Stop Taking Yourself So Seriously | Chad Goes Deep

What can a comedian teach you about ego, shame, and philosophy? In today’s episode, Ryan sits down with Chad from Going Deep with Chad and JT https://www.youtube.com/channel/UCp6COGFcWCnEx9JbPIoYJLw to talk about the hilarious way they met, why playing a character without shame is liberating, what stand-up teaches us about ego, self-consciousness as a performer, and much more. Listen to Ryan’s episodes on the podcast Going Deep With Chad and JT https://open.spotify.com/episode/1Diyk4Uym6zKOwgwPeAyQ6: Listen to Ep.99 https://open.spotify.com/episode/1Diyk4Uym6zKOwgwPeAyQ6Listen to Ep.206 https://open.spotify.com/episode/1o3aecyPYGNfwosb0T5e1q See Chad and JT live in a city near you! Find tour dates on their website: https://www.chadandjt.com/ Follow Chad on Instagram @ ChadGoesDeep https://www.instagram.com/chadgoesdeep/?hl=en, on TikTok @ChadAndJT https://www.tiktok.com/@chadandjt, and on YouTube @ChadAndJTGoDeep https://www.youtube.com/@Chadandjtgodeep/videos Subscribe to Going Deep with Chad and JT https://www.youtube.com/channel/UCp6COGFcWCnEx9JbPIoYJLw: https://www.youtube.com/channel/UCp6COGFcWCnEx9JbPIoYJLw Subscribe to Academy of Chad https://www.youtube.com/@academyofchad on YouTube: https://www.youtube.com/@academyofchad Watch Chad and JT Go Deep https://www.netflix.com/title/81087423 on Netflix: https://www.netflix.com/title/81087423 👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content coming soon: dailystoic.com/premium http://dailystoic.com/premium 📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work":https://store.dailystoic.com/pages/wisdom-takes-work 🎙️ Follow The Daily Stoic Podcast on Instagram https://www.instagram.com/dailystoicpodcast/?hl=en: https://www.instagram.com/dailystoicpodcast 🎥 Watch top moments from The Daily Stoic Podcast https://www.youtube.com/@dailystoicpodcast on YouTube https://www.youtube.com/@dailystoicpodcast: https://www.youtube.com/@dailystoicpodcast ✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail 🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/ 📱 Follow us: Instagram https://www.instagram.com/dailystoic/,Twitter https://twitter.com/dailystoic,YouTube https://www.youtube.com/@DailyStoic,TikTok https://www.tiktok.com/@daily_stoic?lang=en, andFacebook https://www.facebook.com/dailystoic See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:03Ryan Holiday?

  Welcome to the weekend edition of the Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal,

• 0:46Ryan Holiday?

  and most importantly, to prepare for what the week ahead may bring.

• 0:54Ryan Holiday?

  Hey, it's Ryan. Welcome to another Saturday episode of the Daily Stoic Podcast. I want to take you back to 2019. I just spent a week in New York putting out Stillness is the Key. I did a book event, did a bunch of media, and then I was flying to Los Angeles to basically do that all again. My youngest son had just been born also. So like, I think I'd been gone for a week. So my wife was meeting me there. It was crazy, not getting a lot of sleep, just a lot going on. But I was feeling good about the book. I remember I was staying at the Los Angeles Athletic Club. And that morning, I found out that Stillness is the Key debuted at number one. That was pretty cool. And then I went for a swim.

• 1:38Ryan Holiday?

  And then, this is my memory of it. I could have the dates wrong, but I am almost positive that I don't. And then I had a podcast to record. And they were coming to meet me at my hotel room, which was at the Los Angeles Athletic Club. They were going to record it there. So these two guys come in and they set up their stuff. And then I get in my chair and we start to go. And they're just two of the biggest bros you have ever heard in your life. Your biggest California bros. And I, I just remember going, what is this? Is this real? Am I being pranked? Is this a test of my stoicism? Should I be really polite? Should I get up and leave? Is this like a Borat situation? That's like testing my good humor?

• 2:23Ryan Holiday?

  Am I supposed to play along? I, I just could not wrap my head around what this was. It was hilarious. They were very nice. And then that was the end of it. And then later, later, maybe they broke character or later, somebody told me like, no, this is like a bit, this is what these guys do. They, and you've probably seen them before. This is like one of their famous clips.

• 2:49Speaker 01

  All right, counsel. It is 1:15 a.m. Chad.

• 2:54Speaker 02

  Uh, what up, counsel? My name is Chad Kroeger.

• 2:56Speaker 01

  First of all, hang on just a moment.

• 2:57Speaker 02

  Yep.

• 2:58Speaker 01

  So you may have a seat until I call you up. Thank you very much.

• 3:02Speaker 02

  First, I just want to say thank you. Nothing gets me more stoked than six hours of civil service. I've come to you from a land called SoCal. And I also just want to say that I'm honored to be in this newfound land of Delaware. I wasn't aware that the government had inducted a 51st state, but I'm stoked that you joined America. Welcome.

• 3:20Ryan Holiday?

  What a state, dude.

• 3:21Speaker 02

  According to our sources, an attempt has been made to suppress their right to party. Not to get too lawyer-y on you, but this is in direct violation of the Constitution. Our forefathers valued the right to rage without government restriction.

• 3:36Ryan Holiday?

  So basically, that's what they do. I don't remember if I vaguely was familiar with that and, but I couldn't tell. Like, is this that thing? Or is this just, I'm thinking of that thing? But it's this kind of like low-key satire of where I grew up. I probably sound like these people to some of you with some of the things that I say. And we became friends. We stayed in touch. I did the podcast again a couple of years later. I watched their Netflix special, which was hilarious. And it's from that Netflix special that I learned. That Chad is actually from Sacramento. He went to a high school that I almost went to. And then I listened to him on Pete Holmes' podcast, which was a great episode of this podcast also.

• 4:22Ryan Holiday?

  But I listened to him on Pete Holmes and I was like, oh, this guy's like, obviously I know he's smart because he wouldn't be able to do this comedy if he wasn't. But this guy's actually really deep ironically and really thoughtful and really nice. And so I shot him a note afterwards and I said, hey, hit me up when you're ever in Austin. I'd love to hang out or have you on the podcast. And he did. He was here for some music festival, which he was performing at. He's the best. We talked about how he pulls off this comedy, which to me seems like it must require a certain amount of discipline. One of my favorite bits is where he walks up to like people who are really into their cars at like classic car shows and stuff, and he just quotes lines from Fast and the Furious as if he made them up.

• 5:07Ryan Holiday?

  Or another one where he listens to the Fifty Shades of Grey audiobook loudly in his car at gas stations or red lights and just doesn't let on that this is the most absurd thing ever. And he sort of sits in that discomfort that it creates again, like a Larry David or a Borat. And there's just something, you know, I couldn't do that. I would bust up or I'd be overwhelmed with shame. So we actually did talk a little bit about shamelessness, talked about self-consciousness. And does that get in the way of happiness or humor? Talking about leaning into your weirdness and then the craft of comedy and a lot more. Chad and JT's podcast, Go Deep, is hilarious. You can check out their YouTube channel.

• 5:49Ryan Holiday?

  Chad has another YouTube channel called Academy of Chad, where he has a bunch of satirical videos called Chad Philosophy. Let me play a clip from this video, Find Lasting Happiness with Epicurus.

• 6:01Speaker 02

  You ever feel like you're striving for too much, like too much money, too much fame, too much status, and you feel like the stoke is just out of reach? And then one day you're out surfing, you just got barreled, you're in between sets, a new tan is coming in, the sun's about to set and you think, whoa, this is peak stoke. I am now at one with the universe. Well, so did Epicurus, who's all about finding froth in the tranquil joys of friendship and the epicness of existence. In his philosophy, the pursuit of simple pleasures. Let's fricking dive in, dude.

