The Daily Stoic Podcast
The Stoic Secrets Great Leaders Use | Daniel Coyle
Host: Ryan Holiday
Guest: Daniel Coyle, author of The Culture Code, The Talent Code, Flourish
Date: March 21, 2026
Episode Overview
This episode brings together Ryan Holiday and leadership expert Daniel Coyle for a deep dive into what actually makes great leaders and organizations flourish—drawing inspiration from both modern research on teams and the classical wisdom of Stoicism. Touching on sports, Roman emperors, and business, the conversation challenges the myth of the solitary, all-knowing leader and explores how thriving cultures and true leaders are shaped by relationships, meaning, vulnerability, and the cultivation of environments where people can do their best work.
Key Discussion Points & Insights
Rethinking Leadership: From Machines to Gardens
[04:04] Daniel Coyle:
- Mental Model Shift: Traditional image of the leader as a solitary captain controlling all outcomes is outdated.
- Machine vs. Living System: "An organization...has machine like functions, but ultimately, deep down, it's a living thing." (05:04)
- Garden Analogy: Successful leadership is more about cultivating an environment than strictly controlling outcomes—think "gardener" rather than "engineer."
[05:12]—[06:23]
- Sense of Meaning & Mattering:
- The leader’s #1 job is to foster environments where people feel safe, valued, and connected.
- Agency matters: “Design space for agency. ... Organizations aren’t machines. They function more like rivers.” (05:17)
- Good organizations set direction (the riverbanks and horizon), but allow space for initiative within those boundaries.
The Lifelong Apprenticeship of Leadership
[06:23]—[07:20]
- Leaders Need Coaches Too:
- Even elite leaders (like Guardians coach Stephen Vogt) seek ongoing mentorship.
- Continuous growth means intentionally creating space for reflection, feedback, and experimentation.
Quote:
"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..."
— Dan Coyle [06:41]
Complexity vs. Complicated Systems
[07:53]—[09:32]
- Complicated: Predictable outcomes—like assembling a watch.
- Complex: Unpredictable, ever-changing systems—like raising a teenager or building culture.
- Leadership Requires Experimentation:
- Probe, experiment, adapt—there is no one-size-fits-all solution in real organizations.
Quote:
"When it's complex, you actually have to learn through experience. Probe is the word. So do an experiment..." — Dan Coyle [09:00]
Roman Emperors as Case Studies in Leadership Development
[09:32]—[12:59]
- Ryan draws parallels from Roman history, particularly the selection and mentorship of Marcus Aurelius by Antoninus, contrasted with Marcus’s failure to instill similar qualities in his own son, Commodus.
- "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...it works in one case, and then it doesn't work in this other case." — Ryan Holiday [11:33]
- Lessons on Apprenticeship:
- Long-term mentorship (Marcus Aurelius and Antoninus) produces strong leaders.
- Inherited roles without cultivation lead to disastrous outcomes (Commodus).
The Role of Motivation, Mentorship, and Ecosystem
[12:59]—[13:51]
-
Talent (genetic or situational) is only the starting point. What matters is cultivation through tradition, mentorship, discipline, and feedback.
-
“Which ends up looking not like a machine, but like an ecosystem in that you have to have a source of energy for it.” — Dan Coyle [13:02]
-
Marcus Aurelius’s Gratitude: Ryan reads from Meditations, noting how Marcus explicitly thanks his teachers for character, focus, compassion, and resilience. (Memorable segment at [13:58]—[17:13])
Ignition Moments and Sustained Drive
[17:13]—[19:07]
- Ignition Moments: Those key points when someone is inspired by a mentor or an idea ("the moment Springsteen saw Elvis on TV").
- What Do You Do Next?: The crucial difference is not just feeling inspired but choosing to pursue it, do the work, and get the "quality reps."
- Talent alone is not enough—attitude and endurance carry the day.
The Confidence-Ego Spectrum: The Story of José Ramírez
[19:21]—[24:04]
- José Ramírez, the undersized baseball star, exemplifies earned confidence and relentless work ethic.
- “They should ask me for my autograph. Like, I’m José Ramirez.” — José Ramírez, as shared by Dan Coyle [19:47]
- True self-belief in high-performance environments comes not just from swagger but from a deep well of preparation and overcoming adversity.
- Early exposure to pressure and challenge shapes resilience (e.g., playing for adult teams with real stakes at 13 in the Dominican Republic).
Vulnerability, Growth, and the Challenges of Cultivation
[24:04]—[27:37]
- Unlocking Potential: Coaches often struggle to reach talented but unresponsive players.
