The Exchanges

Q What about, like, larger things in your life? Like, who do you think had, like, an impact, like a, my life would not be the same if not for that one conversation, that one idea with that person?

A Two people came to mind, uh, right away. Uh, the first is Herb Allen from Allen & Company, who I don't, I don't know well, um, These lessons came from one incredibly, you know, incredibly interesting conversation about, my sense of him, again, don't, don't know him well, is that he is uncompromising in his values. He, he does, he's maybe like the apex predator of like the thing I want to do, which is like picking and supporting people. I think that's what he's done for a really long time with unbelievable success. And that he is so incredibly uncompromising about how he does that and willing, I won't tell the examples, but like, I think willing famously to like throw away huge commercial opportunities just because the person wasn't who he wanted to support. Um, so sometimes it's literally a conversation with a person that just smacks you in the face and makes you feel, uh, validated maybe, um, for, for what you're trying to do. There's a gentleman named Reese Duca who's been Who's very, very private. Um, and you know, there's no content about him or interviews with him. I, I wish to God I could, he would let me interview him. I know, I know he never will. Um, Who has been incredibly impactful on, at like a philosophical level. He has, he has all these amazing little phrases, but his life kind of boils down to simplicity, the beauty of simplicity. He gave me this line one time, …

AI assessment note: “Two people came to mind, uh, right away. Uh, the first is Herb Allen”

Q and more experienced and obviously more successful, smarter and everything else. Just like, what, what I have to worry about? Like, what am I not seeing that could like cause me to stop? Like, I like what I'm doing. I love it. What am I doing that would cause it to like, for me to not be able to do that? And there's like interesting, like human questions about this.

A Well, the trap is Before you do the work to figure out the thing that makes you feel alive, there's this great line in the, um, in the Upanishads that it's always referred to abiding joy, like joy that doesn't, doesn't run out. You don't use it up, like you use up so many resources. As you use it, you get more of it. That's abiding joy. The target for most people becomes the traditional money power fame because those are worldly proxies for success that we all recognize and are for sure to some degree true. It's hard to get a lot of those three things without being successful in some way. I think those, those things are huge traps because they be, once you start to get one, it's the thing you start chasing. And it's different than chasing the feeling of being alive, that abiding joy of feeling alive that we talked about earlier, which you'll never run out of. That, that, that will always guide you well, always. And money, power, fame will not. And so I think the answer to your question or your worry is just, like, make sure you're chasing the feeling of being alive. And that, the intuition around that, and you'll be fine. And it's when we, it's when we get sucked, and I've, of course, have, just like everybody else, like, I've been intoxicated by those three things at various points in my life, and that's because they're intoxicating. It feels really good the first time you hav…

AI assessment note: “I think the answer to your question or your worry is just, like, make sure”

Q I'm having conversations, because we talk all the time, I had no idea Where this conversation was going, and it went in places like I learned stuff about you that I did not know. And so I really appreciate you saying yes to me and coming kicking and screaming on. I want to end by turning it around on you. What is the kindest thing someone's ever done for you?

A One is, uh, they're related. So I'll tell them in order. The first was I had a cousin. I come from an Irish Catholic family where when you go to the family reunion, you get a sheet that looks like one of those maps from the nineties where you just have to like keep unfolding it because there's just so goddamn many people. And so I have, um, I have cousins who are technically my like third or fourth cousins that feel in my family more like a first cousin. One of my third cousins was a guy named Tim O'Shaughnessy, and when I, I was a bad student in high school. I was like a very good student as a, as a young kid. I went to this giant high school in, ah, in Connecticut, like, 4000 students, and I just partied way too hard and didn't get good grades and didn't take it seriously, and so I, there was a day, ah, I remember it very distinctly. I was at a friend's house, having stayed up too late the night before, and my dad called me and said, hey, you know, you should, you should probably come home. There's a whole bunch of very small envelopes here from colleges. So I actually got, I got rejected from every college I applied to. Uh, the first time I applied to colleges, and I got all the rejection letters on the same day. It was a bad day. Um, so then I reapplied to some other schools. I, I had wanted to go to the University of Notre Dame, and I called them and I said, uh, where are …

AI assessment note: “One is, uh, they're related. So I'll tell them in order.”

Q And then how long from 28 till you realize this is going to be the, the simple organizing principle of how I'm going to live my life and spend my time?

A I, I, I actually don't think I could have articulated the principle as I just laid it out until very recently. So I, I could have told you about the power of Brett Victor's inventing on principle starting 10 years ago, or whenever I first saw it, but I would not have been able to articulate the principle to you cleanly, and that's because it's hard. It's hard to pin, for whatever reason, it's really hard to pin this down. Interestingly, I owe, I've never met Brett Victor. If he's listening, I'd love to meet him. Uh, I owe him an enormous debt of gratitude for one of my bigger career successes, which was, uh, I took his principle, not my own, but his principle of instant feedback and applied it as the primary design principle to software that I built in my last business, which worked really well. The software itself worked really well. The business grew a lot because of the software and the software worked well because of his principle. Of instant feedback on choices being made by the user, showing up in, in this case, in a visual that described their portfolio. And so I, I actually, before I had my own principle, I stole his principle to great effect, which just goes to show the power of a great principle. But I couldn't have articulated it for a really long time, and I can't explain to you why that's the case. I don't know.

AI assessment note: “I actually don't think I could have articulated the principle... until very recently.”

Q I did, well, one, the next day I log into my email, and it's just whoosh all the way down. Just like, no, no, no, no, no, no. But that is such an unusual instinct. If I'm being honest, like, I don't think I would have done that. What the hell is going on there? You didn't see it as a competition. You didn't, what, what was, what was happening?

A The first thing that flashes to my head is, you know, in my show, I've always asked people the same question at the end of what's the kindest thing anyone's ever done for you. Some person on Twitter or something went and compiled every answer, there's 500 answers or whatever, and categorized them and like made a pie chart of like what people say, and something like two-thirds of the answer to this question were the same, which was the kindest thing was some person made a bet on me, the person answering the question, before I deserved it, or like they saw something in me that maybe I didn't even see in myself. They, they bet on me before others would. And that was the answer to the, the kindest thing. And when I was 26, I, I became very interested in, ah, all of the, I studied philosophy early in life, and I've always been interested, interested in that stuff. But I became really interested in the religious texts, like all the world's religious texts. And I was, I was kind of, ah, I was in a weird spot in life. I kind of hadn't found anything to do yet. I wasn't that good at anything. And I was searching. I was always searching for like, what the hell should I do? What the hell's the point of all this? And I found this passage in the Upanishads, which as a book is probably the most important book to me. And the Upanishads is this collection of stories from many thousands of year…

AI assessment note: “The first thing that flashes to my head is”