The Daily Stoic - Kevin Rose On Staying Healthy With Entrepreneurship, Zen Buddhism, And Being Vulnerable

Episode Date: August 9, 2023

Ryan speaks with Kevin Rose about the pros and cons of his entrepreneurial drive, the calming effects of reducing the amount of stuff that you have, the overlap between Zen Buddhism and Stoicism, the dangers of social media, why being vulnerable is the hardest thing to do, and more.Kevin Rose is an entrepreneur, podcaster, and television host. Having co-founded the companies Revision3, Digg, Pownce, and Milk, and having been a venture partner at GV, Kevin’s work focuses on tracking and contributing to rising trends in the tech industry. As a host, he has worked on the G4 shows The Screen Savers, Unscrewed With Martin Sargen, and Diggnation, for which he also started a weekly podcast. He currently serves as the CEO of Proof and a partner of True Ventures. You can find Kevin’s work at his website kevinrose.com, and on Instagram @kevinrose and Twitter @kevinrose.✉️ Sign up for the Daily Stoic email: https://dailystoic.com/dailyemail🏛 Check out the Daily Stoic Store for Stoic inspired products, signed books, and more.📱 Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Welcome 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. Hey, 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. Like the building is sort of this conglomeration of buildings and I wasn't sure where the parking rush was, so I'm circling the building trying to find the parking. I can't see, I call my producer and one of them doesn't answer that I've got the other one and go, hey, did they say anything about where I'm supposed to park? And they couldn't find out. And then so

it's 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 realize, oh, I forgot my wallet. I'm sort of been on vacation. And I don't have my wallet to have been using it. And it's great. So 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 and all I'm thinking now is I'm late. 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 and this other part of the garage. And he's like, look, you can just Venmo me the money, all wipe you through and I don't have Venmo, so then I had my wife to do it. It's whole thing, but it was embarrassing, it was stupid, it was annoying. But normally, if I'm doing an interview and then I was trying to get home in time for the kids bedtime, it's not that the thing stresses me out, but it's like the other things that I'm trying to do, right? I've 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 handed it all super calmly. I didn't freak out. I just to remind you, look, the stakes here are pretty low, right? I'm not going to go to jail for not paying for parking. I know, I guess if I parked in the street parking, sometimes they tow an LA, which is happened to me and didn't want that to happen. But anyways, I feel like I handled it calmly, effectively. I just, it was like, there's obviously a solution. It all works through the solution. What's 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, it takes forever. But again, just handle the column. Don't make a 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. I show a picture of when we first met, which would have been in 2007. I was living in LA at the time. I was 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 to and got many, many tickets also, which I could not afford. Anyways, I've known Kevin a long time and he, 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 found a dig, pounce, milk. He'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 Hedinky. 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. It'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 talked about in the interview.

And he was in Austin a couple months ago for some crypto conference, and he was gonna come out to the painted porch and do it, but the timing didn't work. And he said, hey, I'm in L.A. now, when you are in L.A., just come and 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 and tried trying to practice stoicism on a sort of practical Monday level. And I feel 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 go go to KevinRose.com. You can listen to his somewhat intermittent off-and-off podcast with Tim Ferris, called The Random Show. And she'd check out a bunch of this stuff.

I'll link to it all in today's show notes. And I hope you enjoy this interview. Hi, I'm David Brown, the host of Wonder East Podcast Business Wars. And in our new season, two of the world's leading hotel brands, Hilton and Marriott, stare down family drama and financial disasters. Listen to business wars on Amazon music or wherever you get your podcasts. I started a place right when you were finishing it. Yeah, yeah, that was a fun place. It was awesome.

I'm kind of bummed-v sold it, but... But then there are all your people are here. Anyway, I think I'm not there. Yeah, I'd say like, what do you think about 30% of our staff is here, something like that? Yeah. It's a single largest concentration. Yeah.

Really, for sure. We got like 40 people or something like that. Which is crazy. For the NFT thing, we're all, but 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.

I do feel like, like if I was to describe you, I would say you're someone who gets like lit up by stuff. Like 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 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, like all that just like All that just, the excitement is so real. It just sweeps me up. You're like when falling 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. I think you're telling me some stoic lines. No, it's like like line is something I wasn't familiar with. No. Yeah, I mean, it's like, I've always had this mind that is 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 like an investment in like a company related to that, or every once in a while, like I just build something, especially if it's technology related, I'm gonna just jump in and build it. Are you able to be somewhat rational about it?

