The Stoic Secrets Great Leaders Use | Daniel Coyle

Summary

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The Daily Stoic Podcast

Episode Title: The Stoic Secrets Great Leaders Use | Daniel Coyle
Date: March 21, 2026
Host: Ryan Holiday
Guest: Daniel Coyle (Author of The Culture Code, The Talent Code, Flourish)

Episode Overview

Main Theme:
This episode centers on the true nature of leadership, challenging the myth of the solitary, heroic leader. Ryan Holiday and Daniel Coyle discuss the Stoic perspective on leadership as a relational, meaning-driven practice grounded in building resilient, connected environments. Coyle’s deep research into elite teams, sports franchises, and high-performing cultures informs a wide-ranging conversation about cultivating leadership, what makes teams flourish, and how vulnerability and collective wisdom override the myth of the lone genius.

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Key Discussion Points and Insights

1. The False Myth of the Solitary Leader

• Timestamp 03:16–04:04
  Ryan introduces the episode's premise: the conventional image of the leader as a lone genius is misguided; Stoicism and Coyle’s research both emphasize the relational and environmental aspects of leadership.

  “Leadership isn’t about pulling levers and controlling outcomes... It’s about building environments where people feel safe, feel connected, like their contribution matters. These are the conditions where teams and communities flourish.” – Ryan Holiday (03:16)

2. Organizations as Living Ecosystems, Not Machines

• Timestamp 04:04–06:23
  Coyle draws on years studying successful organizations, noting that many leaders start with a machine-like control model, only to realize its limits. The flourishing leader creates meaning, nurtures relationships, and provides agency—channeling group energy rather than commanding it.

  “An organization... it has machine-like functions, but ultimately down super deep, it’s a living thing... If you operate like it’s a machine, you can steer, you’ll reach the end, like it will stop working.” – Daniel Coyle (05:04)

• Clear boundaries ("riverbanks") and a directional horizon help channel that energy, but success requires trust and flexibility.

3. The Continual Need for Coaching—at Every Level

• Timestamp 06:33–07:53
  Even top leaders need mentors and coaches. The notion that only developing professionals need coaching is false; continual development is crucial, as shown in organizations like the Cleveland Guardians.

  “The best leaders are always trying to... create a space where they can get insight.” – Daniel Coyle (07:05)

• Experience is necessary, but not sufficient—breadth and willingness to learn from others are critical.

4. Complicated vs. Complex Systems

• Timestamp 07:53–09:29
  Leadership and group dynamics are not “complicated” (like building a watch) but “complex” (like raising a teenager). There’s no fixed set of instructions; adaptation and learning through trial and error is key.

  “Complex things change as you interact with them. So the question asks, is it more like building a watch? Or is it more like raising a teenager?... There’s no set of instructions.” – Dan Coyle (08:07)

• In complexity, progress comes from experimenting, observing emergent patterns, and adjusting.

5. Historical Models: The Apprenticeship of Marcus Aurelius

• Timestamp 09:32–12:47
  The hosts analyze a unique moment in Roman history when Marcus Aurelius was mentored over decades, contrasting this with the disastrous reign of his son Commodus, who rejected mentorship.

  “It’s rare that you get... to control for your variables. But here you have this sort of compare and contrast. It works in one case, and then it doesn’t work in this other case.” – Stephen Hanselman (11:38)

• The lesson: environment, mentorship, and willingness to learn shape leadership outcomes more than inheritance or position.

6. The Power of Relationships and Meaning

• Timestamp 12:58–17:13
  Marcus Aurelius’s gratitude towards his teachers in Meditations is read in detail. The variety of traits he learned—discipline, kindness, flexibility, self-control—illustrate Stoic leadership through apprenticeship and example.

  “He learns compassion, unwavering adherence to decisions, hard work, persistence, listening to anyone who could contribute to the public good...” – Ryan Holiday (15:39)

• Leadership qualities are cultivated, not innate, and relationships are central.

7. Moments of Ignition and Passion

• Timestamp 17:13–19:21
  Coyle and Holiday reflect on pivotal “ignition” moments—like Springsteen seeing Elvis on TV—where passions are sparked. What matters is responding to that spark with effort, not only being “gifted.”

  “What do you do with it? That’s what ultimately matters.” – Stephen Hanselman (18:51)

8. Resilience, Vulnerability, and Growth

• Timestamp 19:22–26:30
  Stories of athletes (notably Jose Ramirez) illustrate that intrinsic confidence and relentless effort, often forged by overcoming adversity, create genuine strength. Vulnerability opens space for growth, and coaches can catalyze growth by waiting for moments of openness.

  “Vulnerability... is what creates relationships. You don’t have to build up trust before you can be vulnerable. It’s the vulnerability that makes it happen.” – Dan Coyle (25:01)

• Leaders (and coaches) are urged to meet people with patience and grace, allowing space for gradual, sometimes painful development.

9. The Shortcomings of Transactional Leadership

• Timestamp 27:01–28:26
  Holiday and Coyle critique industries that treat people transactionally (publishing, pro sports), failing to develop deep, lasting talent. Humility is needed, as predictions of success are often wrong.

  “How many coaches stay with the same team? How many players get shipped... everyone is looking for that short-term success. It prevents you from developing long-term leaders...” – Stephen Hanselman (27:25)

10. Moving Beyond the Solitary Genius—Power of Community

• Timestamp 28:26–30:25
  The myth of individual achievement is debunked; real accomplishment arises from a “latticework” of relationships, mentorship, and shared effort.

  “We can’t stop focusing on the individual and celebrating the individual... but the power of community, it’s like you always see the solitary genius and the lone hero... It’s always way more complex than you think.” – Dan Coyle (28:44)

11. The Danger of Isolation and Hierarchy in Leadership

• Timestamp 29:28–33:26
  Powerful leaders who isolate themselves or discourage dissent (historically and contemporarily) make grave errors. Examples of Hadrian, Putin, and a cautionary tale involving Elon Musk underline the damage done by suppressing feedback.

