, so I don’t know, like, take your breakdancing for instance, I’m I’m guessing you don’t have the goal of winning the World Breakdancing Championships, but it’s just a fun artistic thing to do.

51:41 You probably love the subculture and the music and the physical activity, I do as well, and for comedy I try to always check myself, like I’m not competing with everyone else who’s 25 years old who’s trying to have a career as a stand-up comedian, I’m just trying to get better every time I go up and learn from it, and I have no other goals other than that. If something happens, something happens, but I really don’t, I might even reject goals depending on how much work it is, because I have other things that I do too. Yeah, and I’m totally with that, and I’m a big fan of goals in certain parts of your life when you’re trying to go places, but um, yeah, that’s what I do when I go breakdance, I’m just trying to get better.

52:19 I’ve got ten and I’m trying to get better, and to the outside it might look like I’m falling on my face, but for me I’m getting better in these few things. Have you done longer sets than, like, five minutes? Or yeah, I’ve done up to 90 minutes. Really? Yeah, in Houston at a place called the Joke Joint, I did 90 minutes, two weeks later the Joke Joint went out of business, I don’t know if they’re connected or not.

52:38 Correlation, causation, right? But 90 minutes was the longest, but I’ve done several times 60 minutes, and I can, you know, easily do 20 to 30 minutes every time. So I did my, I did 20 minutes last night, for instance. Okay, that’s what do you think, everybody should get up and do five minutes of comedy? Well, it’s interesting, you know, you know the show The Marvelous Mrs. Maisel?

52:59 I’ve heard of it. Yeah, it’s on Amazon and it’s one of the more popular shows on Amazon, it’s about a woman in the 50s and early 60s who attempts stand-up, and one time I ran into the actress who plays this woman, and in its third or fourth season, I don’t know, and she plays a stand-up comedian, and I said to her, oh, if you ever want to use Stand Up NY, the club here, to practice your stand-up, feel free, come in anytime. And she said, oh no, I would never do stand-up comedy, I’m too terrified to do it.

53:30 And I thought that was really interesting, that she’s portraying a stand-up comedian on the show but is too afraid to try it, so she knows all the nuances but is afraid to try it for herself. It’s a real terrifying thing, and I think, I don’t know if everybody should do stand-up, but everyone should a, do things that terrify them and challenge them that they’re interested in. I’m never gonna skydive even though that terrifies me, but see, stand-up comedy terrified me and I was disappointed in myself that I hadn’t yet done it, so I was able to try it.

54:02 And there’s a skill, not doing it once but doing it over time, again there’s the skill of observing the unusual in everything, even small tiny things, you just start every day observing things. Like yesterday, this is something I don’t know if I’d incorporate it into comedy or not, but I didn’t realize that Uber drivers rate you. I didn’t know Uber drivers also rate me. I always thought the reason I get to pay more to take Uber is I’m paying for them not to observe me and review me.

54:35 And then I’m telling this to my daughter and she said, oh yeah, of course Uber drivers rate you, and she shows me her rating, she’s like hugely rated more than me, and I’m like, you don’t even clean the dishes, like how do you, how is this, Uber driver, how are Uber drivers rating you higher than me? Like I’m you’re kind of a mediocre person, and I, you know, I at least, you know, clean the dishes, take care of people, pay for your college, do podcasts. Yeah, so, so it’s just this is just an observation that’s unusual to me, and I don’t know where, if it plays a role in comedy or not, but we’ll see.

55:13 It’s exciting stuff. I did two five-minute sets and they were exciting times for me. The first one was in front of, like, the final comedy class. My girlfriend, who’s not my wife, was in the front row, I think she was deeply offended by something I said, was yelling at me afterwards. And then that’s the start of a hero’s journey.

55:29 Yeah, and then in one, I just went out to a comedy club and I was the last set, it was like 15 people went ahead of me, and I went out, but I have it on tape somewhere. And oh, you gotta send it to me. Yeah, it’s, I mean again, once you perform for a cold audience, that’s different. And I know that is Brian Rose from London Real, I can perform in front of London Realers and, like, honestly, I could fall on my face and make funny animal noises and that they’ll think it’s cool, but when I go to a cold audience they’re just like, who the hell is this Yank, why are you on my stage?

55:55 So it’s good to know the difference between those two audiences. Yeah, no, absolutely. Your connection and was not, your, if you’re there with your friends and viewers and readers and so on, hey, you can go deeper into stuff you’ve already talked about there already, you already started a conversation with them a long time ago, so you can kind of make jokes at the fringes of that conversation or call back to other London Real episodes or other things you’ve written or whatever, so it’s an easier audience.

56:23 It really is an easier audience. But it’s funny about what you said about your girlfriend being upset. One time I did a 60-minute set and I thought I killed, like everybody was enjoying it, they were congratulating me afterwards, it was the first time I had done sixty minutes and I was so happy, and then at the end my girlfriend, now ex-girlfriend at the time, she was yelling at me about something, one thing in the sixty minutes I had said, and just totally ruined the evening for me, until I realized, you know, I can’t let her be the thief of my joy, like, you know, and that’s when you know who should be around you and who shouldn’t.

57:01 I remember telling her, I was like, honey, this is my art, and she was like, yeah, you were offending, like, Bulgarians or something. I made some joke or something about, like, where she was from, but I was like, it’s my art. So, but I guess, I guess I have to also decide, well, where’s my art and where is just me trying to be nice to people? And I guess in comedy you are gonna offend some people, right? Maybe, but you know, most of the time in comedy you’re telling jokes in a basement to other people who came to a dark basement to listen to jokes, so being offensive should really be not, they shouldn’t be offended, they willingly came to a dark, dingy basement that probably smells like beer on the floor to listen to you.

57:47 So what are they gonna be offended by? Like, and the second thing is, if you truly are offensive, you’re probably not being funny. So there’s many examples of comedians who are offensive but they’re not funny. I mean, you take, not to get too much into the weeds, we take this recent Dave Chappelle special. He did a special that was very controversial and it was called Sticks and Stones, where he deliberately was trying to be on the edge because of this so-called cancel culture, and a couple of weeks later you had the audience, critics’ ranking was zero, they really ranked his special as zero, and they would write things like, he wasn’t funny, he was boring, he was old-school.

58:22 But then the audience rating was 99. Now the audience loved it, and so when there’s that kind of disconnect, you usually know that it was the people who wanted to be offended were offended, and everyone else just wanting to have a good time, and I understood what he was doing. You legitimately realized, hey, he’s being really funny about this topic, and they went on the journey with him. And if you’re just gonna, like, call someone names, that’s not funny.

58:48 But if you’re gonna make interesting observations and be funny about it, it doesn’t matter how superficially offensive it is, you can, you should be able to make jokes about anything. Yeah, yeah, I saw the recent Bill Burr show that he did in London actually at Royal Albert Hall, and he’s really pushing the limits of offensive, but it’s like, it’s Bill, and you come there to see Bill, and when Bill does it, it’s kind of okay because you see the satire in it, but if anybody else did it then maybe they would be offended. Yeah, and if anyone else did it not in a comedy setting, it might not be, you know, appropriate.

59:18 If he said it as an anchor on CNN, it might not be funny, but you know, again, comedy, you have to take it for what it is. It’s just, it’s just, it is just telling jokes and making interesting observations, and I’m sure what you did, if you just said, Bulgarians are stupid, moving on, you know, that might not be as funny, but if you interested, if he said something like, oh, I was in Bulgaria and this happened, as opposed to this. Like, I’ll give you an example, a comedian I really like has a joke, he starts off, of course I want to, you know, men and women are equal, they should be treated equally, gender equality is very important, but you look at all, rank all the countries by how delicious their food is and compare it to the gender equality of that country, no one ever says, hey guys, let’s go out for some Canadian, that would be disgusting, but instead people go out for Middle Eastern food, you know.

1:00:15 And so he made this whole joke connecting, you know, we’re fine if a country has great food but we’re not fine with the gender equality, and we kind of ignore this weird connection between the two. But so making these interesting connections between disparate points in life is part of comedy. Was he being offensive? No, but he did point out that the Middle East is very much offensive to women in many cases, and yet the food’s the best, so is that offensive or not?

1:00:43 I don’t know, and that’s the fine line of comedy. That’s beautiful. Let’s talk about ideas, because when I think of ideas, I think of James Altucher. And when you were in my studio last time in 2015, we were walking to the hotel afterwards, and remember this, down the sidewalk, and I remember you turned to me and said, Brian, I think you should start blogging on Instagram. You said this to me and I was like, really?

