Pod Insights The Daily Stoic Premium (🔓) Not Seeking Wisdom DESTROYS Great Minds | Ryan Holiday & Billy Oppenheimer About this episode 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 Facebook 📢 Share | ⚙️ Manage Subscription
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:03 Ryan Holiday? 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,
0:46 Ryan Holiday? and most importantly, to prepare for what the week ahead may bring.
0:54 Ryan Holiday? 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 Greene 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 built all my books around. Robert taught me that, and then I, in turn, 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, Billy Oppenheimer, who has become a great writer in his own right
1:39 Ryan Holiday? 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 worked 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 the Coaching Tree chapter. And right then, 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.
2:25 Ryan Holiday? 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,
3:09 Ryan Holiday? 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?
3:53 Ryan Holiday? 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.
4:11 Ryan Holiday? And so, you know, obviously, as I was putting that together, I was thinking about Billy. I was thinking about my time with Robert Greene. 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 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. He's got to finish this book, man. Let's, 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 BillyOppenheimer.com. And as I was saying,
4:56 Ryan Holiday? 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 to me. 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
5:41 Ryan Holiday? order it. This first week is where it's all at. Grab it on Audible. Grab it as an ebook. Grab the signed editions from The Painted Porch at DailyStoic.com/Wisdom. Swing by The Painted Porch, swing by Barnes and 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.
6:09 Billy Oppenheimer? Trying to think, like, how do we segue into part two?
6:12 Ryan Holiday? Of the book?
6:13 Billy Oppenheimer? Yeah. Musk as a cautionary tale and that part just being like some of the anti-wisdom
6:19 Ryan Holiday? Yeah.
6:20 Billy Oppenheimer? things to avoid.
6:21 Ryan Holiday? He's the only one in the whole series. There are some cautionary tales, but he's the only one. I tried to pick one really impressive person for part one, part two, part three of each book. Like, different than obstacle, he goes, I would really do like a very big deep dive into characters. Senator Florence, Stengel, De Gaulle, Taine, Queen Elizabeth, Lou Gehrig, Gandhi, 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.
7:04 Ryan Holiday? Like, it is fascinating to me how he went from hero to villain so quickly. And what happened?
7:09 Billy Oppenheimer? Yeah.
7:09 Ryan Holiday? 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.
7:16 Billy Oppenheimer? Yeah.
7:17 Ryan Holiday? And that was harder because it's also something that's like happening. And I, like, the Doge stuff happened after I finished.
7:23 Billy Oppenheimer? Yeah.
7:24 Ryan Holiday? So then I had to add some stuff back. But like, that was a developing story. It was, that was a weird one, too. It was also harder because 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.
7:39 Billy Oppenheimer? Yeah.
7:40 Ryan Holiday? 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.
7:55 Billy Oppenheimer? Yeah.
7:56 Ryan Holiday? They were a little fresher.
7:57 Billy Oppenheimer? Yeah. At some stage, you had, I don't know if concern is the right word, but just like, a lot of people would maybe disagree with this take.
8:05 Ryan Holiday? Sure. Yeah.
8:06 Billy Oppenheimer? But now.
8:07 Ryan Holiday? Yeah, you'd be there. If you don't, when you look at him and you see, if you're not like, whoa, that's, uh, something went sideways there. You're probably also brain fucked.
8:18 Billy Oppenheimer? Yeah.
8:19 Ryan Holiday? 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, 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 had to spend 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.
8:48 Billy Oppenheimer? Yeah. What would you say is like the, the big lesson from him of what not to do?
8:53 Ryan Holiday? 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, is 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.
9:26 Billy Oppenheimer? Yeah.
9:26 Ryan Holiday? Like, there is, people go, oh, podcasts are great, or, oh, you know, I have 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.
9:52 Billy Oppenheimer? Yeah.
9:53 Ryan Holiday? 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, is like anti-Semitic and sexist and racist and unhinged, you know? And when you read that, suddenly, the current Musk doesn't seem like an independent creation.
10:38 Ryan Holiday? It seems like the natural evolution of that lineage. Which is, like, you read anything on, like, William F. Buckley's book I was telling you about?
