Jordan Klepper's Reading List (From Ryan Holiday)

Summary

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The Daily Stoic Podcast

Episode: Jordan Klepper's Reading List (From Ryan Holiday)
Date: March 8, 2026
Host: Ryan Holiday
Guests: Stephen, Patrick

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Episode Overview

This episode offers a lively and thoughtful exploration of notable books and the ideas they contain, as discussed by Ryan Holiday and his guests. The conversation weaves through biographies, philosophy, history, and literature, often reflecting on how past ideologies and movements parallel contemporary issues. The episode focuses on the act of reading and recommendations for meaningful, perspective-changing books, revealing how literature both shapes and is shaped by tumultuous eras—echoing the Stoic virtues of courage, discipline, justice, and wisdom.

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Key Discussion Points & Insights

1. William F. Buckley Biography and the Intellectualization of Prejudice

• Timestamps: 00:14 – 03:51
  • Stephen enthusiastically describes reading a thousand-page biography of William F. Buckley, highlighting Buckley’s complex role in American conservatism.
  • The biography reveals how Buckley intellectualized prejudices, providing “intellectual cover” for reactionary instincts:

    "People have these opinions or these instincts. How do we intellectualize that? It's a way of creating, like, an intellectual cover for these sort of like, primal, emotional, prejudiced ideas." – Stephen (00:38)

  • Stephen connects historical figures to current movements, comparing Buckley’s function to modern outlets like The Free Press. He suggests that propaganda is often about justifying current beliefs rather than introducing new, false ideas.

    "Its job is to give you reasons to believe what you already believe." – Stephen (02:44)

2. Recruitment and Ecosystems in Political Thought

• Timestamps: 03:18 – 03:51
  • Stephen and Patrick discuss how individuals with influence are identified and recruited by political movements, noting the difference in approach between the right and left.
  • Early exposure to figures like Jordan Peterson is mentioned, illustrating how thinkers are drawn into ideologically aligned ecosystems.

3. Camus, Kafka, and the Dark Energy of Humanity

• Timestamps: 04:28 – 06:13
  • The conversation transitions to existential literature. Patrick has been reading Pynchon, Camus (especially "The Plague" and "Myth of Sisyphus"), and Kafka.
  • Stephen unpacks Camus’s concept of “dark energy” as it appears in "The Plague," which he argues is a metaphor for the recurring, destructive forces in society—"it's not about the plague at all…the plague is about Nazism" (05:02).
  • Kafka's "Letter to His Father" is recommended for its insight into generational trauma and personal struggle.

    "He writes this letter sort of dumping out all his feelings about it. It's beautiful and haunting, cautionary." – Stephen (06:05)

4. Parenting Books and Literature's Practical Impact

• Timestamps: 05:17 – 06:13
  • Stephen recommends "The Self-Driven Child," and reflects on how literature can offer guidance during personal life stages, such as parenting.

5. Shipwreck and Survival Literature

• Timestamps: 09:18 – 10:38
  • Stephen shares a recent book, "The Marriage at Sea," a true survival account about a couple adrift in the Pacific after their boat is destroyed.

    "It's like about their marriage...they spend like three months in a raft...It's great." – Stephen (09:23)

  • References to classics like "Moby Dick," "In the Heart of the Sea," and Walter Lord’s book on the Titanic round out suggestions on the theme of human endurance and disaster.

6. The Absurdity of Human Endeavors: Zeppelins and Snafus

• Timestamps: 10:38 – 12:28
  • Stephen and Patrick chuckle over a book about zeppelins, using their history as a metaphor for human folly:

    "I describe this book as the definition of the triumph of hope over experience. Because they would just every single one horrendously crash." – Stephen (11:15)

  • The discussion touches on snafus and the persistent tendency for humans to repeat mistakes despite clear evidence.

7. Contemporary Philosophy and Intellectual Humility

• Timestamps: 12:51 – 14:55
  • Patrick praises Yong Chul Han’s tech philosophy, and Stephen suggests Michael Scher’s accessible book on moral philosophy.
  • Discussion shifts to Stefan Zweig’s biographies and his book on Montaigne:

    “The hardest thing to do is to remain human in inhuman times. Montaigne was all about intellectual humility in a time when they're burning people alive for being heretics.” – Stephen (13:44)

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Notable Quotes & Memorable Moments

• "When you understand William Buckley, you're like, oh, he's actually doing this thing that's kind of endemic to the conservative movement…" – Stephen (00:38)
• "The plague is about Nazism...at the end, he's like, the plague just goes on to the next [era]. We think we beat it, but we didn't." – Stephen (05:03)
• "I describe this book as the definition of the triumph of hope over experience." – Stephen, on the history of zeppelins (11:15)
• "The hardest thing to do is to remain human in inhuman times." – Stephen, paraphrasing lessons from Montaigne and Zweig (13:44)
• "It's really good. It's funny and good." – Stephen, on Michael Scher's book about moral philosophy (13:16)

