Transcript of #321 Ryan Holiday - The Stoic Survival Guide New

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Ryan Holiday, welcome to the show, man.

Yeah, thanks for having me.

It's an honor to have you.

Likewise.

So, uh, yeah, this year one of my goals is to become a little more stoic as, uh, the political and world current events just continue to spiral out of control. Um, That's been one of my goals, primarily for my family. You know, it's just—

you seem stoic, though. Lowercase stoic. You seem— are you not?

I tend to lose my shit every once in a while, but as we all do. But, but yeah, I just— I want to be a little more stoic, primarily for my, my family, my kids.

Yeah, I'm the same way. I mean, I think there's some people who are sort of naturally there. And then, then you have kids and then you realize you're not there at all.

Yeah.

Yeah.

But, um, and actually several— my wife's been wanting me to do this for a while, and I'll bet it 5, 6 years ago, uh, she gave me one of your books and that's when I first heard about you and read it. Uh, it was like a daily—

yeah, the Daily Stoic. Yeah.

And, um, read through that, and then this year got Marcus Aurelius's book on Stoicism. And so this is perfect. Now you're here.

All right. So, well, I brought you a good edition of Marcus Aurelius. I don't know which one you have. This is my favorite translation. So I think what's cool about this is like, am I outta the way? Here you have the private thoughts of the most powerful person in the world. And almost certainly not intended for publication. Like he might be mortified that we're holding this right now. So, you know, most books are written for the audience, right? But this is a book for the author. Like, that it's a book is the byproduct of the philosophical process, which is like, he has a temper, he has anxiety, he has a shitty job with people he can't trust and an empire that's coming apart, and he has health problems, he has, marital problems, he has a plague, there's floods, it's a series of endless wars. And what he's doing is sitting down and writing to himself, trying to get back to center.

Right.

Interesting.

And it just wasn't burned upon his death, or it wasn't destroyed when he died. And so it doesn't read like a typical book. I mean, it's 12 books, each passage is numbered, but it's really like almost like journal or diary entries, 'cause that's what Stoicism is, is like this, you know how you're trying to be and then you're here. There's a great line in "Meditations" where he's saying like, "Fight to be the person that philosophy tried to make you." And that's what he's doing in "Meditations." Can you say that again? He says, "Fight to be the person that philosophy tried to make you," or "Fight to be the person that philosophy wants you to be." Right? It's like we all know the idea, the ideal, like what our best self is. And then we're dysregulated or we're tired or we're hungry or somebody's being really awful and annoying and we're struggling to be, to get from the lower self to the higher self.

Gotcha.

Right? And that's what this is. So I got this and then this one will hopefully, like meditations should be.

Thank you.

It should be a book that you, like most books you read, right? This should, "Meditations" should be a book that you are reading. Like it should sit on the nightstand and you pick it up and you read it throughout your life because it was written throughout someone's life. But the idea is that you don't know what passage you're gonna need until you're flipping through the book and it jumps out at you. That's the idea of "Meditations." Roger that.

Thank you.

All right, I got a bunch more. I won't take so much time, but I know you got young kids. Do you know Steve Rinella?

Yeah.

He's a meat eater. This is, I think this is, or he wrote an amazing book about hunting called "American Buffalo," which is like one of my favorite books where he gets a buffalo tag in Alaska and he goes to hunt the American bison and it's all about that. That's my favorite Steve Rinella book. But as a parent, this is "Outside Kids in an Inside World." I think that's what every parent is struggling with right now. 'Cause screens are so addictive.

Yeah.

And video games are so exciting and we're all glued to our devices, right? I mean, people are probably listening to this, almost certainly listening to this on a device right now. So, but the point is you wanna raise outdoor kids, right? Kids, he says, you wanna raise kids that don't say ew a lot. 'Cause they're good being outside, getting dirty, doing, Nonsense. That— I love that book. I think it's amazing.

Do you— you spend a lot of time outdoors with your kids?

Yeah, we live on a ranch in Texas, so—

saw that.

So we're, we're, we're pretty outdoorsy, but you know, it's a constant fight. It's like, it's like, um, they love it when they're out there, but they hate the process of getting out there.

Really?

Do you know what I mean? Like, like, it's like when we— we were yesterday, we went on a hike. They did not want to get out of the car. They did not want to go on it. And then as soon as they— we were in it, they loved it, right? And that's like, I think the struggle, uh, is the, is the, is the starting, you know what I mean?

Yep.

Um, all right, so we got that. Uh, oh, this is another interesting parenting one. This is about Churchill and his son. So Churchill has a horrible father and horrible mother, basically neglect him, becomes a great man, and he tries to do better with his son, but he doesn't do a great job. And I think, I think that's another thing that keeps us up at night as parents is like, if you're successful, how do you not raise spoiled, entitled kids? You don't. They have comforts and security and love that maybe we didn't get. But how do you make sure that that works to their advantage, not that they're to their disadvantage? Right. And so I thought it's a really interesting sort of because it looks at three generations, right? It looks at Churchill and his father. And then obviously Churchill and then Churchill and his son. It's a great book. I thought you might like that one. Have you read any Stockdale?

No, I haven't.

All right. So this is Thoughts of a Philosophical Fighter Pilot. So Stockdale goes to the Naval Academy in '43, graduates, becomes a pilot. And it's not until he spends 20 years as a, as a pilot It's not until the Navy sends him to Stanford where he gets a graduate degree that he's introduced to Stoic philosophy. On his last day at Stanford, his philosophy professor goes, "Hey, I think you might like this book." He gives him a copy of Epictetus, the Stoic philosopher, and he does 2 more deployments there before he gets shot down. And that's his sort of, he's every night in his bunk on the, on the Ticonderoga and then the Constellation and a little bit on the Oriskany, he's reading Stoic philosophy. So when he gets shot down in '65, he famously says to himself, "I am leaving the world of technology and entering the world of Epictetus." And it's in the Hanoi Hilton that he basically takes Stoic philosophy, which was a sort of, you know, a theoretical thing, and he applies it in this, what he calls the laboratory of human behavior. Holy shit.

Did you get to meet him? I see he died in 2006.

I never got to meet him. He died, yeah, I think he died in 2008 or '06. What does it say?

He died in 2006 at the age of 81.

Yeah, no, I met his children and met a lot of people that have met him, but just, I mean, one of the greatest Americans ever. Man. Incredible book. You'll love that. I was just, I'm doing, I'm actually doing a book on Stockdale right now. And this is, do you ever read "The Right Stuff," Tom Wolfe book?

No.

Oh, you would like that too. So that's about test pilots who become the first astronauts. So it's about John Glenn and Chuck Yeager, really good. But this is about, there's a little Stockdale in there too. This is like about carrier pilots in Vietnam. Not enough people know about this book, it's incredible. It's called "Over the Beach." It was Stockdale's favorite book about, about the air war in Vietnam and then the guys that get shot down. So I just read that. I think you would like that. If you don't read a lot, I think you would like that book.

Perfect.

And then the last one, you ever read any Hunter S. Thompson?

Yes.

Okay, so Hunter S. Thompson, we think of as the badass wild man, crazy guy. You think Fear and Loathing in Las Vegas is a book about drugs and alcohol, which it is, but it's the subtitle of that book is is about the American dream, because he's also one of our most astute sort of cultural and political writers. And so this is Freak Kingdom, and it's about Hunter S. Thompson as a political thinker and critic, because he covers Nixon, he covers Carter, he covers like every presidential candidate between, you know, sort of the late '60s and then his death. And, uh, I don't know, I got the sense— I think it would line up with where— because you're kind of like a man without a party. You're politically engaged, you have— you talk, but you're not like Democrat, Republican. Um, I think you'd— I think you'd like that book. It's— he— what he's primarily is anti-fascist. Not like Antifa, but anti-fascist. Like, doesn't like fascism, doesn't like people telling him what to do, doesn't like liars, doesn't like hypocrites, uh, doesn't like corruption. And I'm excited. I'm excited to have met this guy. I think you're going to like it.

Man, thank you. Yeah, yeah. Thank you. This will keep me busy.

Yeah, I think so. I appreciate it. I could have brought more. So my wife and I have a bookstore outside Austin. And so my favorite thing is when I'm going to meet someone or someone comes in, like, what books would I think they like? That's what gets me excited. So those are the ones I thought you'd like.

Thank you.

I really appreciate that. Actually, I want to talk about this one later.

Okay.

Fatherhood segment done. This is something I talk about all the time with a lot of different people, how they do it. But well, my gift is not as exciting, but this is the gummies, the Vigilance League gummy bears, legal in all 50 states, made in the USA.

All right.

Horrible for you, but they taste amazing. So But, uh, so let me, let me give you an introduction here real quick. Ryan Holiday, author of 12 books on stoicism with more than 10 million copies sold, including The Obstacle Is the Way, Ego Is the Enemy, and Stillness Is the Key. You're the founder of Daily Stoic, reaching millions through books, podcasts, newsletters, and YouTube. Your work is read in NFL locker rooms, special operations units— I can attest to that— and Silicon Valley boardrooms. In 2025, you completed your 4-book Stoic Virtue series and launched a sold-out world tour across Australia, Ireland, and beyond. Welcome to the show.

Yeah, thanks.

And, uh, so we have a Patreon account.

Yeah.

And, uh, it's turned into quite the community, and to be honest, they're the reason I get to sit down here with you today.

All right.

Um, so they get the opportunity to ask every single guest a question. This is from Corey Smith. Ryan, for people battling anxiety, depression, or the long recovery from a brain injury, when the brain can feel like the obstacle, how can Stoic principles be applied most effectively?

Ooh, I mean, I can speak more to the first two than the brain injury. That's not something I have direct experience with, but I think basically what Stoicism is at its core is this kind of distance between you and your thoughts, right? This is similar to Eastern philosophy, but it's the idea that you have the opinion, you have the feeling, you have the dread or the anxiety or the worry or the frustration or the anger, and you're trying to take a second and ask yourself, is this true, right? Like, you're worried about this thing happening, And what you're not stopping and thinking is like, hey, is my worrying about this affecting the outcome in any way? Or am I just torturing myself, right? You're not asking yourself, hey, let's say it does happen, what then, right? Because oftentimes what we're torturing ourself with is this kind of vague idea that like, oh, if this happens, that will be bad and I won't be able to handle it. But the truth is we handle stuff all the time. We've handled everything in our lives up until this point, or we wouldn't be here. We survived everything in our lives up until this point, or we wouldn't be here.

And so Stoicism is the, is, it's funny, he said, he or she said about, you know, your brain is the obstacle. Sometimes the brain is the obstacle, injury or not. Like we have biases, we have patterns, we have things that we make up. And they're not true, right? It's based on things that we haven't really worked through. And Stoicism is the idea of kind of working through that. And that's, again, what Marcus Aurelius is doing in the meditations. It's not like this magical formula that as soon as you hear it, you don't have that problem anymore. It's the, hey, I'm gonna pause and think about this and work through it and decide whether I'm going to assent to it or not. Epictetus is one of the Stoic philosophers. He would talk about how, like, he says a good money changer, like a person you would get money from in the ancient world, you know, he said they know how to tell a counterfeit coin from a real coin by banging it on the table. Like, they don't have to melt it down to test the metal. They just know, right? You have that intuition, you just know.

And I think what Stoicism is whether you're doing it in journaling, whether you're taking a few minutes, whether you take a long walk, or you're just talking through it with someone you know, stoicism is about asking yourself, hey, is this real or not? Is this true or not? Is this productive or not? Is this helpful or not? Again, this is all very easy to say, but that's what it is as a process, is to deal with precisely those feelings, which every person ever, whoever lived has struggled with in some way. Or another.

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You know, when I research— when I— and I haven't gone that too far into my research in socialism, but when I first left contracting for the agency, I was had social anxiety. A lot of people thought I was stoic. I just didn't like, you know, I just didn't like being in public, talking to new people. And so I bottled everything up. And, you know, when I read some of these books and, uh, and start digging in, it kind of feels like I would go back into bottling it back up. So I just want to ask, you know, what's it Where's the release valve in Stoicism?

Yeah, it's not bottling it up. I think, I think obviously the word stoic in English, like, so Stoicism comes about the 4th century BC. This, this guy named Zeno founds this school of philosophy. He's inspired by the cynics, and another word that we don't do great justice to in the English language. We think cynics or cynicism means sort of negative or skeptical or you know, doesn't believe in anything. Not what it is at all. And Stoicism is called Stoicism because Zeno sets up his school on the Stoapokile, the painted porch in Athens. Stoá just means porch. These were guys hanging out on this porch talking about these ideas. Now flash forward 2,500 years later when we go, oh, that guy, is really stoic, we take that to mean like he doesn't feel anything, he's a robot, he stuffs it down. And that's not what it is at all. To me, it's about processing that emotion, asking yourself, hey, is this productive or not productive? Like, is losing my shit about this, is that helping anything? Or is it in fact hurting myself, other people, making the situation worse? So it's not like, Hey, I'm feeling an emotion.

Emotions are not okay. Let me white-knuckle it. To me, it's about asking yourself, working through it. Hey, why am I feeling this way? What is this doing for me? And then I think your question about like, where's the release valve is a good one because to me, I find that release valve in the work and usually in some kind of physical activity. Like, I think you gotta have outlets for it. But the idea of just getting to a place where you're pretending it's not happening, like grief, you know, if you just go, oh, I don't feel that, that's not real. We have multiple stories about Marcus Aurelius crying, right? The most famous Stoic in the world that we don't have that much, like the historical record's relatively thin on this person. Like we don't have that many stories about him, right? And I think there's 4. About him crying. One is over the loss of a tutor, like one of his favorite teachers dies. Another is when he's told he's going to become emperor, he's just so overwhelmed at the weight of the job. He doesn't think he can do it. And then two others are about the victims of the plague.

Marcus Aurelius is the emperor of Rome during what's called the Antonine Plague, which is this devastating pandemic that kills millions and millions of people. And then another is when he's told that an earthquake has flattened this Roman city. And so like, in all these cases, he's not stuffing his emotions down. In fact, in the first story about the beloved teacher, you know, he's trying to not feel the emotion. He's like a young kid and, you know, he probably, some of the ideas of masculinity that we all know, you know, like boys don't cry, don't be a little bitch, right? Like, he's clearly upset by the fact that this person he loves has died. And one of his philosophy teachers goes to him and tries to tell him, like, you know, let's keep it under wraps, kid. And his stepfather, who's the Emperor of Rome, Antoninus Pius, He sees this and he goes, "No, no, no, no, no." He says, "Let the boy be human." And so Stoicism to me is not you never have the emotion or that you stuff it down. I think it's more like, okay, look, if you're still paralyzed by this grief a year later, you can't get outta bed, you know, that's a problem, right?

To me, it's the processing, the passing of the emotion, and then it's getting back to center. As quickly as possible. That, that to me is what the philosophy is.

Okay. Yeah, I think this book here, Meditations, is going to be very interesting.

I think you'll like it because I just—

it, it does seem— it does feel like kind of stuffing your emotions. What you're saying makes me thinking before acting. But really, you know what really got me into it is I've started bitching all the time about what— bitch— just bitching about— I mean, I'll just be honest, I haven't been happy with the last two administrations.

Sure.

