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Legends in Ancient Rome and Modern Tech with Jimmy Soni (Episode 15) image

Legends in Ancient Rome and Modern Tech with Jimmy Soni (Episode 15)

Stoa Conversations: Stoicism Applied
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Want to become more Stoic? Join us and other Stoics this October: Stoicism Applied by Caleb Ontiveros and Michael Tremblay on Maven

All ages will produce men like Clodius, but not all ages men like Cato.– Seneca

Why did Stoics idolize Cato the Younger?

In this episode Caleb Ontiveros speaks with Jimmy Soni, author of Rome's Last Citizen.

We focus on what is admirable about Cato the Younger, his contradictions, and his legacy. We also touch on Soni’s book The Founders which is a deep dive on the story of PayPal. It’s a engaging  book on the early days of what are now Silicon Valley legends.

Follow Jimmy on Twitter.

***

Stoa Conversations is Caleb Ontiveros and Michael Tremblay’s podcast on Stoic theory and practice.

Caleb and Michael work together on the Stoa app. Stoa is designed to help you build resilience and focus on what matters. It combines the practical philosophy of Stoicism with modern techniques and meditation.

Download the Stoa app (it’s a free download): stoameditation.com/pod

Listen to more episodes and learn more here: https://stoameditation.com/blog/stoa-conversations/

Caleb Ontiveros has a background in academic philosophy (MA) and startups. His favorite Stoic is Marcus Aurelius. Follow him here: https://twitter.com/calebmontiveros

Michael Tremblay also has a background in academic philosophy (PhD) where he focused on Epictetus. He is also a black belt in Brazilian Jiu-Jitsu. His favorite Stoic is Epictetus. Follow him here: https://twitter.com/_MikeTremblay

Thank you to Michael Levy for graciously letting us use his music in the conversations: https://ancientlyre.com/

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Transcript

Introduction to Cato and His Legacy

00:00:00
Speaker
for modernity, but sort of public consumption, is because Cato actually was not a self-promoter. He didn't write a lot of things down to leave for posterity. And so, by the way, contrast this with Caesar or Cicero, who like wrote everything and sometimes did it in the third person so that people would remember them.
00:00:19
Speaker
Right? And so they sort of had their own PR machines going. And meanwhile, Cato is not actually interested in PR. He knows the effect in his day of the actions he's taking, but he's not interested in making sure the posterity writes a certain story about

Podcast Focus and Guest Introduction

00:00:33
Speaker
him.
00:00:33
Speaker
Welcome to Stowe Conversations. In this podcast, Michael Trombley and I discuss the theory and practice of stoicism. Each week, we'll share two conversations. One between the two of us, and another will be an in-depth conversation with an expert.
00:00:50
Speaker
In this episode, I speak with the writer Jimmy Sony. We talk about Cato the Younger. Cato is an inspirational Stoic statesman. He's known for resisting Caesar's assault on Rome during the late Republic. Later Stoics took him as a powerful role model. For example, here's the Stoic philosopher Seneca. Choose therefore a Cato. Choose a master whose life, conversation, and soul expressing face have satisfied you.
00:01:20
Speaker
Picture him always to yourself as your protector or your pattern, for we must indeed have someone according to whom we may regulate our characters. You can never straighten that which is crooked unless you use a ruler. Jimmy has written the book on Cato, Rome's last citizen. We focus on what is admirable about the ancient stoic, his contradictions, and his legacy.

Exploration of 'The Founders'

00:01:44
Speaker
We also talk about Jimmy's more recent book, The Founders, which is a deep dive on the story of PayPal. It's an engaging book on the early days of what are now Silicon Valley legends.
00:01:59
Speaker
Here is my conversation with Jimmy Sony. Today I am speaking with Jimmy Sony.

Jimmy Sony's Writing Journey

00:02:05
Speaker
Jimmy has written several excellent books, including Rome's Last Citizen with Rob Goodman. And that's a book about the late Roman Republic and of course the stoic Cato the Younger. His most recent book is The Founders, which is on the PayPal mafia and the scene that emerged during the creation of PayPal. Thanks for joining.
00:02:27
Speaker
Caleb, thank you for having me. I really appreciate it. So what's your story? Yeah, that's a good question. It's a long story, but the condensed, the condensed, you know, version is I have the good fortune to write books about things that interest me. So, you know, it's sort of funny, the way I often think about it is, you know, you sort of go through your education in your early years and like many people end up going to college and you spend four years kind of learning a little bit of everything. I have this.
00:02:54
Speaker
Again, the good fortune now if I get to spend, you know, between three and six years immersing myself in a single subject. And because there's a product or an output at the end, it's very directed learning. And I think that's the reason that you and I connected is because one of the books I had written was about.
00:03:10
Speaker
You know, arguably for a long-term histories, you know, the person who mainstreamed socialism or it's sort of one of history's most famous stories. And then I've also had the chance to dive into, you know, the life of a mathematician, Claude Shannon, as well as the founding group that created the company PayPal. It's sort of famously known as the PayPal mafia. And so my story is I get to tell other people's stories, which is great. And I have the privilege of just doing that, you know, at some length, meaning it's not, I'm not doing essay length work. This is pretty in depth, substantive research that takes a few years.
00:03:41
Speaker
Right, right. These are not a book every year type event. It's a whole year of projects. I mean, I admire the people that do that. Just, it's a different kind of writing. I mean, most of my books clock in at a decent length, you know, so you sort of doing it in a year would be a little. What costs you to look back at the story of Cato?