10:48 Billy Oppenheimer? Yeah, I'm like a third of the way.
10:51 Ryan Holiday? The book's incredible, is it not?
10:52 Billy Oppenheimer? It's really good.
10:53 Ryan Holiday? Like, to be able to make a compelling biography of someone you would not give a shit about is like a very
10:59 Billy Oppenheimer? Yeah.
11:00 Ryan Holiday? impressive feat. But have you read much about his father yet? Is that, oh, Buckley's father isn't? At the beginning, maybe 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.
11:17 Billy Oppenheimer? Yeah.
11:18 Ryan Holiday? 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 an 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.
12:03 Ryan Holiday? Like, you did not independently come to these controversial ideas, but not from a place of bigotry.
12:10 Billy Oppenheimer? Yeah.
12:11 Ryan Holiday? If your bigot father had all the same views and you grew up with that person. So like, you have to trace this stuff back and then you go, oh, okay, they're able to present it as this.
12:22 Billy Oppenheimer? Yeah.
12:22 Ryan Holiday? But when you have the larger context.
12:24 Billy Oppenheimer? There's a video of Francis Ford Coppola.
12:27 Ryan Holiday? Yeah.
12:27 Billy Oppenheimer? 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."
12:36 Ryan Holiday? Yeah, sure.
12:38 Billy Oppenheimer? And that's kind of like what he's.
12:39 Ryan Holiday? Yes.
12:39 Billy Oppenheimer? Exploring in a lot of his movies.
12:41 Ryan Holiday? Yeah, yeah, yeah. That's totally what it is. That's not to say that like it had to go this way.
12:46 Billy Oppenheimer? Yeah.
12:46 Ryan Holiday? 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. That doesn't mean you weren't a great political organizer.
13:25 Ryan Holiday? 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, 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?
14:06 Ryan Holiday? And that's this furthering civilization is just the story to justify it. Yeah. 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 antisemitic 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? Yeah. You know, right?
14:49 Ryan Holiday? Or like, what is fascinating about reading biographies is that like, this stack of pages makes you understand the person better than they understand themselves in some ways. Mm-hmm. And how rare self-awareness is. Yeah. Not to say I have it, because if you think you do, you almost don't. Yeah. But the, but the point is, it's fascinating how quickly the trajectory or the underlying forces in a person's life can be made clear to everyone but themselves.
15:34 Billy Oppenheimer? And he almost seems to like, cut ties with anyone who's willing to.
15:39 Ryan Holiday? Did you see that Sam, the Sam Harris thing?
15:41 Billy Oppenheimer? No.
15:42 Ryan Holiday? 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.
16:01 Billy Oppenheimer? Well, there's the story you tell of the, I don't, 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.
16:12 Ryan Holiday? 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 Musk is like, fuck you, get the fuck out of it, you know, and fires him.
16:22 Billy Oppenheimer? Yeah.
16:23 Ryan Holiday? And then, then he looks around the room and he's like, why isn't anyone else talking? You know, like, I, 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, 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
17:05 Ryan Holiday? is the reflection off your 70 million. Is he up? 70 million was like, the, 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. Forty four billion.
17:24 Billy Oppenheimer? Yeah.
17:25 Ryan Holiday? Um, and it was like a rounding error to him. But, uh, just, just to be successful at any level is alienating and isolating and the air gets thinner. But, uh, then if you eschew human interaction for an unhealthy amount of online mob dynamics.
17:44 Billy Oppenheimer? Yeah.
17:45 Ryan Holiday? 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 long time person who is his, like when I was working on the Raveling book.
18:18 Billy Oppenheimer? Yeah.
18:18 Ryan Holiday? He was like, call, and he said his name, who I won't say, because maybe it's private, but he's a call to this person. And it was like Michael Jordan's assistant of like 30 years.
18:27 Billy Oppenheimer? Yeah.
18:28 Ryan Holiday? You know, you need, at that level, you need continuity and consistency.
18:33 Billy Oppenheimer? Yeah.
18:34 Ryan Holiday? 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 a inhuman pace with the stakes as high as they are, that he would be fucking winging it is.
18:49 Billy Oppenheimer? Yeah. And just like, what does it say that no one's stayed in his circle for?
