Ep 348 | What Stoics Can Teach Libertarians | Guest: Ryan Holiday

Summary

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

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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.

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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.

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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]

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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 |

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Further Resources

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

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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.

Transcript

[Kibbe on Liberty Host]

Welcome to Kibbe on Liberty. I'm live at Freedom Fest and I'm going to talk to Ryan Holiday, producer of the Daily Stoic. And we're going to look for common ground between Stoicism and libertarianism. And we solve all the problems, so you got to check it out. Welcome to Kibby on Liberty. Hey, Ryan, good to. Good to finally meet you.

[Ryan Holiday]

Yeah, thanks for having me.

[Interjecting Team Member]

Yeah.

[Kibbe on Liberty Host]

I will admit I don't know much about your work.

[Ryan Holiday]

Okay.

[Kibbe on Liberty Host]

And everything I know about you is from two guys on my team who are super fans of the Dale Stoic and the various work you do. But I was able to watch your speech today and your conversation with Daniel Richards about Stoicism versus Objectivism. I'm sort of. I had a philosophy major, a minor in college, but I'm just a collector of people that I think are interesting and have interesting ideas. And it's. For me, it's. I love Ayn Rand, I love Friedrich Hayek, Adam Smith, particularly the Theory of Moral Sentiments.

[Ryan Holiday]

Yes. Which is a primarily Stoic based text.

[Interjecting Team Member]

Yeah.

[Kibbe on Liberty Host]

It sounded like it was kind of coming from the same place.

[Ryan Holiday]

Yeah. His teacher, I'm forgetting his name, is a translator, one of the English translators of Epictetus.

[Interjecting Team Member]

Yeah.

[Ryan Holiday]

So he comes from that tradition and is not the sort of ruthless capitalist that he sometimes is made out to be.

[Interjecting Team Member]

Yeah.

[Kibbe on Liberty Host]

It's like if you're going to read the wealth of nations, you should probably read the Theory of Moral Sentiments first.

[Ryan Holiday]

Yes.

[Kibbe on Liberty Host]

To understand the moral structure that holds civil society together.

[Ryan Holiday]

Yes. That's a great. Yeah. Russ Roberts has a good book called How Adam Smith Can Change youe Life.

[Interjecting Team Member]

Yeah.

[Ryan Holiday]

It's sort of a deep dive into A Theory of Moral Sentiments, which is itself pretty readable. But like, I think Russ book is really good.

[Kibbe on Liberty Host]

But I also, like, there's an important moral philosopher named Jerry Garcia that's had a big influence on me as well. So I like to mash this stuff up. And I'm a libertarian. I can't think of a better word. It used to be liberal, but now we have to use the word libertarian to distinguish us from sort of radical progressivism. But I was hoping that you could give us those core values that you talked about on stage for people that don't know your work for. I don't even know much about Stoicism. And then I kind of want to compare it to the way I think about libertarianism.

[Ryan Holiday]

Okay. Yeah. The cardinal virtues of Stoicism are courage, discipline, justice and wisdom. Those are going to be familiar to anyone with a Basic understanding of Christianity too, which takes those from the Stoics. But it's this idea that we. Marx, Realisation, one of the ancient Stoics, talks about how everything that happens to us is an opportunity, that obstacles are an opportunity. What he meant was not that everything is a chance for us to make more money or succeed or whatever. What he meant is that everything is an opportunity to practice virtue. Sometimes it's the chance to practice courage, sometimes discipline, sometimes justice, sometimes wisdom. Most of the time some combination of all of the above. But if, if you go through life thinking that that's my job, to live and act with those virtues which I have tattooed on my wrist here, you sort of go, okay, it doesn't really matter what happens. I know what my job is. I have preferences of how I'd like things to go, but whether they go that way or not, I know how I'm supposed to behave.

[Kibbe on Liberty Host]

I've always ascribed to that. I would have never called it stoicism, but as a libertarian who lives and works in Washington D.C. you've had to become comfortable with some of the things you can't change. Yeah, you could look at all the injustices in the world and the things that governments are doing to people at the margin and all of the wars and everything else, and wrap yourself around an axle about trying to stop all the injustice, while at the same time focusing at the margin, what can I do to make a difference? And if I'm all alone in that fight, it's okay, but it'd be better if I could bring a community together.

