Kevin Rose On Staying Healthy With Entrepreneurship, Zen Buddhism, And Being Vulnerable

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2:07Welcome to the Daily Stoic Podcast, where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are and also to find peace and wisdom in their actual lives. But first, we've got a quick message from one of our sponsors.

2:57Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. I was proud of myself yesterday. I was heading over to do this interview, which I was recording in Los Angeles. And I like pretty much everything that could go wrong. well, they asked me to get there 15 minutes early, which I did, which I was more than on track for. And I'm driving there across LA, hit a little traffic, so I'm running a tad behind. Then I can't figure out where to park. The building is sort of this conglomeration of buildings and I wasn't sure where the parking garage was. So I'm circling the building, trying to find the parking.

3:40I can't see. I call my producer and one of them doesn't answer. Then And I call the other one and go, hey, did they say anything about where I'm supposed to park? And they couldn't find out. And so I was like, I found some street parking. I was like, you know what, I'll just take this. And I go to pay. And then I realized, oh, I forgot my wallet. I've sort of been on vacation and I don't have my wallet because I haven't been using it. And then it's like, great. So I ended up finding the garage underneath the building or related building. I get in there, I go in the wrong spot, and then I get in.

4:18And all I'm thinking now is I'm already late, which isn't great. And then I'm like, I got to defer how I'm going to pay for this when I leave. And anyways, interview goes good. I'm leaving. I thought maybe the parking thing will have Apple Pay. It does not have Apple Pay. Then I'm talking to the valet guy in this other part of the garage. And he's like, look, you can just Venmo me the money, I'll wipe it through. And I didn't have Venmo, so then I had my wife to do it. This whole thing. But it was embarrassing. It was stupid. It was annoying. But normally, like if I'm doing an interview and then I was trying to get home in time for the kid's bedtime, it's not that the thing stresses me out, but it's like the other things that I'm trying to do, right?

5:07I got to get there by this time. And if I don't get there by this time, then that's a problem. And then I don't want to miss bedtime. and I don't want to inconvenience anyone. Anyways, I felt pretty good. Like I handled it all super calmly. I didn't freak out. Just to remind me, look, the stakes here are pretty low, right? I'm not going to go to jail for not paying for parking. I don't know. I guess if I parked in the street parking, sometimes I tow in LA, which has happened to me. I didn't want that to happen. But anyways, I feel like I handled it calmly, effectively. I was like, there's obviously a solution.

5:42I'll work through the solution. was the worst case scenario. I take an Uber all the way back to my place, get my wallet, take it all the way back. It's more expensive, takes forever. But again, just handle it calmly. Don't make an already frustrating or dumb situation worse. Don't make it even more stupid. Don't compound the air. That's what I was just reminding myself and ended up being fine. And I didn't let it affect the interview, which is good because I was really excited to do this one. Kevin Rose is someone I've known for a very long time. We talk about this a little bit towards the middle of the interview.

6:16I show a picture of when we first met, which would have been in 2007. I was living in LA at the time. I just dropped out of college. I was working at this talent agency, which is probably where some of my parking PTSD comes from. The first day I lived in LA, my car got towed and got many, many tickets also, which I could not afford. Anyways, I've known Kevin a long time, and I think you may have heard him on the podcast once before because he interviewed me for, I think, the launch of Lives of the Stoics, and I've been on his podcast, which is great. But Kevin is a serial entrepreneur. He founded Dig, Pounce, Milk.

7:08He's now the CEO of Proof. He's a partner at True Ventures. He created the intermittent fasting app, Zero, the meditation app, Oak. He's the CEO at Houdinki. He was a general partner at Google Ventures. He's invested in Uber and Twitter and Square and Nextdoor and Ripple and a bunch of other huge companies. He's very good at what he does. He's also, as you'll find out in this interview, a student of Stoicism, a student of Zen Buddhism. just a really interesting all-around guy, a really interesting all-around nice guy, as we talk about in the interview. And he was in Austin a couple months ago for some crypto conference, and he was going to come out to the painted porch and do it, but the timing didn't work.

7:51And he said, hey, I'm in LA now. When you are in LA, just come and we'll record it in my studio, which is what we did. And so that set up me being a little bit not on my home turf, which is probably also a bit stressful, but took it in stride, tried to practice stoicism on a sort of practical mundane level. And I feel good about it. And I just wanted to share that story because I'm not some stoic sage. I'm just a normal person like everyone else trying to not let life get the best of me. As Kevin is too, you can follow Kevin at Kevin Rose on pretty much every platform. You can go to kevinrose.com.

8:28You can listen to his somewhat intermittent off and on podcast with Tim Ferriss called The Random Show and should check out a bunch of his stuff. I'll link to it all in today's show notes. And I hope you enjoy this interview.

8:58I saw your place right when you were finishing it. Yeah. Yeah. Yeah. It was a fun place. It was awesome. I'm kind of bummed if you sold it, but. But then are all your people are here anyway? Yeah. I'd say like, what do you think about 30 % of our staff is here? Something like that. Yeah. It's the single largest concentration. Yeah. Really? For sure. We've got like 40 people or something like that, which is crazy. For the NFT thing. Yeah. For all that. Because I feel like you have like, we should talk about this, but you always have like 50 things going on. I always tend to dabble. Yeah. Yeah. I do feel like, like if I was to describe you, I would say you're someone who gets like lit up by stuff.

9:34Like you get really excited about something. And then whereas a regular person would be like, oh, read about that. Or like, oh, I'll follow that. you're like, I should start a company about that. Right. That's a big problem of mine. Is it? It's actually a huge problem. Why is it a problem? It's a problem because I get so excited that I just go all in and there are no safeguards. And so I'll launch something without even considering any of the other potential ramifications of what that means. Like in terms of my time, time with my kids, It's like all of it just like, I just, the excitement is so real.

10:12Yeah. It just sweeps me up. You're like when following your passion goes wrong. I don't know that. No, no, I'm saying like people say follow your passion and you're like, it gets me in trouble. You're telling me some stoic like line or something I wasn't familiar with. No. Yeah. I mean, it's like, I've always had this mind that has just jumped all over the place and shiny objects are really attractive to me. and when I obsess about something, I go pretty deep and get really excited about it. And that either leads to an investment in a company related to that or every once in a while I just build something.

10:48Especially if it's technology related, I'm going to just jump in and build it. Are you able to be somewhat rational about it? Like, is this viable or not? Do I want to do this or not? Or is it just you just go and then you look back and you're like, oh, I guess I started another company. No, I mean, I have to believe that there's going to be, at this point in my career, if it's a lifestyle business, I'm really not interested. I want to go after big, world-changing ideas that have the opportunity to be something that is a billion-plus dollar outcome. Wow. I mean, that's what we look for when we do venture-related investments.

11:25It's kind of my venture training that's in me. We're not trying to build the next little local taqueria. we're going for something much, much larger. But is that, but, but so it's got to intersect with what you're personally fascinated by. And then it has to have the ability to scale, but it doesn't seem like all the things have the ability to scale. Some of them just seem like they were just really interesting to you. Well, yeah, that's a great point. There's been a couple where I have said to myself, this needs to exist. Yeah. Why not? And it's not going to cost me, like it's not going to take up, or it's not going to cost me a lot of money, A, and it's not going to be something that I need to, tend over time.

12:02Like for example, I launched a meditation app called Oak. It's completely free. And there was never a business model behind it. It was just that everyone was charging like$10 a month for evergreen free information that's in books where you're just like, shouldn't there be a free version of this? And so that app is still around and it has tens of thousands of great reviews and it's just doing its thing. And no one has updated it in eight months if you look at the build release on Apple. So those types of things I like to do. I've read a couple books, like Zen books, that needed to be put into audio format that hadn't been put into audio format.

12:48So I just paid to have that done. Things of that nature. You're like, I have the money, why not spend it? It's like the philanthropic kind of side of like, how can I give back in that particular kind of way? So that type of stuff I'm into for sure. There's a, you know, that show Eastbound and Down? Yeah. Someone asked him if he was like training for a marathon or something. And he said, no, I'm not trying to win at my hobbies, which I think about all the time. But does it suck some of the fun out of the activities that you turn them into businesses or jobs? Yeah, it does when they hit a certain scale.