18:56 Ryan Holiday? Yeah.
18:56 Billy Oppenheimer? A long time.
18:57 Ryan Holiday? Yeah.
18:57 Billy Oppenheimer? Like Rav had like relationships for sixty years.
19:02 Ryan Holiday? No, no, no, you, you need that. It's not healthy and it's, it's destabilizing. Like success is in and of itself destabilizing. So if you don't create stabilizers, you're gonna fall off.
19:14 Billy Oppenheimer? Another cautionary tale in the book is SBF. And his
19:19 Ryan Holiday? Although it's funny that I'll probably get pardoned and then that story won't seem as.
19:23 Billy Oppenheimer? I still think he's.
19:25 Ryan Holiday? Well, of course, no, no, I'm just saying, I'm just saying, like, we live in a time where that that should be a universal cautionary tale.
19:31 Billy Oppenheimer? Yeah.
19:32 Ryan Holiday? 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.
19:50 Billy Oppenheimer? Yeah.
19:51 Ryan Holiday? 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 to love celebrating unconventional characters.
20:14 Billy Oppenheimer? Yeah.
20:15 Ryan Holiday? And, yeah, to me, that it is a withering picture.
20:20 Billy Oppenheimer? Yeah.
20:21 Ryan Holiday? Of him, that none of you wouldn't say that about any of his other books. Except for maybe the Jim Clark in the the new new thing, which is a great book that more people should have read. 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.
21:00 Billy Oppenheimer? Yeah, that 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?
21:09 Ryan Holiday? Yeah, yeah, if you're so smart, why aren't you happy? I've heard it.
21:12 Billy Oppenheimer? Yeah, something like that. And Musk, like, there's just some really sad clips of him out there of just like, well, you wouldn't want to be. And he says that, you know, like, you wouldn't want to be me.
21:23 Ryan Holiday? 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, I can't wait to read the book. And I was like, I'm not sure you do.
21:43 Billy Oppenheimer? Had you told him that?
21:45 Ryan Holiday? No, no, they were just, we're talking about wisdom generally, virtue and wisdom. They had like a philosophy degree. They were like excited.
21:50 Billy Oppenheimer? Yeah.
21:51 Ryan Holiday? And then they were like, oh, that's all start with that one. And I was like, please don't.
21:55 Billy Oppenheimer? Or maybe that's like the person who needs to read it.
21:58 Ryan Holiday? Yeah. Although, Joel, when I tell you who this person is, you're, you're okay. I don't want to blow them up or embarrass them. But that was a weird part of it, right? Because like, they just announced like another million square feet they're adding to the SpaceX offices, like, two miles from here.
22:13 Billy Oppenheimer? Yeah.
22:14 Ryan Holiday? Like, if you look at like, if you get like an alert from Twitter or whatever, or an email, and you look at the bottom, it's like Twitter is headquartered in Basterds now. It's crazy.
22:23 Billy Oppenheimer? Right. Like, so you're saying, like, it would have been much easier to not include him in the book in this way?
22:30 Ryan Holiday? I just already know how many, we did a piece the other couple of weeks ago that you helped me with. And the amount of angry emails about it. Like, it's, I just already know. And the people are all, what they're gonna write is like, how could you, like, didn't you understand this was gonna piss someone like me off? It's like, I do, I would just, like, not have to hear from you about it. You just keep it yourself.
22:52 Billy Oppenheimer? But the part two, like, the watching your info diet, not breaking your brain.
22:57 Ryan Holiday? Yes.
22:57 Billy Oppenheimer? And there's a great story of SBF, like, with a journalist of like,
23:01 Ryan Holiday? Oh, yeah, I would never read a book.
23:03 Billy Oppenheimer? Being very skeptical of books.
23:07 Ryan Holiday? He said that, I would never, he was like, if you wrote a book, you fucked up.
23:10 Billy Oppenheimer? Yeah.
23:10 Ryan Holiday? 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 one 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 incuriosity, a fundamental ego, and a fundamental anti-social tendency
23:51 Ryan Holiday? that in the end unraveled 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 encapsured, encapsulates where we are as a society, this sort of death of expertise, the death of real knowledge. It is the Seneca story about, well, I'll 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.