1:01:04 I said, isn’t that a picture site, you know? Like, yeah, but I think that’s what you should start doing. You didn’t even say that’s what everybody should start doing, you said that’s what I should start doing, and I remember thinking too that, wow, that’s really peculiar, and lo and behold, that we saw how that just really blew up on that platform. It was very counterintuitive. And another thing, you know, you talk about 10 ideas every day, and it’s actually in my affirmations every single morning.

1:01:24 I say it on the way, when I walk to the tube, at the very end I cite myself, write down 10 ideas. And if people look at you, James Altucher, I mean, you can’t deny that you’ve had a lot of success over the last 10 years, and sure it’s gone up and down and all of that stuff, but I was coming over here today and I thought, why is James so successful? And I think it must have something to do with the fact that you embrace ideas and think of them almost as a resource, as like a commodity, whereas most people think an idea is just an idea, let’s get to the execution, right, get to the financing, let’s get to the program, but think of an idea as something that can literally change your life and take you on new courses of life.

1:02:01 And I guess I wanted to talk to you about that also. I’m in New York, for New York City for a couple of days. Why am I here? I mean, I could easily tape a couple of episodes in London, but honestly I’ve been getting the craziest ideas since I’ve been here, just meeting with someone or seeing someone or just talking to you. Now I’m getting an idea that’s gonna completely change the course of my business in my life over the next few years, I know it.

1:02:21 And so maybe we just start with that, talk about ideas. Yeah, so, so I realized this way back that, first, what everybody says, oh, ideas are a dime a dozen, execution is everything, in Silicon Valley thing, right? And they just assume that at some point they’ll be walking around and, like, lightning will strike them and they’ll think, oh my gosh, people should share cars, and all they can have in the middle to connect people with cars, and I’ll call it Uber.

1:02:48 No, I, ideas don’t really work like that, nor does execution work the way most people think. Execution, people think, oh, execution is, I’m gonna take this great idea and now I’m going to do it. The doing it can happen in a thousand different ways. People don’t realize there’s a whole spectrum of execution, ranging from really really bad, so that an idea will fail, that a good idea will fail, or really, really good. So even a bad idea might have a chance for success.

1:03:15 So, idea, having ideas is like a muscle. You just have to, if you don’t have ideas for a while, if you don’t, let’s say if you don’t, if you’re, if you’re sick and you lie in bed for two weeks, you might actually need physical therapy to walk again, your leg muscles atrophy that fast. It’s the same thing with ideas. If you don’t have ideas every day, your idea muscle is not gonna get bigger, may atrophy. And so I try to practice writing, I’ll come up with a topic and I’ll try to practice having 10 ideas a day around, like each day will be different, I’ll try to have 10 good ideas around that topic.

1:03:53 Now they won’t be good ideas, because you can’t have 3650 good ideas a year, but I tried to make sure they’re as good as they possibly could be, and I’ve been doing this ever since I wanted to network, and I’m not a very good networker, so I wanted to, I wasn’t getting interested in the finance space and I read a hundred books about investing, and I wanted to ask my heroes, you know, can I buy you a cup of coffee and pick your brain? And so I wrote to 20 people and they didn’t even say no, none of them responded, because why would they respond? Like Warren Buffett’s not gonna say, you know, hold everything, clear my schedule, Gladys, I don’t know why a secretary’s Gladys, clear my schedule, Gladys, just someone named James Altucher wants to buy me a 62nd cup of coffee and pick my brain for free.

1:04:46 He’s never gonna even respond to me, he’s gonna think I’m an idiot. So then I started writing down, I started researching everyone’s business and I started writing down ten ideas for Warren Buffett’s business, ten ideas for this person, ten ideas for this person’s business, and then I would send those ideas to the people and I would say, hey, you don’t have to respond to this, I don’t want anything, but I really admire you and your business, here’s ten things where I think your business could improve. And then I started getting responses, and actually changed my life, some of those responses.

1:05:15 And so I started doing it every single day without fail since then. I mean, I shouldn’t say every single day, some areas when I kind of dropped my discipline, I stopped doing it and I immediately felt the consequences, but now I do it every single day. And like last night, late last night, I did it, I did it, could be dumb things, it could be like last night was ten things I wish I knew as a beginning entrepreneur. The day before it was, I was making, I was thinking of a card game, as a card game called Cards Against Humanity, it is very popular, and I was thinking of a similar card game, Trump versus the World, and I start thinking of all the rules and aspects of what this card game would look like.

1:06:01 Again, it doesn’t have to be a good idea or a bad idea, but but it keeps that idea muscle in practice, and usually by number seven, it’s like a workout, like my brain is sweating, it’s, I keep counting, like, did I hit ten yet, did I hit ten yet? And then eight, nine, ten are the hardest, and it takes me, you know, 10% of the time is the first seven and the other 90% of the time is the last three. So then I know it’s a decent list. And then people forget execution is really just execution ideas, are a subset of ideas.

1:06:33 You have to be good at having ideas to have good execution ideas. So if I, I have a friend, she came up with a great idea for a business and she comes to me and she says, I need to raise a million dollars, and I’m like, well, it’s a great idea, why do you need to raise a million dollars? And she said, well, I’m gonna hire a software company, they’re gonna spend maybe eight months to a year building the software, and then I need to hire a salesperson to sell it, and I need to have a whole platform and customer service and credit card, so I need to just build this business.

1:07:03 And I said, listen, your idea is good, but it’s also such that you could do it manually, but before it’s scalable, you could do it one at a time manually to see if people will pay for and like the idea. So I said, why don’t you call five of your friends who are in the situation, that’s your market, and offer your services that you will do this, they’ll get the same result as if they had used your software a year from now, it’s just that you’re doing it manually, and now for free you can see if, a, what other nuances are involved before you totally spec out a software program that might be incorrect a year from now, and you’ll see if they like it and are willing to, what they would be willing to pay for it. And so now she’s testing out her idea for free before she goes through the process of raising a million, building a product and so on.

1:07:52 That’s what I mean, like now she has good execution, before she had bad execution. She might decide after the good execution this is a bad idea and then she can move on, or she might decide, okay, now I thought, learned some new things, now I can better define the software product, I could see these are the things that are important, so maybe it’ll be cheaper for me to design the software product, I know the sales process because I’ve done it before, or five times. So that’s the difference, very simple example, difference between good execution and bad, and it’s just a matter of, you have to have the right execution ideas to have good execution.

1:08:24 So when I have an idea that I think I might turn into a business, I try, I come up with a list the next day, what are the simplest execution ideas? So can I tell you one idea I had that I thought was a decent business? So I’m asking for your information. Yes, please. So this was a few years ago, although I could describe an example from the other day, but this one I always use as an example.

1:08:46 I was at a lunch and this friend of mine brought his girlfriend and they were all kind of cuddly with each other, and I’m like, oh, you guys seem happy, and they said, well, we just had the discussion, we decided we’re gonna go steady. And I’m like, how old are you? You’re like 46 years old, like this, I thought that was a high school term. And they were giggling and they thought it was funny. So then I thought, what does it mean for people their age to be going steady?

1:09:16 So I thought of an idea, I wrote down ideas and I thought of one idea, which was a Going Steady app. So what it does is you download this app, you connect to the other person that you’re going steady with, now the Going Steady app deletes all the dating apps on both phones and alerts you if anyone downloads, you know, either disconnects or downloads a dating app or whatever, you know, however you define dating, it alerts you if dating, see, or intrigue seems to be happening from the other person. So that’s the Going Steady app, and I told it to a bunch of people, everyone said, oh my god, I would definitely use that, we definitely use that, it’s a fun idea.

1:09:51 And there’d be other features in the Going Steady app, like if they want to, they could turn on a, you know, where is she, where is he, and getting closer and whatever. And so then my, the next day I spec’d out every screen of the app and then I put the spec on I think Upwork.com, which is a freelancing website, and 20 freelancers responded and they all said they could do it, and then I had just one question: can an app see other apps on the phone? And 19 of the 20 people said, don’t worry, don’t worry, don’t worry, they can.

1:10:28 One person said, yes for Android, no for iPhone. So okay, now it’s about, it just went from being a good idea to a bad idea, I can’t make this app for the iPhone, and that was the end of that. But if I’d gone through the process of trying to make this and whatever, it would have been hours and hours of heartache, thousands of dollars and just wasted. Instead I had a fun idea and practiced my execution idea muscle as well, and within an hour decided it was a, it was not a good idea after all.

