The Daily Stoic - Not Seeking Wisdom DESTROYS Great Minds | Ryan Holiday & Billy Oppenheimer

Episode Date: October 25, 2025

What happens when brilliance goes unchecked? In today's episode, Ryan and his research assistant Billy Oppenheimer dig into the cautionary side of genius, from Elon Musk’s unraveling to why so many smart people end up making dumb decisions. They talk about how success can warp reality, why intelligence without wisdom becomes dangerous, and how even the brightest minds can lose their way when they stop listening, stop learning, and stop taking care of themselves.Billy Oppenheimer is Ryan Holiday’s research assistant and the writer behind the newsletter, Six at 6 on Sunday. To read more of his work, check out his website billyoppenheimer.com.📖 Wisdom Takes Work by Ryan Holiday is out NOW! Grab a copy here: https://store.dailystoic.com/pages/wisdom-takes-work🎥 Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us:  Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Look, ads are annoying. They are to be avoided, if at all possible. I understand as a content creator why they need to exist. That's why I don't begrudge them when they appear on the shows that I listen to. But again, as a person who has to pay a podcast producer and has to pay for equipment and for the studio and the building that the studio is in, it's a lot to keep something like The Daily Stoic going. So if you want to support a show, but not listen to ads. Well, we have partnered with Supercast to bring you a ad-free version of Daily Stoic.

We're calling it Daily Stoic Premium. And with Premium, you can listen to every episode of the Daily Stoic podcast, completely ad-free. No interruptions, just the ideas, just the messages, just the conversations you came here for. And you can also get early access to episodes before they're available to the public. And we're going to have a bunch of exclusive

bonus content and extended interviews in there just for Daily Stoic Premium members as well. If you want to remove distractions, go deeper into Stoicism and support the work we do here. Well, it takes less than a minute to sign up for Daily Stoic Premium, and we are offering a limited time discount of 20% off your first year. Just go to dailystoic.com slash premium to sign up right now or click the link in the show of descriptions to make those ads go away. welcome to the weekend edition of the daily stoic each weekday we bring you a meditation inspired by the ancient stoics something to help you live up to those four stoic virtues of courage justice temperance and wisdom and then here on the weekend we take a deeper dive into those same topics we interview

stoic philosophers we explore at length how these stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal, and most importantly, to prepare for what the week ahead may bring. Hey, it's Ryan. Welcome to another episode of the Daily Stoic podcast. I think that the path to mastery, to wisdom, to success, usually involves two things, and they kind of bookend each other, right? So it starts, as my career did, with what Robert Green

calls the apprenticeship phase. I began as an apprentice to Robert. That's how I learned how to write. That's how I learned the research. method that I build all my books around. Robert taught me that, and then I intern, and this is maybe not exactly the end of my career, but it's certainly a transition phase where then I taught that to my research assistant, Dillie Oppenheimer, who has become a great writer in his own right, and was the interviewer on this kind of Turn the Tables episode that we brought you part one of earlier in the week. He and I sat down and talked about the new book and how it got made and how we work together and all that stuff.

But I taught that to Billy, and he's now working on his first book, so there's that transition. But one of the chapters that I have in Wisdom Takes Work that I'm very proud of is about that, the sort of paying it forward. Actually, it's a theme in a couple of the books. It's a coaching tree chapter in right thing right now. I have a chapter in part one about finding your teacher, and then I have a chapter in part three about becoming a teacher. So let me actually bring you a little segment of that.

chapter because it's one of my favorites. Wisdom cares about progress, not itself. Each of us is only a vessel and not a permanent one. It is inevitable that we will all be replaced eventually. Knowledge is power, they say, but like power given to Antoninus, it has strings attached. We owe something to our teachers. We owe something to someone else now, too, to future generations. And that debt, as Stockdale described it, is teachership. But we are wrong to see this simply as charity, as some onerous moral obligation. We get something out of it.

The process is mutual, Seneca said, of mentorship, for men learn as they teach. In helping others, we are forced to examine our own thinking. to reflect on our experiences. We sit down and write, putting what was previously intuition into knowledge. And in writing this for someone else, we practice empathy and understanding. Feynman would actually say that if someone can't do this, if they can't clearly and simply explain what they know to someone else in simple terms, it's because they themselves don't fully understand what they think, they know.

We learn as we teach. Someone was our mentor. Who are we mentoring? We've had our board of directors, but whose board are we on now? That's what it's about. We've got to go back into the cave. We have to bring others out into the light with us.