  “The more isolated you are, the worse you are, because you’re just getting less information and insights.” – Stephen Hanselman (30:07) “The most important words a leader can say are, ‘I screwed that up.’” – Dan Coyle (30:35)

• Creating psychological safety and soliciting honest input are crucial.

12. Relational Attention vs. Task Attention

• Timestamp 35:06–37:20
  Coyle introduces the concept of two battling attention systems in leaders: one focused on tasks and control, the other on relationships and the big picture. Mature, effective leaders learn to switch between them, favoring relationships when needed.

  “The move over and over again is to... surrender that and say, I can’t control everything. I’m just a person in this space. What’s going on here?” – Dan Coyle (36:15)

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Notable Quotes and Memorable Moments

• On Organizations as Gardens, Not Machines:
  • “It’s more like a garden you can grow and cultivate and move in a certain way.” – Dan Coyle (04:04)
• On the Value of Ongoing Coaching:
  • “We think, oh, you need a coach to a certain point in life. But... that point never stops, does it?” – Dan Coyle (06:41)
• On Replica of Mentorship:
  • “Marcus Aurelius’s Meditations... the first, 10 pages are just him thanking his teachers and mentors.” – Stephen Hanselman (13:11)
• The Power of Vulnerability:
  • “It’s the vulnerability that makes it happen.” – Dan Coyle (25:01)
• Creating Space for Feedback:
  • “Creating that space where you’re saying... this is not just safe for you to speak up, but... it’s really important that you speak up.” – Dan Coyle (31:23)
• On Leader Error:
  • “The foremost important words that a leader can say are, I screwed that up.” – Dan Coyle (30:35)
• On Choosing the Right Attention:
  • “There’s this other form of attention—relational attention—where it’s like, oh, I need to pay attention to the sky, to the social fabric... The unlock was that they compete. You can’t have both on at the same time.” – Dan Coyle (35:42)

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Timestamps for Important Segments

• 03:16 – Episode theme: Relationship-based leadership
• 05:04 – Organizations as living things, not machines
• 06:41 – Why even great leaders need ongoing coaching
• 08:07 – Difference between complicated and complex systems
• 11:38 – Marcus Aurelius’s unique apprenticeship compared to Commodus
• 15:39 – Qualities Marcus Aurelius learned from different mentors, read aloud
• 19:22 – Jose Ramirez: confidence, adversity, and forging talent
• 25:01 – Vulnerability as the catalyst for growth and connection
• 27:25 – The problem with transactional talent development
• 28:44 – Community, not individual, creates greatness
• 30:35 – “I screwed that up” – the leader’s essential phrase
• 35:42 – Task attention vs. relational attention in leadership
• 36:15 – The essential move of letting go of control

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Episode Takeaways

• Great leadership is about cultivating environments of meaning, safety, and agency—not command and control.
• Ongoing mentorship, adaptability, and humility are critical for continuous growth, regardless of status or experience.
• True strength in individuals and organizations comes through vulnerability, honest relationships, and sustained, small signals of trust and care.
• The most resilient leaders are those who foster feedback, let go of the need for control, and recognize their own fallibility.
• Culture is built not in grand gestures, but in small, repeated behaviors; leadership is more gardening than engineering.

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Recommended Reading and Resources:

• The Culture Code, The Talent Code, The Little Book of Talent, Flourish by Daniel Coyle
• The Daily Stoic Leadership Challenge (dailystoic.com/leadership)
• DanielCoyle.com

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Transcript

[Ryan Holiday]

Shopping at Whole Foods is one of

[Stephen Hanselman]

the things I do in our family.

[Ryan Holiday]

Like the grocery shopping is my job, so I was glad to be able to do that even on vacation. And then, you know, being here in Hawaii, it was the same Whole Foods experience we're thinking about, but then also a bunch of regional stuff too that they only have at this Whole Foods. We love shopping at Whole Foods because there's always new flavors and foods to

[Stephen Hanselman]

choose from, whichever Whole Foods you are,

[Ryan Holiday]

like whichever Whole Foods you happen to be at. So save on regional flavors at Whole Foods Market and maybe I'll see you at the Whole Foods in Austin sometime.

[Stephen Hanselman]

I know it's not good for me to just run.

[Ryan Holiday]

I need it for my mental health, but it takes a toll on me physically and I need to mix it up. So one of the things I'm trying to work on this year is doing more diverse kinds of workouts and specifically

[Stephen Hanselman]

doing more strength training.

[Ryan Holiday]

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[Stephen Hanselman]

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[Ryan Holiday]

And it helps you lift safely and effectively. Plus, Tonal sets the optimal weight for every move and then adjusts it makes it a tiny bit harder each time in one pound increments as you go and as you get stronger. Right? So you're always challenged, which is one of the other things, right? We gain in our right. Even though we're doing something positive, we're doing it in a way that's actually getting progressively easier instead of progressively harder. So right now, Tonal is offering our listeners 200 bucks off your Tonal purchase with promo code TDS. That's Tonal.com and use promo code TDS for 200 bucks off your purchase. That's Tonal.com promo code TDS for $200 off. Welcome to the Daily Stoic podcast, designed to help bring those four key stoic virtues, courage, discipline, justice and wisdom into the real world. Hey, it's Ryan. And welcome to another episode of the Daily Stoic podcast. Today we're going to be talking about leadership, right? When we think of leaders, we picture that lone figure at the top. The the emperor, the CEO, the head coach, that self made billionaire that the person who got themselves there out of sheer willpower and strength and brilliance and superiority. But that's not how the Stoics saw it. That's not how it is, and that's not what we're going to be talking about today. Dan Coyle has spent years studying what actually makes great teams and organizations work. I was just down speaking to the Chicago Cubs and I was talking to the gm, actually. His name's Carter Hawkins and he had previously been with the Cleveland Guardians. And I asked him if he knew Dan Coyle, and he just went and raved about Dan, who happened to have stopped by the studio not too long ago. You might know some of his books. He wrote the Culture Code, the Talent Code, the Little Book of Talent. He has this new book called Flourish. But basically, his sort of thinking and writing on leadership has taken him inside some of the most successful groups in the world. As I said, elite sports teams, military units, companies, hedge funds. We're all trying to create leaders and cultivate leadership. And so what we're going to focus on in today's episode is something that he and I talked about. Because leadership isn't about pulling levers and controlling outcomes. It's not about genius or superiority. It's actually about relationships. It's about meaning. It's about building environments where people feel safe, feel connected, like their contribution matters. These are the conditions where teams and groups and countries and communities flourish. So let's get into some of that.