1:11:00 And then, well done, all right, so that saved you a lot of time. Yeah, and got you some interesting information for maybe your next idea. Yeah, exactly. Do you store these ideas then somewhere or there else? Okay, and that is that part of the point as well, part of the point is just get them on paper, just to exercise the idea muscle.

1:11:15 It’s like when you work out at the gym, do you watch videos over and over again of your last workout? Probably not, it’s just, you’re building your muscles. So I always throw out the ideas, but if an idea is still in my brain then the next day it’s like, this one, next I had execution ideas about the older idea. So or if I have a book idea, it’ll somehow stick with me and then maybe I’ll write the table of contents, something like that. Okay, and use those pads you got in front of you, which are ladders pads?

1:11:44 Yeah, waiter’s pad, that’s specifically, I get one of those before I leave. Yeah, absolutely, do we have extra pads? Yeah, yeah. And what about this concept of idea sex? What does that mean?

1:11:55 And because that’s almost like the next level, or the black belt level of ten ideas a day. Yeah, so let’s say, I’ll take just a simple example, let’s say you’re having a hard time getting a babysitter, so you know, this is a problem, I wish there was an easier way for me to get a babysitter. Meanwhile, Uber is a successful app for finding transportation when it’s hard to find transportation. So what if I combine those two ideas, Uber with babysitter? Now I’m gonna make the Uber of babysitters.

1:12:27 So I have several teenage daughters who love being babysitters but they don’t necessarily have a good network. What if there are people in the area who have an emergency need for a babysitter, now the Uber of babysitters can help it out. So that’s a simple example of idea sex. A more complicated example might be, you know, George Lucas with Star Wars completely took ideas from the common themes of a Western and combining it with science fiction and created Star Wars.

1:12:58 And so that’s a little bit more complicated, or the rap group The Fugees took a rap beat and applied it to the hit, you know, 70s disco song, Saturday Night Fever, and created the rap song “Stayin’ Alive.” So there’s lots of different types of you know, ideas, sex, ideas that are out there, because usually everyone’s already mastered this, the people are already, you know, experts in physics and there’s other people are already experts in biology, but now there’s a whole new field, biophysics, which, you know, combines the two fields, and now it’s a new field of study that you could become an expert in. So the more things that are interesting that you combine, the greater chance you could be the best in the world at this intersection.

1:13:46 So if you’re really good at science and you love sports, at the intersection of science and sports it’s probably a whole, is probably thousands of potential articles and books that haven’t yet been written that you can now write because you might be the best in that intersection. It’s also a good way to kind of own that number one spot, yeah, as a completely, fight for the top five, right? So, so again we see this with a lot of different types of sports, but yeah, so again, like with the Fugees song, The Fugees may or may not, or you know, a great example, Scott Adams talks about this.

1:14:21 Scott Adams is the creator of Dilbert, which is maybe one of the most syndicated cartoon strips ever, and he said, well, he was pretty good at drawing but not the best, he was pretty good at business but not the best, he was pretty good at humor but not the best, but at the intersection of those three things he became the best cartoonist in the world, he’s the most successful cartoonist in the world right now. So that’s a classic example of where it works. Yeah, she’s also thinking about, you know, David Goggins had his new book called Can’t Hurt Me, and it’s a mix of an audiobook and a podcast, so he’ll read a chapter or his writer will read the chapter and then they do like a mini six-minute podcast after each chapter.

1:15:03 So you know, I’m sure he was listening to you when they got that idea. That could be, I mean, he’s been on a lot of podcasts, great. Was he on your show? Yeah, it’s a great guy, he’s intense, man. We have a pull-up bar in our studio and he was showing me his technique that he did for 4000 pull-ups and 1700.

1:15:18 Oh my gosh. Yeah, we have Wyclef Jean as well on the show, I had to go to Paris to interview him, but he was telling me about how they made that Fugees song, the “Ooh La La” song, and I had like chills running up my spine. Yeah, they used to be in a basement in Jersey, I think, with the samples, and man, crazy stories. And even the business models as they developed in hip-hop, they kind of took elements of, you know, hip-hop culture with business culture and combined them to create new business models.

1:15:46 So there’s lots of examples of great idea sex, and then just thinking of it in one’s own life, you know, just, there’s so many ways. Like I’ve done an exercise with people where I say, okay, make your list of ten ideas, and it’s everybody in a room, and then look to the person next to you and now come up with a few ideas that are ideas from your list having sex with ideas from the other person’s list, and it’s just fascinating, you know, what comes up. So is that, if you had to chart it down to one reason you’ve been so successful, and I know you’d be like, well, Brian, I have been successful, well, let’s just assume you are successful, would it be the ideas?

1:16:27 Absolutely, because I mean, everything, everything I’ve ever invested in, everything I’ve ever been an entrepreneur about has been, you know, kind of, you know, using some ass, like I, for instance, in the, oh, as I started this company called StockPickr, which was like a social media site for finance. So there were a lot of finance news sites, but I really hate looking at news. I think all news is sort of, you know, people looking in hindsight and trying to fit their own opinions into something that already happened.

1:17:00 You told me you worked in a newsroom one time and you said, oh yeah, I remember this distinctly, in the last show you said, Brian, it was like Halloween every day, we had to scare people. Yeah, exactly. So I don’t trust any news at all, so I wanted to create a useful finance site that would help people but would have zero news in it, and at the same time social media was just starting to really explode, and so I wanted to create, I wanted to combine ideas from social media with finance, which hadn’t been done before, and I did, and the result got, within the first month we were starting to get a million users a month, and then it was easy to sell the company.

1:17:36 So almost everything I’ve done has been some combination of ideas, that’s because it’s hard to, it’s hard to develop something new that the world has not seen. The only way to do that, I now really feel, is to take a couple of old ideas that have proven themselves out and combine them. And I, when I think about every single company I’ve invested in, they all do that to some extent, and it’s a common, it’s a common thing you see actually outside of the US.

1:18:02 Oh, Google worked, so in Russia let’s make Mail.ru, which is like the Google of Russia. Oh, Amazon worked, so let’s, in China, make Alibaba, which is like the Amazon of China. So there’s all these people even described movies, you know, that way. It’s gonna be like, you know, Star Wars plus, you know, Butch Cassidy and the Sundance Kid, and we’ll make a new movie. And so, so you know, idea sex is great for selling things, it’s great for coming up with new ideas.

1:18:31 You know, let’s say you love the game Monopoly but you also love teaching, CEO, as being a CEO coach, you can certainly write a blog post or a podcast or write a book, you know, how Monopoly made me a better leader, you could do a TED talk. Like just any two things can be combined in some weird way. I’m not saying that’s a good idea, that’s part of the joy of it, is just come up with tons of bad ideas, but you also pull the trigger and execute. You’re not the guy that sits in the corner with a pad of ideas and then you go daydream.

1:19:01 Like, you pull the trigger more than most people I know. I mean, you made your 15 million, you immediately start investing in companies, you buy a comedy club, you know, you build the websites, I mean, that’s another thing that I think is unique to you. Yeah, so doesn’t that scare you though, when you’re cutting big checks, investing in companies? Well, it obviously doesn’t scare that much because you do it. No, but I am very risk-averse, which is, I think the best entrepreneurs are risk-averse.

1:19:26 Like you mentioned how you were scared when you made the leap to hiring a person, you didn’t hire 20 people, you hired one person, so it was a it was a manageable risk for you, you did what was scary but it was still a manageable risk. So I think when I first, the first three times probably I went broke, my checks that I was writing for investing, hey, I wasn’t doing the correct due diligence on the companies I was investing in, and the checks were too big. I realized the smaller I invest in a company, the more money I will make, which is a weird irony, because as long as I can sleep at night not thinking too much about this investment, I can let it grow and grow and grow and grow, but if I invest a big check I’m thinking about it constantly, and as soon as I have an opportunity to take it off the table I take it off.

1:20:12 So I actually make less money when I invest more. And so but it’s also being risk-averse to write a smaller check. So the way I execute is, again, I’ll write down that list of ten ideas, then if one idea is just sticking in my head or if there’s something I’m fascinated by, I’ll write down a list of execution ideas the next day. One or two might be doable, like, oh, let’s spec out screen by screen and put it on a freelancing site and see what happens, or let’s talk to these five people and see if they would use this service.

