The Daily Stoic - Ryan Holiday on Bill Maher: Why Stoicism Is Having a Moment

Episode Date: September 20, 2026

Before stepping in front of a live audience on Real Time with Bill Maher, Ryan turned to five Stoic reminders to calm his nerves. In today’s episode, Ryan takes you behind the scenes and sh...ares highlights from his conversation with Bill about why Stoicism is having a moment. Watch Ryan's segment on Real Time with Bill Maher: https://www.youtube.com/watch?v=reT_s3jxYBUWatch Overtime with Bill Maher: Ryan Holiday, Andrew Cuomo, Kristen Soltis Anderson: https://www.youtube.com/watch?v=gUvynycoi3s🎟️ DAILY STOIC LIVE | Ryan Holiday is coming to a city near you! Grab tickets here |  https://www.dailystoiclive.com/🎙️ AD-FREE | Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail--Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are.--Wealthfront’s high-yield cash account: https://www.wealthfront.com/stoicThis experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Ryan Holiday, who’s a client of Wealthfront, receives cash compensation from Wealthfront Brokerage for paid testimonials in his podcast, creating a conflict of interest. More details available via the referral link. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the three month 0.75% APY boost for new clients) when you direct deposit $1,000 a month, plus open, fund, and maintain an investing account. Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms apply. Full details at wealthfront.com/promo-terms.The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of January 30, 2026, is representative, requires no minimum, and may change at any time. References to the APY for the Wealthfront Cash Account, including any APY increase, are to the APY paid by insured depository institutions that participate in our cash sweep program (the "Program Banks”). Wealthfront Brokerage does not pay interest. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY.Instant and same-day withdrawals use the Real-Time Payments (RTP) network or FedNow service. Transfers may be limited by your receiving institution, daily caps, or participating entities. New Cash Account deposits have a 2–4 day hold before transfer. Wealthfront does not charge fees for these services, but receiving institutions may impose an RTP or FedNow Fee. Processing times may vary.. Fees & Eligibility requirements may apply to certain checking features.Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Investing involves risk, including the possible loss of principal. Securities investments are not bank deposits, bank-guaranteed or FDIC-insured, and may lose value.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Starting point is 00:00:00 Welcome to the Daily Stoic Podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world. Hey, it's Ryan. Welcome to another episode of the Daily Stoic podcast. Had a cool experience a couple weeks ago. Hopped on a plane, flew to L.A., got there pretty late in night, woke up that morning, went for a long run, and then worked in my hotel room. until about three or four in the afternoon. And I went over to, I guess, what used to be the CBS lot there. And I sat down and talked Stoicism with Bill Maher on real-time with Bill Maher.
Starting point is 00:00:47 I thought actually originally they were inviting me to be one of the guests on the panel, which I've watched many, many times over the years. You probably have as well. I thought that's what they were asking. No, that was actually the interview at the top of the show, the main segment, cool. Everyone there was just unbelievably kind. I walk in the dressing room and there's an Iron Maiden
Starting point is 00:01:10 poster on the wall and an Iron Maiden shirt. The people had just been unbelievably nice. It was so cool. And look, they'd prep me for it for sure. They were like, look, he doesn't give easy interviews. It's not going to be softballs. He's going to test you a little bit. He's going to tease you a little bit. You've got to be ready for that. But they were like, look, at the end of the day, this is the stuff he's interested in. He loves history, loves philosophy. So if you can gel, like, it'll work. And one of the things I wanted to do was, like, talk to people who knew him, who'd been on there. You don't just go in their cold. So I asked a bunch of comedian friends that I know and have known over the years, Whitney Cummings, who just introduced him and spoke at the Mark Twain Award, which he was accepting.