13:25And for me, it's like if it's just the day-to-day maintenance and growth, meaning like, for example, I started an intermittent fasting app called Xero. And that's grown into millions of users. And it got to this point where I was like, okay, we've built a great fasting app. Now there's content that you want to layer on, make sure people are doing it in a way that is backed by legitimate science. It's a lot of kind of day-to-day grind on the content side. and the excitement of the early days of just figuring out the UI UX challenges, figuring out how to track fast when you switch time zones because you flew to London.

14:09Weird things like that where you just have to think through the little edge cases, those are all gone. And so that's where I get really excited. And once that happens, there are professional CEOs that are much better than I am to bring in and run to scale those businesses. So that's what I've done before. So is that a skill you've had to learn too, the ability to hand stuff off or delegate? You can be the fun, exciting idea person, but you can't. Yeah, I've done that multiple times. That's like Houdinki as well, the high-end mechanical watch website. We've got 150 employees today. When I was there, there was four or five of us, and they had no mobile app.

14:51They had no e-commerce experience. And so like building all of that from the ground up was just a blast. And so watching people consume that on a mobile phone and get notifications and do live streamings and all these things from all the major events, like building that tech from the ground up is what excites me. One piece of parenting advice I got is like that it's not, you can't like come home, like wind the kids up and then be like, well, now I got to go do my thing. Do you know what I mean? Oh, yeah. That you have to think about, like, if you're someone who loves startings, the metaphor I take from that is, or the analogy, is, like, if you're someone who gets excited by, like, starting stuff or having ideas, you have to realize, like, that becomes somebody else's problem after.

15:34And so either you have to be able to delegate, you have to be able to let stuff go, or you have to be able to have the discipline to not start the thing. Because, like, when it gets boring to you and you move on, like, now it's somebody else's mess. Yeah, one of my good friends, another entrepreneur, Brendan Mulligan, told me I need to build an app to remind myself not to build apps. And that was basically his advice to me. It's very true though. Also at the same time, there's been a bunch of stuff I've just shut down. Because you get to the point where you realize you've turned over enough cards, there's nothing here, and there's no sense in just trying to do another pivot or another iteration.

16:14Let's just have the discipline to go in and kill it and move on. Yeah, my wife's brought that up to me too, where it's like, oh, I fell in love with this thing and then I bought this investment property. I started this thing or we started this. And then she's like, I have to handle all this paperwork. You know what I mean? Or like that mental, like you're not, I'm not thinking about it, but it's keeping her up at night and the ability to, you have to be able to empathize or yeah, call it and go, I thought this was going to go the distance and now it's not. Right. I mean, the thing that I've realized in my life, and I'm sure you probably preach this on the regular, is that every object that I own, everything is a subconscious mental burden, without a doubt.

16:54Yes. There's like, it can be the wheelbarrow that has a flat tire sitting out in the backyard. Yes. Like, at some point, I know I have to go figure out how to get that fixed, right? Yeah, yeah. It's like, so it's anything I am, I've like reduced the stuff that I have by like an order of magnitude over the last like five years. Yeah. Although that takes its own discipline too. Like, so my wife and I will be like, it's too much stuff. We're too stressed. And then we'll be like, well, let's make a list of all the stuff that we know is causing us angst or misery or anxiety. And then we're like, but which ones will we eliminate?

17:29And then we're like, but we like that one. So you get yourself into the situation through a lack of discipline, and then you don't have the discipline to get yourself out of the situation, which requires hard decisions or hurting people's feelings or taking a bath. Or just the sunk cost fallacy is really, really hard to overcome. There's a lot of ways. There's little things that I've done. Like a hard one for parents is the shit your kids make you. Yes, of course. You know what I mean? Like my daughter made me this amazing multi-layered like paper mache birthday cake for my birthday with like paper candles and everything.

18:06And this is when she was four. And she must have spent like three days. And I couldn't come over. It's like, dad, don't look, don't look. I don't come over here, you know. And I have this thing. It's massive. And it's just sitting in the corner of my office. And that stacks up with all the other things. And I'm like, okay, at some point I got to go and record this with my phone. Show off how beautiful it was, how much it meant to me. Talk to that. so eventually when she inherits that video, she'll get to see what it meant to me. And then it's going to have to go in the trash bin, right? That's a good way to think about it.

18:33And so I just think of how can we, and I do this with a lot of the stuff I own, where if I haven't physically touched it in six months, it's on that list, that list of like, okay, do we want to get rid of it? Like if it's sitting in a drawer and I haven't touched it, like there's a reason, right? Yes. Yeah, I mean, my garage, I wrote this thing for Daily Dad the other day where I was talking about how the garage is this graveyard of like strollers you don't use anymore, cribs, the nursing, you just accumulate this stuff that ordinarily would be stuff, right? It'd be like, I don't care about this chair that I had in my house eight years ago that I don't want anymore.

19:11But because you spent a lot of 2 a.m. feedings in said chair, it means something to you, but it doesn't actually mean anything to you. The thing that means something to you, you have. you're just projecting it onto this physical object and then I'm experiencing it now because my parents are older and they just mail me the crap that they've kept for 30 years and now I'm like, what am I going to do with this wooden high chair that I in good conscience can't even put my kid in because it's not safe and then now it's just supposed to stay in my attic for 30 years to be their problem I'm sure you've heard of this charged objects where there's emotion associated with something.

19:56And the reason why we buy, I mean, your Iron Maiden shirt's a charged object. There's something about that band that you love and you're like, I have to have this shirt. This is badass. I mean, this one isn't, but I have some from high school. So I'm like 20 years into these shirts. And I, it's not just that I can't get rid of them. I also don't want to wear them because they mean something to me. So it's literally just dead weight in my life. Right. And well, there's, it's also, it's fascinating because it's, it ties into purchasing decisions as well for new objects. Yes. Like, I mean, anything from the Jordans that you're wearing from that history to like, when I went, went into this glasses store, I was in London.

20:39And then when I bought these glasses, they had a picture up of not of these frames, but Johnny Ive wearing their glasses. That's a big one for me. For you, that's, yeah. For me, that's like tech god, right? I'm just like, well, I mean, I have to have those glasses, you know? And so it's like, there's so many things that we fall victim to. And I'm not fall victim to, but we just like buy into the marketing. Like I'm not the kind of person that buys the TV marketed stuff. But when I see something like that, I'm like, oh shit, I'm in, right? Totally. No, there's a story about Epictetus. So he has this little shrine in his house, like to a Roman god.

21:14It has this little lamp in it that you would light this oil and it would burn. And so he gets woken up in the middle of the night one night and he hears someone in his house and he rushes down and a thief is broken into the house and he steals this like gold lamp. And so Epictetus is kind of upset, but then he's upset with himself that as his philosopher, he's upset that this thing was stolen. And he says, you know what? You can only lose what you have. Tomorrow I'm going to go buy a clay lamp. Like he goes and he buys a cheaper lamp. And it's supposed to be this philosophical lesson that, you know, you don't get attached to physical items.

21:47You know, the cup is already broken as the Zen saying goes. Like you lose it as soon as you get it. And so that's the lesson. But then we get this sort of historical footnote, which is that after Epictetus died, this fan paid a bunch of money for the clay lamp. Like he liked the teachings and then that became a charged object for him. And in the one sense, it's like keeping the philosophical memory alive. So maybe it's part of his philosophical practice, but it's actually proof that he missed the lesson, which I think about all the time. Right, exactly. And if that person gets that lamp stolen, then he's going to be upset.

22:22Yeah, totally. The cycle repeats, right? Yeah, well, and I think about, it's also kind of humbling. Like I just bought, for my podcast studio, I have Joan Didion's dining table, like, which I bought at this estate auction, which I was really excited. I'm a huge fan. I needed to buy like a nice table anyway. And so it worked out. But there was also something to me in it, Like sort of a lesson about how meaningless your charged items actually are, which is like, here you have this world famous, like beloved icon. And then she doesn't have any kids because of some tragedies, which she writes about that survive her.

