Ryan Holiday

Things Ryan Says on Podcasts

Author focused on marketing, culture and Stoic philosophy. His books include Trust Me, I'm Lying, The Obstacle Is the Way and Ego Is the Enemy, translated into over 30 languages, and he founded the consulting firm Brass Check. Hosts The Daily Stoic podcast. Appears as a guest on shows including The Knowledge Project, The Rich Roll Podcast, Deep Questions with Cal Newport, EconTalk and The Prof G Pod with Scott Galloway.

Where to Find Them

Ryan Holiday hosts and writes The Daily Stoic , writes Beyond The Prompt - How to use AI in your company , writes مُلخص كتاب , hosts Stoicism: Philosophy as a Way of Life and writes WHOOP Podcast . They have also been a guest on The GaryVee Audio Experience (11 times) , The Learning Leader Show With Ryan Hawk (8 times) , The Rich Roll Podcast (6 times) , EconTalk (4 times) , The Knowledge Project (Shane Parrish) (4 times) , The Prof G Pod with Scott Galloway (3 times) , Deep Questions with Cal Newport (3 times) , Joe Lonsdale: American Optimist (3 times) , Cato Podcast (3 times) , EntreLeadership (3 times) , The Game Changing Attorney Podcast with Michael Mogill (2 times) , Young and Profiting with Hala Taha (Entrepreneurship, Sales, Marketing) (2 times) , So Money with Farnoosh Torabi (2 times) , FranklinCovey On Leadership (2 times) , The StoryBrand Podcast (2 times) , My First Million (2 times) , BiggerPockets Real Estate Podcast (2 times) , The Nathan Barry Show , The Russell Brunson Show , Prof G Markets , BigDeal , Masters in Business , Odd Lots , Into the Impossible With Brian Keating , This is Gavin Newsom , On with Kara Swisher , Motley Fool Hidden Gems Investing , PhorestFM: Building a Stronger Industry, Together , The Bulwark Podcast , Conversations with Coleman , Daily Creative with Todd Henry , Straight Talk with Mark Bouris , Recode Media , The Pomp Podcast , The Bulwark , Masters of Scale and I Love Marketing .

Recently: “Robert Greene: 99% of People Are Sleepwalking Through Life. Here's How to Wake Up.” on The Daily Stoic (November 2026); “How Will You Respond?” on The Daily Stoic (November 2026); “5 Life Lessons From Marcus Aurelius” on The Daily Stoic (November 2026); “3 Pieces of Advice Worth Keeping Close | Seth Wickersham” on The Daily Stoic (November 2026); “BONUS | Someone Else Is Spinning The Thread” on The Daily Stoic (November 2026); “Don’t Lose the Day in Expectation of the Night | It's Not Too Late, But Don't Wait (ft. Chris Guillebeau)” on The Daily Stoic (November 2026).

What They Said

“Very few military figures have ever actually been successful politicians, because they're totally different forms of leadership. One, you have authority, and the other you have to basically use the bully pulpit of persuasion and public opinion.” — Ryan Holiday, The Daily Stoic

Generalizing from the coaching example, he argues a win in one field tempts people into another that needs a completely different kind of leadership.

The Daily Stoic · 2026-11-07 Permalink → Listen →
The Daily Stoic Around 08:38 into the episode
Ryan Holiday

Yeah.

Seth Wickersham

And giving examples of the things that probably have the best chance to prove wise. You know? Well, I think I'm good

Ryan Holiday

at writing. Like on another, I'm good at putting it in writing, which is like the thing I actually like doing. Right. If you told me I had to show up for work every day at, you know, a locker room for a sports team, like that might seem cool, but I would actually hate it. I would hate it so much, like, because I would not be in charge of my schedule. I would be in meetings all day and I would be not operating in the medium that I am most comfortable in, which is the written word. So like it is really important. I think that's, we can deceive ourselves with our own outcomes. Like I actually talk about this in the ego book. Like it's very common, for instance, like someone makes a great general and then somebody says you should run for office. And like very few military figures have ever actually been successful politicians because they're totally different forms of leadership, right? One, you have authority and the other you have to basically use the bully pulpit of persuasion and public opinion. And they're just different…

Seth Wickersham

And no more so than in sports, I think, because you see it all the time where you have a good assistant coach who becomes a head coach.

Ryan Holiday

Yeah.

Seth Wickersham

And they had an expertise for calling plays or coaching pitchers or whatever it might be. But like to be a good head coach, you need to have a completely different skill set, a completely different ego and gall and, you know, fragile self-belief to stand in front of people and get them to follow…

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“There's nothing quite like a trend piece to make a trend real.” — Ryan Holiday, The Daily Stoic

Telling how Stoicism caught on in professional sports, he recalls a magazine writer turning a passing podcast mention into a story that made the trend bigger than it was.

The Daily Stoic · 2026-11-07 Permalink → Listen →
The Daily Stoic Around 05:45 into the episode
Ryan Holiday

Yeah.

Seth Wickersham

…of going through it. But that's really what that story is about. And it speaks to exactly what you're talking about. I'd be curious for you. Like, I mean, whenever I go into the office of a coach, your books are in their office. Like, what is it like being the guy that everyone turns to for wisdom?