• 6:30Ryan Holiday?

  You can catch him performing stand up all over the country as well. You can follow him on Instagram at Chad Goes Deep, on TikTok at Chad and JT, and on YouTube at Chad and JT Go Deep. Not everything in Stoicism has to be so serious. I think this is really funny. I think you'll like it. And I was really glad he came on the podcast and I hope you like this episode.

• 6:57Ryan Holiday?

  I think the first time I met you was one of the weirdest experiences of my life.

• 7:01Speaker 02

  Yeah, downtown LA.

• 7:02Ryan Holiday?

  Yeah, you guys came to my hotel room.

• 7:04Speaker 02

  Yeah, yeah, yeah.

• 7:05Ryan Holiday?

  And they told me absolutely nothing. They were like, no, it's these two guys that have a podcast. This is like 10 years ago, I think. So like podcasts were still like not real. They were like, it's two guys. They have this podcast. They're going to come to your hotel room. You just record it. But they didn't tell me it was like this kind of weird satire, like joke thing. Yeah. So I was just like, who? It was like Borat or something, you know? Like you're like, who are these people? And then it's like, it was in this uncanny valley between like real and not real. And then you guys went, you sat down. This would have been weird, even if it wasn't in character. You just went directly into an ad read.

• 7:44Speaker 02

  Did I?

• 7:45Ryan Holiday?

  For like, for like, for people who don't know, you do like the intros and the ad reads.

• 7:51Speaker 02

  Yeah.

• 7:51Ryan Holiday?

  Separate when they're not there, so they're not sitting there. But you guys went directly into an ad read for like a manscaping company? And I'm like, these people are in my room for the next hour. What?

• 8:03Speaker 02

  Oh, man, I forgot we used to do that. We used to do the ad read right with the guy. Yeah, you know, that was really early on with our podcast too. Because we were kind of unsure. We just started having guests.

• 8:13Ryan Holiday?

  Yeah.

• 8:14Speaker 02

  And so it was in a moment where we were trying to just always be in character. So we were like, we're like, do we be in character? Do we ask questions in character? And we first started out and started like gaining some like traction. All of our meetings and like we met with like producers.

• 8:28Ryan Holiday?

  Yeah.

• 8:28Speaker 02

  We did them all in character.

• 8:29Ryan Holiday?

  Ah.

• 8:30Speaker 02

  And it worked for some, but for others, they're like.

• 8:34Ryan Holiday?

  Yeah, but you can't.

• 8:35Speaker 02

  They're like, what are you doing? And we, to us, we were like, no, we have to stay in character. Like we had this one guy and he's like, he's like, guys, stop. And then our agent was like, hey, if they tell you to break, you can break. I'm like, okay.

• 8:50Ryan Holiday?

  I don't remember what book it was for.

• 8:52Speaker 02

  Stillness is the key.

• 8:53Ryan Holiday?

  Okay, so this was, I guess, six or seven years ago. There's a thing that publicists do, which is like, on the one hand, they're trying to get all the big things that move the needle. And then there's just like other, other things, they're just trying to like, fill up the list, you know? And you never know like which one you're gonna get.

• 9:09Speaker 02

  Yeah.

• 9:10Ryan Holiday?

  But sometimes they obviously, it's like they have a relationship with someone or they know something. And they're just like, just trying to get, because it makes, I mean, you're like, hey, I know you have this book about philosophy. You should talk to Chad and JT. That's like your perfect audience.

• 9:23Speaker 02

  Yeah, yeah, yeah.

• 9:24Ryan Holiday?

  So, so like, the fact that they booked it was hilarious. And then they just didn't brief me on it at all.

• 9:31Speaker 02

  Right, right.

• 9:32Ryan Holiday?

  Okay, this is out of your wheelhouse, but it's gonna be really fun.

• 9:35Speaker 02

  Yeah.

• 9:36Ryan Holiday?

  Or whatever. Like, they didn't tell me about it at all.

• 9:38Speaker 02

  Yeah, yeah.

• 9:39Ryan Holiday?

  They're just like, I know you were, like, you're doing NPR later in the day. You know, you did the evening, you did like the local news yesterday. And then we're just squeezing in Chad and JT, nothing, nothing we need to tell you about this.

• 9:52Speaker 02

  Yeah, yeah, yeah.

• 9:53Ryan Holiday?

  It's just an ordinary interview. And then I'm like, what the fuck is happening?

• 9:57Speaker 02

  That's so funny. I, I didn't, uh, man, it's so funny to look back on that. Yeah. And we probably just left and you're like, what was?

• 10:03Ryan Holiday?

  Yeah, I would love to, I like, the only reason I haven't gone back to watch it is that it might ruin whatever, like, I, I think so fondly of it. But I'm just remembering it being like, what is my life right now? And are these people like this?

• 10:18Speaker 02

  Yeah.

• 10:18Ryan Holiday?

  Because I grew up in California. So like, it's, I think that's what is so compelling about the characters is that they are in the uncanny valley of like, you don't. If you, I think, you have to be pretty dense to be like, Borat, this is real.

• 10:31Speaker 02

  Right.

• 10:31Ryan Holiday?

  You know, like, there's a whole world that you would have to go in to buy that.

• 10:36Speaker 02

  Yeah.

• 10:36Ryan Holiday?

  But like, if you come from California, like, this isn't that out of the ordinary.

• 10:40Speaker 02

  No.

• 10:41Ryan Holiday?

  Weird, but.

• 10:42Speaker 02

  Yeah, it's, I mean, it's very close to who I am.

• 10:45Ryan Holiday?

  Yeah.

• 10:45Speaker 02

  You know, it's, my brother is sometimes like, that's who you really are in a sense, because like, in, in, in real life, or when I'm not sort of like, you know. Playing Chad or whatever, I'm like kind of a little bit guarded and not guarded, but just a little bit more introverted. But when I'm like, feel like kind of fully like safe with people, that's like when I'm my, and he's like Chad is who you really are like on the inside. So.

• 11:10Ryan Holiday?

  There's like a Michael Scottness to it where it's like, what is a person who doesn't feel shame, which like shame is a constraint on all of us. So I imagine if you removed shame or self-consciousness, there's something very freeing, but then also kind of terrifying about that guy.

• 11:30Speaker 02

  Totally. Yeah. And I've always admired, those are always my favorite characters in TV and you know, Kramer, Michael Scott. It's like people who go through life who were to you, it just looks like they're in their minds, they're always winning.

• 11:43Ryan Holiday?

  Yeah.

• 11:43Speaker 02

  And they're always kind of crushing and they're not even aware of like what other people are thinking or what other people think of them. And I always, whenever I would watch that, especially watching Seinfeld, I'd always be, it just felt so freeing to watch for me.

• 11:55Ryan Holiday?

  Yeah.

• 11:55Speaker 02

  And so I think that's why I kind of gravitated towards playing, you know, a character like that because it's just, that's kind of how I want to be in life.

• 12:04Ryan Holiday?

  Did you ever do the Seinfeld reality tour in New York?

• 12:07Speaker 02

  No, I haven't done that.

• 12:08Ryan Holiday?

  Uh, but it's like led by the actual Kramer.

• 12:11Speaker 02

  Is it?

• 12:12Ryan Holiday?

  Yeah. Yeah. It's like that whole thing is real. So like, remember there's like an arc in later in the season where Kramer does the Peterman reality tour because he's Peter. It's the whole thing. But Kenny Kramer was a comic that Jerry and Larry David were friends with or lived down the hall from them or whatever. They based it on him. And then as the show blew up, he kind of became famous, but he didn't participate. And then he started a real bus tour and I went on it when I was like in high school or something.

• 12:38Speaker 02

  Yeah.

• 12:39Ryan Holiday?

