


18 Jul 2026 · 1h 5m · 23 chapters

The Roman Republic’s collapse as a warning about how republics fail when the “civic bargain” breaks: citizens lose farms and military eligibility, loyalty shifts from the republic to commanders, and institutions remain but character and trust erode. The episode also argues that compromise, economic stability, and civic education are essential to keep norms alive.
Barry Strauss is a classicist and military/naval historian; professor emeritus at Cornell; senior fellow at the Hoover Institution. He has written 10 ancient-history books, including Jews First Rome and The War That Made the Roman Empire, and hosts the podcast Antiquitas: Leaders and Legends of the Ancient World.
Cato and Cicero are too principled/clean for politics; politicians must compromise on principles while officials remain personally unswayable. The Republic fell over citizenship and economic strain, not just “Caesar vs. Cato.” Assassination of Caesar lacked a plan for the day after; Octavian outmaneuvered Antony and exploited propaganda.
Gracchi land reforms and violent opposition; lowering property qualifications and “pot of gold” land promises; Marius vs. Sulla civil wars; Sulla’s temporary dictatorship becoming effectively permanent; Rubicon; Caesar’s “dignitas” choice; Decius Mus self-sacrifice; Caesar’s Egyptian entanglements and Octavian’s propaganda.
Written by AI. May contain mistakes.
Ryan shares insights from his recent trip to Rome and the lessons learned.
“A republic, it becomes powerful, becomes wealthy, becomes successful.”
Discussion on how ambition and luxury weaken powerful institutions.
“It was fascinating just walking through Rome, looking at it from different vantage points and just thinking about what's happening on the news.”
Introduction of historian Barry Strauss and his relevant works.
“He's a classicist, a military and naval historian.”
Conversation about the state of Western civilization and historical context.
“going to be a crash course on Rome, but really it's a crash course on what happens when a society forgets what made it work in the first place.”
Barry discusses the political roles of Cato and Cicero in Roman history.
“About the state of Western civilization?”
Examination of Cicero's challenges and shortcomings as a politician.
“You know, it's a novel about the revolution in Sicily in 1860.”
Barry outlines the factors leading to the fall of the Roman Republic.
“And so I think that a wise politician understands that.”
Discussion on the reforms proposed by the Gracchi brothers and their impact.
“And Pompey and Caesar both understood that, whereas Cato and Cicero did not.”
Learn about the attempts of the Gracchi brothers to reform military property qualifications in Rome and the resulting civil unrest.
“So suddenly there's not enough people who can meet the military, the property qualification to go into the military.”
Discover how Wayfair can help you create a comfortable home without overspending.
“Like your space should feel like you, should look the way you want it to look.”
Explore the complexities surrounding the fall of the Roman Republic and the intertwined roles of individuals and systemic issues.
“So a couple of things I'm taking from your version of this story.”
Explore Cato's portrayal and the pivotal choices leading to the Republic's fall.
“I mean, he is a tragic figure in the play, but it's a play celebrating primarily the virtues of the person.”
Discuss the decline of patriotism and its implications for society.
“And I don't want to get off topic, but we could talk about why we don't have that anymore.”
Analyze the pivotal decision to assassinate Caesar and its aftermath.
“Like there was this kind of unquestioned obedience.”
Investigate the role of character in leadership during crises, referencing FDR and Lincoln.
“So there's a lot of reasons to want to be with Cleopatra.”
Examine the Stoic perspective on power and the necessity of pragmatism.
“I mean, Caesar did not have to bed the queen of Egypt and produce the next king of Egypt as his illegitimate son.”
Explore how Stoic philosophy relates to leadership, power, and historical figures like Caesar and Cato.
“Again, the Stoics not being pragmatic, but the first thing is it's either Athenodorus or Aristidimus.”
Understand the role of history and education in shaping society and civic values.
“Wealthfront brokerage is not a bank, and the base APY is as of January 30th, 2026 and subject to change.”
Discussing the importance of understanding Greek history and its myths for moral and philosophical debates.
“And you really do have to join the great debate and be part of the great ideas.”
Exploring the challenges and changes in teaching philosophy due to AI, including essay assignments and oral exams.
“Like, Plutarch's a great biographer, even though he's not super accurate, because he's getting to the essence of these figures.”
Examining the limitations and potential of AI tools when researching and asking insightful questions.
“It's to really sit down and think about what you think about whether he should have done this or that.”
Drawing parallels between Socratic questioning and how we should engage with AI responses critically.
“Because it is this kind of, it seems like it's this magical tool, which does have access to ungodly amounts of information.”
Discussing the philosophical overlap between Jewish texts and Stoicism, alongside the exchange of ideas across civilizations.
“which is how do you scale your brain and research?”

Get the gist, explore an idea or ask about something said.
On The Daily Stoic, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00Ryan Holiday: Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.
0:14Ryan Holiday: Hey, it's Ryan. Welcome back to another episode of the Daily Stoic Podcast. So, the whole family just got back from Rome. We spent about two weeks in Italy. We were in Rome, and we were in Sorrento, we were in Capri, and Ischia. But the chunk of the trip, the big chunk of the trip, the trip I was excited about, that my two boys were excited about was the Rome part. We did Greece last year. We did Rome this year. I'll get into all that in another episode. But the thing about Rome is not that it feels ancient. It doesn't. It feels familiar. It's timely and timeless, right? A republic, it becomes powerful, becomes wealthy, becomes successful.
0:53Ryan Holiday: It's filled with great and brilliant and fascinating characters. But then slowly the very things that made it strong began to weaken it. Ambition and competence. Ambition replaces service. Careerism replaces competence. Luxury replaces discipline. The institutions are still there in paper. The power is there. It's still the center of the world. But the character and the trust and the values that made those institutions work begin to wane or finally disappear. This is the story of Rome, but it's also a warning. It was fascinating just walking through Rome, looking at it from different vantage points and just thinking about what's happening on the news.
1:35Ryan Holiday: It both puts it in perspective and then it also makes it urgent. And it brings so many of the questions that we're asking ourselves right now. It makes them painfully real. What does courage look like when the crowd is wrong? What does duty and responsibility look like in a time of corruption and decay? What are you supposed to do when power and ambition and luxury and fear begin to pull your society apart? Well, today's guest, Barry Strauss, is one of the great historians of the ancient world. He's a classicist, a military and naval historian. He's a professor emeritus at Cornell, senior fellow at the Hoover Institute.
2:16Ryan Holiday: He's written 10 books on ancient history, including his latest, Jews First Rome, Two Centuries of Rebellion Against the World's Mightiest Empire, which came up. We ran into some friends of ours in Rome who were Jewish, and we were talking about this very book as we stood on the roof of their hotel, looking down over Colosseum, the Forum, St. Peter's, talking about all of this, right? And I love this episode. This is one of my favorite episodes of the podcast. Barry and I nerded out about why the Roman Republic fell, who was better, Cicero or Cato, the decision to assassinate Caesar, which I thought about as I stood there.
2:51Ryan Holiday: I convinced my kids to go see this spot because I told them there's a colony of stray cats there, which they were very excited about. So as I was looking at the ins and outs of it, they were running around counting how many cats they could see. Talking about the rise of Octavian, aka Augustus, why a public requires debate and conversation and why democracy is never just a piece of paper. But it's about education. It's about value. It's about institution and character. This episode is going to be a crash course on Rome, but really it's a crash course on what happens when a society forgets what made it work in the first place.
