It Can Change Everything | A Real-Life Example of How to Build a Coaching Tree

Great leaders don’t just build winning teams, they build people who can go on to lead without them. In today’s episode, Ryan talks about the idea of “growing a coaching tree” and what it means to create a culture that outlasts you. Using the San Antonio Spurs as a real-life example, Ryan looks at how the best leaders teach, empower, and develop others, not just for their own success, but for the success of everyone who comes next.📚 Ryan's recommendations: Burning The Days Man’s Search for Meaning Meditations - Marcus Aurelius (Gregory Hays Translation) How To Be A Leader On Character The Way of the Champion Letters to a Young Athlete Moviegoer Mastery 🎥 VIDEO EPISODES| Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail 📢 Share | ⚙️ Manage Subscription

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

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:14Ryan Holiday?

  It can change everything. The right thing at the right time can change everything. Zeno discovered Zenofin's writings on Socrates in Athens and went on to found the Stoic School of Philosophy. I was just there this summer. The Stowe-Poole Hill is where it all began. A young Marcus Aurelius was given a copy of Epictetus's lectures from his teacher's personal library and relied on that book for the rest of his life, even as emperor. James Stockdale was handed the same works by a professor at Stanford, and he'd used what he'd learned to survive seven years as a prisoner of war in the infamous Hanoi Hilton. Aunt Tracy gave me a copy of Man's Search for Meaning when I graduated from high school,

• 0:59Ryan Holiday?

  which in retrospect, set me up perfectly a few years later, when I was turned on to the Stoics. I've been raving about the novels and writings of James Salter lately. If you haven't read his book, The Hunters, it's great. So is his memoir, Burning the Days. But he has this great passage in his novel, Light Years. It says, "The book was in her lap, and she read no further. The power to change one's life comes from a paragraph, a lone remark. The lines that penetrate us are slender, like the flukes that live in river water and enter the bodies of swimmers." When these paragraphs or pages come into our lives, they not only change us, they change the people around us too. How many people learned about Stoicism from Marcus and Stockdale?

• 1:43Ryan Holiday?

  What about the men in that prison camp that were saved by Stockdale's heroism? How many lives have been shaped, even saved, by the ideas from a book, given at the right moment? And I've been thinking about that here. It's graduation season, right? We have young people in our lives, nieces, nephews, sons, daughters, the children of our friends. And it's this entry point. It's a chance for something to enter their life that could stay with them, that could change them. Like, what would you have wanted someone else to hand you at such a pivotal time in your life? Something that could have helped you stay grounded during your first big break or breakup, to remind you that courage and discipline and justice and wisdom,

• 2:28Ryan Holiday?

  the things you needed, they're there for the taking if you know how to develop them. So we thought we'd put together a couple of quick recommendations along these lines to give people you love this graduation season. I'm going to give you a couple, and then I'm going to give you a couple themed lists. I just did one on books I wish I read when I was younger. I think I'll play that for you as well. But look, obviously, Marcus Aurelius' Meditations, this is a book that changed my life at 19. It's one I keep coming back to, one that I picked up on mornings and evenings and afternoons the last two decades. I've read it hundreds of times because every time I read it, I get something new out of it. And I just think there's something immensely powerful about the thoughts of the most powerful

• 3:13Ryan Holiday?

  man in the world. And I got it at the right time in my life. I wouldn't say I wish I got it earlier. I would say I wish more people got it that early. Of course, we have the Leatherbound in the Daily Stoic store. We also have the Daily Stoic box set, which is The Daily Stoic and The Daily Stoic Journal. You can grab all those. Two books I've been raving about recently, How to Be a Leader by Plutarch. Plutarch's actually grandson or grandnephew was the philosophy teacher of Marcus Aurelius. That's pretty cool. He was both a writer, a chronicler of history, and did some of the great biographies of Cato and Caesar, Cato's daughter, Portia Cato, Cicero, Demosthenes, the 300 Spartans. He wrote these great books and essays, mini biographies of some of the greatest men and

• 3:57Ryan Holiday?

  women who ever lived. But he was also a politician himself. I have a whole chapter in Wisdom Takes work about Plutarch as both a writer and a doer. Speaking of which, a related recommendation on character by General Stanley McChrystal. I've loved that. He's a four-star general, and there's a bunch of Stoic advice in there. I've been giving that to a lot of people. Also, just recorded an episode of the podcast with Senator Mark Kelly, and this is like... Literally five minutes ago, I'm walking to the bookstore and this mom comes in. Her son is a, is an athlete and has just gotten into reading. And I gave him a copy of The Way of the Champion by Paul Rabel. And I gave him a copy of Letters to a Young Athlete by Chris Bosch. That's another timely one.