  And you're like, it's kind of like cool behind the scenes, but you're also like, there is something like sad and weird about it that like, you're like, oh, it actually wouldn't be fun to be Kramer because like in real life, this is what Kramer is doing.

• 12:49Speaker 02

  Exactly.

• 12:50Ryan Holiday?

  He doesn't actually have anything going on. This is like. His main thing, but it was weird.

• 12:55Speaker 02

  It's interesting how like movies or TV shows can kind of glorify that. Like, I think a good example is Brad Pitt's character in Once Upon a Time in Hollywood. Cliff Booth, because he lives in a trailer, he's single, you know, he's Quentin Tarantino. He's like, he's basically a loser. But when you see Brad Pitt playing him, you're like, I want to be that guy. And there's an, it's interesting how, you know, in TV and film, it's able to do that.

• 13:19Ryan Holiday?

  Yeah, it is. You know, Michael Schur, so he has this book called How to Be Perfect, which is actually a book. It's very smart, but it's a book about moral philosophy. And they have this section in it about like, whether it would be awesome to be Michael Scott or not.

• 13:32Speaker 02

  Right.

• 13:32Ryan Holiday?

  Like, is actually that the greatest person to be? Because you're like the Dunning Kruger effect, where you're like stupid, but you're not smart enough to know that you're stupid. Ignorance is bliss. And then he kind of goes like, would, maybe a better example is like, would it be awesome to be Ron Gronkowski?

• 13:48Speaker 02

  Right.

• 13:48Ryan Holiday?

  Because like, the problem with Michael Scott is his life is objectively very sad. Right? He's, you know, cooking bacon for himself on his Foreman grill and no one wants to be with it. Like, until the relatively close to the end of the show, like, his life sucks. But like, is there something about the sort of like, oh fish, but good natured? And mostly hidden green lights on the course. Like, would you rather be that than someone with self-awareness?

• 14:19Speaker 02

  Yeah, I mean, the kind of the golden retriever who's crushing it.

• 14:23Ryan Holiday?

  Yeah.

• 14:25Speaker 02

  I mean, that sounds awesome to me.

• 14:28Ryan Holiday?

  Yeah, that's, Ron Gronkowski seems like a big golden retriever, like a derpy dog. Who actually, from what I've read, is actually like, pretty smart. Like, he's like, I only live on my, you know, my endorsement money or whatever. Like, it seems like he's playing a bit of a character, actually. But like, there's something about self-consciousness, I think, that is probably at odds with happiness. That's different than self-awareness.

• 14:54Speaker 02

  Right.

• 14:55Ryan Holiday?

  But that like, sensitivity to how you're coming off.

• 14:58Speaker 02

  Well, oftentimes, if we're shooting something and like, we're kind of in character, it is very freeing. That freeing sense of like, just being totally unaware of how other people are feeling.

• 15:08Ryan Holiday?

  Yeah.

• 15:09Speaker 02

  Is very, uh, yeah, kinda like what I was saying earlier. That's kinda why I gravitate towards that, cuz it's like, that's kinda how I want to live.

• 15:15Ryan Holiday?

  Yeah.

• 15:16Speaker 02

  I'm the fifth child, so I think I was always kind of branded as that when I was growing up is like kinda like-

• 15:22Ryan Holiday?

  The baby to everyone, so you're like-

• 15:24Speaker 02

  I'm the, I'm the baby, they're like, you're gonna win the lottery, you're just lucky.

• 15:27Ryan Holiday?

  Yeah.

• 15:28Speaker 02

  You know, you, you just kind of like, you're just kinda cruising through life and, and like, I studied philosophy in college and, you know, like, my older brothers in finance, you know, they're just all very focused on successful. And then I was like, yeah, I'm gonna study philosophy. They're like, what are you gonna do with that? I'm like, I don't know.

• 15:42Ryan Holiday?

  Comedy, obviously.

• 15:43Speaker 02

  Steve Martin did it.

• 15:44Ryan Holiday?

  Yeah, yeah, yeah. It was, it was funny, speaking of self-consciousness, cuz I did this talk this morning. It was like a thousand people. The venue was supposed to seat a thousand people, but you ever get in front of a group? And it's like, it's not, I wasn't supposed to deliver the audience, so it's not on me. But you're just like, you're like seeing empty chairs.

• 16:00Speaker 02

  Mm-hmm.

• 16:01Ryan Holiday?

  And you're just like, it could be full or it's not full.

• 16:03Speaker 02

  Yeah.

• 16:04Ryan Holiday?

  Why are they not here? Do they leave? So now you're thinking about what you're doing as you're doing it and what you're not doing is doing it.

• 16:10Speaker 02

  Yeah.

• 16:11Ryan Holiday?

  I think art, comedy, writing, sports, like, the second you're kind of like seeing yourself as you're doing it, you're out of it. And there's probably something about being in the character, because the character doesn't think about any of that. You don't have to think about any of it and you're just in it.

• 16:26Speaker 02

  Yeah, I, I, I used to, or I still do, like, really enjoy bombing, because especially when I started doing that kind of onstage, like, I'd sort of developed a persona onstage and it's like, sometimes, especially early on, audiences would just be like, well, what are you doing? And like-

• 16:40Ryan Holiday?

  Yeah.

• 16:40Speaker 02

  To me, that was so satisfying, cuz I'm like, oh, they think it's real. And so I kind of found, there's like a, a freeingness, whereas if I'm being more myself, you can kinda hone in, like, you know, if everyone's laughing, but there's one guy-

• 16:53Ryan Holiday?

  Yeah.

• 16:53Speaker 02

  Not, he's like- Kind of looking at his phone, or you're just like, kind of like, looking around. You just hone in on that, and it's, it does kind of like, break you from that kind of like, performance kind of flow.

• 17:04Ryan Holiday?

  Well, it must be weird for you, because if the audience is in on the joke, like, they know who you are.

• 17:08Speaker 02

  Yeah.

• 17:09Ryan Holiday?

  That's much more favorable to you.

• 17:11Speaker 02

  Yeah.

• 17:11Ryan Holiday?

  Than when you're performing in front, just like, if you're just going up in front of a, at a club, or if you're like, in front of a city council meeting, or whatever. Like, the character kind of thrives on the, the not receptiveness to it. So, in a way, like, a bad audience is a good audience for you, and a good audience is kind of a bad audience.

• 17:29Speaker 02

  True, yeah. Like, if people, if people are familiar with me, then they're, they're kind of in on the joke, and then the surprise isn't there as much.

• 17:37Ryan Holiday?

  Yeah.

• 17:37Speaker 02

  So, you kind of have to work to, to, you know, whereas if it's an audience that doesn't know who I am, you know, sometimes it can really pop, because it's like, the surprise is there from the jump. But as soon as I walk onstage, they're kind of like, something's off.

• 17:51Ryan Holiday?

  Yeah.

• 17:52Speaker 02

  And so, they're, and if they buy into it, they're on board for the whole ride. And so, it's kind of, it doesn't even really matter about like, the, the, like, writing. If I'm doing stand-up, if the writing or punchlines, those matter, but it's, it's more in just my way of being.

• 18:06Ryan Holiday?

  Yeah.

• 18:07Speaker 02

  That I think makes them laugh, which is something I noticed with, like, Sebastian Maniscalco, or are you a fan of his? He, like, when I watched him onstage for the first time, the way he walked up made me laugh. And I was like, oh, I want to do that, where he had this, like, Italian kind of, like, swagger. But it was just so funny to me, and I'm like, man, if you can just, like, exude, like, a funny, weird confidence as you walk onstage.

• 18:33Ryan Holiday?

  Well, because he's playing a character. He's acting like it's him, but he's closer to, like, Larry the Cable Guy than he is Jerry Seinfeld. In the sense of, it's like, it's this thing that he's doing.

• 18:43Speaker 02

  Yeah.

• 18:43Ryan Holiday?

  Yeah.