23:00And then her family's like, let's just get rid of all this shit. Do you know what I mean? Like, like that's the thing is that either you put it in the dumpster or someone's going to put it in the dumpster for you. Yeah. Yeah. And well, it's crazy how, I'm curious to get your take on this, but like so often when we buy things that we think are going to give us long-term joy that are charged end up being a week long adventure where you'll buy something and you'll be like, oh my gosh, this is the coolest, you know, insert new sports car or whatever it may be. and then one week later you're like, oh, that was just like the excitement around buying it was actually the thrill.

23:38Yes. And now I'm just a douchebag because I'm driving this sports car. Like, how do you? Well, I experienced a version of that too or I have in my career, which is like, okay, some accomplishment happens. Like maybe for you it would be like, you know those like deal mementos? Right, in VC offices. Yes, exactly. In writing, it's more like you hit a bestseller list or you're profiled in some big magazine or your publisher. So the first time you do it, you're like, oh, I should frame that. And then you frame it. And then if you keep going up in your trajectory, well, now hitting number 17 on the bestseller list is not as significant as the number one spot, but you already framed one and now you're framing the other.

24:21And now you just have all these frames. And so my wife was finally like, we can't have all this shit about you in our house. Right. And I'm like, and I'm like, I totally agree, but I already spent this money framing it or somebody spent this money framing as a gift. And it's obviously worthless to literally anyone else. Cause who wants like a framed accomplishment that's not theirs. Yeah. And then what are you supposed to, like, I imagine in Bruce Springsteen's house, there is a room filled with like gold and platinum record plaques that he doesn't know what to do with. And it's also kind of the same thing, which is like, it's a charged object, but then also a reminder of the ephemerality of the charged accomplishment.

25:04Because it was cool when it happened. You were eagerly waiting the news. Then it happened and you were excited. And then you celebrated by commemorating it or memorializing it. And now it's a dusty thing leaning against the back wall of a closet. And it's also a reminder that you are no longer that age. you are no longer that. It's a long time ago. A long time ago. That thing may have never returned again. You could have been a one-hit wonder. Maybe you'll never hit the bestseller list again. But you'll have impact in other ways. They're more tangible, more meaningful. I remember when I hit number one for the first time, I got that framed and I was very proud.

25:40But then literally the next week, Donald Trump Jr. took the number one spot from me and then it was revealed that he also had paid for it. You know, like he had bought it. And then so it was this kind of thing where it was like, first off, like for the second, I'm like, I did it. And then it's like, literally any idiot could do it. And then literally, it's also corrupt and meaningless. And you're just like, there's kind of a, there's this kind of stoic Zen thing of like, you think this is so cool. Let me show you who else has done this. Let me run down the list of how forgettable and ephemeral all those things are.

26:18and maybe you're not as special as you think you are in that moment. I'm curious, you've mentioned Zen several times. Yeah. How much overlap do you think there is with Zen and Stoicism? I think there's a ton. And I don't, it's almost so much that it's suspicious. Like either the Zen-Stoic overlap is like an instance of like convergent evolution, like where different species evolve very similar things like birds and bats both fly very differently and not really from a common ancestor. Or there's some common thread or like cross-pollination that's underexplored. But I think at the end of the day, they're honing in on the same sort of timeless truths about what it means to be a person.

27:15Has there ever been any, you know, in Zen they talk about these satori moments, these moments of enlightenment, you know, which I very much believe exist. Has there ever been anything like that in stoicism where people have kind of more or less had something flip where they're operating at a higher level of consciousness? I'm sure there are, although I have found in my own life that epiphanies are overrated, if not totally made up. Like, I find that if I actually went back, like, if you were to actually explore a thing that you now think of as this light bulb moment, if you actually explored it, like it took longer than that, or there was a bunch of things.

27:58Like, I talked about this one the other day, but I had this sort of, I had this memory of, like, breaking through on something and then, like, quitting my job and deciding to go down this writing path. and like I went back and I reread that book not that long ago. And like I found like the notes that I, like I found the epiphany, but then I looked on Amazon to see when I actually bought the book and the dates were like five years apart. Like, so that thing hit me and then it sat incubating and growing for much longer than when I tell the story. It's like that thing, you know, flipped a switch in me.

28:36Like it didn't, it didn't. And so I actually think that's one dangerous thing, like when you read memoirs or bios or people tell you about like their lives, is they're often like compressing things or conflating things and they're making it seem much clearer in retrospect than it actually was. Yes, that makes a ton of sense. Because oftentimes when you read, like even for me, you know, like if you read, say, one of the most famous Zen books, like Zen Mind, Beginner's Mind. And if you read that years apart, as I have now over the course of a decade, you just have a much deeper understanding every time you read it.

29:15When you have that time for your subconscious to process the information paired with a proper practice of sitting. Yeah, I think it's also just got to like sit there and your mind just has to work on it. And so even those, yeah, those like Satori moments, how much of those were the fact that they've been meditating on that problem for nine years? Yeah. And then the moment where it happens is obviously significant. Right. But like, is that moment actually like, is that what moved the needle? Or was the heavy lifting done seven and a half years ago in one hour of thinking, but it didn't have the other pieces?

29:57Yeah, it's interesting. There's a very interesting Zen story about someone, a young student who was into Zen, had a boyfriend that was actually really into Zen. And the boyfriend convinced the girlfriend to move to Japan and study proper Zen, like go to actual monastery and give it your all, which is a couple sits a day along with long seven day plus sits a few times a year, right? And she was kind of dragged into it, really wasn't into it that much. He was all about it, had read every Zen text, was super into it. She was a professional pianist who had just the skill and concentration in that training.

30:41And she had a massive Popsatori moment like three years into training, which is just like unheard of. That's typically like a 10, 15, 20 year adventure to get there, right? And he goes to the master like, how is this possible? And the only thing they can really figure out from this whole, like just interviewing her and studying her case, is that she just had this insane concentration power from years of studying this similar discipline. And it applied to the study of in-practice of meditation in a way that created the ripe conditions for this thing to happen. I do like that Zen expression, like when the student is ready, the teacher appears, which I think is also like the epiphany was probably there all along or the the all the ingredients were there, but it needed some moment for it to come together.

31:36And so, like, and I mean, I think this is probably also true from the people I've talked to about psychedelics. Like, there's never, they're never passing along some truly groundbreaking, like, never thought of before insight. It's just, it clicked for them for the first time on a profoundly deep level, whereas before it was surface or something different.

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34:24What's your, given your background with ego, what's your take on psychedelics as applied to ego and just have you seen are you a fan I'm not a fan I'm not a fan either I'm a fan of them being used in the right context meaning for people that have either severe depression that can be treated post war trauma there are several things where I look at the data the published data and I look and say this sounds promising I'm not a fan of like recreational, well, don't get me wrong. If microdose something for a fun weekend, watch a concert, whatever. But you know what I mean? Like this idea that we're the weekend warrior and we go out and then it turns out 20 years later, your brain's just fried and there's not really any insight.

35:12Well, especially I'm also, I make big allowances for people who have already tried all the other things and it hasn't worked. You know, like if you're already on, if your doctor's already prescribing you a bunch of very serious medications, which also have side effects. I think it's a different risk calculation to mess with your brain chemistry with these other things. Yes. But actually, I don't know if I should say this, but Tom Wolfe's estate reached out and they asked if I would write a new intro to the electric Kool-Aid acid test. Have you read that book? No, I haven't. So in like the 60s, Tom Wolfe wrote this book about Timothy Leary and like his band of merry pranksters or whatever.

35:52And I was rereading it because they asked me And it was like amazing how utterly similar all of the types and the fascination and the certainty that they've discovered this thing that will solve all of the world's problems. And then just like how comical and delusional and dangerous it turns out to be like in retrospect, right? And yeah, I'm just very leery of fucking with brain chemistry. And I know way too many people who it's starting to look like they reached a path, a point of no return. Yes. And I think it says something about where we are as a society that we call like popping a pill or drinking some potion.

36:42And we call that doing the work, not like 20 years of therapy or reading all these books or like long hikes. And, you know, like doing the work is the thing that's supposed to do it all for you. Right. I'm in the same boat. Like doing the work is not spending a few hours in a weekend taking a substance. Like it's sitting for me, it's sitting on a mat for the next, you know, 30 years. Yeah. Right. And they all want to tell you how transformative it is and how many times they've done it. Right. And there's something about the obvious contradiction in that that seems to escape them that shows me it's clearly not that transformative.

