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The Daily Stoic

8 Mar 2026 · 13m · 5 chapters

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Jordan Klepper's Reading List (From Ryan Holiday)

In short

Host: Ryan Holiday

Description

A podcast that delves into Stoic philosophy through daily lessons and interviews with various notable figures. It emphasizes applying Stoic virtues such as courage, discipline, justice, and wisdom in everyday life.

In this episode, Ryan Holiday engages in a lively discussion with comedian and writer Jordan Klepper, focusing on literature, personal insights, and the intertwining of historical figures with contemporary themes. The conversation also touches on several notable books recommended by Holiday.

Written by AI. May contain mistakes.

Chapters

0:46

William F. Buckley Biography Insights

Discussion on the life and impact of William F. Buckley and his influence on American conservatism.

“Like his father's like profoundly anti-Semitic, profoundly racist, just a reactionary bigot.”
4:15

Literary Influences and Absurdism

Exploration of various literary works and their relevance to current events and philosophies.

“It might be an audio book for you then, but I'll show you my office in a second.”
8:11

Book Recommendations and Discussions

Discussion of various books including maritime survival stories and historical narratives.

“This couple is sailing from England to New Zealand.”
11:21

Philosophy and Historical Context

Engaging conversations about philosophical writings and their historical significance.

“It lasted a lot longer than you would think it would.”
14:02

Gratitude to the Audience

The hosts express their appreciation for the listeners and their support.

“It's amazing to us that over 30 million people have downloaded these episodes in the couple of years we've been doing it.”
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Transcript

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0:00Ryan 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. You would not think that a thousand page biography of William F. Buckley would be... Would you fucking with me? Yeah. You're fucking with a thousand page? 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. I mean, he was the first person to publish Joan Didion. Is that right? Yeah, she wrote for the National Review.

0:40Ryan Holiday: 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 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, these instincts. How do we intellectualize that? It's a way of creating like an intellectual cover for these sort of like primal, like emotional prejudiced ideas.

1:32Ryan Holiday: 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. Is that right? 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. You will realize like, oh, if you just change a couple of these names, it's the same things happening again. Yeah. But like I think the free press, which I like for some stuff, is a 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.

2:30Ryan Holiday: Like realizing that, like, we tend to think of propaganda and misinformation as like inserting false ideas. And actually its job is to give you reasons to believe what you already believe.

2:44Jordan Klepper: Yes. Give you give you a way to not look like an asshole in conversation.

2:47Ryan Holiday: Yes. Yes. And kind of gives you this. It's like, OK, 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 interesting to me to watch like how people sought him out, just like Charlie Curves is this average kid who wants to go to college and some billionaire's 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. Really?

3:18Ryan Holiday: And then I'd experienced that when my stuff started to get popular. I would get invited to these conferences and I could see they were, they were like evaluating me. They'd be like, do you ever need anything? How could we get this out to more people? There's like, which the left doesn't have. It tends to be, I think, more organic. But this process of like, 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?

3:51Jordan Klepper: I mean, that's like, I feel like Peterson's an interesting example. was that right? Totally. Those early Peterson, like, oh, I get this. Yes. That's a lot of sense.

3:58Ryan Holiday: 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.

4:04Jordan Klepper: Yeah.

4:04Ryan Holiday: You know? And it's a process. Yeah. You got to read this. Oh my goodness. You got to read every page. I come down to Texas and I leave with a thousand page biography

4:14Jordan Klepper: on William F. Buckley.

4:15Ryan Holiday: It might be an audio book for you then, but I'll show you my office in a second. You'll see how the notes I took on.

4:21Jordan Klepper: I haven't even finished a Gore Vidal book if I'm being totally honest. I don't know if I read that. This is great. Is there anything you've been reading? 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. Okay. I have been, I picked up some writings by Camus. I like me that myth of Sisyphus. Have you read The Plague? Yes.