And so, you know, obviously, as I was putting that together, I was thinking about Billy, I was thinking about my time with Robert Green. I'm thinking about the other researchers and employees that I've been lucky enough to work with. Some have gone on to do really awesome things, very proud of all of them. Billy's new book is coming out, which I'm excited about as well. I don't think it has a publicly stated title yet. He's got to finish it.

And Billy, if you are listening to this, although I doubt you are, I tend not to want to listen to things that are about me either. You've got to finish this book, man. Let's get it across the finish line. in any case you can check out billy's wonderful newsletter the six at six on sunday you can find that at billy oppenheimer dot com and as i was saying it's been one of my favorite things like as rewarding as any success i've had a bunch of different people have come in and gone is billy here can i meet billy or billy will come down when we do the walkthroughs to the store and they're like oh i get your newsletter i know who you are i just love that that's what it's all about that's the paying it forward

he's gotten better for his work with me, but I have gotten better working with him, not just his contributions, but in teaching and thinking about these things, that has been immensely instructive to me. And as I talk about in the Justice book, the third book in the Virtue series, Wisdom is Four, it's been immensely rewarding too. So this is part two of my conversation with Billy Oppenheimer talking about the new book, Wisdom Takes Work. It would mean so much to me if you could still order it this first week is where it's all at. Grab it on Audible. grab it as an e-book, grab the signed editions from The Painted Porch at dailysterisk.com slash wisdom, swing by the Painted Porch, swing by Barnes & Noble. I don't care where you get it. It just means a lot to me that you order it. And I can't wait for you to check out the book. Thanks to Billy for his work on the book. Thanks to you for supporting the other books in the Virtue series.

And I'll just get into this episode. Trying to think, like, how do we segue into part two of the book? Yeah. musk as a cautionary tale and that part just being like some of the anti-wisdom things to avoid he's the only one in the whole series there's some cautionary tales but he's the only like i tried to pick one really impressive person for part one part two part three of each book like i different than obstacle he goes i really do like a very big deep dive into characters said of florence nightingale and de gall taine queen elizabeth luke eric gondi gondi

Lincoln. But I think Elon Musk is the only one that is negative. I mean, the story starts very positive because he is a great man of history like the others. But then there is this turn, which is fascinating to me because we used to, I think he was one of the few people that everybody agreed about. Like, it is fascinating to me how he went from hero to villain so quickly and what happened. Yeah. Like when people go, Elon Musk, that people might go, what happened to that guy. That is itself interesting. So that's what that one's about. Yeah. And that was harder because it's also something that's, like, happening. And I, like, the Doge stuff happened after I finished. Yeah. So then I'd add some stuff back. But, like, that was a developing story. That was a

weird one, too. But it was also harder because, like, I felt like I had more of a hotter take when I wrote it. And then I feel like I've been subsequently vindicated by events. Yeah. In a way that, although satisfying intellectually might make some of the arguments feel less singular. But I think when I was writing them in 2023, they were a little fresher. Yeah. At some stage, you had, I don't know if concerns the right word, but just like a lot of people would maybe disagree with this take. Sure. Yeah.

But now. Yeah. You'll be there. If you don't, when you look at him and you see, if you're not like, whoa, that's something went sideways there. You're probably also brain fucked. Which, again, is not to say that he's not incredibly impressive. It isn't going to continually do to do impressive things.

I think that's what's actually the hard part about writing the chapter is that like every step of Elon Musk's career, what he's doing has seemed crazy. And betting against him is a very bad bet. So I'd have spent a lot of time trying to figure out if this moment is different and why it's different and what there is to learn from it. Yeah. What would you say is like the big lesson from him of what not to do? I mean, well, this is what happens when you don't take care of yourself, when you have no balance in your life, when you have no structure in your life. And a lot of it was informed by my experiences at American Apparel where I watched it. a different kind of genius become untethered. But to me, the most salient is like,

this is what happens when you go from reading Soviet Rocket Manuals to figure out the rocket business from scratch to getting all your information from social media. Yeah. Like there is people go, oh, podcasts are great, or, oh, you know, I've really curated social media or whatever. Like, this is what brain rot looks like. And this is what happens when you start to think you're a genius.

And you only hear from people who tell you what you want to hear. You become disconnected from reality extremely quickly. Yeah. Also, there's a really fascinating piece in The New Yorker that Jill Lepore wrote about his grandfather and father. His grandfather was like this sort of like quack doctor. who moved to South Africa because of its views on racial segregation, like before it was an apartheid state, like he went there to participate in it becoming an apartheid state and was a conspiracy theorist who, you know, was like anti-Semitic and sexist and racist and unhinged,

you know, and when you read that, suddenly the current Musk doesn't see. seem like an independent creation. It seems like the natural evolution of that lineage, which is, like, you read anything in that William F. Buckley's book I'm telling you about? Yeah. I'm like a third of the way. The book's incredible, is it not? It's really good.