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Main Reading Recommendations (with Context)

• Biography of William F. Buckley (exploring intellectualization of prejudice, conservative movement history)
• "The Plague" by Albert Camus (“dark energy” in society)
• "Letter to His Father" by Franz Kafka (personal trauma, generational conflict)
• "The Self-Driven Child" (parenting insights)
• "The Marriage at Sea" (survival and relationship tested by adversity)
• "In the Heart of the Sea" & "Moby Dick" (survival, obsession, literary legacy)
• Books on Titanic by Walter Lord; Lusitania by Erik Larson (historical shipwrecks)
• History of Zeppelins (example of collective human folly)
• Philosophy by Yong Chul Han and Michael Scher’s Moral Philosophy (tech philosophy, intellectual humility)
• Stefan Zweig’s biography of Montaigne, "The World of Yesterday" (endurance in times of turmoil, legacy of humanism)

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Themes & Tone

The episode unfolds with humor, candor, and deep curiosity about both literature and the human condition. The hosts and guests connect past and present, highlight the enduring relevance of key books, and continually return to Stoic virtues applied in real life and reading.

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For listeners seeking thoughtful book recommendations and analysis with a dose of contemporary and historical insight, this episode offers both practical and philosophical value in the style of a lively, intellectually curious conversation.

Transcript

[Ryan Holiday]

Welcome to the daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom, into the real world.

[Stephen]

You would not think that a thousand page biography of William F. Buckley would be fucking with me. Yeah, fucking with it.

[Patrick]

A thousand page.

[Stephen]

It's incredible. Really incredible. Yeah. Yes. Like, first off, just because it's like this arc of history that's fascinating. And he. All these different, like, James Baldwin's in there. He. I mean, he was the first person to publish Joan Didion.

[Patrick]

Is that right?

[Stephen]

Yes, he wrote for the National Review, but yeah. So it's this arc of American history that I think is fascinating. So basically he fondly recounts he was not invited, but his brothers, at the direction of their father, go burn a cross on somebody's lawn. Like, his father's, like, profoundly anti Semitic, profoundly racist, just a reactionary bigot. And then, so when you understand that, then when you understand. When you understand William Buckley, you're like, oh, he's actually doing this thing that's kind of endemic to the conservative movement, which is like, people have these opinions or these instincts. How do we intellectualize that? It's a way of creating, like, an intellectual cover for these sort of like, primal, emotional, prejudiced ideas. So there's the arc of that in his life. And then he starts by writing a book about liberal overreach on college campuses that his dad pays for.

[Patrick]

Is that right?

[Stephen]

Yeah, his dad was, like, an oil speculator. Okay. Then he is a speechwriter and advisor to McCarthy. And the next, he's this sort of Machiavellian genius behind, like, all these pivotal moments. It's fascinating, really.

[Ryan Holiday]

You will realize, like, oh, if you

[Stephen]

just change a couple of these names, it's the same things happening again. Yeah, but. But like, I. I think the Free Press, which I like for some stuff. Is it similar role where. It's like, part of what it does, though, is create kind of intellectual cover for things that people want to believe. Realizing that we tend to think of propaganda and misinformation as inserting false ideas. And actually its job is to give you reasons to believe what you already believe.

[Patrick]

Yes.

[Stephen]

Give you.

[Patrick]

Give you a way to not look like an asshole in conversation.

[Stephen]

Yes, yes. And kind of gives you this. It's like, okay, so the Wall Street Journal is this part of the hierarchy, and then all the way down to, like, you know, Charlie Kirk is in there somewhere, and then the Gateway Pundit is down here. But they're all doing this thing and they have various levels of funding, and it was. It was Interesting to me to watch, like, how people sought him out. Just like. Like Charlie Curtis is this average kid who wants to go to college. And some billionaires, like, you're good at this. Let me pay you to do that thing. And this basically is the same thing that happened to Buckley.

[Ryan Holiday]

Really.

[Stephen]

And then I experienced that with. When my stuff started to get popular, I would get invited to these conferences and I could see they were evaluating me. They'd be like, if you ever need anything, how could we get this out to more people? Which the left doesn't have. It tends to be, I think, more organic. But this process of, oh, this person has a way with audiences and their fellow travelers, with what we're saying, how do we bring them into the ecosystem?

[Patrick]

I mean, that's like. I feel like Peterson's an interesting example of that. Right? Early Peterson. I'm like, oh, I get this. That's a lot of sense.

[Stephen]

I met him at some of those conferences. I met him at an entrepreneur conference. And then the next thing I saw him was at a coke thing.

[Patrick]

Yeah.