Like, is this viable or not? Do I wanna 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 gonna 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. That's what we look for when we do venture-related investments. It's kind of my venture training that's in me. We're not trying to build the next little local Taka Ria. We're going for something much, much larger. 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 gonna cost me, like, it's not gonna take up,

or it's not gonna cost me a lot of money, A, and it's not gonna be something that I need to, to tend over time. Like, for example, I launched a meditation app called Oak. Yeah, it's completely free. Yeah. And there was never a business model behind it. It was just that everyone was charging $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, you know, that app is still around. It has tens of thousands of great reviews. And it's just doing its thing. And no one is updated in like eight months if you look at the build release on Apple, you know, so those types of things, you know, I like to do. I've read a couple books that you know like Zen books that that needed to be put into audio form at the head and been put into audio

format. So I just like paid to have that done, like things of that nature. So like I have the money, why not spend it on something? It's like the philanthropic kind of side of like, how can I get back in that particular kind of way? So that type of stuff I'm into for sure. There's, 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. And for me, it's like, if there is, if it's just the day-to-day maintenance and growth,

meaning like, for example, I started in an interminute fasting app called Zero. 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 like content that you wanna 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 like that, the excitement of the early days of just like figuring out the UI UX challenges, figuring out how to track fast when you switch time zones because you flew to London. Like weird things like that, where you just had to think through the little edge cases, those are all gone. And so that's like where I get really excited, I get that like 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 have you had, is that a skill you've had to learn to the ability to hand stuff off? 100% delegate. Like you can be the fun, exciting idea person. 100%. 100%.

Yeah, that's, I'm now doing the multiple times. That's like, Kodinki as well, the kind of high end mechanical watch website. Yeah. You know, we've got 150 employees today. When I was there, where there was four or five of us, and you know, they had no mobile app. They 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 streaming 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 that it's not, you can't come home, wind the kids up, and then be like, well now I gotta go do my thing. Right? You know what I mean?

You have to think about, if you're someone who loves the metaphor I take from that is, or the analogy, is if you're someone who gets excited by starting stuff or having ideas, you have to realize like that becomes somebody else's problem after. And 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 best. Yeah, one of my good friends, another entrepreneur, Brin Mulligan told me, I need to build an app to remind myself not to build apps.

Yes. And that was like, basically he's advised to me. Yeah. It's very true though, like 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, like you've turned over enough cards, there's nothing here.

And there's no sense and just kind of trying to do another pivot or another iteration. Let'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 it would start at 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 and the ability to, you have to be able to empathize or yet call it and go, I thought this was gonna 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. With out-of-doubt, there's like, it can be the wheelbarrow that has a flat tire sitting on the backyard. Like at some point, I know I have to go figure out how to get that fixed, right?

Yeah, yeah, yeah. It's like, so it's anything I've reduced the stuff that I have by a aura of magnitude over the last five years. Yeah, although that takes its own discipline too, so my wife and I will be like, we have too much stuff or 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? And then you're like, oh, you like that one. But like when it, like 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, like, or just the sunk cost fallacy. It's really, really hard to overcome. There's a lot of ways, there's little things that I've done. A hard one for parents is the shit your kids make you. Yes, of course. You know what I mean? My daughter made me this amazing, multi-layered paper mishae

birthday cake for my birthday with paper candles and everything. And this is when she was four. And she's supposed to spend like three days. And I couldn't come over and it's like, Dad, don't look, don't look, I'm gonna go over here, you know. And I had this thing, it's massive. And she's 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 gotta 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 could just see what it meant to me. And then it's gonna have to go in the trash bin, right?

That's a good way to think about it. And so like, I just think of like, how can we, 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,

we want to get rid of it? Like if it's sitting in a drawer, I haven't touched it. Like there's a reason, right? Yes. Yeah, I mean my garage, I wrote this thing for daily, daily, 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, all, you just accumulate this stuff that ordinarily would be stuff, right? To be like, I don't care about this chair that I had in my house eight years ago that I don't care about this chair that I had in my house eight years ago that I don't want anymore. But because you spent a lot of 2am 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 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 like I like, 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 there.

Probably. It's called the, I'm sure you're for this charge objects, where there is emotion associated with something. And the reason why we buy, I mean, you're, I'm making sure it's a charge object. Yes. There's something about that band that you love and then you're like, I have to have this shirt. This is bad at this way.

