The Daily Stoic Podcast

Episode Title: BONUS: The Man Behind The Daily Stoic (Not Ryan Holiday)
Airdate: October 26, 2025
Host: Ryan Holiday
Guest: Steve Hanselman (Book agent, co-writer, collaborator)

Episode Overview

This special bonus episode features a rare, in-depth conversation between Ryan Holiday and Steve Hanselman—Holiday’s longtime literary agent, collaborator, and the pivotal figure behind the creation of the Daily Stoic project. The episode delves into their multi-year journey creating the Daily Stoic books, with a particular focus on the upcoming release, Wisdom Takes Work (the fourth and final installment in Holiday’s virtues series). The discussion covers the origin story of the "Daily Stoic," the philosophical challenges of writing about the four cardinal virtues, the interwoven nature of those virtues, and reflections on figures like Marcus Aurelius, Lincoln, and Elon Musk.

Key Discussion Points and Insights

1. Origin Story — The Man Behind the Curtain

[04:10-08:31]

• Ryan recounts that despite his own pivotal role, the Daily Stoic wouldn’t exist without Steve Hanselman:

  “There’s basically one person to thank for this all existing. Not me. ... It all traces back to a conversation I had with Steve Hanselman, my agent.”
  (Ryan Holiday, 04:16)

• Steve proposed the "page-a-day" format, inspired by "The Daily Drucker" from Peter Drucker’s writings. Ryan was initially skeptical but realized its potential as an accessible entry point:

  “These are a way to live with the thinking of someone, not just for a year, but over and over and over again.”
  (Ryan Holiday, paraphrasing Hanselman, 05:22)

• Notably, Steve volunteered to produce original Stoic translations based on his background in Greek and Latin.

  “I’ll do the translations... I went to Harvard Divinity School. I know both Latin and Greek.”
  (Steve Hanselman, paraphrased by Ryan Holiday, 06:11)

2. Launching a Multi-Book Virtue Series

[08:31-14:47]

• The book series was conceived on a family hike and grew organically into a major project over six years.

  “I remember you were out on a family hike first, called me with the idea for the series and we both got so excited about it.”
  (Steve Hanselman, 08:32)

• The four cardinal virtues (Courage, Temperance/Discipline, Justice, Wisdom) became the structure, echoing ancient Stoic debates.

• Steve and Ryan discuss how Christianity was influenced by Stoic virtues, with Paul himself borrowing heavily from philosophy:

  “Paul was a student of the philosophers…even quoting the Stoics, you know, to the audience.”
  (Steve Hanselman, 10:02)

• Key insight: These virtues are not just religious, but have a philosophical—and practical—origin.

3. Writing About the Virtues: Challenges and Interconnectedness

[15:18-20:06, 24:31-27:53]

• The challenge of separating the virtues:

  “Where does one begin and the other end? That’s really the tricky part of the whole thing.”
  (Ryan Holiday, 15:32)

• Courage almost always overlaps with justice and wisdom, both at a moral and practical level.

• Steve highlights how the Stoics shifted toward a "social courage" (megalosukiya or ‘greatness of soul’), particularly in Roman times.

• Ryan emphasizes that wisdom is not just theoretical, but practical (phronesis):

  "They used the word phronesis, which was practical wisdom. ... It was something we had to engage in, everything that we do."
  (Steve Hanselman, 24:33)

4. Wisdom: As Process, Not Possession

[27:21-32:19]

• Wisdom is inherently about application and openness to correction:

  “Wisdom is the ability to go through life ready to change your mind. Doesn’t mean we abandon our values because they’re inconvenient. But our thinking is supposed to evolve, we’re supposed to grow.”
  (Ryan Holiday, 28:14, quoting his own book)

• Marcus Aurelius is held up as a paragon of being open to correction despite his absolute power:

  “He talks about being wrong and changing his mind ... His word can literally mean life or death.”
  (Ryan Holiday, 28:39)

• The paradox of creative success: as your authority grows, you receive less outside correction, which can be risky for writers and thinkers:

  “When the stakes are highest, you’re actually getting the least amount of feedback and editing and accountability, right?”
  (Ryan Holiday, 30:44)

5. Historical Exemplars: Lincoln, Cleanthes, Musk

[34:05-41:06]

• Ryan and Steve discuss how both Stoic and modern figures embody and transmit these virtues.