Like, to be able to make a compelling biography of someone you would not give a shit about is like a very impressive feat. But if you read much about his father yet, is that, oh, Buckley's father isn't. the beginning? Maybe we're not very far. But you go, oh, you understand the father and then suddenly you can't separate. But the son did not independently come to all the ideas of the father. Yeah. The son heard them from the father, believed them, and then created intellectual justifications for, like, there's a scene where William F. Buckley's siblings go and burn a cross on one of their neighbor's lawns. And then you're like, oh, but he was a,

intellectually rigorous conservative. It's like, no, you were raised in a bigoted family that when desegregation happened, your father put his money into a segregationist newspaper. Your father dispatched you to tell your sister that she could not marry your best friend from college because he was Jewish. Like, you did not independently come to these. controversial ideas, but not from a place of bigotry if your bigot father had all the same views and you grew up with that person. So like the, you have to trace this stuff back and then you go, oh, okay, they're able to present it as this. Yeah. But when you have the larger context, there's a video of Francis Ford Coppola. Yeah. It's one of those where he's like walking through

all of his movies. And he has a line in there of the story of the son is always embedded in the father. Yeah, sure. And that's kind of like what he's exploring in a lot of his movies. Yeah, yeah, yeah. That's totally what it is. That's not to say that, like, it had to go this way. Yeah. But if it did go this way, it did not independently go this way, right?

Like, it's obviously rooted in the example and then whatever the predilections are in a person that may, you know, like the paranoid style did not strike twice like lightning. Like, you had a paranoid reactionary father, and you became just a more palatable and socially adept, paranoid style reactionary. That doesn't mean everything you said was bad. That doesn't mean you weren't smart. That doesn't mean you weren't a great writer. This doesn't mean you weren't a great political organizer. All those things are true. Just like Elon Musk is clearly not as extreme as his grandfather.

His father is a, it appears, a sex predator who had children with one of his stepchildren. Okay, so is Musk a pro-natalist because he did all this research about declining birth rates and blah, blah, blah, blah, and he really cares about the future of civilization? Or did he grow up in the house of a sexual predator and he picked up some weird, yeah. fetishes and stuff. And that's this furthering civilization is just the story to justify it. And again, this doesn't change the fact that he's a brilliant engineer or whatever. What I'm fascinated by is like if your great-grandfather or your grandfather was an anti-Semitic, racist, conspiracy theorist, quack physician.

might you, in the middle of a pandemic, go, if my instinct is, you know, to be anti-vaccine, anti-science, anti-public health, could these two things be related, you know, right? Or like, what it's fascinating about reading biographies is that, like, this stack of pages makes you understand the person better than they understand themselves in some ways. And how rare self-awareness is. Yeah. Not to say I have it, because if you think you do, you almost don't. I certainly don't.

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and he almost seems to like cut ties with anyone who's willing to like there's a That story. The Sam Harris thing? No. Oh, they made a bet during the pandemic for like quite a bit of money, but not obviously to Elon Musk about how COVID would go. And at some point, Sam Harris, like, followed up. And Musk was like, refused to acknowledge or pay up.

Yeah, it's pretty funny. Well, there's the story you tell of the, I don't, I can't remember if it's Tesla or somewhere else, but an employee kind of stands up to him. And it's like, I disagree with, like, what you, what you said, and he's fired immediately. He says, like, 1% of the population would fall for this thing that you just fell for. Like, this is, like, elite level stupidity here, you know? And Moss is like, fuck you, get the fuck out of it. You know, it fires him.

Yeah. And then he looks around the room and he's like, why isn't anyone else talking? You know, like, I have some experience with that because I, like, Dove at American Apparel would just fucking scream at people. And I think this new documentary, someone told me there's some scenes of it. but like I've seen the chilling effect that like that sort of feral like feral power slash anger issues like the what it does to people so yeah you add I mean there's this great letter that Twain writes to Vanderbilt and he goes like you think you're a genius but you're you're not understanding the way that your sense of yourself is the reflect off your 70 million. 70 million was like the largest fortune in the world at that time, which gives you a sense of how crazy society has got, like, 70 million.

I mean, Musk bought Twitter for 44 billion. Yeah. And it was like a rounding error to him. But just to be successful at any level is alienating and isolating. And the air gets thinner. But then if you eschew human interaction for an unhealthy amount of online mob dynamics, it is as toxic an environment as you can imagine building around yourself. I thought in the Ashley Vance book, I think it's in there. Maybe it's in the Walter Isaacson book.