I mean, this one isn't, but I have some from high school. So I'm like 20 years into these shirts. Right. 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, it's also, it's fascinating because 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 to this glasses store as a London, and when I bought these glasses, they had a picture up of not these frames, but Johnny I've wearing their glasses. So, it's a big one for me. For you, that's yeah. For me, that's like tech, 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. 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 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 this philosopher, he's upset. 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, you 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.

Right. Exactly. And if that person gets that lamp still and things gonna be upset, I'm just gonna 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 Didian's dining table, like which I bought at the Sustate auction, which I was really excited, I'm a huge fan.

And I needed to buy 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, and then her family's like, let's just get rid of all this shit.

Do you know what I mean? Like, that's the thing is that either you put it in the dumpster or someone's gonna put it in the dumpster for you. Yeah, and it will, it's crazy how, I'm curious to get your take on this, but so often when we buy things that we think are gonna 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, oh, new sports car, 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. Yes. 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, you some accomplishment happens. Like maybe for you, it would be like, you know, those like deal momentos. Right. Well, I see offices. Yeah. Exactly. In writing, it's more like, you hit a bestseller list or your profile in some big magazine or your publisher. Like, so like 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 like hitting number 17 on the bestseller list

is not as significant as the number one spot, but you already framed one and now you just have all these frames. And so like my wife was like finally like, we can't have all this shit about you, like in our house. Right. 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 because 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's 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, because 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 know, no longer a long time ago.

A long time ago. That thing, you may have never returned again. You could have been one hit wonder, maybe you'll never hit the best seller list again. But you'll have impact in other ways. They're more tangible, we're meaningful. I remember when I hit number one for the first time, I got that framed and I was very proud. But then literally the next week,

like 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 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 Stoke 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. And maybe you're not as special as you think you are in that moment.

I'm curious, you said, you've mentioned Zen several times. How much overlap do you think there is with Zen and Stoicism? I think there's a ton. It's almost so much that it's suspicious. Either the Zen Stoke overlap is an instance of convergent evolution where different species evolve very similar things.

Birds and bats both fly, but very differently and not really from a common ancestor or there's some common thread or like cross-pollination that's under explored, 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. Has there ever been any, you know, in Zan they talk about these satory 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 it 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, 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 like I talked about this one the other day, but I had this sort of I had this 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 flipped a switch in me. It didn't. And so I actually think that's one dangerous thing. When you read memoirs or bios or people tell you about their lives, is they're often 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 My 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, when you have that time for your subconscious to process the information, paired with a proper practice of sitting, you know.

Yeah, I think it's also just gotta like sit there and your mind just has to work on it. And so even though, yeah, those like satuary moments, how much of those were the fact that they've been meditating on that problem for nine years. And then where the moment where it happens is obviously significant. 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. Yeah, it's interesting. There was there's a very interesting

Zen story about someone a young student who was in to Zen had a boyfriend that was actually really in to Zen, and the boyfriend convinced the girlfriend to move to Japan and study proper Zen, like good actual monastery, and give it your all, which is a couple of sets a day along with, you know, long like seven day plus it's a few times a year, right? Yeah. 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. And she had a massive pop satory moment, like three years into training, which is just like unheard of. Like 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 impractic meditation in a way that created the right 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 all the ingredients were there but it needed some moment for it to come together and so like and I mean I think this is probably also true from the people I've talked to you about psychedelics like there's never they're never

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Listen to Sports Explains the World on the Wondery app or wherever you get your podcasts. You can listen to Sports Explains the World early and ad- free on Wondering Plus. What's your given your your background with with ego? Yeah. What's what's your take on psychedelics as applied to ego? And and just have you seen? Are you a fan? Like, what were you? I'm not a fan. I'm not a fan either of psychedelics. I'm a fan of them, where were you? I'm not a fan. I'm not a fan either. Of psychedelics? 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 micro does something for a fun weekend watch end 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. Well, 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 doctors are 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 Wolfs' state reached out and they asked if I would write a new intro to the electric cool-aid acid test. Have you read that book? No, I haven't. So in the 60s, Tom Wolf wrote this book about Timothy Leary and his band of Mary Pranks or whatever.

And I was rereading it because they asked me. And it was 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'm I I think it says something about where we are as a society that we've we call like popping a pill or drinking some potion.

We call that doing the work. Not like 20 years of therapy or reading all these books or long hikes and doing the work is the thing that's supposed to do it all for you. Right, and that. I'm in the same boat. Doing the work is not spending a few hours in a weekend taking a substance.

