Rich Cohen on the Keys to Negotiation | This Is How To Respond to Everything

Ryan reads today’s daily meditation and talks to author RIch Cohen about his new book The Adventures of Herbie Cohen: World's Greatest Negotiator, how to be a great negotiator, his fathers legacy, and more. Rich Cohen is the author of several New York Times bestsellers, including The Chicago Cubs: Story of a Curse and Monsters: The 1985 Chicago Bears and the Wild Heart of Football. Rich is also the author of a book we carry here in the store, Pee Wees: Confessions of a Hockey Parent, where he chronicles the journey of his son’s elite Pee Wee hockey team and his experience as a former player and a devoted hockey parent. This time, Rich and I talk about another father-son relationship - the one he shares with his own father, Herbie Cohen. Rich’s new book The Adventures of Herbie Cohen: World's Greatest Negotiator, which was released last week, is an ode to a remarkable man by an adoring but not undiscerning son, and a treasure trove of hilarious antics and counterintuitive wisdom. Rich is also a co-creator of the HBO series Vinyl and a contributing editor at Vanity Fair and Rolling Stone. He has written for The New Yorker, The Atlantic, and Harper’s Magazine, among other publications. His stories have been included in The Best American Essays and The Best American Travel Writing. Kion Aminos is backed by over 20 years of clinical research, has the highest quality ingredients, no fillers or junk, undergoes rigorous quality testing, and tastes amazing with all-natural flavors. Go to getkion.com/dailystoic to save 20% on subscriptions and 10% on one-time purchases. The Jordan Harbinger Show is one of the most interesting podcasts on the web, with guests like Kobe Bryant, Mark Manson, Eric Schmidt, and more. Listen to one of Ryan's episodes right now (1, 2), and subscribe to the Jordan Harbinger Show today. Novo is the #1 Business Banking App - because it’s built from the ground up to be powerfully simple and free business banking that Money Magazine called the Best Business Checking Account of 2021. This year, get your FREE business banking account in just 10 minutes at bank novo.com/STOIC. GiveWell is the best site for figuring out how and where to donate your money to have the greatest impact. Go to Givewell.org to read more about their research or donate to any of their recommended charities. Enter Daily Stoic at checkout so they know we sent you. Sign up for the Daily Stoic email: https://dailystoic.com/dailyemailCheck out the Daily Stoic Store for Stoic inspired products, signed books, and more. Follow us: Instagram, Twitter, YouTube, TikTok, FacebookFollow Rich Cohen: Homepage, Instagram, See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:06Ryan Holiday?

  Bienvenidos al Daily Stoic Podcast, donde cada semana te enviamos una meditación inspirada por los antiguos estoicos. Una breve pasación de sabiduría antigua diseñada para ayudarte a encontrar fuerza y visión aquí en la vida cotidiana. Y los miércoles, hablamos con algunos de nuestros estudiantes de filosofía antigua, conocidos y obscuros, fascinantes y poderosos. Con ellos, discutimos las estrategias y hábitos que han ayudado a ellos a ser quienes son y también a encontrar paz y sabiduría en sus vidas reales. Pero primero, tenemos un rápido mensaje de uno de nuestros sponsors.

• 0:46Ryan Holiday?

  Esto es cómo responder a todo. La vida nos presenta innumerables situaciones, algunas grandes, otras pequeñas, algunas esperadas, algunas bastante contrarias, algunas dignificadas, algunas pobres, algunas fortunate, algunas desafortunadas. ¿Cómo respondemos a ellas? ¿Podrían ser necesarias estas momentos algo en lugar de una respuesta uniforme? Si sucede, sí. Los estoicos creen que no importa lo que nos dieran, siempre podríamos responder con trabajo duro, con honestidad y ayudando a los demás lo mejor que podemos. Este fue el deber de Marcus Aurelius como emperador, igual que fue el deber de Musonius como exilio en un bosque de madera que coge agujeros. Fue el papel de Seneca cuando recuperó de enfermedad, cuando trabajó en la corte real, cuando se arregló para escribir en sus

• 1:31Ryan Holiday?

  últimos días. No importa quiénes somos, dónde estamos, qué reversión suddenes o bautismo que el destino nos ha concedido. No importa si estamos en medio de una pandemia o un mercado de perros que se esfuerzan. Lo que los momentos nos exigen es trabajo, honestidad y compasión. Buen carácter y actos para el bien común, como dijo Marcus. Toma solace en eso. No importa lo que estés enfrentando, no estás perdido o perdido. Sabes exactamente qué hacer. Y ese es el capítulo que se adaptó en realidad de "El obstáculo es el camino", que puedes comprar una edición de la ola ahora en el store de Daily Stoics o copias firmadas en el store de Daily Stoics o en cualquier lugar donde se vendan los libros si aún no lo has leído. Más de un millón de personas en todo el mundo lo tienen. Espero

• 2:14Ryan Holiday?

  que lo revisen. "El obstáculo es el camino, el arte inmenso de convertir los pruebas en triunfo", mi primer libro sobre estoicismo, y aprecio a todos los que lo han apoyado durante los años.

• 2:27Ryan Holiday?

  I can't believe it was 10 years ago now, but it was. It was at least 10 years ago now. I was in Octavia Books in New Orleans when I lived there. I was just finishing Trust Me, I'm Line. It may have been actually at the first book event I ever did for one of my books. I did a talk at Octavia Books for Trust Me, I'm Line. And I saw this, this book. It was called The Fish That Ate The Whale by Rich Cohen. It's about this guy, Samuel Zemurray, the founder of United Fruit, one of the richest men in New Orleans, one of the most powerful, controversial entrepreneurs of the 20th century, who actually had that big sort of wedding cake house and Audubon place in New Orleans. But it was a whole story I'd never heard of and I loved it. I wrote a little bit about it in The Obstacles Way.

• 3:11Ryan Holiday?

  But more than that book, I just fell in love with the writing of the author. And I since, you know, when you find an author you just love and you read all their stuff. I think I have read almost everything Rich Cohen has ever written. I read Tough Jews, which he wrote after, his book Monsters about the 85 Chicago Bears, his book about the Chicago Cubs, his book Pee Wees about youth hockey. I had him on the podcast a couple, about a year ago or so, also incredible. His book, which he's ghostwritten for Jerry Weintraub, When I Stop Talking, You'll Know I'm Dead. Just seriously, one of the great writers, one of the most prolific writers of our time. And someone I actually interviewed because I wanted to know a little bit more about Zemurray,

• 3:55Ryan Holiday?

  who I present as sort of a cautionary, but also provocative example in The Obstacles, the way, the way he solved problems. I was really interested in his sort of pragmatism. I just, I absolutely love Rich Cohen's work. And I so loved Rich Cohen's work that I read all his stuff. And then I read the book that his father wrote, You Can Negotiate Anything, which I think he published in the 80s. And it was a great book. It changed how I thought about a lot of things, probably up there as the number one or number two best negotiating book of all time. The other being Never Split The Difference by Chris Voss, which is also an incredible book. Anyways, I was so excited that Rich finally Wrote a book about his dad, absurd, larger-than-life character.

• 4:40Ryan Holiday?

  And this new book's called The Adventures of Herbie Cohen, The World's Greatest Negotiator. It was just released last week. You know, Rich Cohen knows how to tell the stories of characters. That's what all his books are about. They're about characters. And I just love Rich Cohen's writing. I was so excited to talk to him. I feel like I owe a debt to him, not just because I loved, and I've used examples from his books in my books, but because he was so generous and kind to me when I was just an unknown writer, writing The Obstacles Away. So I'm excited to bring you Rich Cohen once again. He's written for The New Yorker, The Atlantic, Harper's, among many other publications. He's been included in the Best American Essays and the Best American Travel Writing. I recommended a bunch of his books. I'll link to them in the show notes.

• 5:24Ryan Holiday?

  I would start with The Fish That Ate The Whale. I would read Tough Jews next. I think I might read Pee Wees after that. You really can't go wrong with any of the books. But his new one, The Adventures of Herbie Cohen, about his father, fantastic. Lots of great stories in there. And it's just a sweet book, and we really get into it in this conversation. I think you're gonna like it. You can go to Rich Cohen's website, authorrichcohen.com. You can follow him on Twitter, @RichCohen2003. And you can follow him on Instagram, @author.richcohen. Great, great interview. Enjoy. So I love the new book. I was thinking about it because I loved Pee Wees a bunch, too.

• 6:07Ryan Holiday?

  There's a line you have in the hockey book where you were saying that you were talking to your son's hockey coach, and he was like, "Is your son having fun?" And you were complaining about playing time, or something like this. And he said, "Is your son having fun?" And you said, "Yes." And then he said, "Then what do you care?" Reading about your father, I was curious what you thought he would think if a sports coach had ever said that to you when you were a kid, or said that about you when you were a kid.

