The Exchanges

Q And so, um, but I think I thought that was really fascinating because it's like an entirely new format, but like you're doing something different than most podcasters had done before when they're trying to evolve their podcasts. Like you've been really obsessed with it for a really long time. Can you just like talk about how you got into podcasts and then the evolution to today?

A I think for me, I know some people use podcasting as entertainment. I just think they're one of the most like miraculous tools for education. So the way I think about what podcasting actually is, I think podcasting is, uh, the printing press for the spoken word. And so since I don't have memories before, I had a love and obsession with reading. And so probably, I don't know, five, six years old, I just absolutely fell in love with reading. It's something, it's a daily habit of, like essentially an unbroken daily habit that I've had for decades. And it's essentially just taught myself everything that I wanted to know through books. And When I was younger, I realized, oh, like I started getting obsessed with talk radio because podcasts weren't a thing at that time. And I was like, oh, this is just like another form of education. Like if I'm not looking at a book, I can be listening to somebody else talk about a subject matter. And at the time you'd have to like be in the car and it'd be like AM radio. And I didn't even care what the subject matter was. I was just so voracious for information. I was looking for, now looking back, I was just looking for useful information on how to build a great life. Cause I didn't have, I wasn't raised in an environment where I had any mentors or saw any really good Role models by any means. And so I think this was just me trying to like find, yo…

AI assessment note: “I started getting obsessed with talk radio because podcasts weren't a thing at that time.”

Q But like, you can, you can totally tell the, Principles, like the values, how wholesome he is, all of that kind of stuff. So why did you choose Michael Dell as your second interview?

A I think Michael Dell's autobiography is like one of the best autobiographies written by a founder ever. He's also been unbelievably, like, generous to me. Like, he had sent me a DM, like, years ago, like, I don't know, 2023, before almost anybody knew who I was, and he's like, you, I think he said, like, you're, you're really good at this, your podcasts are A+++, and I think there was, like, true little trophy emojis, and then, um, when I went to meet him for the first time in Austin, this is before we recorded together, we spent, like, five hours talking, and, like, what is an hour of that guy's time worth? Like, it's inconceivable that he would be so generous with me, And then I, I brought the book along with me so he can see like the, I mean, he listens to podcasts just as you know, but like the effort that I put into what I'm doing, like this is not a game to me. Like I'm trying to be the best in the world at what I'm doing. And for him to like, I didn't even see that he signed it and went back to Malibu and like two days later opened the book and he's just like, David, I think you're, you're a master at your craft. And he's like LinkedIn that line before he's like tweeted. He's just been unbelievably, uh, generous to me. In fact, He might not even know this, but I have this deep multi-year partnership. And the way that came about.

AI assessment note: “Michael Dell's autobiography is like one of the best autobiographies written by a founder”

Q That reminds me a lot of your conversation. I said conversation, not interview, by the way, uh, with Brad Jacobs. Cause he is also all about embracing problems, by the way. Amazing. Like what he put you in his new book. What was that?

A Okay. So Brad Jacobs is a funny guy. Uh, probably the most energetic person I've ever been around and he's 68 or 70 years old. So Brad Jacobs has started, I think eight, Now eight separate billion dollar companies. And he, for a long time, he was like my LinkedIn reply guy. What? Yeah. So I gotta tell you the story. This is a hilarious story. So the first podcast he ever did, I think he was interviewed by Patrick Shaughnessy on the best, like the best. Okay. And if you, they recorded in Patrick's got a studio in New York. He's got a studio in Greenwich and obviously shout out to Connecticut, shout out Connecticut. And Brad lives in Greenwich and tries to avoid the city like a plague. So he recorded in the Greenwich studio. If you go upstairs in this, like, house, this office house that Patrick has, the entire upstairs attic is, like, uh, like, looks like a library, and most of those books were covered on founders, or not most, but, like, half the books were covered on founders, and so he has, like, references to founders everywhere, and Patrick calls me after that happened, and he goes, dude, I was just with Brad Jacobs, you know who this is? I was like, yeah, he sent me, like, his, his new book yet. This is years ago, so this isn't the book you're talking about, which we'll get to in a second, and he goes, You know the founders guy? I love founders. And so he starts sending me…

AI assessment note: “This is years ago, so this isn't the book you're talking about, which we'll get to”

Q If you could define twenty-twenty-six in one word, what would you want the word to be?