It's sitting for me, it's sitting on a mat for the next 30 years. Yeah, right. And they all want to tell you how transformative it is and how many times they've done it. And there's something about the obvious contradiction in that. That seems to escape them that shows me it's clearly not that transformative.

That's what I worry. I've got a few friends. I'm sure we're in the exact same boat where you're like, they've made the trip to Peru or wherever and you're like, oh, how many like you sound like you're doing great. Like how many, they're like, oh, this is my like 73rd time and you're just like, holy shit. Like you kind of like with hope that you got it. Okay, like, you know, wash your hands, like I'm done. Like I got my, you know, 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, quite, there's some, there's some alarming trends there. Then they're posting COVID nonsense or vaccine nonsense or then they're announcing how they're opening up their marriage. It's like, there's something about just, I think to me, this is still, because 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. Yeah, I mean, I do applaud some of these like, you know what I really liked is, you know, sadly, the late Tony Shay who ran Zappos. He really tried this holocracy approach inside of his company where it was like a level playing field for everyone, like really pushing the boundaries. He had a great book called Delivering Happiness. And do you remember that part?

Yeah, I know, I remember. And he tried like 50 different things. And you know, I would say that he would even have admitted this because he was a good buddy mine back on the day, that you know, probably half of more and we're durable, but like, you gotta, I guess it's different than like open marriages and other things, or a little bit more high stakes. But I love people that do push.

No, society depends on, 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 like, 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?

And then you end up being right, you know? What do you learn from that? That that was the one and 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 descend into Megalomania or just Mania period or just all sorts of things is that they sort of take in they've taken the wrong lesson from the freak instance of their success right? They drank their own Kool-Aid business. Yeah exactly and I think with Tony it got very dark at the end right and 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,

and 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 around you that want to take from you. It's funny after Tony had passed away. All these articles came about,

a lot of these people were on payroll. And of course, they're gonna say, didn't Jewel write in this letter? Did you see that? No, yes, I did see that. Yeah. Jewel tried to talk him out of all this. And that's gonna be like someone taking the time

to write you that letter is gonna be the vast minority of people in your life. Because it's just not how many people are gonna tell Elon Musk anything right now. Well, you saw his text messages that came out. No. 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 him. Any and every decision he made, no one gave him the real talk anymore. Right. Because these the worlds were just man. 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, right? 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 their 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.

And 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 a 180 or so, 140 to 280 characters or whatever, just spout off about everything you think your most reactive opinions and will 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. And it's interesting because how do you wrap your head? So when I scroll Instagram, I get your content. Yes. And I always watch it. And I was like, it's great.

Like, because I know you're thoughtful about what you put into there and I 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, I normally scroll to. And I wonder like, as someone that's creating content in this platform, 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 like it's it's got to be so I rarely post anymore to like Instagram. And I think it's because I just got sick of it. I got it. It's attention between where are the people. Yeah. And what are what are the people? And what are the languages they speak or the way they consume information? And then what's healthy for you as a creator, slash person, and then also what is conducive to the messaging and all that. I kind of think about it, it's 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. But yeah, it's like, are you being an elitist snob and going like, oh 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. You know what I mean? It's attention. I'm more concerned about the second thing you said there, which is like all the other people who have gone, like the Andertates 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 is, 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.

I 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 drawing shift. And so, one of the things that can be really dangerous, you know, this term audience capture? No. So, you see this term audience capture? No. So you see this like with substax 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, how, 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. And so you watch people become radicalized by their own success. Like so, somebody is a, somebody is a liberal who breaks out of the orthodoxy on one idea, right? It's very rare that they will continue to be as schizophrenic as that, right? Like, I was actually just reading about this.

I'm reading this link in 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 would 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 and then that's how Glenn Greenwald goes from the intercept to regularly appearing on Tucker Carlson. What happened to that guy? Is this what you think Elon is happening to Elon a bit? 100%. 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 was social media that is, we touched on it lightly, but it's a real concern is one of the things that the 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

or says something really funny or there's a sad moment or there's just like a, and then like America's Funnysome videos came on TV and you were like, oh wow, I can watch these like for 30 minutes straight, right? And it was like, but these were rare things. And then every other time, it could just a 30 minute to make. Yeah, exactly.

And every other time was, 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 non-stop. Like I'm watching moments that are so special and so infrequent that when 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 because sometimes I'll need to check messages or I want to see something's doing. So it's on her phone. So I have to like ask permission, you know? That's a big. Which works great. Although she hates it because it's like, she's like, you might fall back. Exactly. But like sometimes she'll like, I, like she'll come and take it from me, and I'll be like, thank you.

