The UNTOLD Emotional Struggles of History’s Most Powerful Men | Ron Chernow (PT. 2)

Mark Twain didn’t just write American classics, he lived one of the most powerful personal transformations in history. In Part 2 of this conversation, Pulitzer Prize-winning biographer Ron Chernow returns to join Ryan for a deep dive into Twain’s remarkable moral evolution. They discuss how Twain’s journey mirrors those of Ulysses S. Grant and John D. Rockefeller, reflect on the tragic cost of chasing fortune over purpose, and explore what makes a biography timeless and a life unforgettable. Plus, a special moment: Ryan’s 8-year-old son jumps in to ask Ron about Hamilton, his favorite musical. Ron Chernow is the prizewinning author of seven previous books and the recipient of the 2015 National Humanities Medal. His first book, The House of Morgan, won the National Book Award, Washington: A Life https://www.thepaintedporch.com/search?type=product&q=ron+chernow* won the Pulitzer Prize for Biography, and Alexander Hamilton https://www.thepaintedporch.com/products/biography?_pos=2&_sid=b388eb57e&_ss=r—the inspiration for the Broadway musical—won the George Washington Book Prize. He has twice been a finalist for the National Book Critics Circle Award and is one of only three living biographers to have won the Gold Medal for Biography of the American Academy of Arts and Letters. Ron’s latest book is on the fascinating and complex life of American writer Mark Twain https://www.thepaintedporch.com/products/mark-twain?_pos=1&_sid=b388eb57e&_ss=r. Follow Ron Chernow on Instagram https://www.instagram.com/ronchernow/?hl=en: @RonChernow https://www.instagram.com/ronchernow/?hl=en 📚 Grab signed copies of Ron Chernow’s books about Mark Twain https://www.thepaintedporch.com/products/mark-twain?_pos=1&_sid=b388eb57e&_ss=r, Alexander Hamilton https://www.thepaintedporch.com/products/biography?_pos=2&_sid=b388eb57e&_ss=r, George Washington https://www.thepaintedporch.com/products/biography23?_pos=5&_sid=b388eb57e&_ss=r, Ulysses S. Grant https://www.thepaintedporch.com/products/grant?_pos=3&_sid=b388eb57e&_ss=r, and John D. Rockefeller https://www.thepaintedporch.com/products/biography21?_pos=4&_sid=b388eb57e&_ss=r, at The Painted Porch | https://www.thepaintedporch.com/ https://www.thepaintedporch.com/search?type=product&q=ron+chernow* 🎙️ Follow The Daily Stoic Podcast on Instagram https://www.instagram.com/dailystoicpodcast/?hl=en: https://www.instagram.com/dailystoicpodcast 🎥 Watch top moments from The Daily Stoic Podcast https://www.youtube.com/@dailystoicpodcast on YouTube https://www.youtube.com/@dailystoicpodcast: https://www.youtube.com/@dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail 🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/ 📱 Follow us: Instagram https://www.instagram.com/dailystoic/,Twitter https://twitter.com/dailystoic,YouTube https://www.youtube.com/@DailyStoic,TikTok https://www.tiktok.com/@daily_stoic?lang=en, andFacebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:03Ryan Holiday?

  Welcome to the weekend edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring.

• 0:54Ryan Holiday?

  Hey, it's Ryan Holiday. Welcome to another episode of the Daily Stoic Podcast. What you're always looking for as a parent is connection between you and your kids. Sometimes they're interested in all your experiences and the things that you know. And sometimes they trust you when you recommend things, but most of the time, they don't. They're cynical. They're skeptical. They're like, who is this guy? They don't know about video games. They don't know about this. That's what they think of their parents, right? Even though my kids are young and they're wonderful, and they look up to me, and they love spending time together, they like to make fun of me, as all kids do. And a couple of years ago, my son got really into this thing called Epic,

• 1:35Ryan Holiday?

  which is, I don't know, would you call it a rock opera, a musical, this series of albums, all about the Odyssey. And we've gone down this huge rabbit hole about the Odyssey. I've talked about that. And one day, getting tired of hearing this album for the thousandth time, I said, you know, there's another one you might like. Do you know who Alexander Hamilton is? And he goes, no. And I was like, well, there's a whole musical about this guy named Hamilton, who's one of the founding fathers. I think you might like it. And in an instant, our lives were changed because he became utterly obsessed with Hamilton. He dressed like Hamilton for Historical Figure Day at his school. He was Hamilton for Halloween. And he knows almost every song of the album by heart. We went and saw it when it came through. And as much as he liked the musical, I go, you know, there's a book about this. And he goes, what?

• 2:20Ryan Holiday?

  And I go, yeah, the musical is based on a book and we carry the book in the bookstore and I have read it. And I was like, I not only read it, I got excited and I went and saw Hamilton's grave in New York, right after I read the book. And he said, what? And I was like, you know what? Let's listen to the audiobook. And so we made it our way through the 30 something hour audiobook to and from school, piece by piece. And then a couple of months ago, I was giving a talk in New York City at JP Morgan Chase and I walk out after and there are the pistols in the lobby. My, my son about lost his mind. So when I told him that Ron Chernow was coming to do the podcast, he was like, can you come pick me up early from school so I can meet him? And he did. So this is part two of the interview. I brought you part one earlier in the week.

• 3:06Ryan Holiday?