But at all. And, um, I feel like I really got duped on this one. And, um, you know, and so I want to be more solutions-based and focus on actual solutions than just do what everybody else does. And yeah, let's bitch about all the problems. Let's bitch about the Epstein files. Let's bitch about the wars. There has to be— let's bitch about the stuff that we've been bitching about for, you know, ever.

Yeah.

And at least as long as I've been around. And, and there's just very few people that take the time to take the things that make them angry and, and come up with real focused potential solutions.

Well, and it's important. One of the things you hear the Stoics talk about is like getting some perspective. Right? Like, none of this is new. So Seneca is one of the famous Stoics. You know who his boss was? It was Nero. Like, his boss is the worst leader maybe of all time, right? And I got to imagine this is stressful. I imagine it's demoralizing. I imagine there's a lot to bitch about. Like, in a way, none of this is new, right? Corruption's not new. Hypocrisy is not new. Declining empire is not new. The only thing that's new about any of this is that we have a lot more information in real time about what's happening, right? Like, it was possible to get away from it in the past in ways that we can't now. It was also worse in the past in other ways, right? Like, you know, no one's being forced to, to, to fight for their life in the Colosseum, let's say. Right. There's, there's definitely some things that are better, but like, I think about even Socrates, right? Socrates, you, you think, oh, that was that guy, he wore the toga, he walked around Athens, he asked those questions, you know, must have been pretty chill.

And it's like, Socrates lives through the Peloponnesian War. Like, Athens fights, uh, like a generationally long war against Sparta and loses. Like, his country, like, loses a world war effectively, and then Athens is ruled by 30 tyrants— that literally, it's known as the Time of the Thirty Tyrants. I mean, like, the world must have felt like it was falling apart, and it was falling apart. And so I think one of the things you, you can take from the study of history— and I think, I think we all need to study history more, right? Like, people think— like, people watch too much news and don't read enough history.

Mm-hmm.

And the reason for this is like they think that being— that their job is to be an informed citizen. And it is. Your job is to be an informed citizen in America, in any democracy. The problem is watching news in real time is not necessarily the best way to be informed. And so I urge people to read more history, not because it takes anything away from the moral calamities that are happening in this moment, but it allows you to understand them in context. It allows you to understand which ones are really important and which ones are kind of par for the course, right? And it allows you to also remember that like no one has lived in a perfect society and that most of the people that you admired were looking around at the world and going, what the fuck are we doing? This is insane, you know? Like, and that actually the job is to not despair, not to get into like bitterness and anger, not to, Not to— like, one of the things Marcus Aurelius talks about in Meditations, he talks about revenge a lot. You can imagine the most powerful man in the world, if he wants to get revenge on someone, he can do some pretty heinous things to people.

But he says, you know, he tries to remind himself the best revenge is to not be like your enemy. And one of the things I look out at the world and I go, I don't like the corruption, I don't like the cruelty, I don't like the dishonesty. I don't like the pettiness. I don't like the crassness. I don't like any of this. Now, obviously, as a citizen, my job is to vote against those things, speak out against those things. But my main job as a person philosophically is to not be those things, right? Like if, if what you allow is the shittiness of what's happening around you to make you feel shitty and worse, to be shitty, like they're winning. And so I think that's, to me, that's where Stoicism really has a lot to offer because we are living in disorienting, disappointing, disillusioning times. But if you allow that to strip from you, your happiness at home, your productivity at work, your decency, your kindness, connection to other people, like, it is winning. And that's, that's kind of how I think about it.

I mean, how do you— I'm curious too, because I mean, it's, it's, you know, I brought up, I brought up politics.

Yeah.

But there's, there's just so many other— and I think that's something that everybody can relate to one way or another, right?

Yeah.

But I mean, we're going to talk about this, you know, towards the end of the interview. And I guess we'll talk about a little bit right now. But, you know, as you find success, you also find very disingenuous people that start to come around. They want to take advantage of you. Sure. They want to take advantage of your kids to get to you. They want to take advantage of your wife to get to you. They are not honest people, you know, and you throw out the word revenge.

Yeah.

And That's in my mind. I mean, revenge used to be something that, I mean, I would waste an entire day planning all the things that I could do to somebody that took advantage of me or wronged me or fucked over my family or myself or whatever, right? Whatever the circumstances are. And then, you know, back in the— a long time ago, I would act on that. Yeah, this is the best plan. Let's say we're going to do this. And then, you know, and then I realized this is just a a total fucking waste of energy.

Yeah.

And it just makes you look like an asshole, I think. And so now I'll— I can't help myself a lot of times, and I will still go through the planning phase on what I could— what can I do to get back at this person? And then I've developed one where somehow I've developed enough discipline to never act on it. That's a good first step, just to let it go.

I imagine it's— if there's an extra level of, uh, not temptation, but where you're like, I could break this person in half, you know? Like, I don't— that's not a thought that enters my head. But I imagine when you are trained to do what you are trained to do, and at different points in your life that has been unleashed, that just for— just the restraint of going, hey, that's not the— that's not the, the rules of engagement in, in the world that I'm in now, that would be like a level of like restraint that you would have to practice. But one of the things I think about is like, okay, if somebody tried to control my thoughts or controlled what I said or controlled what I did, I'd like— I'd resist that. Like, just instinctively, I'm— that's— no, I get to decide. I'm in charge. And yet we kind of hand our minds over to people all the time. Like, we let them— we let them just take up like inordinate amounts of time and space in our life. I was talking to this— talking to this writer I know, and she was saying, you know, she really didn't like what was happening politically.

And she was saying that she was having trouble. She was like, I just can't— I can't work right now. Like, she's like, I'm so outraged, I'm so upset, so pissed off that, like, I just— I can't— I can't do it. And I was saying, like, okay, but, like, if this administration came to you and was like, hey, if you keep doing your work, we're going to throw you in prison, you'd be like— like, you would— that would be so immediately galvanizing that it would fire you up, right? You would never allow a government of any persuasion to tell you what you can and can't say. Like, that's the job of an artist, right? And that's what it means to be an American. That's what's all right there in the First Amendment. And I was like, But here, voluntarily, you're doing precisely that because you don't like what's happening in the world, because it's dark or pissing you off or whatever. You're allowing it to consume so much of your mental bandwidth and your motivation that's having the same effect. Like, they might as well be putting a gun to your head and saying you can't do this, but it's actually worse because they're not doing that.

And so I, I do think it's really important that we we— you gotta have some mechanism by which you put up some walls and boundaries, and then you protect the thing that, that is yours. Like, you— like, the Stoics would say the greatest empire is like command of yourself, right? Your sovereignty as an individual. And the problem is we give that up all the time because somebody cut us off in traffic, you know, like because we opened up our phone and the news was bad. Because our parents are visiting, or, you know, whatever. Like, we just let these things get inside us and then determine our mood, determine our, you know, our focus, determine what we think about, determine our behavior. And I mean, it's not easy. It's a lot of work. And I fall down this, you know, sort of into these traps all the time. But I am trying to go, hey, like, I gotta protect, this, even if it feels good or it feels natural. I can't allow that.

Have you ever done psychedelics?

No.

Okay. Well, the reason I'm asking— Yeah, I have. I did an ibogaine treatment in Mexico 4 years ago. I haven't had a drop of booze since. Been a lot more in the moment. Um, it was very, uh, it was a life-changing experience for me. Uh, anyways, the reason I bring it up is it's, it's— there's been very few times in my life where I've been able to completely separate myself from, I guess, maybe my ego and look at things, uh, from a just a detached point of view that's maybe a different perspective of than what I'm feeling in the moment.

One of the things that I, I did this like really intense therapy thing, and I was, I was, um, you know, sort of like just vomiting all this anger and resentment I had at these, this group of people. And, um, the therapist was like, um, you know they're not thinking about you at all, right? And And he was like, they, they're just doing their thing. That's who they are. They, they have no awareness of— not only are they not doing it on purpose, um, but like, they're utterly unconcerned and disinterested of its effect on you. Like, they're not waking up and thinking about torturing you in this way. They're not waking up and thinking about abusing you in this way. They're not waking up and trying to make you miserable. They're inherently selfish, narcissistic people. Like, they're waking up and thinking about them. He's not saying it's awesome to be them. He's just saying, like, they're not thinking about you at all. And it's like, we can see this, I think, much more clearly in other stuff. Like, the economy's not thinking about you. Like, a hurricane's not thinking about you. That truck barreling towards you on the freeway is not thinking about you.

But then for some reason, because people do have intentions, and, and obviously we have to be aware of them, we do I think project a lot more intentionality on other people than is actually happening. And I think when you have someone who's like, like way inside your head, reminding yourself that you're not inside their head is really important. And then I, like you all, sometimes I'll be like, I just planned out like, a whole operation in my head of what I'm going to do if they do this. And it's like, this is a hypothetical. Like, I just, I just— my whole run, I was thinking about what I'm going to say if they say this, and then I'm going to say this, and then— and it's like, this conversation might not even happen.

Contingency planning.

Yeah. For, for, for a made-up scenario about a person that, again, if you ask them, you're like, they'd be like, who? Like, they wouldn't think about me at all. And so it's like, you're not the center of the universe, and almost certainly you're not the center of whatever the situation that you're making all about you is.

Makes sense. Also, where I was going with that is, is stoicism the ability to kind of, uh, view things not as a participant of what's happening It's just strictly an observation or observing a situation.

Yeah, it's like sometimes it's really helpful to zoom way in and then sometimes it's helpful to zoom way out. But it's like a lot of times it's like, how do I take myself out of this equation?

Okay.

And that's what ego does, right? Ego makes it all about you. It makes you at the center of things. And even just remembering that, like, everyone is the center of their situation. And that like, you're not the main character in all these other people's stories. You're a tangential character at best is helpful. He's like, yeah, why am I making this all about? Like, this was not, whatever this was, was not specifically chosen to drive you nuts. Like, and that again, it's totally indifferent to you. Like one of the ideas for the Stoics is events are objective, our opinions about them are not. Like, the situation is what it is, and then we say like, this is good or bad. I don't mean morally, like positive or negative. We say like, this is fair or unfair. We say this is like mean or cruel. We say this was, you know, targeted. We say like, we've been harmed by it. Like, the thing is, and then we decide what it means. And a lot of times the stories we tell ourselves about stuff are pretty self-absorbed, pretty distorted, and, um, like, pretty emotional. And I think, how do you get better at going, what if I could see this from another perspective or another way?

Or what if I told myself a different story about this event?

Yeah. What happens? I mean, what goes through your— when I told you, you know, oh, I'll spend an entire day planning revenge.

Yeah.

Revengeance. What happens in your head when you're wronged, when you think you've been wronged, when somebody's—

well, often at times I go, okay, um, let's say I, I pull this revenge off. In all the times in my life when I have done it, How did I feel after?

Pretty shitty.

Yeah, shitty, or at best disappointed, you know? And why am I telling myself it's gonna be different this time? And I— the idea of thinking about what you're going to think after is like a really powerful way. Do you know— you know the word Epicurean?

I don't.

That's— that, that was the rival school to the Stoics. There's the Stoics and the Epicureans. An Epicurean also in English tends to mean like loves pleasure, you know, indulges every whim. And that's not really what they thought at all. But Epicurus, what he would say, he was, let's say, more pleasure-seeking than the Stoics. He would say though, like, if you're gonna, you're like, hey, let's share this bottle of wine. He's like, you can't think about just how it's gonna feel on the way down. You have to think about how you're gonna feel after, and that part of the experience has to be put into the calculation.

Okay.

But humans are bad at this, right? Like we tell ourselves, oh, if I make this amount of money, then I'll feel secure and good. If I get with this person, then I'll feel, it'll be amazing and then I'll feel good. And people will look, if I get this car, if I win this office, if I, you know, hit this, number on the chart. Like, we, we just, we tell ourselves this lie that like this thing will do something for us. Now, the first time, or when you're younger, we can excuse this because like we don't have— although there's all sorts of wisdom out there telling us that it's not going to do what we think it's going to do for us, we don't— we haven't directly tested the hypothesis ourselves. But I think as you get older, to still be falling for that lie is a problem, right? You know, like, you know how you feel when you have a hangover. You got to take— like, that should change the drinking that you do. You know, uh, that, um, I don't know, your marriage is incredibly important to you, um, and certainly not worth a few minutes of pleasure.

And yet you in the moment are considering doing something that, you know, would, would blow that up. Or you know all your other accomplishments have never made you feel secure or like you've arrived, that there's an emptiness or a hollowness to them, and yet you go, it's different this time. Like, why do we— I mean, yeah, well, I think from an evolutionary standpoint it makes total sense, right? Like Um, if, if humans were good at being like, I'm good, I don't need any more— like, enoughness is not a great evolutionary feeling, but like insatiability makes you go on to the next and the next and the next thing. And so that can be good for the species as a whole but really bad for the individual. I think, I, I think it's We're not— we are not designed to— our biology is not inclined to make us feel content and happy and secure. And it takes a lot of work, like, to counteract that, that impulse.

How have you done it?

Um, I mean, I've— I, I struggle with it like everybody else. I, I I, I try to walk through this process like, how am I going to— like, am I— it's not that to me, like, going like, okay, hey, if I get on the other side of this, this accomplishment, this achievement, whatever, it's not going to make me feel— so it's not going to magically fill some hole in my soul. That doesn't mean it's not worth doing. I can find other reasons to do it. Like, it's challenging, it's interesting. You know, it's beneficial to people around me. Like, there's other reasons to do it. So I, and then what I find is that if I'm doing it for those different reasons, the outcome, if I'm lucky enough to get it, I feel differently about it too, because there's not a false expectation that was impossible to meet. But I think, I mean, I, I'm constantly trying to stop and go, why do I keep finding myself in this same— why don't you know— and the definition of insanity is trying the same thing over and over again expecting different results. Like, that's like the kind of the human condition.

And I'm like, why do I keep sort of backing myself into this corner, finding myself going down this lane? And then I'm like I know better than this. I'm doing it. I think I'm doing it better than I was when I was 19. But like, I'm still doing some version of it. And I think that's kind of— we're all battling these kind of scripts or these patterns that we picked up on in our lives. And we're trying to get a little— trying to get a little better at it as we go.

Yeah, it reminds me of the saying, nothing, nothing's what it's cracked up to be. Yeah. Well, how did you get into this?

I was—

Stoicism.

I was—

How about your interest?

Yeah. It's funny. I was in college. I was taking a philosophy class. And then I went to this conference. I wrote for the college newspaper. And I asked the guy who's speaking, I said like, hey, you got any book recommendations? And he was like, you know, I'm reading this guy, Epictetus. I think you would like it. And I ended up getting— somehow, I, I forget how, but I ended up with Marcus Aurelius instead, probably because I saw the movie Gladiator. And, and, uh, and I just— I opened this book and I go, what the fuck has this been? You know, like, um, this is what— like, this exists? Like, this is— this advice is there? Like, and it kind of just— it kind of just turned my world upside down.

How so?