Cato's Historical Context

00:03:56
Speaker
Yeah, it's a great question. I was, and it'll lead listeners to another great book, actually, I was reading this really wonderful book called Rubicon by Tom Holland. And Rubicon, many people have probably read it, I would say it's the best
00:04:15
Speaker
accessible narrative history of the late Roman Republic. Like you can read it and it's like a thrill to read. Like it reads like a movie script. It's amazing. And I was reading this book because I'd off I'd like actually had a long interest in Rome, like a long interest in Roman history and ancient history.
00:04:32
Speaker
I studied Latin when I was in high school, mostly because like the Latin competitions are pretty fun and I was a pretty competitive person. So that was, I was, it's like the least stoic thing I could probably say, but it's the truth. And so I sort of kept that interest going, did some Roman history in college. Not, I wasn't a classics major or anything, but I was reading Rubicon, great book. And I'm like totally absorbed. So I start buying biographies of Caesar and I read a couple of biographies of Caesar. Then I bought a biography of Cicero by Anthony Everett.
00:04:59
Speaker
And then I actually just went to buy a biography of Cato. There, you know, I just assumed like, oh, someone's done this. You know, it's truly sort of somebody has tackled this. And curiously, I didn't find anything. And that, you know, you know a bit about Cato, but for people who are less familiar, that's weird because alongside Caesar and Cicero, he's one of the giants of the late Republic. And a lot of what happens in the late Republic sort of orient itself around some of the decisions Cato made.
00:05:25
Speaker
And so when I didn't find that book, I was pretty young. I mean, I had no experience writing books, but I had a debate partner and friend of mine from college. His name was Rob Goodman. And Rob and I had always done fun things together. We read for the school paper together. We did all kinds of crazy things. So I basically called Rob up and I said, hey, Rob, I have a crazy idea for us. My crazy idea is we should write the first popular biography ever of Cato the Younger.
00:05:50
Speaker
At first what Rob said is what anybody would say, what are you talking about? We're not classicists, we don't have PhDs. It's crazy. What I said to him is I said, listen, a lot of the popular biographies aren't written by PhDs or professors. They are written by people like us. Both of us, he and I were speechwriters in politics at the time.
00:06:09
Speaker
And so I said, so why don't like, we're good at translating like weird, dense, complicated stuff for the public. That's basically what a lot of people think Roman history is like weird, dense and complicated. Right. And so I said, and look at this. So I finally got him over the edge. I said, look, here's the deal.
00:06:25
Speaker
If we do this and it doesn't work, like all we lost was the time it took to learn how to write a proposal. And the downside is that we learned how to write a proposal. The upside is like somebody can actually buy this ludicrous thing and see, you know, we could end up writing the book about Cato. And I'm being very honest about the origin story of this is not some, you know, and he's, he like laughing. He's like, yeah, that's a good enough reason. So we would after work and on the weekends get together and just research and like, you know, study all of the study plutarch study everything.
00:06:53
Speaker
And we wrote a proposal and we were fortunate enough to get it purchased. And that was what started the biography of Cato. Probably not what a lot of you listeners might have expected. Very nice. So yeah, I would also second the recommendation for Rubicon. It's both very engaging and informative. So how would you describe the scene in which Cato is growing up?
00:07:16
Speaker
Cato is basically coming of age during a convulsive period in Roman politics. There is blood in the streets, he himself sees sort of violence firsthand when he's a child, and he becomes an adult in a similar environment. There are
00:07:35
Speaker
crises around grain, there are crises around land, there are crises around soldiers coming back from war. And so he's coming of age in what is a period of real turmoil in Rome's history. He also has this secondary challenge of his grandfather, Cato the Elder,
00:07:54
Speaker
Well, actually funny enough, a lot of the quotes that are attributed to Cato the Younger are actually quotes from Cato the Elder. Cato the Elder was this giant figure in Roman politics. So you have a young Cato who is coming of age, like, again, in a period of real turbulence and with this very, like, outsized example of a person to live up to.
00:08:12
Speaker
You know, he really admired his grandfather. And so you have these two tensions in the air around Cato. I think the other thing to remember, and this is really important, you know, and we tried to do this, like politics in our time doesn't map directly to politics in ancient Rome, obviously.
00:08:29
Speaker
But one of the key things is that there's a much wider gap between the aristocracy and kind of everybody else, right? And Cato's an aristocrat. When he comes, he is born into that sort of strata of society. And so that's a bit of the context around Cato and his life and his times. It's an aristocratic upbringing with the expectation that he will do important things for the Republic, but it's happening amidst a lot of chaos. I mean, Cato sees violence even as a boy.
00:08:58
Speaker
Right, right. I mean, arguably the Republic has started falling before Cato has emerged into Rome. Like if you had one of those like Star Wars opening sequences for the Republic, like it would not be a pleasant sequence. There would be lots of paragraphs about doom and gloom and privation and war and difficulty. That's a great way to put it. How did Stoicism figure into Cato's life?