  But towards the end, as you listen to this, my, my son bursts in and asks Ron some questions. He has Ron sign a book for him and his playbill. And then Ron asks him what his favorite song is and they proceed as I'm sitting in a chair in the corner of the room and I watch Ron Chernow, the author of Hamilton, which inspired like one of the biggest musicals of all time, go through the first song in Hamilton, word for word, with my son, both doing it. And then afterwards, my, my son goes, Dad, I think I knew the words better than him. And it was just a very beautiful thing. And so let me tell you a little story afterwards, though. So I follow up with Ron Chernow and I, I thank him. I'll pull up this email. I said, Ron, thank you so much for making the trip out to the bookstore.

• 3:51Ryan Holiday?

  Most of all, thank you for the incredible consideration you gave my son. He absolutely loved it. I said, I've gotten a lot out of your work over the years. I talked about this in part one. So many of the stories in my books would not be possible without his biography of Washington, his biography of Rockefeller, his biography of Grant, and now his new biography of Twain. I said, but I got the most out of seeing that. Thank you. And he said, it was great to meet you, do the podcast, tour the painted porch, but your son stole the show and my heart. How sweet is that? I'm over the moon. About it. My son was over the moon about it. And then, of course, to go back to Greek mythology, I may have flown too close to the sun because I emailed him back and I said, this is so great. Hey, but while I have your attention, and I guess you'd only get this joke if you read his biography of Twain,

• 4:35Ryan Holiday?

  which is all about Twain falling for schemes and scams and inventions. I said, now that I have your attention, I have an invention I was hoping you'd invest in. It'll be worth millions and millions someday and you can fulfill your dream of being a tycoon. Smiley face emoji. Well, he replied, but he didn't say like, ha ha. And now I'm worried he didn't get it. I'm just worried I blew it like my dad joke flopped. And maybe he seriously thought I was proposing an invention. I definitely was not Mr. Chernow. I love your books so much. Thank you so much. You were incredibly kind. Everyone, please enjoy the second part of this episode and please check out Grant, Washington, Hamilton, and his biography Titan of John D Rockefeller.

• 5:17Ryan Holiday?

  One of the only living biographers to win a Pulitzer, National Book Critics Award, gold medal for biography, a national humanities medal. I mean, he is one of the greats, a living legend. And you'll see in this episode, an incredibly kind person. In part two, we're talking here about why Mark Twain needed stoicism, Twain's moral arc, the tragedy of Twain's life. And then, as I said, towards the end, my son comes in with some pressing questions. I hope you enjoy this interview. I think we still have some signed copies of Chernow's books in the store. They went fast, as it happens, actually, as he went around signing them. Some guy came in and he was a huge Chernow fan. He had read a biography of every American president.

• 6:00Ryan Holiday?

  It had been one of his sort of New Year's resolutions over a couple of years. And so he got signed copies of Grant and Washington. What an experience. You get to listen to it. Enjoy. I'll talk to y'all soon.

• 6:15Ryan Holiday?

  I grew up in Sacramento and, you know, we learned a lot about the sort of mining towns and camps in Calaveras County. So I grew up hearing a lot about Mark Twain and it wasn't until, my parents live near Incline Village now, and I was visiting them, I don't know, eight or nine years ago, I went for a run and I'm running up along this beautiful trail, I'm looking down over the lake and there's this sign, just in the middle of nowhere, like a historical sign and it's like, this is where Mark Twain nearly burnt down all of Lake Tahoe. And I remember thinking, oh, he would have been famous just for this. Like, he would have been the guy that started the Chicago Fire or, you know, was responsible for some natural disaster that we all know about.

• 6:57Speaker 01

  Right. That actually happened. I mean, Lake Tahoe was called Lake Bigler at the time and he went out there with a friend that had bought a small steak there and they spent days just gliding on a canoe. Mark Twain loved nothing more throughout his life than being on the water. And then they're, you know, cooking at this campfire and they managed to set on fire the forest land that they had just bought. This kind of very Mark Twain image that wherever, you know, he goes, chaos follows. Yeah, and it's funny because he then goes out, his first book, The Innocents Abroad, he does this tourist cruise to Europe

• 7:39Speaker 01

  and the Holy Land, you know, they see the Sea of Galilee and he says, you know, Lake Tahoe is much more beautiful.

• 7:45Ryan Holiday?

  Yes, it is. I mean, it's one of the wonders of the earth. When I was reading your Twain book, I was thinking of a quote from Dean Akinson, I think. He was saying that the remarkable thing about Harry Truman was his capacity to change. And Truman's born to slave owning parents, racism, he's part of the system. And from where he began to where he ended up is almost inconceivable, the amount of change and breaking down of prejudice and Twain even more so, because Twain's able to be in a way that I think a president is not more a sort of an activist and a cultural critic. But just, I was blown away at the arc of Twain's sort of moral perspective on humanity.

• 8:30Ryan Holiday?

  It's really.

• 8:31Speaker 01

  Yeah, this is kind of, you know, a big theme in my book because Mark Twain has been so misunderstood about this. Okay, he's born into a slave owning family, you know, in a slave owning state. You read his letters when he's a teenager, it's just full of crude racist jibes, not just about blacks, Chinese. And he just grows and grows and grows. When he marries Libby Langdon, they're an abolitionist family that helped, you know, harbor Frederick Douglass, they knew Wendell Phillips, et cetera. And Twain's views begin to change, you go sort of from being a southerner to a kind of honorary northerner. He then writes up in, still arguably the greatest anti-slavery knowledge and language, whatever its flaws.