24:36 Ryan Holiday? I thought was interesting about that is that 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. Yeah. Doing that interview. And like, he has the, 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. That is one of the dumbest things that a person has ever said on the record to a journalist. 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...
25:17 Ryan Holiday? Fate in their hand, like, like, most writers would have, that would have changed the entire direction of the piece and it would have become a takedown. Like, that was just a reckless thing to do. Putting aside the fact that it's just dumb and wrong. It's just a dumb thing to say. Like, know your audience. That's a dumb thing to say.
25:33 Billy Oppenheimer? Yeah.
25:34 Ryan Holiday? 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. It's just a dumb, that's a thought you might have. And it, a lot of books are fuckups and do suck. But that's just a dumb thing to say.
25:51 Billy Oppenheimer? Yeah.
25:52 Ryan Holiday? But I thought it was, watching the mental gymnastics of this writer.
25:57 Billy Oppenheimer? Yeah.
25:58 Ryan Holiday? To justify an indictment of his own profession and life's work is also interesting.
26:05 Billy Oppenheimer? Well, yeah, and he like, the piece is like, kind of glowing.
26:09 Ryan Holiday? Yeah, no, that's what I mean. He's like, he knows more than me. He's a genius. You're like, that should have been an Emperor Has No Clothes moment.
26:15 Billy Oppenheimer? Yeah.
26:15 Ryan Holiday? But instead, it's the opposite, which is a big, 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.
26:49 Billy Oppenheimer? Rethink.
26:49 Ryan Holiday? 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.
27:01 Billy Oppenheimer? Yeah.
27:01 Ryan Holiday? Person.
27:02 Billy Oppenheimer? Yeah, I think the writer even has like, a moment of questioning, like.
27:06 Ryan Holiday? There's a little back and forth, and then he's just like, no, no, no, I'm gonna side with you.
27:10 Billy Oppenheimer? But no, like, questioning his own, like. Oh, maybe like
27:14 Ryan Holiday? Yeah, maybe I wasted my life.
27:15 Billy Oppenheimer? Yeah, yeah.
27:17 Ryan Holiday? It's pretty, it's pretty spectacular.
27:19 Billy Oppenheimer? How do you think about the difference between being wise and being really smart?
27:24 Ryan Holiday? Well, a lot of people are really smart and there's not that many wise people.
27:26 Billy Oppenheimer? Yeah.
27:27 Ryan Holiday? And I think the tricky part about being smart is that it makes you more susceptible to being really stupid.
27:34 Billy Oppenheimer? Yeah.
27:34 Ryan Holiday? Because you, like, one of my friends who gave me some great notes on the Musk 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
28:03 Ryan Holiday? 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?
28:28 Billy Oppenheimer? Yeah, and it's just an entire population of people who have had that experience.
28:32 Ryan Holiday? And then you layer on top of that money, fame, bubble, etc. 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, riding 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.
29:06 Billy Oppenheimer? Yeah.
29:06 Ryan Holiday? 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 tenuous stuff.
29:19 Ryan Holiday? 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.
29:29 Billy Oppenheimer? And then each time you get more and more sort of emboldened by like, these people are wrong.
29:34 Ryan Holiday? Yeah.
29:35 Billy Oppenheimer? I have proof that.
29:36 Ryan Holiday? It takes a lot of discipline to start from first principles every time and to not go, these 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.
29:59 Billy Oppenheimer? Yeah.
30:00 Ryan Holiday? 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 a hundred percent wrong, like not what your diet should be. You should not be mostly eating grains and rices 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
30:41 Ryan Holiday? you're trying to feed as many people as, 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 makes fun of you and be like, oh, you're gonna 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 weigh this and they look like this. And then, you know, I think you're gonna be more vulnerable to like, and maybe the vaccine shouldn't be trusted.
31:24 Billy Oppenheimer? Right.
31:24 Ryan Holiday? Or whatever, right? Like when you've had a contrarian bet, it makes it, you start to see that everywhere.
31:29 Billy Oppenheimer? Yeah. And like, what else is wrong? If the food pyramid, you know, have you read the Marc Maron memoir from like early in his career?