[Dan Coyle]

When we talk about leader, there's a mental model that comes in all of our minds that we're kind of entrained on, which is like captain of the ship, right? I'm steering, I'm controlling, I'm in charge of things. And I think a lot of us start out with that model, and a lot of our systems are built with that model. And what happens, at least as I've experienced it in the three books that I've written that connect with this is that most leadership is. Leaders go through this process where they do that for a while, then they reach kind of a turning point and all of a sudden that they realize they have some insight, some road to Damascus, is that the correct road? Some road to mass moment where it's like, this is not working. I'm running it like it's a machine. I'm trying to put levers and get instructions and have measurable outcomes and absolutely push, push, push. And what they do is they let go of the reins a little bit and that's the time when they start cluing into how I would argue the world actually works, which is that it's not a machine. It's more like a garden you can grow and cultivate and have move in a certain way and all the good

[Stephen Hanselman]

organization is not a machine.

[Dan Coyle]

An organization, ultimately it has machine like functions, but ultimately like down super deep, it's a living thing. Right. And if you're going to beat entropy.

[Stephen Hanselman]

Yeah.

[Dan Coyle]

If you're going to like keep surviving and adapting in this changing world, if you operate like it's a machine, you can steer, you'll reach the end, like it will stop working. So what these leaders do is they realize a couple things. The first is that they need to create a sense of meaning and mattering. They need to really have people connect and build relationships. That ends up being area number one. Area number two is they need to design space for agency. They need to create spaces. Organizations aren't machines. They're function more like rivers. Like you need to have clear boundaries. What we're not going to do, yes, Riverbank's going to just stand strong. It's not going to do anything. What we're not going to do, we need to have a gradient like a horizon. We're going toward right. We're going that direction. And anything you do in that space, go do it. Have some agency and the good organization. When you look at the seals, when you look at Pixar, when you look at top performing organizations, what their leaders do inevitably, I think is they create that sense of mattering and meaning which you can think of as almost like that's the connective energy. Like that's the cells that are alive that are connected. And now we're going to channel that energy into this direction. Not here, not here in this space. And now it's up to you guys. Go do it.

[Stephen Hanselman]

We think of the leader as being the sort of the solitary figure, as though the leader is not themselves being

[Ryan Holiday]

led and taught and coached.

[Dan Coyle]

Yeah.

[Stephen Hanselman]

How do you think about that?

[Dan Coyle]

I think it's changing now. It's, you know, I work with the Cleveland Guardians a little bit and a little bit.

[Stephen Hanselman]

I mean, you've been there a long time.

[Dan Coyle]

12 years. 12 years, yeah. Yeah. And we have a coach, Stephen Vogt, he's the best coach in baseball. And somebody asked him, they had a call like, who do you go to for advice? And he goes, well, I have a coach. Right. We think, oh, you need a coach to a certain point in life. But as Dave Epstein has pointed out, that point never stops, does it? Like the best leaders are always trying to. Because It's a challenging job. And because you've got to create a space where you can get insight.

[Stephen Hanselman]

Yes.

[Dan Coyle]

So they're intentionally. And I guess this goes back to the basic principles we're talking about. They're intentionally creating space where they can connect to that meaning and also experiment in directions, kind of rivering their way toward an insight like, oh, wow, that works. I didn't think that would work, but that does work.

[Stephen Hanselman]

And also just someone who's. Who has more reps than you in the thing. Not that they. Not even necessarily that they've done it because some of the coaches aren't actually good at the thing they're doing. Yes, right. Like your swing coach might not actually be a great golfer.

[Dan Coyle]

Oh, man.

[Stephen Hanselman]

But they've worked with hundreds and hundreds of other people. So they've seen all the different swings and they've studied it a thousand. You need your own experience does not have enough breadth to sustain and help you in all the different contingencies that you're going to bump into.

[Dan Coyle]

One of the big eyelashes for me with this, with looking at this stuff has been the difference between complicated and complex. We use that as synonyms. Right?

[Stephen Hanselman]

Sure.

[Dan Coyle]

It ain't complicated. Things come together the same way every time. A set of Legos, instructions to build a Ferrari.

[Ryan Holiday]

A watch.

[Dan Coyle]

A watch. Same every single time. Right. You put it together, you'll get a watch. Complex things change as you interact with them. So the question asks, is it more like building a watch? Is it more like raising a teenager?

[Stephen Hanselman]

Yeah.

[Dan Coyle]

There's no set of instructions. There's no 1, 2, 3, 4, 5.

[Ryan Holiday]

Right.

[Dan Coyle]

And so yet we walk through life because of the way our brains are built. Always sort of seeing machines and the way we're also kind of trained. Yeah, I think we're always looking for machines, always assuming things are machines. We're always looking for that straight line solution that will fix it. Like that will allow us that sense of control that we want. And I think leaders especially, who realize it's not complicated, it's actually complex. We're on this journey of experimenting that's going to take us left and right and around and there'll be new stuff. And when that new stuff appears, I need to be ready for it.