• 9:15Speaker 01

  And of course, the N-word is in there many times, but the N-word is used to expose the racism, not to celebrate it, to state the obvious. But then around the same time, something interesting happens, that he visits C.L. Law School. And when he goes there to speak, he meets a brilliant young black law student named Wanertie McGwin. And he writes to the dean, because Wanertie McGwin, even though he was one of the best students in law school, he was living with the black school carpenter and doing odd jobs to survive. Twain writes a letter to the law school dean, offering to pay for all of Wanertie McGwin's expenses.

• 9:57Speaker 01

  And he said, "We have ground all the manhood out of the blacks, and the shame is ours, not theirs, and we should pay for it." And his friend, William Dean Howes, the novelist, said that Twain personally held himself responsible for the harm that the white man had done to the black, and that paying for Wanertie McGwin, it was his form of preparation. He actually used that term. There was also, I discovered, another black student, Wilson, at Lincoln College in Pennsylvania, you know, whom he paid for. And Mark Twain, you know, keeps going further and further. Says, American liberty began not in seventeen seventy six, but in eighteen sixty five, when slavery was abolished.

• 10:41Speaker 01

  He mockingly says, the Declaration of Independence should have said, all white men, you know, are born free and equal. And so he just continues to to grow. And I think that that capacity for growth is true of all the people that I have written about. They all become someone so much greater than you could possibly have imagined.

• 11:07Ryan Holiday?

  Rockefeller goes from caring only about personal profit and maximizing things for himself to this philanthropy, like, you got to grade them on a curve, right? From when they lived and some their peculiar nature of their genius. But there is, if you're not opening up as you get older, then you're closing off. And I think you see this in other powerful, great people, that there, there was something pure and beautiful and wonderful about them when they were young, that's long gone by the time they're at the end. But I think the ones we really admire become more open, more empathetic, more caring, more inclusive.

• 11:44Speaker 01

  Yeah, I think that Rockefeller, you know, kind of ways a lot like, you know, Buffett and Gates, you know, became a bigger figure as a time when I, like, I remember when I was writing the Rockefeller, I was just so fascinated by him. I mean, talk about kind of reason, because he was somebody, you know, in planning any kind of business move or philanthropic move. I think that all of us typically maybe think one or two steps ahead in this situation. He would think like six or seven steps ahead. So he was sort of never, one of his colleagues said, John could somehow not only see far, but could see around the corner. And I remember I got so fascinated by him, I called up my editor and got off and I said, I'd like to do two volumes on John D Rockefeller.

• 12:28Speaker 01

  And she said, pretty much over my dead body. I said, why? And she said, well, if you do two volumes, the first volume is going to be John D Rockefeller, the ruthless monopolist. And then the second volume is going to be John D Rockefeller, the enlightened philanthropist. She said, The whole fascination of this story is that it was the same man.

• 12:47Ryan Holiday?

  Yeah.

• 12:47Speaker 01

  Put it between two covers. And I think that was very, very good advice. So I have always avoided that multi-volume approach because I want you to remember, again, like with, you know, Mark Twain, I want you to remember that kind of, you know, mischievous, often racist, you know, kid running at Hannibal. Do you remember him sort of later on?

• 13:10Ryan Holiday?

  Yeah.

• 13:11Speaker 01

  When he suddenly is paying his reparations, you know, to one or two. And there's a very interesting story with one or two because he goes on to become very distinguished lawyer in Baltimore, argues a famous desegregation case. And there's a young lawyer whom he mentors in the next office named Thurgood Marshall.

• 13:32Ryan Holiday?

  Yeah.

• 13:32Speaker 01

  And Thurgood Marshall, who thought one to me was one of the greatest lawyers he'd ever met, Thurgood Marshall, Chris, then goes on to argue Brown versus Board of Education and become the first black associate justice in the Supreme Court. So I kind of love that through line.

• 13:48Ryan Holiday?

  The coaching tree of of Mark Twain, you wouldn't think leads to Thurgood Marshall, but it does.

• 13:53Speaker 01

  Yeah, to Brown versus Board of Education.

• 14:07Ryan Holiday?

  I'd be curious, what do you think that was in Twain? Is it that the novelist's ability and empathy to see through and into the core of people and things? Or was it some, you know, for Grant, you know, he has like his mother's influence and that's the sort of decency that that is combating against his father's, you know? What is it in Twain that allows him to to not just go from this sort of ruffian, mischievous, Confederate sympathizer to where he ends up, which is? Essentially right on all the big political and cultural issues of his time, far ahead of his time. I mean, he's anti-colonialist, he's anti-slavery,

• 14:51Ryan Holiday?

  anti-racism, anti-income inequality, and then eventually even comes around even to, you know, sort of Native American rights, and he gets it all right in the end, but wasn't there originally.

• 15:02Speaker 01

  I think that, that's a good question, right? I think that part of the answer is just curiosity about people, opening yourself up to people, opening yourself up to what you can learn from other people. I tell the story in the book, of 1874, he used to do a lot of his writing during the summer at his in-laws' place in Elmira in New York. One warm summer evening, they're all sitting on the porch, and there was an older black woman named Mary Ann Cord, who was the cook. She was probably in her 60s or 70s. She had a hearty cheerful manner. Twain was very, very fond of her. And Twain said to her on the summer evening, Auntie Cord, you always have kind of a smile on your face.

