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Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:02 Ryan Holiday? Welcome to the Daily Stoic Podcast, where each day we read a passage of ancient wisdom designed to help you in your everyday life. On Tuesdays, we take a closer look at these Stoic ideas and how we can apply them in our actual lives. Thanks for listening, and I hope you enjoy.
0:29 Ryan Holiday? This is why we're afraid.
0:33 Ryan Holiday? The ancient world had all the same natural events we have today: earthquakes, lightning, tornadoes, volcanoes. These things were unexpected, terrifying, disruptive, and often deadly. Today, many parts of America will experience a solar eclipse. In this instance, a uniquely rare phenomenon, since the proximity of the moon to the earth will increase the duration and the totality of the eclipse. But like the others we mentioned, this natural event happened in Greece and Rome too. Imagine what it must have been like for the world to suddenly go dark. In "The Obstacle is the Way and Encourages Calling," there's a famous story about Pericles, the Athenian statesman and general. During a naval mission in the Peloponnesian War,
1:16 Ryan Holiday? his fleet of 150 ships was thrown into disarray by an eclipse by which many believed to be an evil portent. To illustrate that they had nothing to worry about, Pericles threw a cloak over a man. "Are you scared now?" he asked. "No," the man said. "What do you care if the cause of darkness differs?" Another time, in the face of a fearful storm, Pericles grabbed two large rocks and smashed them together. "What do you think thunder is?" Pericles said to his men. "But the clouds doing the same thing." The truth is that most of the things we're afraid of is rooted in a similar ignorance. If you don't know what a tornado is or what's behind an earthquake, it may well seem like the wrath of a vengeful god. But then you learn about tectonic plates or atmospheric
2:01 Ryan Holiday? pressure, and it's not quite so scary. It can still hurt you, of course, but you'll both be better prepared and less likely to take it personally. When Seneca said he pitied the man who had never been knocked down or bloodied by life, this is what he was referring to. When the Stoics drove to be more than pen and ink philosophers, this was why. They knew that you had to be exposed to things, to places, to people, to phenomena. Otherwise, you'd be afraid of them. You wouldn't understand. You couldn't draw analogies. You couldn't explain or help reassure others. We fear what we don't understand. We are vulnerable to what we can't explain. And this is why science and history and good old personal experience are so essential. They make us wiser, but also braver. Because now we know. And once we know, then we know what to do.
2:46 Ryan Holiday? We know how to prepare, or in the case of today's eclipse, how to appreciate and enjoy a beautiful and fleeting moment, which, as a reminder, you should not stare directly at. Anyways, I've always loved this story about Pericles. I think it first appears in Thucydides, maybe? Or maybe it's Plutarch. I don't remember. But I've loved it. I've loved it always. And it's one of the first stories I wrote when I was writing The Obstacles Away. Hang on one second. Yes, buddy. Jonesy's definitely not in here, but I like that you're playing hide and seek. Can I finish recording this, though, bud? Everyone's, everyone on the podcast's gonna hear you doing this. But I promise you didn't
3:26 Ryan Holiday? come and hide in my office, because the door was shut. But you're, you're being very thorough. Sorry, that was my kids playing hide and seek. The point is, I put that story in The Obstacles Away before I had kids, before I even knew I would have kids. Here we are 10-plus years later, and I think the story holds up. Holds up for 2,000-plus years for a good reason. And then I talked about it again in Courageous Calling. It's, it's right there at the beginning. And let's see what chapter it's in. My favorite chapter in that book is the important thing is not to be afraid, but it's, we defeat fear with logic. Actually, has one of my favorite acronyms. In sobriety, they have this saying, false
4:07 Ryan Holiday? evidence appearing real, or fear. That's what fear stands for. It's about exactly scenarios like that. So that's today's message. And I hope you enjoyed the eclipse. It should be really beautiful and awesome here in Austin. And I'll let you go after it.