37:23That's what I worry. I've got a few friends. I'm sure we're in the exact same boat where they've made the trip to Peru or wherever. And you're like, oh, how many? You sound like you're doing great. Like how many, and they're like, oh, this is my like 73rd time. And you're just like, holy shit. Like you kind of like, you would hope that you got it. Okay. Like, you know, wash your hands. Like I'm done. Like I got my realization, but you got to keep going back, you know? Well, and not only that, I am the overlap or the descent into other dark areas seems to be, you know, uh, quite, uh, there's some, there's some alarming trends there.

38:01Like, then they're posting, like, COVID nonsense or vaccine nonsense. Or then they're announcing how they're opening up their marriage. You know, it's like, there's something about just, I think, to me, the stoic is just sort of, this is reality. This is how humans do things. There's enough to focus on without, like, kicking out all the legs of the stool upon which civilization stands. You know what I mean? Oh, for sure. I do applaud some of these. You know what I really liked is, sadly, the late Tony Hsieh, who ran Zappos, he really tried this holacracy approach inside of his company where it was a level playing field for everyone, really pushing the boundaries.

38:46He had a great book called Delivering Happiness. Do you remember that book? He tried like 50 different things. I would say that he would even have admitted this because he was a good buddy of mine back in the day, that probably half of them worked and were durable. But you got to, and I guess it's different than open marriages and other things that are a little bit more high stakes. But I love people that do push. No, innovation depends on people who are willing to experiment and take risks and do crazy things. It's just, I think what can, actually this is an ego thing, right? So inherent in any creative venture or entrepreneurial venture or cultural breakthrough is that everyone tells you it's a terrible idea while you're doing it, right?

39:36And then you end up being right.

39:41What do you learn from that? That that was the one in a hundred times that you take this huge risk and you turn out to be right? Or do you take from that nobody knows anything and I'm a genius, right? And so I think one of the reasons you see certain folks sort of descend into megalomania or just mania period or just all sorts of things is that they've sort of taken the wrong lesson from the freak instance of their success. They drank their own Kool-Aid basically. Yeah, exactly. And I think with Tony, it got very dark at the end. And that was probably a variety of factors. but the sense of like, don't listen to people who are telling you that what you're doing is crazy is one of the worst things that can happen to a person.

40:27And it's much easier than you think it is to happen to you. Well, especially high net worth people. Yes. Because you have these people that are around you that want to take from you. And it's funny, after Tony had passed away, all these articles came about how a lot of these people were on payroll. And of course they're going to say - Didn't Jewel write in this letter? Did you see that? Yes, I did see that. Jewel tried to talk him out of all this. And that's going to be, like, someone taking the time to write you that letter is going to be the vast minority of people in your life. Because it's just not, how many people are going to tell Elon Musk anything right now?

41:05Well, you saw his text messages that came out. Did you see that? No. So there was something, someone was served, and they had a whole slew of his text messages that came out. And it was essentially like 99.9 % of people just kissing his ass on any and every decision he made. No one gave him the real talk anymore. Right. Because the world's richest man. Sure. And so that just goes away. Yes. And that actually is, I think, the danger of some of the social media platforms. It's good for the platform to get you to spout off. And they encourage that sense of like, the thing I've thought about for eight seconds, that's a hot take that the world needs to hear.

41:42Right. When in reality, almost anything worth hearing is considered and contemplated and bounced off people in private first. And so obviously it's great for the platform to get the immediacy and the authenticity and the unfilteredness. But that's probably bad for you as a person to cultivate. And I think this is not just affected like rich, powerful people. I think it's broken the brains of the media also. Like, think about for a hundred years, the reporter has to synthesize all this information into a long form, like 1 ,000, 2 ,000 word, like evenly sourced, edited piece of information that explains what's happening in the world.

42:28And that's a really good muscle. That's a really good medium to form your brain over if you want to be like a smart, wise person. Then you take those people and you go, okay, of course you still have to do that. But also 20 to 50 times a day in 180 or so, 140 to 280 characters or whatever, just spout off about everything you think, your most reactive opinions, and we'll reward you with a fire hose of attention if that's provocative. Right. And I'm not sure it's possible to have those two brains at the same time. Yeah. Yeah. This is why I think social media is so dangerous. It's like, it's evil.

43:10And it's interesting because how do you, how do you wrap your head? So when I scroll Instagram, I get your content and I always watch it. And I'm always like, this is great. Like, cause I know you're thoughtful about what you put into there and I, you take your time. And then I, because I watch your content, I get like 10 other people that are doing other quick hit content that are not so thoughtful. And then I get all the other poodles doing weird shit and all the other stuff that I like normally scroll to. Yeah. And I wonder like, as someone that's creating content on this platform, how do you, how do you, do you ever think about like, maybe I shouldn't be doing content on this platform because it's like encouraging them to see other things.

43:51Like it's, it's gotta be so, I rarely post anymore to like Instagram and I think it's because I just got sick of it. Like I, it's, it's a tension between where are the people and what are, what are the like languages they speak or the way they consume information. And then like what's healthy for you as a creator slash person. And then also like what is like conducive to the messaging and all that. So like I kind of think about it as like I write my books and then we find ways to translate those into the other mediums. But like I try to spend as little time as possible on those places. I definitely try to like see what people are saying about this stuff as little as possible.

44:37But yeah, it's like, are you being an elitist snob and going like, books are the only way that people learn or should learn? And then you're ignoring like the millions of people over here. And then also, are you rewiring your brain to think, not even people go, oh, one minute video, that's dumb. It's so much worse than that. It's like people stop watching the first five seconds. Right. And it's probably more like the first two seconds. And so there's some, like, that's a really wicked environment that makes you have to really get to the point, but then also can prevent you from making a point.

45:17You know what I mean? Yeah. It's a tension. I'm more concerned about the second thing you said there, which is, like, all the other people who have gone, like the Andrew Tates of the world who have gone, like, oh, the stoicism thing is popular, particularly with young men. How can I weaponize that or manipulate that to suck them into a much more nefarious world? Do you know what I mean? Like there's, like I can tell, like the stoic virtues which I have on my wrist here are courage, self-discipline, wisdom. People are all on board with that. And then the fourth one is justice. And I can tell anytime I dare to talk about what one's obligations are to other people or, you know, like what justice actually means, like what that obligates one to do.

46:06I can tell when people who have gotten on board for the other ideas, but are not on board with that fourth one, I can see that jarring shift. And so one of the things that can be really dangerous, you know, this term audience capture? No. So you see this like with Substacks or also on Twitter, it's like your audience wants a thing from you. And as long as you deliver that thing, you'll be rewarded with them liking it and sharing it and then more people like them finding it. But then if the algorithm is designed to do that, it punishes, as does the paying consumer, when you tell people what they don't want to hear or what they don't like.

46:52Right. And so you watch people become radicalized by their own success. Like, so somebody is a liberal who breaks out of the orthodoxy on one idea, right? It's very rare that they will continue to be

47:14as schizophrenic as that, right? Like, I was actually just reading about this. I'm reading this Lincoln book here, but Lincoln's famous speech about, He says a house divided against itself cannot stand. He wasn't saying that he thought the United States would split. He was saying it will become all of one or all of the other, right? And that's what audience capture does. So like if you say something that's controversial with this audience, but it lights up this audience over here, you slowly but surely, you can almost track it, that person becomes all that thing because that's what's bringing in new subscribers, bringing the social shares, like getting the media attention.

47:52And then that's how, you know, Glenn Greenwald goes from The Intercept to regularly appearing on Tucker Carlson. What happened to that guy? Is this what, like, you think Elon is happening to Elon a bit? A hundred percent. I think it's the general, you know, just perils of success and wealth and power. Yeah. But I think he is, you know, that term too online or very online. He is very online and the algorithm has morphed into his soul and it's not taking him in a great place. The one thing that I worry about with social media that is, we touched on it lightly, but it's a real concern is one of the things that dawned on me is that when we were kids, you would have these very amazing moments that would happen naturally in real life where somebody does something hilarious.

