This is an auto-generated transcript of Never Enough Podcast Episode 7. It may contain minor errors.
Andrew: What are you interested in right now? What are you obsessing over?
Derek: Oh, my "Useful Not True" book—not for the sake of selling a book, I don't care about that—but just the subject of choosing beliefs because they're useful, not because they're true. Last night I spent hours writing and thinking about what is it that makes beliefs useful. And I came up with some traits. Things like: they help me go directly for what I really want instead of some roundabout way. So if you're thinking that you need a college degree to get status, well then maybe there's a more direct way to go directly to the status instead of four years of college. Another trait is useful beliefs are often selfless—you kind of zoom out and realize you're just one of many billions on Earth.
Andrew: I just did an interview with Mark Manson and he basically says look, the world is pointless, life is meaningless, but you need something to hold on to. Is it that sort of thing—like inventing truths for yourself?
Derek: I think Mark is just projecting his value there, saying you need something to hold on to. I'd say that's not true—that's just him saying this works for me and I'm going to prescribe it for others because I think many could benefit from this. But it's not necessarily true.
Andrew: How did you come to write that book?
Derek: It was more that the subject was underneath everything I had been talking about for years. Like my "Anything You Want" book—I'm saying things like "business is not about making money, business is a way about making a little utopia where you can make everything the way you want it to be." Well, that's not necessarily true—that's just one point of view that helps me. It helps me get more intrinsically interested in creating a good business.
The harm is in declaring it to be absolutely true—like everybody needs to do this. I've always been sharing beliefs that are useful to me that are not necessarily true. And every now and then people would push back saying "hey, that's not true" and I'd say "I know it's not true. I never said it was true. I choose beliefs because they're useful to me, not because they're true." And after saying this for years I thought I should write a book about this.
Derek: This is book number five for me, and the five books have come from four different motivations. The first book, "Anything You Want"—I never intended to write a book but Seth Godin called me and asked me to, so of course I said yes. The next two books were collections of articles. My fourth book, "How to Live," was a flash of artistic inspiration—like an art piece that took me four years to make, where it had 27 chapters each with a strong opinion of how to live and each chapter disagreeing with the rest.
Andrew: So what was 38 to 54 like for you?
Derek: The last 16 years have been a lot of exploration. I think about the difference between an explorer and a leader. Where the explorer goes off to uncharted land and just starts poking around, taking every little turn.
An explorer is a pain in the ass to follow because the explorer may change his mind daily. But then when the explorer finds a harbor that looks like a great place to set up a town, then the explorer sends a message back and a leader is appointed. A leader goes in a straight line—a leader says "here's where we're going, here's how we're going to get there, follow me." And a leader does not explore.
Derek: I had 24 years of my life from age 15 until 38—I was head down and focused on one thing. I spent 15 years head down saying I'm going to be a successful musician, that's it, don't distract me. Then at 29, while selling my music, I accidentally started my company and I just put my head down for 10 years on that one thing. I was like, I'm gonna make the best damn little record store.
Derek: And so it wasn't until I was 38 that I really lifted up my head for the first time in my life. And I started doing things the opposite of whatever I had been doing. If my instinct was telling me to turn left, I would turn right. And if everything in me was telling me to stop, I would go. And I did that to deliberately scramble my patterns and force exploration.
Andrew: When I met you—I hadn't seen you, I don't think, in 15 or even 20 years—I think we met at the TED conference in 2008. And I looked you up, I was in Wellington and we had coffee. And you said something really interesting—you said when you sold your company, your urge was to do it again, to prove to the world that you were not a fluke. And you said, "I wasn't going to play the same game that I'd already done."
Derek: I optimize for personal growth, not for bank account growth or status growth. So when I sold CD Baby, yeah, my first thought was I can leverage this, I'm going to go to Silicon Valley and be a serial entrepreneur. And I got a few months into that and I realized that if I were to do that, it wouldn't really be personal growth—it would be bank account growth. I'd be doing the same thing I had been doing for 10 years.
Derek: I thought, well, real growth would be to do something truly different—not doing the same thing. It's kind of like a quote I heard that real rebellion is not wearing black like everyone else—real rebellion feels like wearing a clown suit to high school. So true personal growth is not doing the same thing you've been doing, but a little more. So I halted my plans, I left Silicon Valley, and I went to India and Iceland and started traveling the world.
Andrew: You used the term burning the boats. You talked about how you took radical changes to enforce that you would not continue down the path of money and business.
Derek: The most direct radical one was renouncing my US citizenship, which came from saying I love America, it's my comfort zone, therefore I'm going to ban myself from going there anymore. I used the metaphor of burning the ships to prevent retreat.
Andrew: You also did that with your finances.
I already had about $4 million in my personal bank account as net profit. I was the sole owner of the company and I had this agreement to sell the company for $22 million. And I thought through about what I would do with $22 million and I just thought—I just don't want it. The $4 million I had saved was after expenses. I had already bought a car and bought a house. What else are you going to do with it? So I'm just going to give it away. There are people literally dying because they don't have money, and I'm sitting here trying to figure out what to do with my money. My lawyer said if you're really serious, we can structure this so the entire $22 million goes to charity. And I said I like that, because then the money never touches my hands—I can never be tempted. And that's what we did.
Andrew: And how do you live now?
Derek: I had that $4 million and that has grown since then. I just stick it in ETFs. Occasionally I turn to my private journal and ask, "what would I do if I suddenly had a billion dollars?" And every time I really think hard, I just can't think of anything I would do with it. There's nothing I want. So I still think I did the right thing.
Andrew: You've got a lot of friends that are very wealthy. How do you see wealth negatively impact their life?
Derek: It seems to throw off perspective. My first anti-role model was a friend who had sold his company for 30 million and he said "yeah, it was only 10 million pounds" and I was like, God, I hope I never say that. I think that's harmful. I think we should never lose perspective on how much money that is.
Andrew: Since then, you've left the idea of accumulating money behind. And how do you spend your time?
Derek: A typical day for me is I wake up at 4:00 or 5:00 a.m.—I wish I didn't, but for some reason my brain goes "I'm ready, let's go."—and I start writing. I am either writing diaries, books, code, emails—basically finger on keys, writing from 5:00 a.m. till about 10 or 11 p.m. with some short breaks to eat, maybe take a walk in the forest.
Andrew: Your book "Hell Yeah or No"—what are some things that you are hard no on?
Derek: Never do heroin—that's a good one. Here's one: I've made a really clear decision that my boy is my top priority. I've only got one kid. This is it. He and I talk almost every day, we're like best friends, and he wants me to be here in his life. So I want to be here where he is, even though I know I could just hand him off to his mother and go be somewhere else. He's my top priority. So my only real hard no in life is anything that would hurt our relationship.
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