• 15:46Speaker 01

  You always have a kind of laughter in your lips. Have you ever had any trouble in your life?

• 15:50Ryan Holiday?

  Doesn't he, he presumed she's never had any trouble in his life. It's actually even more-

• 15:56Speaker 01

  Thank you. You're telling the story better than I am. And then she turns to sarcastically and says, are you in earnest, Mr. C., Mr. Glevins? And she proceeds to tell the most hair-raising story that she had been born into slavery. She had had, in slavery, a husband and seven children. They were all simultaneously sold on the auction block. So at that instant, her husband and seven children were torn away from her. The youngest one, Henry, was the only one she ever saw again. He ended up being a barber, probably Twain's own bar, in Elmira in New York. And then she says to him sarcastically

• 16:35Speaker 01

  again, no, Mr. C., I ain't never had no trouble at all, you know, in my life. And Mark Twain was the first piece under his own signature that ever appeared in the Atlantic Monthly. It was titled, "The True Story," as- Repeated, you know, word for word as I heard it. And I think that it was his ability to kind of draw out the humanity of this woman who maybe had never really told anyone, you know, the story of her life before, you know, and this gave him a picture. He had a very powerful identification with the black community. Strangely enough, even when he was a boy, and in his letters, and kind of terrible racist things, he spent a lot

• 17:20Speaker 01

  of time in the slave quarters.

• 17:22Ryan Holiday?

  Yeah.

• 17:23Speaker 01

  And kind of enjoyed them personally.

• 17:25Ryan Holiday?

  Yeah.

• 17:25Speaker 01

  He thought they were great storytellers. There was a kind of magic and folklore that he loved. And so I think he really liked people and, you know, learned from, from people and that these encounters made a huge impression on him.

• 17:40Ryan Holiday?

  Yeah. And the only reason I corrected you is, is that I was very struck by the story. That there seemed to be something in Twain, his anger was directed at things that he felt people had had the wool pulled over their eyes about, or that they'd been sold a false narrative or story. So it wasn't just that, you know, slavery was wrong.

• 18:03Speaker 01

  Yeah.

• 18:03Ryan Holiday?

  It's that I think he was partly reacting against this, this notion that he'd gotten as a kid, that, that it wasn't wrong, and that it was a positive good. And that it's only as he gets older that he realizes what's been obscured from him as he comes to see the horror.

• 18:18Speaker 01

  Yeah, I know. He said, you know, that in the, the Hannibal of his boyhood, on the subject of slavery, a universal stillness reigned.

• 18:26Ryan Holiday?

  Yeah.

• 18:27Speaker 01

  He described somebody in the streets, you know, white man hitting a black man with a stone, black man dropped dead, you know, no one thought twice about it. And he said that not only did the church not denounce slavery, but he said, we were taught that slavery was sacred and a peculiar pet of the deity. And this creates a lot of cynicism.

• 18:51Ryan Holiday?

  Yeah.

• 18:51Speaker 01

  Not about religion, but about organized religion, because he felt that the, you know, the, the church had been kind of a major, in the South, major prop of slavery.

• 19:00Ryan Holiday?

  Yeah, it's a cynicism against narratives that are telling people they don't have to think too much about something or look too far deep into it. It's like when you go, yeah, aren't sweatshops bad? And then people go, actually, you know, like, and so it's whatever that kind of convenient narrative that that allows something, an injustice or a wrong to continue. It feels like Twain developed a sort of a nose for those things. So, oh, you know, they like us over there in the Philippines, or, you know, the, actually, we were civilizing and helping the Native American tribes. There was a, when he was younger, you know, he accepted all these narratives. And as he gets older and learns

• 19:44Ryan Holiday?

  more and starts to to understand how these things get handled, he has a particular skepticism and a like this focus on on bringing those things into the light.

• 19:55Speaker 01

  Yeah, no, he was able to give up ideas that he'd previously held. You know, when the Spanish American war breaks out, he's actually, you know, a sort of big jingo supporter of it. He because he felt that really we were supporting these Cuban rebels against these Spanish overlords. It's like the American Revolution. And then, you know, in the aftermath, we acquire control over the Philippines. And at first, he naively imagines that we were going to help to establish a Philippine Republic. I said, then he realized that we had gone there to subjugate, you know, not to redeem them. And he was very, very courageous. He gave a speech in New York in which he got up, I think that he was the toastmaster

• 20:39Speaker 01

  to banquet. You know, he got up and said that our soldiers in the Philippines were marching with disgraced muskets under a polluted flag. This is, it's very, very difficult. Takes a lot of courage to criticize. Your government in the middle of a war. In fact, even at the time, you know, a sort of gasp in the audience.

• 21:01Ryan Holiday?

  Yeah.

• 21:02Speaker 01

  And one of the other speakers rushed up to say, no, our boys are not fighting with disgraced muskets under a polluted flag. You know, he lost a lot of friends. And what's interesting is that earlier in his career, major preoccupation, because he always had strong opinions about things. He was very afraid that if people knew what he actually thought about a lot of different things, that he would alienate his readers. But then you see what happens as time goes on, particularly the last 10 years of his life, he just says, the hell with it.

• 21:32Ryan Holiday?

  Yeah.