Just, just that I think, I think all young people, anyone coming of age, but, but, but men especially in this world are looking for like the path. Like, what should you do? What should you not do? And they're looking for it in a way that like school doesn't address. They're looking for it in a way that the church doesn't address. I mean, especially, I think, I think in some ways, like, uh, uh, you know, some sports programs and definitely maybe like a military tradition, it is based on certain values and, uh, you're, you're being inducted into a way of life, right? Um, but if you don't have that, um, you know, you go away to college and they're like, you can do whatever you want. Like, you can be whoever you want, you can do whatever you want. If it feels good, it's right, you know? You just have effectively unlimited choice, right? Like, we live in a world— like, religion used to go like, hey, don't do these things or you'll go to hell. And I think obviously that puts a lot of fear and shame and control on people. That's not good. But the problem is when you, when you say, hey, do whatever you want, nothing's wrong, everything's right, trust your gut.

You know, like the last thing a 19-year-old should be doing is trusting their gut. Like you're an idiot, you know, especially like a, especially a 19-year-old dude, you know, like, and so I think what struck me about Stoicism was like, oh, this is a, This is a 2,500-year tradition. This is a tradition that's been followed by the most powerful people in the world, some of the most powerless people in the world. Epictetus is a slave, and these are people that were dealing with uncertainty and chaos and disorder and dysfunction. They were dealing with temptation. They were dealing with adversity. They were dealing with loss and pain. And Hey, they, they wrote some of their experiences down and they, they put it into a framework that, that is actually strikingly modern. Let's just say it's timeless. And I think that's what— like, sitting at the, the table in my college apartment, I was like, oh, okay, like, this makes sense to me.

And at 21 You were the director of marketing for American Apparel?

Yeah.

How did that happen?

Uh, an insane— I mean, it says more about the company than it does about me. You know, it was a dysfunctional, crazy, uh, you know, uh, shit show, really. Um, but, uh, yeah, it got to be a huge company. It was. I mean, it was a huge company when I, when I started there. I, I, I had nothing to do with it becoming what it became. But I got sort of thrown into the deep end and, and yeah, it was, yeah, my 20s were nuts, but I, I watched a, you know, a guy create a billion-dollar company and then destroy a billion-dollar company. And I watched people get caught up in it. I watched people get sort of spun sideways by it. Um, I watched people enable it, you know. Um, I enabled it. And so I, you know, in a way it was like, it was, um, it was quite an education in— I mean, it was like, it was like a king's court. Like, he was the sort of king and everyone was, you know, currying favor and wanted something. And, you know, it was, it was a— it certainly informed like what I ended up writing about a lot.

And at 25, you wrote Trust Me, I'm Lying.

Yeah.

Where did that come from?

Um, it was also, you know, American Apparel was one of the sort of most controversial companies in the world at that time. And so, you know, I, I had sort of a window seat to how the media environment worked. And then I worked with a number of other sort of controversial clients and stuff over the years. So I, I wrote an exposé on, on sort of the media system and, and marketing and PR. I mean, I basically wrote a book on fake news in 2011.

That's what it seems like.

Yeah. Yeah. I think the funny thing is I thought I thought, um, I remember trying to get the book out as quickly as possible, going like, like, this is right now. And, you know, and if anything, I was probably 10 years early. Um, but I was, I was watching how, like, the sausage got made, right? Like, how true stories got distorted and how made-up stories became true. And how people could get attention, what attention would do to people, um, the incentives of the media system. And so the book was me kind of trying to rip back the curtain on, on what that was and how it worked.

Can you go into it a little bit?

Yeah, I mean, it's, it's funny because I, I mean, I wrote that book because it is, it's now. Yeah, but it's fun. It's like, you know, I wrote that book before TikTok existed, before, um before I think maybe Instagram had just come out. Um, I was writing mostly about a world of blogs and, you know, sort of not traditional media, but like traditional media as it was being intersected by social media. And I mean, if anything, just all those trends have accelerated now. Um, but it was ultimately that what I am trying to say in the book is like, you have to think about the incentives operating on both sides of the equation, the people that are trying to get messages out and then the people who are communicating those messages, and that everyone is effectively competing for attention in this enormous ecosystem or this marketplace. And so in a world where it used to be, okay, half the world, half the country subscribes to the New York Times, half subscribes to the Washington Post, Now both these papers have an agenda, there's a bias, but like mostly they're trying to deliver value for the subscribers of the— of this paid product.

And they're putting out a, you know, a 40-page newspaper where once you buy it, um, all the information is there, right? Like if you look at like the headline in the New York Times for the Pentagon Papers It's like there's no sensationalism in it, there's no crazy— because like you're not buying the New York Times in Grand Central Station with a newsboy like shouting like, extra, extra, read all about it, right? Which was the media environment in the late 1800s and early 1900s. And so basically what the internet did is it broke all that apart. And it made it so every story, every headline, every article, every clip is competing with everything else out there, right? So it's like, what's the craziest? What tells people what they want to hear? What pisses people off, right? What offers the most certainty? That's what drops, like an analogous way, like what happened in the early to mid-2000s, is akin to what's happening now with podcasts, like, which I'm sure you've experienced, which is like there was this period where podcasts were long-form interviews, um, that subscribers of that podcast listened to, right? So you have all the subscribers to this show and you think about like delivering high-quality guests who you have a long-form conversation with and people listen to the whole thing.

And then what's been happening the last, I don't know, 2 years is like the sort of the clip economy, right? Where now it's like about the most sensational clip. Like, so that 2-hour conversation is distilled down into a 20-second clip or whatever. And what that's doing is creating, as I'm sure you're seeing it with peers of yours, is like a lot of competition for like the craziest clips, like gotcha moments, or Or conversely, like, you're just having the same conversation, but then people are coming and cutting out those clips and spreading them. And so it's create— it's now it's creating a lot of pressure and a lot of noise and changing the incentives of the medium. And so what I was writing about in "Trust Me, I'm Lying" was that sort of first wave of that happening where like, now you don't read a website, you read articles from that website. And you only read them because it's showing up in your Facebook feed or it's showing up on Twitter or it's because somebody emailed it to you, right? And that's creating an incentive, a bias towards certain kinds of emotion. Like for instance, they found that like the valence of the extremeness of the emotion is like the number one predictor of virality.

So like something that makes you feel pretty good is not gonna be shared as something that makes you extremely angry. Or something that makes you kind of angry is not going to spread as well as something that makes you laugh really hard. And so it's creating this incentive for extremes, right? So everything becomes an exaggerated, you know, distorted version of itself to meet that. And then you layer on top of that, like, this is the first— in the sort of blog world, one of the first kind of big breakthroughs was like reporters or influencers or what you, you were, you were— your job performance was like how much traffic your article got or how many views your video got, right? Um, which is different than how journalists had basically been paid for the entirety of the institution. Um, and so in the same way that you wouldn't want a journalist to own like shares in a stock that they were reporting on, Um, now they own stock in the story. Like, they want— instead of being like, hey, it's complicated and we don't know, which isn't going to do well, they're like, it, it shapes the story that they're writing.

And I think what we're seeing now, now that people are working for outlets less and less and working for themselves more and more, like Are you gonna tell your Substack audience what they don't want to hear? Are you gonna have a guest on, like, not you, but like you can imagine someone in a different financial position. You're like, hey, when I, when I have these kind of guests, my Patreon numbers go down. And when I have these kind of guests, my Patreon numbers go up. Or, you know, donations go up when I do this and they go down when I do this. And so now again, these financial incentives are acting on the information that people are getting. And people are not good at evaluating the reliability of the person they're getting information on. We're just really bad at it.

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I think we've lost that because I think, I think that the thirst for real information has significantly, significantly diminished because now people are more concerned with confirming their opinions and their own thoughts.

Yeah.

And so rather than actually search for some kind of truth or really try to figure out what the hell is going on, what's at the bottom of this, instead of doing that and spending the time to research and hear other opinions and perspectives, they, they immediately sift through everything they possibly can to find the one person that, yeah, is going to tell them everything that they're thinking. Is correct and they should. And then it turns into they tell them how to think.

Yeah.

And, and it's, it's become like this lazy search for, for just confirming your own biases, opinions, and thoughts.

Yeah. And, and there's always going to be someone who will fill that need. So like, we saw this like in the aftermath of the 2020 election, right? It's like Oh, if you're not gonna tell the audience what they want to hear, then they're just gonna go watch this channel. And if that channel isn't gonna do it, they're gonna watch this channel. And so it's hard, like choice is good, but the problem with choice when it comes to information is that you're creating a market incentive for people to lie to you. Typically that incentive is mitigated, or by the fact that the media outlet is owned by a big company, or the reporter themselves is a salaried employee who identifies as a journalist or a writer or whatever. They're— it's different when it's like, no, no, like, I write for Substack and I am directly dependent on how many subscribers I have. Paying subscribers. So like audience capture, there's fewer intermediaries between the creator and the, the sort of payment structure. Now, in many ways, this is great for creators because there's fewer people taking, you know, picking their pocket along the way. But it also means that they are directly exposed to, um, some perverse incentives.

Like audience capture is right there.

There's an influence.

Yeah.

And, and like, it takes a person, it takes, it takes some character and some self-control and some ideals to be like, no, no, no, no, I, I, I have an audience. The audience doesn't have me. Like, I say what I think needs to be said, not what's going to do well.

That's what I try to do. I think that's what you do too.

Yeah.

I mean, do you think that— because I've always been more of a long game person than, than a short game, and so I see exactly what you're talking about all the time. But, and I would say that the majority of those people don't last very long. Eventually it patters out. And but by being, being true to yourself and not being beholden to an audience or financial incentive or whatever, I mean, you're, you're going to do this and it's a fucking roller coaster.

Yeah. Yeah. They're, they're outraged about this and then, oh, no, no, we're not outraged about that anymore. Now we're outraged about this. And no, no, actually, I never said that. Like, they're— you're, you're surfing you're surfing the audience, and it's both exhausting and also it just doesn't feel like success to me, right? Like, if, if success is like, I have to tell you what you want to hear, then like, I work for you.

It's boring anyway. I mean, just to, to sit in here— I mean, I get a lot of people pissed at me right now because I've leaned across the aisle, because I like, I like new perspectives. That's how shit gets done. You know, and, and, but I just don't, I just don't fucking care, you know. It's, I'm like, this is, it's what I'm gonna do. I'm just, you're— I'm not going to be beholden to anybody on who I talk to and do not talk to.

Yeah.

And, and I'm— it's boring to me to sit there and talk to somebody that has the exact same opinion to me over and over just to confirm to each other that we're the— we're in the right way of thinking. But I'm curious how you navigate it because I've, you know, when I started this thing, it was just military guys and, you know, intelligence folks and people that I'd worked with in the past. And I really just wanted to kind of correct the record and actually have people that had been in the events that these reporters were talking about. Yeah, well, actually, here's what actually happened from a guy that was there. You know, and, um, and then we started talking about political issues, issues with kids, like lots of different problems that society faces. And it would be a discussion inside one of those.

Yeah.

And then, uh, to make a bigger impact, I actually started going to this— to the, to the lawmakers. Yeah. You know, to the people in charge, people that can make a difference. And, um, and then I realized they all just lied to you, you know, and they use the platform to advance themselves. And so now, now I'm extremely particular. I even have friends that are running for Senate, for Congress, for whatever places in the administration, doesn't matter. Yeah, you know, and, um, I won't have them on. Interesting. Because I just You're just gonna tell me what you think I want to hear and what I think my audience— what you think my audience wants to hear.

Yeah.

And then even if you do have great intentions, I've seen it too many times, you're going to get in there, you're not going to make an impact, you're not going to. They're going to own your ass.

Yeah.

You're not going to be put on committees if you go against the grain, and you're just going to turn into the same shit that we see every, every single time.

Yeah.

But if you do hold true to your word I'll help you with your reelection.

Yeah, you know, that's interesting. Yeah, I think deciding, deciding what you're gonna be a part of and not be a part of, to me, is like what it's kind of all about. And, um, I think I've been amazed at the degree to which, um, people I know don't think about like, hey, is this a good person? Do I agree with them? And just not to just agree with them, but like, are they a bad actor or, you know, uh, someone at least operating from good faith, whatever? And they just think about like, how's this gonna do, you know? And like, to me, success and a platform comes with responsibilities. Not just like, hey, how do you look yourself in the mirror? But like, people are, if they see you have someone on or they see you writing about something or talking about something, like they assume that it's not a cosign, but you're participating, right? You're like, they go, oh, they wouldn't have this person on if they were psychopath or a lot— like, people— like, I just think there's a responsibility that comes from having a platform or having influence. And it's a huge responsibility.

Yeah.

People make decisions based off what's said in this room.

Yeah.

Like, life-changing decisions.

Yeah. Yeah. There's, um, there was— I remember finding when I was writing Trust Me, I'm Lying, there were some, some— and it's funny, none of this stuff is new. There was this media critic, and he was writing in like the late 1800s, early 1900s, and he says, you know, American— America is a country ruled by public opinion. That's what a democracy is. And he says, therefore, what determines public opinion rules America. And so the people that own newspapers, yeah, sure, it's a for-profit business, but like they are responsible for something that in a way affects like the whole country, and that there has to be a response. He was saying there has to be a responsibility, that these things are kind of public trusts. And look, I'm— again, I think you get in real problem territory when the government is deciding, you know, like, I'm not saying it should be like this, this isn't something that should be legally policed, But like, if the people with the platforms are not policing themselves, that's a problem, right? Because then basically people without character, people with, um, agendas, they can take advantage of that. You know, they take advantage of that.

And, and we're so consumed in America by like our political disagreements that we forget that there's, there's people outside America that are also trying to steer and navigate this discourse, right? And just as, by the way, historically we have done that in other countries. But like, we seem to think that like the only agenda someone could have is like left or right, not like Russian, Chinese, Iranian— like, like, our, our enemies see these gaping holes in our media system. They see these people who are basically, uh, available to the highest bidder, and they're like, do I want to go to war with America, or do I want to make America go to war with itself? And I think one of the things I was trying to write in Trust Me, I'm Lying is, is like, hey, look, Here's how I'm getting you to buy t-shirts or getting you to follow this brand or this person or whatever. But like, real bad people can do these same things and in fact are doing these same things. And I think that to me though, that even the craziest part of our system isn't just like that bad actors can do, but also like the system can manipulate itself just like, like it's so primed for, for like going to where the energy of the action is that sometimes things that start as jokes become real things, or things that start as the most harebrained conspiracy theory that you could imagine, like, becomes real.

Like, I, I live in, in this town called Bastrop, Texas, and one of the first ones that really caught my eye on this— do you remember the Jade Helm? Conspiracy? No. There was this conspiracy that, like, this is during— this is 2015, so it's during the Obama administration. They were doing like these big training exercises in like the South and the Southwest, um, and, uh, this conspiracy theory comes out that like it's actually this false— it's like this crazy operation where they're gonna like, um, I don't know, the federal government was gonna like occupy the southern states. It was like the faux military training exercise as a pretext to to like start a civil war or something. It was this conspiracy theory that starts online, starts on Facebook. And, and one of the exercises was happening in where I live. And, um, and like the governor of Texas ends up sending the National Guard to observe the exercises to make sure this didn't happen, as if, as if, uh, yeah, that could do anything. Uh, but, but, but anyways, the point was it it came out in the years after that this was mostly like a foreign sort of propagated theory, like that, like this thing, some crazy person online said this and then it was injected from a foreign influence.