[Ryan Holiday]

Sure, I think that's right. And by the way, the role of the philosopher is not to sit around and have thought experiments, but to try to change things at the margins. Maybe you get lucky and you'll have a big change, but largely your job is to try to make a small contribution to a very large project.

[Kibbe on Liberty Host]

One of my childhood heroes was the drummer from a band called called Rush, of course, Neil Pearts. And he's the one that introduced me to Ayn Rand when I was a kid. But he gave this great interview where he talks about the importance of doing the work. It's not enough to be sort of an armchair philosopher, and he's very animated by, at the time, the ideas of Ayn Rand, but to actually practice it in your work, and to me that's. I feel like Ayn Rand sometimes gets straw manned because the importance of being an individual and owning your own life is the responsibility that comes with that. You know, when you look in the mirror and you're focused on something. Maybe it's a work project, maybe it's a family problem, maybe it's a community problem. I think liberty is that responsibility to do something. And to me, that sounds a little stoic based on your framing.

[Ryan Holiday]

Yeah. Yeah, I do. I love Neil's work, actually. I talk about him in the wisdom book that I just finished. He's arguably the greatest drummer of all time. And at some point, he decides to start taking drum lessons again. And he says something like, what is a master but a master student? And this idea of committing oneself to the craft of the thing and humbling yourself before it is, to me, a very stoic idea. There's a story about Marcus Aurelius. He's seen leaving the palace one day in Rome, and a friend says, where are you going? And he says, I'm off to see Sextus the philosopher. To leave, learn that which I do not yet know. I just think even. I mean, the Emperor of Rome could have sent for any teacher he wanted to, but here he is going to class like every one else. I just. I love that image. And when I. When I think. I think Stoicism is easy to straw man. Objectivism is easy to straw man. At the same time, you know, if the philosophy is making you, you know, more of an asshole, you're probably taking the wrong thing out of it. And I think either one of them can do that for you.

[Kibbe on Liberty Host]

Yeah, of course.

[Ryan Holiday]

It's. When I think you look at the lives, I think it's important that we look at the lives of the philosophers. Not just what they said, but how did it look in practice. And that's what I like about the Stoics, is that they were involved, that they seem to be genuinely principled, that they. They also seem to have lived pretty good lives amidst tumultuous times, you know?

[Interjecting Team Member]

Yeah.

[Kibbe on Liberty Host]

I want to tell one more Neil Peart story, because I'm all ears. I think it's. And maybe you've seen the final concert film, which is sort of the last tour that rush did was 2015, and Neil didn't want to do it because his drumming is so muscular. He never wanted to perform anything less than what he would view as perfection or as close as he could get. And in the middle of the tour, his hands are bleeding and his feet are bleeding, and he's in visible physical pain playing the way that he plays. And he explains it. Why would you do that to yourself? And he's like, because I promised I would.

[Ryan Holiday]

I saw them on. I think it was the 30th anniversary tour. They played no opening band. They just played for three hours. Some of the hardest fucking songs you can imagine.

[Interjecting Team Member]

Yeah.

[Ryan Holiday]

And it was coming out of, you know, a horrendous series of personal reversals and losses for him. He wrote a book called Ghost Rider. That's a memoir. This motorcycle trip that he takes after he loses his wife and daughter. I carry it in my bookstore. I think it's one of the great. Not just great memoirs, but one of the great American road trip books. I just absolutely love it. And, you know, the stoics weren't like people who life went well for. Marx rewius buries half of his children. He lives through disaster and setbacks and reversals. And I think, as a philosophy, it was how. How do you not let life break you? And that book is really about him sort of nursing himself back to health and coming out of a thing that I don't think most people would have been able to come out of or would have come out of bitter and cynical and dark. And to me, that's what stoicism is. It's like, how do you. How do you not let life break you?

[Interjecting Team Member]

Yeah.