48:49or says something really funny or there's a sad moment or there's just like a... And then America's Funniest Home Videos came on TV and you were like, oh wow, I can watch these for 30 minutes straight. And it was like, but these were rare things. And then every other time was just a dull moment. Yeah, exactly. And now I like, after I took like a six month little sabbatical from Instagram and then I started getting back on it and I was flipping through it and my wife's like, what are you doing? and I was like laughing out loud for like 20 minutes straight. And I'm like, I'm just getting entertained like nonstop.

49:24Like I'm watching moments that are so special and so infrequent that now when I don't have them, it doesn't feel right. I feel a void because I'm getting all this happiness and excitement when I'm getting these very rare moments all packaged together. So I don't have Instagram on my phone. It's on my wife's phone. Like that's the only point. because sometimes I'll need to check messages or I want to see how something's doing. So it's on her phone. So I have to like ask permission, you know, which works great. Although she hates it because it's like, she's like, give my phone back. But like, sometimes she'll like, I like, she'll come and take it from me.

50:04And I'll be like, thank you. Because like, it's so, it's so bad. You know what I mean? It just, you just, I'm like, I'm not even enjoying this. Like I'm not liking any of this. I think Twitter is the worst of all the networks in the sense that I, sometimes I get stuff that's like good for me on Instagram. I'm never on Twitter. And then I'm like, I'm so glad I did that. Like, I just, I'm mad or I'm frustrated. I'm like, what is fucking happening? You know, Sam Harris shut down his Twitter account. Good for him. Yeah. Like, I haven't logged into our Twitter in probably three years. So I feel, I don't feel like I need to shut it down in the sense that like, it's, it's only existing for people who want to watch it and it doesn't like affect my quality of life in any way.

50:48But yeah, I mean, you watch, I mean, it's clearly, I think it's broken Jordan Peterson. I think it's broken a good chunk. Actually, I interviewed Sam Harris not that long ago, and I was like, what does it feel like to be the last member of the intellectual dark web who didn't turn out to be like a complete garbage person? Do you know what I mean? Yeah. Like, what happened, right? I think four or five years ago, whenever that began, these were these sort of heterodox, interesting, generally decent human beings. and then you look at it now, you look at the major issues of the last couple of years and they're like 100 % on the wrong side of all of them.

51:32And not just on the wrong side and they're like, I think this and they think this. It's just like, there's just a meanness to it. And I was going to ask you about that because I think it mirrors a little bit of the Silicon Valley thing where like, actually, I was going to show you this. So look at this. I was just thinking there was this moment then and for like, there was this kind of hopefulness and idealism and positivity. The web 2.0 first launched. Yeah, of all of what was coming out of Silicon Valley. And that is, I think both the media narrative about it has flipped, but I also don't think that's totally unjustified.

52:05There seems to be something that curdled in the same way that they say the 60s ended at that concert where the Rolling Stones had the Hells Angels as security and it went really bad. There's something about the Silicon Valley culture that seemed to go really sour or nasty. Yeah, I mean, I feel that for me, that moment was probably when we started introducing algorithms rather than just raw streaming feeds. Because everything, I mean, you remember Facebook back in the day, when the feed was invented, it was chronological order of content. And so there was no like reboosting things. You know, you couldn't kind of like resurface something back up.

52:54Like if you missed it, you missed it. And we only had so few friends on there that it wasn't like you'd miss anything. You just go back to where you catch up and you're like, okay, I'm all caught up now. And that's just not the case. And you weren't also following, it was a bidirectional relationship back then. So there was no following structure. Okay. So it was like you had to accept a friendship from someone else in order to see their content. And that friendship had to be, you know, so when Following came out, that's when Jack put Following out there, which was cool initially. Because at South by Southwest, we were like, hey, I'm at this bar.

53:30Like we were literally tweeting out like, hey, this is where I'm at. And then there'd be people that would show up like, hey, I'm a fan. I watched your podcast. But cool, I'm glad you're here too. You could have a, one could have a relationship with many. Right, exactly. And then there was an algorithm on top of that. Eventually that was no longer just this feed of stuff. You know, retweets came out, things like that. And then it was just like, once the celebrities joined and then the content machines joined and then the friends joined, it was just like, it was out of control. But none of us knew that was going to happen.

54:06We weren't building it like that. When I built social voting into this stuff, I'm like, okay, yeah, voting exists in real life. It should be on something with Digg. It should be here, and we'll put the best content on the front page. And then all of a sudden, the political folks, I remember this very, I mean, you'll see why I remember this so clearly, is it was during Obama's first campaign, and a lot of his content started making the front page of Digg. Because it was very popular content. And we had a lot of more left-leaning people than we did right-leaning people. and so um all of a sudden we started getting email death threats to me saying they were going to kill me for boosting for posting too much obama related content on the home page of dig yeah that would stick with the first and and so yeah and so then we had to report that to the fbi and then there was a very specific one where it's like i know you're going to this live podcast event it was in chicago yeah i'm coming and you're going to be i'm going to kill you at this event yeah and um That was the first time I had to have armed security with me at an event.

55:10And I was like, oh, social media is fucked. This is not going to end well because we started seeing that the political content was taking over and dominating a lot of our homepage. And then we tweaked our own algorithm, which was to say, make sure there's a mixture of promoted articles because we didn't want it just being all politics. Yeah, yeah, sure. Because politics can eat, just like if you're having this nice dinner party and you're talking about all these things and then someone's like, Trump, you're never leaving that discussion. It's there for the rest of the evening and somebody's going to be upset.

55:46And especially during an election cycle, which is what we were walking into. And so it was just like, that's the moment that I realized like, okay, these social platforms are just going to be, because you have the most charged, motivated individuals to get their agenda out there. And so they are going to try any and every way possible. And so, you know, we saw just a huge influx of fake accounts and just the ways in which people were hiring and building bot farms to try and game and get their content promoted. It was no longer about, hey, you know, Intel released a new processor upgrade. That cool, that's the top story of the day.

56:26Sure. Like it just went all to politics. And then some, you know, it was, and then it went to people's trying to promote their own blog stories. and it was just like, man, it was, we all of a sudden had to have what went from like a moderation team of two to like 10. And then it was just clear that we had to have higher, we hired like, you know, PhD computer scientists to build, you know, smarter math to try and catch some of these more sophisticated attacks. And, you know, that was, we were small potatoes. Like we were, well, we were big at the time. We were like 36 or so million people a month that were coming to the site, but that's nothing compared to what these sites are seeing today.

57:02Do you think that also mirrors just the larger image, the larger journey of like, it's any industry or scene, like, you know, the hero lives long enough to become the villain. Like, it just seems like the longer one is successful, dominant, you know, influential. It's just generally bad for a group of people. There seems to have just been like the whole scene kind of went south. Yeah. It felt that way. It felt like, I don't know, it just felt like it was clear that what we were doing at that point was, you were being judged by your VCs, by your investors, by time on site, unique visitors. And it was clear that attention would directly translate into revenue.

57:53And so it was like, who can hire the best computer scientists that would essentially just build us early machine learning models to find the best content. And so that meant before when it was just humans voting on things to make the front page, it was very simple. It was like X number of votes with this number of not fake accounts equals content on front page, went to let's crawl the actual article, let's parse it, let's understand the content. And some of that was good in that we could say, okay, I remember when Michael Jackson passed away, there was the initial surge of articles that came in.

58:33We needed to group those together and say, this is a package of articles that is meaningful, put it on the front page. And then there's the follow-up stories that happened just hours later. The doctors involved, it could have been an overdose, blah, blah. Another package of, so crawling the content and understanding and making sense of the content made a lot of sense from just how you package and present the information because you couldn't do it. There was so much content pouring in, like hundreds of thousands of articles being submitted a day. No human farm could do that in any quick way because it was all about breaking news.

59:07Who's the fastest to break it? So it was just a race to figure out how... And then that turned out being used in such horrible ways.