3:24Ryan Holiday: And you're really going to like this episode. Barry is a bestselling author, as I said. Barry is someone whose work, if you don't start with Jews versus Rome, maybe the war that made the Roman Empire, 10 Caesars, the death of Caesar. He's got plenty to choose from. He's also got a great podcast, Antiquitas, Leaders and Legends of the Ancient World. You can follow him on Instagram at Barry Strauss. And you can grab signed copies of the new book, which he signed when he was here, Jews versus Rome. And of course, the war that made the Roman Empire. Let's get into it. It was interesting. The thing I was at yesterday, they were all very worried about the state of Western civilization.
4:02Ryan Holiday: Yes. Yes. How worried are you? About the state of Western civilization? I'm not worried. I think we face challenges, but I'm not worried. It must be interesting, though, being a historian effectively of Western civilization. Yeah. Because that's kind of what everyone's always been worried about. Yeah. You know, like, and you sort of, obviously, you know, when it was really imperiled. Right. It's not like it's a smooth, pleasant history. No.
4:34Yes, good point. There are always challenges.
4:36Ryan Holiday: Yeah. Like I was reading, have you ever read Walker Percy's The Movie Goer? Yes, but a long, long time ago. I was rereading it recently and there's this line in it where, you know, she says like, the age of Cato's is gone or something or the, you know, and or the last of the Cato's. Anyways, I was thinking about it because what was so funny to me about that is like, I mean, And Cato, it's not like he lived in a shining moment in the Roman Empire. Like he's literally the last of that, right? Like he literally watches the Republic fall. But also I just took a special humor in that Cato the Elder was concerned that the end of Rome was the introduction of philosophy.
5:17Ryan Holiday: The thing we now celebrate as the defining achievement of these civilizations. Yeah. I mean, I hate to confess it, but I'm not the world's biggest fan of Cato the Younger. Tell me why. Because I think that he didn't understand the need for compromise. Yes. And he did not have the strain of pragmatism, which was one of the things that made the Romans great. Yeah. And, you know, Caesar had a lot to do with bringing on the Civil War, but Cato had a lot to do with it as well. Yes. Do you think that he was a mediocre politician or do you think he was too principled and clean for the world of politics or is it somewhere in the middle?
5:51I lean towards too principled and clean for the world of politics, but that makes him a mediocre politician. Right. He wasn't good at the job. He thought that all the problems could go away. All they had to do was get rid of Caesar and everything would be fine. Yes. But that wasn't true. Yeah. I mean, Rome faced some fundamental problems. And the thing about the Caesars and Pompeys of this world is that although their solutions for these problems were not the solutions that were ideal, at least they recognized the problems.
6:21Ryan Holiday: Yeah. Yeah, it's like he didn't understand that actually the job of the politician is to compromise on your principles. Yes. So my big line, which I repeat ad nauseum, comes from this great novel, The Leopard. You know, it's a novel about the revolution in Sicily in 1860. And the main character is this old aristocrat who doesn't want to change. And he doesn't have any children of his own, but he's very devoted to his nephew. And his nephew comes and shocks him and says, I'm going to join the revolution. and the old guy says, how can you do that? And he says, uncle, you have to understand if we want things to stay the same, everything has to change.
6:59Ryan Holiday: Yes. This is an Italian novelist, right? Absolutely. This is Queen Elizabeth's motto. Queen Elizabeth II. You're kidding. That is her motto in the royal household that if things are going to stay the same, things are going to have to change. She was a wise woman. Yes. Yeah. I knew there was a reason I liked her, but I think that's absolutely true. I mean, it's a little bit cynical, But I think it's absolutely true. I mean, I think that what a politician has to do is to, first of all, assess his or her society and say, what are the strengths? What are the things that really what are the core values that we really have to keep?
7:32And then say, OK, but we can't have everything we want. What are the things we're going to compromise on? And we can't have everything we want because the world is always changing. And so I think that a wise politician understands that.
7:45Ryan Holiday: And isn't there also a difference, which I feel like Cato maybe failed to understand, which is the job of the politician in the doing of politics is to compromise on principles because not everyone gets what they want. But then the job of the public official is to be unswayable from their personal principles. So Cato refusing to take bribes or to decide to run the treasury, you know, honestly. Right. That's good principles. And then, hey, Pompey coming to you and proposing an alliance, even if you find him personally distasteful, if that prevents Caesar from bringing him into his clutches, that's a great compromise.
8:32I agree. Yeah. I mean, that's a really good example. And so that tells us both the strengths of Cato, what's admiral about him and the weaknesses of Cato. Yeah.
8:41Ryan Holiday: If we have Caesar on one end, Cato on the other, is Cicero in the middle? Is he getting the mean right or is he too principled or not principled enough to be a good politician? I think he's a better politician than Cato. But I think that where he fails is that he too didn't understand the impossibility of keeping the Republic the way that it was. I mean, the way I see it, here we have Rome, which is now ruling somewhat like 50 million people. And the idea that you can have a charmed circle of a few families in and around the city of Rome ruling this permanently without opening the doors to outsiders, that's a non-starter.
9:22That's a no-go. And Pompey and Caesar both understood that, whereas Cato and Cicero did not. And I think that's what's so problematic about them. Yeah.
9:35Ryan Holiday: When I read about them, I at least admire Cato, even if he's frustrating. And then with Cicero there, I always have had this sense. It's like he knew better or he could have done better. Like there's something disappointing about Cicero in a different way. You know, he's sort of always checking the wind. You wish he was more heroic. And then he just sort of, it's almost like he wastes himself on the wrong crisis. Yeah, I know what you mean. But he was not made that way. He was a man of courage and a man of principle. Certainly took a lot of courage for him to stand up to Antony the way that he did.
10:12But he was in a way he was too clever by half. And he was vain. I mean, he allowed Octavian to take him in. He thought that he was using Octavian, yet Octavian was using him. And he also made the mistake of not being able to keep his mouth shut. And the word got back to Octavian. So, I mean, what a wonderful speaker, what a fantastic orator, what eloquence and a wonderful thinker as well.
10:37Ryan Holiday: And how timeless the themes are, right? The politician who compromises too much, the politician who doesn't compromise, the ambitions getting in the way, the telling themselves that they're using the figure when actually the figure is using them. Like just the themes are torn from today's headlines. I agree. And Cicero's letters, I mean, they're my favorite. I mean, just what amazing, amazing documents they are. Yeah. Yeah. My favorite story about Cicero is I forget who it was, but some some person had just sort of performed this artistic fuck you to Caesar's face. And Cicero, you know, congratulating him after says, you know, come sit next to me, you know.
11:25Ryan Holiday: And the man says, oh, I'm surprised there's room. You always take up two stools. Meaning that he never picks a side, that he had trouble drawing the line, which obviously Cato did not. Right. But there's sort of a vice in both directions. My favorite story from Cicero is from the letter to Atticus where he describes Caesar's visit to his villa. And he says at the end, he's not the kind of guy to whom you'd say, come back again soon.