1:20:47 And so I think of very simple ways to execute, and if I get the green light on these simple ways, then I might make it next list, okay, what’s the next step on executing? Maybe I need to meet somebody in the industry that could partner with me, and so I’ll see, here’s ten people I should meet with, and so they want to be partners and so on. So I usually am very careful how I execute it’s. I write down execution ideas using the idea muscle and I just, it’s always very simple, I should be able to test an idea very quickly, you know.

1:21:20 So it’s the execution ideas that allow you to execute so intelligently and quickly. Like a few weeks ago Trump had this insane tweet, and I’m not, I’m not making a judgment on it, it was just this weirdest, it was just a weird tweet where he said he wanted to buy the country of Greenland. Okay, and I’m thinking, what, it sounds weird but interesting, so I started doing research on it and I saw maybe some reasons why someone would want to do it. I realized also China was secretly buying, or not so secretly, they’re kind of quietly buying all the natural resources in Greenland, and what those resources were and what the laws were around Denmark and Greenland, and so I came up with an idea, I put up on GoFundMe and Kickstarter a crowdfunding campaign so I could buy Greenland.

1:22:10 And so a, it’s a fun idea just to get attention, but b, instead of writing an article, here’s why it might be interesting to buy Greenland, I’m able to express it in this unique way, a crowdfunding campaign, and who knows where that goes, but it’s at the very least a way for me to express all the reasons why I think Greenland’s interesting. And then after a few days GoFundMe shut it down because they realized this probably wasn’t serious and they were racking up transaction fees. People were donating to this GoFundMe and they were, they have to eat the transaction fees even if all the money is returned, so they shut it down.

1:22:45 So okay, experiment done, didn’t work, would have gotten to something interesting but it didn’t. And most likely, you know, Thomas Edison took 10,000 experiments before he made, created, invented the light bulb. You take a lot of, if you take a lot of simple experiments you never know what’s gonna happen, but it allows you to execute in a risk-free way many ideas. What do you think the price of Greenland is? There’s a price.

1:23:10 Yeah, I was thinking to myself 21 billion dollars. 21? I was just thinking, okay, it’s gotta be more, right? So, so Greenland, Greenland spends 700 million a year in subsidies to finance Greenland, so, so I mean Denmark spends 700 million a year to finance Greenland. So I just figured a normal multiple on a company might be 20 or 30 times to kind of figure out what would incentivize Greenland, I mean Denmark, to not have that burden.

1:23:39 So that’s why I came up with 21 billion, but my other research sort of figured, oh, there’s much more than 21 billion dollars’ worth of natural resources underneath the ice in Greenland, and there’s a lot of other benefits. So in plus there’s some value to not having China own all of those resources, and and it’s value to not having the US own all of those resources. So I figured that’s why I put myself in the middle, and the 21 billion was just a guess, though it was like a reasonable guess.

1:24:11 It’s not such a crazy idea. If you remember in the, in the Greek crisis, Greece was talking about selling off some of their islands to, like, make, you know, make the budget, so maybe there will be a lull in the economy where the US could scoop up. Yeah, and Denmark said, oh, it’s not, Denmark immediately said after Trump’s tweet, oh, it’s not for sale, come on. If someone, you know, Denmark’s national debt is about, I think, a hundred billion, what if you just simply offered to pay all their debt, so at least a hundred billion would easily get you agreement.

1:24:40 So that’s why I figured 21 billion, you’re probably, here, you’re handling their interest payments plus their subsidies to Greenland, they don’t care about the resources. So I figured, you know, 100 billion definitely would be the price, 21 billion is a decent discount to that, but it forced me, by the way, the benefit of that experiment failing, no experiment is actually a failure, because think of what these experiments, I even these little experiments I said, I’m always involved in, like, let’s say 15 different experiments at any one time, even these experiments I mentioned to you, I learned all about Greenland, I learned about the natural resources and the value of them that they have, I learned what the geopolitical situation is that would cause Trump to make such a tweet, I never ran a crowdfunding campaign before so I learned about Kickstarter, GoFundMe and a couple of other platforms.

1:25:29 So I learned something. In the other one, the Going Steady app, I learned the difference between Apple and Android and actually its implications on privacy. Android, you ought to be careful, an app could see all your other apps, I didn’t know that before. So every experiment you learn something, it’s powerful stuff. James, let’s talk about college really quick because we both have daughters, mine’s 15 and she’s thinking about college.

1:25:51 I know your daughter’s thinking about college as well. You went to Cornell, I went to MIT, we had our experience. Oh, brag a little bit more. Technological, I would say that I went to Ithaca actually, in toward Cornell right before I went and you were like, oh, I’m gonna actually, instead, it was just too quiet up there. Yeah, well, if you come from San Diego where it’s pretty quiet, Boston was like this magical place, and they remember there was a guy that was crooning in the subway, he had like a, I don’t know, like a box there, and I was like, I gotta go to school here.

1:26:20 So, um, but tell me about college, why do you not think kids should go to college? Well, you went to MIT, right? And what did you study? Mechanical engineering and then finance. I see.

1:26:33 Um, I see you’re heavily doing mechanical engineering right now, but that’s not what I learned, though. I learned mechanical engineering but I learned so much more, Jane. Well, you learn, I learned how to get my life together and how to get things done. For me MIT was a game. That’s fair, ’cause I joined a fraternity house when I was 18 years old, there was 50 guys in a house, average age 20, max age 22.

1:26:54 I moved in literally five days after I got there, so I’m 18 in this house where there’s beer and there’s pool tables and there’s girls and there’s parties, and literally I saw guys that got into MIT that went back home and became bike messengers six months later because they couldn’t have the discipline to get through school. And so I learned about discipline, I learned about all sorts of ways to push myself, I can compete with the best. I also had a complete social situation, I mean I got a lot out of it, right?

1:27:22 That all sounds great. So what would you, what should an 18-year-old pay to be around a lot of beer and a lot of girls and a lot of friends exactly their same age and mostly demographic way, and this is what, how much did they pay, what’s the price of that, what should be the price tag on that? Well, it’s more than just that though, too, right? Well, well, so it’s, well, it’s also learning, being part of an institution, but you learn anyway, you could learn just by reading books, but what I, having a podcast, but what I, maybe, maybe, maybe, but what if I just got a job and lived at home or got an apartment?

1:27:57 I don’t know, for me there was a gestation period that I just feel like was really important for me. Now could have been a camp as opposed to university, and might be, it doesn’t warrant, what does it cost these days? I wasn’t here. MIT is about 67,000 a year, it’s like total. Yeah, or is that just tuition?

1:28:11 Oh, I paid fourteen five. Yeah, dates me, right? So, so when we went to college I think it was on the borderline of being more thin and not worth it, and it wasn’t even a discussion. Like, if you want, like there were very much fewer side hustle type of jobs, like, you know, you’re doing a podcast, you made, you basically created your own media empire, one-man media empire, which such a thing was not even possible back then. You kind of had to get a standard job, and since the employers at standard jobs had college degrees, they would only hire people like them who had college degrees.

1:28:46 So there was a price tag then for getting a standard job where you could then make more money, and you want to get into as much debt. So when I graduated college I had, I think, $47,000 in debt, and maybe a little bit more, maybe like $60,000 in debt, and you know, over time I paid for it. Now kids, I was talking to somebody the other day, he’s going into his junior year and he has $150,000 in college debt, and I’m like, what are you studying? And he said business, and I said, okay, you should switch majors, business 101, don’t go $150,000 in debt until you have a business.

1:29:24 Like, what, they’re lending money out like it’s nothing, because, are not, our, the student debt is the one type of debt in the U.S. you cannot get rid of in a bankruptcy. It will ruin your life, the government will ruin your life if you try to stop paying your student loans. Second, the price of college has gone up 10 times faster than inflation over the past 40 years. I mean, the only other thing we can compare to is health care costs have gone up three times more than inflation in the past 40 years.

1:29:55 Now with inflation up so much faster than incomes, it doesn’t make the same economic sense. So you have to point to things like, it taught me discipline, it teaches learning, it teaches social activities, because you can’t just make the income comparison, and any study that does it is using kind of old data, data from the past 40 years, but data right now, it doesn’t make economic sense to spend you know 20 or 50 thousand dollars on an education at 6% interest, for most people are going into debt, 6% interest, you’re never gonna beat, you’re gonna pay it back by the time you’re 60 years old, whereas there’s so many online ways to learn. Yes, you learn discipline, but you mentioned other people at MIT didn’t learn discipline, so it wasn’t, it was you who brought the discipline to it, wasn’t MIT.