- Vulnerability: Genuine change happens when individuals become vulnerable—often following setbacks or failures.
- “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.” — Dan Coyle [24:47]
- Organizational impatience (short-termism) undermines long-term development.
- Most successes are “late bloomers,” not instant prodigies—yet systems often discard people too soon.
The Power of Community Over the Lone Genius
[28:19]—[30:00]
- Success stories are rarely about solo actors—there’s always a latticework of relationships and mentors.
- Even “solitary” presidents, CEOs, or artists rely on official cabinets, informal advisors, and personal support.
- Isolation breeds error and hubris; community brings perspective and course correction.
The Importance of Humility, Feedback, and Psychological Safety
[30:00]—[34:35]
-
Group Brain: Teams that admit mistakes and invite dissent outperform those that suppress critical voices.
-
Navy SEAL Lesson: “The foremost important words that a leader can say are, ‘I screwed that up.’” — from SEAL Team 6 Commander Dave Cooper, as quoted by Dan Coyle [30:27]
-
Story: Elon Musk once punished an employee for honest feedback, sending a lasting negative message and stifling future dissent ([33:41]).
-
Leaders must go well beyond “my door is always open.” They must actively engineer spaces that encourage honest feedback and contribution.
Two Modes of Attention: Control vs. Relationship
[34:59]—[37:13]
- Humans, and especially leaders, naturally default to “task attention” (control, quick wins, focus on the immediate).
- True leadership requires intentionally toggling to “relational attention”—seeing the big picture, understanding the fabric of relationships, and focusing on long-term culture, not just immediate outcomes.
- “Do I want to be right about the couch, or do I want to stay married?” — Ryan Holiday [36:36]
Final Reflections & Actionable Takeaways
[37:19]—[39:10]
- Leadership is not performative, nor is culture built on big speeches.
- Small, repeated signals of trust, humility, and care are what actually shape environments where people and organizations flourish.
- The best leaders create the conditions for growth by letting go of control, modeling vulnerability, and making everyone feel their contributions matter.
Notable Quotes & Memorable Moments
- "An organization, ultimately it has machine like functions, but ultimately like down super deep, it's a living thing." — Dan Coyle [05:04]
- “Leadership isn’t about pulling levers and controlling outcomes. ... It's actually about relationships. It's about meaning. It's about building environments where people feel safe, feel connected, like their contribution matters.” — Ryan Holiday [03:13]
- "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." — Dan Coyle [06:41]
- "It ain't complicated. Things come together the same way every time... Complex things change as you interact with them." — Dan Coyle [08:01]
- “We always see the solitary genius and the lone hero, and then you go, well, kinda. Let’s go a little deeper there. ... Look for the lattice work of relationships and those moments that helped form them through time.” — Dan Coyle [28:19]
- “The foremost important words that a leader can say are, ‘I screwed that up.’ ... it creates that space where they can step in and say, yeah, next time they can help you before you screw it up, because they know you’re...okay with being wrong.” — Dan Coyle [30:27]
- “Task attention likes control. ... Relational attention—where it’s like, oh, I need to pay attention to the sky, to the social fabric. ... They compete. You can’t have both on at the same time.” — Dan Coyle [35:35]
- “Leadership is more like tending a garden than running a machine. The job isn't control.” — Ryan Holiday [37:19]
Useful Timestamps
- [04:04] — Redefining leadership: captain vs. gardener
- [06:41] — Leaders seeking mentorship; continuous learning
- [07:53] — Complicated vs. complex systems
- [09:32] — Lessons from Roman emperors and mentorship
- [13:58] — Marcus Aurelius’ gratitude to mentors (Meditations passage)
- [19:21] — Story of José Ramírez and earned confidence
- [24:47] — Vulnerability as the path to real relationship and growth
- [30:27] — The importance of leaders openly admitting mistakes (SEAL story)
- [33:41] — Elon Musk and the danger of punishing honesty
- [35:33] — Two systems of attention: control vs. relationship
Tone and Language
The conversational tone is warm, anecdotal, and reflective—rich in classical references, contemporary sports and business analogies, and grounded, practical wisdom.
Final Thoughts
Ryan and Dan’s dialogue provides a rich, actionable resource for anyone looking to lead—whether in business, sports, or personal life—with humility, courage, and a deep appreciation for the complexity of human systems. Their core message: the secret to great leadership is not control, but cultivating culture, fostering relationships, building trust, and letting the whole group flourish together.