But there's this scene where he fires, when he's only running SpaceX and Tesla, he fires his assistant and doesn't replace them. and that was like 15 years ago or 10 years ago. Now, of course, part of it might be pretends that he doesn't have anyone helping him. But the fact that there's not, he doesn't have a longtime person who is his, like when I was working on the Ravelling Book, he was like, call, and he said this name,

I won't say it because maybe it's private, but he's called this person. And it was like Michael Jordan's assistant of like 30 years. Yeah. You know, at that level, you need continuity and consistency. or else you become untethered, you know, and the idea that a person who's just on its face running an inhuman amount of companies and businesses at an inhuman pace with the stakes

as high as they are, that he would be fucking winging it. Yeah. And just like, what does it say that no one's stayed in his circle for a long time? Yeah. Like Rav had like relationships for 60 years. No, no, no, you need that. It's not healthy. And it's destabilized. Like, success is in and of itself destabilizing. So if you don't create stabilizers, you're going to fall off. Another cautionary tale in the book is SBF. Oh, yeah.

Although it's funny, that will probably get pardoned, and then that story won't seem as. I still think he's cautionary. Well, of course. No, no, I'm just saying. I'm just saying, like, you live in a time where that should be a universal cautionary tale. Just as Musk should be a universal cautionary tale. And instead, somehow these things have become partisan and almost like litmus tests. Like, you can't see the thing that should be obvious to everyone under any circumstances, even if you are predisposed to like that person. Yeah. But yeah.

And I thought people have criticized that Michael Lewis book as being positive. I think he, like, destroys him in that book. But he does it so artfully. that it doesn't feel like that's what he's doing. Because Michael Lewis is a seeming, I've never met him, but like a happy, well-adjusted person who seems to love celebrating unconventional characters. Yeah.

And, yeah, to me, that it is a withering picture. Yeah. Of him. That none of it, you wouldn't say that about any of his other books. Except for maybe the Jim Clark in the new, new thing, which is a great book that more people should have read, And it feels, it's probably going through a cycle where because tech has changed, there was a period where it didn't seem that impressive because it's like the founder of Netscape. But now that so much time has passed, it probably comes back around.

It's like reading about Rockefeller or something. But there's some scenes in the new, new thing where he's like playing a tuba alone in his room. And you're just like, oh, it's sad to be you, you know. But mostly, mostly Michael Lewis's portraits are very positive. Yeah, that's sad to be you line made me, there's something about like, I forget who said it, but it's like if you're so successful, why are you so miserable? Yeah, yeah, if you're so smart, why aren't you happy? I've heard it stuff like that.

Yeah, something like that. And Musk, like, there's just some really sad clips of him out there of just like, you wouldn't want to be. And he says that, you know, like, you wouldn't want to be me. I was at a party and I was talking to someone and they were asking me about the wisdom book and I was telling them about it. And then I slowly realized that they were, they were very connected to Musk.

I won't say how. I'll tell you later, how they were connected. But I put two and two together. And they were like, oh, I can't wait to read the book. And I was like, I'm not sure you do. Had you told them that. No, no, they were just, we were talking about wisdom generally, virtue and wisdom. They had like a philosophy degree.

They were like excited. Yeah. And then they were like, oh, I'll start with that one. And I was like, please don't. Or maybe that's like the person who needs to read it. Yeah. I'll, when I tell you who this person is, you'll get, I don't want to blow them up or embarrass them. But that was a weird part of that, right?

Because, like, they just announced, like, another million square feet. They're adding to the SpaceX offices, like, two miles from here. Yeah. Like, if you look at, like, if you get, like, an alert from Twitter or whatever over email and you look at the bottom, it's like, Twitter is headquartered in Bastrop, Dallas now. It's crazy. Right. Like, so you're saying, like, it would have been much easier to not include him. in the book in this way i just already know how many we we did a piece the other couple weeks ago

that you helped me with and um the amount of angry emails about it yes like it's i just already know and the people are all that what they're going to write is like how could you like didn't you understand this was going to piss someone like me off it's like i do i would just yeah like not to have to hear from me about it yeah you just keep it yourself but the part two like the watching your info diet not breaking your brain yes and as there's a good great story of SBF like with a journalist of like basically just never read a book being very skeptical of books he said that I would never he was like if you wrote a book you fucked up yeah it should have been an 800 word blog post the hubris of that the intellectual

conceit of that I mean he's obviously incredibly smart he can do things with numbers in a way that he could probably sit here and just our jaws would be on the floor like he'd probably be of those people that could, like, divide two credit card numbers in his head or something, right? Like, he's obviously a genius, but then you go, oh, layered on top of that genius was fundamental in curiosity, a fundamental ego, and a fundamental anti-social tendency that, in the unravelled the genius and, you know, brought you crashing back down to Earth. The idea that the thing that has been responsible for the progression of human wisdom over thousands of years, that these things are better expressed as an 800-word blog post.