[Kibbe on Liberty Host]

And you and Daniel talked about this, and, you know, the straw man of stoicism, that it's determinist. And, you know, you're. You know, life is gonna be hard, and then you're dead.

[Ryan Holiday]

Yeah, but it's better to say that up front than be disappointed and frustrated that it's not the way you want it to be all the time.

[Interjecting Team Member]

Yeah. Yeah.

[Ryan Holiday]

That's my view.

[Kibbe on Liberty Host]

But to me, like, my biggest beef with Jordan Peterson is like, yes, get up and make your bed. But I don't think life is miserable.

[Ryan Holiday]

No.

[Kibbe on Liberty Host]

I think life is an opportunity to do amazing things. But that struggle to do something worth doing is hard work, and you can't. There's no shortcut.

[Ryan Holiday]

I think, you know, it's easy to talk about. How does the philosophy help you in times of deprivation and difficulty? I think Jordan Peterson's a great example of a guy who succeeds, succeeded beyond his wildest dreams, and seems to me to be a profoundly unhappy, miserable, and not very nice person. Like, it's the definition of what happens when you get abundance beyond your means. This is the power that reveals what you are inside. And, you know, that's what I admire about, say, Marcus Aurelius is. Here you have a guy who is made better for having power and success, which is not normally the direction that it goes.

[Interjecting Team Member]

Yeah.

[Ryan Holiday]

And how we wrestle with not just the problems of things not going our way. But how do we wrestle when famous or successful or rich? Does that make you better or worse? Again, that's the opportunity too. And the challenge.

[Kibbe on Liberty Host]

How do you, how do you, how do you, like, manage yourself?

[Ryan Holiday]

Yeah.

[Kibbe on Liberty Host]

Once you start to believe your own.

[Ryan Holiday]

Yeah. Or how do you stop yourself from believing your own bullshit so you don't become a shitty person?

[Interjecting Team Member]

Yeah.

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[Kibbe on Liberty Host]

I want to learn something because you mentioned something very early about the relationship between the Stoics and the Scottish Enlightenment philosophers. There's another guy named Adam for Ferguson who is very important to the Austrian economists and libertarians generally because he's the one that talked about the product of human action, but not of human design. And it was the ultimate critique of kind of central planning, the kind of progressivism that says, I'm smarter than you so I can redesign the world from the top down. And it was this process of just people trying to figure out how to achieve their goals and with the abilities that they have through cooperation with other people and institutions. Like, don't hurt people, don't take their stuff, keep your promises. These things emerge. This is a classic Friedrich Hayek argument that things emerge when people are free to figure stuff out. And there's rules of the game that generally people know that if you engage with other people, they're not going to steal from you or kill you.

[Ryan Holiday]

Yeah, yeah. It's interesting. So much of our political debate these days is like, about these, like this bill or that bill, this thing or that thing. And I think when people think, hear the word justice, for instance, one of the Stoic virtues, they think like laws and the legal system, but it's really about like, what kind of person are you? Right. Like libertarianism talks about how people shouldn't be coerced, they should make choices. But without a culture that encourages sort of socially focused choices, I think you get into a real dark place real quickly. Right. You end up in the sort of Hobbesian world. You need values and culture and character because people don't always make great decisions. Right. And so I think so much of what it feels like we're fucking around with right now is like, basic social contract stuff and people's inability to understand, you know, like, freedom of religion is there because the alternative is people murdering each other over their religious faiths. That was a hard won innovation that the founders came to. Right. And this idea that, oh, we're a Christian nation and we need to put. It's like, no. They were explicitly reacting against the excesses of the mixing of religion and government. They thought personally you had to have values, be they philosophical or religious, but they knew what happened when you empowered one over the other. And I just think we have some people who don't know what they're talking about, and they don't have a historical understanding, just sort of kicking out some very important legs of the stool that we all sit on.

[Kibbe on Liberty Host]

So I want to get your reaction. I tried to translate the entire canon of. Of Judeo, Christian, Libertarian, Scottish Enlightenment, and of course, Jerry Garcia and the Big Lebowski. It's all part of a whole corpus. And the original joke, which was not a joke, is I want to take all 700 pages of the Theory of Moral Sentiments and translate it into a tweet, which was, don't hurt people and don't take their stuff.