• 21:32Speaker 01

  You know, I'm gonna let her up. In fact, you know, the famous white suit that he done significantly, he calls the white suit my, I don't give a damn suit. You know, it's like, you all kind of reached that moment in life where we say, you know, I don't give a damn anymore. I'm just gonna say what I felt. And it was a long time coming, you know, for Mark Twain. But eventually, we heard almost everything that he felt come out of his mouth.

• 21:58Ryan Holiday?

  Yeah, there's the tragedy of Twain is of course, you know, what, what could he have said or done had he had a level of financial security, had he not? This is the real cost of ill discipline, right? Is the, I think about this with Thomas Jefferson, right? Like, Washington is able to free his slaves because he had the financial discipline to do so, right? Like, he, he was in a position to realize his ideals, where Jefferson's horrendous spending habits and irresponsibility makes it impossible for, he's just, he's too selfish to do something selfless.

• 22:37Speaker 01

  Yeah.

• 22:38Ryan Holiday?

  And there's probably something about Twain, too, where we lose several good books or stans or whatever, that, that had he, had he been a bit more disciplined and not needed an endless amount of money, so he wasn't chasing these scams, he just would have been creatively and morally.

• 22:57Speaker 01

  Yeah, I think that there are two things, right? You know, one, he and I would say, Levy too, they were very, very attached to material things. Levy actually wrote a beautiful letter in which She said, it's kind of terrible how attached we've become to material things. Twain had made a fortune from his book royalties, from his lecture fees. He married an heiress. They create a 25 room house with six servants in Hartford. So I don't know of any other writer who was living this kind of baronial.

• 23:25Ryan Holiday?

  Yeah.

• 23:25Speaker 01

  You know, existence. And so, you know, Mark Twain, there's so much money there that Mark Twain could have had a very easy placid life, just writing things. But he has a speculative itch. He said, I must speculate, such being my, my nature. And later life, he admits, he said, I was always the easy prey of the cheap adventure. He invests enormously, I mean, in contemporary dollars, millions of dollars, in a whole series of failed inventions. And finally, he invested millions of dollars and Livy's fortune in something called a page compositor that he thought would revolutionize typesetting in the newspaper business. That goes bust.

• 24:09Speaker 01

  He had started his own publishing company, Charles Webster and Company. That goes bust. And, you know, they're forced to give up the Hartford house. They're forced into exile for nine years in order to try to economize. Even then, Ryan, they couldn't economize. And, you know, they're living like in this 30 villa in Florence or this palatial hotel suite in Vienna. They really did not. And in fact, when they're living in this villa in Florence, Livy writes a letter to Sister and says, we're poor as church mice, who just, you know, they have teams of servants. It's really is kind of crazy. So they really were never able to live within their means.

• 24:51Speaker 01

  But the story of Mark Twain is really a tragic story because all of the hardship, the bankruptcy, he has to do this round the world tour to pay off his debts. These are all self inflicted wounds. And interestingly, here's, I think, he was the funniest man in American history, but he said that, he said, life is not a comedy. He said, life is a tragedy with comedy sprinkled here and there in order to heighten and magnify the pain by contrast.

• 25:21Ryan Holiday?

  Yeah. In a way, he and Grant are similar.

• 25:24Speaker 01

  Yeah.

• 25:25Ryan Holiday?

  There's a line from Sherman where Sherman, reflecting on Grant's fall, he said something like, he wanted to vie with fortune. With all these Wall Street figures who would have given all of their money to have won one of his battles. This idea of not being happy with what you have and the poverty of needing to also have what someone else has, it just leads to the end of so many people where it comes at an incredibly high cost because they distract them.

• 25:53Speaker 01

  Yeah, and you know, Mark Twain's first novel was entitled The Gilded Edge. That's where we get the term The Gilded Edge, you know, and it's full of satires of these money mad characters. So someone reading that book, not knowing about his life, would figure out Mark Twain would be the last person in the world who would get caught up in that. He was the first person to get caught up in that. In his writing, he was railing against the plutocrats. In his private life, he's doing everything in his power to become one of them. And what I discovered, you know, with all of these inventions that he invested in, all these business ventures, he wasn't just content to make a decent return. He wanted to make a killing.

• 26:35Speaker 01

  He wanted to become one of the richest people in the country, if not the world. He kept, since when he was in Vienna, he wanted to invest in a new device that would print on textiles and carpets. He's known nothing about this before. In 24 Hours, he thinks he's become, you know, a world historical expert on this.

• 26:54Ryan Holiday?

  There's a need to go to it.

• 26:56Speaker 01

  Yeah, you know, he writes to his friend, Henry Rogers, who was one of the moguls of Standard Oil, and he said, "We should buy up all the patent rights for it. We can control the entire worldwide business." He said, "People will call it a trust, but let them, you know, if they insist," and that he would think in such grandiose

• 27:17Ryan Holiday?

  Yeah.

• 27:18Speaker 01

  terms. I talk in the book, you know, when his siblings were children, their father, John Marshall Clemens, left them with 70,000 acres of largely

• 27:29Ryan Holiday?

  Unfathomable amount of land.

• 27:31Speaker 01

  worthless land, yeah. And the Tennessee land, and he's dying words, "Never give up the Tennessee land. We'll make a rich someday."

• 27:38Ryan Holiday?

  It's his rosebud.

• 27:39Speaker 01

  Yeah, it's his rosebud moment, you know, clearly. And all the children, by Mark Twain, it left this kind of fantasy that we're gonna kind of make a killing.

• 27:49Ryan Holiday?

  Yeah.