31:39 Ryan Holiday? Oh, the, um, yes.
31:41 Billy Oppenheimer? 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 DC and he's like, what are you doing? Like, can you see this is all, and he's just like asking 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.
32:08 Ryan Holiday? Yeah. And that's not to say there, 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.
32:25 Billy Oppenheimer? Yeah.
32:25 Ryan Holiday? 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 in. 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, his trajectory isn't anything like Elon Musk. But there's certainly been, I think you can certainly trace a kind of a, not an overconfidence, but a destabilizing effect that having been right about a lot of things has had.
33:06 Ryan Holiday? And that's, 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. That, and that's the root thing for Elon Musk. When was, when was the last time Elon Musk had a conversation with someone?
33:28 Ryan Holiday? And he thought that person was smarter than him.
33:31 Billy Oppenheimer? Mm hmm.
33:32 Ryan Holiday? Probably a very long time.
33:34 Billy Oppenheimer? Yeah, wow.
33:36 Ryan Holiday? And I guess that's a good question for everyone. When is 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.
33:55 Billy Oppenheimer? Yeah.
34:07 Billy Oppenheimer? You have the chapter in part two of Board of Directors and the story of Commodus, a sort of
34:14 Ryan Holiday? Yeah.
34:15 Billy Oppenheimer? ancient example of refusing to listen to.
34:19 Ryan Holiday? Yeah, it's interesting that Commodus and Mark Schrills 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 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 Quinian Neronus, like the the five golden years of Nero. And then what happens? He 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.
35:04 Ryan Holiday? 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.
35:14 Billy Oppenheimer? Yeah.
35:14 Ryan Holiday? 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.
35:23 Billy Oppenheimer? So we talked about that shift from Google Docs into a Word document. It's like a big step in the process. And then the next time I see you send me the full Word document and you're like, If you had to cut 10% of this, which 10% would it be?
35:39 Ryan Holiday? Yeah, but how many people are gonna say like, eh, 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 discreet, independent things and slap together to call 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.
36:03 Billy Oppenheimer? Yeah.
36:03 Ryan Holiday? 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.
36:12 Billy Oppenheimer? Yeah.
36:13 Ryan Holiday? Like more negative than I was. And I, I took some of their advice, other, anyways. Then it came out and it sold like crazy.
36:20 Billy Oppenheimer? Yeah.
36:20 Ryan Holiday? So what do you take from that?
36:22 Billy Oppenheimer? Right.
36:22 Ryan Holiday? 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.
36:32 Billy Oppenheimer? Yeah, but, and then with a creative project, like, it's so difficult to know. Cause it's just like a question of taste and like, do you trust that person's taste?
36:42 Ryan Holiday? Yeah, maybe they were right. Maybe, maybe their 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.
36:56 Billy Oppenheimer? Yeah.
36:56 Ryan Holiday? Other than intellectual humility, like William Goldman's, like, nobody knows anything. Nobody knows.
37:02 Billy Oppenheimer? Yeah.
37:03 Ryan Holiday? Is it meaningful and interesting to you? Have you done your best?
37:06 Billy Oppenheimer? Yeah.
37:07 Ryan Holiday? Was it challenging to do? You're on steadier ground when you think about those.
37:11 Billy Oppenheimer? So what happened that you get those, the negative feedback from the editor? Obviously, the book ultimately was published.
37:19 Ryan Holiday? Yeah, that's what I'm saying. I don't know. Like, I mean, I obviously didn't listen.
37:22 Billy Oppenheimer? Yeah.
37:23 Ryan Holiday? So, but so is the lesson, I shouldn't listen? You know, that's what I mean, like.
37:27 Billy Oppenheimer? Yes, that could have been one of the takeaways of never listen to editors.
37:31 Ryan Holiday? 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.
37:41 Billy Oppenheimer? Yeah.
37:42 Ryan Holiday? 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 he listen?
37:57 Billy Oppenheimer? Yeah. What was it that you ultimately, you said you weren't sure it was publishable?
38:01 Ryan Holiday? You're always insecure about it.
38:03 Billy Oppenheimer? Yeah.