[Stephen]

You know, and it's a process. Yeah. You gotta read this. I'm like, it's. You're gonna. You gotta read every page.

[Patrick]

I come down to Texas and I leave with a thousand page biography on William F. Buckley.

[Stephen]

It might be an audiobook for you then. But I'll show you my office in a second. You'll see how the notes I took on.

[Patrick]

I haven't even finished a Gore Vidal book, if I'm being totally honest.

[Stephen]

I don't know why I have either. But this is great. Is there anything you've been reading?

[Patrick]

What have I been reading? So I've been. I just actually picked up the Pynchon book on the way here, so I've been reading that.

[Stephen]

Okay.

[Patrick]

I have been. I picked up some. Some writings by Camus. I like. I like me that Myth of Sisyphus.

[Stephen]

Have you read the Plague? Yes, I just reread the Plague and it's another one where you're like, oh, this is. Explains everything.

[Patrick]

Oh, that. Yeah.

[Stephen]

I have this sort of theory about, like dark energy, that there's this like dark energy in humanity and it goes from issue to issue, era to era, and that you realize, like, oh, it's not about the plague at all. The Plague is about dark energy. Yeah. Because the plague is about Nazism.

[Patrick]

Yes.

[Stephen]

As a metaphor. But he's at the end, he's like, the play just goes on to the next. We think we beat it, but we did it. It just goes to the Next thing.

[Patrick]

I think Camus is a fun one to read right now.

[Stephen]

Yeah.

[Patrick]

I feel like that. That absurdist point of view feels. Feels good. I was also reading Kafka because of that.

[Stephen]

Ooh, did I give you. Did I give you this Kafka parenting book? No, because I remember I gave you some parents. You just had a kid. Right.

[Patrick]

And you gave me the self. What is it?

[Stephen]

Self driven child.

[Patrick]

And this was great.

[Stephen]

Did you like that?

[Patrick]

You gave me these two. Both of these are great.

[Stephen]

Okay.

[Patrick]

This makes me want to.

[Stephen]

Patrick is in an inside world.

[Patrick]

Yes. It makes. This is helpful for.

[Stephen]

Okay. Oh, yeah, sure. Okay. This is. Kaka wrote this. Oh, my God.

[Patrick]

I read about this letter. I read about this. And it's brutal, right? It's like a brutal.

[Stephen]

Super brutal. His father was kind of like William F. Buckley's father was just like one of those overbearing, powerful people. And you can sort of go two ways, you know, and he. He sort of goes in the other direction and then he writes this letter sort of dumping out all his feelings about it. It's beautiful and haunting, cautionary.

[Patrick]

He is lovely. And I feel like his short stories now, where things feel like they don't make sense. In some ways, he taps into that in such a nice way.

[Stephen]

Yeah. I don't know if you've seen a

[Ryan Holiday]

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[Stephen]

That's always the thing.

[Ryan Holiday]

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[Stephen]

I have many shipwrecked books for you.

[Patrick]

Is that right?

[Stephen]

So this one just came out. It's called the Marriage at Sea.

[Patrick]

What is this?

[Stephen]

This couple is sailing from England to New Zealand and in real life a whale breaks their sailboat apart and they spend like three months in a raft and it's, it's like about their marriage. It's a husband and wife just stuck in this raft. It's great. At one time they're in the Pacific, so it's like full of light. At one time they. They catch a giant sea turtle and they tie a rope to it and they, they try to like harness it, like to see if it can pull them. Yeah, but it's amazing. That one's good.

[Patrick]

I got obsessed with Moby Dick. It's probably my favorite.

[Stephen]

Well, have you read in the Heart of the Sea?

[Patrick]

Yes.

[Stephen]

Okay.

[Patrick]

Amazing.

[Stephen]

That's one of the all time greats.

[Patrick]

I called the Melville Estate and they let me write at his desk for a couple days. What, a pilot? Yeah, Pilot didn't go anywhere.

[Stephen]

You were writing a pilot?

[Patrick]

I was writing a pilot and I needed to get away from home and I was like, I just need to go. I want to go up to the Berkshires. And I called him on kind of a lark. I was like, you know what, I know you do some writers stuff here and there. I was like, hey, hoping they're like

[Stephen]

a Daily show fan. Was there any good energy in the.

[Patrick]

Great energy, I think. But, you know, if I'm being totally honest, the energy is. I didn't dare look at my phone for a second in that room. I felt so guilty not being productive. I was productive for two straight days.

[Stephen]

Interesting. Walter Lord has a book about the Titanic. That's amazing.

[Patrick]

Oh, really?

[Stephen]

But then Erik Larson has one about the sinking of the Lusitania. Which one is more your style?

[Ryan Holiday]

Oh, wait.

[Patrick]

The Sink of the. Wait, what is that? I don't know. The Lusitania.