[Stephen Hanselman]

If it's complex, you want as much information as you could possibly have and

[Dan Coyle]

you want to learn by experience. The best. What a mathematician would say is. And complex systems, dynamic theory would say is the best way to learn when it's complicated is find the expert. Like, find the expertise of watchmaker. When it's complex. You actually have to learn through experience. Probe is the word. So do an experiment. Do an experiment, see what happens. And then you'll get what they would call attractors. Like patterns will come up that you notice and you're like, oh, that's cool or oh, that sucks. And then you kind of follow where that takes you.

[Stephen Hanselman]

Yeah.

[Dan Coyle]

And that's kind of how we live our lives actually, when you zoom way out.

[Stephen Hanselman]

Well, it's funny maybe where some of this stuff intersects with what I write about. I'm fascinated by this sort of brief period of Roman history where Hadrian's the emperor and he is having to choose a successor. There's a handful of Roman emperors who don't have sons and they have to choose their successor. So he's having to choose, you know, somebody for a job that only like 15 other people have ever had. And so, you know, who does he pick? And for some reason he picks this kid who would become Marcus Aurelius. You know, a privileged but otherwise, you know, unremarkable person. And he decides to groom him for power. But he understands he doesn't have enough time left. So he adopts this older Roman senator named Antoninus on the condition that Antoninus in turn adopt Marcus Aurelius. So this sort of, he's not just choosing his successor, he's choosing his successor's successor. And he probably thinks that Antoninus is going to live for, I don't know, five years or something. Or maybe he even thinks like at some point Marcus will kill him and then he'll take over. Like just the brutal brutality of the, of the. The ancient world is going to handle this problem. But instead Antoninus lives for two decades and these two men, Marxrelius and Antoninus, who have no affiliation other than they were just thrown together by this guy who they're also not related to, they develop an incredible affinity for each other. So, so Antoninus rules, he takes seriously that he's gonna tutor this kid. And at some point Marcus becomes co emperor again. Like this has never happened before in human history. So Antoninus ruling and teaching, then they're co ruling together. But it's basically this two decade apprenticeship. And then eventually Marcus Aurelius becomes Emperor. And then this is where the story gets interesting. He has a son. His son is Commodus. So one version is Commodus gets a 15 year head start of on the job training, but instead it actually goes horrendous. Like it's as bad as Joaquin Phoenix's character portrays it in God Idea. And so you know what goes wrong. So it's. It's rare that you get. Because history is not a science experiment. You don't get to control for your variables. But here you have, like, this sort of compare and contrast. It works in one case, and then it doesn't work in this other case. I'm just endlessly fascinated with, first off, the idea of, like, actually saying, like, hey, I want to learn everything I can about this job I'm about to take.

[Dan Coyle]

Yeah.

[Stephen Hanselman]

And then, you know, how somebody else who decides not to do it, it goes so terribly.

[Dan Coyle]

It makes me think of so much. The NFL coaching trees.

[Stephen Hanselman]

Right.

[Dan Coyle]

Though sometimes it go really well, sometimes they do not. Right, right. And the apprenticeships of the Renaissance. Right. These long periods where it was just. This is craft. You might be painting the Sistine Chapel, but you know what? You got to get your reps. You

[Stephen Hanselman]

think you're ready, you're not even close enough. You're not even flush. Ready in 20 years. Yeah.

[Dan Coyle]

Let's hang out. You're going to mix some paints for a while. Right. It's that. And so that ends up being. I think it gives you a clear vision on how talent is actually grown. And also especially that motivational piece.

[Ryan Holiday]

Yes.

[Dan Coyle]

You know, the kid who's born into, hey, I've got this great mentor, and I'm gonna spend 20 years with him versus the kid who's just born thinking, hey, silver spoon, I've got it. I'm next in line. I'm good.

[Stephen Hanselman]

It's like, potential could be biological or genetic.

[Ryan Holiday]

Yep.

[Stephen Hanselman]

Because you're. You're born in this position or not. You're this height or this height. You have this fast twitch, muscle fiber, or you don't. But then everything from there, the swing vote is, do you cultivate it? Do you do the work?

[Ryan Holiday]

Do you have the teachers?

[Dan Coyle]

Right.

[Stephen Hanselman]

Do you follow the tradition?

[Dan Coyle]

Which ends up looking not like a machine, but like an ecosystem in that you have to have a source of energy for it.

[Stephen Hanselman]

Yes.

[Dan Coyle]

Commodus maybe wasn't psyched to do that role. Maybe he was psyched about something else.

[Stephen Hanselman]

Well, we're told by this one ancient historian that. That Mark is sort of aware of this. One of the interesting things about Marc Soros's Meditations is The first, like, 10 pages are just him thanking all his teachers and mentors. And he says one of the things he learns from Antoninus is to always cede the floor to experts to learn from other people. Were told by a historian who lives through Commodus reign that Marcus Selects a group of people, not just one senator, but he says, the best men in the Empire, to teach this person. And that at some point very early on, Commodus goes, nah, you know, I don't want to listen to the old guys anymore. And that is to me, probably the, that's the critical divergence.

[Dan Coyle]

Isn't that crazy to think about? Like, one morning he gets up and he's kind of sick of it. And that emotion ends up changing the

[Stephen Hanselman]

course of human history. I mean, that is the decline and fall of Rome begins there, begins with that moment Tax Romana, ends with Commodus. And you know, the end of the Empire, you could argue, ends with him too, because, yeah, you know, one guy decides he's a know it all and therefore knows all there is to know.