Cato and the Spread of Stoicism

00:09:25
Speaker
How did it begin as a more precise question?
00:09:28
Speaker
No, this is one of the most interesting things that I did not know until I really started going into this history. And it is the reason that the book, among other things, has taken off with people who really enjoy the history of Stoicism. A number of people who are kind of active in that space have become friends. And I didn't know this, but the analogy I sometimes use when I'm describing it to people is that if you were to think of Stoicism
00:09:53
Speaker
And the way it was received when Cato was very young, it was something like Scientology, like it was disreputable. And it was not the sort of thing that was like widely embraced or followed or practiced. If you talked about it, you were thought to be a little strange. Like that's just the truth.
00:10:09
Speaker
And there's a variety of reasons for that. They have to do with history and religion and then kind of all of this different things that were in the air. But that's where stoicism is when it arrives in sort of Cato's hands and in his mind. And what Cato does is he starts to live the principles of stoicism in his own way throughout his upbringing. Now, here's an important disclaimer for anyone listening.
00:10:33
Speaker
A lot of the stories that we have about boy Kato are written after we know about adult Kato. We write this in the book too. You have to take some of these stories with a grain of salt. There is this famous story of Kato being held upside down, outside a window when he is something like nine or 10 years old.
00:10:55
Speaker
According to the legend, he doesn't flinch, he doesn't bat an eye, he just stares back at the person holding him and like this sort of like stoic stare down and he just, he doesn't move, right? Now, that's a story that fits the picture of Cato the famous stoic, but it's an unlikely story. Like if a nine-year-old is being hung out of a building several stories above the ground, it's highly likely that he's gonna flinch or move or try to get back inside, right? Just with the reality of who we are as human beings.
00:11:23
Speaker
So that's an important thing, but right away, at least in the telling of the stories, a stoic demeanor, small estoism, is a part of the stories that are told about. Cato also very much wears, you could say, wears a stoicism on his sleeve, and there's a reason for this. It is immensely popular in the public, and he's trying to win votes.
00:11:44
Speaker
Cato is also a politician, and he knows the value of, for example, like walking around barefoot. He walks around barefoot because he wants to show people that his feet are so strong compared to his peers, right, who have to wear leather sandals. He walks around with a toga but with no tunic, so he is a little colder than everybody else around him because he wants to show that he can handle the cold. And what he is responding to is something in the ether in Rome which suggests that Rome has gone soft. There's this whole criticism kind of in that
00:12:13
Speaker
contemporary Romans are not as hardy as, you know, Romulus and Remus and then, you know, they're sort of follow on generations that Rome's basically become like a bunch of wimps and Cato explicitly wants to style himself as not that and Stoicism is a useful bridge for that. I mean, there's a bunch of other examples, but that is it leaves a deep imprint. He speaks about it. He is mocked because of it.
00:12:36
Speaker
And he embraces it. And then what ends up happening because of the way he lives his life and the way his life ends is that he's actually a big part of the reason why stoicism goes mainstream. So so Cato turns it from sort of ridiculous to mainstream in almost a single lifetime. You could.
00:12:50
Speaker
And ironic fact is similar to Cato the Elder, he criticized and saw Romans as at least sliding into decadence, being weak. But Cato the Elder, one of his largest pieces of evidence for that was that Romans were becoming too Greek and caring too much about philosophy, which Cato the Younger embraces, or at least embraces a certain style of philosophy.
00:13:16
Speaker
And look, there's all sorts of small and big hypocrisies, the heart of Cato's Embrace of Stoicism. And another great example is the perfect stoic is supposed to be somebody who is somewhat immune to grief and doesn't give into their grief. Meaning if something happens, they can see it for what it is, not for the feelings that they're having.
00:13:36
Speaker
When Cato's brother dies, he's a weepy mess. And it's one of the rare moments we have in the historical record of him being that one. And so that means it actually counts for, I think it counts for even more because it's a sort of specific story told, but he's essentially inconsolable.
00:13:52
Speaker
And, you know, it's the least stoic moment in his life. And so it's not the case that he was some person who always lived these principles. By the way, as is true for any of us, like any person who is aspiring to embody these principles has to know that they're going to come with moments of defeat and difficulty. Such was true for Cato as well. And so I just want to make sure people don't think like just because he had one moment of, you know, or that he was a spout, that he lived a sort of essentially like a Greek philosophy that it somehow was out of keeping. I think he embodied
00:14:22
Speaker
certain Stoic virtues in a way that, you know, has made his name come down to us through the generations. Right, right. He's known for being, he got quite far, at least as the general Stoic impression, especially of the ancient Stoics in terms of becoming a sage, but he was certainly not a sage by any means. He's not perfectly virtuous, whether it's with particular political moves we might think are dubious or, in this case, which is somewhat hard to fault him for, the death of his brother.
00:14:52
Speaker
Well, okay. So let's take one that might be more appropriate. And again, I'm not trying to fault him. And also there's, you can't sort of pick on an ancient figure. We just don't know enough. Right. That's as little, it's like a little bit like, okay, well, thank goodness. There's no sort of Cato LC that's going to come after me. Right. The Cato Institute.
00:15:09
Speaker
were actually great during the book launch. They loved it. And we should talk about where their name for Cato comes from, because it comes from an American Revolution era reference to Cato. But, you know, Cato is also a drinker. Like, we write about a couple moments where, as we described it, I think he was like deep in his cups. And that, again, was not inconsistent with the era that he lived in. Wine was, you know, there were sort of famous
00:15:30
Speaker
parties in Rome, particularly among the aristocracy, and it would not have been out of keeping for him to be drunk. Is that the most stoic thing? Probably not. But was it a part of the culture that he came of age in? Certainly. And, you know, he was, he abstained in other ways. He was kind of, again, famously testing his body and its limits. But, you know, he also enjoyed the occasional glass of wine, probably to excess. And I don't, you can't take anything away from his other, the rest of his life just because of that.
00:16:00
Speaker
Right, right. Yeah, sometimes one of my favorite lines is like even Cato had drinking parties whenever someone's critiquing your access. That's right. Yeah, of course. So I think there's all these sort of interesting examples where on one hand, Cato is exceptionally principled. He's a hardline person, which
00:16:16
Speaker
is evidence that he's someone that cares seriously about his principles, about being stoic. Roman politics is full of bribes and he makes some exceptions for family members, but relative to the era, he's quite hard on bribes, actually seems to run some physicians as a questor quite honestly and seriously.
00:16:37
Speaker
On the other hand, you have the fact that he did make exceptions for family members and that there's always this question, look, is this stoicism aspect a political front or not? So how do you see that, this general tension?
00:16:52
Speaker
