The Exchanges

Q To work with, and I loved the, the, you know, some of your, your stories that you've told about him, but I was wondering, like, he not only was really difficult, but came up with wild ideas and worked with really spiky people. Do you have a favorite story from George Lucas, or do you have something that you think George Lucas would teach people that most people don't realize?

A There's a great biography of George Lucas called George Lucas to Life. It's written by Brian J. Jones, who's also Prolific biographer. He has a bunch of biographies I like, but it says, uh, the most important line in that book is that George Lucas unapologetically invested in what he believed in most himself. And he was another control freak, and one of the biggest bets he did, so he, he did this movie called American Graffiti, and he didn't have any leverage at the time, because he was still a rather unknown director. Again, another thing that was very rare is to have directors in their early twenties. The director that kind of blazed the path for all these guys was a guy named Francis Ford Coppola, who was running major, big budget, major movies in, he was like in his late twenties. He's probably twenties, around 27 as well. And so, uh, Steven Spielberg saw this, George Lucas saw this, Brian De Palma saw this, all these, uh, these directors that were, and filmmakers that were friends with each other, and I think Coppola's like, you know, maybe half a decade older, maybe a decade older, and so he played a huge role, but at the time that he's making American Graffiti, which is one of the best returns on investments, I think the movie, he did the movie for like a million dollars, if I remember, and he made like fifty seven million at the box office, but because he didn't have cr…

AI assessment note: “George Lucas unapologetically invested in what he believed in most himself.”

Q Do you think you have to be obsessed to win? Like, if you want to be one of the greatest, do you have to be obsessed?

A Any, is there anybody I've talked to that wasn't obsessed? So we can go back through the, the, the guest list. So, 20 years, Danuak, obsessed. He couldn't work on anything. He just stepped down, because his natural state is to work on multiple companies at one time. And we should talk about founder archetypes, because we're working on this project together, which you might find interesting. Uh, and really the importance of like knowing yourself, and then you're not gonna be successful unless you can build a, a, a company that's a reflection of you. You know, essentially like a, uh, an echo or a shadow of the founder. So Daniels had to be obsessed if Spotify wouldn't have worked. Michael Dell is still obsessed to this day. He's obsessed with puzzles. And he just looks at like reinventing, constantly reinventing his company as like a giant puzzle. So he's been doing it for 40 years. Uh, Brad Jacobs has 43 years of experience as an entrepreneur. He started eight separate billion dollar companies. You should get him on here. He's a fascinating character. One of the most.

AI assessment note: “is there anybody I've talked to that wasn't obsessed?”

Q seems tantamount. What are you thinking about what's going on right now in the world of AI? What do you think the greatest entrepreneurs are thinking? Does this matter? Is this always just the same thing? Is there always just some new industrial or, or technological revolution? And there's opportunity in every market, and we need to not be defeatist about it. Like, how, how do you think about this?

A If you agree that the best definition or a great definition of a business is what Richard Branson said, that, um, all the businesses is an idea that makes somebody else's life better. There is always infinite ways to make somebody else's life better, so there is, therefore, there's always infinite opportunities, in my opinion. With that said, I do think you do not ignore technological phenomenon and technological revolutions, uh, We're obviously going through one now. I think you should use like, so what I do is like, I just force myself to learn and to build these into my workflow now. So I'm sure there's going to be AI generated podcasts that can do exactly what I do. A hundred percent. Like I would imagine that's going to happen relatively soon if it's not, you know, this year, next year, five years from now. Um, and so like, just to use the tools, the technology, cause all technology is my best, my favorite definition of technology is Um, from Peter Thiel in his book Zero to One. This is just a, technology is just a better way to do something. And so I'm just using them to be better at making a podcast, and hopefully that podcast, and that information in the podcast makes somebody else's life better. See how it connects? Now, I think the mistake when you're looking at history is like the only thing constant is change and technology is never going to stop. And I think the sm…

AI assessment note: “there is, therefore, there's always infinite opportunities, in my opinion.”