11:56Ryan Holiday: yeah in cicero at least there was a consistency for cato with the principles yes except for that whole weird thing with his wife uh yes uh but cicero seems to like the philosophy and like the the image of the stoic but then uh also really likes being rich and powerful and important right yes so maybe for people who have no idea what we're talking about walk us through to in broad strokes how it goes sideways. Why does the Republic fall and sort of who are the players there? Sure. I mean, it's a long story, first of all, as you know, and it takes about a century for the Republic to fall. Yeah. But long story short, I think it has to do with the rupture and what colleagues of mine call the civic bargain.
12:43And the civic bargain is that Roman citizens would serve in the military. They defend the country. Then they go back to their farm and they would enjoy a middle class existence on a modest sized farm. And they would also be able to participate in politics. It wasn't a democracy, but there were elections and ordinary people had a vote. And it all starts to go sideways as a result of the wars that Rome fought in the third and second centuries. The wars that really, you know, squeeze these people to the pipsqueak. Many of them die. Many of them lose their farms. At the same time, Rome is becoming a major, major slave power and Italy is becoming a slave society.
13:27And the fat cats are grabbing up all the public land that ordinary Romans would need to pasture their herds on. So we see people moving to the city of Rome because they can't make it on the farm anymore. We see people losing their farms. We see people going into debt. And the net net, it just really affects the Roman military because the Romans staunchly believed that you could not arm poor people because if you armed poor people, they could turn on you. And they also thought that poor people were poor. I mean, unfairly, they thought that poor people were poor because they lacked virtue and they just didn't have the right stuff.
14:04Yeah. So suddenly there's not enough people who can meet the military, the property qualification to go into the military. And two Roman politicians, the Gracchi brothers, try to do something about it by redistributing public land and getting the wealthy to give up this land and to share it with the poor so that you can bring potential Roman soldiers back up to speed where they can meet the property qualification.
14:30Ryan Holiday: The first moral panic about socialism. Yes. Yeah. In a way, yes, you could say that. So this leads to a violent opposition. I mean, literally violent opposition. And there are lynch squads put together by senators to kill each of these brothers in turn and to make these reforms moribund. They were also afraid, the old guard was afraid that as a result of this, that the Gracchi brothers would have unassailable political popularity. So Rome's in a dither about what to do, or in a tizzy about what to do. And ultimately, when they face a challenge from Celtic invaders at the end of the second century, or they also have a crisis in the war in North Africa, what they're forced to do, they constantly have to lower the property qualification, accepting poorer and poorer men into the military.
15:27And finally, I say, no more property qualification. Any citizen can become a Roman soldier. And so you have these poor people who go in the military and their commanders say, you know, fight for me, fight for Rome. And they're saying, well, why? And they're saying, because at the end of the rainbow, there will be a pot of gold. And the pot of gold will be that I will get you land.
15:51Ryan Holiday: They would settle the soldiers in these different kind of colonies and areas that they'd conquered, right? Eventually. Yeah. But not quite yet. in this period, they're settling them in Italy, which means they have to get land for them, and which often means they have to take land away from somebody else. So they're sowing the seeds for civil war. And what's happening is now ordinary Romans, instead of being loyal to S.P. Cugar, instead of being loyal to Senatus Publisque Romanus, the Senate and the Roman people, they're now loyal to their commander. I'm Marius's guy. I'm Sulla's guy. So they're not really loyal to the republic per se anymore, but to the guy who represents the republic to them.
16:34So citizenship has really changed its meaning, and Rome is in danger of becoming a military dictatorship. So as you know, there's a long and complicated civil war, a set of civil wars between Marius and Sulla, and when Marius dies, between his partisans, Sulla and Sulla wins. very brutal war. He is on the side of the conservatives, the old guard, the people who call themselves the best men, whereas the other side of the people who call themselves the men of the people. We might call them populists. It's a little misleading, but it's close to what they are. And Sulla comes in and makes himself dictator, kind of twisting the meaning of an old Roman an institution that's supposed to be temporary.
17:21He's dictator without any time limit on it. And he reforms the constitution to try to turn the clock back before you had all these populists to try to make Rome back to the conservative way it was before. But he steps down after a year, probably he was ill because he dies shortly after that. And the Republic is back in business, but slowly it devolves into what it had been.
17:47Ryan Holiday: And this gets us, because Sola and Cato overlap, right? So like Cato's a young boy during Sola's reign. So is Caesar. So is Caesar. Yes, right. And so is Pompey. So we're now in the 70s. Yeah. We're now in the 70s BC. So here's the Republic and it's very lively. There's a lot of debates. It's very active, but there's also a lot of tension because the Republic is depending on these big guys, the big men, who are going to represent Pompey and Caesar come to the fore. There's also a third one, as you know, Crassus, who also wants to be one of the big boys and one of the great military leaders. And the other thing that we have to factor in is that in a way, success has spoiled Rome.
18:29And the old-fashioned Romans who were afraid of the Senate and who respected the power of the Senate are being replaced by new generations who think, you know, I'm really hot stuff and I should be ruling the world. So you get that with Pompey, you get that with Caesar. Crassus would have liked to do that, but he fails, of course. And that's part of the story as well. These are people who don't respect the old rules. Rules are for suckers.
18:59Ryan Holiday: The institutions are slow and ineffective and holding us back. And don't you know how great I am? So there's part of that as well. So on the one hand, it's a society that's still playing by the old rules. But on the other hand, there are people who won't play by these old rules. They're populists as well who are, you know, roiling the system. They're wiling things up. There's a lot of tensions going on. I mean, scholars disagree. I mean, one of the great scholars of Rome, Eric Gruen, argues that the Republic could have survived just fine. It was assassinated. You know, it did not commit suicide.
19:36It was assassinated. And it could have gone on. I think it could have gone on, but only if it had been willing to make compromises with reality. And in the end, it wasn't willing to make those compromises with reality. In fairness, it was really being pushed to the limit by Pompey and Caesar.
19:55Ryan Holiday: It's like they're driving a car too fast and it's starting to shake under because it's hitting up against the limits of what it's capable of withstanding. Absolutely. Yeah. Absolutely. And so it's unclear how they're going to solve this problem. And in the end, led by Cato, they say, we're going to solve this problem by going for the jugular. We're going to get Caesar. You know, we're going to strip him of his command in Gaul. We're going to put him on trial. And he's going to be condemned to death. So what he's going to do is he's going to go into exile. And that'll be the end of him, end of problem.
20:32Ryan Holiday: Get rid of the guy who's putting the most pressure and strain on the system. That's right. Bumping up against its limits. Yes. And then things can all go back to normal. That's right. And in the meantime, Pompey, who was allied with Caesar for a while, realizes that his star is going into eclipse and Caesar's is rising. And he decides, what do you know? I was a conservative after all. Who knew? So now I'm on the side of the Senate and I will fight Caesar on their behalf. Yeah.
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23:39Ryan Holiday: So a couple of things I'm taking from your version of this story. Number one, you know, we go like the fall of the Republic and we think about it as like Caesar, Cato, Pompey, whatever. But like, first off, you're dating it back almost 100 plus years. And then and then this isn't getting into sometimes people conflate the fall of the Republic with the fall of Rome itself, which is hundreds of years after that. Yes. I think there's a there's a common thread, by the way, between the two of them. But yes, it's 100 years after that. And the common thread is just compressing an immensely complicated bit of history down into a single thing?