• 27:49Speaker 01

  We're gonna strike it rich someday.

• 27:52Ryan Holiday?

  Yeah, it's, um, I'm sure you've experienced this, right? It's like you can do well at what you do. You can have more than you ever dreamed of getting in your life. And then you meet someone and I mean, this is what Twain was going through is very timely in that, you know, then you meet someone and they're like, oh, I made a hundred million dollars speculating in cryptocurrency. And you go, did I screw up somewhere? Like, here I am slaving over these books. And some idiot I went to high school with, you know, makes two entries in a computer and is a billionaire, you know? And that, I think, if you don't have a strong sense of self and you don't love what you do and see that as the gift. Like, that's been striking for me, the number of very wealthy people that I've met,

• 28:37Ryan Holiday?

  that what they really love is books. All they want to do is write books, right? And then you go, oh, okay, you have to remind yourself, like, I hit the lottery. And Twain struggled, I think, to realize he had the ultimate fortune in that he was incredibly rich. And all these rich people admired him and wanted what he has. That's what was the tragedy with Grant, too. It's you were the, you were maybe the greatest general in history. Do you know how many billionaires fantasize about doing what you did for one second? And that the inability to see that and to want what you have and what someone else has, that's the undoing.

• 29:17Speaker 01

  Very well put. Yeah, I mean, you know, Mark Twain had this comic gift. It was once in a generation, kind of, you know, maybe once in a century.

• 29:26Ryan Holiday?

  Yeah.

• 29:27Speaker 01

  Ability to make people laugh, you know, to create characters, to create stories. And anyone would have, you know, traded anything, you know, for that. And yet he was not content with that. He had a kind of contempt for it. You know, early on, when he starts this humor writing, he said, describes this kind of a trait of a low nature. He felt that, you know, wasn't refined.

• 29:53Ryan Holiday?

  Yeah.

• 29:54Speaker 01

  Writing. There's one story that I tell in the book that after a lecture, and he was, again, most brilliant lecturer of his day, or maybe any day. You know, he was with a friend and after the particularly brilliant lecture he gives, Twain is in a foul mood. And the friend asks why, and Twain says, I just entertain them. They'll wake up tomorrow morning. They won't remember a thing. He really felt that he not only wanted to make people laugh, but he wanted to educate them. One strange thing that I found, I think I found it in the, you know, the margin of a book that he owned. He had a self-loathing.

• 30:31Ryan Holiday?

  Yeah.

• 30:32Speaker 01

  Because he read in a book, it said that Byron detested humanity because he detested himself. And Twain wrote in the margin, I'm like that, you know, that, yeah. So there was, there was something in him that he was very dissatisfied with himself and his own life, which is sad because his gift was so singular. You know, and I have to tell you, I, I started writing the, the Twain book, you know, early in the, the pandemic. When a couple of blocks away from me in New York, there was kind of a big refrigerated truck where all the corpses were being kept. And I was so grateful to Mark Twain.

• 31:14Ryan Holiday?

  Yeah.

• 31:15Speaker 01

  First time I've ever done a book where I was literally sitting there laughing out loud as I was doing it. Nobody is, is, is funnier. And, you know, one of the reasons the, the book is so long, I kept discovering these comic gems.

• 31:29Ryan Holiday?

  Yeah.

• 31:29Speaker 01

  And I would sit there saying, you know, Ron, if you don't put it in, it's forgotten forever.

• 31:33Ryan Holiday?

  Yeah.

• 31:34Speaker 01

  If you do put it in, it's going to become part of the Mark Twain lore. And I just think that he had such a priceless gift, but sometimes he did not appreciate that and still wanted something else.

• 31:47Ryan Holiday?

  Well, I think, I think you have a similar gift. I was, I was very upset reading the, the New York Times review. Because I think that the beauty of your books is, it's not just their length, but they're these little things that help you understand the person in a new way. And, and yeah, I imagine each one you accumulated and it means something to you and you have to go, is it going to mean something to someone else? Is it going to matter? Is it going to, is it going to resonate? But it all, they're these deeply layered books that help you understand these figures that I, I think each one of them tells us something about who, who we all are, but then also we need more figures like this in history. There, there's something about biography that's kind of, in our more cynical time, I think,

• 32:30Ryan Holiday?

  like, nobody believes in the great man of history theory anymore, unfortunately.

• 32:33Speaker 01

  Yeah.

• 32:34Ryan Holiday?

  And you need people who think. That they can change the world and do, in fact, change the world.

• 32:40Speaker 01

  No, in fact, you know, whenever people ask me how I choose the subjects of my book, there's kind of a number of different things that I'm looking for. But one, I have to feel that the world is different for this person having lived. And just on that New York Times review, I think that a critic should review the book he's reading, not the book he would like to have read. And it's not, this is not, I should say, the book of Mark Twain. It's not a kind of literary, critical biography where I'm going to sort of go deeply into analysis of each one of the books. What I try to do with the books, and I think actually this is the first biography, I touch on all, two dozen of the books that he published in his life.

• 33:24Speaker 01

  I'm not aware of any other biog- who has done that. But when I come to the books, I try to show that what this reveals about Twain at that moment in his life, you know, what gave rise to it. Also, Twain wrote, you know, a handful of outstanding books, like "From the Mississippi", etc. There are a lot of books that he wrote that are written at a second rate. But, you know, I read them and what I tried to do, I said, you know, no one is ever going to read, I don't know, "The American Claimant", there are all these forgotten books. But sometimes it would be really just a comic gem in the middle of them. So it's going to let me see if I can

• 33:59Ryan Holiday?