Because it's so bad. It's so bad. It's so bad. I'm not even enjoying this. Like I'm not liking any of this. I didn't Twitter is the worst of all the networks in the sense that I sometimes I get stuff that's good for me on Instagram.

I'm never on Twitter and then I'm like,'s like good for me on Instagram. I am never on Twitter, and then I'm like, I'm so glad I did that. Right. I'm just mad or I'm frustrated. I'm like, what is fucking happening? Sam Harris sat down as Twitter account. I'm good for him. Yeah. Like I even 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 only existing for people who want to watch it and it doesn't like affect my quality of life in any way. But yeah, I mean, you watch, I mean, it's clearly,

it's I think it's broken Jordan Peterson. I think it's broken. A good chunk, like actually I interviewed Sam Harris and 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?

Like, what happened, right? Like, 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. And 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 gonna 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 the, like, there was this kind of hopefulness and idealism and positive to put out for a sludge. Yeah, of all of like 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. There seems to be something that curdled

in the same way that like, you know, they say like the 60s ended at that concert where the Rolling Stones had the Hells Angels as security and like 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 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. Like if you missed it, you missed it. And we only had so few friends on there that it wasn't like you'd missed anything. You just go back to where you catch up and you'd be like, okay, I'm all cut up now.

Sure. 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. Yeah. 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. Like we were literally tweeting out like, Hey, this is where I'm at. And then there'd be people that should be like, I'm a fan of what's 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 this just as feed of stuff.

Retweets came out, things like that. And then it was just like, once this celebrity's 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 what was gonna happen. Right, we weren't building it like that. Like when I built social voting into this stuff,

I'm like, okay, yeah, voting exists in real life. It should be on something, you know what dig? It should be out 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 Dick. Because it was very popular content. And we had a lot of like more left leaning people than we did right, leaning people. And so all of a sudden, we started getting email death threats to me, saying they were gonna kill me. For posting too much Obama-related content on the homepage of DIG.

Yeah, that was stuck with the first. 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. I'm coming and we're gonna be, I'm gonna're going to this live podcast event. It was in Chicago. Yeah. I'm coming in and you're going to be, I'm going to kill you with this event. Yeah.

And that was the first time I had to have armed security with me at an event. Yeah. And I was like, oh, 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. And 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, that is, you're never leaving that discussion. It's there for the rest of the week. And somebody's gonna be upset.

And especially during an election cycle, in which we're walking into. And so it was just like, that's the moment that I realized like, okay, these social platforms are just gonna be, because you have the most charged, motivated individuals to get their agenda out there. And so they are gonna try any and every way possible.

And so, 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. 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 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 side, but that's nothing compared to what these sites are saying today Do you think that also mirrors just the larger image of the larger journey of like it's any industry or seeing like you know you the hero lives long enough to become the villain like it just seems like

The longer one is successful, dominant, influential. It's just generally bad for a group of people. There seems to have just been like the whole scene kind of went self. Yeah, it felt that way. It felt like, I don't know, it just felt like it was clear that like what we were doing at that point was, it was, you were being judged by your VCs,

by your investors, by time on site, unique visitors, and it was clear that attention would, which was directly translate into revenue. And 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, you know, 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.

It equals content on front page. Yeah. Went to let's crawl the actual article. Let's parse it. Let's understand the content. And some of that was good and that we could say, okay, I remember when Michael Jackson passed away, there was the initial surge of articles that came in. We 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 it, just how you package it, 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. And any like, quick way, because it was all about breaking news, like, who's the fastest to break it? So it was just a race to like figure out how, and then that turned out being used in such horrible ways, you know? You do seem like, though, like if I'm thinking about the person that's in that picture, there.

Now, you're different, obviously, and that everyone's, 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 like worked on? Yeah, I mean, I think that the most well, here's a few things one when I was 22 I declared bankruptcy because I didn't have

I had an operation that I didn't have, I had an operation that I didn't have insurance for, and I had a huge amount of debt. I was like, I'll crap. I'm never gonna be able to pay the loss. This is before dig? Yes, before dig. And just before.

And my credit was ruined for seven years, 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. And I had some great friends. And I was, you know, I was working at Tech TV at the to be happy. And I had some great friends. And I was, you know, I was working at Tech TV

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 to happen. 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 and 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.