38:03 Ryan Holiday? 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 it was good. Samantha thought it was good. And then also, so what? You know?
38:24 Billy Oppenheimer? Yeah.
38:25 Ryan Holiday? What happens if you're wrong?
38:26 Billy Oppenheimer? Yeah. I wanted to ask about Obstacle Ego Stillness became a trilogy.
38:31 Ryan Holiday? Yeah, I mean, and are they a trilogy? They're just, they're, sure, you can buy them in a box.
38:35 Billy Oppenheimer? Yeah.
38:36 Ryan Holiday? Other than stylistically, there were three discreet ideas largely, or there were three distinct ideas influenced by Stoic philosophy.
38:44 Billy Oppenheimer? Yeah. In this series, you set out knowing it was gonna be four books.
38:48 Ryan Holiday? Sure.
38:48 Billy Oppenheimer? What were the challenges or differences of like, because one book, you know, is like
38:53 Ryan Holiday? Well, where does courage, where do, 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. Let me tell you this courageous person who conquered and raped and murdered for no, like, all, you know, it's, it's, they're all related. That was the tricky part of the series is, even Xeno, 2,500 years ago, said they are like, distinct but inseparable.
39:22 Billy Oppenheimer? Yeah.
39:22 Ryan Holiday? From each other. And I think that's about as well said as you can say it.
39:27 Billy Oppenheimer? Yeah.
39:27 Ryan Holiday? Like, none of them work in isolation. All of them inform each other. And they are each made up of sub virtues, which also have
39:37 Ryan Holiday? Overlap with each other.
39:38 Billy Oppenheimer? Yeah. Well, I forget which chapter it was that went, got pushed through the whole series.
39:42 Ryan Holiday? Yeah. Which one was that? Did it end up making it in the book at all?
39:44 Billy Oppenheimer? I can't remember, but it's an interesting example of how like stuff was able to work in each of the four books.
39:52 Ryan Holiday? We should find out what chapter that was. There was one that was, 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.
40:01 Billy Oppenheimer? Yeah, I can't remember.
40:01 Ryan Holiday? We should find that.
40:02 Billy Oppenheimer? Yeah.
40:03 Ryan Holiday? But yeah, there was a bunch of chapters and then obviously I kept pushing note cards. There's, there's probably two or 3,000 unused note cards from the whole series that I was just like, I'll push this, I'll push. And then I just never ended up using it. So there, there was just a lot of, a lot of that. And I wish, I wish now I could go back and write the courage book again. That would be my dream.
40:24 Billy Oppenheimer? Really?
40:24 Ryan Holiday? Yeah. I mean, I think I'm a much better writer.
40:27 Billy Oppenheimer? Yeah.
40:27 Ryan Holiday? 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 think courage a little more, just because it's like courage, it's, 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.
40:49 Billy Oppenheimer? Yeah.
40:49 Ryan Holiday? 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.
40:58 Billy Oppenheimer? Have the quote from Gibbon in the afterword of when he.
41:02 Ryan Holiday? Completed decline and fall?
41:04 Billy Oppenheimer? Yeah.
41:04 Ryan Holiday? Yeah. About taking leave from an old friend.
41:06 Billy Oppenheimer? Yeah. How does it feel to take leave from the series?
41:10 Ryan Holiday? 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.
41:39 Billy Oppenheimer? Yeah.
41:40 Ryan Holiday? So like, I would love to just be nerding out about the one I'm in, but it's, that won't come out for 18 months.
41:46 Billy Oppenheimer? Yeah. So the next three are in various stages.
41:51 Ryan Holiday? 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.
42:01 Billy Oppenheimer? Yeah.
42:01 Ryan Holiday? Kind of a thing.
42:02 Billy Oppenheimer? We've got, yeah.
42:04 Ryan Holiday? We do it all?
42:04 Billy Oppenheimer? Think we did it.
42:05 Ryan Holiday? All right. So I have a question for you.
42:07 Billy Oppenheimer? Yes.
42:08 Ryan Holiday? What's going on with your book?
42:09 Billy Oppenheimer? It's been a real head game.
42:12 Ryan Holiday? Why is it a head game?