Starting point is 00:01:58 I asked some other comedians that I know here in Austin. I got really good advice. She was like, be prepared for him to just say something that will totally throw you. And then if you can handle that, then you're good. Then you've proven you can hang. And that was pretty much exactly how it went. And look, I was really nervous. I mean, you're sitting in the green room presidents, vice presidents, actors, directors, entrepreneurs, aspiring leaders, all sorts of people have been on this show over the almost 30 years that it's been on. And I was nervous. I ran through some. I ran through. some stoic lessons before I went on. I was actually in the green room with a friend of mine, and I was sort of riffing on some stoic lessons before you're about to go on live TV in front of a live studio audience, which is pretty intimidating. Actually, here's what I put together. So I'm about to go on real-time with Bill Maher. Here are five stoic things I'm thinking about. The first is, how do you prepare? The stoics talked about premeditoshio malorum, a premeditation of evils. I talked to all the comics I know. I talk to people who know Bill. I watched
Starting point is 00:03:02 episodes of the show. Like when Seneca said the unexpected blow lands heaviest, he's talking about not being caught off guard by what might happen. So you want to know what you're in for. The second one has to do with that, which is Mark Surrealis talks about. He says, what is clapping? What is cheering? There's going to be a live audience in there. He says, clapping and cheering are the clacking of tongues and the smacking of hands. It's not worth pandering to. It's not worth obsessing over. Hopefully they like what I say. Hopefully they cheer and clap. But if they don't, it doesn't mean anything to me. The third one is this idea that ego is the enemy, which the Stoics talk about over and over and over again. Don't let things puff you up. Don't think that you're important. Don't
Starting point is 00:03:40 think that anyone knows who you are or what you have to say. Go in there and be willing prove yourself, explain yourself, make what you have to say interesting, which is another important thing. Zeno talked about how we have two ears and one mouth for a reason. You always want to make sure you don't talk over the person. You don't talk too much. You listen. It's supposed to be a good conversation. The fourth, Marks really talks about, says, a rock gains nothing by going up and loses nothing by coming down. None of this stuff says anything about you. It's wonderful to have career success. It's wonderful to be recognized. It's wonderful to have cool opportunities, but it doesn't say anything about you as a person. And I think when you think about that, it allows you to just relax,
Starting point is 00:04:19 be in the moment, and do what you have to do. The fifth one is, Epicita says you want to be able to go into every situation and say, this is what I trained for. So the question is, like, did you do the work? You just show up and have good answers on the fly. This is a result of practice. It's a result of doing the work. You don't have ego. You have confidence. You have confidence because you have done the work. And then, you know, all of a sudden, they sort of, okay, we're going to mic you up. You walk down the hall and you're standing there right in the wings. And then you hear your intro. And then boom, you're on live TV in front of a live audience. Then all of a sudden, you're out there and you're just in it. And I think we had a great conversation.
Starting point is 00:04:59 Let me bring you a chunk of that. So what do you think now here, why are you having so much success with this? Why do you think this is the moment where it caught out? To me, you know, it does kind of make sense that people who, especially the younger generations who think they're in so much pain. Yeah. We both laughed at that. Yeah, totally.
Starting point is 00:05:21 But it fits. Yes, look, I think one of the reasons stoicism is working is because it has been tried and tested over 25 centuries. It's a merciless process of the crucible of human experience testing these ideas and refining them. But I think the reason it's having a moment, particularly today, is we are seeing a collapse in the other institutions and ideologies
Starting point is 00:05:45 that used to shape and direct people. They aren't going to church as much. They see that there is a dearth of great leaders and moral examples. And so we're looking backwards to people who from a previous time seem to have figured it out, wrote something down, have something to share and teach us. And it would be wonderful if these ideas were taught in school, but they're not. And so people wake up and they go, especially, I think young men, they wake up and they go,
Starting point is 00:06:12 well, I know what I don't want to be, but who should I be? What should I do? And they're desperate for advice. And that is a void that if we don't fill, Andrew Tate fills. Did my segment that I went back to the green room, then the two guests did the main part of the show, Andrew Cuomo and Kristen Soltzitz-Anderson, uh, were on. And then afterwards, they bring you back out and you do an overtime segment where you riff about, which was all so cool. That was us talking stoicism and politics and culture, how we deal with disagreements. And, um, yeah, I thought it was great. Thanks to the folks at Bill Maher for having me on. They were so nice. They sent my grandmother, who is a huge fan of the show,
Starting point is 00:07:02 like this giant bag of Bill Marr and real-time swag. Like, seriously, the people were just so incredibly nice. It was awesome. Thanks to Bill for having me on the show. And then my plane was just delayed, delayed, delayed, delayed, delayed, delayed, delayed. I got home at 3 in the morning, I believe, and woke up and tried to have a normal Saturday with the family. And now I'm bringing you that episode.