• 4:42Ryan Holiday?

  I was lucky enough to work on both of those books. What else would I recommend book wise? I'm trying to think grad and in, in your life, somebody going through something. Oh, I like The Moviegoer by Walker Percy. That's sort of catcher in the rye for adults. So Good They Can't Ignore You by Cal Newport. You know what? Let me just play the, the other books that I wish I'd read earlier. I'll, I'll, I'll play that for you now. Someone was asking me books that I wish I read when I was 18. I can think of a bunch. I did read Marcus Aurelius's Meditations at 19 and It Changed My Life. I think this is a book every young person should read. So I'd start there. Robert Greene's Mastery is a must read for anyone that age.

• 5:26Ryan Holiday?

  General McChrystal's On Character. As a young person, you're obviously thinking a lot about success. You're thinking about ambition, but you should be spending more time thinking about what kind of person you're going to be. So Good They Can't Ignore You. It's not about finding your passion. It's finding the thing that only you can do. I think every 18 year old should read Autobiography of Malcolm X. Not just the first part, but the second part of the book is the important one. I liked this book recently, Necessary Trouble by Drew Galpin Faust. It's a nice coming of age memoir. Louis Lamour's Education of a Wandering Man. Anyways, that, that's today's episode. The right book, the right time. How can you be the person that enables that? That's what today's episode about. And then let me get you to the rest of the show right now.

• 6:16Ryan Holiday?

  Hey, it's Ryan. Welcome to another episode of the Daily Soak Podcast. Uh, I am exhausted. I just got off the phone with my wife and she was like, I'm so tired. I'm like delirious. We're both exhausted because we, we went to the Spurs game last night in San Antonio and, um, it was an incredible game. I don't know when you're listening to this. This is. We went to game two, which was like a incredible blowout. My kids had an amazing time. They are also quite tired. Well, well past their bedtime, but some of my fondest memories are playoff basketball games. Going to see the Sacramento Kings when I was a kid. And so I had a chance to do that. I've gotten to know the organization over the years. Manu Ginobili has read some of the books. I know R C Buford really well. He's been an awesome supporter of David Stok and the Painted Porch and stuff.

• 6:59Ryan Holiday?

  I was texting him about something because I was watching game one. Or maybe it was the last game of the last series. I forget, but they were like showing the crowd and it was like showing the multi generations of Spurs. Leadership and alumni. And I just sent him a message. I was like, it's so amazing to see that on TV. It's just, it was really inspiring to see like this whole town and community coming together to support the team. He said, you gotta come out to a game. And I was like, I'm not going to ask you for playoff tickets. And he said, no, no, come, send my box, bring your whole family. And so I did. And yeah, sitting there. Manu Ginobili is in the front row. Tim Duncan is right in front of us. Bruce Bowen is there.

• 7:37Ryan Holiday?

  And then I'm, I'm looking down and I'm seeing Brian Wright, the GM, you're seeing Mitch Johnson, the coach, like organizations, for-profit organizations. Politics, life, period. We don't do succession plans very well. There's old TV show about this called Succession, right? But like, other than, you know, Hadrian handing it to Antoninus, handing it to Marcus Realis, there's not a lot of great success stories in history of like. A GM like R C Buford stepping aside so Brian Wright can take over, supporting him. It going well, right? The draft went beyond it, which is incredible. Watching this team go through a rebuild, but not.

• 8:22Ryan Holiday?

  Fall apart in the process is absolutely incredible. Then Greg Popovich, one of the longest serving coaches in NBA history. Having some health issues, getting towards the end of his career, stepping aside, but staying in the organization. So Mitch Johnson can take over, who's now doing incredible. You know, Tim Duncan was briefly an assistant coach, which he was doing largely to support Greg Popovich. Manu Ginobili is still with the organization. Like, all you need to know about the San Antonio Spurs. Is that in their new practice facility, which they just built a couple of years ago, they had to build an alumni locker room. Like even though San Antonio is a small market, even though these players have unlimited money, could live anywhere in the world. So many of them have.

• 9:04Ryan Holiday?