Yeah, it's a great question. And I think it's one of these things that'll be doing it a hundred years from now and 500 years from now throughout history. I think it can be both. So here's what I mean by that. Someone can live life in a certain way, meaning adhering to certain principles, certain stoic principles or maxims, let's say. And you can live your life that way. And it can also make for really good politics.
00:17:18
Speaker
And there's a question of whether that is, of whether that makes you a phony. And I'm not sure it does. I mean, again, people, I think that's like a matter of opinion. Like you can have a difference of opinion on that thing. Here's like, so here's a great example.
00:17:34
Speaker
He was famously incorruptible and he would not take bribes. There were occasions where that slipped, but it was pretty rare. When he was overseeing one of the, I think it was a colony in Greece, he was one of the only people to clean up corruption in that colony. It was a colony that Rome had that was near Greece, something like that. He ran it with famous efficiency and incorruptibility.
00:17:58
Speaker
It was also good politics because people knew that Cato was doing it in an incorruptible spirit. He was a stoic governor. He was governing this place. Now, I don't think it takes anything away from
00:18:14
Speaker
the actions that he did that it also made for a good public posture for him. That the spot on the Venn diagram where those two things overlap doesn't take anything away from the behaviors themselves. I'll give you another example.
00:18:29
Speaker
He, you know, one of the things that happens if you're in a certain strata in Rome and you are leading troops, you are allowed the use of a horse. And Cato would famously like not use a horse. He would prefer to walk with his men side by side, right? And so he was always sort of leading from the front. Now, is that a posture and a pose? Yeah, absolutely is. I mean, he, I imagine it at his time, he consciously knew what he was doing and he knew that he was sending a message and he knew that he was being watched and he knew that he would have a public life at some point.
00:18:57
Speaker
At the same time, it earned him the respect of his men, right? He was thought to be one of them. And he was taken more seriously as a leader, as a result. Now, again, I don't think it takes anything away from him to know that both of those can be true. And, you know, I think politics is the art of, I sometimes think politics at its core is the art of tolerating hypocrisies. The question is whether you tolerate gargantuan hypocrisies or little hypocrisies.
00:19:22
Speaker
And so I am willing, I mean, again, a matter of personal opinion, I'm willing to accept that he probably consciously knew that people loved the sort of, you know, tough, gruff grandson of Cato the Elder, you know, who was a little bit of a, little bit of a prig and a little bit of a person who, you know, had some difficulty and like really endured difficulty and wanted to be this person.
00:19:46
Speaker
I think he knew that. And I also think he actually sort of walked the walk too, literally walked the walk, like walked barefoot next to his men, all of that. The other thing about this that's important is, you know, you do have a high degree of overlap. Like the reason we know about certain stoic figures is because they were involved in public life. Had Cato been a purely private figure, we might not have known about him. And there is always this live debate about like what the role of the stoic is in politics.
00:20:12
Speaker
And I think that one of the things that stoicism does so well is it really does properly teach you how to respond to criticism and how to respond to praise, which is to say they're both sort of equally vapor, right? And they're fleeting and they don't actually count toward what your character is. And so that's a way in which like the blending of stoic, like I wouldn't mind more stoic politicians to be totally honest, right? Because you could see a universe in which that sort of belief system or operating system
00:20:40
Speaker
actually leads them to be willing to buck convention, be willing to do certain things that might be unpopular. Cato never shied away from a position just because it was unpopular. If anything, he ran into the teeth of unpopularity, particularly when it came to Caesar. Caesar was this widely admired, widely loved figure and Cato just continued to hold the line against him. At the end, you could argue he held the line to his peril and to Rome's peril, but I hope that gives some texture to it. I don't think that it is
00:21:10
Speaker
I don't think it takes anything away from Cato the person to say that Cato the politician was widely known as a stoic.
00:21:17
Speaker
practice stoicism with stoa. Stoa combines the ancient philosophy of stoicism with meditation in a practical meditation app. It includes hundreds of hours of exercises, lessons, and conversations to help you live a happier life. Find it available for a free download in the Play Store and App Store. What do you personally find most admirable about Cato?
00:21:43
Speaker
willingness on the part of a lot of politicians at the time in Rome to bend to Caesar. And there's a fair argument to be made whether Caesar had designs on a dictatorship. And Cato is one of the only people sort of calling a spade and sort of saying like, look, this is a proto dictator in our midst, our republic is designed to guard against this, and I am going to stand against him, you know, come hell or high water.
00:22:06
Speaker
And that, you know, he does it ultimately, he does it to the point that he takes his own life out of conviction and in sort of keeping with that principle of opposing Caesar. The sort of backstory for people who don't know is rather than submit to Caesar's tyranny once Caesar has won the war, Cato kills himself. And it's depicted and could have made famous in these famous scenes during the Renaissance, like the Cato suicide kind of lives side by side with Socrates drinking the hemlock.
00:22:36
Speaker
So it's hard not to admire that kind of conviction and that kind of willingness to stick to principle, right? To not bend even in the face of your own death, right? And to sort of not give an inch. I think there's something to that. I mean, that's like, that's incredible. The second thing I would say is, and this is a little bit counterintuitive, Cato is one of the few people from that. And the reason there was no biography written, kind of no long one for modernity, but sort of public consumption is because Cato actually was not a self-promoter.
00:23:06
Speaker
in a, he didn't write a lot of things down to leave for posterity. And so, by the way, contrast this with Caesar or Cicero, who like wrote everything and sometimes did it in the third person so that people would remember them, right? And so they sort of had their own PR machines going. And meanwhile, Cato is not actually interested in PR. He knows the effect
00:23:28
Speaker
at in his day of the actions he's taking, but he's not interested in making sure the posterity writes a certain story about him, which is actually like why we only really have like one letter that he wrote, or sort of like a couple paragraphs he wrote. And so I admire that. I mean, that's like, that's kind of the opposite. It's like the person who decides to do a social media diet permanently, you know, like it's sort of
00:23:48
Speaker
It's sort of this person, like I think of him as like, I don't know, if he was modern, he would probably like rage against Twitter and like not do it. You know, he would be, Kato is a Cal Newport, like I'm stretching Cal's grade and I love his work, but that's, I think there's something admirable about somebody who is not looking to win points for history because it, there was something about that set him apart from every other leading figure of his era. And I admire that too. I mean, that's two things that I could go on at length.
00:24:17
Speaker
Yeah, of course. On the other hand, what do you think are some of his failings? Or is that another important question? Yeah, I would say there's a couple. There's more than a few. One is...