[Ryan Holiday]

One of the things that, that Dan and I were talking about is how Marcus Aurelius thanks his mentors in Meditations. But let's actually read what some of Marcus thanks those mentors for getting out. This is my leatherbound copy of Meditations. It's actually the one, if you've ever seen me do my talks, is the one I tend to bring on stage. Here's what Marcus Realis thanks Rusticus for the recognition that I needed to train and discipline my character. Not to be sidetracked by my interest in rhetoric. He says to read attentively and not be satisfied with just getting the gist of things. And did not fall for every smooth talker. Here's what he thanks Apollonius for independence and unvarying reliability. To pay attention to nothing, no matter how fleeting, except the logos. And to be the same in all circumstances. Intense pain, loss of a child, chronic illness. And to see clearly from his example that a man can show both strength and flexibility. He thanks Sextus for teaching him kindness, to display gravity without errors. He thanks his rhetoric teacher Fronto for teaching him how to recognize the malice, cunning and hypocrisy that power produces. And of course, from Antoninus, greatest teacher, he learns compassion, unwavering adherence to decisions, indifference to superficial honors, hard work, persistence, listening to anyone who could contribute to the public good. A sense of when to push and when to back off. His searching questions at meetings, kind of single mindedness, almost never content with first impressions or breaking off the discussion prematurely. His constancy to his friends, never getting fed up with them or playing favorites. Self reliance always and cheerfulness. His constant devotion to the Empire's needs. His stewardship of the treasury, his willingness to take responsibility and blame the way he handled the material comforts that fortune supplied to him in such abundance, without arrogance and without apology. If they were there, he took advantage of them. If not, he didn't miss them. But most of all, I am struck by what he learns from Maximus. I actually just read this one on stage the other day. From Maximus, he learned self control and resistance to distractions. Optimism in adversity, especially illness. A personality in balance, dignity and grace together, doing your job without whining. Other people's certainty that what he said was what he thought, that what he did was done without malice, never taken aback or apprehensive. Neither rash nor hesitant or bewildered or at a loss. Not obsequious, but not aggressive or paranoid either. Generosity, charity, honesty. The sense he gave of staying on the path rather than being kept on it. And those are just a couple of the things he thinks. But back to me and Dan.

[Dan Coyle]

Springsteen's been in the news lately and it's like he talks about the moment he saw Elvis on the television. Yeah, like the moment, right. These moments of ignition, and they're not about information. They're not about, like learning some fact or seeing some person. It is about this energized relationship where you are, you find yourself mattering, you find this sense that you're seeing some immense value, some enchanted circle. And those moments, I think they happen all the time and they end up driving these big things that happen both in history and in our lives individually and cluing into them. As a parent, I think about that a lot. As a community member, I think about that a lot. As somebody who's in a high performing organization, it's like, how do we cultivate those. Where did that happen? And I can't help but wonder, where did that happen for you? Because you got lit up at a pretty young age.

[Ryan Holiday]

I did.

[Stephen Hanselman]

I mean, someone handed me the ideas from the Stoics and I was like,

[Ryan Holiday]

oh, where's this been?

[Stephen Hanselman]

I'm in and I'm in.

[Dan Coyle]

Go back an inch. But what led you to be in?

[Stephen Hanselman]

What led me to see it? Or what led me to craving?

[Dan Coyle]

Why were you craving? What itch did it scratch for you? Or where did it. Where did it resonate?

[Stephen Hanselman]

Why one thing lights us up and another doesn't? I think there is. I do think there's something sort of otherworldly about. I don't know how much choice we have over that.

[Dan Coyle]

Like, you saw Elvis through the tv.

[Stephen Hanselman]

Yeah, I think, yeah. There's just some. Sometimes it lines up like, why this person loves physics and this person loves, you know, physical education. You know, who knows? But like the decision to me that's interesting is what do you do next? Like, because how many people go, oh, well, that's impossible or oh, but that seems like a lot of work or that's not for people like me, or,

[Dan Coyle]

you know, it's one of the barriers.

[Stephen Hanselman]

What do you do with it? That that's what ultimately matters.

[Dan Coyle]

Right, right. It's true. Where you get your reps, right?

[Stephen Hanselman]

Or quality reps. Do you do the reps or not?

[Dan Coyle]

Yeah, right.

[Stephen Hanselman]

I bet you see this a lot with athletes that you've seen come in through the organizations. Or you see someone who has all the raw mater, man, but it just doesn't happen.

[Dan Coyle]

And the reverse, someone who's like, yeah, they're too short, they're too slow, dah, dah, dah, dah. But they can absolutely do it. And it is this, you know, it's a combination of things, but it is an ecosystem is a good way to look at it because look, you're going to need to be plugged into some big source of energy.

[Ryan Holiday]

Yeah.

[Dan Coyle]

My favorite example of this is Jose Ramirez. He's five foot seven, he was signed for $50,000. He walks like. Do you ever watch Joy, the Jeffersons, George Jefferson? He's the most swagger walker, he's the most swaggy guy on the planet. Jose is. And when he got to the main, there was another player who was brought up with him and the other player was getting autographs of the other major leaguers in the clubhouse. And Jose, he said, jose, you want to get some autographs? And he goes, they should ask me for my autograph. I'm Jose Ramirez.

[Stephen Hanselman]

Is that confidence or is that ego?

[Dan Coyle]

I think it's earned at some level. It's deeply earned. But in a sport, it's a unique context. It's a sport where you fail a lot. And having that kind of crazy self belief can be helpful to a point. And then, man, that guy gets his reps. That guy pays. Every swing matters. He knows what he is up to with every rep and he gets more out of each rep. So from the distance, oh yeah, he's just super confident and that helped from, from depth. He's, he's absolutely based on something. It's based deeply on something.

[Stephen Hanselman]

So I told you I was at this Airbnb here in Maui on this

[Ryan Holiday]

trip we took and oh man, the

[Stephen Hanselman]

mattresses were not good.