• 18:44Speaker 02

  Yeah, it's like, that's his persona, that's sort of the side of himself that he's honed in on, that's, that's funny.

• 18:49Ryan Holiday?

  Yeah. I like stand-up comics who are more like writer comic, like, they're just doing it. To me, when it feels like they're performing.

• 18:56Speaker 02

  Right.

• 18:56Ryan Holiday?

  Then it, it gets more towards like, one-man show, or spoken word, and then it just, it punctures the illusion for me. Like, I think, to me, great stand-up comedy, even though it actually is a highly honed... Performance that they are just reciting a script for. I like the feeling that they're like, what am I going to talk about next? You know what I mean? Like that, to me, that, those are more my favorites.

• 19:18Speaker 02

  Yeah, where it's, it's sort of stream of consciousness. It feels like stream of consciousness, like this is-

• 19:22Ryan Holiday?

  Even though they know exactly the hour they're performing. And when they're hitting all the spot, but it feels like they're just saying the stuff. Like, I don't like TED Talk-y speakers either, where they're like, they've performed the hand gestures and they like took a class on charisma or something.

• 19:40Speaker 02

  And where it's all scripted and you kind of, yeah. Whereas like Bill Burr, I think Bill Burr is really good at that, where he can, he can rant on stage. And it feels like it's all-

• 19:49Ryan Holiday?

  Yes.

• 19:49Speaker 02

  Coming from his, and, or Chappelle, like-

• 19:52Ryan Holiday?

  Yeah.

• 19:52Speaker 02

  You see Chappelle, he always feels like it's unrehearsed.

• 19:57Ryan Holiday?

  Yes.

• 19:58Speaker 02

  And it's like, he's like, this is just what I'm feeling. And yeah, he's, he's really good at creating that. Cause sometimes you'll watch his specials, I'm like, did he just practice this at all? Or is this just how he talks?

• 20:09Ryan Holiday?

  Yeah, but he must have.

• 20:10Speaker 02

  Oh, yeah, I think-

• 20:11Ryan Holiday?

  No one's booking a theater and paying for a production to be like, let's hope it's good.

• 20:15Speaker 02

  Yeah, yeah, yeah. Yeah, that's like another level of talent where it's, it's-

• 20:20Ryan Holiday?

  Yeah, I mean, it's all about making it look effortless. Or that you're not trying.

• 20:37Ryan Holiday?

  It was funny because, so after you guys came, I was like, what the fuck is this? And then a couple of months later, whatever, I saw one of the clip, like I saw one of the sort of viral clips.

• 20:45Speaker 02

  Yeah.

• 20:45Ryan Holiday?

  And it, it was very triggering for me because when I was 20, maybe, I just started at American Apparel. I think I've told this story before, but I just started at American Apparel. And the company was like a disaster. So he would just like, there would just be these like girls in his life. He's like, I think we should have another store in Toronto. Go figure it out.

• 21:04Speaker 02

  Yeah.

• 21:05Ryan Holiday?

  You know, he would just like assign these people had no idea what they were doing to like, open a store for a company doing $500 million in sales. And so he had done this in San Francisco and he had sent this girl to open this store in the Mission District. And actually, the Mission District had some weird San Franciscany law that, that banned big box retailers. But their definition of a big box retailer was any- Restaurant or retailer with more than 10 locations. Oh, interesting. So, so suddenly, like, to open this store, like, they just, they thought, they'd sign the lease, they're gonna open it, they put up the coming soon sign, and then it all came to a screeching halt when, like, these community activists were like, no, no, you're a big box retailer, you can't come gentrify our neighborhood. Mm-hmm.

• 21:48Ryan Holiday?

  And it was gonna be subjected to, like, a city council meeting with, like, public opinion. Yeah, yeah, yeah. And so, they were like, Ryan, you have to go. Uh-huh. I didn't do this. Also, I have no training in this whatsoever. Right, right, right. But they're like, no, no, you need to go address this, like, city council meeting. And so I go, they told me I would speak first, I had five minutes, so I prepared five minutes of remarks, while, like, so many hundreds of people came, that they, I get up there and they're like, actually, you have two minutes. Wow. I don't think I've ever spoken in public before. Mm-hmm. And I, so I had to, somehow, I do my remarks, they don't go well, and I'm wearing an American Apparel shirt, like, a gray shirt, and, uh, have you ever read A Man in Full? No. It's the Tom Womble, I'll give it to you in there, but there's this scene between,

• 22:32Ryan Holiday?

  like, a loan agent and the, the main character of the book, and he's like, my goal is to give him saddlebags, and they go, what's saddlebags? He's like, I'm gonna lay into this dude so much, give him, he's like, you're gonna start to see the saddlebags under his arms. Yeah. So you can see pictures of this, because it was, like, covered, and I'm just, like, soaked, I'm just, like, I'm out, I'm losing it. Anyways, so I do my thing, and I go, okay, I did my part, whatever, that's as bad as it's gonna get. Right. And then, they direct me, I have to sit in the front row, and then be addressed by the community. Oh, wow. For the next two hours. Oh, no. Um, yeah. And these are wackos from San Francisco, these are community activists from San Francisco, objecting to a, what they think is a big box retailer gentrifying their neighborhood. Yeah. So, yeah, I just sat there and I got yelled at.

• 23:16Ryan Holiday?

  And you were representing that. Representing for two, for two hours, and, you know, it's like, this woman gets up and she's like, I was hoping to open, like, a vintage sex toy store. Mm-hmm. Like, that was a real thing that she said. Yeah. And I'm like, what? And then this one guy gets up and he goes, and this is why I thought of you guys. It was like pros and again, right. And he's like, he gets up as a pro. And he's like, I was here to speak in favor of American Apparel, but that's because they paid me. He was doing performance art. Right. Where he was pretending that he was a paid plant. Yeah. To speak, and then was ripping the mask off to show that he was actually against it.

• 24:00Ryan Holiday?

  And that the corporate interest was trying to bribe the community. Uh huh. And it was just like, I'm like, what is happening? Like, this dude is do, like, there's not even television cameras. Like, he's just doing this art, like, for himself. And then there were just all the people, like, like what you guys do, where they're just getting up and they're just talking about. Right. Totally, like, I can't get my television to work, you know, or whatever. Yeah, yeah, yeah. I just sit there for two hours. One person earnestly spoke in favor. And then two hours. Wow. Of no's. And then I just had to go home. When you're sitting there, like, how are you, because I'll watch the council when they're berating the council, the council will kind of just like, kind of like, kind of. Yeah. Not even, wow, where you just sort of just. Yeah, and I'm like 20 years old. Oh, God.

• 24:43Ryan Holiday?

  Like, I have no idea, like, and, and then, yeah, I'm, and it's like, I didn't. It wasn't my idea to open the store. It wasn't my responsibility to open the store. I've worked at this place for like six months. I don't know fucking nothing. Wow. And I was, it was just like, what is my life right now? I mean, now it's hilarious to me, but I was just like, in the morning, I was like, what is happening? Yeah. Did they, uh, did they give you a script? Did you write it? Like? I wrote like a little, I wrote five minutes of remarks. Yeah. I mean, if I'm like, hey, go up, do five minutes tonight. And then as you walk on stage, they're like, actually two. You're like, fuck, this is like a whole, there's a whole rhythm, like. Yeah, yeah, yeah. I can't, like, two is a world of different. Yeah. Difference than five. And so I think I, you know, I barely got through my.

• 25:27Ryan Holiday?

  Things, which I had written out. And even if I delivered like, like some Rudy-esque speech, they would have been like, no. Like, there's, there's nothing I could have, it was a foregone conclusion. We should have just eaten the lease. Yeah. From the beginning. Yeah. The punchline to the whole thing is like, the Mission District is now one of the most gentrified neighborhoods in San Francisco. It was totally pointless. Yeah. But that was. And, and did, did you guys end up, you ended up opening the store? No, I don't think so. Oh, no. No, no, I think they just ate a 10-year lease.