• 6:37Speaker 01

  My father truly didn't care about sports, about youth sports. I think it's a generational thing. They never saw it as a serious thing, you know, to them, like, working. I used to ask my father, like, how he completely missed The Beatles. And Elvis Presley and he said, I was too busy working. I had a job. I had a family. And they saw, I mean, sports were fun, but it was, that's a huge change that's happened in the last twenty or thirty years. It's, it's suddenly these things like sports teams seem important. And like what happened seems important. So he would not have cared. Now, he might have cared about other stuff, college or school, but he didn't even show, he didn't even come to my games. He did, he came to one baseball game and two hockey games. And only probably because my mom made him.

• 7:20Ryan Holiday?

  Yeah. So, so if it's not sports, what would he have thought of the idea of the, it's whether you're having fun that counts? Not who wins?

• 7:29Speaker 01

  Well, he did not believe the whether you're having fun thing at all. I should say that. So I used to complain to him that I wasn't happy. And he would say, you're not happy? Good. Happy people have never accomplished anything in the world. It's dissatisfaction that breeds progress. You know, so as he's gotten older, he's eighty-nine, he's mellowed a little bit on that. Uh, but mostly he, he saw unhappiness as a great engine of history. And we should embrace our unhappiness instead of trying to be happy all the time. And being happy all the time was kind of a trap.

• 8:06Ryan Holiday?

  Was, was that hard to grow up with that? Like sort of ethos running through the house? Or do you think it, it informed who you are?

• 8:14Speaker 01

  I think when I was a kid, it was, I had a great childhood, had a lot of fun. And I think because I ignored him. And I thought I was ignoring him, but of course it was seeping it at some deep level. That's come out as an adult. So it was fine as a child, but it's made my adult life definitely harder. You know, I feel like driven by an engine he put into me while I was asleep.

• 8:34Ryan Holiday?

  Yes. You sort of subconsciously pick up on like what a person should be doing? What a person is allowed to let themselves get away with? And like what, what's acceptable? Because that voice in your head of like, do my, would my parents approve of this? Yes or no? Sort of looms there always.

• 8:55Speaker 01

  Like, I'll give you an example. Yesterday I saw, I was driving down the road and I saw like a really cool, like a rocket car, like out of a cartoon, like red two-seater. And I said, wow, that's a cool car. And then I heard my dad's voice go, bullshit car. That's bullshit. Because you can't have a two seater, you got a, you got a family, you idiot. How can you have a two seat car? It's a waste of money. Immediately killed my fun internally. I had the back and forth tennis match and he wasn't even there.

• 9:23Ryan Holiday?

  Yeah, I'd, I'd think about all the things like, you know, I bet that's a, a cost of fortune to take care of. I get, I bet it gets horrible gas mileage. I bet that person actually isn't successful. They're just living way beyond their means. Just sort of like, that is something I think about a lot. I think about the sort of in, internal monologue, sort of the, the throwaway judgments that your parents made about things. How those seep into your consciousness? And like, it's not that they were wrong. It's that, well, some, sometimes they were wrong. Sometimes they should have just kept their mouth shut. But then other times they were right within the context that they lived or their economic circumstances.

• 10:02Ryan Holiday?

  And it's really hard as an adult to go like, yes, that is an appropriate attitude for someone who makes X to have. But if you make five X, you can throw it away on an inefficient car. If you like, it, it's hard to update those scripts in your head.

• 10:16Speaker 01

  But he like, one thing, like I grew up in Chicago and we, you know, some families had a swimming pool. He was very against the swimming pool and he would do the math about how eight months a year, the pool's covered because it's two degrees out. Then it's going to rain another five. So the way he'd figure the math, you can use the swimming pool three days. Three days is what you wind up with, you know? And I think, but what happens with your parents is sometimes they say stuff when you're a kid. And they might not even be serious or they might be not even thinking about it. And it becomes hugely important to you. And I always think a great example of this is in the movie, you know, Talladega Nights. When he's a kid, his father says, you're not first, you're last. And he bases his whole life around it. When he brings it back to his father, he goes, I didn't say that. If I did, I was drunk.

• 11:02Speaker 01

  That doesn't even make any sense. And that's like, sometimes, you know, you take this stuff so seriously and it's, it's not, you know, it's an adult dealing with a kid. So.

• 11:12Ryan Holiday?

  Yes.

• 11:13Speaker 01

  You gotta be careful.

• 11:14Ryan Holiday?

  Have you read, uh, read the novel or watched the movie The Apprenticeship of Duddy Kravitz?

• 11:19Speaker 01

  Oh, of course. It's a.

• 11:20Ryan Holiday?

  It's sort of of your dad, your dad's generation. And you know, he has the, the grandpas like, uh, you're not a man if you don't own any land.

• 11:27Speaker 01

  Right.

• 11:27Ryan Holiday?

  And it's sort of wrecks, like, he ends up, what he ends up doing to get the land to get his grandfather's approval is something his grandfather doesn't, like, you know, the, the, the, the, the penultimate moment of the, of the movie is he's accomplished all the things that he thinks that that generation needs to be proud of him. And then his grandfather doesn't approve because of what he had to do. And, and that, to me, is a warning against internalizing those scripts.

• 11:53Speaker 01

  Right.

• 11:54Ryan Holiday?

  Without the, without balancing them out, I guess.

• 11:56Speaker 01

  Well, I'll give you an example of that, which is one thing my father said he always heard from his great uncle was, uh, land, same Duddy Kravitz.

• 12:05Ryan Holiday?

  Yeah.

• 12:06Speaker 01

  And he quoted a thing, he said, "Women may leave, banks may fail, but good land lasts forever." And my father took this into some extent, and he was, was big into buying real estate, I mean, and did very well on the few occasions that he did. And I recently was researching where that came from, that saying, and it was an ad.

• 12:26Ryan Holiday?

  Yeah.

• 12:27Speaker 01

  It was an ad for like a Long Island housing development, but it was like on a big printed sign. And it's funny because my father's whole thing is about questioning authority. And one of the things he has a lot of suspicion of is our, our big signs. Because they seem like they were printed there by God, but it was just a couple of guys in a room smoking cigarettes, writing it out, you know? So, but basically this thing came down as family lore, and I think it was an ad by the Long Island Expressway, like in the 30s.

• 12:52Ryan Holiday?

  Yeah, and it's, it's weird how if you just take one piece of advice, you build your whole life around it. You, you become this almost cartoon figure. I, I remember, since I worked at American Apparel for many years, and Dove, sort of similar to like the sort of Sweet and Low story that you tell about, one of these like hyper-successful entrepreneurs, but, but profoundly flawed individuals. It was so clear to me, he was sort of almost in this kind of Gatsby-esque or Duddy Kravitz way, where it's like, he wanted to do this thing to impress. These people, but but it it became such a like almost cartoonish pursuit of this thing that thinking that like, hey, when I arrive here, I'll feel good, I'll feel happy, I'll be respected.

• 13:36Ryan Holiday?

  And you you never actually get it that it's it's you're you're like Gatsby after the light, you never get there.

• 13:42Speaker 01

  It's it's it's rece- it's always recedes as you reach it. I'll give you. I've experienced this my whole life, but I'm a massive Cubs fan. You know, I wrote a book about the Chicago Cubs. They won the World Series in 2016 and I wasn't happy, man. I mean, I was glad they won the World Series, but it didn't fulfill me in the way I had expected. And I heard somebody once say, the reason you search for this thing and you reach it and it doesn't make you happy, it's because it's not really what you're looking for. You know, it's a substitute of what you're looking for. What you're looking for is some kind of truth or something, but you can never get the way that you pursue it. You know?

• 14:16Ryan Holiday?

  Well, and I remember I I read Duddy Kravitz because Doug Charney is like, you got to read this novel. It's all about like the it's all about the hustler, like how you should be like he he read the novel and didn't even understand that it was not just satire, but that it was it was criticism. Right? Like Ga- Gatsby is the hero of of The Great Gatsby, but also The Cautionary Tale, right? And we sort of hold up these figures as like, look at what they did. And we kind of we we we don't go like, yeah, but was it worth it?

• 14:46Speaker 01

  Right. But everybody makes that mistake with movies because style is so much more powerful than substance, you know? So every gangster movie, which is posed as a cautionary tale, makes everybody want to live like a gangster. I mean, everybody who reads The Great Gatsby thinks I want to have a lot of different colored shirts and cool cars and drink mint juleps and live out in a big, you know, when of course, that's the totally empty life and he's built it on a completely false premise. You know, but that's never the lesson you get. You always get the lesson of awesome. That's how I want to live.