So the audacity of that, and then it's also just perfectly encapsulates where we are as a society, the sort of death of expertise, the death of real knowledge. It is the Seneca story about, well, I just get someone to whisper into my ear. Yeah, yeah, yeah. And that's sufficient. And it's, it's both terrifying and tragic. Yeah. I thought what's interesting about that because that came with this interview. There's an interview, some guy who's writing for one of the VC companies, sort of like an in-house publication doing that interview. And like he has a little bit of an argument with him. This guy who's a professional writer.

Yeah. Goes, well, you know, he's so smart. He's probably smarter than me. Maybe he's on to something. Yes. And it's like, no, he's a fucking moron. Right. Like, that is one of the dumbest things that a person has ever said on the record to a journalist talk.

Just putting aside whether it's true or not, that's a dumb thing to say to a writer who is interviewing you and holds your fate in their hand. Like most writers would have, that would have changed the entire direction of the piece and it would have become a takedown. Like, I was just a reckless thing to do. Putting aside the fact that this is dumb and wrong, it's just a dumb thing to say. Like, know your audience, that's a dumb thing to say. Yeah. That's a dumb thing to say when you are spending hundreds of millions of dollars to buttress your public image to make you look like a super genius.

That's just a dumb, that's a thought you might have. And a lot of books are fuck-ups and do suck. But this is a dumb thing to say. Yeah. But I thought it was watching the mental gymnastics of this writer to justify an indictment of his own profession and life's work is also interesting. Well, yeah, and he like, the piece is like kind of glowing. Yeah, no, that's what I mean.

He's like, he knows more than me. He's such a genius. You're like, that should have been an emperor has no close moment. Yeah. But instead, it's the opposite, which is a big one. I talk a lot about cognitive dissonance in part two of the book. That is classic cognitive dissonance. I can either, like that guy's having to look at one of the richest people in the world

who just said something so profoundly stupid that it should make you question everything they think about everything. And instead of doing that, which is hard, also because he's being paid by the VC company to profile this person, instead of being like, five alarm fire, this is crazy. I don't know if this guy is what he thinks. He's like, no, no, no, no. He's more than I think. Like, he's actually, like, even smarter.

Like, and again, I've done that. It's easier to think that than to go, oh, fuck, now I have to be at cross purposes with this person. Yeah, I think the writer even has, like, a moment of questioning, like. There's a little back and forth. And then he's just like, no, no, no, I'm going to side with you. But no, like, questioning his own, like, oh, maybe like. Maybe I wasted my life. Yeah.

Yeah. It's pretty spectacular. How do you think about the difference between being wise and being really smart? Well, a lot of people are really smart and there's not that many wise people. Yeah. And I think the tricky part about being smart is that it makes you more susceptible to being really stupid. Yeah. Because you, like one of my friends who gave me some great notes on the must chapter, he said this thing I think about all the time.

He said, making a contrarian bet that turns out to be right can be a brain-destroying experience. And I think that's kind of one of the explanations for the radicalization of Silicon Valley in a very short amount of time is it's not good for your sense of self and your ability to continue to operate in the world to have gotten something very right while everyone else is telling you you're wrong. and then to have been proven right? Because then how do you go back to operating in the universe as a humble, regular person who's not right about everything, you know? Yeah, and it's just an entire population of people who have had that experience. And then you're on top of that. Money, fame, bubble, et cetera.

This is also what happens to Elon Musk, right? Like, it's hard to go, I was just right about this one thing. And then every other thing, I'm starting over from scratch on. I think about this, like, writing the obstacles away and it dramatically exceeding expectations and bringing, sort of creating this whole sort of resurgence of an ancient philosophy. That doesn't mean that every idea that I have is that. Yeah. In fact, statistically, it's much more likely that my next idea is not. that. And so the story you tell yourself, your relationship to reality, this is all a tenuous

stuff. Because making any kind, it's not even a contrarian bet, just making any kind of bet that pays off. It doesn't change. You're starting from scratch each time. And then each time you get more and more sort of emboldened by like, these people are wrong. Because I have proof that it takes a lot of discipline to start from first principles every time and to not go. These people, People are fucking wrong about everything. So if I think this, I'm right and they're wrong. That's, I think that is maybe the number one reason why smart people do stupid things. There's a section in the book where I just sort of list like all the dumb things that like really genius people fell for.