[Ryan Holiday]

I did not sleep well. The kids did not sleep well. I wish that they had Helix mattresses. If you've ever slept on A Helix. You will know why so many people love them. Basically, you take this Helix sleep quiz that matches you with the perfect mattress based on your personal preferences and sleep needs. We've got the midnight mattress at our house. It's you know, medium firmness, not too firm, not too soft. And that's probably why it is their top selling model. Helix is the most awarded mattress brand tested and reviewed by experts like Forbe. They've got free shipping, seamless delivery and the whole process is super simple. They deliver the mattress right to your door with free shipping in the US and you can rest easy with the happy with Helix guarantee that ensures seamless returns and exchanges risk free customer first experience. The Helix guarantee is designed to ensure that you're completely satisfied with your new mattress and includes a 120 night sleep trial and limited lifetime warranty. Just go to helixsleep.com stoic for 27% off that's helixsleep.com stoic For 27% off. Make sure you enter our show name at checkout so they can know we sent you helixsleep.com stoic who likes bugs? Not me, I guess my wife does. My kids sometimes like bugs, but I don't like bugs in my house, right.

[Stephen Hanselman]

I don't like them around my food,

[Ryan Holiday]

I don't like them crawling on me.

[Stephen Hanselman]

I don't like.

[Ryan Holiday]

And the problem is you see one bug and then you ignore it and all of a sudden you got hundreds of bugs and you got an infestation. If you are looking for DIY pest control, check out today's sponsor. That's Pesti. They're making protecting your home from unwanted pests super simple with Pesti you can get started at 35 bucks a treatment and get a customized plan based on your location, bugs and climate. They send you everything you need. Pro grade pesticide. That's the same stuff the pros use. They give you a sprayer, they give you a mixing bag, gloves and instructions and you can complete the whole thing in less than 10 minutes.

[Stephen Hanselman]

My wife loves bugs, but she also

[Ryan Holiday]

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[Stephen Hanselman]

worried that killing the bugs will kill the animals.

[Ryan Holiday]

Well, pesty pesticides are fully registered and have been used in hospitals and schools all over the country. And you can try Pesti totally risk free with their 100% bug free guarantee or your money back. If the bugs don't go away, you get a free refund. Bugs, hate to see you coming with Pesti. Just go to pesti.comdoic for an extra 10% off. Your order, that's P-E-S-T-I-E.com doeic for an extra 10% off. So it's actually funny. Right after Dan left, we had a great little chat, and then we walked around the bookstore. He sent a note, and he said he felt like there was something he wanted to add about a story he was telling about the Cleveland Guardian star Jose Ramirez that he thought would explain him as the leader he is today. So let me put that in here,

[Dan Coyle]

how fearless he was, how he walked in and felt like instantly he was not intimidated by the major league environment. And the question is, when you dig into that, it's like, where does that fearlessness come from? Where does that confidence come from? And when you look into that, you go back to when he was 13 years old in Bani in the Dominican Republic, and Jose was playing for an adult league. And it was some tough guys and there was some gambling. And he has said that behind home plates, they kept a machete, kind of for, I guess, inspiration, you might say. So that's the kind of background that he came out. And when you come out playing game after game with that kind of pressure, the big leagues maybe isn't as intimidating to him as it would be to some other folks.

[Ryan Holiday]

Okay, back to Dan and I chatting in the studio.

[Stephen Hanselman]

I bet you see people who everyone is trying to get to put in the work, trying to give them the things they need to realize that potential, and it's just not getting through. And I suspect that at some level, that's the story of communists. There's also this fascinating statue of of Seneca in Nero. And, you know, Seneca is like trying to teach Nero, and Nero just kind of just your classic no way, sullen, petulant teenager that could not give two shits less. You know, that unreachability is probably what keeps coaches up at night. Like, I know if I could reach this kid, they could do it.

[Dan Coyle]

Absolutely. They're so defended, and they're so defended by what got them there. They've always been the best player. They're very well defended. And what ends up working in some cases is. Well, it works in every case, really, is a moment of vulnerability. Sometimes with an injury, sometimes with getting sent down, you'll have a window where they're kind of reachable, where it opens. And vulnerability. I think we often. We sometimes think of vulnerability the wrong way. Like, moments of shared vulnerability are what create relationships. You don't have to build up trust before you can be vulnerable. It's the vulnerability that makes it happen. And so having conversations during that time and creating a space where they can reflect and maybe find some new mental models and some new meaning and a new type of strength. Like there's the brittle strength. I'll show you. I'm the best player. I've always been the best player. That's brittle in the end. But then you've got something softer, something stronger, something that's more oriented often around service, around being a good teammate.

[Ryan Holiday]

Yes.

[Dan Coyle]

Around realizing that, hey, if you go 0 for 4 and the team wins, that's a good day. Right. So finding that, that level of. It's sort of a growing up process for them many times. And, and these days, if you're 19, you're a great athlete. You haven't had that many reps at growing up.

[Stephen Hanselman]

Yes.

[Dan Coyle]

So approaching them with a ton of patience and understanding because the easiest thing to do is to say kids a tool.

[Ryan Holiday]

Right, Right.

[Dan Coyle]

It's really, really tempting and easy. And that's true to a point. But if you continue to create that space and continue to give them opportunities to get those reps at growing up, you end up with a better outcome. Actual, actual growth. Which is painful but worth it.

[Stephen Hanselman]

Yeah. The coach that's able to sort of wait for the opportunity or the way in. Like they know this person needs to hear this thing, but they also know they're not ready to hear that thing. Yep. And they're willing to give them the latitude and the time till they're ready to come around.

[Dan Coyle]

Grace is not a bad word for that. Sure. In a way like it is because that's what it kind of takes. It's a gift. It's like give them that space especially. Yeah.

[Stephen Hanselman]

You're thinking about, it's that 20 years of day to day instruction.