• 15:16Ryan Holiday?

  Yeah, you forget that he ends up dead in his in his swimming pool and nobody comes to his funeral.

• 15:20Speaker 01

  I mean, think about, think about Goodfellas. I mean, Goodfellas. You want to live like those guys in Goodfellas are the worst guys in the world, then they all wind up brutally murdered or hanging from meat hooks. But the thing that sticks with you is those you want to be one of those guys hanging out, you know, in the nightclub. Sitting at the Copacabana and that overpowers everything else. That's what my father always warned about, that.

• 15:42Ryan Holiday?

  So he learned that lesson, you feel like?

• 15:44Speaker 01

  Well, I feel like he grew up, as far as the gangsters go, I mean, he lived in the neighborhood in the time where they were. And he sort of had more of a realistic view of it. And I grew up in a suburb of Chicago. But I think, you know, one of the things my, one of the things my father did that was good and bad for me is he sort of say what everything, he would always say was bullshit all the time. He never believed the hype about anything to the point where it made it hard to actually enjoy some things. Cause you're like, this is bullshit. This is bullshit. And one of his expressions is always, when you strip away the phony tinsel, underneath that you find the real tinsel. Meaning underneath the fake stuff is more fake stuff. So it's all, it's all a recipe for continually traveling and never quite arriving.

• 16:28Ryan Holiday?

  Yes. Yeah, that's really interesting. Yeah. One of my favorite passages in, in Meditations where Marcus really sees like looking at this feast. And he's like, well, what is all this stuff? He's like, the wine is sort of rotten grapes. And he's like, this is a dead pig. This is a dead bird. You know, it's sort of like that when you strip away the tinsel.

• 16:46Speaker 01

  Yeah.

• 16:47Ryan Holiday?

  You see what's really there, but even that isn't maybe all that it seems.

• 16:52Speaker 01

  Yeah. And you could, you're always searching for the, to finally find the real thing. You know, one thing that he would always, when I would come home from trips, my father, he would always look at my pictures. And I would always take pictures of, you know, Monument Valley in, you know, out west. And with no people and he'd be like, where the hell are the people? Let me tell you, you're not going to care about this picture. Uh, in 10 years about this picture in Monument Valley, it's going to be your friends' faces that you want to see. And that's what you should be taking pictures of. And I think that that's really true. That your only hope is sort of to build it on relationships.

• 17:25Ryan Holiday?

  Well, yeah, flashing forward, obviously your father was very successful. But I remember reading, you mentioned this in some of your other books. Those sort of breakfasts that he would have at Nate and Al's with Larry King and all these people. That seemed like a kind of wealth that not that many people ever actually accumulate.

• 17:45Speaker 01

  Right. But.

• 17:47Speaker 01

  But my father, the thing is, my father grew up with Larry King. His name was Larry Zager. They grew up in Brooklyn and they were little kids together and a bunch of other guys who were in this sort of club gang called The Warriors. And he had all these lessons about how you should live and how an adult should be. And he wrote You Can Negotiate Anything, which was a big bestseller, but it was really, it was a kind of a self-help book. And what I've discovered is like, and I'm sorry dad, but people who write self-help books, in my experience, are the people most in need of self-help. They're sort of

• 18:16Ryan Holiday?

  Of course.

• 18:17Speaker 01

  Talking to themselves in the, in the dark. So when he got around Larry and those guys, he was instantly like a 12-year-old kid again. And he forgot all that stuff and he just was kind of totally living in the moment. And as his kid, it was always a little disorienting. You know, and once he took me to a baseball game and we were on, we got, got to go to the field during batting practice. It's a mid-season game and my father saw Frank Robinson, a player he loved when he was a kid. And he just took off like a kid to go talk to Frank Robinson. And Rick Sutcliffe, who'd been a pitcher for the Cubs and been throwing batting practice, came up to me, saw it happen. He said, did your dad just ditch you because he saw a famous person?

• 19:01Ryan Holiday?

  Yeah, no, as someone who, as someone who writes self-help books, you, if you didn't need the advice, you probably would understand it at some sort of intuitive level that would make you incapable of rendering the advice.

• 19:15Speaker 01

  Right.

• 19:15Ryan Holiday?

  So you're almost always are writing to yourself, you can, it, it's like, um, like if Billy Bean was a better baseball player, he probably would have been a worse manager.

• 19:25Speaker 01

  Right.

• 19:26Ryan Holiday?

  Right? It's that by being, and Michael Lewis talks about this, but by being just not good enough, you're forced to see it and understand it and articulate it in a way that people who are just actually good at it are not even, uh, conceptually aware of. So I, I think that's probably part of it.

• 19:45Speaker 01

  Right. And that I totally, I mean, that's one of the things that fascinates me, like who make good coaches in sports? Good players or bad players? It's, sometimes there's a good player who's a good coach, but it's unusual. Usually like My father started, he was in the army and he worked as a basketball coach for, you know, basically pro players had been drafted and he played basketball, but he was a pretty mediocre to bad basketball player. And that caused him to sort of sit back and analyze and break down the game, which made him a very good coach. And I remember that Ted Williams, like the greatest baseball player of all time, or one of them, was the manager of the, uh, I think the Washington, whatever they were before, the Washington Capitals, the Washington Senators.

• 20:26Ryan Holiday?

  Senators?

• 20:26Speaker 01

  Yeah.

• 20:27Ryan Holiday?

  Yeah.

• 20:27Speaker 01

  And he would, players would be hitting slumps and he would say, well, just hit the ball.

• 20:33Ryan Holiday?

  Yeah, yeah.

• 20:34Speaker 01

  You know, Wayne Gretzky, the same thing, just score. You know, so like it was very hard for them to teach what came to them very, very naturally. So it's the struggle and the figuring out how to overcome the struggle that certain people who are great coaches are able to then relate to players.

• 20:54Ryan Holiday?

  Yeah, I mean, you think about Michael Jordan, incredible basketball player. Also incredible businessman, right? Creates one of the most valuable shoe companies in the world. Really bad NBA team owner. When those two skills should combine perfectly to make you very good at it, but I think probably if you think about what makes a good NBA front office, it's personnel, it's, it's working with other people. It's not just identifying talent, but nurturing talent, getting the most out of not that talented people, which is probably what Michael Jordan was worst at as a player. Uh, he, Kobe Bryant, uh, uh, other athletes where you have this thing where you're just like, why aren't you as good as I am? And it's almost this in inability to comprehend

• 21:38Ryan Holiday?

  why people just don't go into Michael Jordan gear or Kobe gear or want it as bad, almost as unhealthily as Kobe or Jordan does. And then that makes it really impossible to just work with a flawed or a mediocre person, but as part of a larger organization.

• 21:56Speaker 01

  Right. And you look, I told, and you look at the Bulls. You had Jerry Kraus, who Jordan obviously dismissed and didn't like and was short and fat and all that, and was a brilliant basketball guy. And Jordan would go to him, you could go make a list, every year that Kraus made a draft pick, Jordan went with a different draft pick. And said, I want you to draft this person as if it was up to him. And if you look at the team that he would have drafted, they're terrible. Because he was just trying to draft Michael Jordan over and over again, whereas a team needed all these different role players. They already had Michael Jordan, you know, there wasn't going to be another Michael Jordan. So they needed John Paxson and, and all these guys that, you know, that, that Jordan would not have signed necessarily.

• 22:36Ryan Holiday?

  Yeah. Have you read the, have you read the captain's class?

• 22:39Speaker 01

  Yeah.

• 22:39Ryan Holiday?

  By Sam Walker?

• 22:40Speaker 01

  Yeah.

• 22:40Ryan Holiday?

  Yeah. He's like, it's all about Bill Cartwright, not Michael Jordan. It's obviously you don't have the Bulls without Michael Jordan, but Michael Jordan on the Bulls by himself is not that great.

• 22:49Speaker 01

  Right.

• 22:50Ryan Holiday?

  Kobe's kind of the exception because they did win rings after he drove people away, but that's more the testament to Phil Jackson and also the, the exception to the rule where a pretty good athlete, great coach.

• 23:02Speaker 01

  Yeah. No, I think that it's, it's super interesting. Like one of the, I'm a Bulls fan and one of the rubs on Kraus is always, well, he didn't draft Michael Jordan. Jordan was there when he got there, but it's like anybody could draft Michael Jordan. All you had to do was be a basketball fan in the early eighties to know that Michael Jordan was the best player in the world or, you know, very, very, very good. It's the guy who can draft, I don't know, Scottie Pippen, you know, from a little tiny college and no, you know, or Charles Oakley from a little tiny college. That's, that's what the sort of great basketball guy does. He finds kind of hidden value. He's like Sam Zemurray, actually.