• 25:59Speaker 02

  Yeah, I, that's so interesting because I'll watch the council too. I mean, they'll have people just screaming at them. Every meeting they'll be like calling for them to be, you know, arrested.

• 26:08Ryan Holiday?

  Yeah.

• 26:09Speaker 02

  And then they'll be like, alright, next agenda item. Like, they're so, like, they deal with that so much that they're able to just kinda, I think they're compartmentalized that.

• 26:17Ryan Holiday?

  Yeah, yeah.

• 26:18Speaker 02

  Kind of like-

• 26:18Ryan Holiday?

  Like, there must be some briefing you get-

• 26:20Speaker 02

  Yeah.

• 26:20Ryan Holiday?

  The day after you get elected. And they're like, okay, let me tell you how a city council meeting goes. These are the 20 people that attend all the meetings.

• 26:28Speaker 02

  Yeah.

• 26:29Ryan Holiday?

  This is what they talk about.

• 26:30Speaker 02

  Yeah.

• 26:30Ryan Holiday?

  You cannot engage in any way. These are the red lines that we enforce.

• 26:34Speaker 02

  Mm-hmm.

• 26:35Ryan Holiday?

  And then, you know, just think about what we're gonna have for dinner. Or whatever. Like, because there is a kind of a, they're having to be very self-controlled.

• 26:43Speaker 02

  Yes. I've only seen a couple instances where the council has responded. Usually LA City Council, because it gets so heated in there.

• 26:51Ryan Holiday?

  Right.

• 26:52Speaker 02

  You know, if someone from the public is saying racist remarks or something. I've seen them actually engage.

• 26:58Ryan Holiday?

  Yeah.

• 26:59Speaker 02

  But other than that, they're, they're very, they're able to just sort of take it in and they'll be like, okay, well, I, you know, propose this change to the agenda.

• 27:06Ryan Holiday?

  Yeah, yeah.

• 27:07Speaker 02

  Meanwhile, someone's just calling them a terrorist or something. Yeah, so when we go in the council, actually, people, they enjoy it. They're pumped.

• 27:15Ryan Holiday?

  Well, because it's, it's totally off-topic-

• 27:17Speaker 02

  Yeah.

• 27:17Ryan Holiday?

  But it's not, like, alarming in any way.

• 27:20Speaker 02

  Mm-hmm.

• 27:21Ryan Holiday?

  And it's like, it's, I don't know, it's like a puppy just ran up or something.

• 27:24Speaker 02

  Yeah.

• 27:24Ryan Holiday?

  What's it gonna do?

• 27:25Speaker 02

  Yeah, exactly.

• 27:26Ryan Holiday?

  Although some of it's weird. It's not like creepy, like, you know, like-

• 27:29Speaker 02

  Yeah, it's positive trolling, that's what we call it.

• 27:31Ryan Holiday?

  Yes.

• 27:32Speaker 02

  Yeah. Positive trolling. Yeah, yeah, yeah.

• 27:35Speaker 02

  It's a lot of fun, yeah.

• 27:36Ryan Holiday?

  What is the difference between positive trolling and regular trolling? Like, where do you draw the line?

• 27:40Speaker 02

  I think positive trolling is generally the joke is on us.

• 27:44Ryan Holiday?

  Yeah.

• 27:44Speaker 02

  Um, so we're always trying to make fun of ourselves. Negative trolling is, is, I think, when you come in with the intention of trying to elicit a reaction from them-

• 27:52Ryan Holiday?

  Right.

• 27:53Speaker 02

  And usually attacking someone or, or being offensive in a way to get-

• 27:59Speaker 02

  A negative reaction from someone.

• 28:00Ryan Holiday?

  Right, right. Like, is it where he, the famous one where he does like the thing during the national, he sings the national anthem. He's trying to trample on whatever they hold most sacred.

• 28:11Speaker 02

  Yeah.

• 28:11Ryan Holiday?

  You're like, just going on this like benign rant around a seemingly nonsense issue.

• 28:19Speaker 02

  Exactly, yeah. Sometimes trying to have like a hidden message underneath, but a lot of times it's just being silly and

• 28:24Ryan Holiday?

  Yes.

• 28:25Speaker 02

  And just trying to, you know, put the joke, that's our main thing is the joke is always on us. We always try to, we never really want to be punching down or making fun of someone.

• 28:34Ryan Holiday?

  Right.

• 28:34Speaker 02

  And then if someone gives us a negative reaction, that's sort of on them.

• 28:38Ryan Holiday?

  Yeah.

• 28:38Speaker 02

  Like, I remember when we did like a video where we were handing out masks in Huntington Beach in like 2020. And we were just trying to be as naive and innocent as possible, because it was during like the lockdown protests. And so we just had a box full of masks and we were handing them out in Huntington Beach and.

• 28:54Ryan Holiday?

  And which Huntington Beach is like weirdly conservative, right?

• 28:57Speaker 02

  Yeah, yeah, yeah.

• 28:58Ryan Holiday?

  It's like kind of a, it's like a MAGA like dot in the middle of California.

• 29:02Speaker 02

  Exactly. Yeah, yeah, yeah. So we knew what we were doing.

• 29:04Ryan Holiday?

  Yeah.

• 29:05Speaker 02

  It was maybe, actually that was maybe more trolling than just positive trolling, but the naivete that we, it's like, oh, we're just handing out masks and then like allowing people to kind of decide about how they want to react is kind of, so if it's negative, that's sort of, it's on them, if that makes sense.

• 29:22Ryan Holiday?

  I feel like weirdly the stoic thing for you guys is like the, one standing character must be difficult. But like, the restraint to take the thing they're doing seriously must be tough. Like, when you pull up and you're blasting the audiobook of Fifty Shades of Grey at a gas station. Or you're just going up to these dudes who really care about cars.

• 29:44Speaker 02

  Yeah.

• 29:44Ryan Holiday?

  And you're just quoting Fast and the Furious as if they're real car observations.

• 29:50Speaker 02

  Yeah.

• 29:51Ryan Holiday?

  Like, it only works if you act like it's not the dumbest thing ever.

• 29:56Speaker 02

  Yes. Yeah, where it's, they say in comedy, it's like, to the character, it's not comedic. To the character, it's, you know, if you're, if you're playing, if you're in comedy, you're playing a character and you're Trying to be funny, like Michael Scott, you know, Steve Carell, you know, I think he's playing that where he believes that whatever he's doing is is right. And it's like, kind of.

• 30:19Ryan Holiday?

  That's what makes sense to him. It makes sense to him.

• 30:21Speaker 02

  Makes sense to him. Yeah. So I think, yeah, it's sort of buying into that where you're not, I think, yeah, that just the golden rule is not trying to be funny.

• 30:29Ryan Holiday?

  Right.

• 30:30Speaker 02

  It's taking yourself so seriously that it.

• 30:33Ryan Holiday?

  But that's the, that's the self consciousness thing that you have to conquer, right?

• 30:36Speaker 02

  Yeah.

• 30:37Ryan Holiday?

  You have to be in the thing, doing it.

• 30:40Speaker 02

  Yeah.

• 30:41Ryan Holiday?

  Even though if you zoomed out, you know that you set, you set up the premise. So you know, the premise is funny.

• 30:47Speaker 02

  Yeah.

• 30:48Ryan Holiday?

  And you're doing it to be funny. And yet you have to embody this space, this physical body, where you're insisting that it's not funny.

• 30:55Speaker 02

  Yes.

• 30:56Ryan Holiday?

  And that would require, I think, a lot of self-control.

• 30:59Speaker 02

  Yeah, the kind of, if someone's laughing, they're laughing at you and there's that temptation to kind of break the tension and laugh with them.