  Stayed in Texas, stayed in San Antonio and still come to the facility, even though they don't, in some cases, work there, but just want to be a part of the organization, want to contribute, want to be around the people. And by the way, the, the team wants them around. It's just an incredible statement about cultural values. And by the way, this isn't just how they treat the players and the coaches. You know, I've had RC on the podcast. He, he came on when we were doing the Daily Stoic Leadership Challenge and I wanted to do deep dive. He's now the CEO of the Spurs organization, uh, which includes the arena and a bunch of other stuff. So it's, he moved up to a bigger job, but it was, it was also fascinating to watch the learning curve

• 9:47Ryan Holiday?

  for that, how, how hungry he was to, to learn and develop new skills. I was talking to someone the other day and who knew RC and I was like, but you're an AI expert. And he's like, yeah, RC wanted to understand how to bring AI into the organization and that's what I'm teaching him. So here's a chunk from that episode, which I think is worth sharing. How do you think about that risk management of like, who do you think we can get to, to buy in? And who is just doing their own thing and they're not a fit for the Spurs?

• 10:17Speaker 01

  I think we're probably more aligned with they're not a fit to the Spurs and haven't taken the, the, the risks that a, an organization like the Patriots have. They've got such structure and stability built up for so many years that there was a structure and a process and a system that they knew how to manage the risks that they did take. Pop's got an expression, they am who they am, which is kind of like, character is, is fate. And, uh, more often than not, your, your risks don't, don't, uh, outperform the reward, would be my guess.

• 10:55Ryan Holiday?

  Well, isn't there a certain amount of ego in that too? The idea that like, we tell ourselves, I'm going to change this person, right? Like, no, everyone else failed because they're not as good as we are. They don't have this, you know, the, the idea that you're going to change someone or reform them. Uh, it can come from a place of compassion, but it can also feel like it comes from a place of ego.

• 11:18Speaker 01

  When you get in the way of yourself, ego is the enemy.

• 11:22Ryan Holiday?

  Yeah.

• 11:22Speaker 01

  You know, Manu brought me that book first and there was so much.

• 11:29Speaker 01

  That when you have failures, there's so much of that that that is apparent in how you get in your in your own way.

• 11:39Ryan Holiday?

  One of the things you and I connected with specifically about Duncan and Tim Robinson, because I wrote a daily Stoic email about it, but to me was a lovely illustration of the Spurs culture. When Tim Duncan was inducted into the Hall of Fame, he was saying, you know, people often ask him, what did David Robinson teach you about leadership and about being a good man and all these things? And he said, I don't think David Robinson ever had a single conversation with me about any of these things. He just embodied it day to day on the court. I just thought that was so beautiful.

• 12:15Speaker 01

  Not even day to day on the court. They both live their lives and hold themselves to standards that raise the standards of everybody around them. In, you know, in 19 years, Tim Duncan was never late once to a practice, to a meeting. He wasn't doing that to demand that of anyone else, but what he demanded of himself raised the standards for all of us. David was very similar. David's impact in our community will live on for years because of the building blocks that he put in place that he'll never see the cathedral eventually finished, but he set such a great example and challenged us all to really care for each other.

• 13:00Ryan Holiday?

  And does that make it easier to create a culture when you have these sort of tent pole individuals who are embodying the ideas? You know, it's like, if if Tim Duncan won't let himself get away with this, who am I? Does it sort of allow you to create a culture around them?

• 13:16Speaker 01

  Well, I think they create the culture. We're people who work with them, but.

• 13:23Speaker 01

  When your best players, when your leaders, when the people who are the examples for your organization and the community, set the culture, then it's up to us, the rest of us, to buy in and to take ownership of it in a way that we all want to build the culture together.

• 13:41Ryan Holiday?

  I think what's fascinating about the Spurs is that, like, obviously, it's a dynasty. Obviously, it's a, it's a place that players wanted to go. I love Texas, but it's a relatively small market team, or it was for many years. How did you create and make San Antonio a destination when, you know, you're not New York City, or Los Angeles, or, or whatever? It, it strikes me as one of the most impressive things that you guys, that you've managed to do it, but create a culture where people not only wanted to come, but I mean, how many, how many players still live in San Antonio? You know, how many players spent their entire careers there? How did you think about creating something both sustainable

• 14:23Ryan Holiday?

  and desirable in, in the market that you were in?

• 14:27Speaker 01

  The sustainability of the success is, is built around the people and the people who others wanted to come play with. And then I think the structure that Pop put in place, the, the community, one great thing about our community is that our community allows these superstar players to live their lives. And they don't have to live reluctantly going through life because they will get overwhelmed. South Texas, Central Texas does a great job of letting people be who they are and supporting and sharing in their success in a, in a non-judgmental and also a non-invasive way.

• 15:10Ryan Holiday?