Cato's Political Influence and the Roman Republic's Fall

00:24:28
Speaker
Some historians have observed that it was Cato's unwillingness to compromise that led to the demise of the late Republic. And I think that it's a fair criticism that if Cato had been more like Cicero and had been more willing to create alliances, to build coalitions, to find other people that supported his political platform, that it's quite possible that you would not have had the rupture that you had at the end of Cato's life and that Cato wouldn't have had to take his own life.
00:24:56
Speaker
I think it's hard not to look at what is conviction and then see at the end that it curdled into stubbornness or obstinacy. By the end of it, he is just intransigent and gives Caesar no room to back out, which leads Caesar to march his armies onto Rome.
00:25:15
Speaker
And so it's really like you have to stretch to find the virtue in that. And so there's this part of you that wants to admire the ability to stick with your beliefs. And then there's part of you, even as we were writing the book, we're like, there were like 14 options for you here, man. Why didn't you just do some of these things sooner? You end up making common cause with Pompey, but there's a little too late by then. I would say the other thing is it's really tough to look at his relationship with Cicero and not think that Cato couldn't have done more to be a better friend to Cicero.
00:25:45
Speaker
You know, like, like Cicero is actually like, he is one of like Rome's great, brilliant politicians and Cato kind of, you know, he gets a few too many, which feel like unfair jabs in at Cicero from time to time. So I have a hard time admiring that. I think the other thing is, you know, it's sort of not my place to debate the ethics of suicide, but I think a lot of people would, I think, fairly say, look, what would, what could Cato have done alive to resist Caesar? Right. Was his last,
00:26:14
Speaker
Donner taking his own life an act of showmanship and not an active statesmanship and that I think it's a fair criticism I don't think I I sort of have my head wrapped around it enough to their way in one way or the other but I do think that like at some point you can cross the line from conviction into stubbornness and I have that that I can see as well and by the way like
00:26:37
Speaker
sort of shouldn't surprise anybody that we see some of the echoes of this in contemporary politics where politicians sort of say what they're doing is a result of conviction but what they're actually just doing is not compromising for the sake of not compromising.
00:26:50
Speaker
Right, right. Yeah, the suicide issue is interesting. I suppose with Caesar's famous clemency, you have the same issue where clemency has this political advantage, but there's also just an argument from political justice. Caesar is well known for granting clemency to his enemies. Typically in the Roman world, enemies would be, you know, purged if they needed to be. And in fact, that's what happened when the next Caesars came along.
00:27:13
Speaker
But, you know, Cato sees this clemency for what it is in part as a way for people to think of Caesar as great, as a sort of person who has the power to grant clemency and resists any offering that Caesar would have and decides to take his own life or instead. And there's certainly the argument that he could have done better in Caesar's Rome, as it were, which may or may not be true. It's always hard to say.
00:27:37
Speaker
It's always hard to say, but you do have to look at, sort of take a different historical period, right? You know, Winston Churchill is somebody that at his different moments had his sort of doses of stoicism. And he was pretty well read in the ancients too, so it's sort of no surprises there. You know, he is famously out of power before returning to power, but his, and look, he's not thrown out of power because he's opposed to national socialism and the rise of the Nazi party, but he is one of the few voices sort of
00:28:05
Speaker
crying, sort of saying like that this problem is different than what many leaders in Britain and the United States think it is. And it's far more sinister, far more dangerous. And
00:28:15
Speaker
But he returns to power and embraces a political project in which he has to make compromises, right? And has to do things like he's engaged in the work of politics much in the same way that Cicero was engaged in the work of politics. And to the end, like right up until the end, Cicero is still trying to figure out how to keep the Republic together. Whereas I think in some ways Cato kind of
00:28:36
Speaker
Kato gives up, and you could argue that it was profoundly short-sighted. Again, it's sort of a hard debate to have because we only have the facts that have been written down by historians, and we catch little bits and pieces, and we catch a story about a nine-year-old Kato hanging upside down outside a window, and you're like, how can I actually believe this? And it's why throughout the book, Rob and I tried to give the context for a lot of this, because context is important.
00:28:57
Speaker
But I think that's the tricky thing is when does conviction prevent compromise? It just feels like so many of the political moves had no good outcome and Caesar was left with no choice.
00:29:12
Speaker
Epictetus has an example of a servant holding a chamber pot, which is a very demeaning thing to do, and a servant asks, you know, should I hold this and face, you know, basically this demeaning action, or should I refuse and face the punishment for my master? And Epictetus doesn't really answer that question when it says you should choose one and don't be the servant who holds the chamber pot and imagines themselves, you know, resisting, has this fantasy that you're resisting your master.
00:29:41
Speaker
And I think Cato sort of chose the line of resistance throughout his life in a way. And if he hadn't committed suicide, he wouldn't have been Cato. So there's there is always that perhaps he should have been the person of compromise like Cicero. But there is that thought that, you know, he chose this line and pursued it to his end. And there's something in that conviction that is, as you were saying earlier, that is admirable. It's admirable. And I think it it's also
00:30:03
Speaker
You know, the details of his suicide are important, I think, for listeners to hear because he stabs himself in the guts thinking he is going to die right away. He does not die. He loses by historical accounts. He loses consciousness. A doctor is sort of, you know, furiously called in. They stitch him back up. And according to the accountings of historians, Kato
00:30:27
Speaker
comes to, pushes away the doctors, and then rips the bandages out, rips his guts open, and bleeds to death. So it isn't just a suicide. Part of the reason it's always depicted the way it was later and in later scenes and recount, and you're right, it turned Kato into one of the model stoics, is because it was also very gruesome and very painful. And so I think you're right.
00:30:50
Speaker
you sort of fault him, you could fault him for the decision, and you also know that without the decision, he wouldn't be Cato, right? And so maybe it's actually like an impossible task. Yeah, and it is always ironic that the people who you think would be in the next Cato, the next Stoics are people who end up advising Augustus and as a dictator, not that the Republic has fallen. Right. And then later, of course, there's a stoic opposition who goes against the dictator. So, stoics have always had a problem with their political philosophy.
00:31:20
Speaker
Yeah, I think stoicism in politics is hard to blend for the reasons we talked about. It's just hard. You know, the closest, the closest contemporary figure, because we would get asked a lot. This book came out a while ago and it was in the time of sort of John McCain and Barack Obama. And we would get asked a lot, like, who do you think? Like, if you had to pick a name, you know, it doesn't matter what party they're in, but which politician went. And we always, always would come back to John McCain, right? And the kind of straight talk express. We were like, Cato is, Cato was on the straight talk express of his day, you know, and sort of in the same way that that John McCain
00:31:49
Speaker