24:15Ryan Holiday: Or what's the thread? I think the thread is citizenship. I mean, I think the thing about republics is almost what Churchill said about democracy. It's the worst form of government except every other form of government. Republics have this, have debate. They have citizen activists. They are unruly. but they're also incredibly good at mobilizing the people behind a cause when you have politicians who know how to do that. It breaks down in the Republic, but by the time you get to the later Roman Empire, citizenship has, it hardly exists. The Senate doesn't really do anything anymore. It doesn't have any real power.
24:56There haven't been assemblies for a very long time. The people of Italy live a privileged life. After around the year 200, there are no soldiers who come from Italy anymore. All the soldiering is being done by people from the frontier provinces. And it doesn't mean they're bad or disloyal to Rome. It just means there's no way to mobilize the citizenry. There's no way to turn the ship around very easily. And so Rome is at the mercy of a few leaders and unable to make the kind of changes that would have been needed, that would have been very difficult, but not impossible to keep the empire going.
25:34Ryan Holiday: So I also wonder, like, from there's obviously there's sort of the systemic explanation of history, economic causes, historical forces, et cetera. And then there's the sort of great man of history theory, which is like individuals are responsible. Everything would have been different if this person didn't exist. Yeah. What's interesting about the fall of the Republic is it's kind of those two things intersecting with each other. They intersect. It's like the answer is both. This is the Strauss version of history. Yeah. It's messy. There's not just one answer. Yeah. Society and economics matter.
26:07Culture matters. But individuals matter as well. You know, if you hadn't had Caesar and then if you hadn't had the incredibly cunning, clever, unscrupulous, ruthless, murderous, but visionary Octavian. You know, it wouldn't have ended up as the way it ended up, but it might have ended up as an Egyptian empire, which could have been totally different.
26:29Ryan Holiday: Yeah. Or the events and the trends give rise to the opportunity to the individual. And then the individual has the choice. Are they going to be a Caesar or a Cincinnatus? That's right. And it was this kind of convergence of right man, right time or wrong man, wrong time. And that's what changes the arc of history. Yeah. I mean, I think if you look at the founding, if you look at the American independence, how amazing that was. I wouldn't say it was totally unexpected. The British foreign office or whatever, the colonial office, whatever it's called at the time, certainly had totally the idea, gee, if we defeat the French, that'll be great.
27:06But there's one problem. The colonies won't need us anymore. Still, the fact that the rebels were able to pull this off is kind of amazing.
27:14Ryan Holiday: And then that Washington makes the choices that he makes. He could have fought a more traditional war. That would have been different. He also could have decided to make himself king or any number of the founders could have decided to go in a different direction. And it's this remarkable set of choices. And they had the benefit of obviously looking back at the previous choices and going, hey, how did it go last time? Yeah. Washington, of course, was a huge fan of Cato, but the Cato that he loved was the Cato of Addison's play from the early 18th century. It was not really the real Cato, not the historical Cato.
27:50So it was imaginary Cato.
27:51Ryan Holiday: He's Lin-Manuel Miranda's Hamilton, not actual Hamilton. Yes, exactly. Yeah. Imagine if our leaders used the Broadway version of Hamilton. Yes. They could be worse things. No, in a way, it's perfect, right? I mean, he is a tragic figure in the play, but it's a play celebrating primarily the virtues of the person. It is. And the Addison version of Cato is the virtues of Cato, not the frustrating, obnoxious, ineffective version of Cato. Yes, yes, absolutely. And yeah, they make these choices and then it works out the way that it does, but it always could have gone otherwise. Absolutely. History is contingent.
28:31Yes.
28:32Ryan Holiday: Are there a handful of choices when you look at the fall of the Republic that you go, man, that was really a pivot point? Or you're like, I really hoped he would go in this direction? Or is there anything that stands out at you? Well, certainly, of course, the most famous one is the crossing of the Rubicon. Yes. You know, the fact that Caesar decides to start a civil war rather than giving in, you know, a less determined and less selfish person might have said, look, you know, I love myself, but I love my republic country more. And I don't want to put the republic through this. Caesar doesn't say that.
29:07Right.
29:07Ryan Holiday: You know, he could have been more of a MacArthur figure who was done an injustice in some. I mean, sort of deserved to get fired in my view, but like he could have crossed, when MacArthur is called back from Korea, he could have made himself a more Caesar-esque figure than he did. Yeah. I mean, William Manchester wrote this book, I think, American Caesar. We have it in the bookstore next door, yes. It's a really interesting book, but in the end, he wasn't a Caesar. Right. He makes the choice. Yeah, he makes the choice. Caesar decides differently. You know, he says famously, my dignitas is dearer to me than life itself.
29:42My dignity, my rank, my status. I mean, that's a very un-American thing to say, but it's a very Roman thing to say. Yeah. Although an American might say my reputation is the most, I live or die on my reputation.
29:55Ryan Holiday: Yeah. Quite the same thing. But sort of built into the American story up until relatively recently was always country over self. Yes. Right. And that was a powerful norm that saved us in some narrow run moments. Yes. And I don't want to get off topic, but we could talk about why we don't have that anymore. Yeah. Okay. I mean, I think the Romans and Greeks would have said, it's very simple. Success spoiled America. Luxury. The Russians believe that luxury was the greatest enemy of republics and that to have a republic, you need to have just a little bit of want, desire, need. You got to keep people hungry.
30:40And you got to have people, you can't have people thinking the most important thing in life is getting rich and being able to afford$7 lattes every morning.
30:50Ryan Holiday: Don't you think part of it is also though, like, and this is why Cato the Elder was concerned and K to the Younger was concerned, which is like the norms persist as long as people continue to believe in them and the story is told and retold and each subsequent generation is inspired and steeped in the conditions that make the norm logical and celebratory. Yes, but you have to educate people. Yeah, that's what I mean. You lose the ability to do that, perhaps in prosperity, but also because you so take it for granted that everyone understands. You take it for granted. So when I was growing up during Vietnam, people would sneer at patriotism.
31:35I'm not saying we had to support the Vietnam War, but I think that people went beyond that and say there's just something wrong with being a super patriot, as they would have said. And that can lead people too far in the other direction and just challenging everything.
31:50Ryan Holiday: When it's a feedback loop, right? Because you start to question the idea of patriotism exactly at the moment that your government is proving itself to be not worthy of the trust or faith. And then it's this downward spiral that they experienced in Rome too. Yes, absolutely. I mean, you have to give citizens, you have to fulfill your part of the bargain and give citizens the thought that this is the way to go. It's something they should love, but there's a reason why they should love it. It's hard to sell to people, even if it doesn't work for you, you should still love it, which is true, but it's hard to get people to see that.
32:29Ryan Holiday: You should fight in the war that even your average citizen sees is a bad idea and not going well. Yeah. Because that's, but that is the Roman way. Like there was this kind of unquestioned obedience. I think of that story, I forget who it was. What's the famous Roman myth of like the hole opens up in the ground and Rome will only be saved if its most valuable things are thrown into it. and that Roman gets on his horse and he dives into the hole. Do you know this myth? Vaguely, I'm afraid I'm drawing a bit of a blank. But the point is, unquestionably, I'll kill myself to save Rome. Well, Decius Muse, I mean, he's the guy who engages in self-sacrifice for the sake of Rome.