• 23:42Ryan Holiday?

  Yes.

• 23:42Speaker 01

  Yes.

• 23:43Ryan Holiday?

  Uh, the, the sort of character, the misfits that end up being the perfect piece in the, in the puzzle.

• 23:49Speaker 01

  Yeah. They're overlooked because people just can't see them. You have to really understand what you're seeing. Like, you know, so you're seeing this incredible player that's at this school that's off the radar.

• 23:59Ryan Holiday?

  So, so going back to your dad, what would your dad think? Cause have all your books been with FSG?

• 24:05Speaker 01

  No.

• 24:07Ryan Holiday?

  Almost all of them?

• 24:08Speaker 01

  Yeah.

• 24:10Ryan Holiday?

  What would he think about that? I would be curious about how he thinks about, how he thought about your career. Because, you know, negotiating contracts, working with agents. How does he think about how you do what you do? Because you're at the highest, you're at a very high level of what you do. How does he think about that?

• 24:26Speaker 01

  I know, he's always suspicious. He always said that the worst career you could pick if you want to like have a family and make money is ballet dancer. And number two is writer. So he was always kind of very skeptical and, and always wanted me to go to law school. This was the thing. I was, I wanted to play in the NHL when I was a kid. He assigned me a favorite hockey player, which was Ken Dryden, who's a goalie for the Canadians, because Ken Dryden had gone to law school and thereby, you know, always had something to fall back on. And even when my first book, which, which was Tough Jews, came out and it was successful, I remember we were walking through Riverside Park and I said, what do you think I'll be doing in 10 years? I was 30.

• 25:09Speaker 01

  And he said, 10 years, you'll be 40, you'll just be getting out of law school. So I think he looks at the whole thing and he, you know, he wrote these two books and he wrote a very successful book, but he wasn't really a writer in that, like he doesn't go sit down and write every day. He's a speaker, a teacher and a storyteller who at some point took a bunch of his stories together and wrote a book in the most ludicrous, insane way possible, which I saw when I was 12 or 11. He went down to our basement, which was an unfinished basement that flooded every time it rained with yellow legal pads and calligraphy pens and by hand wrote this entire book over six months and didn't eat. I think he lost 40 pounds in the process. And making it very hard for him to write another book because he's like, I don't want to go through that torture again.

• 25:54Speaker 01

  You know, he made it so I think that his advice to me has always been, you know, hurry up and go back to law school.

• 26:02Ryan Holiday?

  That's funny. Yeah, I think with my parents, it wasn't until their friends started to be aware of my books that they they got it. Do you know what I mean?

• 26:13Speaker 01

  Yeah.

• 26:13Ryan Holiday?

  It's like, like, because like, there's the, oh, we're proud of you. It's great. But then it's not until it's like something impressive they can talk about to other people that it that it that they stop being so insecure about it, which is partly, I think, what like, like, why do they want kids to be a doctor or a lawyer or whatever? One, they know it's safe. Two, they know it's, you know, it's a profession they they get is like a profession that successful people have. But I think it's always like, I think the most illustrative thing I saw during the varsity blues scandal, that, you know, where they bribed their kids into college, some hedge fund manager was, he's like, look, I just can't have my son go to ASU.

• 26:50Speaker 01

  Right.

• 26:50Ryan Holiday?

  Right? Like, he, it was like, he didn't want to, because that was a shibboleth, is like, I have a dumb kid. Right? Like, like, I have a, I can pay, but my kid didn't get anywhere on his own. Right? And like, I think for a lot of parents, it's like, what doesn't sound like a record scratch when they tell other parents over coffee?

• 27:12Speaker 01

  Right. Well, first of all, it's the same thing with the youth hockey. Who's on the top team? You, I always thought parents were living through their kids and they wanted kids to be better players than they had been and to make the right turn instead of the wrong turn. But it really was about status now. Like, you, you rate, you feel like a higher place in the world if your kid's on a better team. And that's really true for college. The joke is, my father always want, always said, and it could have been a joke, you can never really tell, that he wanted us to go to Yale, one of us to go to Yale. And none of us, I mean, especially me, I was like, didn't do well in school, I was a very mediocre student, I was a dumb kid, kinda. And at one point, much later, he said to me, you know, if you'd worked harder and really

• 27:57Speaker 01

  applied yourself, you could have gone to Yale. And I said to him, he said, if you did better, you could have gone to Yale. I said, no, if you did better, I could have gone to Yale. Because that's my takeaway from like, the varsity blues and everything. You feel like everybody's paying some backdoor in. But there's a really funny thing where I went to New Tru High School outside of Chicago and they're putting together an alumni directory. I went to Tulane, which is a good school.

• 28:20Ryan Holiday?

  Yeah.

• 28:20Speaker 01

  And

• 28:20Ryan Holiday?

  My sister went to Tulane and I wrote my first book there.

• 28:23Speaker 01

  Very fun school to be at.

• 28:25Ryan Holiday?

  Yes.

• 28:25Speaker 01

  So especially if you're from Chicago where it's so cold. And the alumni people called my father and they said, "We're just putting together a directory. Where did your son, Richard, go to school?" And my dad said, "Yale." And they said, "Well, we have down that he went to Tulane." He goes, "Well, you got it down wrong. He went to Yale." And they said, "We have Tulane." He's like, "Then why, if you're so sure, are you even calling me?" They said, "Well, we're just checking." He goes, "Well, you're being corrected. He went to Yale." So in the New Tru directory, it says that I went to Yale. So at least he got that.

• 28:58Ryan Holiday?

  That's amazing. What was the whole thing? Didn't your dad get in a whole fight with the administrators at Tulane?

• 29:05Speaker 01

  Yes, yeah. Well, not the administrators. It was this kind of crazy thing, which is I took a creative writing class with this guy and I don't have any experience with really writing programs. And he was like a guru on the Tulane campus. And he was like, you had to wait to get into his class. And he did this thing, which I'd never seen, where you'd read, he had you read a story, you go around in a circle, and he would just rip you to shreds, try to completely humiliate you. And he had these kind of toadies who'd then join in and amplify whatever he said. And it was just this horrible thing. And it happened to me. It happened to everybody except a few kids who were his favorites. And I'm like, "I want to fight back, but I can't fight back over my own story because I look like a whiner and a crybaby. I'm not doing that."

• 29:50Speaker 01

  So there was a girl that I was friends with outside. She was a business major. She wrote a really good story. He destroyed it. She ran out of there crying. I felt like I should say something to him. And he said his goal in the class was to leave blood on the floor. And then I responded in a really stupid way, which was he had to write a modern poem. And I wrote a poem with all these funky line breaks that just said, "Fuck you, you fuck, fuck you." And read it.

• 30:19Speaker 01

  And that was like persona non grata after that. He just wouldn't even read my stuff. And he gave me a B. So I couldn't complain, but he wasn't gonna read what I wrote. And it really upset me. And I went home over Christmas break and I was telling everybody about it. Told my friends, told my mom, told my dad. He didn't care. Nobody cared. And finally, he said, if I sit down and listen to you for five minutes, you just tell the story and then we just shut up about it. I'm sick of hearing about it. So I sat down and in the course of telling him, I could saw him, I saw him become enraged at this teacher. And the thing about my father is he would get off, especially if he was between gigs or had nothing to do. He looked at all this stuff as kind of a game and he saw himself as out there fighting for justice freelance in the world.

• 31:03Speaker 01

  And he suddenly in his head saw this teacher as somebody that was destroying the creative impulse in people. So he became involved in writing back and forth and fighting with this teacher. And then fighting with the whole English department and then traveling down there. Meanwhile, I had graduated from college and gone off and was living my life. And I didn't even know this was going on and he was still battling this and it was insane. And then he had kind of a heart issue and he went, had to go into the hospital. And I had all these letters. And I said to him, you gotta stop the Tulane thing now. It's crazy. And he said, I will not stop. This is like he's on his deathbed. And he said, and your brother has been briefed.

• 31:45Speaker 01

  And if I should fall in the battle, your brother will continue on and continue waging it. So when it all ended, he got some, you know, stupid little concession, like they put the file in the letter guy's file and he had all these demands. And I said, you see, you spent like five years doing this and what'd you get? You got nothing. You, you got, you got nothing. You lost. And he said, wrong. I won. And I said, how do you think you won? He said, because the next time that teacher is about to destroy a kid, in their head, they'll have a thought, maybe this one's got a greater crazy father too. So that's how he saw it. He was laying down a marker.

• 32:22Ryan Holiday?