And then, yeah, exactly. Like they went and they put, they put energy behind, they put spend behind it and spread and whatever. And so it was like, oh, okay. So again, we're so consumed with like what we're doing to each other that we don't think about the fact that other people have an even bigger incentive to get us really focused on this or that. And so again, you know, countries that are real close to Russia, like Finland, they spend a lot of time teaching media literacy to their kids because they know that it's real, and they know that these operations and this agenda is right there all the time. And I think we, we live in a bubble, uh, because we've so often been the exporter of culture that we don't think about the ways that, you know, different, uh, nations, causes, etc., have a vested interest in directing that culture in certain ways. And so that's one of the things I was talking about in the book too.

Yeah, I've, uh, I mean, I've, like I said, I've changed my tune since the last election. And you know what I've realized is I think, I think that the— you can have a better, bigger impact in just initiating, in how you initiate certain conversations rather than who you initiate them with. If you start the conversation properly and plant the seed, then it, it will grow. It will grow into what it needs to be.

Yeah.

Instead of trying to hit the head honcho and, and pour your ideas into them and, and hold them accountable.

Interesting. What do you mean?

I mean that— what do I mean? I mean that I've just Everybody I've brought on here that, that, that, that can make an immediate impact, that is in a position to make an immediate impact, they always fall short.

Okay.

No matter what they tell you. But what I have noticed is the things that, that, that just in my own personal experience with some of the discussions that I've had in here, the biggest impact that we've made is by starting a conversation and watching the conversation grow through the, through regular people, through the population, not, not from getting direct to a president, a congressman, a senator, a CEO of a company, uh, somebody that owns a nonprofit, whatever. It's, it's the conversation that happens that, that engages the population has a much, much bigger impact than going directly to the decision maker.

Have you heard that expression that politics is downstream from culture? No. I think that's sort of what you're saying is like, uh, what matters is the consensus or the idea, like the, the energy, the vibe is more important than like a single decision maker, which is, by the way, our whole system. Like, we have a decentralized system, so where decision making is decentralized and widespread because the founders were so concerned about sort of man on horseback. Yeah. And, and so there really isn't one singular person who can make a difference. Now, the problem is that has also allowed a lot of people who are in positions of power to abdicate their responsibility to make a difference, right? Like, everyone, everyone is trying to save their jobs for some point in the future when they'll be the decision maker, you know? And, um, like, look, you do need those people, but chances are you're not that person. Yeah, like, chances are you should do the right thing right now.

Yep. It's interesting. It's interesting. I think— what do you think it is? I think it's addiction to power. But then looking at it from the outside, and it does appear that they have a lot of power, but then when you see it and you're like, you're, you're fucking completely powerless because you're not saying what needs to be said, even though you know exactly what the fuck you need to do, because you want to hang on to the fake power that you think you have. But you're actually powerless because you're not saying what you know needs to be said, because you know you won't have that position anymore when that position represents your power.

Your relevance in society.

I think the difference here— there's, there's power and there's status, right? And so, um, they don't exercise the power because they want to keep the status. Like, I mean, look, Thomas Massie is, is, is not going to be a congressman much longer. Um, the irony is when you meet a lot of these politicians privately, not only will they tell you a bunch of things that they won't say in public But they will also tell you how much they don't like their job. Like, they fucking hate it. Like, it's a miserable job. They don't like their colleagues. They think there's a lot of, you know, performance, and they have to spend all this time fundraising. They don't like the job. And yet when it comes down to these votes that seem to me to be very clearly conscience-based or very stark moral choices, um, they're like Well, I gotta do what I know is wrong to keep this job that I don't fucking like. I'm like, I don't get it at all. It doesn't make any sense to me, right? But the problem is, I remember I was sitting in the Senate dining room talking to, um, uh, a senator, and, and I was saying like, hey, why don't you guys— you know, you and I probably have very different politics, but I was like, why don't you know this Trump thing is crazy?

Like, what are we doing here? And, um, I was like, why don't you speak out about it, you know? And, um, and he goes, see that guy over there? And he's like, yeah. And he's like, that guy was going to be head of the CIA. And he's— and I go, okay. And he's like— and then, uh, I could probably say who it was. He said that, that, uh, the White House was like adult daycare over there. I think it was Senator Corker. And he's like, he's not even going to be a senator anymore. You know, he was like, that guy was in line for the next office, the next level, and he made a comment and, uh, it's not happening anymore. And the guy was basically saying like, that's, that's why. And he was laying it out for like, like, it's, it's just, it is crazy because like me as a citizen, I'm like, you're one of the, uh, you know, 100 most powerful people in the world. And that's not how they see themselves. And so I don't know, why would you want— I, I— and look, I, I write about this. I wrote this book on courage.

I talk about— I was once, when I was at American Apparel, I was once asked to do this thing that was profoundly wrong and immoral. And, um, and, uh, I didn't do it, but I thought about doing it, and I struggled with doing it, and And the reason that I didn't, I didn't like challenge my boss about it was that I didn't want to get fired right now. In retrospect, why would I want to keep a job that speaking up about something that was wrong would get you fired from? That's crazy. It doesn't make any sense. But this is, these are the equations that we make in our heads. But why would you want to work in an administration where even the slightest criticism gets you on the shit list, it's not going to be a good job. This thing, this job that you dreamed of having your whole life, it, it's not what you think it is, right? Like, they just showed you it's not what you think it is. But, um, we rationalize where everybody, everybody is saving themselves for this higher calling, this higher call. Yeah, yeah, yeah. Uh, I remember, you know, Adam Kinzinger?

Mm-hmm.

I remember he was saying he felt like a lot of— I was talking to him once and he was telling me that he feels like members of Congress tell themselves there's a super Congress and their job is like that super Congress will take care of it. And it's like, no, no, you were elected to take care of this. This is what we sent you to Washington. We didn't send you there to be in the job for as long as you could have it. We sent you there to represent our interests and to solve the problems of, uh, governance, right? That's the fucking job. And you think your job is to continue to be congressman or congresswoman, and, um, you're so afraid of being the former senator from Massachusetts or the former congresswoman from California that you aren't making the tough decisions that you have to make. And look, one of the things I've been trying to remind myself of is like, it is very easy as citizens to be like, why aren't these people risking their jobs to do what is right? And why aren't they putting themselves out there? And then it's like you, and by you, I mean like the person listening, You are working a job you fucking hate and you know you could be doing something different or better.

You work, you're working in an industry that you know is fucked up, like blah, blah, blah. What was the last risk you took like that? Like, it's, you know what I mean? It's very, it's very easy to evaluate the moral choices and the complicity and the contradictions in other people. And of course, as citizens, it's our job to do that and to throw those people out. That's— that you cannot— we cannot keep this republic, as Benjamin Franklin said, if we don't do that. However, to me, the main— in the main purpose of looking at this, the coward— cowardice and the contradictions and the shamelessness and the, the sort of petty turf wars, is, is it— it should, it should be a mirror reflected back at ourselves and go Well, I could be doing more. Like, I could be— I tell my kids to follow their dreams, and then I'm like not doing it, you know? And so I, I don't know, I just think it's really easy to kind of just point this like judgment lens at Washington or the State House or whatever, but ultimately you got to point it at yourself.

Yeah, it's interesting you bring that up because I wanted to talk to you about hypocrisy, being a hypocrite. I'm sure we all are. I mean, I'm real—

every single one of us.

Yes, real quick to point it out in everybody else, but I do do a lot of self-reflection and I talk to a lot, you know, how can I improve? But I'm always thinking about that, whether it's being a dad, being a businessman, being a pod— whatever it is, you know. And, and I can't find the— I can't find my own hypocrisy. Does that make sense?

On, on—

I don't know what it is. I don't know. I mean, now I'm sure it'll show up in the comments section.

The comments can be helpful for that.

But, uh, but I don't— I, I can't see it in myself. A lot of times I can't see it in myself. Right.

Yeah.

Right now.

No, no. I mean, look, this is why, this is why a, a company's gotta have a board of directors. This is why a president is supposed to have a cabinet. I think the most alarming thing about where we are politically right now is that not only are a lot of the governmental checks and balances not there, but a lot of the, a lot of the cultural checks and balances aren't there. Like, the press is supposed to be hostile to power, and the cabinet is like the founders set up a system, um, where ambition was supposed to be a check against ambition, right? The, um, Congress was supposed to zealously enforce its prerogatives. Like, part of being a senator— like, part of the perk of being a senator and having a 6-year term, whereas the president has a 4-year term, is you're supposed to be able to go like this to the president when the president is wrong. Right? Like, Congress has warmaking powers, not the president. But if Congress decides that they don't want to enforce that power, then the president has that power, right? And, um, you know, if, if we have a partisan news environment where the left-wing media slobbers all over a left-wing president and the right-wing media slobbers all over the right-wing president.

And then if the president has a cabinet and has been allowed to confirm a cabinet of people who are dependent on him and, um, fully bought in on him, then the president's never going to hear no and never going to hear, uh, that's a dumb fucking idea. Like, uh, What about this? What about that? And so, I mean, we know historically what happens when people in positions of power are not subject to any checks and balances and when their information diet is degraded. Like, one of the oldest stories that we have about this is that the emperor has no clothes. Right? And when everyone says, hey, sir, we love your new outfit, and he's walking around naked, that there was a, there was a reason, there's a moral to that story. And it's funny, actually, Marcus Aurelius, the reason Marcus Aurelius becomes emperor is actually like 2,000 years earlier, an illustration of that story. So Hadrian does not have a son. He's the emperor of Rome. He doesn't have a son. So he has to choose his successor. And there's this kid, he's a member of a sort of prestigious Roman family who somehow he meets.

That kid is Marcus Aurelius. And for some reason, Marcus Aurelius as a young kid just doesn't seem to be intimidated by the emperor at all. And he tells him the truth. And you can imagine that the emperor of Rome does not hear the truth very often. It's actually a famous story about Hadrian where Hadrian is in an argument with one of his advisors who's a philosopher, and, uh, some— it's like, it's, uh, we don't know exactly what it was about, but it was something where it was like, it's like an objective, you know, like, uh, anyways, the philosopher ends up saying, you know what, sir, you're right, you're— I was wrong, you're right. And, um, later one of his friends comes up to him and he says, you know, why did you tell the emperor he was right? Like, Like, the math equation is very clear. He's wrong. And the philosopher looks at him and he says, ah, this is what you don't understand. The man who controls 50 legions is always correct, right? Like, people don't tell powerful people the truth because they are afraid of powerful people, right? And, um, Marcus Aurelius supposedly tells the Emperor Hadrian the truth, and his nickname is Verissimus, like the truest one.

Part of what what makes Hadrian ultimately select Marcus Aurelius is that he is like the boy in the story The Emperor Has No Clothes, who actually says to the emperor, sir, you're naked. What are you talking about? Like, I don't care what these people said, you don't have any fucking clothes on. You got conned, right? And so you, as you become powerful and important, and as you— this is why revenge is bad— when you get a reputation for punishing your enemies or punishing your perceived enemies, like critics, um, it degrades your picture of the world because you have just sent a message to everyone around you: do not challenge that person, do not tell them the truth, do not tell them what they don't want to hear. Like, do you think there were many advisors who told Putin that invading Ukraine would be a bad idea? Like, do you think anyone laid out like, this is how bad it could go? No, no, because you don't want to end up fucking in a plane crash, right? Or like, uh, you don't want to fall out of a 4th-story window. And so oftentimes you think you want control, you think you want, uh, people on board you think you want true believers, um, and you don't.

Like, the antagonistic, uh, hostile— like, the, the system of government we have is set up there for a reason. Even, even the so-called deep state is also there for— like, you want career governmental employees who are not necessarily political. I mean, there can be problems with it too. I'm not— I don't mean to overstate it, but like You want a bureaucracy that doesn't want to swing too far in one direction or the other direction. You want Congress to be oppositional. You want your cabinet to, uh, have their own political ambitions. Like, Lincoln staffs his cabinet with his political rivals because he wants he knows that what he has to do is extremely difficult. And if he only has people telling him what he wants to hear, he will not actually be able to do it. And so that, to me, is what alarms me about where we are.

I'm just— you brought up an interesting point about— I mean, where do you draw the line between sending a message, maybe not revenge or vengeance, but sending a message, Because I've done this where, where I, I will never initiate— I shouldn't say never. I will not initiate arguments, blast people, get in fights on the internet. I just think this shit's stupid and it's a waste of time and causes a lot of stress. But there have been times where powerful people come after me. And then I think it is not just— I, I think it— from— for a variety of reasons, I think it's important to stand up.

Yeah.

And to engage. One, to set an example to anybody else out there that's planning on coming after me. If you do come after me, this is what the fuck's gonna happen if you back me into a corner. I think it also gives other people Courage. I just went through one of these at the beginning of the year. A congressman, um, went after me and I went right back at him, and now he's no longer in fucking Congress. Yeah, but you know, I did that because, uh, I, I mean, I started this in my attic, so I still— I, I don't— I'm still coming to the full realization of the magnitude of the shit that can come out of here because I still consider myself that guy in the attic that was doing this with my wife. It's a small thing. And but so I'm kind of in the middle of, you know, does that make sense? But I also did that because I wanted to show people like, you don't have to get fucking pushed around by these people, man. Yeah, they're going to come after you. And it is scary to have somebody that high up in government coming after you.

But they don't have as much power as you think they do.

Yeah.

And I just proved that.

Yeah.

And at the same time, I don't want to, you know, for, for, for my immediate team, like, I, I ask anybody that's been here for a little bit, you know, that's especially the guys that have been here from the beginning, which is only a handful of them.

Yeah.

You know, I'm always asking them like, hey, what do you think of this? Am I off? Am I off on this?

Right.

You know, and I think they tell me, you know, especially my top two guys tell me, they tell me.

Yeah.

But, you know, I don't want to— do you see what I'm getting at?

No, totally. Look, sometimes you gotta establish some deterrence or you get, you get pushed around. I think that's important. Um, but yeah, I, I do think what we're talking about culturally is the problem. Like, we, we want people to stand up, we want people to to do the right thing? And then what examples do they have of that happening? And I think we're in like almost like a cultural death spiral of a lack of those examples. And so I do think it's important, um, but making a martyr of yourself, you know, is, is usually not a great thing to do. But like the idea that like there are more people out there that feel this way than people think is really important. And because it's so easy to think like, oh, everyone's going along with this, everyone's okay with this, like, this is just— this is just what we have to put up with. And, and I think it's important, like, acts of courage— like, cowardice is contagious, and so is courage. Um, moral courage and physical courage. Like, if you see someone else do it, it changes your sense of what's possible and what, um, is sort of, uh, the cultural expectation.

And I think when I say we're in a death spiral, it's like, it's like everyone is saving themselves for some crisis And it's like, dude, this is the crisis. This is it, man.

What are you—

how much worse are you expecting it to get? And look, like, the Stoics are not exempt from this. As I said, Seneca works for Nero. Now, Seneca probably told himself he was the adult in the room, that he was making Nero less bad, and that he prevented Nero from doing a lot of bad stuff. And he almost certainly did. Um, but as a result, he also allowed Nero to do a lot of bad stuff. And these are not easy moral choices. Um, and I— the only reason I think, like, 2,000 years later it becomes a little clearer, right? Um, but in the moment, they're, they are vexing, uh, emotional and moral choices. And when you're asking someone to choose, hey, you're going to lose your job over this, you're going to be attacked, maybe your family will be threatened. These are a lot to ask of people. I get that. But chances are when you look back, you're going to wish you did more. You're going to wish you said more. You're going to wish you— you're not going to be like, I'm so glad I waited. And Because here's the thing about waiting is that you can always tell yourself that this isn't the right time.