Ryan Holiday

…I will say I had something to do with it. I remember I sent an article, like Michelle Tafoya had talked about it on a podcast. This is like some inside baseball, literally, I guess. Yeah. Michelle Tafoya talked about it on a podcast. And I sent that link to Greg Bishop at Sports Illustrated and he turned it into a piece. Like the book was, the books were working in sports, but as you know, there's nothing quite like a trend piece to make a trend real. And so that piece about it, like sort of made it more real than it was at the time. But I guess the point is like, you know, it can be very easy to be deceived by the outcome there, which is like, oh, you can decide consciously to take an ancient school of philosophy and make it popular again. Like, that's not what happened at all. Like, I was interested in writing a book about an ancient…

Seth Wickersham

Well, and I think that like that word, again, is it's wisdom, you know, when people look at you for a certain thing. And I think that like what balances, what probably makes it work for you is that you're great at explaining wisdom.

Ryan Holiday

Yeah.

Seth Wickersham

And giving examples of the things that probably have the best chance to prove wise. You know? Well, I think I'm good

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“Just because it worked out doesn't mean you're right. And by the way, just because it didn't work out doesn't mean you weren't right, because life is so much about probability. Let's say something was a good call 80% of the time and you make that call and then it doesn't work out. It still could have been absolutely the right thing to do.” — Ryan Holiday, The Daily Stoic

The guest had explained a line about not being deceived by life's outcomes. The host builds on it: outcomes are a poor guide to whether a decision was good.

The Daily Stoic · 2026-11-07 Permalink → Listen →
The Daily Stoic Around 02:53 into the episode
Ryan Holiday

…is optional. The only thing that makes a difference is action. Michael Lewis, don't be deceived by life's outcome. And then Eric Neal, who's riffing on James Baldwin, discipline, love, luck, but most of all, endurance. Tell me what each of those three mean to you and why you put them on your desk.

Seth Wickersham

…You know, but I think that like now, if you ask Brady, he would say a huge amount of my career had to do with luck and all of these things. And so don't be deceived by life's outcomes means just because you accomplish certain things, like you kind of can't believe your own internal headlines.

Ryan Holiday

Yeah, I mean, I found that too. It's like, whenever you're massive, like a friend of mine said once, you know, making a contrarian bet that turns out to be right can be a brain-destroying experience. And his point is like, if you're Elon Musk and you have this idea for SpaceX and everyone tells you it's a terrible idea and then it turns out to be worth a trillion dollars, it's hard for you later on to be informed when you do in fact have a terrible idea, you know? And I think that's a good example of like, hey, just because it worked out doesn't mean you're right. And by the way, just because it didn't work out doesn't mean you weren't right because like life is so much about probability. So like, let's say something was a good call 80% of the time and you make that call and then it doesn't work out. It still could have been absolutely the right thing to do. You know, honesty is generally the best policy, right? So you tell the truth, it blows up in your face. Do you take from that like, oh, I should be a dissembling liar? Like, no, that's the wrong lesson. And so that, yeah, I think that idea that outcomes can be…

Seth Wickersham

And outcomes aren't within your control, you know? And like there's, there's two stories in the book that kind of deal with those moments, one smaller, one very famous in the sports world. The smaller one is from the AFC championship game this past year where Sean Payton goes for it on fourth and…

Ryan Holiday

Yeah.

Seth Wickersham

And they don't get it. And that ends up being kind of the difference in the game. And he's just beating himself up over it. And then the other one famously is, you know, when the Seahawks decide to throw the ball at the goal line against the Patriots in the Super Bowl and Malcolm Butler, you know…

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“These are not objective facts. These are interpretations. These are stories we're telling ourselves about something that happened. And what the Stoics are trying to get us to see is, who's telling us that story? Sometimes it's society, sometimes it's other people, but a lot of times it's us.” — Ryan Holiday, The Daily Stoic

At a live Q&A, an audience member asked how to introduce Stoicism to someone who keeps causing themselves suffering. Ryan explains that thoughts like 'I've been humiliated, I'm ruined' are interpretations rather than facts.

The Daily Stoic · 2026-11-04 Permalink → Listen →
The Daily Stoic Around 08:25 into the episode
Speaker 4

…around the same ideas, even though they have no real connection. Like if they came to the same idea independently, that's really interesting to me and really of value. So I'm always trying to read and always taking recommendations and then trying to pay those forward when they excite me as well.

Speaker 2

…about approaching introducing Stoicism to somebody who seems to cause themselves a lot of suffering without having any real sense of awareness around it? Or perhaps at moments of breakthrough, they revert back to a victim mindset that inhibits them from having the agency and hence less suffering.

Speaker 4

That's a good question. Well, I'm supposed to do a thing tomorrow where I have to explain Stoicism to a group of five-year-olds. So I've been thinking about this. You know, to me, the core idea in Stoicism is that we don't control what happens. We control how we respond to what happens, that things outside us are objective, but our opinions about them are not, right? Epictetus says it's not things that upset us, it's our opinion about things. And I think when you talk to someone who's sort of always either causing problems for themselves or always feels like they are dealing with problems, I think one of the things we can help them do is step back and get them to see not so much how much these problems are their own creation, like it's their own fault, but how much the problem is based on their perception of there being a problem, right? That person insulted me. You know, I've been humiliated. I'm ruined. Like these are not objective facts. These are interpretations. These are stories we're telling ourselves about something that happened. And I think what the Stoics are…

Speaker 2

Thank you.

Speaker 4

I still have to figure out how I'm going to explain that to children, but hello. Hello, Ryan. Yeah, I've been following you for a while. Great fan. I want to change it a little bit, talk about death, memento mori. Okay. You've interviewed a lot of people. You know, been working on this death

Speaker 1

thing as well. What tools would you find useful for someone who's lost someone close, son, daughter, brother, whatever?

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

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