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1:01:01You do seem like though, like if I'm thinking about the person that's in that picture that there now. You're different, obviously, in that everyone changes, but you seem still like a regular person. Do you know what I mean? For someone who's had a lot of different success in a lot of different areas, you still seem pretty normal to me. I mean, that is a compliment. Is that something you've worked on? Yeah. I mean, I think that the most, well, there's a few things one um when i was 22 i declared bankruptcy because i didn't have um i had an operation that i didn't have insurance for and i had a huge amount of debt i was like oh crap i'm never gonna be able to pay this before dig yes before yeah and just before and uh my credit was ruined for seven years or whatever was on my record my car got repossessed all that stuff and i just realized that like at that point like you don't need a whole you just need good friends to be happy.

1:01:55And I had some great friends. And I was, you know, I was working at TechTV at the time and I had some great friends. And once you kind of like hit that point, you're like, okay, like everything else is gravy. And then good things started happening. I got very fortunate. And like, you know, both in terms of just the things I was building and also the investments I was making, like early investor on Twitter and some of these other things that blew up. And I made the same mistakes everyone else did. I went out and bought stupid, fancy cars and expensive watches and dumb things like that thinking i can get more joy out of these items and then to our earlier conversation a week goes by two weeks goes by and you realize oh there's no joy to be had here yeah and in the the wheelbarrow conversation the more stuff you have the more maintenance there is to those things you know you get a bigger the bigger house that you have the more things break it turns out right yeah and so it's like i i've had a hard time in that I'm one of those people that I don't know that I'm stressed until it's too late.

1:02:53Meaning that I can take stress on every single day and I can take people coming at me on Twitter or wherever else. And then all of a sudden I'll have this moment where I'll just feel insanely overwhelmed. Tons of anxiety, overwhelmed, blah, blah. And so the only thing I had to really turn to is really figuring out how do I not lose my shit here. And so that led me to serious meditation. And real work on yourself. And real work on myself. Therapy. You know, not really going into and doing the hard work there. And digging into why dad was a verbally abusive father, but a great, or sorry, husband, but a great father.

1:03:34Like, we all got our shit, right? You know, and digging into all that and really working through it. And then honestly, like reading books like yours. And I remember Ego is the Enemy was a huge one for me. And there was a few other ones like The Minimalist and some other ones where I got into them and I was like, okay, there's a different way to live life here and spending the time to do that. If I'm sort of plotting a villain story, it's like he's on the cover of Forbes. How old were you? That was Business Week. I was probably 24, 25. So you're on the cover of Business Week, you're like, the next big thing, you're controlling this website that has huge amounts of traffic.

1:04:14Then it basically goes away. Yeah. And then you invest in it. Like, I could see that being the seeds of, like, a much darker story, right? Like, that could have led to kind of a bottoming out or a lashing out. Like, I could see that not, that doesn't sound like, oh, and then he ended up, like, well-adjusted and happy and keeps doing all these other things and started all these other. I could see like, I've got to prove them all wrong. I've got to never be in this vulnerable position again. Yeah. Or like, I'll never be successful again. You know, like I could see a bunch of different non-positive ways to go out of that trajectory.

1:04:52Well, I got some great answers for this stuff. I mean, so, I mean, the one thing that I don't know how, maybe it was some of your content, who knows what the hell it was, but, or, you know, we're both buddies with Tim Ferriss. Maybe we was talking to Tim through some of this stuff. because we've known each other for a long time now. But one of the things that I realized is that one of the hardest things, when they always say the hardest things are, when they think of masculinity, they think of working out or putting on a tough face during hard times. And actually, that's the easiest thing to do is to put up a front, to put up a wall, to be like, I got this, I'm a man, I can handle this.

1:05:33the hardest thing is to be vulnerable. And so if you really want to do the hardest thing and be the strongest man you can be, it's to be the most vulnerable version of yourself. Because that is truly the hardest thing to do. And it turns out when you're vulnerable and you can actually break down in front of your therapist and have some emotional release, which is actually when you do this ayahuasca things, I've never done it, but people are crying their faces off forever. I actually did hide those mushrooms after my dad died. And I will say that was a very big release. I did it one time and was, you know, sobbing for like five hours straight.

1:06:13Sure. And, you know, you realize that that is just like, that to me is the path back to readjusting after big defeats, quote unquote defeats. And then the other thing that I think is really important is that I realized that at the end of the day, when I think about my little girls, you always think about your kids. What are they going to think of dad when they get older? I truly want them to say, he tried a bunch of crazy shit. Because we're all going to fail. As VCs, when we invest in companies, we expect probably approximately one in ten to succeed. Right. So if you're a real entrepreneur, you're going to fail nine times out of 10.

1:06:57And if you realize that just failure is just admitting that you've learned something new and you can truly pick out what it is that I learned that's new and roll that into your next thing. Yeah. And there is always something to pick out of the rubble. Yeah. Right. Then like, let's just have fun. We're all going to be dead in a few years. Like, seriously, like, sadly, we have had people close to us at this point in our lives that are now no longer with us. through a whole variety of things, either mental issues that cause them to take their own lives or cancer at this point. I've had several buddies with cancer.

1:07:30And it's like, dude, that is the end game. It's time to roll the dice over and over again and just have fun doing it. And don't you think, obviously, a failure or a public controversy or disappointment or whatever, that's one thing. But then also I think there's when you succeed. You made the investment. and it pays off in a huge way, or you create this thing and it's super popular. And then you're sort of standing at the top of this mountain, or you get to this place that you had so much hope for, or you put so much into thinking like, that will fix me, I'll feel good then. Dad will be proud of me then.

1:08:08I'll feel secure or comfortable then. And then you're just like, wait, I feel exactly the same or worse, because now I'm dealing with the hangover of those expectations. You know, how one reacts to that is more of a champagne problem, but it's still a definitive sort of pivotal moment in your life because you can go like in the social network, you know, what's really cool, a billion dollars. Like you can take the absolute wrong lesson, which is like, oh, I just don't have enough of it. Right. Like a drug addict. Like, oh, I just need to try a higher and higher dose to get back to whatever that feeling I thought I had or that I did have.

1:08:46how one reacts to success. If you can get to a place where you're like, this is cool, it's nice, but what I really enjoyed was the doing it. So I'm going to keep doing it, but I'm not going to fool myself with the delusion that more is going to finally do it for me. Yes. And I've purposely, and maybe this is a defensive mechanism, but I've purposely never allowed myself to feel those super highs. Oh, okay. So I don't know how, I'm not saying that out of some crazy Zen shit, Like I literally know that I remember when my, um, uh, I don't know if it was my dad or my mom, but I was on the Jimmy Fallon show.

1:09:22And after I got off his show, uh, you know, I got a call by one of them congratulating me or whatever. And it was just like one of those things where I'm just like, I'm not going to make this a big deal. Cause if I make this too, like, if I, if I get too excited about it, I know there's going to be a letdown on the other side. And so I got to just act like it's a normal thing and just move on and just go on to the next thing. And if I don't make a big deal out of it in my own head. And maybe this is something I still need to work through with my therapist, but so far it's worked for me. I get it.

1:09:50It's not celebrating it. It's like, yes, it was great, but let's not, you know, let's pop one bottle of champagne, not two. Like, you know what I mean? Like, let's not, let's not take ourselves too seriously. Because a lot of it's luck. Almost all of this is luck. It is important, I think, to celebrate the win or to feel it when you're having it. I, the way I address that problem is I try not to have particularly specific goals to begin with, right? This is a very Zen idea, which is like, you forget about the target. You know, you just focus on the release of the arrow or whatever. You know, when you're going like, what I'm winning is an exit of this amount or sales of this amount or getting on this show or, you know, this many consecutive weeks of X.

1:10:35And it's just the, I'm enjoying doing this. It lights me up doing it. And I hope it works. It would be better if it worked than if it didn't work. But I weirdly feel like the longer I've done it and the older I've gotten, the fewer goals I've had. And that has massively contributed, not just to my happiness, but also to my lack of disappointments. Yes, 100%. I'm in the same boat. Maybe you just did a much better job framing what I've been thinking about. I had a conversation with my Zen teacher just a couple days ago. and he said to me, relentless, and I'm paraphrasing here, because it was more or less this, relentless practice with no expectations.