4:34 Ryan Holiday? How has Stoicism helped you? I mean, you've done very well. You've done lots of interesting things. You've been at the top of the author game, the podcast game. You've been a great investor. How do you think of Stoicism in that sense? As something that helps you deal with what we would call champagne problems? Or too much of a good thing? You know, like Stoicism is also there.
4:54 Speaker 01 I can see the YouTube thumbnail now. Tim Ferriss on champagne problems.
4:58 Speaker 01 There are a few things that immediately come to mind. So the first is I do a lot of things that I know are perceived by many people to be high risk, that I don't consider high risk at all, because I've run through exercises and journaling and so on, that lean very heavily on Stoic practices.
5:16 Ryan Holiday? Yeah.
5:17 Speaker 01 And have come to the definitive conclusion that this is not holistically high risk.
5:22 Ryan Holiday? I see.
5:23 Speaker 01 In the long game.
5:24 Ryan Holiday? Yeah.
5:25 Speaker 01 Right? Like the real world MBA, where I traded Stanford Business School for the...
5:33 Ryan Holiday? Crucible of angel investing.
5:35 Speaker 01 That's right. The, in theory, Tim Ferriss Fund of Angel Investing that I deployed over two years.
5:43 Speaker 01 And yes, there was a risk. Even the expectation, it wasn't even just a risk. I expected that, like tuition, that money would vanish. And I was like, okay, let's assume the money vanishes.
5:54 Ryan Holiday? Yeah.
5:54 Speaker 01 How can I approach the angel investing in such a way that my skills and relationships developed over that period of time far exceed what I am expecting to lose?
6:06 Ryan Holiday? Yeah.
6:07 Speaker 01 And so I pulled the trigger. Now, the timing was also incredibly lucky in retrospect. At the time, it wasn't obvious, but in retrospect, it was very lucky. But there was also some deliberation around it in the sense that...
6:22 Speaker 01 And I think this is compatible with, it might not be verbatim reflective of Stoic writings.
6:28 Ryan Holiday? Yeah.
6:29 Speaker 01 But thinking about competition very carefully. In other words, so this is very, Seneca is not the only who has written about this. But in terms of competing with your peers and
6:44 Ryan Holiday? Yes, but keeping up with the Joneses.
6:46 Speaker 01 Keeping up with the Joneses, oh, you want to wear a purple tunic, do you? Hmm, let's talk about that.
6:52 Ryan Holiday? You think you're a success, that person has more than you.
6:54 Speaker 01 Yeah, right, right. You feel like you need to go to the banquets and you need to do this and you need to do that. When I find an area that is crowded or competitive, I look at that as an opportunity to find something that is very uncrowded.
7:09 Ryan Holiday? Sure.
7:09 Speaker 01 So that has also helped me. For instance, I'm coming up on the 10th year of the podcast and podcasting has become incredibly competitive.
7:17 Ryan Holiday? Yeah.
7:18 Speaker 01 And there was a long time when I felt like I was category of one. And if I'm being honest with myself, that's no longer the case. There are some very, very good interviewers out there, yourself among them. And the production quality has gone parabolic.
7:36 Ryan Holiday? Yeah.
7:37 Speaker 01 It is, it is going to be harder to build a business and to fight for, successfully fight for attention
7:49 Ryan Holiday? Sure.
7:49 Speaker 01 in this particular format. And I love doing my podcast, I'm going to continue doing it. However, because I would pay to have these conversations anyway, by and large.
8:02 Speaker 01 I'm taking a moment, say, all right, wait a second. When I did angel investing from, say, 2008 to 2015, it got crowded. I felt like it went from single deck blackjack, where you could kind of count the cards to like, you know, five deck. And then the, the, the table stakes got a lot higher.
8:19 Ryan Holiday? Yeah.
8:20 Speaker 01 Because the terms got weird, there was a lot of money coming in from places like China and sovereign wealth funds. And I was like, oh, man, this is going to get very, now the risk is real for me financially.
8:29 Ryan Holiday? Sure.
8:31 Speaker 01 So I stopped for a while and I've done that over and over again, right? Stop the books for a while. And in this particular case, I'm like, all right, I may not find an answer, but it would be a mistake not to look for an answer. Like, what's neglected? And that's not necessarily something new. For instance, I think text is neglected.