And the wheelbarrow conversation, the more stuff you have, the more maintenance there is to those things, you get a bigger house that you have, the more things break, it turns out, right? And so it's like, I've had a hard time in that, I'm one of those people that I don't know that I'm stressed to tell us too late. And we're meaning that, like I can take stress

on every single day and I can take people, come at me on Twitter or wherever else. And then all of a sudden, I'll have like this moment where I'll just like feel insanely overwhelmed. Tons of anxiety, overwhelmed, blah, blah. And so the only thing I had to really turn to is like 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, 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. Like, we all got our shit, right? And digging into all that and really working through it. And then Like, we all got our shit, right? You know, and digitally and all that, and really working through it.

And then honestly, like reading books like yours, and I remember Ego's the enemy, it 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 spend in the time to do that, you know?

Okay, I can just, like if I'm sort of plotting like a villain story, it's like he's on four, the cover of Forbes, when he's how old are you? That was business week, that was, I was probably 24, 25, and that. 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, then it basically goes away. And then you invest in it, like I could see that being the seeds of like a much darker story, right? Like that, 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 a, I've got to prove them all wrong.

I've got a never be in this vulnerable position again or like, that never be successful again. I could see a bunch of different non-positive ways to go out of that trajectory. Well, I got some great answers for this stuff. Okay. 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 you know, we're both buddies with 10 fingers.

Maybe we was talking to 10 through some of this stuff, because we know each other for a long time now. But like, one of the things that I realize is that one of the hardest things, like when they always say like the hardest things are, you know, when they always say the hardest things are, you know, when they think of masculine, they think of like working out or being like, putting on a tough face during hard times. And actually, that's the easiest thing to do.

It's to put up a front, to put up a wall, to be like, oh, I got this, I'm a man, I can handle this. The hardest thing is to be vulnerable. Of course. 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. Yes. Right? 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 what what will they, when you do this, I wasca 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. Yeah. I did it one time and was, you know, sobbing for like five hours straight. Sure. 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 realize that at the end of the day, like when I think about my little girls, so you go and think about your kids, like what are they gonna think of dad when they get older? Like I truly want my little girls, so you go and think about your kids, like what are they gonna think of dad when they get older?

Like I truly want them to say, he tried a bunch of crazy shit. Because like we're all gonna fail at, you know, like as VCs, when we invest in companies, you know, we expect probably approximately one in 10 to succeed. So if you're a real entrepreneur, you're gonna fail nine times out of ten.

And 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 this new, and roll that into your next thing, and there is always something to pick out of the rubble. Then let's just have fun. We're all gonna be dead in a few years. Seriously, you can be like, sadly, we have had people close to us at this point in our lives that are now no longer with us,

you know, through a whole variety of things, are there mental issues that cause them to take their own lives or cancer at this point that has several buddies with cancer, like, you know, and it's like, dude, that is the end game. Like, it's time to like, roll the dice over and over again and just have fun doing it. And don't you think like, obviously a failure

or a public controversy or disappointment or whatever, that's one thing? But then also I think there's like, when you succeed, like that you made the investment, it pays off in a huge way, or you create this thing in a 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, I'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.

How one reacts to that is more of a champagne problem, but it's still a definitive pivotal moment in your life because you can go in the social network. You know what's really cool? A billion dollars. 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. You know, how 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 like more is gonna 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 just, I'm not saying that out of some like crazy Zen shit. Like I literally know that I remember when my, I don't know if it was my dad or my mom, but it was on Jimmy Fallon show. And after I got off the show, I got a call by one of them,

congratulations on me or whatever. And it was just like one of those things where I'm just like, I'm not gonna make this a big deal. Because if I make this too, if I get too excited about it, I know there's going to be a let down on the other side. And so I kind of 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 there's something I still need to work through with my therapist, but so far it's worked for me. I can. It'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 take ourselves too seriously. And it is a lot of this luck, almost all of this is luck. It is important, I think, to celebrate the winner 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 just focus on the release of the arrow or whatever. 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 this many consecutive weeks of X, and 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 like, I don't, I, I weirdly feel like the longer I've done it and the older I've gotten, the fewer goals I've had.

And that is massively contributed. Not just to my happiness, but also to my lack of distance with him. Yes, 100%. I'm in the same, but maybe you just did a much better job framing what I've been thinking about. Yeah, 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. Yeah. 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 mine, but it really hit me, he was like, 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. Now I don't get to do it. And I was so hard on myself while I was doing it. And now, like I regret that.