[Ryan Holiday]

Sure.

[Kibbe on Liberty Host]

So I came up with seven rules of liberty. Those were the first two. Don't hurt people, don't take their stuff, take responsibility, work for it, mind your own business, and fight the power. Which of those. And I said that too fast, maybe, but do you see a lot of common ground with stoicism in that framing?

[Ryan Holiday]

There's actually a passage at the beginning of Meditations where Marc Rios talks about a society based on equality of status, freedom of speech, and. And rulers who, above all, respect the rights of their subjects. I sort of think of that as a very Jeffersonian statement where he meant it but came nowhere close to realizing it in practice. And it has been the subsequent. The work of subsequent generations each time to get a little bit closer to it. So I think that's where the Stoics were in theory. But then in practice, you're reading that quote from a guy that owned slaves. Right. You're reading that quote from a guy who lives over an enormous hegemonic empire predicated on invading places and taking a chunk of their stuff as tribute. Right. And we have slowly, iteratively, I think, gotten ourselves a little bit closer each generation. My worry is where is. Maybe that work is Stalling out. And we're now openly flirting with a reversion from those ideas. And that sort of social media and such makes it easy to promulgate profoundly, I think antisocial, even evil ideas on both sides of the spectrum. But I think we are seeing a resurgence of sort of authoritarian impulses largely because the democratic system is not functioning as it's supposed to. When you have three co equal branches of government, not even really co equal, but we have three branches of government and one of them ceases to do its job, which is the legislative branch, which is supposed to be nimble and represent the people and be able to actively engage to address problems. You put incredible strain on the judiciary, you put incredible temptation on the presidency to be the man on horseback, the woman on horseback, and the system breaks down. We have a world where people think that being elected to Congress is like a media job and it's a legislative job. You're supposed to be passing laws or overturning, you know, eliminating laws or fine tuning laws that are supposed to allow society to function and address the problems of, you know, modern life. And we, we don't have that. We don't have a functioning legislative branch. And I don't know when you could say we last had a functioning legislative branch. And yeah, again, that creates the pressure that the Romans knew all too well. Catiline is basically sicking the mob on the Roman Senate because the Senate is not adequately responsive to the people's needs. And so when you don't have that, the, the system falls apart.

[Kibbe on Liberty Host]

So I wonder, like my theory, and this is my white pilled version of the theory, and I could give you the black pilled version too. But my theory is that technology and social media has democratized knowledge and red pilled a lot of us about myths that we believed were true, like the virtues of the legislature. And you know, you thought that there was sort of it was happening the way that you learned in grade school and it turns out to be far more cynical and self serving and power corrupting and all that stuff. But in the process of learning how the world actually works, we've leveled the playing field. You can follow idiots online, but you can also learn about stoicism in a way that wasn't possible. Like if you couldn't afford to go to university 20, 30, 40 years ago, you didn't have access to this stuff.

[Ryan Holiday]

So you can find and learn all sorts of things you would have never learned. You can also find a bunch of bigots or racists or crazy people and instead of there being one in every town. They're all, you know, together and they're able to act in concert. And that's, that's good. A really. Those are the kinds of factions that the founders were really worried about that used to be distributed or they found it hard to actually get much access to the levers of power. And now they have that. And that's a dangerous thing.

[Kibbe on Liberty Host]

Yeah, and that's the black pill, the white pill. Going back to Adam Ferguson and the whole idea of spontaneously emerging institutions. I think, I think we're going to have to figure out a new set of rules based on this wide open, competitive, you know, for all of the censorship and algorithms and all that stuff, it's more democratic. 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. But there'll be a new set of institutions that helps us figure out something closer to the truth as opposed to waiting for Walter Cronkite to tell you what the truth was.