8:50 Ryan Holiday? Yes.
8:50 Speaker 01 I think writing is neglected.
8:51 Ryan Holiday? Yes.
8:52 Speaker 01 And text isn't dead. It's just not surfaced by the algorithms. It's just not favored at the moment, but...
9:01 Ryan Holiday? It's the most perennial of mediums.
9:03 Speaker 01 It's the most perennial and it's the hardest. So if I'm looking at differentiation and competitive advantage, you have this too, right? You can write. Writing's hard.
9:12 Ryan Holiday? Yeah.
9:13 Speaker 01 Writing is very, very hard, at least for me. And for that reason, I'm like, all right, well, maybe it's just the return to basics in that sense. Maybe it's fitting something old into a new vehicle, et cetera, et cetera. Let's come up with a lot of bad ideas to see if there's maybe one or two good ideas we can test. And so to come back to your question, though, I think that that is a way of avoiding comparison with others that can lead directly to outperformance, if we're talking about success in financial terms. But it's also, it's also very compatible with success on your own terms.
9:57 Ryan Holiday? Mm-hmm.
9:58 Speaker 01 Right? I think Kevin Kelly's a great example of this, right? Has really forged his own life. There are other people for sure, but he's very good at questioning basic assumptions.
10:09 Ryan Holiday? Yeah.
10:09 Speaker 01 That are common, right? They're so common that it's, it's, it's taken to be fact, but in most instances, you can kind of negotiate reality around a lot of these assumptions.
10:21 Ryan Holiday? I was thinking of other sort of success problems that socialism helps with, like haters is probably one, or people who don't like you, or negative attention on top of?
10:29 Speaker 01 Yeah. I mean, the more, especially if you're, if your version of success or what you're pursuing is going to make you more public,
10:38 Ryan Holiday? Yeah.
10:39 Speaker 01 you are going to have to deal with all sorts of things at, at least at current.
10:46 Speaker 01 You have not faced this magnitude of negative attention.
10:51 Ryan Holiday? Yes.
10:52 Speaker 01 And I've seen people buckle under that if they don't have the toolkit. And the toolkit doesn't have to be sophisticated, by the way. Like, rule number one, don't go looking for it.
11:00 Ryan Holiday? Yeah, sure.
11:02 Speaker 01 It's kind of like, all right, if you're gonna like do shuffle sprints on top of like broken floorboards, you're gonna stub your toe all the time. And then, I mean, I'll admire you if you have the best stubbed toe fix, but maybe you just shouldn't run across the floorboards barefoot, which is what a lot of folks do when they're kind of hunting for comments, but being human, ending up fixating on the one or two people who are awful.
11:26 Ryan Holiday? I remember one time you said something like, okay, so let's say, how many people know who you are, right? Like, the first part of your career as a creative person, really, even anything that relies on the public, is you want lots of people to find out who you are. Your first problem is a lack of awareness. And then you get the awareness, now, a certain percentage of those people are not gonna like you, or they're gonna have had a bad experience, or you're gonna turn to something.
11:48 Speaker 01 Or they're gonna be nuts.
11:49 Ryan Holiday? Yeah, right. So, like, you know, Daily Stoic has, let's say, 3 million Instagram followers. So let's say 10% of those people are just not fans. That's hundreds of thousands of people who just plain know, who know who you are, but don't like you. Whereas in normal life, you know, if 10% of the people you meet don't like you, those people could fit in a small SUV. You know what I mean? Like, it's not, it's not that many people.
12:11 Speaker 01 And also, like, 20 years ago, they're not enabled with the ability to publicly
12:16 Ryan Holiday? They can't reach all the other people.
12:17 Speaker 01 Yell at you.
12:18 Ryan Holiday? Right. And so, so it's, I think that's a very key, so Mark Sturris has to come to terms with the fact that he's the emperor of Rome. Some people don't even like that there's an emperor. Some people don't like him for good reasons, some people don't like him for bad reasons. But the point is, you're not gonna please everyone. And in fact, part of the job is just putting up with the fact that a bunch of people hate you.