That like, again, no, no, no, no, I need to be, I need to stay in the room till the real crisis happens. And what you've actually done is over and over and over again built the habit of not doing the thing. Right. And, and, and, um, the idea that suddenly when you're at the second to the top level, that's when you're gonna gamble it all and, and do the hard thing. Like, you, you have to build it as a— how, like, Aristotle said that it was wrong to think of virtue as this thing that you have or don't have, like that people are born courageous or born generous or you simply are, uh, you know, smart, or, you know, any of the things that we hold up as good. He's like, no, no, it's an— it's a verb, not a noun. It's a thing you are doing or not doing. Like, courage is a muscle you are exercising. Like, speaking truth to power is a muscle you are exercising. It's a thing you are doing, not a thing you are or aren't. And so the, the, the, the good news about that is like, if you want to be generous, if you want to be a generous person, you can start right now.

Like, start tipping bigger, like tie the percentage of your salary, right? Um, you can start doing that right now. The, the— that's the good news. The bad news is if you are not doing it, you are building the habit and the muscle of not being that person. And it becomes harder and harder to break as the stakes get higher and higher.

It's a damn good point. Ryan, let's take a quick break.

All right.

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Welcome to Hollywood vs Reality. They do it, right? What does he do in the movies? Tell me if I'm doing this wrong, because I don't watch any of this shit. A little flick like that, right? Seems pretty cool. It is pretty fucking cool. Gotta silence it. In another lifetime, I did gun reviews for a living. Proprietary fucking magazines, supposedly the best engineering in the fucking world. When that breaks, you're fucked. And now we're bringing them back. It does look pretty fucking cool. I got it. I got to admit that. All right, Ryan, we're back from the break. I want to dive into ego.

Okay.

Ego is the enemy. Wrote a whole book on this.

Yeah.

Where do we start?

I mean, is there anyone that thinks ego is good? Like, is there anyone who's like, we need some bigger egos around here, that'll help?

I don't think so.

I like to think of ego as being the thing that gets between you and whatever it is that you wanna do. So in a way, like, I'm not saying like, oh, be sort of humble so low to the ground that you don't want anything, you don't try to do anything. Like, I actually think ego is the enemy of the ambition that you have. Like, whatever you're trying to do, Like, what you need is a sense of reality. You need self-awareness. You need a sense of connection. You need truth. Like, the ingredients to doing what you want to do are for the most part not delusion and grandiosity and selfishness. Like, it's the opposite of that. So when I say ego's the enemy, I'm not saying like, think you're a piece of shit. I'm saying just don't think you're God's gift to humanity. Like, confidence to me is somewhere in the middle between those two extremes. Um, and, uh, and yeah, chances are ego is causing the problems, not solving the problems, and personally or in your organization.

How do you keep yours in check? I mean, you're an extremely successful guy. Well, I mean, a lot of people that find success and then their ego just fucking explodes.

Yeah, I look, the first, first and foremost, admitting that you have one and that it is a problem is like a critical step. Like, like if I'm sitting here going like, let me tell you how to conquer your ego because I don't have one, like be real suspicious because, you know, I mean, my ego causes problems for me all the time. It's something I try to work on. It's something I try to work on and I'd be aware of and knowing that, yeah, like Success inflates the ego. Success, it not just inflates the ego, but it enables people around you to inflate the ego, right? Like in a way, you need to be more self-critical and aware the more successful you are for the reasons we were just talking about, which is the air is thinner and you get less, not only do you get less feedback, but you've got this really important piece of feedback that can be really, misleading, which is like you did something that wasn't supposed to be possible. You didn't listen to the critics and doubters and haters. And so do you take from that that you know better than everyone else?

Right? Like this happens to a lot of entrepreneurs. Like everyone said it was a bad idea. Everyone said it didn't work. How do you know when to listen in the future. Like, like when Elon Musk started, uh, SpaceX, which was his second company with the money that he made from his first company, like his friends had like a literal intervention, like, you cannot do this, this is a bad, bad idea, you will lose everything. I mean, it's going to go public and be a multi-trillion dollar company, right? So like, they were wrong. So how does he now— and by the way, this is also true for Tesla. That was supposedly a bad idea, right? Like, how does he— I think this is again a sort of larger life story that should help us understand this in our own lives. Like, how does he know in future instances not to just listen to himself, right? And so, you know, he's done some real dumb stuff too. And that's what ego does, is that sense of, I don't need to listen to you, I know better.

So with that, earlier we were chatting about trusting your gut instinct. Yeah, obviously Elon trusted his gut instinct when it came to SpaceX. It was— it is wildly successful, maybe the biggest company in the world.

Yeah.

And, you know, and so how do you differentiate what to take in from external influences and what gut instincts to trust?

Well, to me it comes down to like the story you tell yourself, right? So like, like when I went to my publisher and I was like, hey, I want to write a book about Stoic philosophy, they were not like cha-ching, you know? Like they were like, what? You know, that sounds like a horrible idea. Like literally they were like, huh? And I think I said this before, but I took less than half what I took for the book that became The Obstacle Is the Way. I took less than half what I got for Trust Me, I'm Lying. So like they thought it was gonna be less than 50%. Wow. Successful, as successful. So what's the lesson that I take from that? Like, I mean, it ended up, selling millions of copies and being this big thing. Like, do I take from that, like, those fucking idiots at my publisher don't know shit, right? Do I take from that, like, I'm a genius, that I can see around corners, that I, that, like, I know what the people want? Or do I take from this, like, hey, I had what I thought was a pretty good idea, and I could see how it wasn't an obvious home run to some other people.

And the reason it succeeded is because of, you know, I did the work, I was willing to roll the dice anyway. And also because, like, the downsides of being wrong were not that high either, right? Like, I took a risk and it paid off. It wasn't a certainty that I knew. It's, I took a risk and it paid off. So do I. So again, you could take, and we have 1,000 examples of this, but like you could take from this, hey, I'm a genius, I know better. That's, that's ego. Or you can go, hey, I took a risk and it paid off. That's to me confidence with some self-awareness in there. And so whatever story you tell yourself about why you are where you are, it, it doesn't change what happened. Like the event doesn't know that you're telling a story about it, but it does change how you make future decisions. Mm-hmm. Right? Like if you feel like you're anointed, if you feel like the rules don't apply, if you feel like you can defy gravity, you know, all these things make it really likely that in the future you're gonna overreach. And that tends to be what successful people do, right?

They tend to overreach. And so that's what I think you wanna take from, from, like, trust your gut, but trust the right part about it, not the delusional part of it.

Do you feel that you have ever overreached?

Yeah, I mean, I, I try to think mostly back around the calls that I made where I was super wrong. Like, I don't think about the fights I had with my publisher where I ended up being right. I think about the times where I insisted on getting my way, and in retrospect, they had a point, you know. I try to think about the, the times where, you know, I didn't listen to the feedback, um, and I would have saved myself a painful bump on the head had I done so. And I think that's healthy. I mean, like, Again, like, if you focus on all the things you know, you don't get any better. If you focus on what you don't know, you can get better. If you focus on where you fell short, you can make improvements. And if you focus on what you got right, you're just jerking yourself off.

How about humility?

I mean, I think humility is important. To me, confidence is— confidence is an awareness of strength and an awareness of weakness. Like, to me, the story of David and Goliath is at its core about the power of both of those things, right? David doesn't think, oh, I'm anointed by God, therefore I, of course, I can defeat Goliath, right? If he knew that he was, preordained to win, he would've just, you know, rushed heedlessly into battle and let God take care of it, right? Like the story, to me, the critical part in the story of David and Goliath is when David tries on the armor of the soldier, his brother's, and it's too big. And he goes, I can't do this. Like, this isn't gonna work. I'm, I'm— he's like, as a shepherd, he's just not able to operate as a traditional warrior. And that's when he turns to the sling, right? The sling is, hey, he's bigger than me, he's stronger than me, he's better trained than me. I don't have these tools in my toolkit, but I do have this thing, right? And so humility to me is a key element in matching what we're— what, what every battle, figurative and literal, is about, which is about matching strength against weakness.

Like, strength against strength is stupid. Um, it, it usually creates two losers even if there's one winner, right? Like, the— what a great general does what a great athlete does, what a great entrepreneur does, um, is match strength against weakness. Like, and, and by the way, also protects, hides your own weakness, right? Because that's where you don't want their strength to go against yours. So, so to me, this humility is really important. Like, knowing what you're not that good at, what you need to get better at. Um, is, uh, yeah, it's like a big part of it.

How do you keep yourself humble?

You know, the kids help, uh, spouse helps. Um, trying to do hard shit helps. Like, if you are only doing what you're really comfortable with and you're never in situations that you're outmatched, that you're that you're out of your depth in, you lose that feeling of like, oh shit, I gotta figure this out. Mm-hmm. And so like when I take on projects, one of the things I think about is like, is this something I've done before? And if it's something I've done before, like it's not that interesting to me. And if it's something where I'm like, oh, I'm gonna have to figure out a lot of different skills to be able to do this, And this can be in— I don't mean like you're reinventing the wheel every time. Like, I just mean like, what's the element of your game that you're working on? Like, if you go into the offseason and you're like, I want to practice getting better at what I'm really good at, I think that that is, you know, not just— not just the gains are going to be less than exciting, but like, it's a sort of a confirmation of ego.

But if you're like, hey, no, no, what I don't— what I'm not good at is this. What I could get better at is this. And that's what you're going to spend your time on. To me, that's— that, that helps with humility because you're waking up every day and it's fucking hard. It sucks. Um, and it's just— it's, uh, you can't— you can't feel you can't feel great about how you're doing when you're getting your ass kicked. And so how are you seeking out those experiences? I think that's really important.

What about with just amongst people? I mean, somebody as successful as yourself, you've reached millions of people with your books. Lots of people seek you out. They want to talk to you. They want to meet you. They want to get an autograph. They want to pick your brain. They want to—

they just want to be around.

Yeah.

You know, and, and that can really inflate your ego. So how do you navigate that? Especially how do you navigate that around your kids?

Yeah, yeah, it is like when you get recognized around your kids, it's weird. It's a weird thing. My kids, uh, like, they roll their eyes and, uh, they, uh, they— we were in Greece this summer and they started playing this game where they would— they, they wanted to see if they would see more stray cats than I would get recognized. And, uh, the fact that they saw like hundreds of more stray cats than I got recognized was like a thing they were just constantly shoving in my face, which I love. I love. Uh, and, um, you know, so yeah, there, there is, there is that. Uh, I think any— anything you do in public that has fans or, you know, sort of recognition attached to it can sort of puff you up. I have the benefit in what I do in that it's not mine. Like, I write about an ancient philosophy that has been around for 2,500 years. Like, the reason the books work is 90% the philosophy and 10% me. And I try to remind myself of that fact. Like I am a conduit for a thing that not only did I not invent and can't be credited with, I'm not even good at.

Like, my success in writing about Stoicism is very different than my individual journey through Stoic philosophy as a human being. And I try to remind myself of that.

Do you consider yourself a Stoic?

Yeah. I mean, if this is the philosophy that I am interested in, that I am trying to apply in my life, Do I call myself a Stoic? I mean, I would say I am an aspiring Stoic. Like, I would certainly not claim to have attained any kind of enlightenment or mastery of the stuff. Like, in fact, the reason that I'm so driven to write about it and talk about it is 'cause it's like, it's really hard and I really struggle with it. So I try to remind myself, that like, like when someone, someone comes to me and says like, hey, your books changed my life, they helped, you know, uh, or they say Stoicism changed my life, it got me through cancer, whatever it is, I go, yeah, it worked for me too. Like, like we're, we're on the same journey. Like what it's, what, what, what they think, um, is, has is my books is really like the philosophy that I am also a student of, if that makes sense.

It does make sense.

But it's like, you know, when, um, when they interview athletes like in the, in the locker room after like a big game and they're like, you know, all glory to God, I think they mean that and I think that's important. I also think that's like a really important professional adaptation. Like if LeBron James or Kobe Bryant or whoever is like, fuck yeah, that was all fucking me. You know, like I'm the greatest. That's bad. Like that's bad for future performance. Yeah, it's better. It's better to credit. And I don't just mean like from a public relations standpoint, like you have to mean it. Like if it's false modesty, it's a pro— it's— you might as well just own it. But if you're like, No, this was the team, this was the training, this is the tradition.

Like, you are, you are—

that is the, that is the right and the healthy way to think about it. First off, because it's true, and second, because it's not good for you to put that on and credit yourself for things that Why is it not good? Well, I think, as I said, first off, it's not, it's not good because it's not true, right? Like, everything is a team sport, right? And second, because it breeds complacency and entitlement. And, um, if it, if it's not a little scary to you and it's not a little hard and you're not, uh, you're not questioning your ability to do it, you're probably going in the opposite direction. Like, you're, you're, you're, um, it should be getting— it should always stay challenging and hard, or, or else it's like, you know, you're lifting weights. When it becomes easy, you grew, you grew the muscles, and you, you need to crank the thing up.

Makes sense. Let's move into— how do I word this— people that have experienced death or been close to death, or I guess not experienced death, but they've been around death. People that have killed, people that have seen war, people that have been around death a lot, and, and kind of knowing when to act, when to let things go. That kind of stuff. I mean, you have a lot to say on that.

I mean, I'd be, I'd be curious your opinion. I mean, when, when you experience how fragile life is, does it turn down the volume on stuff for you?

For a little bit, yeah.

Then it creeps back.

And then it creeps back.

Yeah.

I liked everything I was reading, and then I did, I compared it to myself and I was like, you know, a lot of this stuff bleeds back.

Yeah.

And then, and then you get, you know, in my life journey, in my previous life, it was, you know, there was constant, uh, you're humbled again. Yeah, you're humbled again. Uh, you're humbled again. Somebody died. Somebody died. We killed somebody. Somebody, you know, and, and so there's that constant reminder, and you live in that. Yeah, pretty regularly. Then I left, and I'm not around it anymore. And things that maybe don't matter or shouldn't matter, uh, they creep back in and they, they seem like a bigger deal than they are. And then I go into my revenge planning, or you know what I mean? And it just— it— I'm just being honest, it fucking creeps back in and it creeps back in faster than you would think.

Yeah, a friend of mine is in martial arts was telling me that it's like sweeping the floor. You don't sweep it once and it's clean forever. It's a constant process of sweeping. And I think ego is that way. And I think, uh, like, the urgency of life is another one. Like, you go to the doctor and they're like, oh, I need to check that out. There's that moment where you're like, oh shit, is this it? You know, is this— did it just get serious? Or, you know, you were talking to a friend on Friday and then you find out over the weekend they died. Or, um, you know, natural disaster, you know, whatever, anything that happens, and, and suddenly you're like, oh, I forgot we're mortal.

Yeah.