A It can't be one word, but I am very interested in seeing how far I can take this. And I said, I just said I spent a bunch of days with six of the biggest podcasters in the world. I was talking to Patrick on the, the, um, The drive over here. And his whole thing was like, I'm so glad that you do what you do in the sense that you go around, you like collect all this information. You just essentially don't think about anything but podcasting. And he's like, cause I'm not interested in it at all. I like one podcaster. He's like, I like you. He's like, I don't actually like podcasters is what he was telling me. And he's like, and if you weren't doing what you're doing, I'd feel like FOMO, like I, what's going on in the world where I can just like call you and you can just like data dump on like what's going on with me. And I, I text, this is like two Saturdays morning, it was like seven in the morning, and I text, ah, two members on the, of the team of the new podcast, and I was just like, we're gonna, like, take this as far as it goes. Like, I don't know where we can go, I just know no one else is gonna take it farther than us. And so, the way I would describe it is like, I don't want to get to the, and definitely not the end of my life, but certainly not the end of next year, without, without knowing, like, I wanna push it to the limit. And I don't mean to break, I don't mean to l…

AI assessment note: “It can't be one word, but I am very interested in seeing how far”

Q Okay. Speaking of business, you mentioned you want to build a show like Charlie Rose. What does that mean?

A So I always think about this goes back to differentiation. So let's back up. I think episode number six of the new show was James Dyson. That was one of the best days of my entire life because James Dyson, his first out of all, all the 400 plus biographies of entrepreneurs I read, His first autobiography called Against the Odds is by far my number one recommendation. Everybody's like, give me like a top 10 list. I was like, no, I don't have a top 10. Listen to all of them over and over again. But if you want one, go find this hard to find book and read it over and over again. I've read it, I don't know, at least five times. I read his second autobiography at least twice. I read his History of Great Inventions, this encyclopedia that he wrote. I've watched all his interviews. He gave me the motivation to not quit when I was going through a very difficult time. Five and a half years of struggle before I Built the podcast into something that was like sustainable. And then it grew from there. He did 14 years of struggle. And the whole time I was like, this guy did five, 14 years of struggle, 5127 prototypes. He is failing his entire life and he didn't give up. I can like persevere through this. And so it was very important. He was the number one person in the world that I wanted to meet and he couldn't have been better. So sweet and witty and impressive. He owns one of the, he was …

AI assessment note: “So let's back up. I think episode number six of the new show was James Dyson.”

Q What'd you think of the pushback on it?

A There's actually interesting philosophical topic we could talk about here. Um, In many cases, you see this in a lot of the biographies, and then if you just, you know, study public figures anyways, you realize that a lot of the things that their greatest strengths can also be their greatest weaknesses, and the closest I have to, I was very skeptical my entire life because I'm not a trusting person, and I think there's a good reason why I was a trusting person. I keep, you know, I'm interior by nature. I don't let new people into my life easily, I keep everybody, like, at an arm's distance away. Once you break through that, like, I am kind of like, my hard exterior is, like, kind of soft. You have a little bit of this too. I, I do think it's very beneficial for you to be able to organize your thoughts with another person that you trust, that they care about you, that they, they're not transactional with you. And that they want, they have your best interests at heart, and so, um, there's this guy named Sam Hinkey who plays this role in my life, in addition to, like, a lot of my close friends, where I, like, I, there's a handful of guys, maybe five, that I do trust, and I talk about, like, almost everything else that I'm going in my life, but this is much more of, like, I consider Sam, like, a, like, an older brother. We're friends, but, like, Almost like a coach, even though he w…

AI assessment note: “There's actually interesting philosophical topic we could talk about here.”