  Sitting in the box also was a family whose kid worked in the video department. And I remember I was talking to RC one time, and this is going to connect to today's episode, but I was talking to them about the coaching tree of the Spurs organization. I was making the mistake that maybe you're making mentally right now, thinking about the coaches and the players. And he was like, no, no, I'm also really proud of what our salespeople have gone on to do, what our video people have gone on to do, what our stats people have gone on to do, what our marketing people have gone on to do. They see themselves as an organization that makes people, that grabs people that they think have potential, helps them realize that potential and understands that a lot of them are going to go on to somewhere

• 15:50Ryan Holiday?

  or something else and then maybe come back at some point, which is also a key part of sort of the resiliency of the organization is, is that there's such a good landing place for, for talent and for people who have had an off year or have been fired. And people know that the Spurs will let you come back. And so it encourages them to try new things. It encourages them not to burn bridges, encourages them to speak positively about the organization. It just helps their reputation across the board. Anyways, the story I wanted to say is I remember one of the first Spurs games that RC had me come out to, getting the elevator to go up somewhere. And I noticed that the elevator operator has a championship

• 16:30Ryan Holiday?

  ring on. And I go, what's that? And he goes, oh, the organization gives us all rings when we win a championship because we're all contributing. The elevator guy saw himself as part of that Spurs organization, part of their coaching tree, which is what is going to queue up today's episode. Seeing that sitting in that box, our kids getting to be a part of it was just absolutely incredible. And it confirmed something that I wrote about in Right Thing Right Now. I have a chapter in the book about coaching trees, specifically about Popovich, but I'm really speaking about the Spurs organization as a whole. And I wanted to bring you that today because it's something that changed my life. I'm part of the Robert Green coaching tree. People who have worked for me are part of my coaching tree and it's

• 17:14Ryan Holiday?

  changed how I think about success. I want to expand the definition of justice. Justice isn't just giving someone their due, like as far as consequences or whatever. It's how, how we think about what our duties and obligations are as human beings, as leaders, as executives, as entrepreneurs, as athletes, et cetera. So let me bring you that. And I want to thank RC again for the generosity. Also, he was one of the people that, that bought like a hundred copies of Right Thing Right Now when it came out. And he does that for all the books and he gives them away. Just an incredible guy. It was an incredible experience and let's get into it. Grow a coaching tree.

• 17:55Ryan Holiday?

  By all time wins, Greg Popovich is perhaps the greatest coach in the history of the NBA. When one adds to that his number of championships, five, his number of winning seasons, 22, his unbroken streak of playoff appearances, 22, his winning percentage, .657, his Olympic gold medals, two, and the fact that he did it all with one team, he may well be the greatest coach in the history of the game of basketball. But there is another metric besides wins and rings, less considered but more important, that should make the case for him as the greatest coach in sports, his coaching tree. In sports, a coaching tree is defined by the coaches and players and executives

• 18:36Ryan Holiday?

  that a coach has discovered, hired and mentored, and what they go on to do in their own careers. Greg Popovich's coaching tree is so extensive, as one sports writer put it, that it's actually more like a coaching forest. In the course of becoming the longest tenured coach in all of the major professional sports leagues, Greg Popovich would take under his wing multiple Hall of Fame players like Tim Duncan and Tony Parker and Manu Ginobili, who not only made up one of the greatest dynasties in the modern NBA, but stayed in San Antonio and became leaders in their community. At one point, nearly 30% of all the coaches in the NBA had worked for or played under Popovich,

• 19:19Ryan Holiday?

  and his proteges have independently won 11 championships as head coaches and one G League championship. Five times, someone from his forest has been named the NBA Coach of the Year. Of the current 23 black head coaches and GMs in the NBA, seven spent time under Popovich at the Spurs. Becky Hammond, the 2022 WNBA Head Coach of the Year, spent eight years with the Spurs, where she was the first female assistant coach in the NBA and the first to serve as an acting head coach after an ejected Popovich designated her his replacement. And she won two straight WNBA titles as a coach, too. And if one were to begin to trace out the coaching trees from the coaches in Popovich's coaching tree,

• 20:04Ryan Holiday?

  you would touch nearly everyone in the NBA and NCAA basketball. It was this thought that struck Adam Silver, the commissioner of the NBA, during the 2022 Finals, which pitted two coaches whom Popovich had coached, hired and mentored against each other. The Spurs were more than just a basketball team, Silver said. They were practically an academy for future coaches and team executives. If Popovich was running an academy, a nonprofit, mission-based educational organization, these accomplishments would be quite impressive. The fact that he managed to do this while operating at the highest level of a cutthroat game, where he's actually helping, if not producing, the competition?

