Kibbe on Liberty Ep 348: What Stoics Can Teach Libertarians

Host: Matt Kibbe
Guest: Ryan Holiday (Author, Producer of The Daily Stoic)
Date: September 3, 2025
Duration: Approx. 26 minutes

Episode Overview

In this episode, Matt Kibbe sits down with Ryan Holiday, celebrated author and the force behind The Daily Stoic, for a deep dive into the surprising kinship between Stoicism and libertarian philosophy. Recorded live at Freedom Fest, their conversation explores the practical virtues at the heart of both schools of thought, the role of the individual in a turbulent world, and the urgent need for values and character in the face of social and political upheaval. Kibbe and Holiday also tackle cultural topics ranging from Adam Smith to Rush drummer Neil Peart, and reflect on the future of democratic institutions in the age of social media.

Key Discussion Points and Insights

1. Foundations: Stoicism Meets Libertarianism

[00:55–02:54]

• Kibbe's Influence: Matt admits his exposure to Stoicism comes primarily from the enthusiasm of his team and from watching Ryan's speech earlier that day.
• Common Philosophical Roots:
  • They discuss the overlap between Adam Smith’s Theory of Moral Sentiments and Stoic values, noting the direct intellectual lineage:
    • Ryan Holiday: “Which is a primarily Stoic based text.” [01:34]
    • Matt Kibbe: “It's like if you're going to read the Wealth of Nations, you should probably read the Theory of Moral Sentiments first to understand the moral structure that holds civil society together.” [01:58]
• Stoic Cardinal Virtues:
  • Courage, discipline, justice, wisdom—these virtues echo through philosophical and religious traditions.
  • Ryan Holiday: “Everything that happens to us is an opportunity… to practice virtue.” [02:54]
• Virtue as Action:
  • Stoicism’s actionable philosophy aligns with libertarianism’s emphasis on personal responsibility and agency.

2. Personal Responsibility & Community

[04:01–04:56]

• Comfort with Unchangeable Circumstances:

  • Kibbe relates Stoic acceptance to navigating politics in Washington, D.C., focusing on “what can I do to make a difference… even if I’m all alone.” [04:24]
  • Ryan Holiday: “The role of the philosopher is… to try to make a small contribution to a very large project.” [04:40]

• Practice Over Theory:

  • Both agree that living these philosophies matters more than debating them:
    • Matt Kibbe: “It’s not enough to be sort of an armchair philosopher... liberty is that responsibility to do something.” [05:13]

3. Mastery, Humility, and Learning

[05:50–07:23]

• Neil Peart’s Lessons:
  • The Rush drummer exemplifies lifelong learning and self-improvement, resonating with Stoic humility.
  • Ryan Holiday: “What is a master but a master student?... Here he is going to class like everyone else. I just love that image.” [05:57]
  • On philosophy: “If the philosophy is making you more of an asshole, you’re probably taking the wrong thing out of it.” [06:54]
• Philosophy in Action:
  • Looking at how philosophers lived is as important as their words.

4. Enduring Adversity—Stoic & Libertarian Resilience

[08:06–09:24]

• Neil Peart’s Perseverance:
  • Surviving personal loss, Peart’s journey mirrors Stoic resilience.
  • Ryan Holiday: “Stoics weren’t like people whose lives went well for… it was how do you not let life break you?” [08:17]

5. Misconceptions: Is Stoicism Pessimistic?

[09:25–10:59]

• Addressing Straw Men:
  • The notion that Stoicism is defeatist is rejected:
    • Ryan Holiday: “… it’s better to say that up front than be disappointed and frustrated...” [09:36]
    • Matt Kibbe: “I think life is an opportunity to do amazing things. But that struggle… is hard work, and you can’t… shortcut.” [09:52]
  • Ryan Holiday: Discusses how success and abundance, rather than struggle, often reveal character.

6. Social Contract, Justice, and Culture

[11:47–14:54]

• Adam Ferguson and Emergent Order:
  • Kibbe draws libertarian connections from Scottish Enlightenment thinkers, especially the idea “the product of human action, but not of human design” as a rebuttal to central planning. [11:47]
• Justice Beyond Law:
  • Ryan Holiday: “When people hear the word justice… they think laws and the legal system, but it’s really about what kind of person are you?” [12:55]
  • The importance of culture, character, and basic moral norms for the success of free societies.