33:13Yes. I mean, yes, that is a Roman story that the Romans told themselves, and they had to believe that it was worth doing that for their society. You know, the other thing about it is it's easier in a way when you have an external enemy and you feel that you have to make sacrifices because of the cause. I mean, I think one of the things about the Cold War and even more after the Cold War was we felt we weren't really at risk. I mean, I think maybe people felt in the 50s they were, but as things started to calm down a bit, I think less and less people thought, no one's going to start a nuclear war.
33:48We're not really at risk. And then after the Cold War, we thought, oh, we're number one. Yeah. You know, it's a unipolar moment, as they say.
33:56Ryan Holiday: Well, and then also, I mean, this is getting a little too modern, but like the idea of an existential godless enemy. Right. Did, I think, bind the sort of conservative movement into the sort of, well, we're not going to be opposed to everything. We do understand there are some things more important. Like it kind of brought everyone on this team of like, hey, yes, we at least agree on foreign policy that we all hate the Russians. Yeah. Or the Soviets. Yeah. And I mean, I think many, many liberals felt the same way. You know, they said they're not we're not down with conservatism, but we don't want communism.
34:32Ryan Holiday: Yeah. So another pivot point that I think a lot about, again, stoicism is at the center. The decision to assassinate Caesar. Yes. We have. Yes. We have Brutus. Right. We have Cato's daughter. yes so obviously there's the decision to do it which is a pivot point right but then there's also this sort of it strikes me as similarly naive in that they just thought we'll strike at the king right and then the movement evaporates like there was effectively no plan as to the day after yes they did not i think they underestimated the military they had thought it through some and they thought that, you know, what we need to do is to say to Caesar's soldiers, we know Caesar has given you this enormous amount of wealth.
35:19He's rewarded with the enormous amount of wealth and you can keep it. But what they didn't realize is that in order to win over Caesar's soldiers, they need to say, and we're doubling it. We're giving you more, which in fact is exactly what Octavian does a bit later. That was their mistake. I mean, just think of, I imagine this assembly a few days after the assassination where Brutus is addressing the crowd and he says, you guys don't have to worry. You can keep what Caesar promised you. Imagine them thinking, that's it? We want more. You killed our leader. We've got to pay. You've got to pay up.
35:51Ryan Holiday: They knew they were in the catbird seat and that they were the swing vote. Yes, they were the swing vote. And it was just a matter of a leader arising who could organize them. In the end, two leaders arise, Antony and Octavian. and Octavian just turns out to be infinitely more cunning and ruthless than Antony. Not that Antony was a slouch. He wasn't. Yeah. But Octavian could outfight him. And he wanted it more, don't you think? Yeah, I think he wanted it more, but he was willing to just do sleazy stuff more than Antony was. I just meant Antony wanted to party a little bit. Yes. But remember, we're only getting the version that Octavian wants us to have.
36:39Because Antony didn't live to tell his side of the story. Sure. So the version we get was this guy was just a drunkard, you know. But I'm confident that the real Antony had a lot more on the balls on that.
36:51Ryan Holiday: Yeah, he's obviously very savvy and adapt and driven and ambitious. But he does tarry there in Egypt for a bit in a way that I don't know if Octavian would have. Again, we're getting Octavian's version of the story. I mean, Cleopatra is not just, you know, a fabulous lover. She also is herself. She's a very cunning strategist and she's the richest person in the world. Right. So, and she has access to all the savvy of the Ptolemae kingdom when it comes to naval stuff in particular. Right. So there's a lot of reasons to want to be with Cleopatra. And also finally, she's Caesar's girlfriend. Right.
37:30She's Caesar's woman.
37:31Ryan Holiday: That's the link to the past. She's the link. And also she comes from the family of Alexander the Great's general. I mean, it's tremendous propaganda, PR advantage for being with her. She's also a goddess. She's Isis on earth. And as her consort, Antony is Osiris. And he's also, she's Aphrodite and he's Dionysus. And we might think, oh, who cared about that? But they did in the ancient world. They really did. It's like finding out you could be Pope or something. Like in addition to a head of state, which is like, wow. Yeah. Yeah. So, yes, he did tarry in Egypt some, but again, we're getting this propaganda from Octavian Augustus is one of the masters of propaganda in all of history, you know.
38:15Ryan Holiday: So as far as lessons, okay, so citizenship matters. The bargain with your people matters. Obviously, the individual choices and the character of the leaders matters. Yes. Any other big lessons you feel like we draw from this story? Well, the economy matters. You know, it's the economy, stupid. You know, one of the things that I hear from young people all the time nowadays is we can't have the American dream. Yeah. You selfish baby boomers took all the money and we can't have it. We can't. We can't buy a house. We're not going to be. We can't have kids because it's just too expensive. Sure. Also, you wreck the environment.
38:52Ryan Holiday: You wreck the environment. Everything is a mess. And you're expecting us. That goes back to the bargain, right? Everything's a mess. And you're expecting us to play by the rules and have faith. And that's looking like a bad bet. It's looking like a bad bet. Plus, we have to spend all this money to go to college and then we come out and we can't have a job because it turns out that all the stuff we were promised with a college degree turns out to not be true, as you know very well. So they have a point. They absolutely have a point. So, I mean, when you have a system that's due for change, the question is going to be, well, is it going to have to be violent change?
39:29You don't want it to be violent change. How can you evolve the system? How can you make changes in the system? So I would say we want to throw into the hopper compromise. Compromise being a value. And I think that's really important in republics because republics depend on debate and they depend on people vigorously disagreeing with each other. But it can go overboard.
39:51Ryan Holiday: Isn't that the genius of, say, like an FDR in that there is a moment it's clear the thing is not working. It's clear the bargain has gone bad. And then there are the people for whom, you know, the system has worked or they are really principled in the sense that they believe in, hey, this is what the founders wanted. Sometimes it goes like this and they don't want to change. Right. And he says, sorry, guys, it's this or revolution. Yeah. And he figures out how to change within the system without violence. Yes. And sort of mitigate some of those. Yes, it is the genius of FDR. And I would say even more so the genius of Lincoln.
40:30Yes. You know, the ability to compromise, but also understand there's some things you can't compromise. Right. So, you know, getting that right and then keeping your head and keeping together during this terrible, terrible crisis. I mean.
40:45Ryan Holiday: Right. Yeah, it is interesting with both FDR and Lincoln, they could have been a Caesar figure. And there were people who accused them of being that at the time. Right. And obviously they both shattered norms, whether you're talking about habeas corpus with Lincoln or you're talking about the decision to run for a third and then a fourth term with FDR. But it was within some self-imposed limits. It was. It was within some self-imposed limits. Absolutely. Yeah. Although maybe Caesar would have said, hey, I could have gone further. I chose to stop here. And then you stopped me before I was able to sort of turn this thing around.
41:24Ryan Holiday: Becoming dictator in perpetuity is pretty far. Sure, sure, sure, sure. But it is interesting how at some level it ultimately does come down to the character of the person who finds themselves in that moment and what they're willing to do and not willing to do, what they believe and what they don't believe. I mean, Caesar did not have to bed the queen of Egypt and produce the next king of Egypt as his illegitimate son. And he did not have to tolerate her being stashed in his villa on the other side of the Diber River while he was living with his wife in downtown Rome. I mean, that I think is one of the untold reasons.
42:00It's an unsung story because it's not in Shakespeare for the assassination. But that made the Romans very nervous. It made the Romans very, very nervous. Yeah. Very, very nervous.