Q Yeah. Do you think that entrepreneurship is a trauma response in some ways? Like it's like PTSD and so you become an entrepreneur.

A I actually have a lot of people, you know, cause when you think about these, these life stories, there's usually some kind of like unhappiness, uh, usually an issue with like their parents, like a relationship with the father. Is a big instigator. Maybe they grew up in poverty. I would just say that I don't think it's prerequisite for extreme success. It's just that most humans grow up in bad environments. And so I think you just, it's literally just a bigger sample size. Um, there you can, you know, grow up with, you know, loving household and still have extreme success. I don't know if it's a trauma response. I do think I have a different view of this. Like I, I hope I just talking to Toby Luque of Shopify about this. He says something interesting. Cause I had a long form conversation with him for the new show. And he said on at the very end, he's like, oh, me and you have the same job. Our job is to create more entrepreneurs, and I never thought about that because he was a fan of both founders of the podcast founders too, and I would like to help entrepreneurs surface useful information for them, but I don't know if you can create more of them. Um, his, maybe he could. I just think that there is something Almost innate in it. It's like a personality. I don't think you choose to be an entrepreneur. I think, like, there's this great line from Jeff Bezos where he says, we don't…

AI assessment note: “even if they, that entrepreneur type didn't even have trauma, they still would do”

Q And a little, like, slightly autistic and really obsessed with the game of video?

A No. Well, he is, he is an obsessive person, but I met him through Blake Robbins, who, uh, Blake Robbins is a investor. He used to be at Benchmark. Now he's on Fond. But I think his Twitter bio says he, like, hangs out on the, the edge of the internet, and he finds, like, weirdly talented people, and he's like, hey, will you meet this kid? He's in from Europe. He's in New York. He's obsessed, he's obsessed with a single podcast, and it's yours, and I was just talking to the kid because I thought he was talented. I was like, you should move to America. He was doing all this other way to make money that he wasn't passionate about, and I was like, just how much do you need? Like, what if you just made these shorts for me? Right? How much you need. Named his price. I was like, done. Didn't even negotiate with him. And now I'm helping him because he's gonna be one of the greatest filmmakers, I think. He, like, mastered short form. Now he's making short movies. Then he wants to make, like, he wants to be like Christopher Nolan and Steven Spielberg. And I was like, listen, I'll, to the degree that I can help you in any way, like, you've been so helpful to me. Like, if I can make an introduction for you, if I could, I'd invest in you, and I don't even like investing. Like, I'll do whatever you can because you're so talented. Like, I just think about things in terms of people, but This a…

AI assessment note: “No. Well, he is, he is an obsessive person”

Q Have you met a lot of incredible founders or have you covered a lot of incredible founders that you would call nice as like the first word to describe them?

A My initial answer would be no, but that's probably not true. So my personal hero, Uh, there was three people I wanted to meet, right? And accidentally, unexpectedly, I met all three of them last year. It was James Dyson, Jeff Bezos, and, uh, and Jimmy Ifein. I spent, I don't know how many hours talking to Dyson. The episode I did on the new show, David Senra, that episode, it's episode number six. I don't even think we're labeling, numbering them. That was one of the best days of my life, because that guy's book changed my entire life. We can go into more detail about that if you want. And it's somebody I read about. I read his first autobiography at least five times. I read his second autobiography at least twice. I read his history. Talk about how so many people that are great with what they do have this love. And he says he's obsessed with the past and studying history. He wrote an encyclopedia. He considers himself an inventor, not an entrepreneur. He just became an inventor so he could, so he could continue to, or he just became an entrepreneur so he can continue to invent. Bezos thinks about it the same way. But he wrote, James Dyson wrote a book on, it's called A History of Great Inventions. He literally cataloged, I don't know, there's like a hundred or 200 inventions in there. He tells the story of these things. Read that book. And he was unbelievably kind and generous…

AI assessment note: “My initial answer would be no, but that's probably not true.”