1:30:42 MIT, it was some people had this, is when some people didn’t. So you know, there’s online ways to learn, there’s apprenticeship ways to learn, there’s things you learn on the job. Like I was a computer science major, my first job I was so bad at computer programming after majoring in computer science and going to graduate school for computer science, I was so bad they had to send me to a remedial computer programming school to be good enough to be the lowest level at my job.

1:31:09 And so the real world skills don’t translate right now. The other thing that’s a real problem is more macro rather than micro, which is that you have one class of kids getting a quarter of a million dollars or even $100,000 in debt and another class of kids, the kids of wealthy people, who aren’t getting into any debt at all. They’re marrying each other and having future kids who won’t get into debt, very, marrying each other, and this kid not only has the debt of the parents to deal with, but then this kid’s gonna get into debt when he or she goes to college.

1:31:44 So that actually is what increases income inequality, as opposed to, oh, I’m gonna pay this person this song, if is the societally, college is so distorted and its incentives that that’s increasing income inequality. So right now I have four daughters and a son, and two of them are applying to college, despite they know what, how I feel about it, but I don’t, I don’t argue with them. And you can afford it. So that’s, I can’t afford it, but you still think it’s not a good use of their four years?

1:32:12 Or no, are you gonna make them pay for it? No, no, I will pay for it because society is giving them an advantage because of me, so I don’t want them to be at a disadvantage. I don’t think it’s a, I think there are disadvantages that are fair, I think this is an unfair disadvantage, the fact that college presidents are making millions of dollars because the government is forcing, because got the government, you can have any tuition, the government will lend kids the money for it.

1:32:41 So there’s no Harvard or MIT could probably charge three hundred thousand a year and they’re still gonna be an audience. We see some of these parents in Los Angeles are paying like cut in half a million dollar checks to get people into USC. So obviously I think the actual value of the education is even higher than these inflated rights. Well, the value of the people, I think the bragging rights to them are worth more than a half a million value. In one of the actresses’ cases the kid didn’t even want to go to college, so she kept saying, I don’t want to go to college.

1:33:10 Well, I get a lot of emails from people who lose me, but my oldest, he’ll write, exactly, and now quite a few other people, but my oldest daughter, she had finished her second year and she knew how I felt, but I gave up arguing with her a long time ago ’cause I knew that wasn’t gonna be the way to win. I just wanted to, you know, every now and then drop hints and live by example. So my oldest daughter finished her sophomore year and she dropped out, and because, and now she’s actually, instead of waiting two more years to do what she loves, she’s starting to get her foot in the door at actually doing what she loves.

1:33:46 And I think, I think she realized that the real world offers so many more opportunities, again different from when we went to college, but the real world now is filled with people like her who are taking an alternative path, and she’s learning so much more actually doing really what she wants to do as opposed to learning what she wants to do. So you can learn classroom skills in the classroom, but you only learn, you only learn the skills of what you love doing, what you love. So I only learned how to really program when I had a real job doing it, instead of all the homework assignments that I had where I was programming.

1:34:20 All right, you’ve started convincing me a little bit, James. I guess I remember this idealized version of my college education, it was also a big learning experience and growing experience for me personally, and also for me, having that, you know, that degree from that school helped you a lot going forward. Uh, I don’t know because I don’t know what job I got on the basis of, and that’s particularly to me. So that’s work now, it’s anecdotally. I do think it does, like MIT, you’re applying, if you apply for a banker job or an engineering job or a hedge fund job, the MIT degree helps.

1:34:53 I don’t think I, I think there was another thing going on with me, that where my degree from Cornell did not help me at all, but it was maybe it’s just anecdotal. So I agree, probably back then it probably helps. Right now I don’t think it necessarily helps. Like I don’t know where anybody working for me went to college. Jay, where did you go to college?

1:35:14 What is that, where’s that? Oh, Florida in the States. I never even heard of this college before. What’s, what college was it? Yeah, so I didn’t even know he went to college until just now, and all of you, oh, and asks, do you offer to cut your daughters and son the check if they don’t want to go?

1:35:33 I do. They never have taken me up on that, and even my daughter who dropped out has not taken me up on it. Like, that’s an unfair advantage that she doesn’t want to have. Fair enough, got to respect that. Yeah, that’s probably what you might have done.

1:35:44 Is I told her at least be an intern here at a comedy club, you could be getting, making a little extra money at night and meet all these comedians and actors and actresses and so on. She doesn’t want to take any advantages from me, even though I pay for the first two years of her college. Welcome to teenage girls. Yes, it may be boys, to tell me about the world, the word no. You earlier talked about how you might want to buy Warren Buffett coffee and he would say no, and I’m sure people ask you, James, I’d love to come pick your brain and buy your coffee, and you say no, but you always didn’t say no.

1:36:15 Yeah, tell me about this concept of the power of no. I think I, I think it took me a really long time to learn how to say no for various reasons. One is, you know, you know how you mentioned, oh, you at some point you said yes to coming to New York City and now maybe you’re glad you did because you learn all these things, you’ve had all these extra podcasts, you’ve had these experiences that it made you think about things, so there’s a power to yes also, even to saying yes to things you’re, you mildly don’t want to do or things you’re afraid of or whatever.

1:36:43 So I was always thinking I have to say yes to every meeting, every opportunity, because who knows what I’m missing out on, it’s that fear of missing out, and also I don’t want to offend people and I’m flattered people asked me to do something, so I’ll say yes. Oh, do you want to go on this TV show in LA tomorrow? Yes, and then I have to fly out to LA to do one TV show for five minutes and then fly back. So I started kind of practicing saying, you know, in uncomfortable situations, two things I normally would say yes at 2:00, and I realized I was getting so much more productive in my life.

1:37:21 I actually had time to write every day, I had time to do a podcast, had time to explore business ideas or explore potential investments, so I started saying no to just everything I didn’t want to do. Now that could be overboard, to maybe, like if I had been you, I might have said no to coming to New York City, because that seems like, oh, I can get 27 more things done if I say no to this. So sometimes I maybe overdo it, but saying no is so valuable for carving out, again, freedom in your life.

1:37:54 Like, what are the things that affect freedom? It’s, but a, what we’ve talked about before, vulnerabilities is trading privacy for freedom. Another thing is saying no to things you don’t want to do. He’s basically saying no to other people’s agendas, so I just want to do my agenda, not someone else’s agenda that I strongly feel is, doesn’t 100% align with mine, and so that is a way I carve out, every time you say no you carve out more freedom. Now then there’s a balance, there’s a gray area where you should, you have to evaluate, yes might be good, but most of the times where you think, you’re, so this doesn’t feel good but I probably should say yes, I mean that’s probably should be a no.

1:38:32 So it’s, it’s, it’s a power and it’s freedom. Now people will hate you for it, people will stop asking you to things, but you know, there’s a give-and-take. Are you getting better at it? Ah, sometimes. So it’s still really hard, you know, you only write books about things you’re bad at.

1:38:51 So like I would never buy a book about dating from Brad Pitt, right? So I would buy a book about, ’cause Brad Pitt has different problems in his dating than I do, and I would want to buy a book by someone who has problems with dating, who overcame it and became more social and, you know, learned, you know, I don’t know how to be a better dater or whatever. Same thing for me, I didn’t know how to say no, so it was the exploration of learning to say no, situations to do it in, you know, when do you say no to family, when do you say no to your kids?

1:39:27 You know, there’s different reasons you say no to family because family always, a, you know, if your extended family asks you to Thanksgiving and they automatically assume you’re going, maybe you want to be by yourself for Thanksgiving, so that’s a different type of no. Then you say no to your kids running out of the house without washing their dishes, because we’re trying to set up boundaries for them. So there’s different types of nos. You say no to your boss, not because you want to get fired, and you can’t be afraid of being fired, you have to just say no to, oh, there’s a better way to do something, and then you have to learn what’s the way to say no that’s not going to insult him, you know, ’cause I’m very sensitive to, I don’t want to insult anybody.