Yeah. And I think this is partly why like a lot of people that I knew that were sort of groundbreakers in these various things are now. have a lot of kind of fringe, either political or medical beliefs, is that it was hard for them to be right about, largely right about paleo. Like, the food pyramid is 100% wrong. Like, not what your diet should be. You should not be mostly eating grains and rice and breads and shit, right? It's not, that's not what we're meant to eat, and that's not. Now, the food pyramid was, you could argue that Those are the cheapest foods. And if you're trying to feed as many people as pot, like, there's some political logic

to it too. But the point is, they were totally right, you know? Does that mean you should only be eating, you know, like this carnivore diet? No, like that's probably not right either. But it's very hard to be, say, like, really right about paleo. And then everyone make fun of you and be like, oh, you're going to eat like a caveman, you idiot, you know, and get made fun of. And it turns out that, you know, they were largely right or their stuff helped a lot

of people or whatever, or they saw just at a personal level, they weighed this and they look like this, they made these changes, and now they weighed this, and they look like this. And then, you know, I think you're going to be more vulnerable to like, and maybe the vaccine shouldn't be trusted or whatever, right? Like when you've had a contrarian bet, it makes it, you start to see that everywhere. Yeah. And like, what else is wrong? Okay. If the food pyramid, you know, Have you read the Mark Marin memoir from, like, early in his career? Oh, the, yes. I forget the, he tells a story of, like, when he was in a period of that, like, just sort of questioning everything.

And he goes to meet a friend who was working in D.C. And he's like, what are you doing? Like, can you see this as all? And he's just, like, asking him about all these different conspiracies. And his friend is like, Mark, we're not that organized. And it was like, it broke him in a good way. of, like, it's just people going to work every day. Yeah, and that's not to say there aren't some conspiracies.

I mean, I wrote a book about one. That's not to say there aren't isn't some coordination. There aren't very popular beliefs that you should question. You know, anytime you're on the, Twain's thing, like anytime you're on the side of the majority, pause and reflect. Yeah. But there's a difference between pausing and reflecting and instinctively, intuitively being against it.

And that's like Peter Thiel, I remember said to me, He's like contrarianism. He's like, I don't like being called a contrarian because that means I just take what everyone believes and I put a minus in front of it. And I think when Peter's been right about stuff, it's because he was independently correct. But I do think you're watching, his trajectory isn't anything like Elon Musk. But there's certainly been, I think you can certainly trace a kind of, not an overconfidence, but a destabilizing effect that having been right about a lot of things. has had, and that can take you to some kooky places, especially when most of the people you engage with intellectually want something from you or are dependent on you in some way or

are afraid of you. And that's the root thing for Elon Musk. When was the last time Elon Musk had a conversation with someone, and he thought that person was smarter than him? Probably a very long time. Yeah. Whoa. And I guess that's a good question for everyone. When was the last time you had a conversation and you were aware in the moment that you were the student and they were the master?

And if that doesn't happen on a regular basis, I think it deforms your perception of reality. Yeah. You have the chapter in part two of Board of Directors and the story of Comedus, a sort of ancient example of refusing to listen to. Yeah, it's interesting that Combinus and Mark Shrioz have basically all the same advisors. And one is a philosopher king, and the other is a monster who is killed by a gladiator. And it's that one listened and the other didn't. I mean, Nero has the best advisors you can imagine, too. And he's an interesting case because you have kind of a control.

For the first five years, he's widely seen as a pretty good Roman emperor. There's a quinium neuronis, like the five golden years of Nero. And then what happens? We kills his mother. And then he stops listening to Seneca. And it devolves from there. I've been thinking about this with even something I'm dealing with on the book right now. I can basically write whatever I want, and I don't have to listen to any of the edits from my publisher.

That's not a healthy place to be, and that's not a place that's conducive to getting your best work. Yeah. So I'm trying to figure out how to fix that. I need to find, not a new editor, but I need to find, I need to find a John Landau type. So we talked about that shift from Google Docs into a word document. It was like a big step in the process. and then the next time I see it, you send me the full word document, and you're like, if you had to cut 10% of this, which 10% would it be? Yeah, but how many people are going to say, like, this isn't your best work?

Although, actually, I do remember I sent the obstacles away to someone, an editor I really liked, and I was like, I honestly don't know if this is, like, publishable. It just felt weird to write these, like, 366 discrete, independent things and slapped together to call it a book. Like I, it was unlike anything I'd done and there wasn't really, I just didn't know if it would work. Yeah. And I had like some very strong second thoughts before I sent it into the publisher. And this person was like pretty negative on it themselves. Yeah. Like more negative than I was.