• 31:07Ryan Holiday?

  Smile to match the, you're having to not match the emotion of the person across from you.

• 31:12Speaker 02

  Yeah. And your instincts would be like, yeah, smile, break the tension. Let them know that you're joking.

• 31:16Ryan Holiday?

  Yes.

• 31:17Speaker 02

  And kind of let them know that you're not.

• 31:19Ryan Holiday?

  Yeah.

• 31:19Speaker 02

  Insane. But then the, the kind of, I guess, the, I guess, craft of it is sort of like, no, go deeper into the, to the opposite of that, like, get more serious, get more. And that's actually why I stopped during, when we started doing podcasts, trying to interview a character, because it was like 60 minutes, you know?

• 31:36Ryan Holiday?

  Yeah.

• 31:37Speaker 02

  And we're like, and at a certain point, you're like, man, like, I just want to let them know.

• 31:44Speaker 02

  There is that, that is like a discipline, I think, to kind of, discipline to that kind of performance. Yeah.

• 31:50Ryan Holiday?

  You have to do that when you have kids, where it's like, they're telling you something and it's like the dumbest thing ever.

• 31:54Speaker 02

  Right.

• 31:55Ryan Holiday?

  And you have to be like, oh, yeah, that's a, like, not just like, oh, you have to listen to, you know, the acting of like, listening to boring stories, but more like. I have to take what you think is a grievous wrong very seriously. Yeah. Even though it's comically absurd. Yeah. You know? Yeah. Or like you have to take the fear seriously. You can't, you can't just be like, no, no, no, it's all right. Or like, no, it doesn't matter. Like you have to, you have to like first engage with it as serious and then sort of talk them out of it or talk them through it. Right. But your instinct is to be like, what? You know, like, and you, you can't do that. Yeah, yeah, yeah, totally. How many kids do you have? Two. Two. Uh, that must be fun. It's a lot. Yeah, yeah, it's a lot, yeah. Yeah, they're, they're like maniacs. How old are they now?

• 32:40Ryan Holiday?

  Uh, nine and one turned six yesterday, day before yesterday. But yeah, it's also funny, like my oldest, he took like an improv class in school or in like a club. So then I was like, what happened was I, I made a huge mistake, which is that I was like, I told him the Michael Scott thing from the first season of The Office where he's in improv. And in every scene, he like kicks down the door and he just goes like, freeze FBI, which he immediately thought was the funniest thing of all time. Yeah. And then he told the other kids in the class. And so they, it just like essentially broke the. They all did that. Because like on the Michael Scott level, they just immedi-, like they understood what Michael Scott understood, which is like, that's the most intense thing you can do. Right, right.

• 33:23Ryan Holiday?

  Even though, you know, and so like watching this performance and they're all like trying to do it, you know? It was funny. But then I started showing him other stuff, like I showed him stuff from The Office and then we watched like Saturday Night Live. And now he just like quotes stuff from, and you're just like, oh, how are we like getting the same? Right. We're like enjoying the same jokes? Yeah. That's weird. Like he really likes like the Nate Bargatze, like George Washington one, like, because like life is absurd and he doesn't understand why it's certain, like, cause he's always like, how many is several? You know, like, uh, you know, or like, like, so, so at some level, he's get, he's already sort of picking up on like the fucked up-ness of like. Why things are the way that they are in the world, you know?

• 34:07Speaker 02

  Yeah, that must be a trip like it's because, you know, seeing them from a baby to when they're actually starting to develop a personality and like understand things. And I'm sure that's kind of like, oh, you actually understand.

• 34:19Ryan Holiday?

  Well, to understand something enough to see what's funny about it.

• 34:23Speaker 02

  Right.

• 34:23Ryan Holiday?

  Is like another level of understanding. And then it kind of sneaks up on you like when that's happening. There's one, it's called King Brothers Toyota on SNL. Oh, it's, it's like, it's a probably not funny for anyone listening, but it's a, it's a Toyota like sales commercial for this, like some local dealership. But the local dealership is having trouble selling the cars because they put in a Raisin Canes and a Chick-fil-A like near the exit. And you know how like how the, the drive-throughs back up?

• 34:53Speaker 02

  Yeah.

• 34:54Ryan Holiday?

  And so like the whole thing is about how they take exit 260, but you, if you get in the right lane, you'll get stuck and you can't get into the like.

• 35:02Speaker 02

  Right, yeah.

• 35:03Ryan Holiday?

  And it's like going over and then like, we were driving yesterday and we passed like the Chick-fil-A that's in this town. And he goes like, hard, get hard in that left lane, you know? And he's like doing the thing. And it's like, this is what I remember doing with my friends as a kid. And now like you're already, you're like quoting, now we're, now we're quoting stuff back together. That like really snuck up on me.

• 35:26Speaker 02

  Yeah, it's so interesting.

• 35:27Ryan Holiday?

  What age do you think you can watch Dumb and Dumber? Cause I'm trying to think, I'm trying to like, I'm going back through and like, what are things that, you know, like, and, and then it's like, sometimes you watch, you know, oh, fuck, I forgot, like somebody kills himself in the middle of this or whatever. And then you're like, it's not cursing. I don't care about, but it's like some, it's like, oh, wait, there's a weird like orgy scene or something. You're like, what is this? So I'm trying to think, trying to think, when, when did I watch Dumb and Dumber?

• 35:51Speaker 02

  What's funny is I, I think I, I started watching those movies pretty early.

• 35:55Ryan Holiday?

  Yeah.

• 35:55Speaker 02

  I was watching Seinfeld in like first grade and my, my teacher was like, I was like, what she's like, what did you do last night? I'm like, I'll watch the series finale of Seinfeld. And she's like, what? And like JT, my like comedy partner, he was watching like Heat when he was like five.

• 36:12Ryan Holiday?

  So for both of you, this is not like an endorsement of doing this early. It's like, oh, this is why they ended up the way they.

• 36:18Speaker 02

  Exactly. Yeah. So maybe, maybe I'm like, you should wait. I remember watching Austin Powers when it came out. I was seven. So is that comparable to Dumb and Dumber?

• 36:27Ryan Holiday?

  I think Austin Powers is more adult than Dumb and Dumber.

• 36:31Speaker 02

  I think if you're nine, I think you're, I think you're ready.

• 36:34Ryan Holiday?

  Okay. You grew up in Sacramento, right?

• 36:36Speaker 02

  I did, yeah.

• 36:36Ryan Holiday?

  Where'd you grow up?

• 36:37Speaker 02

  I was so Carmichael and East Sac. So my dad lived in East Sac, mom lived in Carmichael.

• 36:42Ryan Holiday?

  Got it.

• 36:43Speaker 02

  Yeah, yeah. And you were, were you Granite Bay?

• 36:45Ryan Holiday?

  Well, in high school, I grew up in Fair Oaks. I was born in Gold River and then we moved to Fair Oaks and then we moved. My parents didn't want me to go to Bella Vista.

• 36:54Speaker 02

  Okay. Where'd you go to high school?

• 36:56Ryan Holiday?

  Granite Bay.

• 36:56Speaker 02

  Granite Bay. Okay. Yeah, yeah. All my friends went to Jesuit.

• 36:59Ryan Holiday?

  Yeah.

• 37:00Speaker 02

  Yeah, yeah.

• 37:00Ryan Holiday?

  I think my, my parents had some illusions of me going there and then like didn't do any work to make that happen. So then I just.

• 37:07Speaker 02

  Right. You had to go to.

• 37:09Ryan Holiday?

  You had to like do all these testing and stuff.

• 37:10Speaker 02

  Yeah. And you had to go to like Sunday school and stuff like that. Which I didn't grow up religious. So it was like, kind of like I was, my parents sent me to boarding school. So, but my dad was actually considering Granite Bay.

• 37:21Ryan Holiday?