Starting point is 00:07:24 Let's get into it. It has been insanely hot here in Texas, and we live in an old house, and the AC cannot. handle it. It just can't keep up. But you know what can keep up? What is always cool? My bed, thanks to my eight sleep pod. The pod is this smart mattress cover. It cools both sides of the bed independently. My wife's at one temperature. I'm in another one. It even gently vibrates me awake in the morning instead of an alarm. It's got built-in sensors that monitor sleep stages, heart rate, respiratory rate. It tracks your sleep, gives you sleep suggestions. And that's why
Starting point is 00:08:00 pod users report up to 32% improvement in sleep quality and up to 30% more deep sleep. Use my code DailyStoic at 8Sleep.com slash daily stoic for up to $350 off and you can get 30 days to try it at home and return it if you don't love it. I'm doing a bunch of dates for this Daily Stoic live tour. Maybe you came and saw me on one of the previous ones. Chances I was probably wearing something from today's sponsor, Quince, They make great sweaters, they make great t-shirts, they make great button-ups, great pants, just a great company. Their clothes are built to last, made with premium materials.
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Starting point is 00:09:17 365-day returns, now available in Canada and the UK to Q-U-I-N-C-E dot com slash stoic. All right, our panel, the host of the Daily Staric podcast and best-selling author of Wisdom takes work, Ryan Holliday. The former Democratic governor of New York, Andrew Cromo, and she's a CNN contributor and poll show her. That's a lot inside. Kristen's oldest. Anderson. Okay. First one is from the people for you, Ryan. Which book do you think should every American read? Good question. I heard Obama's going to have a podcast just about books. He's, you know, you know, Oprah thing. Book Club. I think it gets people reading books. Books are like dinosaurs now. What is that?
Starting point is 00:10:00 What is that? What book do you think every... I mean, this is an obvious pickp, but I think Gatsby is the greatest American novel, maybe the greatest one in English. I could not disagree more. What? You know, it's, it's, it's, it's a, okay,
Starting point is 00:10:14 it's a pretty good book. They've made it into a movie so many times, and it always sucks. And the last time, and the last time I watched it and it sucked, I went, maybe it's the book. Well, why do you think it's so great? To me, Gatsby is the American dream,
Starting point is 00:10:36 and it's also, you know, the careless people smashing things up. Careless people, yeah. The green light is the aspiration. I like that, trying to get back to a simpler time. And at the same time, we also have the carelessness of the rich, the indifference of the rich, the ridiculousness of the rich. And then, you know, speaking of books, you know, my favorite scene is they walk into the library
Starting point is 00:10:57 and he has this enormous display of books, and then Carraway finds out none of them have ever actually been open. The pages haven't been cut, which is how books were. You know, we talk a lot about books. People have opinions about books. People have opinions about The Odyssey, but if people actually read them,
Starting point is 00:11:14 they actually read them more than once, you know, I think there's something there too. I have a lot of books in my house. I haven't read. I just love the way books look. I have a whole... I do, I do. I do.
Starting point is 00:11:24 I've read books. I've read plenty of books. I've read plenty of books. But like a lot of books haven't read. Do you organize them by color? How do you organize them? Organize them by color. Wow, I'm anal.
Starting point is 00:11:33 I'm not that bad. No, I like it the fact that there's all different colors. It makes for a wall. Nothing else makes a wall, I think. It's a great look, but that's me. Book, what book would you recommend? I would recommend C.S. Lewis, the Screwtape Letters. And while it is a Christian book, it's not a, like,
Starting point is 00:11:54 proselytizing book. It's a book about what goes on in the, mind when you are being tempted away from your values and how we think somebody's temptation to do something bad is like it's obvious and instead it's about how like the little voice inside your head just tiny little things little annoyances like can lead you down a path away from what you truly believe is important i always thought c s lewis was christian proselytizing well it's a christian book and i don't think it's it's not uh it's not hiding it whatsoever but it's not a book that is intended to be about, here's why Christianity is great.
Starting point is 00:12:28 It's a book that's like, here's why the devil is. So if I read it on which page would I throw it against the wall? I don't think you would. I'm just kidding. I'm just kidding. Andrew, what's your favorite book? I'd have a book just for Democrats. You are true blue.