1:11:18Yeah. Like that's the key to success in that practice. I remember I was talking to this NBA player and this is a pretty common thing. So it's not like he told me something like mind blowing wisdom, but it really hit me. He was like, you know, he's like, I just wish I had more fun when I was doing it. Right. Now I don't get to do it. And I was so hard on myself while I was doing it. And now, now I like, I regret that. And, and I remember I was in the middle of this book that was kind of like kicking my ass. And I was like, how many people get to do this? Right. How, when I started, if, if I thought that I would get to do it once, that would have been like more than enough.

1:11:52And here I am on, you know, book X or whatever, and I'm not having, I'm not enjoying it. And then it occurred to me, like, I could die before it comes out. Yeah. I could get canceled before it comes out. I could run out of ideas before it comes out. It could just not come out for any number of reasons. So if I'm not enjoying it as it's happening, what am I doing? I've now made it only worth doing if it comes out and worse, if it comes out and it does well. Right. Two things that are not up to me. And the essence of stoicism is some things are up to you, some things are not. You focus as much as you can on the things that are up to you.

1:12:31Right. Having fun while you're doing something is up to you. For sure. I mean, this is like, I think this is something probably my wife gets pissed at me about a lot because, you know, if she's having a bad day or something, I'll just be like, well, we have clean drinking water, you know, and I'll just say something like that. And she's like, that's not helping me right now, you know? And I'm just like, well, we do. Like, we live better than kings. They didn't have hot water either, you know? It's like. Do you think about that with your kids? I try to have like literally zero expectations for my kids.

1:13:03Like, I don't, I didn't really care when they started walking. I don't care if they can ride a bike or not. Like, I just like, I was like, it'll happen. You know what I mean? I'm trying to, I'm not being like a hippie, like just raise yourself, but I'm just trying to go like all this stuff about when stuff should or shouldn't happen. Right. Is made up. They're already born on basically third base, not by being alive now, by being in America. Right. Not even getting to like race, gender or my privilege. Just like they're fucking crushing it compared to 90 % of the world. So like, what do I need to add some sense of insufficiency or slowness or what?

1:13:43Like, I just, I just, I'm just trying to like, I'm not trying to win at my hobbies. Like we were saying earlier, I'm also trying to not win at having kids. Yeah. You know, I'm in the same boat. Yeah. I actually, I just like, I think about ways that I can watch and observe and empower when needed. meaning that like it my oldest is like she just builds like a mad person like everything she's constructing stuff and i'm always like well there should be some extra cardboard laying around because she can just like go build stuff right and my youngest um every time she walks in the house and she smells a little bit instant she'd be like dad is meditating and she'll like say that out loud and then she comes in and she sits on my seat oh wow and and then um she has a little lovey too yeah and so she puts a little love lovey in the little mood tray here and like and like And I never say like, you have to sit, you should practice, you should still your mind.

1:14:31It's none of that. It's just like someday, someday you'll be more curious and ask me a question of which I'll have just like a simple, you know, maybe you want to do this or try this. But never forcing, never forcing. Yeah, I kind of have it. I call it like dad energy. I kind of have an aversion to like dad energy that like sort of controlling, like, let me tell you how things are going to be. Let me tell you why you're not measuring up. Like just the, like, I saw this, I actually saw on Instagram, but like, it was like a good way to evaluate your childhood is like play the sound of the garage door opening.

1:15:04You know, like imagining you're at your house and the garage door is opening. Are you happy your parents are home? Right? Like, and for me, like that's a, it's a, it's a kind of feeling. It's not like a great feeling, right? It's like, I'm not doing what I'm supposed to be doing. So I'm not measuring up in some, it's a negative feeling. Right. And like, I have that feeling now towards people that give me, like, I can sense someone that makes me feel that way. And I try to just not make people feel that way. That's funny. Now that I think about that, like, I did have that feeling of like, what the hell am I, what should I have done between when dad was gone and when he got home, you know?

1:15:41And in retrospect, like, you think about the relationship you have with your parents when you're older. None of that shit mattered to them anymore. Right? Like, I think about this with like the car. Like what I was writing this, I was like, what happened to, what happened to the car that my parents were very worried we would spill anything in? Right. Like they don't have it anymore, obviously. It's probably in a cube somewhere, like all mashed up. Like that's now a fucking 30 year old car that's worth nothing. Right. And so, yes, like, obviously you pay money for something and you want to treat it well.

1:16:15There's a resale vote. But at the same time, eventually the resale value goes to zero. Right. And so, so many of the things that as a parent and as a person matter to you for some weird, instant, you know, emotional reaction don't matter. Like in our garage, when I walk in, there's this big, like there's all this crayons. Like my son just got in the garage one day and started scribbling with crayons. And there was this immediate reaction of like, don't do that, even though it's drywall in the garage of a house that I, you know, have no intention of selling. Like it's the house I want to have forever.

1:16:49Right. And so, and nobody sees it. And, and yet I had this immediate negative reaction. And, and the funny thing is now, ever since every time I walked by, I like it. It makes me smile. Right. So how can I get closer to having that reaction in the, in the moment? It's like, you're hungry. You want to eat in the backseat? What do I give a shit? So, but how do you, I'm with you in that I love this stuff. I let my kids like jump on the furniture. Yeah. when you have a partner that is like, don't jump on the furniture, that's nice furniture. And I'm like, well, it's like, yeah, I agree if they have their shoes on, but otherwise let's just go.

1:17:26Thankfully for me, I'm more stressed about it than like I'm, my wife, my wife is more naturally this way. And it's for me, it's something I have to work towards. I don't know why exactly. So it's, it's more like I'm, I have to consciously do it. But yeah, there, there, obviously there's some tension. And then where I get into it, where it's a little more complicated is like, for instance, like, what do I care if the stroller is, you know, covered in popsicles and, you know, it's all messed up. Like, I'm not going to resell it. I'll give it away. Someone else can clean it up later. It was not cheap, but like it was cheap to me.

1:18:05Right. Yeah. And, and at the, so trying to get that, that way, like Zen about it, but at the same time, not teach my kids that like, it should feel expensive to them. Do you know what I mean? Oh, for sure. The idea of not being attached to things, the cup is already broken, that's really important. At the same time, that's probably not a great attitude for a six-year-old to have because that is the seeds of entitlement and the world smells like fresh paint kind of a thing. Yeah. Well, the interesting thing about the cup is already broken is before it was broken, it was well cared for. Sure. Right.

1:18:44It should be well cared for. Yes. So the popsicles stains on the, that was not well caring. You weren't actually tending to that object and caring for it. Yeah. But it's also, it's like, hey, look, it's the summer. We're in a walk. Like, do I want you to be enjoying the popsicle or do I want you to be stressed about not messing up the stroller? And at the same time, do I also want to be not, I also don't want to be teaching you. We can just get a new stroller, right? Like my son cracked his iPad. And so I had to go like, I was trying to think about how you say this. Cause like, if I cracked my iPad, I would just buy a new one.

1:19:21Right. Or get it repaired. And I wouldn't, I'd be like, this is what money is for, whatever. Right. I don't want him to feel sad or bad or, you know, mad at himself about it. At the same time, he broke it cause he like was not taking care of it well. And so I had to say something like, Hey, look, like we'll get this fixed, but you have to understand that the money that we're going to spend fixing this is not going to be spent on something else you want. So I was trying to, it wasn't like we can't afford to fix this, but I was trying to explain that there is a finite amount of stuff. And he was like, can't you just get more money?

1:19:57And I was like, from where? And he was like, from your bookstore. And I was like, okay, now we have to have a whole different discussion about how money is earned. But the idea, it's this tension between, hey, like when I was a kid, I was just petrified of anything breaking ever, stuff that in retrospect doesn't matter at all. And I think if my parents were thinking back to it, they'd be like, why did we spend so much relationship capital preserving things that eventually went in the trash? Yeah. And at the same time, not cultivating an attitude of indifference or entitlement. Or wastefulness.

1:20:33Of wastefulness. this yeah even even it's like hey we can get a new stroller but we shouldn't have to get a new stroller and they're they're environmental there's an environmental impact to having three strollers instead of one right this is it's a it's a struggle yeah it's a struggle to figure this out because i'm i'm in the same boat like i'm the mine is is i don't even know if this is good podcast content but mine is like the the the um the dishes that say their dishwasher safe yes and i'm like oh this isn't good and the problem you know my wife's like no no you don't understand like they'll be ruined and like way quicker.