Um, that's the Stoic practice, is memento mori, like remember you are mortal. Um, but it, it, it has to be an active meditation because like we all know objectively that we're all going to die. Like every, every person who's ever lived has, has, has eventually died. There's, there's no way out of life. And we know that although on average, you know, this is about how long we have, people die before they should all the time. The healthiest people in the world drop dead of a heart attack. The greatest people in the world get murdered for the money in their wallet. Obviously, wars and natural disasters, it happens. But then you get a little soft, a little entitled, you drift away from that urgency. And so, yeah, to me it's an active process of reminding yourself that, yeah, tomorrow is not certain. The future is not yours. One of the, I think, the most powerful ideas from the Stoics, this comes from Seneca, you know, he says it's wrong to think of death as something that happens in the future, like that death is something we're moving towards. He says actually death is behind us. He says like, um, the time that passes belongs to death.

So instead of thinking like you live 80 years, he says like you've died however many years you're currently old. So like, like I'm gonna— I turn, uh, 38 next— 38, no, 39 next month. I don't remember. Um, but anyways, like my birthday I should look back and go, this is how many years I have died. What do I have to show for that? Not how many years do I have left, but what have I— what do I have to show for the time? Because, because how we spend our time is how we spend our life, right? And, and so the idea of going like, hey, oh, you know, I'm— I don't like this, but I'm gonna do it until my kids grow up, or I'm gonna do it you know, for a couple more years. I'm gonna do it till things settle down. Like, you know, we, we tell ourselves, like, we make these assumptions about the future, and really the only thing that's certain is, is now, the thing you're, you're paying for with your life right now. And so that I do try to remind myself of that, that like, um, we don't— the choices we're making about our time right now are the choices that matter.

The idea of working something you don't like, deferring something you don't like because what you really want to do is play golf in your 70s is naive and entitled. And so, by the way, is just the basic procrastination of like, you know what, I think I'm gonna start that project next week. Like, if you're gonna do it, you should do it and you should start right now. That to me is what you take out of the Memento Mori practice.

Yeah, I really struggle with this. And just in my personal experience, every time that I have been around death, thought I was going to die, there's only one thing that goes through your mind, and that is that's your family. That's it. That's the— it's not all your shit.

Yeah.

It's not all your accomplishments. It's not what you've done at work. It's not any of that. It's not how much fucking money. The only thing is like, shit, you know, who's going to watch out for my family?

Yeah.

When I'm out of here. And, and then, you know, that, that creates the fight, you know, to stay alive. But what you're, what you're talking about, I, and I still struggle with this no matter how many times I thought I was going to die or been around it or been close to it. I, it's been— I've had that constant reminder, like, none of this shit matters. Yeah, the only thing that matters in my head is my family. And but then there's the preparation, you know, I have to hit this financial benchmark, I have to hit this, I have to hit all these accomplishments or, or goals or whatever it may be to make the future of, of my life, my wife's life, my kid's life hopefully easier in the future, which takes away from living in the now because it's all planning, right?

Well, even more insidious, like, at some point you would give literally all of it back for 5 more minutes of time with them, right? And then here you are fucking doomscrolling on Twitter with the 5 minutes that you have for sure right now. Like, you're gonna look back and wish that you could have more of this. And what are you doing with it right now? You're wasting it. And that to me is what I take from it, is like, I have the thing that in the future will be priceless and unattainable, and I'm so frivolous with it. And I say yes to things 'cause I don't wanna be rude to someone. I get distracted because something's happening in the world. I, you know, I get overwhelmed and I'm like, I'm gonna take a break. You know, like, and you experience it in little, like already, like if you have little kids, you're just like, dude, like a year ago, like that's gone, right? Like these, Periods are so fleeting and so short. And in the moment, you want it. You want, like, the next thing. You want to get out of it. I can't wait till they walk.

I can't wait till they, you know, talk. I can't wait till they drive, whatever it is. And then actually, when those moments come, all you wish for is more of what you wished away in the moment because you were entitled or short-tempered or frustrated or whatever.

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How do you reset?

Do you find yourself going down those rabbit holes too?

Yeah, of course. I mean, I try, I try to— the good news about the present moment is that you're always getting another one. Until the moment that you don't. And so how, to me, how quickly can you get like, shit, I'm throwing the phone down. Like, I'm stopping right now. Not like tomorrow I'll do better, but like I'm stopping right now. It's like, how fast can you get back to center is to me like the key skill, both as a parent and as a person in this crazy modern world. Um, but you know, today was rough. Okay, how do you do better tomorrow? And how do you stop whatever the direction you're going in that you, you know, you shouldn't be going in? And how quickly you can do that.

What are your indications? Do they come from you? Do they come from your wife, your kids?

Yeah, I mean, I feel like parenting is a lot of, uh, after they go to bed, you're like Man, what are we doing? Why did it go this way? You know, it's that sort of debrief at night. To me, that's, you know, and it's very rarely, man, we crushed it today. Like, it's usually like, why did we try to squeeze one more thing in? You know, why did I? I remember I was putting my son down for bed the other night and, you know, First off, can I have a little more iPad time? Then I gotta brush my teeth. Oh no, now I gotta go to the bathroom again. Or, oh no, no, I need water. Oh, I'm hungry, even though I had dinner twice. You know, all the stuff that he's making up for, uh, you know, not going to bed. And, uh, then I finally— he's like, all right, we go in his room, and I'm like, all right, let's get in bed. And he's like, no, no, I'm sleeping on the floor. And I go, what? You're not sleeping on the floor. Like, and then we just got in this huge, you know, What do you mean?

You never said I couldn't sleep on the floor. We get this whole fucking argument about why I couldn't sleep on the floor. And then I was finally like, I was like, why do I have an opinion about this? You know, like, sleep on the floor. I don't care. I realized, like, I think in the moment it was like I didn't want him to sleep on the floor because here's what I knew would happen. He would sleep on the floor until like the middle of the night and then wake up and then he'd come in our room, you know? And it's like, I wanted sleep, right? I was extrapolating what this means, what, you know, like Instead of like going like, I don't care where you fall asleep, I was thinking about what it means if you sleep here or there, right? And so anyways, finally I'm like, I just realized I'd gotten down, that I was in a battle of wills that like I had the power to end right then by saying, sleep wherever you want, you know? If you wanna sleep on this teddy bear on the floor, like knock yourself out. So anyways, he lays down, And just when I think he's fallen asleep and I go to leave, he goes, I'm ready to sleep in my bed now.

And I go, all right, let's go. And he walks in and he falls asleep in his bed. And it was such an illustrative one for me because it was like— it's like, I know when it started. It started when we walked into his room and he said, I wanted to sleep on the floor. And I said no. And then it ended with him realizing that he didn't want to sleep on the floor and, uh, he would rather sleep in his bed. And that whole argument, you know, where I argued one thing and then I realized I was wrong and then I changed, like, that whole thing in the middle, it just didn't fucking need to happen, you know? Like, the whole— like, it, it would have worked itself out had I been, uh, a little more go with the flow about something. And I think I— what I took from that, what I've— as a parent, is just like, I need, I need to be more in the— like, does this thing actually matter? Like, why am I thinking that this matters? And I'm thinking that it matters because I'm thinking about what it means, as opposed to that it means nothing, right?

And that, that I could save us both a lot of— like, I could save us both a lot of trouble. And in fact, like, not only did it work itself out, but it worked itself out except we also had a big argument in the middle, which has a, a, has a, has a cost to it, right? And so look, I'm not saying you do everything your kids want and you let— you know, it's— you got King Baby walking around. But most of this conflict— like, when I think about the things I had conflict with, with my parents, how many of those in retrospect were significant in any way, you know? And how many of those things are they glad that they went to the mattresses on? And I'm trying to get better at that.

You're saying pick your battles.

Totally. And, and, and by pick your battles, I mean avoid 99.9% of the battles because they don't fucking matter.

So how do you guide them then? I mean, now we're moving into fatherhood.

Yeah.

How do you— I'm just curious, how do you guide them without confrontation, without discipline, disciplining them?

Yeah, I mean, yeah, of course that's the challenge is like You're not creating this fantasy world where they get to do whatever they want whenever they want it. But at the same time, like, like, again, why do I care whether you sleep on the floor or their bed? There's no lesson in here. What it— what there actually is is me wondering about the consequences of this for me, and two, um, my desire for control, right? Like, you want to do this and I want you to do this, and why am I going to let 6-year-old win, you know, like most— so like in a way you think like, oh, I'm giving them discipline, I'm giving them structure, it's very helpful. Actually, you're just showing them like authority is arbitrary and pointless and, you know, should be fought against. It ever— like you're actually sending the exact opposite lesson you want. And again, I'm saying this all as someone who constantly struggles with this, so I'm not saying this is something I'm good at. It's precisely the opposite. But, um, I mean, look, you teach your kids by example, and you teach your— you, you teach your kids often, uh, in the moments when they are open to being taught because they've experienced some kind of consequence or, uh, uh, for, for a choice, or they have there is an opening because of something that's happened, uh, for you to actually insert that thing, that bit of wisdom or experience or lesson or whatever.

That's kind of how I think about it.

Okay. I mean, you wrote a whole book on Stoic fatherhood, correct?

Well, I did a book. I did a book called The Daily Dad, which is just sort of, yeah, classical or ancient lessons, like one, one a day. I think the problem with parenting books is like You're just supposed to read this book and then just be good? Like, I'm supposed to read about, when my kid is 13 months, I'm reading about how you teach things to a 13-year-old? Like, I'm not gonna remember any of this. So the idea of the Daily Dad is it's an email too. The Daily Dad email is just one thought a day. It's, I think to me, parenting is like a series of values and lessons that you've gotta be reminded of over and over and over again. And that, that's kind of what I've tried to do with it.

What are some of the most important ones that stick out to you?

Um, yeah, I think that the, the most important one, I think, is just how fast this is all going. And that you, uh, every time I, I cut my kids' fingernails or take them to get a haircut, I go like, that's that much life right there. That's that much of the brief window that they live in my house, right? That we get to do things together. And I try to be always aware, just as like Memento Mori is about your own mortality, realizing that like, I don't have a 2-year-old anymore. My 3-year-old is dead and gone. My 4-year-old is dead and gone. You are cycling through those ages and they will never be that thing again. To me, that's like one of the ultimate parenting lessons. The other one, my wife and I were related to that, was like, we were like, do we want to? There was like some kids' concert or something we were thinking about going and we're like, oh, we gotta get in the car. It's like a 30-minute drive. Are they gonna appreciate it? And it was just like, how many more times are they gonna want to do this?

You know? Probably not that many more. Like, at some point there's the last time. And are we going to be glad that we stayed at home and didn't do the thing? Are we going to be glad that we did the thing? So realizing that you only get so many shots at these things, I think, is a big one. That you are the voice that's going to be in their head. And what is that voice like? Is it a negative voice? Is it a positive voice? Bruce Springsteen talked about how, um, we're going to be either ancestors or ghosts to our children. Like, an ancestor guides and a ghost haunts. And what, what kind of example are you gonna set?

Yeah, I never thought of it like that.

And it's not just like what you say, but also like, is Dad working on his shit? Is Mom working on her shit? Or are they just foisting that stuff on you? And so, like, thinking about getting serious about the stuff that you know you need to address, you know you need to work on, I think that's one. And then related to that, I think, like, I have, uh, I've never lost my temper at my kids and then afterward been like, I'm so glad I did that.

Yeah.

Um, one, I have, like, on my phone, you know, it cycles through, like, pictures of my kids, like, as my home screen. And one of the things I'm always struck by is like how little they were. Like, I was real fucking pissed at a very small person. Like, like, it doesn't age well. Like, the things you get upset about, the things that you thought were a big deal, as they get older and you get a little better at this parenting thing, I think that the disparity of them and you becomes more obvious. And, um, I'm like, why did I— like, like, like, what do I give a shit about the backseat of the car so much for, you know? Or like, you know, you walk in and he's drawn on the wall, or, you know, uh, broke something, you know. What— where's, where's the car that my parents were really concerned about me spilling fucking my McDonald's ketchup on? Like, it's in a— it's in a fucking cube somewhere. Yeah, like, it doesn't— like, it did not ultimately affect the resale value of said car. It did not teach me any lessons about cleanliness. Like, it, it was just like a stupid argument that we had, right?

Like, and I, I try to think about that. Again, not good at it, but I try to go like, where will this thing be in the future? Am I going to care about it?

You don't put importance on anything.

So yeah, yeah. Or I, I try to get better at not— the human or the thing? What do I care more about? You know, the, the marriage advice is like Do you want to be right? You want to be married? You know, um, do you, do you want to have a good relationship with your kids, or do you want to get your way all the time?

How do you know if you're— I mean, that's just a really good way to put it— if you're a positive or a negative in your, in your kid's mind? How do you gauge that?

Um, to me, I think It comes down to, to like, like, no, no parent is perfect. Every, every, every therapy session ultimately ends up in all the ways that your parents could have done better or whatever, right? But like, you know, people say like, oh, my parents did the best they could. I'm not sure that's always true. And so like, are you actually doing your best? Like, that's to me the question is like Like, I go, you know, I'm, I'm doing my best. And I go, am I? Because I feel like I try a lot harder at other stuff. Like, I'm not saying parenting is easy, but I feel like I do a lot more work evaluating myself professionally. I bring in a lot more help professionally. I, I measure myself better professionally. And then a lot of times as a parent, I'm just winging it. And then, and then, then I wanna— I want them to let me off the hook and go, Dad was doing his best. Like, I'm not sure that's true. And so that, that does kind of push me to try to do better.

Damn, it's like me. I'm like that.

Yeah, because look, and I think culturally, for, for men especially, right, like your job was where you were supposed to be like your best, where you prove yourself. And then parenting was like an afterthought. And, um, the expectations were— you know that expression, uh, the soft bigotry of low expectations? That, that's basically dudes for all of human history when it comes to parenting. And like, I don't know, I want to do better than that.

What are the— I mean, what are the steps that you're taking, that you're thinking about taking that create a better balance?

Yeah. I mean, to me, a big one is like, okay, so you're really good at what you do. You're successful at it. Uh, and then, and then you think that that somehow like exempts you from having to do shit at home, right? Like, um, like obviously, look, managing your time and delegating where you can, but you're like, why am I assuming that like my wife should make the school lunches? Or there's this— like, they did this interesting study of, like, schools where, like, they needed something at home. Like, like, there's some problem at the school, right? And the, the, the receptionist or the principal or whatever had to call the parent. Like, what percentage of the time do they call the dad?

Probably a very small percentage.

And there, there's, there's the assumption of the person making the call And then there's also the reality of like the family, like, and like I've worked really hard and my wife and I, like whenever we hire like an assistant or we, we're like, like we're like, there's no, we're both the default parent. Like it's not like call her if there's anything important and then call Ryan if you can't reach her, you know? Like I wanna, I wanna make this a thing that I value. And that, like, like I heard someone say, like, your kids are not a distraction from your work, they are your work. And that's easy to say, but like, do your— what does your calendar say? You know, what is your division of household labor say? Like, your kid has a birthday. Are you just showing up at the birthday party, or did you make planning decisions? You know, could you make purchase decisions? Did you— did it catch you off guard that it was there? But like, like, there's just, there's just a, uh, an assumption. I think it's— look, it's obviously better than it's ever been before, but there is like an assumption that like, that's not— like, the term for this is emotional labor.