42:10Ryan Holiday: Yeah, I think it's so interesting. Again, the Stoics not being pragmatic, but the first thing is it's either Athenodorus or Aristidimus. I forget, one of the teachers of Caesar, or sorry, of Octavian, he goes, you know, one cannot have too many Caesars. and that's the you know the indirect way of saying you got to get rid of Caesarean and so there was the Stoics do learn a little bit late that you know power requires a certain amount of ruthlessness and pragmatism Caesar of course was an Epicurean and sort of got along with the others but at some level you know he probably thought Cato was a sucker at some level.
42:59I think so. Yeah. You know, Caesar is quoted as saying, we don't know if he really said it or not because it came from an enemy. The Republic is a mere name, all form without substance.
43:13Ryan Holiday: Yeah, there's, I mean, at the center of Caesar is Caesar. Yes. And at the center of Cato is these principles and ideals and something more abstract and theoretical. Yes, but let me defend Caesar a little bit. I mean, Caesar really does believe in the Roman people and both in the rights of the Roman people and also in taking care of the Roman people and making sure they had prosperity. I mean, there's an Italian scholar who wrote a book called Caesar the Democratic Dictator. And I think that's going too far. I don't think he's a Democrat, but he did care about the people in the way that a Cato did not, really.
43:56Ryan Holiday: Yeah, that is something that you find both in the ancient world and in the modern world. There is this, okay, sure, the principle is important. You are right, but people are starving in the streets. And if the government is failing to do its job, it doesn't matter that... I think Lincoln said this. He's like, the Constitution is not a suicide pact. OK, you know, like like you can't expect me to stay true to these things if it means people can just leave the compact of states at any time or whatever. Yeah. And Cato, I think I mean, he does famously commit suicide. He probably didn't have a problem with principles being a suicide pact.
44:33Ryan Holiday: I think he kind of thought at some level thought that was the highest expression of their value. Yeah, I think that's true. And he was ahead of his time because suicide hadn't become as highly regarded as it would be in the next century under the Stoics. Yeah, it's highly regarded. No, but it was a dramatic act of devotion, he thought, not cowardice or weakness, but like it was like the monk in Vietnam lighting himself on fire. It's funny. I'm reviewing a book about Carthage, and I realized that one of the things we remember about Carthaginians is the ones who committed suicide, like Hannibal and Dido.
45:12Ryan Holiday: Yeah. I was reading Andrew Roberts' biography of Napoleon a few years ago, and he has this great section, which came out, where Napoleon is just shitting on Cato. He's like, you know, Cato, he committed suicide, and who did it help? Caesar. What did it accomplish? Nothing. You know, and like on the one level, he's right. And then on the other level, you're like, well, of course, Napoleon doesn't understand. Napoleon is a Caesar. Of course, he doesn't respect a Cato. Yes, absolutely. It's almost like these figures are just speaking totally different languages and they can't understand each other.
45:48Ryan Holiday: And they think the other one is the crazy person. I think that's true. Yeah. And ideally, you have the purpose of institutions, I guess. And this is what the founders, I think, did well, although it's clearly under strain these days is like, how do you create systems or structures that channel some of that energy and allow it to dissipate, you know, and we've managed to head it off for 250 years, but the pressures remain. Yeah. And you're absolutely right. And the thing about institutions, though, is that you need to have the societal underpinnings that make them work and that make people say, yes, this is the right way to do things.
46:28If it's just a piece of paper, it doesn't mean anything. I mean, John Adams famously said, our constitution will only work for religious people. It's not suitable for anyone else. And maybe we could substitute religion for principles.
46:42Ryan Holiday: He means like, yeah, because it is funny because I was just reading something the other day where he was reassuring in that treaty against the Tripoli pirates or whatever. He was like, we're not going to wage a war against the Muslims because we're not, we're by no means a Christian nation. Right. How interesting. So he said that, but I think his point is the constitution only works. And he said this more explicitly somewhere else, like if the people are virtuous. Yes. Yes. Absolutely. Yeah. And, you know, the constitution doesn't say much about that. And it was left to the states and it does tell some of the state constitutions do talk about that.
47:16Ryan Holiday: Yeah. But education is an unspoken thing. Yeah. And it's enormously important. Tocqueville, of course, does talk about that more and does get it. Yeah. That you don't have democracy in America because you have a piece of paper. You have democracy in America because it lives in people's hearts. And it lives in their hearts because that's their way of life. So, I mean, I think that is a challenge for us today is it is in any generation. You can't rest on your laurels. You have to come up with mores. Yes.
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50:36Ryan Holiday: Well, you also, I think we're realizing today just how as explicit as the Constitution is, and then they made it more explicit with the Bill of Rights, that it is primarily a system of government centered around a bunch of unwritten norms. Like it's more British than we thought it was. That's a good way to put it. And then it's very hard to continue those norms if you get to a point where suddenly everyone there, what's that thing, the Chesterton fence thing where it's like, we don't know why the fence is here. Like, we don't know what, why is there a norm that this can't happen or that can't happen?
51:11Ryan Holiday: Why does the president have to voluntarily leave after two terms? Like all these norms, like the pardon power was, obviously you can't pardon yourself and you can't preemptively pardon people for crimes they haven't committed. And you can't dangle pardons in front of people for committing crimes. That's not explicitly set out anywhere, but George Washington would have barely conceived of someone conceiving of doing such a thing. Right. I agree with you. But you can't enforce norms by saying, we're going to enforce norms, darn it. It's really got to be in people's hearts, and they have to be educated this way.
51:47I mean, Aristotle talks about the importance of habit and habituating people in education. And I think that's just so important. I think one of the reasons our society's in the trouble it's in today is because of the educational system. Yeah. And the way we don't raise people, the things we do teach them and the things we don't teach them.
52:06Ryan Holiday: Yeah. And the way it was for the founders is they're so steeped in the stories that the characters that you write about in the books, not just like they're signing the Federalist papers with their fake Roman names. Right. But like if you had called someone a Catiline or whatever, they'd all have known. And then if you If you call Trump a Catalan, like what percentage of the population is like, what are you talking about? Yeah. You know? I know. They just don't. It's like we're only able to say someone's like a Hitler or Martin Luther King. Like we have like five people we can name. We don't have the sort of historical narrative that is so rooted in why we have certain systems and what certain norms are.
52:46Well, Americans have often devalued history. I mean, it's not an accident that it was Henry Ford who said history is bunk. I mean, you know, Americans live for the present and live for the future. We don't really live in the past, but we need to study history. I mean, we really do.
53:03Ryan Holiday: It was funny. So this thing I was at yesterday, the guy was talking about he'd taken his kids to New York City and they were at this museum. They were looking at all these classical sculptures and history. And that was all very impressive. And then they went to this play and it was full of woke garbage, you know, or what he was ranting about this. you know, there was transgenderism. And I was like, okay, first off, the Romans that you're celebrating, they had a lot of sex with guys. I think you'd be horrified at what Roman culture, Greek culture was actually like, but that's neither here nor there.
53:35Ryan Holiday: There is this sense that those civilizational values are in retreat or decay. And what do you think you do about it? What do you do about it? I think you have to, I mean, I'm very platonic about this. I mean, And I think you have to educate the young. I mean, you're not going to have the society you want unless you educate the young in the way that they need to be educated. And, you know, Plato gets that 100 % right. So I think that's what we have to do. I mean, that's my job as an educator to think about how we're going to educate young people. What are the stories we're going to tell them? What are the books we're going to have them read?