And I took some of their advice and other advice. Anyways, then it came out and it's so like crazy. Yeah. So what do you take from that? Right. Like this is what I mean. It's very hard to know what lessons to take from things. and how to stay sane is the challenge.

Yeah. And then with a creative project, like, it's so difficult to know because it's just like a question of taste and like, do you trust that person's taste? Yeah. Maybe they were right. Maybe the criticism was totally right and it could have been better. Maybe the criticism was right and it's a fluke that it sold.

You know, there's like it's impossible to know what lesson to take from us. Other than intellectual humility, like William Goldman's Nick, nobody knows anything. Nobody knows. Yeah. Is it meaningful and interesting to you? Have you done your best? Yeah. Was it challenging to do?

You're on steadier ground when you think about those. So what happened that you get the negative feedback from the editor? Obviously, the book ultimately was published. Yeah. That's what I'm saying. I don't know. Like, I mean, I obviously didn't listen. Yeah.

But so is the lesson I shouldn't listen? Right. You know, that's what I mean. Like, yes, that could have been one of the takeaways of never listened to editors. And then I could have sent in the next book, and it could have been actual shit. And then if someone told me it was actual shit, I'd be like, well, you were wrong last time. Yeah. Like when Elon Musk was starting SpaceX, his friends had an actual intervention.

Like, they sat him down and had an AA-style intervention. So when some people were like, Twitter's a bad idea. Why would you listen? Yeah. What was it that you ultimately, you said you weren't sure it was publishable? You're always insecure about it. Yeah. And then I think I read it a couple more times.

I think I made some improvements. I think I addressed where I thought I was weak. And then also I trusted some other people. You know, my agent thought it was good. That's Steve, who I worked on it with. My publisher thought I was good. Samantha thought it was good. And then also, so what?

You know? Yeah. What happens if you're wrong? Yeah. I wanted to ask about obstacle, ego, stillness, became a trilogy. Yeah. I mean, and are they a trilogy? They're just, sure, you can buy them in a box. Yeah. Other than stylistically, they were three discrete ideas largely, or there were three distinct ideas influenced by Stoiclaus. Yeah. In this series, you set out knowing it was going to be four books. Sure.

What were the challenges or differences of like, because one book, you know, is like an overwhelming. Where does all the courage stories? are basically justice stories or they're not good stories. It's like, let me tell you about this courageous person who was robbing banks or whatever. This courageous person who conquered and raped and murdered for no... Like all, you know, they're all related. That was the tricky part of the series.

Even Zeno, 2,500 years ago, said they are, like, distinct but inseparable from each other. And I think that's about as well said as you're... can say it. Yeah. Like, none of them work in isolation. All of them inform each other. And they are each made up of sub-v virtues, which also have overlap with each other. Yeah. Well, I forget which chapter was that went, got pushed through the whole series. Yeah, which one was that? Did it end up making it in the book at all? I can't remember. But it's an interesting example of how, like, stuff was able to work in each of the four books. We should find out what chapter that was.

There was one that started in courage, moved to discipline, moved to justice, and then I think I thought I was going to go on wisdom, and I don't know if it did. Yeah, I can't remember. We should find that. Yeah. But yeah, there was a bunch of chapters. And then obviously I kept pushing no cards. There's probably two or three thousand unused note cards from the whole series that I was just like, I'll push this, I'll push this. And then I just never ended up using it.

So there was just a lot of, a lot of that. And I wish now I could go back and write the courage book again. that would be my dream. Really? Yeah. I mean, I think I'm a much better writer. Yeah. I mean, I don't think I would do it from scratch, but I would just, I'd beef it up a little bit.

Maybe I will at some point. I don't think I'd touch the other three, but I'd encourage a little more. Just because it's like courage, it's like the intro for wisdom. Like, it was in the ballpark of what I wanted. Got into my head, I could leave it. But I discovered some things doing the other three books that I would tighten up on. even just i mean the first one you're coming up with the style but then you're also perfecting it on two and three and four have the quote from gibbon in the afterward of when he

completed decline and fall yeah yeah about taking leave from an old friend yeah how does it feel to take leave from the series you know not as bad as i thought it would be i mean i did i have liked knowing that i've got this sort of clear trajectory and what i'm supposed to be working on and everything I'm researching is so everything you read can fit in one of those four but I'm so excited about the next that's been the tragedy of the blessing and the curse of the track I've been on is that I always in the middle of what I'm doing next as I am promoting and talking about the one I'm just putting out yeah so like I would love to just be nerding out about the one I'm in but it's uh that won't come out for 18 months yeah so the next

three are in various stages. Is it three or four? What do I have? Yeah, at least three. Wait, yeah, I have three. But some of them are, one's kind of a greatest hits album. Yeah. Kind of, I think of the thing.