was thought to be someone different because of what he had endured in Vietnam and was someone different because of what he had endured in Vietnam and being tortured under captivity and then refusing to leave when he was given a chance to leave despite I think his father or grandfather being some kind of admiral or something in the Navy. McCain chose to stay by the side of his fellow soldiers. We often thought that like if you were sort of there to get somebody from central casting for the role of Cato, it would be somebody like a John McCain.
00:32:14
Speaker
similarly independent minded. And I think that's right, that the independence streak is what led to him taking his own life. Yeah, that's interesting. That's a good answer. But what initially comes to mind for me would be someone like, there are some differences here, but Ron Paul or Bernie Sanders, where they have, you know, they're known for being especially principled and they pay a price when it comes to their party's inner machinations that has both pros and cons for them, that strategy. Who do you think is the most Cato like in your book, The Founders?
00:32:44
Speaker
Oh boy, that's a great question. And for listeners who may not have context, the founders is about the origin story of PayPal and the kind of history of the PayPal mafia in the early days. So it's people like Elon Musk, Peter Thiel, Reed Hoffman, the founders of YouTube, et cetera.
00:32:59
Speaker
That's a great question actually. Nobody's ever asked me that. Who is the most stoic? I think Peter Thiel. Not just because of like the way he presents as a person, because he's actually sort of very funny, has a great sense of humor. It's more that he's able to rationally and coolly look at situations. And there's a couple moments in the PayPal story where he makes the right call when everyone is advising him to do something else.
00:33:18
Speaker
And I think that's a very, it's like an embodiment of stoicism because he's not sort of letting the emotions of the moment or sort of feelings of the moment really override him. Now, I think that analogy only goes so far. There are definitely moments where he shows emotion, but I think if I had to say that's one, but I think actually the other would be Elon because part of he does well is dealing with setbacks.
00:33:39
Speaker
And I think a big part of the reason that particularly in 2023 that a lot of people come to stoicism is because it's an operating system for helping you deal with setbacks or difficulties and to really getting to the root of what those difficulties are. And I think during the four year period of his life in which I'm writing about him, meaning the four years that I wrote about where Elon's a character, 1998 to 2002.
00:34:01
Speaker
is he gets thrown out of a company that he created, he almost dies in a car accident, he almost dies because of malaria and meningitis, and he loses a child. And so it's sort of these four things that befall him that any one of those would be difficult to go through. And in the aftermath of that,
00:34:21
Speaker
He registers the URL spacex.com and begins building, you know, what becomes the leading private space company of our era and becomes an investor and then leader of Tesla and accelerates sort of electric vehicle production. And so I think he has this ability to move through difficulty that is very stoic. He's also really well read in the ancients. A lot of his jokes reference the ancients and he's actually very, he's very scarily well read when it comes to ancient history, both Greek and Roman.
00:34:51
Speaker
I didn't know that. That's a fun fact. So, Kato is known for opposing Caesar, of course. And Caesar is the sort of person who probably, in some respects, similar to Kato is seen as a heroic figure and also a villain or at least the cause of a lot of turmoil. But how do you see those two parts of Caesar? Caesar playing out. You have the dictator versus someone who
00:35:17
Speaker
realizes the Republic is falling and starts to build it up and exceptionally competent, or at least begins the plans to do so before he is assassinated.
00:35:28
Speaker
Yeah, it's a... Look, this is something that's been hotly debated and discussed and dissected since the days of Caesar himself and, you know, far more capable sort of observers of human character like Shakespeare have written whole plays about this, right? And so it's a question of what the line is between Caesar's personal ambitions toward power and his belief that he was building a stable political project for Rome. And...
00:35:56
Speaker
I, it's sort of hard to weigh in. One of the things that I saw across the board in studying just different figures in power is that there's that sort of old line, right? Like sort of power corrupts and absolute power corrupts, absolutely. And I think that one of the things that you learn as you sort of learn about figures in power
00:36:18
Speaker
is that it's very hard to be someone who willingly walks away from power. It has a seductive quality on the order of the ring from Lord of the Rings. It is too tempting.
00:36:35
Speaker
And there are different moments where Caesar himself refuses to compromise, where he takes actions that reflect what a dictator ought to and would be doing. I would say also he's pretty, he like flouts sort of all of these social conventions in some ways that are pretty
00:36:53
Speaker
weird and then he goes and I think makes fun of Cato for sleeping with his half-sister in public, right? And so it's sort of tough not to look at that and think like, if you were really interested in like the preservation of the Republic, there are all these things you probably would have done differently. The other concern, and this is important, and this is again, context. Context matters with all these stories. We can't sort of, it's even hard to talk about it in 2023, but Rome is coming off of a bloody series of dictatorships.
00:37:18
Speaker
And so their experience of dictatorship is just wholesale slaughter in the streets. And the concern about Caesar is that his troops are more loyal to him than they are to Rome. And so I think Cato and Cicero's concerns about Caesar are justified in light of concerns about dictatorships and about the bloodletting that can happen once someone has absolute power. I think on the personal side, it's hard for me to see a universe in which Caesar would have willingly walked away
00:37:45
Speaker
from sort of being dictator, right, short of being killed. And again, like on a catch me on a different day, I might have a different view on that, but that's the tricky part of this. I think the other thing that's interesting to me
00:37:58
Speaker
about this is it is the reason what we just talked about is the reason that Cato is inspirational to George Washington and Thomas Jefferson and John Adams and Caesar is not. And in fact, when the American revolutionaries want to criticize King George, they will call him Caesar, right, or use sort of that language to talk about him. And they will refer to themselves in private and in public as Cato's or proto Cato's, right, because they thought they were restoring to some degree
00:38:28
Speaker
the like the roman republic in america and that so there's something about that i think it's hard because i wrote so much about it it's hard not to think about it in those terms too right um but i find that's kind of where i net out is it sort of knowing what we know about power and knowing what we know about the about rome's history with dictatorships it's hard not to see caesar is dangerous and it's presumably why ikido and caesar did too hi everyone this is michael trombley
00:38:53
Speaker
Thanks for listening to Stole Conversations. We're a new podcast. We're getting started. We're building episode by episode.
00:39:03
Speaker
So I wanted to just give a quick shout out and say that any like, review, or referral that you can provide really goes a long way to helping the show. Right, right. This is perhaps, I've mentioned that the American Founding Fathers is a good transition to the question of Cato's legacy through time. Earlier we mentioned the Cato Institute, which is based off of letters, I think, in the early 19th century in Britain, which have much more, almost enlightenment, liberal-type view, so that you have this view of
00:39:31
Speaker
the person facing against tyranny.