1:40:05 So you know, in exploring my own nos, oh, that’s how I was able to write what became a best-selling book, The Power of No. Right, and Choose Yourself as well, Choose Yourself too. Yeah, I was always, there’s a bit of the power of no in there as well. Yeah, because again, if you’re not, it’s guaranteed, if you’re not choosing what you want to do and who you want to be in life, someone else is gonna do the choosing for you and the results won’t be as good. So like, for instance, if you wanted to publish a book and you said, I’m not gonna publish a book unless a publisher accepts me, well, now you’re letting these four or five gatekeepers have this incredible ability to block your career, like just four or five people.

1:40:51 They might have it, wake up, have a bad day, they might not like you for some reason, they might watch London Real and I don’t like this show, I’m not gonna accept his book, and you’ve totally denied yourself the chance to publish a book when you could just write a book and publish it on Amazon. No one will ever ask you again who was your publisher, fewer people will ask you who is your publisher than will ask you what college you went to, and but now you have a book out there that could be a best-seller that could inspire tons of people. Many best-selling books started off as self-published books, you know, including self-help books like The Power of Now, including, I know, Fifty Shades of Grey started off as a self-published book.

1:41:30 So you know, what we live in, in this world where there’s, you maybe someone would have said to you, you could have pitched, Brian, you could have pitched London Real to 50 TV stations and 100 radio stations and they all would have said, ah, I don’t think so, but instead you just did it yourself, you chose yourself. I’m gonna make a show, and you did it, and now it’s a real show, it’s bigger than most TV shows. So you chose yourself. Yes, stop waiting for permission.

1:41:58 Yeah, stop waiting for permission. Or if someone says you can’t do something, those are the people who can’t do it, you have to still do it, but you just have to figure it out, your execution ideas have to be good. What are your writing goals right now? Do you have more books planned? How often do you blog right now?

1:42:13 And then like, you know, Choose Yourself, I mean, how many copies has that sold now? Choose Yourself sold probably a little bit under a million now in like 20 different countries, and you know, my first, and that was like your 18th book you published, I think that was, I think that was my twenty-done quite a since then. Okay, and my first five or six were regularly published books by publishers, Choose Yourself was self-published and probably is still one of at least top 100 of the best self-published non-fiction books in terms of sales, but my, you know, I want to go, I’ve since we’re in children’s books, ever written all sorts of books, but I really would like two things.

1:42:55 One is I am writing a book with a mainstream publisher, HarperCollins, coming out in Q1 2021, where I want it to be about this aspect of not just choosing yourself but how you can quickly get to the top of whatever category it is you love. So most people take this standard route and they think it’s gonna take them, they have to put in 10,000 hours, it’s gonna take them 20 years, but as you know, because you’ve turned this from an interview between two people with no audience to a huge show, there’s ways to skip the line in whatever you want to do. You weren’t, you were never a professional show producer before or professional interviewer, but suddenly, suddenly you’ve become in the top 1% or 1/10 of 1% of all shows out there, podcast, TV, radio, throw them all in, you’re in the top 1%.

1:43:44 And there’s ways and techniques to skip the line, but most people either don’t know them or they’re afraid to do them or their friends and other gatekeepers are preventing them from doing them, they don’t realize there’s ways around those gatekeepers. So I’m really going to be very specific about how you can try anything, skip the line, and be in the top 1% of what you love doing and have all the recognition and income and whatever that, you know, such a position accords. So that’s one book that I’m doing, but I also want to write a roller novel, so that’s done, fiction before.

1:44:18 I’ve done fiction before, I’ve done fiction before, but I’ve never, never published fiction before. Okay, is that you two enjoying tonight? It’s a quick read, it’s a good ringtone. And so HarperCollins 2021, yeah. There are other, and how often are you blogging these days?

1:44:43 I tried to blog every day, or I try to at least write a post every day. How many words? It depends, usually anywhere from like 800 words to 4,000 words. It’s a lot. So yeah, like last night I wrote probably 3,000 words and I haven’t decided whether to publish it or not.

1:45:00 It was, so I made my list of 10 things I wish I knew, 10 critical things I wish I knew as a beginning entrepreneur, and then I wrote a blog post around it which I haven’t published yet. How long does it take you to write something like that? Um, the hard part is sitting there for hours thinking of what to write about, but then the actual writing maybe an hour. And you, okay, bang it out. Yeah, that is just jello.

1:45:25 Do you have to proof it or rewrite it? Or yeah, yeah, we write like 10 times. Really? Yeah, yeah, 3, write everything, then how do you want a day? That’s like three hours.

1:45:32 Alrighty. And every day, every day, rewriting is critical, because when you write something, when you’re writing the first time, you’re just like vomiting out all of your ideas, and then it’s only in the rewriting that you start to craft it into something that other people are gonna want to read. Nobody wants to read vomit, but they want to read, you know, you know, carefully you know, cooked cuisine. So that’s the difference between writing and heavy rewriting.

1:45:56 Okay, like I bet you the next time you write something, I’ll give you a little trick. The next time you write something, write the whole thing, do whatever you’re gonna do, write it out, and then first thing you should do, delete the first paragraph and the last paragraph, and I bet you your article will be, will read better, will be more interesting, and even knowing this rule, and even while you’re writing you’re thinking, James is gonna say take out the first paragraph, for this first paragraph it’s great and this last paragraph it’s great, but now just immediately take out the first and the last, and I will still read better, be tighter, it’ll engage people more. Yeah, and you’ll start with a cliffhanger, and that’s what you always do with your writing, right?

1:46:34 Yeah, here I always start, you’re in a gutter, you’re broke, you got divorced, like there’s always something that starts me with it all de jure. Yeah, whereas where’s my original first thing that I might write, my, the worst thing that ever happened to me was in 2016 and I was, you know, having problems in this way, this way, no, just the next paragraph might be, then I was in the gutter. That’s such a great first line. So it is 2025, what does your life look like, what are you doing, what’s your day, what’s your daily routine in 2025, January 15th?

1:47:09 I hope it’s similar to now, or just all day long I’m only doing things I want to do, so I don’t know what those things will be at all, but I hope never at a point where more than 10% of the things I do in a day are things I don’t want to do. So I’m a, I, it’s a very important rule for me, never take time from the things you love to do more of the things you hate. So so often you see a banker, for instance, or a lawyer, accountant, I’m not making fun of these professions, but they start getting busier and busier, so where can they take time from to put more time into work?

1:47:43 Well, they take time from family, they take time from friends, they take time from creativity, so they can get to that, you know, managing partner position, and then they think, when I’m a managing partner I’m going to stop, but your bosses know you’re gonna think that, so they structure the incentive so you don’t say that. And just in every area of life I think the tendency is to do more, to take things from what you love to do more of what you hate, and I like to do the reverse of that, or at least check myself to make sure I’m doing the reverse of that. So ninety-ten is what you try for?

1:48:12 Yeah. All right, but that might look like more books from HarperCollins, more businesses you’re involved in? Actually a lot less businesses to be involved in, I don’t really enjoy business, really. You, you make money doing business but I don’t really enjoy that. How many businesses are you involved in, in terms of, let’s say, between heavy involvement to talking to the CEO maybe once or twice a week?

1:48:36 Probably about 10, and then maybe another 10 to 15 where I’m just passively involved. Okay, and your own business is quite big? Yeah, and that’s your blog and your mailing list and all of your products and all of your books? Yeah. So what, in 2018 that was about 60 million in revenues, but even there I have a CEO, I have employees that don’t live in New York City, so I’m not, I don’t have to be as involved as it would seem.

1:49:01 Okay, 60 million’s a massive figure. Yeah, it was good, we toy, and we had no investment when we started off with what we had, strong partners who were able to contribute resources, valuable resources. And what does that business look like, is it book sales, course sales, like what is there, like course sales, like, or newsletter sales, like, oh, or wellness, like? Yeah, like I have a newsletter that’s more about, you know, here’s another side hustle you could do, and we interview people and, but who made a lot of money from that side, we do step by step, here’s how you could do it.

1:49:33 Like for instance, let’s say someone made a million dollars doing a podcast, we’ll do step by step how to start a podcast, step by step how to publish a book. Another newsletter might be, oh, you’re interested in marijuana stocks? Okay, marijuana is a fast-growing industry, some of these companies are scams, some of them are good, we will do the research to tell you which ones we think are good and which ones are scams and so on. And so when we put those out, you still like watching the stock market and being nimble?

1:50:02 No, I hate, I hate that. So I do, you ever loved it? I did it a lot, all day long, 23 hours a day, I ran a hedge fund, but I always hated it. So because also if a company is good then you shouldn’t have to look at the stock every day. Like I’ve invested in one company, it’s a great company, I make it a point to never look at the daily.