12:39 Ryan Holiday? Having to come to terms with the fact that, one, it's outside your control. You can't make everyone like you. And two, if you try to make those people who don't like you like you, or you spend your time obsessing about them, what you're doing is making yourself miserable and not servicing or serving the people and things that do like you, that you are good at.
13:01 Speaker 01 Definitely. I was wondering, I don't know if you know this. This is a pretty sort of arcane fact to ask for. But do you have any idea what the greater, not the Roman Empire, but the Greater Rome area, let's just call it, just like you'd have the Greater Austin area? Or Rome Central? Do you have any idea what the population was around Marcus Aurelius's day?
13:22 Ryan Holiday? So the empire I know, because I looked it up for something, is like 50 million people. So let's say Rome is 10% of that, right? There's still millions of people, right?
13:33 Speaker 01 Where I was going with that is like more people may dislike you
13:37 Ryan Holiday? Yes.
13:37 Speaker 01 and me individually
13:39 Ryan Holiday? Yeah.
13:40 Speaker 01 than hated Marcus Aurelius
13:41 Ryan Holiday? Sure.
13:42 Speaker 01 at his peak as the last of the great emperors of Rome.
13:46 Ryan Holiday? Yeah, yeah, totally.
13:47 Speaker 01 Which is kind of hilarious to think about.
13:49 Ryan Holiday? Or to think there's probably more Stoics now than have ever existed before in history. There may be more, there may be more people who know about Stoicism, but don't like me specifically than have ever been interested in Stoicism ever. Right? Like, you know, the numbers get really big, really fast, because that's what technology allows for. When you live in a world of 8 billion people, technology allows you to reach lots and lots of people. And it's not healthy or realistic for humans to be subjected to that. But we are subjected to it, right? Like, so you think success is going to be amazing, and it is in a lot of ways, but it's subjecting you to a fundamentally unnatural, really difficult thing, which is like, you have to wake up and deal with the weight of the fact
14:34 Ryan Holiday? that like lots of people like hate you, like they hate you. And if you don't have the sort of fortitude and the confidence to just sit with that and to not let it eat at you or make you swerve off what you think you're supposed to be doing, like you're going to get eaten alive.
14:54 Speaker 01 Yeah, you'll get eaten alive.
14:56 Ryan Holiday? You'll eat yourself alive.
14:57 Speaker 01 You'll eat yourself alive. And I think...
15:02 Speaker 01 Buddhistism and reflecting on applications of Stoic-like thinking, right? Because I'm not a Stoic fundamentalist. Sure. I'm not like, this is, this is the scripture. This is the end all be all. Well, let's like extend that. It isn't one. Right, exactly. So like, let's extend, let's expand. All right. What other ways could this type of thinking apply? And I think that extends to 80/20 principle, Richard Koch-type stuff. I think it extends to, it's really about the number of people who get it, not the number of people who don't get it. Kevin Kelly, 1,000 true fans type of thinking. Blue ocean versus red ocean, blue ocean strategy kind of stuff. These are all highly, highly compatible.
15:46 Speaker 01 And I would go further to say, there are a lot of people who, at this point, they've probably heard the word Stoic. Yeah. At least in the modern sense. Yeah, lowercase. But they're not familiar with the canon of Stoicism. Yet, if you, if you look at anyone who has thrived in what most people consider high-stress environments, they're going to walk the walk. I just, I think that there's such a selection bias, there's a survival bias towards anyone who indirectly or directly has put into practice these principles on a regular basis that, if you look at, and, you know, this is just the hypotheticals. I haven't asked these people.
16:30 Speaker 01 Like, anyone from a Bob Iger to a hedge fund manager to an exceptionally good athlete who has had longevity, if you were to sit them down and walk them through Marcus Aurelius and so on for the first time, they'd be like, oh, yeah, oh, yeah, yeah, yeah. No, that's how I lived my life.
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