Cato's Enduring Legacy and Influence on Modern Thought

00:39:34
Speaker
That's one of the main dominant pictures of Kato is his ability to resist the tyrant.
00:39:41
Speaker
Yeah, this is actually, you know, it's the most it's one of the more interesting things about someone who wrote very little down has an afterlife that lasts. I mean, we're talking about him on a podcast in our overall laptops, you know, and he didn't have volumes of volumes of documents that he left for posterity. He didn't write an autobiography. Caesar would actually write these kind of news updates where he would refer to himself in the third person and send it back to Rome for public consumption. So, for example, when he had a big military campaign success,
00:40:11
Speaker
all of Rome knew about it because Caesar wrote the bulletin that updated everybody. Cato didn't do that, and yet we're still talking about him. And just to take a step back, his influence throughout history starts almost right after his death. And part of what happens is that this sort of suicide becomes, you know, it was referred to at different moments as, quote, unquote, the good suicide. So a lot like the self-sacrificial acts of Socrates or of Jesus. And so a lot of the depictions in the Renaissance
00:40:41
Speaker
are of all through those three scenes, right? Become sort of rich fodder for artists looking to depict the ultimate act of self-sacrifice. So that's kind of one domain. The other domain in which we sort of see Kato come to life again is that there's a play by a playwright named Joseph Addison. That's called Kato and it's
00:41:03
Speaker
It becomes the most, I think it was the most popular play in Britain. It then sort of gets exported to America and becomes the most popular play in America. And George Washington is so inspired by it that he stages it at Valley Forge for his troops.
00:41:19
Speaker
And this is sort of a famous, well-documented scene where he is staging this play about the Saint-Germain senator for these freezing, barely keeping it together, troops in Valley Forge during what is a very hard winter. There are other things that some listeners will know if they know the line, give me liberty or give me death. It's attributed to Patrick Henry. The line comes from the play, Cato. And then probably the most famous example
00:41:43
Speaker
is that, you know, there are, when the British are, when those are the early stages of the revolution, the British are trying to make examples of certain Americans. They capture a young American named Nathaniel Hale, and they execute him for treason. And before his execution, he's asked, do you have any sort of last words? And he says, I regret that I only have but one life to give for my country.
00:42:04
Speaker
And it becomes this kind of like emblematic thing. Like there are still, you know, hail statues all over America. I think just one in Yale, I think there's a few in some other places. That line, I regret that I have but one life to give for my country, is a line from Joseph Addison's Cato. And so you think about it, I think Nathan Hale was 17 or 18 when he was killed. 17, I'm pretty sure. And if you think about a 17-year-old quoting a play right before he's about to die, it sort of shows you the impact that Cato's life and legacy had on the founding fathers.
00:42:32
Speaker
Each of them at different moments referred to themselves. They wanted people to refer to them as the American Cato. It was like a rock star status. They wanted to be this person. George Washington very explicitly tried to style himself in this manner. He famously wrote these rules of civility and friendship. No.
00:42:55
Speaker
Rules of civility and decorum among friends, whatever the name of the book was, but it was like sort of the same kind of thing of like, it was a little much. He sounds like a fuss pod at different moments, but it's kind of explicitly in this same sort of like, you know, Catonian project of like, oh, if people, if I'm this way, people will think a certain way of me. And then I think Kate, you know, then George Washington does what might be the most, one of the more stoic things that anybody's ever done. He walks away from the presidency in two terms, which set the model for what the American presidency would be for the next until Franklin Delano Roosevelt. And so
00:43:25
Speaker
That is the historical, kind of long-lasting legacy that comes later. It comes in the form of plays, it comes in the form of paintings. Plutarch writes a life of Cato. And so even all these years later, Caleb, that, you know, we are still discussing this person despite having, I think, all of maybe two paragraphs of text that he wrote by his own hand.
00:43:47
Speaker
And so it shows you the power of that example and of that model. I think it's a big part of the reason why stoicism took off the way it did in Cato's aftermath. Yeah, absolutely. It is worth emphasizing that the only bit of written text we have from Cato is basically a letter putting down Cicero for some award.
00:44:05
Speaker
Like I said, not the best, like there's like friends, but enemies, frenemies is probably a good description. You know, like Kato is at times for a little, a little hard to be around, you know, and he's not the person you'd want to invite to your dinner party, most likely, but you know, you never know. I mean, if you have that wrong. Yeah, who knows? You have a very philosophical dinner party, perhaps. How has working on this project, reflecting on it a few years later, sort of changed your view of stoicism, if at all?
00:44:33
Speaker
You know, I think it enhanced it considerably. I mean, I was pretty young when I wrote the book and I had no real exposure to stoicism until I studied the life of Cato. And what's great about learning about the stories of the Stoics or actual people
00:44:50
Speaker
is you start to see like how life experiences shaped their philosophical beliefs. And I think sometimes like you can have a belief, but you need a story to really like make it real in your mind. And so, you know, am I saying that there's sort of some direct effect? Like I didn't lose 10 pounds after writing a book about Cato, right? Like it's not quite that direct, but I think that you find, you do find, for me it's two things. One is I think about politics a little differently. And I sort of think about the way people present in politics a little differently.
00:45:20
Speaker
And then also, you look at moments of leadership and moments where he abstained from corruption, and you try to live up to those ideas and stories. And I think that is really important. It's one thing to read a stoic quote, but it's another to learn that Epictetus was a slave.
00:45:40
Speaker
It's one thing to read an aphorism. It's another thing to know that Marcus Aurelius didn't just have a hard job. He was emperor. He had the hardest job and lost, I don't know how many kids, right? Like there's a punch. It was like, at least. And it's sort of one thing to read about the ideas. It's another to see them lived in practice. And the thing about
00:46:00
Speaker
doing it with the ancients is the ancients are explicitly talking about stoicism. They're not talking about it like abstractly, like it's directly related to like the ideals and you're getting closer to the formation of some of those ideas. And so that to me is, has been the most important thing is that it just made me put stories to the ideas and to find out that it took this person, you know, this politician, this public figure, this Roman senator to bring stoicism and some of its concepts, you know, sort of out from the shadows and into the light.