7. The Seven Rules of Liberty & Stoicism

[14:54–18:27]

• Kibbe lays out his “seven rules of liberty” as a synthesis of philosophical influences:
  1. Don’t hurt people
  2. Don’t take their stuff
  3. Take responsibility
  4. Work for it
  5. Mind your own business
  6. Fight the power
• Stoic-Libertarian Overlap:
  • Ryan Holiday: Cites Marcus Aurelius' writings on equality, freedom of speech, and rulers respecting rights, even as historical realization lagged behind ideals. [15:42]
  • Warns of societal backsliding, especially amid legislative dysfunction.

8. Technology, Knowledge, and the Public Square

[18:27–23:23]

• White Pill vs. Black Pill on Social Media:
  • Kibbe contends technology “democratizes knowledge” and enables access to philosophical ideas, but warns it can equally empower extremists. [18:27], [19:22]
  • Ryan Holiday highlights parallels to the evolution of journalism, advocating for self-policing communities and social ostracism of abhorrent ideologies. [20:42]
  • Ryan Holiday: “Being a Nazi shouldn’t be literally illegal, but you should find yourself real isolated and lonely because we don’t fuck with Nazis.” [21:36]
• Need for Honest Dialogue:
  • Kibbe sees a possible shift back to honest, long-form conversations, “humble enough to let people figure out stuff for themselves.” [23:10]

9. Education, AI, and Civic Virtue

[23:23–24:31]

• Ryan Holiday: Expresses concern that separating truth from fiction will become harder with AI, emphasizing the increased value of the humanities for a flourishing democracy.

10. Can Character Save Our Institutions?

[24:31–26:06]

• Constitutional limits must be backed by norms and civic virtue:
  • Ryan Holiday: “You can’t design a system...without deferring to people...the founders just assumed that you wouldn’t meet someone utterly shameless and utterly without character...” [25:01]
  • Modern media allows the rise and toleration of figures who undermine these assumptions.

Notable Quotes and Memorable Moments

• On Stoic Practice:
  • “Everything that happens to us is an opportunity… to practice virtue.”
    — Ryan Holiday [02:54]
• On the Role of Philosophy:
  • “It’s not enough to be sort of an armchair philosopher... liberty is that responsibility to do something.”
    — Matt Kibbe [05:13]
• On What Stoicism Is For:
  • “It's like, how do you not let life break you?”
    — Ryan Holiday [08:17]
• On Character and Power:
  • “Here you have a guy [Marcus Aurelius] who is made better for having power and success, which is not normally the direction that it goes.”
    — Ryan Holiday [10:45]
• On Social Contracts:
  • “Without a culture that encourages socially focused choices, I think you get into a real dark place real quickly.”
    — Ryan Holiday [12:55]
• On Cancel Culture and Social Norms:
  • “Being a Nazi shouldn’t be literally illegal, but you should find yourself real isolated and lonely because we don’t fuck with Nazis.”
    — Ryan Holiday [21:36]
• On Technology and Knowledge:
  • “Information and knowledge is more democratic, which means you can follow idiots or you can follow smart guys, and it’s sort of up to you to figure out who those guys are.”
    — Matt Kibbe [19:59]
• On Institutional Decay:
  • “You can't design a system that is freeing and provides liberty without deferring to people... the founders just assumed that you wouldn’t meet someone utterly shameless and utterly without character and utterly without values.”
    — Ryan Holiday [25:01]

Timestamps for Core Segments

| Timestamp | Topic | |-------------|---------------------------------------------------------------------------------------| | 00:55–02:54 | Common roots: Stoicism & libertarian philosophy | | 04:01–04:56 | Responsibility, personal agency, and community | | 05:50–07:23 | The ethic of self-improvement: Neil Peart, mastery, and humility | | 08:06–09:24 | Resilience in adversity: Stoic lessons from rock and ancient Rome | | 09:25–10:59 | Debunking Stoic pessimism; success as moral challenge | | 11:47–14:54 | Adam Ferguson, emergent order, and the social contract | | 14:54–18:27 | “Seven rules of liberty” and their overlap with Stoic principles | | 18:27–23:23 | Social media, knowledge democratization, and the future of honest dialogue | | 23:23–24:31 | The humanities and AI: education as armor for democracy | | 24:31–26:06 | Institutional failure and the civic condition for freedom |

Further Resources

• Ryan Holiday:
  • Daily Stoic: dailystoic.com
  • Daily Dad: dailydad.com
  • Books by Ryan Holiday: Available at most bookstores

This engaging and wide-ranging conversation spotlights how timeless philosophical virtues—endurance, responsibility, humility—form the bedrock of both Stoic and libertarian worldviews. With practical examples and a candid look at our future civic challenges, Kibbe and Holiday make the case that “living philosophy” is just as essential—and urgent—today as in ancient Rome.