• Lincoln and Cleanthes are presented as models of learning and humility.

  “They never forgot what they learned. ... It was about getting it right for themselves.”
  (Steve Hanselman, 36:22)

• On wisdom as internalized, hard-won, and self-motivated—not for external validation.

• The inclusion of Elon Musk as a controversial but instructive case:

  “Do you think people are going to get mad about the Musk section?”
  (Ryan Holiday, 39:54)
  “Musk has made quite a few people mad all on his own.”
  (Steve Hanselman, 39:58)

• Ryan explains his method: show both strengths and weaknesses, as Plutarch did. Musk epitomizes the danger of brilliance devolving into hubris.

6. Debating and Defining the Virtues

[41:33-48:03]

• Deep dive into how endurance fits: is it under courage or discipline? Steve argues Epictetus’s “persist and resist” spans both, and sub-virtues reveal the virtues’ interdependency.
• The most transcendent forms of courage are always founded on love or selflessness, echoing biblical “no greater love than to lay down one’s life for another.”

7. How Stoicism Instructs Us Today

[54:47-63:08]

• Studying great lives is not about hero worship but seeing ourselves reflected and learning from their strengths and failings:

  "You're supposed to study these lives ultimately, to see yourself reflected in them. That's the whole point."
  (Ryan Holiday, 54:47)

• The Stoic model: “constant debate”—if you’re Alexander at this battle, what would you do? Stoicism embraces practical application over abstract theorizing.

• Wisdom is a lifelong process, not a destination:

  “If you think you have it, you are exhibiting a sure sign that you do not have it.”
  (Ryan Holiday, 62:08)
  “It’s not an endpoint. ... And the point is that you don’t ever finish it.”
  (Ryan Holiday, 63:08)

8. Final Reflections: The Virtues, Achievement, and Flourishing

[63:49-64:31]

• Zeno’s insight: “Wellbeing’s realized step by step.” Pursuing the virtues doesn’t feel like giant leaps, but accumulates in significant ways.
• Steve marks the completion of the multi-year project:

  “Congratulations.”
  (Steve Hanselman, 64:31)

Memorable Quotes

• “People think of wisdom as something lofty...but the Stoics were very insistent that it was practical wisdom—phronesis.” (Steve Hanselman, 24:33)
• “Wisdom is the ability to go through life ready to change your mind. Doesn’t mean we abandon our values because they’re inconvenient. But our thinking is supposed to evolve...” (Ryan Holiday, 28:14)
• “When someone who has a plausible claim of being one of the smartest people in the world starts to see themselves as one, that’s the timeless danger of hubris.” (Ryan Holiday, 53:13)
• “If you think you have [wisdom], you are exhibiting a sure sign that you do not have it. It’s not an endpoint.” (Ryan Holiday, 62:08)
• “Wellbeing’s realized step by step, but it’s no small thing.” (Ryan Holiday, recalling Zeno, 64:12)

Notable Timestamps

• 04:10–08:31: The origin story—how Steve Hanselman sparked Daily Stoic.
• 08:31–14:47: The idea behind the virtues series and connections to history.
• 15:18–20:06: How the virtues overlap and why that matters.
• 24:31–27:53: Wisdom as practical, ongoing, not theoretical.
• 28:14–30:44: Openness to correction and the creative paradox.
• 34:05–41:06: On Lincoln, Cleanthes, and Musk as virtue exemplars.
• 41:33–48:03: Debating the placement and meaning of sub-virtues.
• 54:47–56:49: Using historical lives as mirrors for self-examination.
• 62:08–63:49: Wisdom as an endless pursuit.

Conclusion and Takeaway

This episode offers an unusually candid and philosophical look behind the scenes at how the Daily Stoic books came to be, and how their creation became a dialogue across centuries—between agents, modern writers, and ancient teachers. Core themes include the interdependence of the virtues, wisdom as a dynamic process, and the ongoing challenge of self-improvement. Both Ryan and Steve model what it looks like to be “in the work”—constantly questioning, refining, and learning. As they close out the virtues project, listeners are reminded that stoicism isn’t about knowing everything, but about never ceasing to seek and apply wisdom in daily life.