  Bring that back.

• 34:00Speaker 01

  Preserve that. But, you know, sometimes a critic will kind of think along with you and then another time they will fight you. Mark Twain made a comment on critics. He said, you know, "It's kind of the degraded, most degraded of all trades." He said, "But the Lord has willed that we have critics and missionaries and humorists and other people and we will have to live, we will have to bear that burden."

• 34:28Ryan Holiday?

  Well, and you'd have to practice your stoicism, which is not let it get to you and just keep doing what you do.

• 34:32Speaker 01

  Well, it's actually, you know, it's funny you should mention that because, you know, I was reading your book on the plane down and when you publish a book, we've now had 31 reviews, of which 28 have been raves. But it's one of those moments where you're especially aware that you cannot control

• 34:52Speaker 01

  Your environment, you cannot control what people say. Tongues will wag. It's not always funny to have all these people sort of chattering about you. And so you have to learn to have a certain philosophic detachment from the whole thing.

• 35:09Ryan Holiday?

  Totally.

• 35:21Ryan Holiday?

  What Stoicism has taught me about being a writer is that my ambition has to be in the book, not in what people say about the book. Right? Like, my ambition is towards the part of it that I control.

• 35:34Speaker 01

  Yeah.

• 35:34Ryan Holiday?

  Like, what I control is, did I do the work? Did I realize what I was trying to do? Did I do my best? You know, it's all in that part. And then you have to be accepting of what other people say and do about it, because you don't control that. You don't have to like it necessarily.

• 35:51Speaker 01

  Yeah, you know, and I've been very lucky around, because I have developed a very, very loyal readership of people.

• 35:57Ryan Holiday?

  I mean, I did the math. I've read 4,200 pages of Ron Chernobyl.

• 36:02Speaker 01

  Well, thank you. You're sort of an example of what I'm about to say. You know, my readers don't particularly care what this, that, or the other reviewer says. And actually, I find, and it's sort of nice going out and doing publicity, because I meet a lot of people like you who are loyal readers, I find, and I get letters from them, I find very often just what, you know, ordinary readers say about the books are, to me, much more insightful.

• 36:28Ryan Holiday?

  Sure.

• 36:29Speaker 01

  Than what the professional reviewers say. And that they appreciate the book in exactly the spirit in which I wrote it. And so I kind of feel very lucky with that. But reviewers will always be with us.

• 36:46Ryan Holiday?

  I read Hamilton close to when it came out and loved it. And my eight-year-old somehow found the musical and is obsessed. So...

• 36:58Speaker 01

  Oh, my goodness, is this your...

• 36:59Ryan Holiday?

  Yeah, Clark, you want to come in? You want to sit in the chair? He's a big Hamilton fan.

• 37:05Speaker 01

  It's a pleasure to meet you. What's your name?

• 37:06Speaker 02

  Clark.

• 37:07Ryan Holiday?

  Did you have any questions?

• 37:09Speaker 02

  Yes. Why did you make a book about Hamilton?

• 37:13Speaker 01

  Well, you'll find this interesting, Clark. I started writing this book in 1998, I suspect, before you were born. And at the time that I started writing about Alexander Hamilton, he was a forgotten figure. No one knew who he was. Maybe they knew he was the guy on the $10 bill. Maybe they knew he had died in a duel with Aaron Burr, but that was it. But I started reading about his life, and I thought it was the most exciting personal story I'd ever encountered. And his achievements were much greater than that of some of the other founders that we knew very well. And so it has pleased me to no end that because of the success of the musical, so many people, Alexander Hamilton is now not only known,

• 37:58Speaker 01

  but is their favorite founding father. Tell me what you like about the musical.

• 38:03Speaker 02

  Well, we read this article, and when they said, "History has a taste on you," they said, "It sounds like God has a taste on you," but they used history because they didn't want it to be religious.

• 38:16Speaker 01

  Uh huh.

• 38:16Speaker 02

  I also have another question that's... When you were writing the book, did you think there would be a musical about it and a play about it?

• 38:27Speaker 01

  That's an excellent question. Hate to say it, Ryan, he should be doing the interview. It's an excellent question. When the book appeared in 2004, it was optioned for a feature film in Hollywood. That is Hollywood would buy the right temporarily to consider doing this. And we had this happen three times. So our expectation was that there would be a feature film of Alexander Hamilton. And then one day in 2008...

• 38:58Speaker 01

  I found out that someone named Lin-Manuel Miranda, who was starring in his first musical on Broadway, which was called "In the Heights", had read my Hamilton book and had become obsessed with it. And I met him. I went backstage. He invited me to his Sunday night. I went backstage. And I said, "So, Lin, I hear my book made an impression on you." And he said, "Ron, as I was reading your book on vacation, hip-hop songs started rising off the page." This was not a typical reaction to one of my books. And he's told me that he wanted to. At that point, he thought it might be just a concept album rather than a full-blown musical.

• 39:41Speaker 01

  And he asked me to be the historical adviser. And I laughed and I said, "You mean, you want me to tell you when something is wrong?" And he said, "Yes." He said, "I want the historians to take this seriously." So I became the adviser to this still nonexistent show. The reason that I said yes to Lin about being an adviser to the show was not because I thought it would be a sensation. It seemed like a very unlikely topic for a Broadway musical. I said yes to him because I'd been a lifelong theater goer. And I thought, "Wouldn't it be fun to watch the development of a show from the other side of the footlights?" And it was one of the greatest experiences imaginable.