  How did that make you feel? Did you like, cause that kind of connects to the, the Pee Wees hockey parent thing. Like the, the parent that, that, that is crazy enough to fight for their kid. It's also probably, uh, completely mortifying. And then also probably a little, uh, inspiring. But then also maybe there's this element where you find yourself like, uh, getting sucked into pointless power squabbles yourself.

• 32:47Speaker 01

  Right, well, I didn't feel it was like the hockey parent thing because it wasn't about me.

• 32:52Ryan Holiday?

  Yeah.

• 32:53Speaker 01

  In that I was out of school and his one demand was that all the kids retroactively be given A's except me. Cause he didn't want it to seem like it was about me. I keep my B. Everybody else gets A's. So I felt like it was crazy, you know? And this is kind of what he was like in that he would get, you know, my, like I said, people who write self-help books are most in need of self-help. So one of my father's big things is the key to success is to care, but not that much, to remain detached, to look at this situation, which you're so worried about and say, it's merely a blip on the radar screen of eternity. And he was great at talking me down when I was upset about something, but he himself

• 33:36Speaker 01

  would have these incidents where it would trigger some value he had or some code would be violated and he would lose all sense of perspective. And it became, you know, entertaining, crazy, but also, you know, you could see why he was sort of telling himself that he shouldn't care that much because the human instinct is to over care. And that's why the hockey thing, cause when it's your own kids, you come, become completely nuts. But with my father, like I said, he didn't care about youth sports. He just didn't.

• 34:03Ryan Holiday?

  But generally he cared a lot and that was probably why he has to write the advice, uh, care, but not that much.

• 34:10Speaker 01

  Well, he has a whole thing where he's great at representing other people in negotiations. One of the best ever, one of the very famous for it. And he was like on the start talks, he negotiated with the Russians over arms. He rep, you know, uh, worked for Carter and for Reagan. He did, did hostage negotiations and this whole thing was because it wasn't his life. He was dealing with and this whole thing like he would say, you know, there was a guy that he was negotiating for and the guy had lost all this money or he had lost it for him. And he said, but the truth is I cared, but not that much. Wasn't my money. Didn't really care. So because of that, he was able to get the guy's money back because he was very free and loose and willing to walk away. So all this is about being able to recognize when basically you shouldn't be negotiating for yourself.

• 34:56Ryan Holiday?

  Cause it does seem like the, the two lane thing. And then when he gets what is every author's nightmare, you get sued for plagiarism.

• 35:03Speaker 01

  Yeah.

• 35:04Ryan Holiday?

  Uh, uh, especially if, if you didn't actually do it. It seems like there were a handful of instances where when it actually involved him or his stuff, he got sucked way in it and he was good enough. He would win, but they were Pyrrhic victories, uh, to say the least.

• 35:21Speaker 01

  Well, the, the, I remember going to jury duty and they asked me if I had any experience with the legal system. And I said, yeah, my father, these lawsuits, cause it was went on for five years. And they said, and how did it work out? I said, well, he won, but it was one of those deals where the trial becomes the punishment. You know, he spent more money on lawyers winning than he probably made on the book and, and gave away. But see, the thing is for him, he knew that the stories in his book were things that came out of his life. I knew there was no plagiarism because those stories, like the first story in the book is about me. I lived it, you know? It was ridiculous. There were family stories and but, and, and his publisher basically said to him, you just gotta settle. When

• 36:03Speaker 01

  a book hits this big, people bring these frivolous lawsuits because you'll just pay them off. And the cheapest thing is a few thousand dollars pay them off. But he thought by paying them off, he would be admitting that he did something he didn't do and it became, but again, he cared way too much. I thought he made the wrong decision. I think just move on, you know? Just forget it, move on.

• 36:27Ryan Holiday?

  I think in the book his lawyer says, "Just pay the parking ticket and go back to your car."

• 36:31Speaker 01

  Yeah.

• 36:31Ryan Holiday?

  That is, I think, really good advice across... Like, the Stoics talk about how there's taxes in life, right? Not the taxes you pay the government, just like, everything... There's taxes to everything. There's a tax to being famous, there's a tax to traveling, there's a tax to being a guy, there's a tax to being a woman, there's a tax to being gay. All the things that you end up being in life, there's a tax, right? And you gotta pay the taxes and move on, pay the ticket and move on. If you get indignant and you take it personally, like, you go, "This is indicting me as a human being, I will not go along with it." That is the... Sometimes you win, but a lot... You usually end up losing even when you win.

• 37:13Speaker 01

  Well, he lost like, five years.

• 37:16Ryan Holiday?

  Yeah.

• 37:16Speaker 01

  You know, I mean, he got it, sorry. But I think part of the problem was that when they... When this happened, it was big news, because the book was such a big hit. And of course, when he won, it wasn't news, because that's not an interesting story anymore. You know? But, so... But yeah, I mean, based on his experience, I believe you just move on, because it's a trap. That's what I think. All the way, traps. Everything's a trap. And the thing is not to get hung up in one of these traps, but to keep moving ahead. You know? I come to see, like, the whole world is like a series of hooks you're trying not to get caught on. And that was a big, big hook that he got caught on.

• 37:56Ryan Holiday?

  See, that's my favorite story in The Fish That Ate The Whale, is Zemurray and... He has the small company then, he's fighting off against United Fruit. And they're trying to buy this land at the border. And, you know, the United Fruit with all the lawyers and all the money is like, "Well, let's see who owns this..." You know, there's... "Who owns the land? Is it this country? Is it this country? Is it this person? This person?" You know, they go back and forth, they're fighting over it. And Zemurray just goes and he buys it from both people. That's its attack, right? "Pay the parking ticket and go back to your car." He's like, "I don't care."

• 38:30Speaker 01

  It's a Gordian knot, man. Just pull out your knife and cut it in half. And usually, my father's like that, actually. And he's very good about seeing things that you don't see. So, one stupid example was, I was applying for a job, just a summer job, I needed a recommendation. I was in college, and I went to my Spanish teacher, and I asked him to write a recommendation, and he said, "Okay." And my father said, "Well, what does the recommendation say?" And I said, there's no way I could know because it's this whole sealed envelope right to the blah, blah, blah. He goes, are you crazy? You can't send a letter out like information's the most important thing you have. This whole thing is you need time, information and power tip. That's his rule for negotiation.

• 39:13Speaker 01

  Information's like one of the most important things and you don't know this. I said, well, how I can't find it. How am I going to find out? He said, tell them that you're applying for an internship at Power Negotiations. That was his business and have them send the recommendation. I just hadn't even thought of that. And I did, and the recommendation was, I'll just say the first line of it was, though Mr. Cohen is not the smartest person in class, it was not a good recommendation.

• 39:39Ryan Holiday?

  Right. It's a, it's the sort of pragmatist approach, not, not being so precious about it and understanding that it's when you make assumptions, oh, this is fine. It's good enough. That's what, what's the, what's the famous thing that you said, uh, till you get, till it kills you? What was that? You had a great line in the book. I forget what it was.

• 40:00Speaker 01

  Time will heal all wounds right up until when it kills you.

• 40:03Ryan Holiday?

  Yeah, yeah, just the idea. It's like, oh, whatever. I don't care, whatever. That, that's great until it gets you.

• 40:08Speaker 01

  Right.

• 40:08Ryan Holiday?

  You know?

• 40:09Speaker 01

  Well, but you know, it's like, I have a friend from college used to always say, those are, those are their rules, not mine. You know? So it's like, that was his, like, that's Tulane's rule. It's not my rule. You know, so as far as the recommendations go. So it's sort of like, and also there's always, I always think of there's more than one way to skin a cat. See, the one great thing about my dad is many great things about him as a father, but one great thing is he, he always felt he was looking at stuff like a strategist and no matter what the problem was, there was a solution. There was always something to do. And that's his whole thing, which is he always thought, wanted people to realize they had power, even if they thought they were powerless. That the whole, his thing from his first book was, power is based upon perception.

• 40:53Speaker 01

  If you think you got it, you got it, even if you don't got it. So, and it was like empowering the, the weak in situations. So there's always freedom and there's always something to do and there's always a move to be made. And he felt, felt when bad things happen, people immediately given to despair and quit. And in fact, that's not the end, that's the beginning. That's when you start to operate and the, the way you should operate is not out of desperation, but fun. It's fun. Look at it as a game. Play it like a game. And it, and if you see it as a game, you'll have fun, you'll live longer, is very big enemy of stress. And actually you'll be more successful because you'll play loose. That makes sense?

• 41:37Ryan Holiday?