[Dan Coyle]

Right.

[Stephen Hanselman]

Like you think about that's why you need that time. And you could argue that I think a lot of organizations and industries fail. I mean even our industry, like in publishing, like how many authors do more than one book with the same publisher is extremely rare. Publishers wonder why, you know, they have to miss so many times. It's because you don't cultivate or develop talent. You've decided to be a one off transactional relationship industry. And then you don't cultivate talent. How many coaches stay with the same team? How many players you know get shipped like because. Because everyone is looking. You have to have that short term success. It prevents you from developing long term leaders and long term talent.

[Dan Coyle]

It's so true. And the deeper irony of is we're so Terrible at predicting who's going to

[Stephen Hanselman]

be good, that you'd think we'd have some humility about it.

[Dan Coyle]

You'd think we would. You think we would. I'll give that person another chance. Like, like, really people?

[Ryan Holiday]

There is, I mean, Sam Darnold.

[Stephen Hanselman]

Yeah.

[Dan Coyle]

Oh, my God.

[Stephen Hanselman]

You're right.

[Dan Coyle]

Right? That's perfect.

[Ryan Holiday]

Yes.

[Dan Coyle]

That's perfect. Right? Yeah.

[Ryan Holiday]

Here it is.

[Stephen Hanselman]

I mean, and weirdly, that story is more common than Drake May, who's leading a team to a Super bowl, like in his first season or second season or whatever. Like, it's much more common that people struggle and fail and eventually come around and then surprise us somehow. That's surprising, even though it's the most common story. But instead we go, number one draft pick should be good out of the gate, and then they're not. And we get rid of them.

[Dan Coyle]

Get rid of them. Right. And then you go, you know, even one layer deeper there, and you always find that community of people. There's so many. You know, there's a lot of science on this too, but it's just like it's, you know, Darnold is not an individual, actually. Right. There is this whole dance that's going on with information and with movement on the field, and he's a part of that. And as a whole, they're quite effective. And you could pull him out of that and he would stop being effective. But we can't stop focusing on the individual and celebrating the individual. And every time, especially with this latest project, it's just like, man, the power of community. It's like you always see the solitary genius and the lone hero. And then you go, well, kinda, let's go a little deeper there. What about that moment when, you know, Jerry had the mentor? And so in my life, anyway, learning to, even though I'm singling out those individuals, learning to, like, actually squint my eyes a little bit and look for the latticework of relationships and those moments that helped form them through time and those reps where nothing happened. And then finally things came together. It's like, it's always way more complex than you think.

[Stephen Hanselman]

Yeah, it's like a successful president has a cabinet, which is the official relationships. Then they have what we call the kitchen cabinet, which is the unofficial advisors or teachers. And then maybe they have a spouse. And, you know, like, there's this huge network of people that are involved. And if they don't have it, if they are the solitary figures, those are usually not just the most miserable of the leaders, but ultimately they make some Catastrophic, unforced error. You know, I'm sure there are a lot of people that could have told Putin exactly how invading Ukraine would go.

[Dan Coyle]

Right, Right. Not a secret.

[Stephen Hanselman]

Except for there are no people who could tell them that because that is a kamikaze mission.

[Dan Coyle]

That's right.

[Stephen Hanselman]

And that is the sort of trap that. That dictators and sort of imperial CEOs and whatever. You know, whatever. The less sort of violent, authoritarian version of it is, is the more isolated you are, the worse you are because you're just getting less information and insights.

[Dan Coyle]

The group brain's really pretty good, right?

[Stephen Hanselman]

Yeah. We call it groupthink, but, like, sometimes, yeah, that can hold you back, but most of the time, it also holds you back from plunging off a cliff.

[Dan Coyle]

Yes. With genuine curiosity. And I keep seeing. You know, I talked to a guy named Dave Cooper one time who headed up the People who Got Bin Laden, Navy SEAL Team 6 commander, and he said the foremost important words that a leader can say are, I screwed that up.

[Ryan Holiday]

Right.

[Dan Coyle]

And they go two directions. You are fallible. You have wrong instincts. You screw things up. But to everybody around you, it creates that space where they can step in

[Stephen Hanselman]

and say, yeah, next time they can help you. They can help you before you screw it up, because they know you're interested in. You're okay with being wrong.

[Dan Coyle]

You gotta talk to me.

[Stephen Hanselman]

Yeah.

[Dan Coyle]

He would stand next to a window and kind of do it on purpose. And then there'd be someone new in the room. He would say, hey, you gotta tell me to move away from the window. I didn't realize I was standing by the window. That's a dangerous place for me to stand. Grab me if you have to. Grab me. Grab me. Creating that space where you're saying, you know, hey, you have a voice. This is not just safe for you to speak up, but it's. You have a role here. It's really important that you speak up.

[Stephen Hanselman]

Yeah, there's a story about Hadrian, who was actually not that great of a leader. He was a problematic, not ironically, not the model that Marcus Aurelius wants to model himself after. It's. It's ultimately Antoninus, but there's a story about Hadrian arguing with one of his advisors over some philosophical question or mathematical question, some. Some thing that they're arguing over. And. And they go back and forth, and eventually the advisor says, you know, actually, you know what? You're right. I'm wrong. You're right. And a friend comes up. He says, why did you.

[Ryan Holiday]

Why did you do that?

[Stephen Hanselman]

You. You're like, objectively, right here, there's no, let me show you, you know, why you're actually correct. And the advisor goes, I think you're mistaken. He says, the man who commands 40 legions is always correct. And that is the problem with being the leader or the person in charge, especially if you are intimidating or vindictive or, you know, withholding or any of those things that can serve as a sort of. Not just a deterrent, but then also a punishment to people who correct you or you end up not getting the thing you desperately want.