[Ryan Holiday]

My first book was about media manipulation. And one of the things I talked about is that the thing that ultimately tames yellow journalism is number one, sort of a press moving to a more subscription model so you're paying for it instead of buying it from a newsboy on the side of the street. And then two, the creation of kind of newspaper guilds, guilds and press clubs and a sort of an, understand a sort of not legal, but a self policing mechanism inside a culture. Right. And that's what I'm talking about. A lot of these problems shouldn't be solved with laws, but they should be solved by people going, yeah, I don't fuck with that. Like, you know, being a Nazi shouldn't be literally illegal, but you should find yourself real isolated and lonely because we don't fuck with Nazis. You know what I mean?

[Interjecting Team Member]

Yeah, yeah.

[Ryan Holiday]

And I think we have struggled to sort of police and maybe this is a struggle, the pendulum swinging too far after cancel culture or whatever. But like society does need a means to cancel people who are antisocial again. That's a difference between being sent to an El Salvadorian gulag and just going, hey, I can't get work anymore because I suck. And people aren't going to deal with me until I repudiate these abhorrent ideas. And that's, I think, what we need. But when we live in an algorithmic world, we just like. It's like instead of going, hey, that seems wrong, we go I don't know. Got a lot of tweets, you know, a lot of people, a lot of engagement. And engagement as a proxy for whether something is good or bad, any artist can tell you, is a disaster.

[Kibbe on Liberty Host]

To that last point, I wonder if there's not a sorting out. So chasing clicks and doing rage bait and all the bullshit that then, you know, all that bullshit. You see, it strikes me that there is a, a movement towards things that are more honest and substantial.

[Ryan Holiday]

Yeah.

[Kibbe on Liberty Host]

At the same time. So like when, when the market clears. The market never clears, by the way. It's a process. But when, when the market shakes out with all of this, this noise.

[Ryan Holiday]

Yeah.

[Kibbe on Liberty Host]

Are people. And I'll put you in this category as I understand what you do. These are long form, honest conversations that are humble enough to let people figure out stuff for themselves. I think there's a trend towards that stuff.

[Ryan Holiday]

I hope so. I hope so. I just think if we're struggling to separate fact and fiction, truth and falsity, I think in a world of AI, it's going to be extra difficult. And if you don't have a base of knowledge, if you don't have a sense of history, if you don't have a philosophical background, if you don't have media literacy, like one of the fascinating and horrifying things about AI is its ability to just like hallucinate shit. Right. And so if people are struggling with that now, how are they going to manage just a bombardment of it? I think so anyways. The irony is that a humanities, a broad based humanities education, didactic or from a university is going to be more essential than ever and is in fact an essential part of a functioning democratic society, a society of flourishing individuals. If you, you don't know what's what, you're going to have a hard time.

[Kibbe on Liberty Host]

A final thought on this idea because you mentioned the dysfunctionality of the legislature and the executive branch. I'm learning the hard way as a libertarian that very much believed in the power of constitutional limits on government. It turns out that those limits aren't so useful if the president ignores them, if the legislature ignores them. And so many. The restraints on their behavior were not legal.

[Ryan Holiday]

Legal, they were normative. No, this is exactly what John Adams is saying, is that you can't design a system that is freeing and provides liberty without deferring to people. Right. And I think we're learning that the founders just assumed that you wouldn't meet someone utterly shameless and utterly without character and utterly without values. And what they designed has just not been a match for that. Look, I think there's some particularly egregious examples. And then this is also a problem as a whole with all parts of the the system, whether we're talking about stock trading or refusing to retire or whatever. But just the system was based on some assumptions about who the public would tolerate. And our media environment has allowed us to tolerate and popularize figures that are just no match for the system that we have.

[Kibbe on Liberty Host]

So if people are intrigued, how do they find your stuff in the world work that you do?

[Ryan Holiday]

Well, Daily Stoic is a one bit of stoic wisdom every day. I do a parenting version of it also at daily dad, so dailystoic.com dailydad.com and my name is Ryan Holiday. You can get my books anywhere there are books.

[Kibbe on Liberty Host]

Cool. I really appreciate you taking the time.

[Ryan Holiday]

No, this is quite a conversation. Thank you having me.

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