4:41Ryan Holiday: I just reread The Plague. And it's another one where you're like, oh, this explains everything. Oh, yeah. I have this sort of theory about like dark energy, that there's this dark energy in humanity. and it goes from issue to issue, era to era. Yeah. And that you realize like, oh, it's not about the plague at all. Plague is about dark energy.

5:00Jordan Klepper: Yeah.

5:00Ryan Holiday: Because the plague is about Nazism. Yes. As a metaphor. But he's at the end, he's like, the plague just goes on to the next thing. We think we beat it, but we didn't.

5:09Jordan Klepper: It just goes to the next thing. I think Camus was a fun one to read right now. Yeah. I feel like that absurdist point of view feels good. I was also reading Kafka because of that.

5:17Ryan Holiday: Ooh. Did I give you this Kafka parenting book? No. Because I remember I gave you some parents. You just had a kid, right?

5:25Jordan Klepper: Yes, just had a kid. And you gave me the self, what is it? Self-driven child. And this was great. Did you like that? You gave me these two. Both of these are great. Okay. This makes me want to. Outdoor kids in an inside world? Yes, yes. This is helpful for New York.

5:37Ryan Holiday: Okay. Oh, yeah, sure. Okay, this is Kafka wrote this letter. Oh, my gosh.

5:42Jordan Klepper: I read about this letter. I read about this. And it's brutal, right? It's like a brutal letter.

5:46Ryan Holiday: Super brutal. His father was kind of like William F. Buckley's father. 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 a slasher dumping out all his feelings about it. It's beautiful and haunting.

6:04Jordan Klepper: 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 such a nice way.

6:13Ryan Holiday: Yeah.

6:20Ryan Holiday: So I am recording this in an Airbnb. I'm out doing a little speaking gig and didn't stay in a hotel, stayed in an Airbnb. And let me say, this place is pretty dated. I'm sure it was fancy and cool when it came out, but it's got a lot of old wood stuff. It needs a refresh. And maybe your house needs a little refresh. If you want to upgrade your space with quality pieces that work within your budget, plus enjoy fast shipping and easy assembly options, well, you should check out Wayfair because Wayfair makes it easy to find exactly what fits your style and needs. Wayfair makes it simple to narrow down to exactly what works with your style and budget.

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7:32Ryan Holiday: Shopping at Whole Foods is one of the things I do in our family. The grocery shopping is my job, so I was glad to be able to do that even on vacation. And then, you know, being here in Hawaii, it was the same Whole Foods experience we're thinking about, but then also a bunch of regional stuff, too, that they only have at this Whole Foods. We love shopping at Whole Foods because there's always new flavors and foods to choose from, whichever Whole Foods you are like, whichever Whole Foods you happen to be at. So save on regional flavors at Whole Foods Market, and maybe I'll see you at the Whole Foods in Austin sometime.

8:11Ryan Holiday: I have many shipwrecked books for you. Is that right? So this one just came out. It's called The Marriage at Sea. What is this? This couple is sailing from England to New Zealand. And in real life, a whale breaks their sailboat apart. This is my shit. And they spend like three months in a raft, and it's like about their marriage. So husband and wife just stuck in this wrap. It's great. At one time, they're in the Pacific, so it's like full of light. At one time, they catch a giant sea turtle and they tie a rope to it and they try to like harness it, like to see if it can pull them. Yeah. It's amazing.

8:45Jordan Klepper: That one's good. I got obsessed with Moby Dick. That's probably my favorite book.

8:49Ryan Holiday: Well, have you read In the Heart of the Sea?

8:50Jordan Klepper: Yes. Okay. Amazing. That's one of the all-time greats. 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. You were riding a pilot about it. I was riding 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 them on kind of a lark. I was like, you know what? I know you do some writer stuff here and there. I was like, hey, hoping they're like an alien show fan.

9:13Ryan Holiday: Was there any good energy in the - Great energy.

9:15Jordan Klepper: 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. Like I felt so guilty not being productive. I was productive for two straight days.