• 40:26Speaker 01

  And during the seven years that I worked with Lin on this show, every single person we thought, without exception, thought it was the single silliest idea for a musical they had ever heard. And as Lin likes to say, "They're not laughing now."

• 40:43Speaker 02

  So, basically, when you were writing the book, were you trying to make it interesting?

• 40:49Speaker 01

  Well, I, yes, you know, Chris, I write, as you can see, long books.

• 40:54Ryan Holiday?

  And I think- Listening to the audio book.

• 40:55Speaker 01

  I think that the longer the book, you better make it interesting because no one wants to read a long book, but you have to make this so interesting and so exciting that people will keep turning the pages. And so, you know, the way that I try to do that is by humanizing Hamilton as a character, that he seems like such an extraordinary figure, leading these very dramatic events, that you want to find out what happened next and what happened next. If I can't make him interesting, I can't make a living doing what I do.

• 41:30Ryan Holiday?

  You have anything else, Bud? Then we're gonna walk around the books or you can come with us. Okay.

• 41:35Speaker 02

  Um, so, when you're writing the book, what was like, the hardest part? Like, did you have to look and check a lot of stuff?

• 41:48Speaker 01

  The hardest part of writing the book was that Alexander Hamilton was a human word machine. His papers fill thirty-two very thick volumes, and I had to read all of them. And it was sort of difficult to keep up with just the massive amount of material. It was a little hard on my ego, Clark, to write about a writer who was a much better writer than I was.

• 42:16Speaker 02

  And when you were like, writing the book and doing the history, what was your, like, part of the history that made you laugh, like, the most?

• 42:28Speaker 01

  That made me laugh the most? I don't know in, in, in Hamilton that there were a lot of laughs, exactly.

• 42:35Ryan Holiday?

  I can think of one.

• 42:37Speaker 01

  Can you think of one, right?

• 42:37Ryan Holiday?

  Remember the one about where-

• 42:39Speaker 02

  The parapet.

• 42:40Ryan Holiday?

  Yeah.

• 42:40Speaker 02

  The fat general parapet.

• 42:42Speaker 01

  Remind me of that.

• 42:42Speaker 02

  In the hurricane.

• 42:43Ryan Holiday?

  There was a scene where, I think it's the Battle of Yorktown, where Hamilton is hiding behind a rather large general. He demands that he stop.

• 42:53Speaker 02

  In the hurricane.

• 42:54Ryan Holiday?

  Stop using him as a parapet.

• 42:56Speaker 01

  Oh.

• 42:56Ryan Holiday?

  I thought that was hilarious.

• 42:57Speaker 01

  Okay. See, this is what happens, Clark, when you go out on the road. You discover that your readers remember the books better than you do. You know, I think because my books are long, the hard drive of my brain can only hold one book at a time. You know, and each new book kind of drives out the others. So sometimes I meet someone, they've just finished a book that I wrote 30 years ago, that I've mostly forgotten, and they have the book at their fingertips. And then they can't quite believe that I'm the guy who wrote the book because I seem so dumb and forgetful.

• 43:33Ryan Holiday?

  Clark, I brought your playbill, if you want him to sign it. This is from when we saw Hamilton. I think he wanted to sign it for you, I bet.

• 43:40Speaker 02

  Will you sign this?

• 43:41Speaker 01

  Right, and I think your successor.

• 43:43Ryan Holiday?

  I know, I know.

• 43:44Speaker 01

  Is right here.

• 43:45Ryan Holiday?

  He knows what he's doing. What was your favorite part of the play, Clark?

• 43:47Speaker 02

  Probably seeing Philip for the first time and how bad the hair costume was. How they got like a grown man to play it.

• 43:55Ryan Holiday?

  Oh, to play a kid?

• 43:56Speaker 02

  Yeah.

• 43:57Speaker 01

  What was your favorite song?

• 43:59Speaker 02

  Battle of Yorktown and always Alexander Hamilton.

• 44:03Ryan Holiday?

  You can do it probably from memory. He listens to it every night when you go to bed, right?

• 44:07Speaker 02

  Yes.

• 44:08Ryan Holiday?

  That's when he falls asleep.

• 44:09Speaker 01

  Can you do the first number with me? A desastited orphan, son of a whore and a Scotsman dropped in the middle of a forgotten spot in the Caribbean by providence impoverished in squalor. Grew up to be a hero and a scholar. The ten dollar founding father without a father got a lot farther by working a lot hard, by being a self-starter. By 14, they placed him in charge of a trading charter. And every day while slaves were being slaughtered and carted away across the waves, he struggled and kept his cart up.

• 44:44Speaker 02

  Inside, he was longing for something to be a part of.

• 44:47Speaker 01

  The brother was ready to beg, steal, borrow, or borrow. Then a hurricane came and devastation rained. A man saw his future drip, dripping down the drain. Put a pencil to his temple, connected it to his brain. And he wrote his first refrain, a testament to his pain. Okay, this is what I remember.

• 45:07Ryan Holiday?

  That's amazing. That was so cool.

• 45:11Ryan Holiday?

  You want to show on the bookstore? Yeah. Yeah. No, we'll walk you in, sir.

• 45:20Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it and I'll see you next episode.