  Yeah, no, no, I imagine that gives a kid a, a, a pretty powerful sense of your own agency. Right? First off that like you, when you come to your parents, it's not a dead end. Like, oh, I told mom and dad and now they're mad at me. Right? Which is, I think how a lot of kids feel. Certainly that was my, like if I got in, if I got in an argument with a teacher, I was struggling with something, I brought that to my parents. It was like, I'm, I'm not going to do that because it's just going to add more stress on me. Like it's just, this is just going to get me yelled at or criticized or I'm going to be told how this is my fault. I've got to imagine that for a kid to hear like, oh, well, this is interesting. Let's see what we can do with this corner you've backed yourself into.

• 42:17Ryan Holiday?

  Like, let, let me see what you're working with and let's see where we, how we can't get you closer to where you want to go. That seems like it would be not just inspiring, but in a sense, like bring you closer together because you see your parents as the solutions to your problem as opposed to another one of your problems.

• 42:37Speaker 01

  Right. And one of the things it taught me was like question authority. You know, like just because somebody's in this position older than you, it doesn't mean that they know. And one of the things he always said, one of his favorite quotes is, don't put your trust in princes. And this probably had to do with the fact that, you know, where he grew up, his parents, and he grew up during World War II as a kid. And he saw the whole world fall apart and all these leaders in charge, but they let this horrible thing happen. So basically he had this idea that you, it's the position and the person like if he would meet, he would meet my teachers, I remember. And if it was a teacher that was, knew what they were doing was a good, would not be involved.

• 43:20Speaker 01

  And if the teacher said I did something wrong, okay, and I would get punished. But if he would, you know, something happened that he thought was, you know, unjust or wrong or screwed up, it was an opportunity for him to sort of have fun and test some of his negotiating skills. But what it taught me was if I'd go to him, he was always on my side, always had my back. You know, and um, it did, it gave you a sense of you got to question everything and make your own decisions and reach your own view of things and not accept what's just shoveled down to you.

• 43:56Ryan Holiday?

  Yeah, I wrote down, you had a good line in the book that he said some of the most powerful words a person can say is, I don't understand, help me.

• 44:02Speaker 01

  Yeah. Well, he always said like in a negotiation, everybody wants to appear super smart and like they know better. And he said, the most powerful words in a negotiation are, I don't know. Can you, you know, because you get people actually working for you, he said, and helping you. And he said, you know, sometimes dumb is better than smart. And inarticulate is better than articulate for negotiation. And he always used as an example, his first negotiation, he always said was in the Bible, when Abraham negotiates with God not to destroy Sodom and Gomorrah. And he has a whole thing about Abraham, that that's a power differential. God, Abraham, and he, Abraham uses his weakness to sort of appeal to God's strength to help him.

• 44:48Speaker 01

  You know, so you could actually in some cases use your weakness. Or perceived weakness as a strength.

• 44:54Ryan Holiday?

  Yeah, there's a line from Epictetus. He says, "It's impossible to learn that which you think you already know."

• 44:59Speaker 01

  Yeah.

• 45:00Ryan Holiday?

  And I think about that all the time. It's like where either because you're egotistical and you just go around acting like you're perfect. You know, you, you, you miss all the things that you could learn. But then also when you, you know, you don't know something, but you're too insecure to be like, "Sorry, what was that?" Or like, "Sorry, I didn't understand."

• 45:21Speaker 01

  Yeah.

• 45:21Ryan Holiday?

  Or like, you know, like when someone's like, "Oh, have you ever seen that movie?" And you're like, "Yeah, yeah, yeah, of course." You know, and then that, and then you hope you can pick it up.

• 45:29Speaker 01

  Yeah.

• 45:29Ryan Holiday?

  And then you're like, "I have no idea what this person's talking about, but now I can't admit that, you know, I didn't see The Godfather," or whatever it is, right? And now you, you feel like if you're not comfortable being like, "I don't understand. I don't get it."

• 45:41Speaker 01

  Yeah.

• 45:41Ryan Holiday?

  "Can you explain that to me?" Uh, you, you, you end up often getting yourself in worse trouble than whatever the embarrassment of like saying, "I don't understand" is, or appearing weak is.

• 45:51Speaker 01

  Yeah. Well, he would go around and give these lectures all over the country. And when I was a kid, there were periods where I'd go with him to help him, set up and travel with him. And I'd write him, he'd write on a blackboard, three words, "who?" Question mark, "ha," H U H, question mark, "wa," question mark. He said, "Those are the three most important words in a negotiation." You know, and when you put them together, "who?" "ha?" "wa?" Then you're really got, you're really going good, you know? So basically, he said-

• 46:19Ryan Holiday?

  Because it takes it all the way back down to zero and they're like, "Let's start over and explain this."

• 46:22Speaker 01

  That's right. Also, people try to bull you over with facts and information and their intelligence and their superiority, and it makes them come down to what you're pretending is your level and explain it to you. And one of his things that he really taught me, which I've tried to live by is, if you're, if you're dealing with another person and you're trying to get something, a deal, you actually want to bring them in and come up with a solution together. Because if you come up with a solution together, see, this is what you don't see in politics anymore. If you create the solution together, then both sides have a stake in making it a success. And if you basically get everything you want out of a negotiation and demolish the

• 47:04Speaker 01

  other side, you've humiliated the other side and they have no reason for the agreement to be successful. They have a stake in it failing and it will fail. You know, so a lot of these things is you get involved in these negotiations and they're long and they're drawn out and you don't want, you want to speed to the end. You know, the example is like offering the asking price on a house and by doing that you sort of screw up the whole process and cause the deal to fall apart. For example, if you offer the asking price on a house, which I found out, because you think you're gonna just short circuit everything.

• 47:38Ryan Holiday?

  Just done.

• 47:39Speaker 01

  Just done.

• 47:40Ryan Holiday?

  Sure, we'll take it.

• 47:40Speaker 01

  The first thing that those people think is not, oh great, we sold our house for the asking price. They think, oh no, we didn't ask for enough money. And they start looking for a way out of the deal so they can put it back on the market and make what they think is a lot more money. And ultimately, they might never get that price again and you might not get your house and you both lost.

• 47:56Ryan Holiday?

  Right.

• 47:56Speaker 01

  So you gotta act like they're forcing you to come up, you know, to get to that price. So by the end, they feel like I've gotten every bit of value out of this house I can and I've stretched a little further than I wanted and now they want it to work. And that's like the win-win negotiation.

• 48:12Ryan Holiday?

  Yeah, it's, you would think that being a good negotiator, I think people assume being a good negotiator is like aggressive, firm, unbending, etc. But really, what you're just talking about there is empathy, like not just what does the other person want, but what does the other person feel and how do I make them feel like they're getting what they want, even if actually I'm offering them less money in this, like, like they think they want 500, you're actually helping them get what they want to feel by offering them 495 in a way that you're not by offering them 500. They would rather give 5,000 dollars.

• 48:50Speaker 01

  Right, or he would say, offer them like 400 or whatever. You wind up at 450, let's say. They're happier with 450 than they would be with 500. Which sounds crazy, but it's, it's true and it's, there's a reason why people go through these steps and he used to, there's an, he always went back to literature and there's a play by Arthur Miller called The Price and he used to always paraphrase it. I don't know the exact quote, but it was basically to understand. The price, you have to understand the player. Which means that $500,000 might mean something to you, something to something else. What the person might want might not even be money. Might be something else. So you gotta sort of empathize, he'd say radical empathy.

• 49:35Speaker 01

  Put yourself in that person's shoes. Understand where they're coming for, from, and then you'll understand the price. And one of the really cool things he did in his life is he helped. He worked with this guy Walt Syring to help set up the um behavioral sciences unit at the FBI. Where they would basically make profiles, he did it like was, it became famous for serial killers. But his thing was about hostage negotiation, you know?

• 50:00Ryan Holiday?

  Sure.

• 50:00Speaker 01

  About you understand what's, what's really going on inside the person. So you can understand what they need to end this. You know, and that to understand that, and I always thought he was kind of a thwarted novelist and playwright.

• 50:13Ryan Holiday?

  Your dad?

• 50:13Speaker 01

  Yeah. Cause what he liked to do is look at people, read their situation, try to understand them. And if he could understand them, he could deal with them.

• 50:20Ryan Holiday?

  Yeah, I think about like the Cuban Missile Crisis, which is probably the most high stakes negotiation in human history. And one of the things that always struck me was Kennedy sort of sitting around this conference table. And all these hardliners are like, you gotta do this, you gotta do this, you're gonna look weak, you're gonna look weak. And he has this realization that the same thing is happening to Khrushchev.

• 50:41Speaker 01

  Right.

• 50:42Ryan Holiday?