  Yeah.

• 37:22Speaker 02

  He's like, should I move to Granite Bay to do Grant Bay or?

• 37:24Ryan Holiday?

  It was like the new, it's like, you know, when like they opened a new high school. It's like the best one.

• 37:29Speaker 02

  Yeah.

• 37:30Ryan Holiday?

  So like they just, I think they just opened it.

• 37:32Speaker 02

  Yeah.

• 37:32Ryan Holiday?

  And that's why they, yeah, they moved there. My grandfather, my mom's dad was a German teacher at Bella Vista.

• 37:39Speaker 02

  Oh, really?

• 37:39Ryan Holiday?

  So like, but for like 40 years. So I think there was like, no.

• 37:46Speaker 02

  Yeah. Sacramento. Yeah. It's a, it was a great place to grow up.

• 37:49Ryan Holiday?

  You thought so?

• 37:50Speaker 02

  You know what? I think, I went to a boarding school for high school.

• 37:53Ryan Holiday?

  Yeah. On the East Coast?

• 37:54Speaker 02

  Yeah. And I think, I think something about growing up in Sacramento is like, as opposed to other parts of California, like San Francisco, or if you grew up in LA, it's kind of, I think it, I think it grounded me a little bit more, just like kind of, it was a little bit, kind of away from the glamour of Hollywood or like San Francisco or something where it's, you're around more normal people, I would say.

• 38:18Ryan Holiday?

  Yeah, I see. I think that was the problem for me is that it was just normal people.

• 38:22Speaker 02

  Right.

• 38:23Ryan Holiday?

  Obviously, none of my parents' friends or my friends' parents were writers. But I don't think any of them were entrepreneurs. I think they all had jobs.

• 38:32Speaker 02

  Right.

• 38:32Ryan Holiday?

  Like, all had as normal a boring a job as you could imagine.

• 38:36Speaker 02

  Yeah.

• 38:36Ryan Holiday?

  And so if that's what you're meant to do, that's very comforting, I think. It is limiting in terms of like your sense of what's possible.

• 38:46Speaker 02

  Right.

• 38:47Ryan Holiday?

  You know what I mean?

• 38:48Speaker 02

  I haven't thought about that. Yeah, because I guess I went to, I was kind of like, went to boarding school.

• 38:52Ryan Holiday?

  Their parents probably did all sorts of incredible things.

• 38:54Speaker 02

  So I was, yeah, I was exposed to, you know, all that kind of stuff. So yeah, so that's an interesting point. Because I, to me, it was always sort of like having that foundation of Sacramento. And then kind of going into a world that's a little bit more glamorous and kind of, but yeah, I never really thought about that.

• 39:12Ryan Holiday?

  Well, like the nepo baby thing.

• 39:14Speaker 02

  Yeah.

• 39:14Ryan Holiday?

  People think it's that they opened doors, and I'm sure they did. And it's just like, if your parents are well off, like you're, you have more freedom to do things. But I think a big portion of it is like, your parents showed you that that was a thing you could do. That's the job. Like Steph Curry, growing up in basketball arenas.

• 39:31Speaker 02

  Yeah.

• 39:31Ryan Holiday?

  Probably contributed as much as the genetics did. He was like, this is the place you go to work. This is how it works. This is what you have to do to qualify for this line of work. You know what I mean? Like, like, I think if either of my parents had gone to private schools. They would have understood the process for getting your kid into a private school. Yeah, there's legacy admissions, but also just like, you know how that system works.

• 39:53Speaker 02

  Yes.

• 39:54Ryan Holiday?

  And so they didn't. They were just like, well, our kid's smart. Can he go here? And it's like, no, there was like a process you had to go through. Unless you're a genius. And they didn't go through the process, so they didn't get it. Like, knowing like the rules or the norms of spaces. That's, I think, that's like the real privilege that gets passed on it. To me, that's the nepo baby thing. It's like, you understand how the system works.

• 40:17Speaker 02

  Right. Yeah, so, yeah, because I remember when I, when I first moved to Hollywood to like pursue acting. My dad approached it, he's a doctor, so he approached it from the academic doctor. He's like. He's like, I want you to go J Crew, get some sweaters.

• 40:30Ryan Holiday?

  Yeah, yeah.

• 40:31Speaker 02

  Get a haircut.

• 40:32Ryan Holiday?

  Yes.

• 40:32Speaker 02

  Like, you're going in for a job interview.

• 40:34Ryan Holiday?

  Yeah.

• 40:35Speaker 02

  And then you realize, you know, very early on, it's like, no, if you were like quirky, you need to be quirky in order to like stand out.

• 40:41Ryan Holiday?

  Oh, it's so funny you said that because so I, so I went to Riverside.

• 40:44Speaker 02

  Yeah.

• 40:44Ryan Holiday?

  And because I was like, I want to, like, Southern California is where it's at. Even though Riverside could not be further, like, I might as well have just stayed in Sacramento.

• 40:53Speaker 02

  Yeah, yeah, yeah.

• 40:53Ryan Holiday?

  First off, the drive, one's an hour and a half drive and one's a five hour drive. Like, but I just thought like, Southern California, that's where it's at. And then I remember I got like through someone, I got like this interview for like a, an internship at a, like a record label. So I told my parents and they were like, same thing. They were like, here's our credit card, like, go buy a suit. And I bought a suit. I showed up to an interview at a record label in a suit.

• 41:17Speaker 02

  Yeah, yeah, yeah, yeah.

• 41:17Ryan Holiday?

  And it's like, I lost the job the second I stepped in, you know, like, you would have been like, hey, go buy these 50 albums and listen to them. Do you know, like, but to my parents, just like to your parents, not understanding the system, they're like, you gotta dress up? And then you gotta show up and have good answers to the questions. It's like, no, you're, you're actually precluding yourself from having the job by the way they're showing it. So it's like, it's understanding how the logic or the incentives of different systems work. That's like the real power.

• 41:47Speaker 02

  Yeah, and it's so, uh, so, yeah, cause the first year I was in LA, I was wearing button ups and wearing like, you know, kind of like preppy clothes and people are like, what are you, like, this isn't you. And I'm like, I'm like, and then it, once I like, I started doing stand up and it's, I started teaching surfing as like a day job. And, and I started to like, you know, get tan and kind of blonde streaks in my hair. And then people were kind of responding to that.

• 42:10Ryan Holiday?

  Yeah.

• 42:11Speaker 02

  It's like, oh, they're like, that's,

• 42:12Ryan Holiday?

  Yeah.

• 42:13Speaker 02

  that's who I should be, not this kind of like.

• 42:14Ryan Holiday?

  You gotta act like you, you've been here before.

• 42:16Speaker 02

  Exactly.

• 42:17Ryan Holiday?

  You're acting like, no one wants, you're acting, you're showing that you're a tourist.

• 42:22Speaker 02

  Yeah. And my, my dad was always like, starting off, he's like, he's like, you know, I really think you should try to get a job as a soap opera actor, cause it's, it's consistent, it's a day job. He's like, he's very focused on, it's very, you know, he's very, he's always thinking about our futures and like. Worried about it? He's like, he's like, this is like the most consistent thing. You could do this for 40 years and get a steady paycheck.

• 42:44Ryan Holiday?

  You may want to kill yourself, but.

• 42:46Speaker 02

  He's like, he's like, general hospital. That's, that's my dream.

• 42:49Ryan Holiday?

  Yeah, yeah.

• 42:50Speaker 02

  Yeah, that's so interesting. Yeah, it did take me a little bit because a while to embrace that. Like, no, you have to embrace your weirdness, especially in something like entertainment.

• 42:59Ryan Holiday?

  Yeah.

• 43:00Speaker 02

  You know, kind of lean into it.

• 43:02Ryan Holiday?