54:10What are the ideas that we want them to have? What are the practices we want them to engage in? And I think as a society, we've been kind of laissez-faire about this and not taking it as seriously as we need to do. You know, the American thing, those who can do, those who can't teach. I mean, OK, yeah, I get it to a degree, but those teachers are really important. And what we teach our kids and how we teach our kids is one of the most important things that we can do.
54:43Ryan Holiday: When it's like this STEM stuff is really important, right? It is. And at the same time, if you go, no, get an engineering degree or you got to learn how to do something that'll help you get a job. What are you studying? A bunch of it's like the humanities and these stories got taken out by both ends. It's like this isn't practical. I'm not paying you to go to school to be a philosopher. And then also it's just a bunch of old dead white guys who were slave owners. Screw them. What can they teach us? And so we end up cutting down our sort of shared consensus and understanding of those values in both directions.
55:19Ryan Holiday: And then we're like, why don't people believe in this stuff anymore? It's not they don't believe it. They don't even know it. They don't even know it. Yes, they don't even know it. And that's the problem. We really have to put it back on the agenda that young people are learning about this and tackling these ideas and thinking they're important. And I mean, so I'm visiting the School of Civic Leadership at Texas. And one of the things I like is the fact that you can do a minor, I don't know what they call it, but taking, I believe it's six courses in civic leadership. And they've got engineers who are doing this.
55:50I think that's great. You know, I think that's the kind of thing that we need to be doing in our universities. And we have to say to people, you really do have to read the great books. Yes. And you really do have to join the great debate and be part of the great ideas. Of course, you can be an engineer. We need more engineers, in fact. But we also want you to have some sense of this. And of course, it's almost too late if it just starts in university.
56:15Ryan Holiday: Yeah, I was just going to say, you know, my nine-year-old's obsessed with Greek history. And, you know, we're having these discussions about the Odyssey. Should Odysseus have done this? Fabulous. Was it right to not tell the men as they're going through Scylla and Turbitus that six of them are going to die? Or, you know, should he have shouted out who he was to Polyphemus? And you're talking about these things and you realize, like, did the Greeks and the Romans really think Odysseus was real and that this happened? I don't know. And I would suspect no. I think they knew that this is all myth.
56:44Ryan Holiday: But the purpose of history to them was not always to be factually correct in the way that we have to root everything in primary sources. Like, Plutarch's a great biographer, even though he's not super accurate, because he's getting to the essence of these figures. You know, he's not bad, by the way, as a historical source. You can't really trust any of the speeches that he gives because ancient historians didn't think it was their job to tell what people really said is what they should have said. It's not like he had a recording. No. But I think he's not bad on historical facts. But whether they believed in their myth or not, even Aristotle quotes the Iliad.
57:17Yes.
57:18Ryan Holiday: But I mean, the primary purpose of that history was to teach the value, not even the values, but to bring up the moral debates that the incidents in the story forces to wrestle with. And the idea of, yes, Caesar crossing the Rubicon is both a historical event and then a moral question for all of us in our own Rubicons. And that's what you would study and debate and talk about. Right. Yes. Yes. It's not just a saying, the dais cast. Like, it's not just this little historical fact that you get quizzed on. And then, yeah, now with AI or whatever, it's like the purpose isn't to have ChatGBT write you an essay on whether Caesar should have done this or that.
58:04Ryan Holiday: It's to really sit down and think about what you think about whether he should have done this or that. That's why most of us in the academic business don't assign essays anymore. Really? Yeah, we know the students can get it from ChatGBT. So we either have them write blue books or we - In the room? In the room. Yeah. Or we give them oral exams. I did both. I taught with a colleague last quarter. Stanford and Hoover has this great program called the Stanford Civics Initiative. Yeah. And so we taught this course on classical leadership, which was just wonderful. And the students were out of this world, but they had one blue book exam and they had one oral exam.
58:40Right. And, you know, I think you need to do stuff like that, unfortunately, in the age of AI until we figure out this AI thing and come up with new ways to test people. Yeah.
58:49Ryan Holiday: Although, you know, we've been my my son will be like, I have this question, you know why? He was like, why? If Odysseus's father is still alive. Right. Why didn't he just step in temporarily as king? Like and I was like, I never thought about that. Like the whole thing is she's weaving this funeral shroud for a guy that's still alive. Seems like it would solve the king problem. But he's too old and weak. That's the problem. Right. But it was like, OK, let's have chat GPT tell us what are the five perspectives on that thing? Because I'm not currently in a university. I can't call you. Right. You know, but it is interesting that like these tools can maybe enable us to continue thinking about these questions from different angles.
59:30Ryan Holiday: But it can't do the questioning for us. No, it can't. I mean, it's they're limited. And as you know, they make big mistakes. They make a lot of shit up, too. Yeah, they do. Hallucinations. I, for instance, I was doing a paper about a 19th century American's use of classical oratory. And I thought, what about Frederick Douglass? I don't think he used Greek and Roman oratory, but maybe he did. So I asked Chappie GPT and it told me this whole story. And I thought, could you give me some quotations, please? And a few minutes later, it said, no, actually, I think I was wrong. I don't have any quotations for you.
1:00:00I don't think he actually said those things at all.
1:00:02Ryan Holiday: But isn't that the real skill? Like, I've been thinking a lot about this, right? Because it is this kind of, it seems like it's this magical tool, which does have access to ungodly amounts of information. It does. And so really the ability to use it is one, can you type a good question? Yes. And like, do you have the ability to ask insightful questions and curiosity? But then do you have a good bullshit detector? You had to know enough about Frederick Douglass. I did. To push back on the answer. Absolutely. So you can't trust it, but the more you know, the better off you are. So I also use these things to tell me about all sorts of things I don't know about.
1:00:39For instance, I commute by bike and I wanted to get a good summer biking vest. And so I asked it, so what are the best ones? And it gave me some, some I'd never heard of these companies and I had to look them up and I emailed some of them and whatnot. In the end, I got something really good. And it was thanks to AI that I did, but not simply because of AI. It's because I pushed back and said, OK, what about this?
1:01:03Ryan Holiday: Yeah, there's a yeah. And it's it's also like I'm doing this book on Stockdale right now. Oh, cool. And by the way, talk about being introduced to the classics, like his introduction to to philosophy with Professor Rhinelander at Stanford changes the course of his life. Well, at the Hoover Institute. And anyways, like I'm writing about this. there's this video of this, the survival school that he goes to. And I, I loaded into chat GPT and I go, tell me all the plants that are appearing in this video. So I don't have to call a plant expert and verify each one. And it does. And then, you know, it gives me the list.
1:01:39Ryan Holiday: And then I cross-reference that list against, you know, another list of plants indigenous to San Diego. I go, okay, it's saying this is here, but that actually can't. But the interesting thing is like if you've ever worked with researchers or in your case, grad students, you can never trust what people give you, period. You always have to push back. So in a way, it's actually familiarizing people with a skill set that only a small percentage of the population had to have before, which is how do you scale your brain and research? You know, you can have people go track stuff down for you, but one, you have to have a vague sense of where stuff is.