1:50:23 You don’t know why a stock goes up or down, somebody might be going through a divorce so they have to sell a chunk of shares at 3:59 in the day and the stock goes down and you think, why did it go down, was there bad news? No, there’s no news. I know the companies that I’m invested in, and everything’s, as long as the story stays the same, I don’t have to do anything. Yeah, daily habit for you that’s non-negotiable, besides the 10 ideas, besides the writing, but just something you have to do every day, maybe something more from a personal, you know, or physical or mental well-being point of view, what’s something you have to do?

1:50:57 I mean, they’re, you eliminated the most of all right, none of those important things but the read, writing, and I’ll say reading is paired with writing, so I always have to read to write, and writing the 10 ideas is non-negotiable, but meditation, physical exercise, anything? I think, I think exercise is starting to be, it wasn’t always but I’m getting older, so you have to exercise to maintain health, but I think my relationships with my wife and my kids and my friends, I think I have to, I have, I have what I call a daily practice, so every day I have to ask at the end of the day, did I 1% improve in the areas of physical health, so that include, that might be exercise, that might be quality sleep, it might be quality eating, emotional health, did I do something to improve my close relationships or get rid of relationships that are not so close, creative health, so that’s, you know, writing these ideas down and so on, or doing something else creative like a podcast, or what I’ll call spiritual health, which is getting more and more of a sense of things I have not obsessing over things I have no control over.

1:52:06 So if someone yells at you on Twitter, I can’t, someone yells at me over Twitter, even if it’s someone I’m like, why are you yelling, I can’t control their behavior, so I have to not think about it. So those are that little, all those things are non-negotiable, they’re all connected. Okay, you can’t, if you’re obsessing on someone angry at you, you can’t write ten ideas, you can’t be, you know, great with your family, you can’t, and if you’re obsessing, all these, you’re not gonna be as motivated to exercise or eat well and you probably won’t sleep well, so there are all these things are connected.

1:52:39 Agreed on that. If I would ask five of your friends what is James’s superpower, like what is the thing that he does that allows him to do all of this stuff, what would they say, assuming you are a superhero? I don’t know if they would think of me that way, but I think they would think I’m productive, and it’s in part because I say no to lots of things. I think they would think I’m very probably quirky, but I don’t know what else, I don’t know what else. What else, Steve, would you say the audience, you can’t hold audience?

1:53:12 I don’t know, I don’t know, I honestly don’t know what they would say. Some of them don’t like me, but then they don’t stay friends for long. I think probably quirky and productive and kind of, I don’t think contrarian, but I, I don’t think they would say contrarian, but I think they would say you won’t, you don’t know what he’s gonna say, so he’s a little unpredictable. Yeah, curious. Yeah, okay, I got, I got from the audience, it’s good.

1:53:38 What was the best day of your life and the worst day of your life? I have no, I have no idea, so I just kind of live each day, each day as it comes, unfortunately not on what I’ve not, I’ve never, I’ve had really bad things happen, but in hindsight, I mean, have perspective and, you know, look at the good and the bad in them, and I’m sure the same thing is true about the good days, they were both good and bad things about it. For instance, the first time I made a lot of money, that would at first, that seemed like the best, one of the best days of my life, but it turned out I wish I have more regrets about a day like that than regrets about the worst day of my life.

1:54:21 So it was hard to say. You have more regrets about the day you made the money? Yeah, because I wish I had done things a little differently with it, right? And it changed the way you thought about the world, and maybe not in a good way, right? Whereas the worst day of my life might have been an inspirational day that encouraged me, hey, I need to change things.

1:54:38 So I’m sure they haven’t with you as well. Yeah, what would we be surprised to learn about James Altucher? Some kind of weird thing you do, or a, I don’t know, well, just have it, well, sometimes I do this on stage, I haven’t lately, but I’ll sometimes breakdance in a comedy routine, more of the popping and locking than the breakdancing. Again, I think people put it all under one umbrella, breakdance, and crazy things about that, he might disagree. Right, why, I disagree, I disagree with me as well.

1:55:10 I think breakdancing is very different from popping and locking, but people don’t know that, sometimes you pop and lock, so people don’t usually know that about me, but so when I do it on stage it’s usually a bit of a shock, because it’s not like I’m bad at it, just like I’m sure you’re not bad at breakdancing, but it’s odd to see a 50-year-old white guy doing what you could probably do. I don’t know, I’m pretty, again, I’ve been so vulnerable and transparent over the past 10, 15 years, really the past 10 years, I’ve kind of revealed everything as it happened, you know, or things that happened, so I’m just, I don’t know, I’ve kind of said every bad thing in my life and I probably leave out the good things, but there’s nothing, nothing we’re saying there.

1:55:57 What keeps you awake at night? Nothing, sleep’s really important to me, like sleep, like if I, okay, the only thing that, what keeps me upset during the day is if I slept only seven hours the night before, because I really want to sleep eight hours a day. Do you worry about the world, do you think we’re gonna make it? I don’t care. Tell me about that, that seems kind of insensitive, but you know, I’ve even done a book, I did a book in 2009 about all the ways the world could potentially end, and The Wall Street Journal published it for me, Wall Street Journal combined with HarperCollins, and so it was like Investing for Disaster, but I was really more focused on the disaster part, and if you look at all the things that can go wrong in the short term, medium term and long term, first off, long term we have no clue, there’s a lot of science, but there’s a lot of science, and you know, you see conspiracy theorists or people arguing all day long on Twitter on both sides of, you know, every major issue.

1:57:07 Do I think we can do better for the climate? Sure, we can all have our role of not polluting, but that’s good for reasons other than global warming. You can have good reasons that go along with global warming without ever having to think about global warming. I have no idea whether global warming is going to happen, but I do think it’s better probably to not throw food in the street or have, you know, the gas in my car running all day long. So so there’s things you can do just for the sake of pollution and being a good citizen without having an opinion on climate change, so I have no opinion on climate change.

1:57:41 And then what else is gonna, you know, could nuclear war ruin the world? I don’t know, could have had probably a bigger chance in 1950 than now. Pandemics that could potentially be a problem, but there’s nothing we can really do about it except do work on vaccines and genomics and things like that. So I think, I think so, and also I don’t care whether I’m gonna die, probably 30, 40 years, I hope. I also see the rate of technological change is so great right now that 30 years from now the world is going to be so much more technologically sophisticated that a, we’ll know much better answers about pandemics, climate change, other issues, we’ll have solutions that we can’t even conceive of now.

1:58:28 Like we don’t need, you know, the biggest environmental issue in the year 1900 was the fact that every day there was 12 feet of horse manure on Wall Street because everyone was traveling on horses, they’d go down on Wall Street, there was just tons of people, didn’t know. They thought New York City was gonna go underwater because it would be buried in horse manure, and then 10 years later everyone’s driving a car, and environmental problems all solved. So we have no idea, even 5, 10 years from now, what innovations are gonna happen that are gonna solve all of today’s problems and create a new set of problems.

1:59:03 But we as a society like to have problems, that’s again the newsroom wants to scare us. So so I don’t worry about anything that people say, well, aren’t you worried about this? No, I’m more worried about, you know, our, am I raising my kids well, are my kids kind people, is my relationship with my wife good, is, am I doing the best I can of the activity, the creative activities that I do, am I being risk-averse in the businesses I’m involved in, and that’s already a lot of things to worry about.

1:59:31 I can’t worry about the entire world as well. If I do my thing, the world will be better. Do you have any ideas for me, because I really trust your opinion a lot, James, but any ideas for me for London Real, any suggestions for us for the future, or any questions for me? Yeah, I’m curious, I’m curious, I think you should now start putting more in writing what you’ve learned. You’ve learned so many things, you know, from London Real.

1:59:56 I could, you know, a listener can, let’s say the listener starts listening to 50 episodes ago, they could go back and listen to the last 500 or so episodes, or you can write down, here’s these incredibly valuable things that I found in common with all of these people, that, and I just want to say I personally do these things as well, they convinced me to personally do these activities as well, and I’m not saying anyone else should do it, but this is my story of what I’ve learned, the journey I’ve taken. Like I think you have like this great book and you now, and you haven’t done it yet. Okay, I appreciate that, and I do, I mean it’s amazing, I mean you know what it’s like, it’s part of the unsung benefits of hosting a show like this.