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? How, when I started, if I thought that I would get to do it once, that would have been like more than enough. And 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, I've now made it only worth doing if it comes out and worse, if it comes out and it does well, 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. Right. Having fun while you're doing something is up to you. For sure. I mean And this is like, I think this is something probably my wife gets pissed at me a lot

because if she's having a bad day or something, I'll just be like, well, we have clean drinking water. You know, I'm not sure. I'm just like, say something like that. She's like, that's not helping me right now. You know what 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 kids. Like I didn't really care when they started walking. I don't know 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 not, 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 is made up. They're already born on basically third base, by being alive now, by being in America, not even getting to like raise 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, like, I just, I'm just trying to like, I'm not trying to win in my hobbies, like we're saying earlier, I'm also trying to not win at having kids. Yeah, you know, I've been the same boat. Yeah, actually, I just like, I think about ways that I can watch and observe and empower when needed, meaning that like, 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, every time she walks in the house, she smells a little bit instant. She'd be like, yeah, it's meditating. And she'll like, say that out loud. And then she comes in and she sits on my seat. And then she has a little lovey too. And so she puts a little lovey

and a little moot tray here. And like, and I never say like, you have to sit, you should practice, you should still your mind. It'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 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 or if you, but never, never forcing, never forcing. Yeah, I kind of have, I call that energy, I kind

of have an inversion 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. You know, like, imagine you're at your house and the garage door is opening. Are you happy your parents are home?

Right? Like, yeah. And for me, like, that's a, it's a, it's a, right, it's not like a great feeling, right? It's like, I'm not doing what I'm supposed to be doing. Yeah, so I'm not measuring up in some way. It's a negative feeling, right? Yeah. 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. I now that I think about that, like, I did have that feeling of like, what the hell, what should I have done between when dad was gone and when he got home, you know? And in retrospect, like you think about the relationship you have with your parents

and your older, none of that should matter 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 the car that my parents were very worried we would spill anything? They don't have it anymore, obviously. Probably in a cube somewhere, all mashed up. That's now a fucking 30 year old car that's worth nothing.

And so, yes, obviously you pay money for something you want to treat it well. There's a resell up, but at the same time, eventually the resell 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 crap, like my son just got in the garage one day and sort of scribbling with crans. 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 wanna have forever. And so, and nobody sees it. And yet, I had this immediate negative reaction. And the funny thing is now, ever since every time I walk by, I like it, it makes me smile. So how can I get closer to having that reaction in the moment? It's like, you're hungry. You want to eat in the back seat?

What do I give a shit? So, but how do you, I'm with you. Yeah. And then I love this stuff. I let my kids like jump on the furniture. furniture. 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. Thankfully for me, I'm more stressed about them. Like I'm, you're the one that's, my wife, my wife is more naturally this way

and for me, it's something I have to work towards. I don't know why exactly. So it's more like, I have to consciously do it. But yeah, 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 covered in popsicles? And it's all messed up like, I'm not gonna resell it, I'll give it away. Someone else can clean it up later.

It was not cheap, but it was cheap to me, right? Yeah. And so trying to get that way, like Zen about it, but at the same time, not teach my kids that it should feel expensive to them. Because do you know what I mean? Like, oh for sure. Like the idea of like 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 you know, like 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. It 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 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 because like if I cracked my iPad I would just buy a new one right or get it repaired and I wouldn't

I'd be like this is what money is for or whatever. I don't want him to feel sad or bad or you know mad at himself about it and at the same time he broke it because he like was not taking care of it well. So I had to say something like, hey, look, 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. Right. But I was trying to explain that there is a finite amount of stuff. Right. And, you know, he was like, can't you just get more money? And I was like, from where? And he was like, from your bookstore.

And I was like, okay, now we have that 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 do 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 entitlements or wastefulness. Of wastefulness. Yeah, even it's like, hey, we can get a new stroller. But we shouldn't have to get a new stroller and there's an environmental impact to having three strollers instead of one.

Right. This is a struggle. It's a struggle to figure this out because I'm in the same boat. Like, mine is, I don't even know if this is good podcast content, but mine is like the dishes that say, they're dishwasher safe. Yes.

And I'm like, oh, these can go in. And my wife's like, no, no, you don't understand. Like they'll be ruined in like way quicker. And I'm like, it says dishwasher safe. Like they can go in. You know what? 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. And so just like, it's, it I just wash the dishes to wash the dishes, which is the zen thing to do? Yes. Right? And so just like, and it's, it's a very hard thing to do. Yeah, are you preserving needlessly the dish, right? Or are you needlessly burning through the thing, which is also not good?

There's probably, and then there's also like your time. Yeah. 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.