That's not emotional labor that the father should have to do unless they're like a single parent or, you know, whatever. Um, and, uh, I'm not saying it came easy and I'm not saying it came voluntarily. I'm just saying like in my marriage and in my family, my wife and I have tried to not do that. And it's been like I've had to learn how to do a bunch of things that I would not— I would not normally be inclined to do, uh, or be good at, I've had to figure out how to do.

Man, it's, it's just a— man, it's such a dichotomy, right? I mean, I think about this all the time. I've talked about this several times on the show. I mean, my wife and I have like this little bitty fucking hunt cabin that's— it is like, looks like you could blow on it, fall over. Yeah, you know, it's, it's, it's all one room, you know, the kitchen, the bathroom, it's all one room.

Yeah.

And, uh, and, and before my kids were born, we would spend weekends down there and just to— we live out in the— we need— yeah, we live out in the woods. You go down there, you're really out in the woods. And that's the— some of the happiest times I've had with my wife is down there. Zero— there's no cell reception, there's no internet, there's nothing. And, um, and I keep coming back to this, which I love doing this, but I'm happier right there. No distractions. I'm in the moment.

Sure.

And, you know, and now that I'm close to being able to just— I could do that. I could get rid— I could sell.

Sure.

The studio. I could do— I could get rid of all of this, sell it. It'd be totally fine financially and actually live that life where I'm 100% dedicated to my family.

Yeah.

100% of the time.

Yeah.

And knowing that I would probably be happier.

Yeah.

I 99% sure I would be a happier person, you know, if I, if I put all the— even though I love doing this, you know, put all the world's distractions and it just away from my life, but I still fucking come back to this. Yeah, because I love it. And, and I also think about, you know, well, what would it be better— would it, would it, would it realistically, would it be better for me to be there 100% of the time for my for my wife and my two kids? And what kind of example is that setting for my son? Because that's not how society is set up.

Yeah, I think it's an interesting question. Is it better for them? Is it right?

It's, it's better for them right now. Is it better for their future? Yeah, because they're, they're, they're going to hit a point where they're going to have to provide for their family. Uh, it's unattractive. I personally think it's unattractive for a woman to whether he is a wealthy, financially wealthy man or not, a trust fund baby, you know, I don't think women— I don't think that's a real attraction.

Sure.

You know?

Yeah.

To find in a partner.

Sure.

You know, and so if he doesn't see me providing for the family and doing things that, in my opinion, men should be doing as the leader of the household, then what happens to him when, when he comes of age to find a wife and have kids and provide? Well, don't you ever have that example? Then what is that going to lead to? And he may not ever find somebody if he doesn't— if he doesn't get that example.

I remember a couple of weeks into the pandemic, my wife was like, please never be home this much ever again, you know? And like, obviously I had to do some work on like being like, okay, I have— I have to be— I have to become a more stable, like, chill person because this, this is it. This is currently operating in a way that's only good in small doses, right? That wasn't good. At the same time, like, to take the energy and the drives and the competence and the mastery, all the stuff that you have and be like, I'm gonna put all this at home, you know. I think that's also how you get fucking stage parents and, um, you know, uh, sports parents.

Like, what are stage parents?

I just mean like the parents that make all facets of their existence their family, right? And then all of a sudden you're just channeling that energy. Yeah, at home. Like, it's— there's an intensity and a and, uh, an energy that has to have a release valve. And I think work and impact, like, that shouldn't all be on your family. Like, there, there's a re— we're, we're meant to go, to go out and do things and to figure things out. And it's like, so you're just gonna drive him to school and then play golf all day? Like, I'm not sure that's— that's not thriving as a human being either, or setting a good example either. So there's a tension. But yeah, I think one of the things that bothers me, and, and I think we all delude ourselves with it, is we go like, I do this all for my family. It's like, no, you don't. You stop needing to do this for your family a long time ago. This is about you, right? And, um, and That's not to say it's not about them at all, but like, you're a billionaire, dude. Like, you're not doing this for anybody.

You're doing this because there's never enough for you. And so, um, it can be very easy to take something selfish and make it seem like it's selfless, justify it. Yeah. And so understanding the tension between those two things And like, what I've tried to— I, I've tried to say and work on a way that I can be really good at what I do and keep it within some reasonable hours, boundaries, and, and systems. Like, I— to me, like, what I'm working on, like, my— I'm not trying to be the— sell the most books in the world, have the most impact in the world, or be the most famous or any of— I'm trying to be really good at what I do and be a really good parent. And that in a way, that's actually a more difficult needle to thread than just being all in one or all in the other. And I think it's important that we understand that that's possible to do. Like the athletes that I admire or the entrepreneurs that I admire or the leaders that I admire, are not the maniacs, right? It's the ones who seem to be reasonably well-adjusted human beings also, right?

Like, sometimes you read about these, like, this is my daily routine, this is my system, this is how so-and-so prepares in the off-season. And you're like, well, I'm sure that's all really easy to do if you don't fucking see your family.

Yeah.

You know? Like, if you're a piece of shit, that's easier.

Yeah.

It's, it's can you, can you be in great shape? Can you do what you do? Can you perform at a high level and do school drop-off or I don't know, be involved and be present when you're around? You know, like, can, can you like, that's the challenge for me. Like, it used to be like when I was working on a book, I was just an all-consuming thing. I don't just mean the hours, I just mean like I couldn't turn it off. And now I try to judge the success on a book on like how, how, how not disruptive it is.

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How do you—

I mean, what are your indicators for you that tell you if you're leaning? Yeah, talking to you, I doubt you lean too far into family. It seems like you probably lean too far into work.

Yes.

You know, and so what are your indicators that let you know? Is it a personal guilt? Is it a— is it some— the way your kids are acting or communicating to you? Is it your wife? What is— what is— what are your indicators?

Yeah, I mean, look, just practically, I try to measure, like, the stuff that I do or I say yes to. I measure it in bedtimes. Like, how many bedtimes am I going to miss for this thing? And like, one is a lot, two is usually too many, right? So I try to— I try to measure it in bedtimes. So that's like— that's kind of my north star. Like, how Physically, is this taking me away, yes or no? And that's kind of how I judge like the stuff that comes my way. That being said, that can be a way of fooling yourself, which is like you're there, but you're not really there. So I try to think about like, hey, how is my emotional state, my focus, like am I the reason that this is all dysregulated or am I the calming presence, right? And I think too often, like, I'm— it's like, I came home amped, I came home worked up, I'm stressed, I'm distracted. And you can, like, I think you can just feel the energy in the family dynamic. And, um, I want to be the solution, not the problem. And I think I know I'm, I'm not taking care of the things I need to be taken care of, and I'm not doing what I'm supposed to be doing when I am I'm the problem, you know?

Like, like, if the 3-year-old is upset because they're a 3-year-old, great. If the 3-year-old is upset because you snapped at them because you were trying to play with them and check your phone at the same time, you're the problem. And so I try to think about that, like, how am I fitting into this system, this, this sort of wavelength, as opposed to I want to make it all about me.

Makes a lot of sense. Makes a lot of sense.

And then you should have a spouse in a family dynamic, co-parent, whatever it is for you, where they're like, dude, what was that? You know, like, like, I think my wife and I talk a lot about like, like, let's back each other up in the moment, you know? Um, let's not throw each other under the bus in front of the kids, but like afterwards, like, yo, you can't do that. Like, you know you can't do that. You saw, you saw when you made that choice, right? It goes both directions. But like, I think if, if, um, if, if you're not making each other better as parents, you're not, you're not doing your job.

Yeah.

Yeah.

You know Steve Rinella's book?

Yeah.

About outdoor kids and then inside world. I mean, there's so many studies that talk about, you know, the more kids are outside, the, the, the— I mean, the percentage of them having depression decreases dramatically. I mean, less screen time, depression decreases dramatically. You raising your kids on a farm?

Yeah, correct. My son's— my youngest is in first grade, and when he started in August, it was the first time he ever sat at a desk. Because he went— he did kindergarten and pre-K for several years at an outdoor school. Like, they would go, there was no buildings, and they did it outside, rain or shine. You know, they ate their lunch around a campfire, and they did all the stuff outside.

That's awesome.

And it was incredible.

And that kind of education called—

I think it's just called a— it's like a nature school or an outdoor school. I guarantee you there's one around here. And it was incredible. And, you know, um, that, that was a big, big choice for us. And then, um, you know, we— like, one of our big things is like, okay, sure, screens are— maybe, maybe better parents than us could exist in a screen-free household. That we didn't— that ship has sailed. But like, we try to use them to— like, how is that an entry point into a world that we, we are, by nature of where we are financially and the freedom we have, like, we— I can show you that world, right? Like, my, my boys got really into this podcast called Greeking Out, um, which is— it's all about the Greek myths. It's amazing, uh, it's like 10 seasons listen to every episode multiple times. And so like, we went on a road trip across Greece, going to Rome this year. Like, if you get— if they get interested in a thing, like, because they watch a video about it, they hear about it, like, let's go experience that thing in real life.

Um, so to me, like, one of the most important skills you can have in life is, is first curiosity, but then second the ability to take that curiosity to its natural conclusion, right? Like if you're interested in something or you don't know about something, do you have the skills to go figure it out? You know, like there are books about that, there are videos about that, there are podcasts about that, there are places we can go, there are experts about this thing, there's AI, right? Like how, how you, So to, like, to me, I try to see the screen as an entry point into the enormity of the world. And then it's like the algorithm is exposing themselves to stuff. And then because they're interested in it, like my job as a parent is to take them down that rabbit hole.

Okay.

And so that's kind of how we think about like learning and doing stuff.

So I like that.

Like, oh, we're going on this road trip now, I guess. Like, you know, Or, and I'm showing them stuff, right? Well, it's like I showed my son this like Saturday Night Live video and he thought it was hilarious. And then, you know, it's like, oh, you wanna take an improv class now? Done. You know, or, oh, did you actually know like Lorne Michaels' papers are at a museum in Austin? Let's go do that. So like that idea of like they have that flicker of interest or, um, uh, awareness of something, how do you, how do you take them down that rabbit hole?

So they show interest and you immediately act on it?

Yeah, yeah. And, and like, it's not heavy-handed, but it's like, oh, there's so much more of that you don't even know. And that's like, that gets me excited, right? Because like, sometimes it's something I know a lot about and I get to show you all the things that I know about it. And that I love about it. And then sometimes it's something I know nothing about, and we get to go learn about that together.

Do you introduce things to them as well?

Yeah, yeah.

You're—

it's like you're always like, um, what about this? What about that? And you know, you don't have a great hit rate, but when you— when, when it, when it, um, when it lights them up, that's like the best. Like music, movies, um, Yeah, nice.

Let's talk. I'm dying to talk about this.

All right, Churchill.

Yeah.

Okay.

I didn't grow up with money.

Yeah.

Was never around it, you know. And, uh, now I find myself making a pretty decent amount.

Yeah.

And I don't know where to look to, you know. How do you raise kids with that? Keep them humble, keep them from being entitled, keep them from idolizing shit. Yes, fucking cars, watches, whatever, you know, the— yeah, luxury items, or, you know, how do you do it?

I don't know.

And, and you don't know whether you see all these people that have grown up with it And a lot of times I don't like the way they turn out, you know. I, I don't wish that for my kids, I'll say that.

And you don't know if you're doing a good job until it's like too late. Yeah. No, I think, I think it's the thing that keeps parents up at night. Um, I remember I was talking to Matthew McConaughey one time and he said, you know, there were a lot of things when he was a kid where it was like, we can't But then you find yourself in a position as a parent that's very different, and it's like, we're not going to— like, we don't do that. That, that challenge— like, in a way, it's not easier because it's hard to not have enough, but it takes the choice out of things, right? Like, yeah. Um, You know, and I think, I think not to idealize the past, but like, there used to be— society was the, the, the income inequality was less. Like, we've never existed with this level of income inequality in this sort of stratified world, right, where it's like Okay, now it used to be there was first class and economy on an airplane. Now not only are these different levels on an airplane, but there's like private. And the people who are flying private are living in a very different world than the people who are not.

And how do you, how do you stay in reality, I think, is like the first, the first challenge. Um, especially as, you know, people get to levels where, you know, it's, it's inconsequential to them, like what this costs or that costs. Um, you, you have to create some artificial boundaries and rules, I think. Um, I just, I don't know.

It's fucking tough. It is, because they have to— like, you could starve them from all of that. Yeah, as a parent. And you can, you can start, but then on the other hand, eventually they're going to be in it. And if they don't know how to act and when they're around it, then I also think you're doing them a disservice. And so they really need to know how to operate in both worlds. In my opinion. And how do you get them to operate in both worlds without becoming a self-entitled, selfish piece of shit? I mean, for lack of a better word.

Look, it's a timeless— it's a timeless challenge. Plutarch, one of the great biographers of antiquity, was talking about how parents will spend a lot of time on their will, trying to create an estate. Who's going to manage the estate? Who's going to be the guardians? How much money do they get? You know, spend a lot of time thinking about that and not enough time thinking about how do I raise a person with enough character that like they can handle it, right? Like instead of being like, oh, we're creating a trust fund and the trust fund gives them this much per year, which is just enough and not too many. It's like you could also just raise, spend your time trying to raise a child who has good values and a good work ethic and doesn't derive their value from luxury goods, right? Um, so I think it's the— it's a challenge. Certainly, again, nothing close to the challenge of being a single mother on food stamps trying to raise 3 kids or whatever, but it comes with its own challenges. And, um, Ultimately, I think we have to model it, and then I think we have to— like, the most valuable gift you can give your kid is not, you know, a huge estate.

It's like the ability to, uh, like, have the thing that lights them up, like, that they like doing. That like they want to spend their life doing. Like Robert Greene, my mentor, he calls this your life's task. What is your life's task? Like, what were you put here to do? And I think our job as parents is to help our kids find that thing, to create an environment where they can find that thing and be supported and loved in pursuing that thing. You know, it's not to make them a doctor or a lawyer or to inherit the family business. It's to find the thing that if they didn't do, not only would they be unhappy, but the world would be worse off for them not doing it.

Mm-hmm. I mean, I want to say something too, just for the audience. I mean, I don't want to sound like a couple of fucking elitists.

Yeah.

You know, sitting up here talking about this, but this is— this is because we're not even talking about what we have, what we don't have. We're just— anybody who finds himself in a position that they are doing better than, than their parents did. This applies to them, whether you do something, you know what I mean?

Look, your average American has a, a level of choice and privilege that a struggling family almost anywhere else in the world is not having to think about. So, so this is privilege, but in a, in a way that we're all privileged and there's just different degrees of it. But yeah, how do you, how do you, how do you raise a kid who is resilient, who is in like— Stoicism to me is about being in control of yourself, being master of yourself. And that's what we're trying— like, you're trying to raise kids who can go through life, uh, and, and are not going to be, as we said, don't say ew a lot, don't throw in the towel a lot, don't expect other people to solve their problems for them. Um, how do you raise self-sufficient resilient kids. That's the challenge of our time. And yet it's also the most timeless challenge. There is— every parent for all time has had to deal with that in some form or another. And I think, um, I, I don't think there's one thing you do. I think it's a, it's a, it's a handful of things.