2:00:39 You can look at the views and you can look at the revenues or you can just look in the mirror and realize that, man, I mean, every guest that you’ve ever spoken to, for me at least, left something with me, like something with me, and changed me, right? Like you could, you can look at, like, let’s take Joe Rogan as an example. You could say, oh, Joe Rogan gets 90 million downloads a month, I should just quit doing London Real, which wouldn’t make any sense at all.

2:01:02 Then you’re just saying, you know, views, like Joe Rogan is a very quality show, but then you’re just saying views are the only reason you do something, and but you’re really doing it because, like you’ve said, you’ve improved with every guest, and you’ve been able to be more vulnerable as a result of seeing your guests be vulnerable, partly, you improved all your relationships while, while in the, in the past eight years, you know, you’ve had quite a journey, and not many of us, I will say, have had this opportunity to interview so many great and incredible people. Like again, we’re not reporters, you’re not interviewing someone for four minutes on Good Morning America, which is all they interview. So for you, we’re really getting into depth with people we admire and we’ve learned from and we’re trying to learn more, and that’s never happened in the history of the world before, so there’s almost a responsibility to share it in as many ways as possible.

2:01:59 Yeah, so true. Last few questions I always ask people, I’m gonna ask you, James, if you could pick up a magic phone and ring up 20-year-old James Altucher, because he’s an ethic walking over one of those bridges, and give him some advice based on anything you know now, what would you tell him? Write down ten ideas a day starting right now. It will change your life completely within six months, you’ll see such a huge difference in your brain, you know, rewire your brain, so do it right now, and that’s it, and drop out of college, got college right away.

2:02:30 The second part of that question, best advice you ever received, it could have come from a professor, a parent, Jim Cramer, I don’t know, somebody who’s you’ve passed their life throughout your life, any piece of advice that sticks out? You know, this is, I think a lot of people have given me good advice about life in general, like you that you can’t argue, like sleep eight hours a day, it’s so trivial yet it’s so important, or exercise as much as you can, or the benefits of laughter or meditation or, you know, you could, don’t let anyone tell you you can’t do this. But just on a real tactical level, you know, I used to, when I was a kid I played tournament chess, I was a young chess master, I was the junior champion in the state that I grew up in, and a chess teacher of mine once said, before you go, a lot of people have a tendency to play chess and then they look like 10 moves that they find an interesting move, they look 10 moves ahead and then they back up and then they start considering other moves.

2:03:38 He suggested, look at all of your options, look at all, maybe find five or six candidate moves first, what are all the reasonable moves in front of you, and then start going deeply down one of them, because a, one of those moves might be obviously the best, second, you don’t waste time going down one area before you’ve even identified, before you even know how much time you’re going to need left to go through the other options. So I think this applied to life, like look at all, look at all the options in front of you every, every day really, and unfortunately you can, you don’t have to make just, it’s not, get, life is not like chess, you don’t have to make one move, you can make many moves. So see what all the possible candidate options are in front of you before you, you know, before you do a deep dive, you know, risking time, energy, life, relationships, you know, just see everything that’s open to you and then decide.

2:04:39 So that’s good, I think that’s good advice. I think it’s good advice. Last question, to that 20-year-old who’s watching us or listening to us from around the world, they grow up in a completely different era, advice to them, besides the 10 ideas, besides don’t go to college, other advice to them to survive in this world? Yeah, you can, there’s always a way to skip the line. So you know, people will say, well, if you’re starving in a refugee camp in the middle of Africa, you’re not gonna send them the Vice President of the United States.

2:05:08 Fair enough, but for many things that you want to do there’s usually a much, much shorter and faster method of getting there than anybody else will tell you, and there’s a reason for that. If everybody knows that path, then that lane will get crowded, it’ll no longer be faster, look at slower. So I get there’s congestion on the, you know, highways, the fastest way to get to New York City from, let’s say, southern New Jersey, but if everybody took the highway at the same time it would be just as slow as any other path that we get congested.

2:05:40 So there’s always a way to skip the line or to get to where you want to go faster, and most people will disagree with you on it by definition, because that’s why it’s the fastest way. So says no matter where you are, and again for what your goals are, you know, the thing I always remind myself is a, it’s gonna be fine, and b, there’s a faster way to do things that’s just as quality but a faster way to do things. And this whole ten thousand hours, then you just don’t believe in it?

2:06:13 I did believe in it for a long time, but now I believe in something else called, slightly differently, the ten thousand experiment rule, which is, do as many experiments as possible and get good at doing experiments very quickly, ’cause a, when you experiment it means you’re doing something either you don’t know or society doesn’t know, b, you’re gonna learn from every experiment whether it was a success or a failure, and see, imagine those two things ten thousand times, you’re gonna know so much that you’re gonna trivially skip the line compared to someone who didn’t do those experiments. Was this the subject of the new book? It’s it’s moving towards that.

2:06:53 Yeah, okay, I’m still deciding on a title. I like it, and I think, look, back in the 1800s in Japan, when, you know, Miyamoto Musashi is learning how to be a swordsman, and maybe then 10,000 hours is the best way to not get your head cut off, but in this day and age with ideas coming at you left and right you can test things very quickly. Then I’m gonna go with your book, I think, or your ideas on this. Well, ten thousand experiments and do that stuff, could he, you know, go on YouTube?

2:07:19 He couldn’t try those things, right? Like you could try multiple platforms and to get your word out. Books is one that’s interesting for a variety of reasons, but there’s just an example I want to bring up from the Olympics in the 60s. You know, everybody for decades used to do the high jump by simply, you know, the high jump is when you run and jump over a pole or whatever, and people will just do it the normal way you would think, like, I’m gonna try to jump, spread my legs out and land on the other side.

2:07:52 Then this one guy, I think his name’s Dick Fosbury, he extended experiment, he’s gonna do it by jumping, he’s gonna back jump, he’s gonna jump with his back first over, and suddenly he breaks all records, and now before him nobody was jumping that way, now 99% of high jumpers jump that way, and that was an experiment that worked, and he skipped to the top of the line doing that experiment. So he would never have known if he was gonna try something that everyone said, no, you can’t do that, that’s crazy. Sure, everyone said it to him, he did an experiment and it worked.

2:08:26 I love it, 10,000 experiments. James, always a master, pleasure talking to you. I said here, Brian, thank you, ton of ideas just being here, so this is paid for the trip in full coming to New York. Thanks so much, looking forward to the book coming out. People can go to JamesAltucher.com to find your blog?

2:08:41 Yeah, you got multiple podcasts still going on? Yeah, Joe, and then Choose Yourself, great book, Power of No, you know, all that stuff can all be found on the website as well. Now let me ask you a question. Yes. Now that you know you started off London Real, and when I first time I was on it, when I was on it I was thinking to myself, okay, this is maybe popular in London, is it popular in the US, is it possible, you know, popular in other places?

2:09:06 You know, now obviously your brand is very much beyond London, and I think you have a, not a challenge but a slight rebranding adventure in front of you as you make this bigger, then you know it’ll continue getting bigger, and then you have to decide what does the words London Real mean, and is there a way to rebrand? I think that’s an interesting challenge. Yeah, I’d love to get your thoughts on that. I had a few people that come up to me and told me that, and then I think part of me, my knee-jerk reaction is like, you know, Amazon is still Amazon and it doesn’t belong in Brazil or it’s not from Brazil, but I think you have a point.

2:09:43 I mean, obviously it started off in London, a lot of what we do is signature London, but if you look at our numbers on YouTube, our biggest audiences in North America, it’s 45% North America. Right, I bet your biggest guests are from North America. Yeah, maybe not necessarily, but possibly, although I think we bring people like, you know, Priyanka Chopra and people like that to the scene where maybe they haven’t been featured on other places. But yeah, why do you think I needed a name change?

2:10:08 I don’t know, I think that’s one of those things, it was like, because there is a benefit to keeping the same name because now it has a brand, so that’s that, that’s always a hard thing to rebrand. You know, you know, The Real Brian Rose or Brian Rose Real or, you know, I don’t like Planet Earth, really feels, feels too green. So I don’t know, it’s an interesting, it’s an interesting thing. I appreciate those thoughts and to be continued. Yes, definitely come see us in London.

2:10:38 Well, I’m, you’re in town, come by the show because I got, we had 20 other things we can talk about. Excellent, thanks. Love to set up, love what you’re doing. And until next time, yeah, thank you, Brian. Thanks for getting in touch.

2:10:48 All right, thanks, James. Bye.

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