[Dan Coyle]

And so to do that Jiu Jitsu that is required to do that, of constantly humbling yourself, of constantly asking the least powerful person what they think, of constantly invoking stories where you screwed up ends up being the stoic practice, maybe of like, this sucks, but God, it creates conditions for this group brain to light up a little bit and knocks us out of our reflexive, hierarchical, kind of wince that we all do around power. And so these. The leaders that I've been around have got those jiu Jitsu moves down. They always are saying, I'm probably off on this. I don't have. What do you think, Bob? And they're constantly deflecting. They're constantly walking around and saying, hey, if you could change one thing about what we do here, what would it be? One thing. Change one thing. They're like a little fire hose of little signals that are like, I'm an idiot. It's kind of what all of them say, help me.

[Stephen Hanselman]

What they're not doing is what leaders think works. They go like, my door is always open. Nope. And. And then they think that's what's going to create a culture of feedback and criticism and, you know, sharing.

[Dan Coyle]

No, right, exactly. It doesn't come close. You have to actually build spaces, platforms, support people to get in that room and say those things, because we don't typically want to.

[Stephen Hanselman]

There's a story I think I told in Wisdom Takes Work about Elon Musk or someone. He just shared something horrendously offensive and stupid on. On Twitter. And one of his employees was like, hey, like, said I it. I'm genuinely worried that you shared this. You know, like, 1% of the population would fall for this thing. And you fell for, you know, he's like, sort of laying into him, right?

[Ryan Holiday]

And.

[Stephen Hanselman]

And Elon Musk, they're fucking fired. You know, he fires him, kicks him out of the room. And then later in that same meeting, he. He says, like, why isn't anyone else talking? You know, it's like, because you just executed someone in front of them. Yeah. Like, they're not only not going to share in this meeting, they're not going to share some safety concern or some legal concern nine months from now or nine years from now. That could prove catastrophic because you just gave them a very powerful demonstration of what you do when people criticize you to your face.

[Dan Coyle]

It's unbelievable. The lack of awareness of some of that stuff is almost hard to believe. Our capacity for self deception is.

[Stephen Hanselman]

And the timelessness of it. Right. This is what. This is mythic Kings were doing 10,000 years ago. And it's also what. But you know, parents do we go, like, I want you to come to me with anything.

[Dan Coyle]

Right.

[Ryan Holiday]

And then.

[Stephen Hanselman]

And then the last time they came to you, you grounded them. And then you wondered why they. They're not opening up to you.

[Dan Coyle]

And underneath it all, like, I'm so fascinated by that moment, those moments, because another sort of big unlock for me this idea that we've got two attention systems. Like we have kind of a task attention system that likes to do that kind of stuff, that likes control, that is built to get. Well, no one rid me of this priest, you know, that says bold things and that sees the world through a very, very narrow tube. And that is built. The evolutionary part is fascinating me that is built to grab food, is built to spot something valuable.

[Stephen Hanselman]

Control it quickly, win the interaction you're currently in.

[Dan Coyle]

Task attention, win it. Right. And then there's this other form of attention relational attention where it's like, oh, evolutionarily, I need to pay attention to the sky, to the social fabric. I need to be nuanced. I need to really connect to what's going on. The unlock was that they compete. You can't have both on at the same time.

[Ryan Holiday]

Sure.

[Dan Coyle]

And in all these moments, they're all like examples of people who are feeling super strong because that's how you feel when you're controlling. It feels great to say that Musk felt awesome when he said that.

[Ryan Holiday]

Yeah, yeah.

[Stephen Hanselman]

He was reveling in his power.

[Dan Coyle]

So much control. And the move over and over again is to like surrender that and say, well, wait a minute, wait a minute. I really can't control it. I'm really not the center of everything. I can't control everything. I'm just a person in this space. What's going.

[Stephen Hanselman]

What.

[Dan Coyle]

What is this? What's actually going. Going on here? And the leaders who have the ability to make that move, where they got to be a leader because they, like control a lot of times. But to have that move where they can actually sort of let go, or parents who can have that move and actually sort of let go. It's like endlessly powerful, the flipping between

[Stephen Hanselman]

short term, long term, do I want to be right about the couch or do I want to stay married? You know, do I want to decide my kids major or do I want them to bring their grandkids around 20 years from, you know, like, how do you think about the. Are you in the trap of the present moment or can. It's funny because we think like, we go, they're philosophical, it's not like they know Aristotle, right? It's like the lowercase philosophical. I think to me it's like, can you see the big picture? Can you go to what really matters, right? And so often you're in these exchanges where the thing you're trying to win doesn't fucking matter at all, right?

[Dan Coyle]

And our society is sort of increasingly built around those types of exchanges.

[Ryan Holiday]

And as we wrap up here, one thing that stands out to me from this conversation is how simple some of these ideas are, but how easy they are to overlook and of course, how difficult they are to put into practice. Culture isn't built through big speeches or strategies. Leadership isn't this performative thing. It's built through small signals repeated over and over again. And I think that's what Dan's work reminds us of. If leadership is more like tending a garden than running a machine, and the job isn't control, it's about creating the conditions, making the example so that people feel safe enough to contribute, to grow, and ultimately to flourish. Thanks again to Dan for coming out to the painted Porsche to have this conversation in person. If you're looking to become a better leader in your personal or professional life, I think you should check out the Culture co, the Talent code, the little book of talent. Of course, his new book, Flourish. I'll link to those in today's show notes. You can go to his website, danielcoyle.com and then we also have a big course we did here at Daily Stoke all about leadership that I think you'll like. The Daily Stoke Leadership Challenge. It's our longest course, it's our most involved course. We have a bunch of in depth interviews like this one in there and you can find all [e-mail] leadership or if you join us in DailyStoke [e-mail] you get that course and all of our courses for free as part of it. 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 would really help the show. We appreciate it and I'll see you next episode.

[Dan Coyle]

Foreign.

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