• 20:47Ryan Holiday?

  This is something he has done outside of his commitment to winning, both as an ideal and as an expectation of his employment. This is not the old boys' club either, with a bunch of people scratching each other's backs, or one leader making identical replicas of themselves. No, it's the act of opening a door, extending a ladder to a diverse group of unique leaders, different types of athletes, coaches, and executives, as they each reach to fulfill their own potential. So as you look at your career, it bears asking, who have you given a shot? Who have you helped get ahead? More revealing how similar to you or unlike you were these people.

• 21:28Ryan Holiday?

  Yet far too often, we are more interested in how to get someone to give us a shot, or how to get another one, or a bigger one, or a better one. We think that by thinking about others, we jeopardize ourselves as if life or work was zero sum. Highlander Syndrome says there can only be one. No, there is room for all of us to succeed, far more to succeed than currently are.

• 22:03Ryan Holiday?

  George Marshall advanced in his career, was able to get to the top of his profession and do well there, precisely because he understood that his job was to help other people, to build an army full of talented officers. While other generals fought tooth and nail for their own advancement, wrote letters to their superiors lobbying for promotions or choice assignments, Marshall was advocating for promising young men like Omar Bradley and George Patton, Walter Kruger, and most of all Dwight D Eisenhower, whom he nurtured into history-defining talents. His coaching tree, you might say, was the oak upon which the Allied victory depended. In this life, of course, we are measured by our accomplishments as individuals. We strive to realize our potential and do our best. But after a certain point, this means only so much.

• 22:49Ryan Holiday?

  What matters more, what matters over a longer horizon, is who we have helped to succeed along the way. To be clear, it's not just sports where a coaching tree counts. Socrates bought us Alcibiades and Xenophon in Plato. Plato, in turn, brought us Aristotle and Aristotle Alexander. Emerson not only generously supported the literary scene in New England, but actively encouraged talent wherever he encountered it. "I greet you at the beginning of a great career," Emerson gushed in a letter to a struggling Walt Whitman in 1855, which Whitman promptly added as a blurb in front of his then undiscovered self-published masterpiece, Leaves of Grass. Without Emerson, the careers of Nathaniel Hawthorne, William Ellery Channing, Amos Bronson Alcott,

• 23:34Ryan Holiday?

  and later William James, Emerson's grandson, and Alcott's daughter Louisa May Alcott would have gone very differently. Generosity is the seed of a great coaching tree. Thomas Wentworth Higginson, in addition to his work as an abolitionist, helped mentor and publish the poetry of Emily Dickinson. Frederick Douglass encouraged and mentored Ida B. Wells, whose anti-lynching work, as well as her work for women's suffrage, and in helping to found the NAACP in 1909, were brilliant extensions of the legacy of Douglass, a man born into slavery in 1818. Martin Luther King Jr.'s legacy is also burnished by the fact that John Lewis went on to become a congressman. Andrew Young became ambassador to the UN.

• 24:18Ryan Holiday?

  Diane Nash won the Presidential Medal of Freedom. Denzel Washington paid for Chadwick Boseman to go to college. Walker Percy was adopted by his uncle Will, and then he in turn was a quiet mentor and teacher to the biographer Walter Isaacson. Percy also discovered and helped publish posthumously John Kennedy Tool's Pulitzer Prize-winning novel, A Confederacy of Dunces. George Carlin met a young Gary Shandling in a comedy club in Arizona in 1968, and after he read Shandling's Jokes Notebook, said, "I think you're funny if you're thinking of pursuing it." Shandling in turn would mentor the director Judd Apatow, Kevin Nealon, Adam Sandler, and Sarah Silverman alongside a generation of comedic talent in the 80s, 90s, and 2000s.

• 25:03Ryan Holiday?

  And what of the people these trailblazers never met but whom their work influenced, whom their example inspired? This is true multi-generational impact, an infinite web of butterfly wings flapped, of lives changed and better futures written. That's the thing, not all of us have the power to change or improve the world within our own lifetimes. By supporting, encouraging, and influencing others, including our own children, our efforts can live on. Mentor, patron, sponsor, ally, teacher, master, guru, inspiration. There are so many names for it, because it's a role defined by so many different roles. But what matters is that we are the candle that lights another, which lights another, which lights another.

• 25:48Ryan Holiday?

  Because through this, whole worlds are illuminated and delivered from darkness.