Starting point is 00:12:47 Reason. Even bluer. Reason to believe by Mario Cuomo. God rest of soul. Oh, gee. My father. And it is a very succinct read of what the Democratic Party is supposed to be about with the heart and soul and mission of the Democratic Party was supposed to be about. And we've lost that.
Starting point is 00:13:12 Reason to believe, Mario Cuomo. He was a great voice for it, but he was a better writer about it. Okay. That's your dad. Yep. What are your, Pam, what are your thoughts on Trump saying he will declare the straight of her? a territory of the United States. I cannot keep up with this guy.
Starting point is 00:13:34 I mean, every day, there's a new version of the straighter Hermuz. It's like Mary Hartman. I just, it's just, it's, now it's going to be a territory of the United States. Wow. Okay. But it looks like we don't even control it. I mean, it means nothing.
Starting point is 00:13:51 It means nothing. Like every other statement, it means nothing. We have peace, we have war. I'm going to bomb. going to bomb. We have a deal. We don't have a deal. What does the panel think of reports that sailors aboard the USS Abraham Lincoln have tried to jump overboard amid terrible conditions in a record 250 consecutive days at sea? That makes my blood boil. Didn't Trump say today that it hasn't been out long enough? That's what he said. His response was it hasn't been out at sea long enough.
Starting point is 00:14:19 So this is a guy that supposedly supports the troops. Is that like this is to be away from your family that long for a war we shouldn't be in at all. But by the way, we're using... He was 250 days. They haven't gotten used to it yet. That's what he's thinking. I mean, it's bizarre. I've used this phrase before, but, you know, Republicans, they have this patriotic immunity. Like, they can do things that are so unpatriotic,
Starting point is 00:14:52 and they don't seem to pay a price for it the way a Democrat would. When I hear about troops being on a ship where the toilets aren't working, and there's not enough food, and they're so morose about this that at least one of them jumped off the ship, it just makes my blood boil. This is also why it's so important that if you are going to do something
Starting point is 00:15:15 like commit American troops to a war, where war is hell, it has to be for a reason that's a very good reason that you've communicated very well to everybody who's involved and for these soldiers to feel on this ship, Not only are they being let down by the actual conditions that they are in,
Starting point is 00:15:33 but to also not feel like they're there for any kind of mission that is worth fighting. I mean, I disagree with that. There was a mission worth fighting. We fucked it up, how we did it. Iran having a nuclear weapon, Iran being the actor in the Middle East, that has fucked everything up in that region for the last 50 years. Changing that dynamic was not a unreasonable thing to try. They did it at the wrong time.
Starting point is 00:15:59 They fucked it up. They should have done it when the people were in the streets. They didn't, and now we're here with it. I will agree with you. The world is better off with Iran not having a nuclear program, that we are better off, that we have gotten rid of an enormous amount of their capability. But we've gotten ourselves into a situation now where folks are deployed in the Middle East who, you know, there are, it's thankfully not nearly as many as used to be coming home on a regular basis during Iraq and Afghanistan, but we're still losing. I know.
Starting point is 00:16:32 We're drifting away from the point, which is that we... A trillion dollars, a trillion dollar defense budget, and you can't put food on an aircraft carrier? I mean, it's just, some of it speaks to just competence, and that should go down the chain, as they say in the military. But that's almost unbelievable. You know, the first, that he didn't lay out the case to the American people before he started, I think it was a big mistake.
Starting point is 00:16:57 Because you're right, there was a case to lay out. He just didn't do it. didn't do it. It was just Venezuela yesterday and now we're going to do this. No, he did. Yeah, once he started and then we weren't prepared. We have the greatest military on the globe. How are we running out of weapons? I mean, it's incredible. Andrew, is there a legitimate, I know why this is for you, is there a legitimate, because you're in this business now, you're in the crypto business. Is there a legitimate real-world use for cryptocurrency, or is it just an avenue for criminals and corrupt politicians? I don't think they mean you by that,
Starting point is 00:17:29 But, I mean, you are in, you, this, it's so interesting to me what politicians do. Like, John Boehner left politics and he went into the pot business. He and I are in the same business now. We are. The woods, the best pot store, it's on Santa Monica Boulevard. John Boehner. John Boehner went into psychedelic. I mean, no, Rick Perry went into psychedelics.