[Stephen]

Lusitania is the sinking of the American ship that basically brings us into World War I.

[Patrick]

Give me that one.

[Stephen]

All right. Where's that? Found it. Dead weight.

[Patrick]

Look at this.

[Stephen]

I gave this to Ed Helms when he was here. This is about zeppelins, which. Which is, in retrospect, the dumbest idea that humans have ever had.

[Patrick]

I think so. Right, but. But a fun idea.

[Stephen]

I mean, I imagine this, but they kept. Crap.

[Ryan Holiday]

It's.

[Stephen]

It. I. I describe this book as the definition of the triumph of hope over experience. Because they would just every single one horrendously crash. Because it is a balloon filled with highly flammable gas powered by an engine. This one, like this is the famous British one. It had a smoking room inside the zeppelin. Amazing. That again, meant people were lighting lighters and matches.

[Patrick]

They brought on a fire eater every

[Stephen]

time to come in. Yeah, exactly.

[Patrick]

What I love is, like the Empire State Building has the document.

[Stephen]

Yeah.

[Patrick]

And they're like, oh, one stop there.

[Stephen]

Well, so the crazy thing about. They talk about this in the book. So, like, okay, so you tie up a balloon to this pointy needle. All right. Okay. What happens when it gets windy, as it often does. Yeah.

[Ryan Holiday]

It.

[Stephen]

No amount of ropes are going to secure this giant it. And then the people are in it, like, or whatever. It's still whatever. So it was just the dumbest fucking idea.

[Patrick]

The idea of a. Like. Like, how long was that?

[Stephen]

Like, 40 years. Like, it really. It was. Lasted a lot longer than you would think it would. It's incredible because he wrote a book about snafus. Like, about.

[Patrick]

I read his book.

[Ryan Holiday]

Yeah.

[Stephen]

That struck me as, like, just the definition of human stupidity. It's incredible.

[Patrick]

Give me a philosophy thing. I'm liking Yong Chul Han.

[Stephen]

Are you reading his stuff? No. I don't even know what you just said. Okay.

[Patrick]

Green German, does a lot of, like, tech philosophy right now.

[Stephen]

Ah. Michael Scher wrote a book about moral philosophy. Did you read that?

[Patrick]

No. Good.

[Stephen]

Really good. I bet it's awesome. Very fun.

[Patrick]

I feel like.

[Stephen]

Yeah.

[Patrick]

Funny guy. Writing a smart book like this is going to make me so jealous.

[Stephen]

Yeah.

[Patrick]

I think I looked at this book. I'm like, I mean, I bet that book's fucking great.

[Stephen]

It's really. It's really good. It's funny and good.

[Patrick]

These prints are so nice.

[Stephen]

Oh, I love this little series. And then we'll do this Montaigne book that I've been reading about. He's talking about Zweek. Wait, Zweek? I wrote he's the World of yesterday.

[Patrick]

Yes.

[Stephen]

So he's like, the most famous novelist in Europe. Yeah. Chase out of Germany the second time.

[Patrick]

Yes.

[Stephen]

And then he ends up in. In Brazil, I think. Brazil. And he rediscovers Montaigne, the French singer. And then he realizes, oh, Montaigne is writing in the middle of the religious wars of the 16th century. So it's like he's not just exploring philosophy for its own sake. He's turning inward because the world is tearing itself apart. He's saying that the hardest thing to do is to. To remain human in inhuman times. Montaigne was all about intellectual humility in a time when they're burning people alive for being heretics. And so how do you. How do you maintain intellectual humility when it's not just out of style, but the opposite is the case? And it's amazing.

[Patrick]

Wow.

[Stephen]

So good.

[Patrick]

Because Zwig was like, a 50s writer, right?

[Stephen]

Fair enough. He was popular during the first World War. So first half of the 20th century.

[Patrick]

So this was.

[Stephen]

He wrote a bunch of novels which are not that popular. And then he wrote a couple of biographies. Yeah.

[Patrick]

Wes Anderson, loosely based one of his movies.

[Stephen]

I didn't know that. I think his last one. But the World of Yesterday is a beautiful book.

[Ryan Holiday]

Yeah.

[Stephen]

And haunting. But this is. He. He would do these little biographies. Like, he wrote a really good biography of Marie Antoinette. That's good. We have one of Magellan that he wrote.

[Patrick]

Really?

[Stephen]

But the Montaigne one is his best one.

[Patrick]

Oh, I love that.

[Ryan Holiday]

Hey, it's Ryan. Thank you for listening to the Daily Stoic podcast. I just wanted to say we so appreciate it. We love serving you. It's amazing to us that over 30 million people have downloaded these episodes in the couple years we've been doing it. It's an honor. Please spread the word, tell people about it. And this isn't to sell anything.

[Stephen]

I just wanted to say thank you.

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