1:21:04And I'm like, it says dishwasher safe. Like they can go in, you know, and it's like these stupid little battles that you have. Yes. And you don't know, like, is it like, should I just wash the dishes to wash the dishes, which is the Zen thing to do? Yes. Right. And so just like in, it's, it's a very hard thing to do. Yeah. Are you preserving needlessly the dish or are you needlessly burning through the thing, which is also not good. There's probably, And then there's also like your time. Yes. So your time you could spend on other philanthropic endeavors. Sure. Save up those hours. Yeah. Put them into some other, I'm sure you could go on one speaking engagement.

1:21:45Yeah. And give a lot more away than washing those dishes, right? So it's like, how do you? Yeah, it's like, hey, this iPad is literally the cost of a human life, you know, in terms of malaria medication. Right. So like, let's try not to needlessly break things, but let's also not live in the way that I think a lot of people sort of get, depending on their upbringing, you sort of have this scarcity mindset when it comes to money or stuff. And yeah, now you're acting as if you can't just get a new dish if it's messed up. And now you're arguing with someone, you're yelling at someone about messing up a dish that again, you know, you'll never think about again.

1:22:30Have you seen that there's this old style of when dishes are broken in Japan where they use this like... Kintsugi? It's with the gold. Yeah, exactly. Have you done that before? I've never done that, but I love the concept. I just bought a kit to do it. Yeah, because we broke a really nice piece of pottery. Yeah. And you actually make this, it's from tree sap. And then also with gold mixed in, like gold flakes. And it makes these beautiful lines. And you can reconstruct a broken cup or a broken dish or something with this tree sap. And yeah, it's a way to slow down and actually practice and reconstruct something at the same time.

1:23:07Well, I like the idea that you're not only fixing it, but that it's literally more valuable. Yes. Because it now has gold in it. There's something about that. And it becomes this sort of artistic statement. and then it's a reminder of fragility, but also resilience. It's very, very beautiful. Yeah. The whole thing. I mean, that's the whole, I mean, I'm sure you study Wabi Sabi at the same time. I mean, it's so much more than just the one sentence that people give it in terms of like this idea that you can, the worn nature of things is actually valued and beautiful, you know? Yeah. Well, there's a Hemingway quote that I love.

1:23:41I think it's in A Farewell to Arms. He says, you know, life breaks everyone, but those it doesn't break, it kills. And then he says, but if you break, you can become stronger in the broken places. And so I think that goes to the point about vulnerability. There is this idea that the stoic is sort of invulnerable, never feels, never breaks down. And what I actually think that creates is a very fragile person because it's like the event just has to get bigger and bigger and bigger until eventually it breaks you or kills you. But if you can go like, hey, that hurt or I don't like that, or that triggered something in me, or I'm sad about that.

1:24:17Then you can process and deal. Then you can come back together and be stronger in those broken places. And I think this is true as a parent. This is true in relationships. Like you have to be able to admit error, to admit that you were going in the wrong direction, that you messed up, that something came over you. Even as a parent, just the idea of like, I could probably count on one hand the amount of times that my parents ever apologized for anything. And they were not infallible people. Right. Yeah. And, and so just the idea of like, Hey, like I messed up. I'm sorry. I shouldn't have done that.

1:24:51Here's why I did that. Here's why I'm working on not doing that. Here's why that doesn't say anything about you or how I feel about you. And if you can do that, then your relationship can get better. If you don't do that, you're just building up this, this, it's like, you're, you're just making it more and more likely that as soon as they can leave, they will leave. Yeah. Yeah. Which is what I did at 18. I was out the door. Yeah. Yeah. You're also saving them a lot of money on therapy later. Hopefully I'm sure they'll be in therapy about different things. Yeah, exactly. No, but there's, yeah, there's that thing like you only get 18 summers with your kids.

1:25:27And it's like, if you suck, you know, like some people, and that, that was actually eyeopening until you go away, you meet people, you have different relationships. You're like, wait, some people like, like their parents and spend time with them. Like, Like there's obviously families who do it for unhealthy reasons, but then they're like, wait, you guys all like spending time with each other and you like your cousins and you like communicate and you have this whole extended family. That was incredible. Yeah, it really is incredible when you see it working. I had bits and pieces of that, but never the whole thing.

1:25:59Yeah, and so like, yeah, the whole 18, obviously, yes, memento mori, you might die and it could go away. But like if you do it right and you get better in the places where you've messed up, like you could have many summers together. But yeah, it's interesting. Should we call it? Yeah, this has been great. It's been awesome. Any other last things? Oh, yes. Actually, this is fun. We should talk about this. I need your help selling a watch. Oh, interesting. This isn't just like, I'm not just imposing on you. You know who Peter Singer is? He's like the inventor of effective altruism. He wrote like Animal Liberation Now.

1:26:35So he's like one of the first animal rights people. And then he came up with this idea, partly based on the Stoics, which is he came up with this metaphor, which is like, okay, if you saw a child drowning and you had your fancy work clothes on, you would not like step over the child because you didn't want to get your work clothes dirty. You would save that child's life. And he says, it's not any different that a child is starving to death in Africa or whatever. And so he came up with this idea of like helping anyone anywhere is a fundamentally sort of philosophical obligation. He talks about expanding the circle, which is this stoic idea that there's these circles of concern.

1:27:11And then he came up with the idea of like, okay, so if you should help anyone anywhere, you should try to help the most people. You should try to look at the effectiveness of helping people. So obviously there are people who are dealing with emotional issues here in America and that matters. Like malaria nets are probably the biggest thing or something like that, right? The big one he contrasts is like, it costs$50 ,000 to train a seeing eye dog, which helps a blind person have a higher quality of life. But you could save a thousand people's lives with malaria nets. It's not that there's necessarily like you should pick one or the other, but the contrast of that needs to inform.

1:27:48So anyways, he's this great philosopher. Anyways, I had him on the podcast and he was telling me he just won this philosophical award and they gave him a Breitling watch as the prize. like he's like it's like i can't he's like i can't talk about effective altruism and then have a ten thousand dollar watch like it doesn't work so he's like what should i do with it he's like i was just gonna sell it was like i was just gonna sell it to a watch dealer and then donate the money and i was like you have to sell peter singer's breitling right and it'll sell for a lot more and it did it sold for like twenty thousand dollars or something but the cool thing was so i was the second bidder and the like the i was second in the auction and somebody else won it And then that person was like, I want to give it to the second person.

1:28:32He didn't want the watch. Yeah, you got it? I have the watch. But I think his expectation was like, I would do this. I would resell the watch. Why was that his thing? He wasn't just saying like, I paid for the watch. I don't want it. I think he was trying to say, now you, like, let's try to do this again, is what he was doing. So I now have this watch, which I am going to wear on stage for a talk. And then I want to sell and do the same thing over again. And then hopefully it creates a chain of things. That's amazing. Well, we've got to write an article on Hodinkee about this. Okay, so I'll send you a picture of the watch when I get it.

1:29:09Yeah, that sounds awesome. I was like, of all the people who could tell me how to resell an expensive watch, that's not worth so much as a watch, but worth more as a watch with a cool story behind it. Yeah, 100%. Yeah, let's get on Hodinkee. This is like a prime story. That's what I thought. Yeah. Have you seen, I think you should leave that TV show? No. Yes. I have seen it. It's like a million movies. There's a super funny one where he like, he goes to Starbucks and he's like, I want to pay for the order like of the person behind me. Yeah. And then, so they're like, oh, that's so nice. But the hustle is like, he gets in the car and he drives back around to pull behind them in the, in the drive-thru.

1:29:46So he can get his free. Yeah. He's like, I want 50 tacos. You know, he's like ordering. Yeah. That's awesome. So that show is great. It's so good. So anyways, that was my only other thing to talk to you about. Well, thanks for having me on. Yeah, thanks for coming on in your studio. Yeah, it's great. Perfectly. Awesome. Awesome.

1:30:14Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, That would mean so much to us and it would really help the show. We appreciate it. And I'll see you next episode.

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