42:14 Billy Oppenheimer? 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 and.
42:25 Ryan Holiday? Are you still with the last one we talked about? Or did you scrap that?
42:28 Billy Oppenheimer? Scraped.
42:28 Ryan Holiday? Really?
42:29 Billy Oppenheimer? 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 four parts of Atomic Habits?
42:52 Billy Oppenheimer? It was like, he had finished the book.
42:55 Ryan Holiday? Yeah.
42:55 Billy Oppenheimer? And.
42:56 Ryan Holiday? Sure.
42:56 Billy Oppenheimer? 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.
43:05 Ryan Holiday? The thing I would say.
43:06 Billy Oppenheimer? Yeah.
43:07 Ryan Holiday? 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.
43:21 Billy Oppenheimer? That's what I mean.
43:22 Ryan Holiday? 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.
43:36 Billy Oppenheimer? That's.
43:36 Ryan Holiday? And 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.
43:47 Billy Oppenheimer? Yeah.
43:47 Ryan Holiday? 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 with the fact that you will never feel the way that you're feeling.
44:01 Billy Oppenheimer? Yeah.
44:02 Ryan Holiday? 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's, but I think you might need the sensation of doing it and then them going, this is awesome. And then me reading 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.
44:31 Billy Oppenheimer? Yeah.
44:32 Ryan Holiday? 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 it 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 are, you know, like, that's a post-production feeling, not a Word document feeling.
45:01 Billy Oppenheimer? Yeah.
45:02 Ryan Holiday? You know what I mean?
45:03 Billy Oppenheimer? Yeah. But I'm still struggling with like, like, it needs some sort of arc or like.
45:08 Ryan Holiday? But I think you think you are going to figure that out and you're, you're not fully taking advantage of the collective knowledge around you.
45:18 Billy Oppenheimer? Yeah.
45:18 Ryan Holiday? Like, you think Robert Greene 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.
45:26 Billy Oppenheimer? You're right.
45:26 Ryan Holiday? I think you're, I think you're expecting yourself to have the ability to solve a complex problem that you've not solved before.
45:36 Billy Oppenheimer? Yeah.
45:36 Ryan Holiday? 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.
45:53 Billy Oppenheimer? Yeah.
45:54 Ryan Holiday? 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.
46:01 Billy Oppenheimer? Yeah, yeah, no, I know what you mean.
46:02 Ryan Holiday? But like, this is probably your one of six or one of 16. You don't know.
46:08 Billy Oppenheimer? Yeah.
46:09 Ryan Holiday? So you have to do it. This is like the experience chat. You just need to do it.
46:13 Billy Oppenheimer? Mm hmm.
46:14 Ryan Holiday? And that may require you accepting that you're, you're not going to do it on this one.
46:20 Billy Oppenheimer? Yeah, like the, you used the example of like Michael Lewis meeting the Moneyball idea.
46:25 Ryan Holiday? Yeah, he had to do like 10 books to get there or whatever. You don't know what that is.
46:28 Billy Oppenheimer? Yeah.
46:29 Ryan Holiday? It could be, you could meet that on this, 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.
46:40 Billy Oppenheimer? Yeah.
46:41 Ryan Holiday? Will even read.
46:42 Billy Oppenheimer? I also, like, I want it to be, do like, well enough to earn the right to do another one. And so it's like.
46:49 Ryan Holiday? Yeah, but most people get two shot. Like, you have to really, that would be another thing. 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.
47:32 Billy Oppenheimer? Yeah.
47:32 Ryan Holiday? You could be the person that, 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 gotta figure out, the, the actual stakes are not how it does.
47:47 Billy Oppenheimer? Yeah.
47:48 Ryan Holiday? The actual stakes are, do you do it?
47:50 Billy Oppenheimer? Right.
47:51 Ryan Holiday? And as long as you do it, you won.
47:53 Billy Oppenheimer? Yeah.
47:59 Ryan Holiday? 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.
Previous How The Stoic Virtues Became Ryan’s Greatest Test | Billy Oppenheimer & Ryan Holiday Next 7 Stoic Lessons on How To Keep Going Page updated September 29, 2026 · transcript and summary are machine-generated