9:26Ryan Holiday: Interesting. this Walter Lord has a book about the Titanic that's amazing oh really but then Eric Larson has one about the sinking of the Lusitania which one is Warrior Style oh wait the sinking of the Titanic I don't know the Lusitania Lusitania is the sinking of the American ship that basically brings us into World War I give me that one alright where is that found it dead weight look at this I gave this to Ed Helms when he was here this is about Zeppelins what about Zeppelins which which is in retrospect the dumbest idea that humans have ever had i think so right but but a fun idea i mean i imagine this but they kept crap it's it i i described 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.

10:31Ryan Holiday: This one, like this is the famous British one. Yeah. It had a smoking room inside the Zeppelin. Amazing. That again, meant people were lighting lighters and matches.

10:46Jordan Klepper: They brought on a fire eater every time to come in. Yeah, exactly. What I love is like the Empire State Building has the docking point. yeah they're like oh one stop there well so the crazy thing about they talk about this in the

10:58Ryan Holiday: book so like okay so you tie up a balloon to this pointy needle all right um okay what happens when it gets windy as it often does yeah it no amount of ropes are going to secure this giant balloon and then the people are in it like or whatever it's still whatever so it was just the dumbest fucking idea you could possibly.

11:21Jordan Klepper: How long was the idea of a... Like 40 years?

11:26Ryan Holiday: Really? It lasted a lot longer than you would think it would. It's incredible. Because he wrote a book about snafus. Oh yeah, I read his book. Stupid things human has done. That struck me as just the definition of human stupidity. It's incredible.

11:44Jordan Klepper: Give me a philosophy thing. I'm liking it. Byung Chul Han. Are you reading his stuff? No. I don't even know what you just said Korean guy? Okay Korean German does a lot of like tech philosophy right now Ah Michael Schur wrote a book about moral philosophy Have you read that? No Good Really good I bet It's also very funny I feel like yeah a funny guy writing a smart book like this is gonna make me so jealous

12:05Ryan Holiday: Yeah

12:06Jordan Klepper: I think I'm like I bet that book's fucking great It's really good

12:11Ryan Holiday: It's funny and good These prints are so nice Oh I love this little series and then we'll do this Montaigne book that I've been reading about. He's talking about... Oh, Zwick. Wait, Zwick, I wrote... He's... The World of Yesterday. Yes. So he's like the most famous novelist in Europe. Yeah. Chase out of Germany the second time. Yes. And then he ends up 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.

12:46Ryan Holiday: He's turning inward because the world is tearing itself apart. He's saying that 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. And so how do you maintain intellectual humility when it's not just out of style, but the opposite is the case. And it's amazing. Wow. So good. Wait, because Zwing was like a 50s writer, right? No, no, no. He was popular during the First World War. So first half of the 20th century. So this was... He wrote a bunch of novels, which are not that popular.

13:29Ryan Holiday: And then he wrote a couple of biographies. Yeah. Wes Anderson loosely based one of his movies. I didn't know that. I think his last one. But The World of Yesterday is a beautiful book. Yeah. And haunting. But this is... He would do these little biographies. He wrote a really good biography of Marie Antoinette that's good. Really? We have one of Magellan that he wrote. Really? But the Montaigne one is his best one.

13:49Jordan Klepper: Oh, I love that.

13:54Ryan 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 of 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. I just wanted to say thank you.

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From the publisher

After their conversation for The Daily Stoic Podcast, Ryan gave Jordan Klepper, comedian, writer, and correspondent on The Daily Show, a few book recommendations at The Painted Porch.


Follow Jordan on Instagram @JordanKlepper and check out his upcoming live show dates on his website https://www.officialjordanklepper.com/


📚 Books Mentioned:

Buckley: The Life and the Revolution That Changed America

Letter to the Father

A Marriage at Sea: A True Story of Love, Obsession, and Shipwreck

Dead Wake: The Last Crossing of the Lusitania

I Survived the Hindenburg Disaster, 1937

How to Be Perfect: The Correct Answer to Every Moral Question

Montaigne

The Plague: A new translation

Outdoor Kids in an Inside World

Moby-Dick

In the Heart of the Sea: The Tragedy of the Whaleship Essex


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