Yeah. And give a lot more away than washing those dishes, right? So it's like, how do you, how do you, yeah, it's like, hey, this iPad is literally the cost of a human life, you know, in the, like, 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, 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'll never think about again. Have you seen that there's this old style of when dishes are broken in Japan where they use this like. Consuri? It's with the gold.

Yeah. It's like have you done that before? I've never done that, but I love the concept. I just bought a kit to do it. Oh really? Yeah, because we broke a really nice piece of pottery. Yeah. And like you actually make this, it's from tree sap.

And then also with like gold mixed in, like gold flakes and it mixes beautiful lines. And you can reconstruct, you know, a broken cup or a broken dish or something with this tree sap. And it, yeah, it's, it's a way to slow down. And I actually practice and reconstruct something at the same time. Well, I like the idea that you're not only fixing it,

but that it's literally more valuable because it has gold in it. There's something about it. And it becomes this sort of artistic statement. And that's a reminder of fragility, but also resilience. It's very, very beautiful. 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. I 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, 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 a very fragile person because like, it's like the event just has to get bigger and bigger and bigger until eventually it breaks you or kills you. Yeah. 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, then you can

process and deal then you can come back together and be stronger in those broken places. 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 you know something came over you. that you messed up, that, you know, 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 then we're not infallible people, right? Yeah.

And so just the idea of like, hey, like, I messed up, I'm sorry, I shouldn't have done that. Here'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 just making it more and more likely that as soon as they can leave, they will leave. Yeah. Yeah. Which is what I did. Yeah, 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. And it's like, if you suck, yeah, like some people,

and that was actually eye opening until you go away, meet people, you have a different relationship. You're like, wait, some people like their parents and spend time with them, volumly. There's obviously families who do it for unhealthy reasons, but then they're like, wait, you guys are all like spending time with each other and you like like your cousins and you communicate

and you have this whole extended family. That was incredible. It really is incredible when you see it working. I had bits and pieces of that, but never the whole thing. Yeah, and so the whole 18, obviously, yes, momentum where you might die, and it could go away, but if you do it right, and you get better in the places where you've messed up, you could have many summers to get it.

But yeah, it's interesting. Should we call it? Yeah, and this has been great. It's been awesome. Yeah. But yeah, it's interesting. Should we call it? Yeah, I mean, this has been great. It's been awesome. Any other last thing? Oh, yes. Actually, this is fun.

We should talk about this. I need you to 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. So he's like the first animal rights people. And then he came up with this idea,

partly based on the Stokes, which 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 closed, or 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, right? And so he came up with this idea of like, like helping anyone anywhere is a fundamentally sort of philosophical

obligation and talks about expanding the circle, which is a stoic idea that there's these circles of concern. And 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.

Or, you know, like malaria and that's probably the biggest thing, or is there something like that, right? A big one you can trust is like, it's cost $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 and that's. It's not that there's necessarily, like you should pick one or the other, but the contrast of that needs to inform.

So anyway, he's just grateful us for it. Anyways, I had him on the podcast and he was telling me he just won this philosophical award and they gave him a bright-linked watch as the prize. Like he's like, I can't talk about effective altruism and then have a $10,000 watch. It doesn't work. So he's like, what should I do with it? He's like, I was just gonna sell,

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 bright-link, and it'll sell for a lot more. And it did. It sold for like $20,000 or something. But the cool thing was, so I was the second bitter and the like I was second in the auction

and somebody else wanted. And then that person was like, I want to give it to the second person. He didn't want the watch. Crazy. But you got it? I have the watch. So, but I think his expectation was like, I would do this. I would resell the watch. Why was that?

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 an aware like on stage for a talk, and then I want to sell and do the same thing over again. And then hopefully it creates like a chain of things. That's amazing. Well, we got to write an article about, on Houdinki about this.

Okay, so I'll send you a picture of the watch when I get it. That sounds like, 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 that. Yeah, 100%. Yeah.

Yeah, let's get on the hoodie and key. This is like a prime story. Okay. That's right. Yeah. Have you seen that? I think you should leave that TV show. No, yes, yes, yes, yes.

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 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-through. So he gets his free. Yeah, he's like 50 tacos. You know, he's like order.

Yeah, that's awesome. That's so great. It's so good. So anyways, that was that was my only other thing we talked about. Well, thanks for having me on. Yeah, thanks for having coming on in my studio. Yeah, it's great. Perfectly.

Awesome. Awesome. Awesome. Thanks 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. Hey, prime members.

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