We good? I've got, yeah. Do we do it all? I think we did it. All right. So I have a question for you. Yes. What's going on with your book?

It's been a real head game. Why is it a head game? I think a lot of, like, the insecurity of, is this good, scrapping it, feeling. it could be better. I've had a lot of stops and starts with different ways of structuring it. Are you still with the last one we talked about? Or do you scrap that?

Scrapped. Really? Yeah. And now I think where I'm at now is like not needing to know the structure before writing. And now I'm just writing. And I remember I was talking to James Clear like a year ago. And I asked him, when did he come to the first? four parts of atomic habits.

And it was like he had finished the book and realized, oh, they fit in. And so now I'm like trying to do that of just like writing the main things I want to get into the book. And then the thing I would say. Yeah. And this is where I think you're a little stuck. And that's why I was telling you the story about Daily Stoic is I bet he didn't figure that out.

I bet that emerged from the process. further along in the process than you currently are. That's what I mean. Yes. No, no, but what I mean is that I'm sure that that came once the book had been submitted in some way. Like, I think you might be hoping that there's some moment when it all becomes clear to you and you feel good about it. That's what I'm like, you don't feel good about it literally until after it comes out. Like, I felt concerned about this book as I was reading the audiobook in this room.

Yeah. So I think you are sometimes taking the thing down to the studs because you're not feeling a certain way about it and it may be closer. You may need to come to terms of the fact that you will never feel the way that you're feeling. Yeah. And if you are to get to the place that you need to get to, chances are you are not going to be the sole originator of that feeling. It's going to come from and it's not good to be motivated by other people. But I think you might need the sensation of doing it. and then them going, this is awesome. And then me reading and going, this is great. Like, you're, I think you are expecting to feel a certain way that you are not capable of feeling because, one, you're you, but two, no one ever feels that way. Yeah. But you should have some sense of this because you've seen some other books go through the process. But like, you saw the manuscripts, this book or a lot of my books, and then you saw the finished one. Obviously, I'm the reason it got from here to there, but I'm not the only reason I got from here to there.

And part of it is just the process itself. Part of what you're feeling is the fact that it's between two covers and it's designed and all the titles. You know, like, that's a post-production feeling, not a word document feeling. Yeah. You know what I mean? Yeah. But I'm still struggling with like, like, it needs some sort of arc or like. But I think you think you are going to figure that out.

And you're not fully taking advantage of the collective. knowledge around you. Yeah. Like you think Robert Green couldn't figure that out or give you a pretty good piece of advice or Rick couldn't look at, you know, like there's other people. You're right. I think you're expecting yourself to have the ability to solve a complex problem that you've not solved before.

Yeah. So maybe you'll do it, but it'll just take you an unlimited amount. And also the other thing is like this is not supposed to be your, sometimes it works out as it did for James or. Mark Manson where, like, their first book comes out and it's this monster thing. That almost certainly will not be the case. Yeah. And this is probably not the book you were meant to write.

Like, I'm not saying it's not a, it's not a book you were meant to write. Yeah, yeah. No, I know what you mean. But, like, this is probably your one of six or one of 16. You don't know. Yeah. So you have to do it. This is like the experience chart.

You just need to do it. And that may require you accepting. that you're not going to do it on this one. Yeah, like the, you used the example of, like, Michael Lewis meeting the money ball idea. Yeah, yeah, he had to do like 10 books to get there or whatever. You don't know what that is.

Yeah. It could be, you could meet that on the, your second idea could be that. But, like, chances are, this is not how most people are going to interact. This is not the thing that most people who are going to read your stuff. Yeah.

We'll even read. I also, like, I wanted to be, do, like, well enough to earn the right to do another one and so it's like most people get two shot like you have to really that would be another thing most you have to really fuck this up to not get another shot you might not get a shot with these people but like you're starting here like do you know what I'm like you're not like hey I got a walk on audition at this for this like you got drafted very high like you signed a major book deal with a major publisher that has pretty high expectations but not insane expectations.

So like the degree to which you have to fuck up to not get a second chance is like almost impossible as far as finishing a book. Now if you don't finish it and you have to push it again, you could be the person that never arrives. But if you do the thing,

there's no universe in which it flops so hard that you don't get a second try. So you've got to figure out The actual stakes are not how it does. Yeah. The actual stakes are, do you do it? Right. And as long as you do it, you won.

Yeah. 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. You know,