  And that they're, they're both stuck, right? And that obviously Khrushchev is wrong and obviously Khrushchev has made a mistake. But Khrushchev is now trapped for having made said mistake. And Kennedy's thing isn't, it's not about winning, it's not about who's stronger. It's really how do I, how do I think about what this guy needs to win? Uh, so he doesn't blow up the world.

• 51:06Speaker 01

  Right. And even if he could get Khrushchev to give in without yielding, without giving anything back, without giving him something to tell his people. Then you might solve the problem momentarily, but you'll just have another conflict, it'll just have another conflict later. The most sort of famous example being World War I. The terms of which were so punitive. That they basically caused World War II. You know? You gave, you, you allowed one side to save no face, you humiliated them. Basically, you can't really humiliate people and expect a good long-term result. That's basically what he'd say, I think.

• 51:49Ryan Holiday?

  So if your dad was sitting in these negotiations between Russia and Ukraine, what do you think he would do?

• 51:55Speaker 01

  Well, I think he would understand what you just said about Khrushchev, which is Putin's got himself Putin made a bunch of mistakes. He misread the situation completely and he's already lost. So no matter what happens, he's already lost and he's already greatly weakened. So now you have to give him a way to save face and be able to claim victory if your goal is to end this. You know, if your goal is to utterly defeat Russia and bring them down, that's something else. But see, that will just cause another problem. You know, so I always thought the moving NATO so far east was a mistake. When I was a kid, I was like a European history major. But now that is the situation now. I mean, that's where we live. So you know, that's the starting point.

• 52:40Speaker 01

  But I would think that he would be focused on trying to understand Putin's needs right now. And he might be the devil or whatever, but he's got needs. And he needs a way out and he's stuck. You know, and the fact that he gave this speech today and he didn't make any new demands or anything shows you that he's sort of stuck and looking for a way out. That's what I'm speaking for my father, but that's what I would think. And we got to give him a way out. We got to like leave a door open for him because we don't want a nuclear war, you know?

• 53:10Ryan Holiday?

  Yeah, yeah, there's a thing, I forget which Roman strategist was saying this, but basically it's like, not only will I give the enemy a way out, I'll pave the road.

• 53:18Speaker 01

  Right.

• 53:18Ryan Holiday?

  You know, like, because you'd never want, you never want to be faced with someone whose back is against the wall.

• 53:24Speaker 01

  Right.

• 53:24Ryan Holiday?

  I you think about this, like, let's say you're even your, um, let's say you have this employee who just is the worst, right? You fire that person, you're humiliating them. How do you get that person to quit? Not like by by burning them out, but how do you get that person to say like, you know what? I think I'd be better off somewhere else. Right? Like, how do you get? How do you get them a way to leave so they feel like it's what they like? And they're happy with it and they don't feel humiliated because not only is it do they not deserve to be humiliated because almost nobody does, but that humiliation is going to cost you more than it is them.

• 54:00Speaker 01

  Well, like, look at Russia, even if somehow we could totally shut them down and it would just, there would just be another one of these in a few years. I mean, you want

• 54:09Ryan Holiday?

  It's the biggest country in the world. What are you gonna do?

• 54:12Speaker 01

  Nine, nine time zones or 11 time zones or whatever it is. So you gotta like, and you know, people get emotional. This is my dad's thing. Right now, people on TV, they get emotional. They want Russia destroyed. They want Putin gone. I mean, Biden actually said it, I think, or something like it. And because they're emotional, rightfully so, it's horrible what's happening. It's emotional, but you can't really figure out a solution because the first thing you want is people to stop dying. That's number one. So to do that, you have to give Putin a way to be able to turn to his people and say, we got something out of this.

• 54:47Ryan Holiday?

  Yes, yes. And, and realizing that like, if that person, I, I think what Kennedy also realized in the missile crisis is that one would only make that move out of, uh, out of weakness.

• 55:01Speaker 01

  Right.

• 55:02Ryan Holiday?

  So understanding that, oh, this, yes, the enemy seems very big. Yes, the moves they're making are aggressive, et cetera. But actually fundamentally underneath there is weakness. And so that means time is working for you and against them.

• 55:17Speaker 01

  Right.

• 55:18Ryan Holiday?

  So if you can, you know, it's like

• 55:19Speaker 01

  Well, that's another, yeah, that's interesting. That's another big thing of my father's, which is time.

• 55:24Ryan Holiday?

  Yes.

• 55:24Speaker 01

  Using time to your advantage, slowing everything down. I mean, he was a basketball coach and his expertise was beating good teams with mediocre teams. And he did that by slowing everything down and frustrating the other, the better team. So one of the things he always says is if you want to be successful, you have to live with ambiguity.

• 55:45Ryan Holiday?

  Yeah.

• 55:46Speaker 01

  So you don't know, like if, if you don't want to make, there's a house, you've made an offer, you're waiting. And then a lot of people will get freaked out and call back and bid against themselves and make another offer because they really want the house. When basically, if you could just wait, you'll get your deal. But what that's going to cost you is anxiety and ambiguity. If you don't want that, you don't have to have it, but you have to pay for it. It's going to cost you money. You know, so that's what Kennedy, and the other thing about Kennedy, that, because you bring it up, it's like, he also had to stand up to the crazy right wingers in his own cabinet who were older than him, who had been the, you know, he had been a mid-ranked guy in World War II.

• 56:27Speaker 01

  They had been the generals, the head of the air force, and he had to stand up to them. And that was probably harder than standing up to Khrushchev, to be honest.

• 56:36Ryan Holiday?

  Well, no, and he had gotten bullied by Khrushchev in Europe. Like, he said in his own words that he'd been manhandled like six months. And so, so to, to, to be able to separate, like, hey, I got my ass kicked in round two, but round three is a fresh fight. And I'm not going to carry over my insecurities or lick my wounds in this new round.

• 56:58Speaker 01

  Right. And also, because I've been reading about this same thing coincidentally recently, when he did get his ass kicked by Khrushchev in that meeting, when he went away from it, he didn't take it hugely personally. He kind of chuckled at it. I mean, he realized that it wasn't about him as a person. It was about his experience and his role as president in the United States. And it was kind of like with chagrin, you know, because he brought all these things to the party, which is like his charm, his good looks, his youth, his beautiful wife, you know, all the things that he thought would, and Khrushchev didn't give a crap about any of those things, you know, so it's sort of like, yeah, it's going to have to be something else and in a different way. It's like when you're, even like when you're on the road,

• 57:41Speaker 01

  driving and there's some super aggressive driver, you get mad, you get cut off. And then I always tell myself, this person doesn't know me. It isn't about me. They don't hate me. There's no reason for me to get mad. This is just how this person drives, you know? So.

• 57:57Ryan Holiday?

  Well, I said, I say to myself too, like, I could drive like that. I'm choosing not to because I know it's a really bad idea, right? Like, like, I don't want to die in an accident. That's why I'm not driving that way.

• 58:07Speaker 01

  Yeah. I had a friend in college who said to me, I was, I were in New York and I was running to make it through a light that was turning yellow and there was traffic. And he stopped me and he said, why do you want to live like that? And it kind of stayed with me forever. I really don't want to live like that.

• 58:21Ryan Holiday?

  No, I think about the ambiguity thing. I've talked about this before, but I, I cannot get the Belichick, the Patriot Rams Super Bowl out of my head, where Belichick's like, basically, I'm comfortable playing the ugliest Super Bowl in history. Like, this will be the least interesting, ugliest, most un-football-like football game in history.

• 58:45Ryan Holiday?

  And the Rams were just like, we don't know what to do with this.

• 58:48Speaker 01

  Right.

• 58:48Ryan Holiday?

  This isn't, it was just, they weren't having fun. They weren't doing what they do. And it just destroyed them. But Belichick's like, I don't give a shit what anyone thinks. I don't give a shit that this is the most watched, uh, sports game in history. I, all I care about is like what I think will work in this circumstance. And if you can sit with that, you have so much power.

• 59:11Speaker 01

  Well, that's kind of what he did against the Buffalo Bills this year or two, right? When it was real windy in Buffalo and he just didn't throw the ball.

• 59:18Ryan Holiday?

  He didn't throw the ball at all. You're not supposed to do that. Like you're, you're just for the same reason, you're, you're not supposed to go for it on fourth down. You're not supposed to trade or not sign really expensive player. Like, you know, he, he's just like, I don't care what does the math say? Or what does my gut say? Or what do I want to do? And if you can own that, it's a real.