Starting point is 00:18:00 That's his business now. Rick Perry, former governor of Texas. You went to crypto. Why would you want to get into such a dirty business? Yeah. Well, dirty business is a broad statement. 2014, I became interested in the industry. I was governor of New York. We were the first to regulate it. Because the technology, the financial technology is revolutionary and can do great, great things if properly used. This blockchain technology and these smart contracts, it can make transactions faster, cheaper, more accessible. for people. I worked with a company called OKX. We just did a partnership with ICE, which owns the New York Stock Exchange, which I believe is the most, the best exchange on the globe. He says as an arrogant New Yorker. But you will be able to buy tokenized stock 24-7 globally with tokenized securitization. I mean, it's going to change the whole industry. But it has to be done right. And it has to be regulated. And it has to be regulated.
Starting point is 00:19:03 It has to be clean. But the whole point of it is that it's not regulated. That's the whole reason they started it because they don't want regulation. Only in this country. Only in this country. Europe, 30 countries agreed on a common regulatory scheme, have a common regulator. We can't get the Senate and the House to agree for our own regulations in this country. That's what happened here.
Starting point is 00:19:28 We still don't have regulations in place. the controversy about the Clarity Act that was supposed to pass and finally put in regulations. Well, whatever it is, here, I know it's used by hackers and sex traffickers and kidnapper. What? Am I wrong? Well, it's also used by a lot more. What is the stoic view on crypto? Oh, really? Yeah.
Starting point is 00:19:52 Where do the stoics come in? Seneca's line was, it's okay to be rich as long as your money is not stained in blood. So it matters what industry you're in. It matters how you make your money. It matters who you're in business with. So I do think there's some sketchy things about the industry, and there's probably a reason that our president likes it so much. Well, I mean, that's the thing, Andrew.
Starting point is 00:20:21 That's why it has to be done right. That's why it has to be regulated. That's why it has to be clean. That's why it has to be compliant. Look, before I was the governor... We have that. Like, money itself, it doesn't... exist either. It's all about we just believe it. We just believe the bank has the money.
Starting point is 00:20:37 They don't really have the money, right? So what's the point of just having this new thing that's just in the air and in our minds? Because that's regular. You're focusing on the coins. I'm focusing on the technology. The technology is different. It's what, it's digital ledger technology. It is instantaneous. It is faster. It is cheaper. And it will allow financial transactions disruptive because it's going to reduce the cost by reducing the intermediaries. But literally, 24-7 stock market trading, bringing trillions of dollars into this country. But moving quickly, couldn't that also be a bad thing? Because I seem to remember when there's sort of a run on the market, what they have to do is freeze it because otherwise we'll go.
Starting point is 00:21:26 The exchange will still have checks. They'll still have checks on it. So can we just do that? We can stop the training. We'll go through ice, which is the largest exchange globally. Ice. Different ice, different ice. Intercontinental exchange, which owns the New York Stock Exchange.
Starting point is 00:21:46 All right. We'll wind up with this one. Ryan, are there any modern leaders who you think are doing a good job modeling Stoic virtues? Good question. Well, I think these days we obviously see more people modeling the opposite of Stoicism. You know, you have your Elon Musk's of the world. waking up every day, freaking out about things that are not in his control. One of my stoic here is modern stoic here is most of the people I read about are dead,
Starting point is 00:22:11 but I think General Mattis is not just an embodiment of the idea, but he famously carries the stoics with him on his deployments. And certainly, in watching this situation unfold now, we miss that kind of adult supervision in the Pentagon these days. Yeah, I mean, Elon, a lot of people say, well, it's the ketamine talking when he does crazy stuff. It's bad. You know, he's been, he's not, it's not out of school. He's talked about his drug use.
Starting point is 00:22:37 Is there a place within Stoicism for doing drugs? I'm asking for a friend. Yes. I might point you to a philosophy called Epicureanism. That seems more your style. But they have more in common than they do differences. All right. Well, thank you very much.
Starting point is 00:23:01 You're all very entertaining. You are a fantastic man. We'll see you next week. Thank you, ladies and gentlemen.

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