00:46:29
Speaker
So one character you talk about in the founders we've mentioned already is Peter Thiel, and Peter Thiel has greatly influenced by the work of a French literary theorist and philosopher René Girard. One of his big ideas is how humans imitate each other, not just in the sense that we copy each other, but sort of a very fundamental sense. We copy each other's desires, that sort of level of
00:46:50
Speaker
being is a philosophical way to put it. How do you see this memetic, memetic rivalry or memetic actions play out over the late Republican in Cato's life? Well, that's a great question. And you should talk to my friend Luke Burgess who did this wonderful book called Wanting, which is all about memetic desire because I think he'd be better positioned to speak about it. Here's what I think about it because I've never thought about Cato in that context necessarily, but it's an interesting question.
00:47:20
Speaker
Cato illustrates the power of resisting mimetic desire because sort of sees that there's virtue, like certainly political upside, but also virtue in standing apart from the crowd. And again, that's a gross oversimplification. But one way in which Cato is powerful is that he is anti-mimetic.
00:47:41
Speaker
right, that he doesn't want the same things as everyone else. That actually his, like, and in fact, when he sees that too many people want one thing, he's very suspicious of it, right? He is very suspicious of Caesar's popularity. He is very suspicious of commander, military commanders, battlefield commanders who live in a cosseted way or who have used their horses or anything, right? So Cato sort of shows you how, like,
00:48:10
Speaker
Kato is not—Kato's desirous of some of the same things that other people are, but there are parts of his entire sort of makeup and his actions that are deeply anti-memetic, right? And so I think that's probably an insufficient answer, but it's where I would land initially, is that—
00:48:26
Speaker
Like I think, you know, he didn't, we didn't have Gerard, Cato didn't have Gerard to think about, but his, his, you know, the sort of opposite of mimicry is that is, is what Cato was doing. That his desires were distinct from the desires of somebody like a Cicero. And by the way, there's like some good reason that might just be personal history. Cicero didn't come from wealth. Cato did, right? So Cato kind of had the room, like a little bit of the room, because he was a patrician to like actually like live a certain way, right? He was part of what is known as the optimates in Rome.
00:48:54
Speaker
And so he kind of had like the ability to not be a striver, right? And he could he could throw stones at his own people because he was one of them, right? And this is sort of like a very classic trope within politics or business. It's sort of the person who doesn't want power becomes powerful. The person who doesn't want a thing becomes the thing, right? And I think that's a that's part of that. It's an interesting way to think about it. Yeah, I suppose you have a lot of the competition for
00:49:19
Speaker
Roman honors is somewhat memetic. You have this picture of the typical Roman aristocrats will get some governorship and they need to be a good governor, bring back revenue to raise their status. That'll help them get some other additional office, maybe some military command, and all of these steps are sort of building up
00:49:42
Speaker
a ladder onto, you know, just taking steps up a ladder to Roman honor or something like this. And Cato is involved in that to some extent, but he's not as predictable, perhaps, as one way to put it, or he has principles. He's not nakedly trying to go up the ladder, which makes him less exploitable by people like Caesar, or Pompey, or just handing out bribes, or expecting people to go along with signs of physical force, or what have you.
00:50:10
Speaker
Yeah. It'd be interesting to think about, because one of Girard's things is around who is the scapegoats. The scapegoats are a big part of his thinking and writing. I have to go back and really think about the late republic to know how much scapegoating was happening and by whom and toward whom. One of the big problems is like, Rome had structural issues in its governance and structural issues in its economy that weren't necessarily going to be resolved by one principle's Cato.
00:50:39
Speaker
Right? And so you have to think about like, if you're thinking about where to assign blame or where the public assigned to blame, that would be interesting in a sort of Girardian sense. One last question about the founders. Who's an underrated, the founders to be clear, the Paypal Mafias, and she's also been mentioning the American founders. Who's an underrated figure from that story who you think more people should know about?
00:51:01
Speaker
It's a great question. I think people know the names Elon, and they know Peter Thiel, and they know Reid Hoffman. I would say probably the one that's underrated relative to his accomplishments, let's say. And again, this is sort of like we're just chatting. There's a scientific method to win it in this assessment. So I sort of add that disclaimer. But I would say Max Levchin is probably the one that
00:51:21
Speaker
He is widely known in Silicon Valley circles, well regarded in those circles, not a household name, I think deliberately. And I think he was a little embarrassed that I was even sort of writing the book and made him as big a part of it as I did. And, but I think his story is a very classic immigrant entrepreneur story. And I think in many ways it embodies what Silicon Valley is at its best. And he is also somebody who's sort of animating impulses is just solving problems with code. And there's a kind, there's not a.
00:51:53
Speaker
You know, there's a sort of, he has this instinct of, he is still the engineer. He's still the sort of 20 something, always the 20 something engineer trying to fix a problem or solve something. And I think he's underrated because he's not actually looking for fame and he's not actually looking to sort of run the world, right? Whatever that may mean. And he doesn't acquire such controversy. So people don't know who he is, which is really disappointing because in some ways.
00:52:16
Speaker
He is one of the more successful entrepreneurs of his generation of technologists. And I think more people should know about him. Very good. Well, is there anything else you'd like to add?
00:52:28
Speaker
No, I just appreciate you doing this. And so it's really fun for me because this book, you know, this book is like a little bit of a, it was sort of my first effort at writing a book and I'm just glad to know that it resonated and that it landed in the way that it did. And we're talking about it because it's one of the more interesting periods of history just overall. And I think, you know, I'm just grateful to you for taking some time and introducing people to it. Yeah. Thanks so much. I recommend it highly. It's a great way to learn more about Cato and the late Republic in particular.
00:52:59
Speaker
Thanks for joining. Thank you.
00:53:18
Speaker
And I'd like to thank Michael Levy for graciously letting us use his music. Do check out his work at ancientlyre.com and please get in touch with us at stoameditation.com if you ever have any feedback or questions. Until next time.