• 59:38Speaker 01

  Well, see, that's my father. Exactly. So I told you, he's like really a coach. So you gotta figure out the situation and people get prideful about the way they play. And they want to look cool doing it, you know? But if the object is to win the game, then the strategy is going to fit what your personnel is and the situation is. Here's a ridiculous story, which is I had a softball team in a beer league in college and we were losing. We'd been really good the year before and we were losing. And we brought my father in as a coach, mostly because we decided it would be funny. And because my father looked then a lot like Walter Matthau in the Bad News Bears. So we got him a jersey that said, uh, butter maker on the back and everything.

• 1:00:19Speaker 01

  And he took it seriously and he scouted these other teams, which was crazy. It's a beer league softball league and we're in the, one of the final games in the playoffs. He got us, made us much better. He got us there and we're ahead by a run. And we're, we need one out to win, bases loaded, and he calls for an intentional walk. Walking in the winning run. And I went out there and I got a huge fight with him on the mound. I'm like, it's morally wrong to walk in the winning run and it's softball and it's ridiculous. We're not doing it. And because, and I fired him. He always talks about this, because of my role, I fired him. He left and we pitched to the kid and he hit a grand slam homerun and we were knocked out of the playoffs.

• 1:01:05Ryan Holiday?

  I tell a story in the book that I'm doing now about self-discipline. Arthur Ashe's father, author Arthur Ashe Senior, was a driver for this wealthy Jewish businessman in Virginia. And he drives him to a business negotiation one day and he's buying land from this notorious anti-Semite, like this Klan member, basically. And the guy's insulting him and belittling him and saying all this stuff. And the businessman just sort of takes all of it and then walks away, you know, they sign the contract, shake hands, leave. And he says, Arthur Ashe Senior says, "How could you let this man talk to you? Like, what were you thinking?" And he goes, "I wanted the land. I got the land. Yeah, he doesn't have the land anymore."

• 1:01:47Ryan Holiday?

  And both Arthur Ashe Senior and Junior, they're like, "Oh, that's what it takes."

• 1:01:51Speaker 01

  Right.

• 1:01:52Ryan Holiday?

  You know, like, you keep your emotions under control.

• 1:01:55Speaker 01

  And you don't let your ego get involved in it, you know?

• 1:01:57Ryan Holiday?

  Exactly.

• 1:01:58Speaker 01

  Yeah, that's the detachment. That's being able to sort of separate yourself, see it from a distance. And like, you're playing it like a game. And it's just good. One of the things my father did with his book was, before then, because it was published in 1980, it's like a long time ago. People were intimidated by the whole idea of negotiation. Or they thought that it was irreparable. It was like haggling, you know? It was something that you didn't do. Like, you didn't walk into a Sears and try to get a better price on a washing machine.

• 1:02:31Ryan Holiday?

  Yeah, doesn't he open the book with negotiating like a refrigerator?

• 1:02:34Speaker 01

  Yeah, that's one of his things. It's like, because people were, they would never do that. They'd think, "Okay, maybe you negotiate for a used car." Or, you know, but you don't negotiate at a box store. But his whole thing was, you're negotiating all the time. Even if you don't call it that, even if you don't realize it. So, when you're dealing with your family, so he started the book with a story about me who hated to go to restaurants, standing up on a table in the middle of a meal and screaming, "This is a crummy restaurant." And was dragged out of there and not brought to a restaurant for 10 years because I had used my knowledge, which was they feared public humiliation to affect the change that I wanted. And yes, I was punished, but I stayed out of restaurants, which I hated

• 1:03:16Speaker 01

  because I hated eating in the dark and waiting for food for 10 years. So, like with the Sears, one of his rules, which always stuck to me like a like a geometrical formula was...

• 1:03:29Speaker 01

  Anything that's the product of a negotiation is itself negotiable. So when you're looking at a price at a Sears and it looks like it's printed in these big important letters, he would say like that were put there by the big printer in the sky. It's actually itself just a product of a group of people sitting around a room determining a price almost arbitrarily, product of a negotiation you can negotiate.

• 1:03:52Ryan Holiday?

  Yeah, isn't that the Steve Jobs thing that realizing basically everything and all the rules were made up by people that are not any smarter than you?

• 1:03:59Speaker 01

  Right, well, that's the big thing he taught me when I was a kid that probably wrecked my life, which when I would get upset or I'd say I can't do this or I'd be insecure. He'd always say, you know, ninety or he'd say ninety-five percent of the people in the world are schmucks. You know, just keep that in mind. You're not battling a bunch of geniuses here. Just do your thing and you're going to be better off than most people anyway because the world is run by morons. But that was all about this idea of like really questioning authority and not being afraid to sort of put yourself out there.

• 1:04:33Ryan Holiday?

  Yeah, and to go back to that Arthur Ashe story, I think the way you win, the way you get back at the anti-Semite or the racist or the boss that's or whatever is by winning the negotiation. It's not by telling them what you think of them or, you know, tit for tat. It's by getting the thing that you want from them, right? Like, like, let's say he had said something bad back to the businessman or he punched him in the face or whatever it was, like, not only would he not get the land, but that guy would then have confirmation of what he thinks of Jews or black people, whatever it is. So it's like, it's sort of realizing that the way to win is to win, not to let the

• 1:05:16Ryan Holiday?

  person know what you think of them or vomit, you know, Kennedy's not like, and let me tell you what I think of you, Khrushchev. He's like, I'm going to win this negotiation and that's victory enough.

• 1:05:30Speaker 01

  Right, and also.

• 1:05:33Speaker 01

  Playing the long game.

• 1:05:35Ryan Holiday?

  Yes.

• 1:05:35Speaker 01

  You know, like, you're not interested in winning the battle, you're interested in winning the war. So, and that takes patience, which is, it might take ten years for it to be clear that what you've done and what you've done is right, but you wait those ten years. You know, so, that was another thing with my father, he's also a big believer in the long joke. You know, he would set things up that would explode in my face ten years after he set them up. So, you know, it's, it's all about patience and using time. You know, seeing, and all the time, it's like, just, just wait. If you don't like how it is, just wait, because things are gonna look different and things are gonna change. And another big thing for my father was, don't become fixated on what the outcome's gonna be.

• 1:06:20Speaker 01

  Don't go in setting this goal and saying, I have to have this, or I can't have anything. Because, as you deal with people, the, the end, the, the goal can change. And you can wind up with something better than what you went in looking for. So, it's like game theory. He was an early guy, like, arguably, he was the first guy to sort of popularize the phrase, win-win negotiation. And he took it from game theory, which he'd been studying at University of Michigan with a bunch of guys, where they had all these different scenarios, win, lose, lose, lose, lose, win, win, win, win. And the goal is like, the win-win, which is the idea that it's not a zero-sum game. Like, because a lot of people go at it, thinking, for me to win, he has to lose.

• 1:07:04Speaker 01

  And he would sort of say, for me to win in the long term, he has to win.

• 1:07:09Speaker 01

  You know, so, and that's also, like, we were talking about running through the yellow light, like, why, or driving in traffic. It's a better way to live, anyway.

• 1:07:17Ryan Holiday?

  Well, that, that sort of goes ultimately to the Belichick thing, or a lot of these coaches, where, in the end, it's not really fun to be them, or in Belichick's case, he wins all the power struggles, he wins all the games, and Tom Brady's like, but I wanna play football that's fun. You know, and so, you, you end up, you end up winning all the battles and losing the war, or you end up not winning as many battles as you can, because people are like, it just costs too much. It's just, I don't want, I don't want this. And that, that, your dad does seem like, ultimately, had a good life, was fun to be around, had a good family. How many people are great negotiators, cutthroat dealmakers, etc.? And then it is like, it sucks to be you.

• 1:07:57Speaker 01

  Right. I mean, that's one good thing, which is, he really didn't care that much about. He didn't get caught up with his ego about most things. And as a result, he was usually just laughing and having fun. So, and that's what he kind of taught us. Like, one of his big phrases, like, "He who laughs lasts." You know, he believed if you laugh, if you laugh, and it was a very funny house to grow up in. There was a lot of comedy. And if you laugh a lot, you know, ultimately, good things, well, you'll have, you'll have a good life, you know? So, I think that the negotiation for him, the way you negotiate, just became a stand-in for the way you live your life. And you don't want to be somebody who's a cutthroat person who everybody hates, because then you have to live in that world that you created.

• 1:08:41Ryan Holiday?

  Well, and ultimately, care, but not too much.

• 1:08:44Speaker 01

  Right. Exactly.

• 1:08:46Ryan Holiday?

  Amazing, man. Well, I loved, I loved this book. I loved your actual dad's book. And then I think I've read everything you've ever written. So, I love that you keep pumping them out. It keeps me inspired, and they're, they're always amazing.

• 1:09:00Speaker 01

  Thank you very much. I love your work, and I love talking to you.

• 1:09:07Ryan 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.