Do you think it's how you act? I mean, the things that I've learned— and my kids are very young My oldest is, uh, close to 5. But, you know, I think, I think it is— I really am starting to think it's the only thing that really matters is the example that you set for them.

Yeah.

So if you idolize your shit, they're going to idolize their shit. If you get pissed because they fucking scratch your car, break a window, whatever, break a vase, anything, you know, and you, you overreact and idolize the thing, that's going to be passed on.

Yeah.

Same with people, you know, they're going to look to see how you treat people, all people.

Yeah.

Not people you look up to and people that you think that you're above. All people, and they're going to take that in. And hopefully, you know, the financial aspect, it doesn't have any relevance if you lead by example.

Yeah, like they say, your kids— kids don't always listen, but they're always watching. And like a way to think about it is like, let's say you never gave them a single piece of advice. Like you never told your kids, do this, don't do that, this is important, that's not important, this is what we believe, these are our values. What do you think they would deduce about what you think about those things from the life that you lead? Like, like, if you were tried in court, would you be convicted of those beliefs from your actions? I think that's Like, you know, I think about this, it's like, okay, so I write about Stoicism, but if I didn't, would my kids say that that's what I believe in or care about? Would that be how they would describe me? You know, and that, like, that's the message that ultimately matters. Like, what are you saying with your deeds, not your words? And you say this matters and this doesn't matter. And then, you know, your, your, your decisions tell a very different story. I like to say, like, you know, your calendar doesn't lie.

Yeah.

And neither, neither ultimately does, does your, you know, your behavior at home.

Do you ever ask your kids for input on how you're doing?

Oh, like what can I do better? Yeah, all the time.

Do you really?

Yeah.

What do they say?

They're usually like, can I— you should give us our iPads more, stuff like that. Um, I, I think it's, it's a lot to ask them to be able to— I think when they're, they're older, they're going to be better at being able to verbalize like what what they need more of and what they need less of. But I do try to think like, hey, like, why isn't this working? You know, I try to like, why is it— if this isn't having the effect that I want it to have, I need to do something differently instead of insisting over and over again that this is how it should go. This is, you know, this is what I think. But I don't know, it's, it's a, it's a, it's a constant fucking challenge.

Yeah.

And one of, one of the, um, one of the things, uh, I heard someone say that was helpful to me is like, like, uh, the bad parents aren't thinking about whether they're doing a good job or not, you know. So the fact that it is a challenge and that you are thinking about it and that you're you know, how are we doing here? What could we do better? I'm worried about this. Like, that's not— that already puts you in, in somewhat elite company.

You're a better parent by— yeah, you're in the better parent category.

Yeah, yeah, yeah. Well, look, a lot of people have kids. Not everyone's a parent.

Yeah.

And the decision to be like, hey, I'm going to, I'm going to take this thing seriously. I'm gonna— it's not this side hustle that I have, it's like my main thing. It's the main reason I'm here. Um, and, uh, I'm going to— I'm going to work at this like I work at anything else, which means I'm going to take it seriously, which means I'm going to ask for advice, which means I'm going to actually look at how it's going and the results. Um, and then I'm going to be willing to change and try, try it differently. I'm not just gonna go, well, my parents did it this way. Or, well, this feels right to me, but actually be willing to change and take feedback is not just change and take feedback. I think, I think also apologize. Like, there are things that 30 years later, if my parents apologized for, it would mean a lot to me, right? Like, I don't know about you, but like, if my parents were like, hey, you know what? When you were a teenager, you really clearly needed this, and we didn't do that for you. And I bet that was hard.

And like, we thought about it more, and like, we wish we'd done it differently. I'd be like, oh my God, right? So it's never too late, right, to apologize. How, how quickly can you do it now though? Like, like, can I go, hey, like the next day, hey, I don't know why I picked this fight with you about you wanting to sleep on the floor. It doesn't matter to me. I just love that you still let me put you down. And picking a fight was not how I wanted it to go, but I did. And I don't want to do that. I'm sorry. I mean, I don't know about you, but I didn't get apologized to much when I was a kid. And maybe some people think that's weak or soft or whatever. To me, I'm trying to get better, and I do it. I'm not going to get better if I'm not taking accountability and responsibility for when I don't do it the way that I want to do it.

I do it, especially about the phone. Yeah, I feel so fucking guilty, and I keep doing it over and over and over again. Yeah, but I probably, you know, I'm like, I do, I just, I have to do it. Yeah, because I think that once again, a lead by example, because it also teaches them like they need to be able to do that too.

Or just to see you struggle with like, you're like, hey, this is a thing I have to use, but I use it way more than I have to and I want to use it less. So here's where I want to be and here's where I am and here's your dad trying to get there. Um, to me, that's a much more relatable, a much more inspiring, and ultimately much more practical perception of your parents than mom and dad are perfect, their word is law. Like, because kids know that's not true. They sense the bullshit.

Yeah.

And they resent it, and it undermines— it undermines their connection and their belief in you. And so Yeah, I try to, I try to, to own that shit when I can. And I try to be, I try to be clear about the stuff that I'm working on and the stuff that I'm trying to get better at.

Yeah. Yeah. You know, I'm doing a— I got so much out of my first psychedelics ibogaine treatment. I'm doing it again in the, in the, in the foreseeable future. And what I'm really hoping I get out of it is some kind of perspective of what my kids think of me.

Oh, interesting.

I really want to see what I look like through their lens.

Yeah.

And that's probably going to be a hard thing to see. But, um, yeah, I, uh, I just want to— I want to improve and, uh I really want to see that.

I saw this video of, uh, this billionaire, and someone was like, and what's it like to have a billion dollars, or what's it like to be rich? And he was like, rich isn't having a billion dollars. Rich is having kids who want to come home for the holidays. Yeah, I think it's, it's, it's really important that you sort of define what success is, right? Like, people go, oh, you only get 18 summers with your kids. And it's like, legally, but like, you meet families and they spend a lot of time together.

Yeah.

And you're like, oh, that's a whole different thing. I didn't know we could do that. You know, I didn't know that was something we could work towards. And so thinking about like what the goal is. And so the goal is not to have the shoes nicely lined up by the back door. The shoe, the, the goal is not to have, I remember I was talking to someone once, she was, she was in her 90s and she was like, people used to come over and be like, it doesn't look like you have kids. And she was like, I took that as a compliment. And I, I don't— she's like, I don't know how I could have possibly been so wrong. She was like, your house should look like you have kids. You're like, you have kids, why? What are you doing? So like, the goal is to have— it's to not have these people for 18 years and then eject them and go back to your selfish life. Like, you started a family. The goal is to have the family. Yeah, in the future. And so remembering that, running the things through the lens of that— again, it doesn't mean giving them whatever they want whenever they want it, because that is also at odds with that.

I would also say though, like, if you're a billionaire, you can go visit your kids for the holidays. You know, they don't need to come home. But the point is, they should want— they should want to come home, right? Like Like, you should— the success here is, uh, that, that when the authority ends, the relationship is still there.

Yeah.

And I think, uh, people lose sight of that.

I've never heard it like that. That's really good. Let's talk about speed reading.

Oh. Speed reading is a scam.

Well, how do I read faster?

I don't know. It's— I think it's illustrative that that's what you want to do. You're not like, how do I eat food faster? Is there a way to have sex faster? Like, the point is, stuff that's good, you want it— you want it to take how long it's supposed to take. So I don't know why we want to read faster. Like, if the question is, how do I read more? I got lots of answers to that question, but I don't think we should try to read faster, right? Like, I would say I read at a medium speed. I just spend a lot of time reading, and I spend a lot of time reading because it's worth doing. It's enjoyable to do, and also it's magic. The founder of Stoicism has a story about this. Zeno, the founder of Stoicism, he visits the Oracle at Delphi. The famous oracle, and he asks what the secret to the good life is. And he's told that wisdom comes when we begin to have conversations with the dead. And it's only later at a bookstore that he realizes that that's what books are. It's a way to talk to people who are dead, that we can converse with Marcus Aurelius through meditations, that we can read the speeches of Churchill, that we can read, you know, the poems of Emily Dickinson, that, uh, you know, we can read great novels, the campaigns of the greats.

Um, it's magic. It's fucking time travel. Like, here is someone who's no longer with us, transporting us to them, them to us. Breaking down, you know, there's a famous poem that says, you know, books are door-shaped, like they're portals to another world. And so anyways, the point is reading is spectacular. Like for $15 or $20 or fucking free at the library that you can have access to the brain of Julius Caesar or Napoleon You know, you can read from Stockdale, you can read from Marcus Aurelius, you can read from Epictetus, you can read from Frederick Douglass, you can read from Abraham Lincoln. You know, this is incredible. Like, like the, the amount of wisdom and hard-won experience inside the pages of the book is an incredible thing. And like, most people are like, nah, I'd like to, I'd like to learn by trial and error. Or they're like, eh, I don't know, a lot of good stuff on Instagram too, right? Like, it's ridiculous. Tolstoy talked about, like, you can converse with the wisest people who ever lived and you choose not to. So I think first and foremost, understanding what reading allows you to do makes the ROI of it much clearer.

Is it also entertaining and fun and relaxing? Sure. But it's an incredible thing that we have contained in these pages. Um, the other thing is, is, um, like, you got to make time for it. Like, there's no, there's no shortcut. Like, you got to do it. You got to make time for it. And if I looked at your screen time app, I promise you I could find the time, you know, like You have the time, you're just not spending it. And this is for all of us. Like, I could read more. I just get distracted by things. And so one of the reasons I like carry a physical book with me everywhere is like when I sit down because I'm a little early or someone's late or I have a few minutes between here or there, like, I want to read a book. I don't want to go into social media. I don't want to go into work. Like, I want to read. And I see that as part of my job. Like, it's crazy. Like, some of my best ideas, some of the biggest successes I've had I've had as an entrepreneur, but also as an employee, it came from things I read in books.

But for some reason, if someone had come into my office and I was sitting in a chair like this reading, they'd be like, I don't pay you to do this. Yet if I was sitting at my computer monitor checking ESPN, they'd have no idea. And so, so it's, it's, I think we, we need to do a better job understanding that reading is not just work. Like has a work benefit, but it's like some of the best— single best way you could spend your time. And I know that's my case for reading.

Right on, man. Well, Ryan, I know you got a flight to catch, but this is amazing. This was an awesome conversation. I'd love to have you back at some point.

I would be honored.

We do have a hot question. I almost forgot. One last thing. Hot question.

Audie Murphy tried to enlist in the Marines at 17. They rejected him for being too small.

The paratroopers rejected him too.

He finally got into the Army by gaining weight before the physical. 5'5", £112.

He went on to win every U.S. combat decoration for valor, including the Medal of Honor. 28 medals total. The most decorated American soldier in history. He came home, became a movie star, and was haunted by PTSD for the rest of his life. Slept with a loaded pistol under his pillow, got addicted to sleeping pills, locked himself in a hotel room and kicked it cold turkey. And then he did something nobody at his level was doing in the 1960s. He went public, talked openly about combat trauma, demanded the VA take it seriously. Died in a plane crash at age 45. Here's the question: tell me about Audie Murphy. What does the smallest, quietest guy in the room becoming the most decorated soldier in American history tell us about what real toughness actually looks like?

Well, they told us quite a bit about Audie Murphy right there. Just an incredible human being, an incredible American. Uh, he has a memoir called To Hell and Back, which, uh, I should have brought you because it's an amazing book, one of the one of the great memoirs of the 20th century. I'll tell you one little story about Audie Murphy. All those accomplishments are incredibly impressive. One of the ones he doesn't get enough credit for that I think in a way is, it's not harder, but it's rare, is so he becomes a movie star, country musician, right? And he's asked to do a bunch of endorsements. And he turns down all drug, Sorry, all cigarette and alcohol endorsements because he doesn't want to model that for kids. And so like, I just think like he did a lot of feats of discipline and a lot of feats of courage. Saying no to money is a thing that a lot of brave and powerful people have found it hard to do. And I just, in a way, Like there's physical courage and then there's moral courage. And the moral courage to say, hey, I'm not gonna do that, this doesn't feel right to me, is courage that we don't celebrate enough.

We don't give out medals for that kind of courage. And then the courage to speak out and to speak honestly about what you're struggling with, like vulnerability, like, hey, I'm not okay. Hey, even though I'm capable of all these things, this thing is kicking my ass. I'm struggling with this thing. Again, that's another form of courage that we don't celebrate enough and we don't hold up enough. And it's— and we wonder why it's, you know, we wonder why it's rare. It, it, uh, it moves me just, just as much. He's an incredible person. And, uh, you, you read some of those Medal of Honor citations for those guys and you're just— it's just absolutely unreal, right?

Yeah. Yeah. There's a follow-up here.

Okay.

I think you're gonna like this. What does this story say to every influencer right now selling alpha males? Alpha male stoicism.

Yeah, uh, I, uh, Andrew Tate is a fucking abuser of women, a shitty person, uh, a sex trafficker. And the idea that like that's who you should be taking life advice from is insane, right? Like Stoicism is not a recipe for making you a better sociopath. It is not this pick and choose thing where you take a couple motivational quotes and then, you know, you put it up next to an AI-generated picture of Marcus Aurelius with a 12-pack and you're like, I get it, right? It's a philosophy and it's a philosophy built around virtue. And the, the 4 virtues of Stoicism— courage, essential; discipline, essential; wisdom, essential— but the 4th is justice. That's ethics. That's the standards you hold yourself to. That's your contribution to society, to the world. And, um, you— none of the other virtues are of any worth if not balanced out by, or in fact directed at, justice, right? Like, um, courage on the battlefield, sure, very impressive, but what if you're fighting a horrible war? Like, I was in— stayed in Franklin, uh, and, you know, walked past the Confederate statue, and, uh, you know, it says, uh, There have never been braver men or a cause more honorable.

It's like, I can think of quite a few causes more honorable. Like, other than Nazism, it was literally the worst cause. Like, literally the worst cause to ever go to war for. Um, now it's complicated, and a lot of the men were drafted. Most of them didn't own slaves. They were told a bunch of lies by the slave powers. But let's not lie to ourselves about what that heroism was used for and what, what it would have looked like had it triumphed. Like, the world would have been a worse place. Like, they— their— in fact, their virtue, that military valor, was weaponized and spent in the wrong way for the wrong cause, right? And so there's no— like, that's, that's ultimately what philosophy is designed to help us wrestle with, was like, what's right and wrong? What do we owe other people? Are we making the world a better or worse place? And, uh, look, if, if the ideas of masculinity and toughness and resilience— if that's what, if that's what initially attracts you to Stoicism, awesome, right? You just, you just can't stop there. And I think probably you see this in your line of work, like the recruiting posters is what gets the people in the door, right?

But ultimately you got to buy into the values and the cause larger than yourself. And that it— if that's not you, that's actually like, like the most dangerous person because like the violence and the power and the strength, all that stuff is like, it's dangerous if, if not, if not moderated by and controlled by this ethical compass.

It can become very addictive.

Yeah. Yeah, that's a good question. Everyone should read, uh, To Hell and Back by Audie Murphy, just like An incredible, an incredible book. Right on. Yeah. Well, Ryan, dude, thank you.

Thank you, man. This was awesome. This was awesome. I really appreciate you coming. I had a great time. I hope you come back.

Yeah, sweet.

Cheers.

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