1:02:16Ryan Holiday: And you have to have a good sense of what's too good to be true or not. I think that it's maybe a reason why you still want to have people do old fashioned library research. Totally. Yeah. You know, where they have to, they get into the weeds and have to find their own way out of it, which I think will then help them in dealing with AI. Yeah. And also serendipity and some stuff is not everything is digitized. Yes. You know, not everything is digitized. And a lot of the stuff that's a lot of AI is getting a lot of this information from questionable sources. Yes. It's waiting a book in a library and some random blog posts.
1:02:50Ryan Holiday: That's right. Or, you know, Wikipedia, which can be wonderful, but sometimes it's not so wonderful. Right. So, you know, it's questionable sometimes. No, I'm trying to teach my kids this. Just the other day, we found a quarter on the ground and it was this quarter I'd never seen. So I said, let's ask chat GBT what kind of quarter this is. You know, it goes, actually, you're not holding a quarter. You're holding a penny. And I go, I'm pretty sure there's a fucking quarter. Okay. It's definitely a quarter. Let me show you. But no, no, that's a that's definitely a penny after three or four back and forth of it gaslighting me about whether this is a quarter or a penny or not.
1:03:20Ryan Holiday: I finally get it to understand it's a quarter. And then it promptly tells me, oh, it's this. That's a quarter with Eleanor Roosevelt on. I don't think it is. And then finally, it does kick out a list of some quarter that some series the Mint had done with female figures on them. And then I was able to myself deduce which one it was. Who was it? But it was this Mexican-American activist whose name I'm forgetting, and I don't want to butcher by guessing. But it was like me and this idiot figured it out together, you know, or me and this liar figured it out together. But it took the handful of rounds and not accepting the first answer.
1:03:58Ryan Holiday: In a way, it was kind of a good exercise in my kids. It's like, hey, you just can't trust the first thing that it kicks back. And then each time it's like, great job by pushing back. You know, it's like, it's also trying to flatter you. You know what it reminds me of? Socrates. How easily it'll change positions and kind of challenge you. Yeah. Or not challenge you, but it's sort of working you along. Well, you know, he compared himself to a stingray and also to a horsefly who's, you know, constantly stinging. What do flies do? But bugging this horse. You know, maybe that's what we all have to be when it comes to AI.
1:04:36Ryan Holiday: Yeah. I have a joke in the book I just. it on wisdom where I was like, for someone so smart, sort of seems like a misreading of the situation to tell the Athenian people that you're a horsefly because people don't like flies. Like, what do they do with flies? They kill them. And so, of course, ultimately, that's what they did. You'd think you would have picked something maybe more beloved. Oh, yeah. That's a great question. And one of the things about Socrates is, did he want to die? Yes. You know? Did he want to make himself a martyr for philosophy? Also, there's no, I mean, people don't like spiders or whatever.
1:05:10Ryan Holiday: And you're like, hey, but they're eating mosquitoes and bugs or whatever. You know, there's not much purpose to a fly. Like, I don't think a fly has a positive, obviously, every species has some role in the ecosystem. But it's also illustrative that the thing that Socrates would pick would be a bug of very little societal value. And he compares the people of Athens to a big, dumb horse. I mean, that's not great. Well, you know, that's why one of the reasons why Erasmus famously says, pray for us, St. Socrates. He thought that Socrates was a saintly figure who made himself a martyr on purpose. Macaulay, I think, said, the more I read about Socrates, the more I understand why they killed him.
1:05:55Ryan Holiday: I think that gets closer to it, too. Well, definitely. I mean, you know, he was working hand in glove with the people who became oligarchs. And, you know, and the story that he tells the story or I forget where it is. I think it's in the apology that the 30, the oligarch sent him to arrest Leon of Salamis, who they want to bring in and kill and confiscate his property. And Socrates is proud of the fact that he refuses to do it. He just goes home. But as a colleague of mine once said, if Socrates were really great, he would have gone and warned Leon of Salamis. And he doesn't do that. Yes. He's a complicated figure.
1:06:35Absolutely. Yes.
1:06:37Ryan Holiday: Well, this has been lovely. I had a question specifically about this book because someone asked me the other day. I was talking about Stoicism. Right. And he is a Jewish person. And he was saying that when he reads some of the ancient Jewish texts, how similar it struck him to some of the Stoic teachings and some of the ideas from the Romans. So how do you think it is this sad collision course of these two societies, but then an immense overlap in other ways? I think that's true. I think that there's cross-fertilization. I mean, if you look at where ancient Israel, Palestine is, it's at a crossroads of civilization.
1:07:15And there's Jewish diaspora that goes westward into the Roman Empire, but eastward into the Parthian and Sassanian Empire. So there's lots of ideas that are going back and forth. And I think that each of these civilizations, particularly the Jewish civilization, I'm Jewish too, so I know a lot about it. Each of these civilizations has its own way of dealing with things. But some of the same questions come up. And in some cases, they wrestle with the other person's ideas and they say, this is why we reject them. But they're aware of them.
1:07:47Ryan Holiday: And same with obviously the Christians coming up through Rome. And then also when it flips, then the Christians are sort of borrowing and taking credit for some basic philosophical ideas that predate them. I think it's Augustine who says we have to spoil the Egyptians. And what he means by this is he's talking about the thing in the book of Exodus where when the children of Israel leave Egypt, the Egyptians say, please get out of here. You've killed our firstborn. Here, take our gold and silver. Just get out of here, please. And so Augustine is using this image of saying we have to take from classical civilization what's useful for us.
1:08:33And we're not going to take all the horrible, bad things like all those awful Egyptian gods and goddesses. So, yeah, I mean, civilizations do take some things from other civilizations, but then they put their own spin on them. They mold them. I mean, there's this famous book of the Talmud called The Wisdom of the Fathers. Yeah. And when you read it sometimes, you think, who wrote this? Socrates? Yeah. It almost seems Socratic.
1:09:03Ryan Holiday: Yeah, when I read Ecclesiastes, I'm like, what Stoic philosopher is this? Yes, I know. Yeah. Yeah. It's really fascinating. Yeah. And what is that idea? Like the best ideas are common property at some level. Right. Like every cliche was invented by someone at some point and we agreed with it. And that's why we make it sort of into our own practice. Right. Right. You want to check out some books in the bookstore? Sure. Let's do it.
1:09:34Thank you.
What destroyed the Roman Republic was not one man or one moment, but a slow collapse of trust, duty, and shared values. In this episode, Ryan and ancient historian Barry Strauss discuss the broken civic bargain, economic strain, political violence, and personal ambition that pushed Rome toward civil war. They also talk about Cato’s refusal to compromise, Caesar’s decision to cross the Rubicon, and the warning the fall of the Roman Republic still holds for us today.
Barry Strauss is a bestselling author, classicist, military and naval historian, and one of the leading authorities on leadership lessons from the ancient world. He is a senior fellow at the Hoover Institution, the Bryce and Edith M. Bowmar Professor in Humanistic Studies Emeritus at Cornell University, and a leading expert on ancient military history.
Barry is the author of ten books on ancient history, translated into twenty languages, including The War That Made the Roman Empire, Ten Caesars, The Death of Caesar, and his latest book, Jews vs. Rome: Two Centuries of Rebellion Against the World’s Mightiest Empire.
Follow Barry on Instagram | @barrystrauss
📚 Barry Strauss' Books:
Jews vs. Rome: Two Centuries of Rebellion Against the World’s Mightiest Empire
The War That Made the Roman Empire
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