  We almost moved, when my parents were thinking of the Granite Bay thing, they were also, like, my dad got a job offer in Tahoe. And so they were thinking, and I think about like, I think I would have become Chad or JT if they did that. Do you know what I mean? Like, because we had some, I had a friend in Sacramento and Derek, around the same time.

• 43:20Speaker 02

  Yeah.

• 43:20Ryan Holiday?

  They moved to, you know, and like, I think about like what he's doing and how his brother, I'm like, oh, okay. This is actually like a huge, you probably don't want your kid to grow up in paradise.

• 43:31Speaker 02

  I thought about that too. My dad said he had like an offer to work in San Diego.

• 43:35Ryan Holiday?

  Yeah.

• 43:35Speaker 02

  And he also almost worked in Reading, but.

• 43:37Ryan Holiday?

  Not quite paradise.

• 43:38Speaker 02

  Not quite paradise, but San Diego.

• 43:40Ryan Holiday?

  Yeah.

• 43:40Speaker 02

  Growing up, I'd be like, wow.

• 43:41Ryan Holiday?

  Yeah.

• 43:42Speaker 02

  La Jolla, like, and he's like, I don't like it. It's cloudy. I'm like, what? But yeah, looking back on that, you know, it's, it does seem like a little bit of a hindrance because you grow up like, I feel like that, you know, it might create a lack of motivation.

• 43:56Ryan Holiday?

  You know, where you're just, I don't know, maybe it's who you're around or, yeah, it's, it's something, because it's funny you mention San Diego because I used to go like, why do we live in Sacramento?

• 44:05Speaker 02

  Yeah, same.

• 44:06Ryan Holiday?

  They're like, it's close to San Francisco, close to Tahoe. And I'm like, so it's, it's primary selling point is its proximity to two other better places?

• 44:15Speaker 02

  Yeah, it's like the parking lot.

• 44:17Ryan Holiday?

  Yeah, yeah, yeah. Because now they, like, they retired, they live in nice places. And I'm like, why did you live 50 years in a place that sucked? For hopefully 30 years in a place that doesn't?

• 44:29Speaker 02

  Yeah.

• 44:29Ryan Holiday?

  And so I'm like, San Diego, you could have just split the difference.

• 44:32Speaker 02

  Yeah.

• 44:32Ryan Holiday?

  But yeah, I think there's probably something good to grow up in like a normal, regular place, like.

• 44:37Speaker 02

  Yeah.

• 44:38Ryan Holiday?

  Kids who grow up in Manhattan, I'm like, what is your life like?

• 44:41Speaker 02

  Oh, yeah. I went to high school, kids who grew up in Manhattan. Yeah, it's, it's, but I like what you're saying too. It's like, there's, there's that mix of like, of like, having. Kind of sort of a grounded base that kind of keeps you humble. But also being exposed to, you know, people who actually, who really kind of.

• 44:55Ryan Holiday?

  You need to know it's possible.

• 44:57Speaker 02

  Yes.

• 44:57Ryan Holiday?

  And I think like, it wasn't until I went to college, actually, I just, I just got invited. I spoke at the college I went to. And like, so what happened was I got in and they sent us like in the summer before we started to this like seminar that was taught by this professor who was a novelist.

• 45:13Speaker 02

  Yeah.

• 45:13Ryan Holiday?

  And we had to like read her novel and we get the book and it's like a real book, like from a real, it says like, do your times best seller. Like it was a real. And I'm like, oh, this is a thing that people do. Like I, I loved reading, but like I had the same relationship to books as I did to movies. You know, in that like, I know they exist, but I have zero conception of how they get made and who gets to make them. It's like, like a rock star, like, yes, there's 20 people who get to do this, but it's not a thing that regular people can do. And like, I met this woman, her name is Susan Straight. Um, and she's a, like a sort of a California novelist. And it's like, oh, like you're a regular person and this is your job.

• 45:56Speaker 02

  Yeah.

• 45:57Ryan Holiday?

  I got more out of that in the college experience than any classes that I learned, like just the immediate exposure to how a whole field or like a world that I didn't know existed, existed.

• 46:11Speaker 02

  Yeah.

• 46:12Ryan Holiday?

  Which I've stayed in Sacramento would not have occurred.

• 46:14Speaker 02

  Totally. Yeah. I think, I think for, for me, it's, it's being exposed to the kind of people where you know it's possible. And, and for me, it's like, I knew nothing about Hollywood. I knew nothing about how movies, same thing, like movies get made. Like I, I wanted to shoot a sketch. I didn't understand really the lighting. He's like, we need to set up lighting. I was like, what?

• 46:31Ryan Holiday?

  Yeah.

• 46:32Speaker 02

  Like I didn't, you know, I had like a huge amount of naivete.

• 46:36Ryan Holiday?

  Yeah.

• 46:36Speaker 02

  But that, I think that served me well in, in the sense that like I was, I had seen people, been around people who had kind of, you know, followed their dreams. And so I was like, yeah, I could do that. Like there was something like, there's this weird confidence where like, I could totally do that. And then when you get in it, you kind of, I was like. You kind of learn everything, but I think that that kind of just having that knowing inside your head of like, oh, I could totally doing that. And there's just thrusting yourself into it.

• 47:01Ryan Holiday?

  Well, that's it. So obviously, my contention is that ego is generally bad.

• 47:05Speaker 02

  Yeah.

• 47:05Ryan Holiday?

  And it fucks people up.

• 47:07Speaker 02

  Yeah.

• 47:07Ryan Holiday?

  But you do see, especially in the arts, that ego, because it sometimes resembles confidence.

• 47:15Speaker 02

  Yeah.

• 47:15Ryan Holiday?

  Or because it ignores obvious dangers, or worst case scenarios, or like logic, or appropriateness, it sometimes is advantageous.

• 47:25Speaker 02

  Yeah.

• 47:25Ryan Holiday?

  So like, naivete can be helpful because like, you don't know, like, yeah, you, you just tried to do something, the odds were a trillion to one. But then there's also like the ego of like, yeah, I'm worthy of this, you know, like, yeah, like I, you should, you should give me millions of dollars to do this thing. Or yeah, like, I'm totally qualified to do this.

• 47:44Speaker 02

  Yeah.

• 47:45Ryan Holiday?

  And like, the ego, like, I've, I know this one author, I've known him a long time, and like, I think his superpower is he asks for stuff that he has zero business asking for. Do you know what I mean? Like, and he never feels uncomfortable about it. And I don't, I don't think he's like pushing through the discomfort.

• 48:05Speaker 02

  Yeah.

• 48:06Ryan Holiday?

  And I don't even know if it's like confidence. I think it's just more like, he's not even aware.

• 48:11Speaker 02

  Yeah.

• 48:12Ryan Holiday?

  That it's a thing that a normal person would be like, what?

• 48:18Speaker 02

  Yeah.

• 48:31Speaker 02

  I like in Ego's Enemy, you know, always be a student. I always try to remember that, just having that mindset of like, learning from people and always trying to get better and working on the craft. But yeah, I think there's kind of a mix of like that, always being a student, like that humility and that having that mindset, but also, yeah, just this, do you call it ego or something of just like, this kind of like, oh, yeah, but.

• 48:56Ryan Holiday?

  You're gonna go up to the head of a network and be like, you should give me a show.

• 49:00Speaker 02

  Yeah.

• 49:00Ryan Holiday?

  You know, and it's like, you can't do that. But it, sometimes it works for that. There's some people that it works for.

• 49:06Speaker 02

  Totally.

• 49:06Ryan Holiday?

  And then you're just like, fuck, wait, is that what I'm supposed to be doing?

• 49:08Speaker 02

  Yeah.

• 49:09Ryan Holiday?

  Or is that also that person's Achilles heel?

• 49:12Speaker 02

  Yeah. Yeah. I think it, there's probably more cases where it. Totally doesn't work. And then there's like, there's few unicorns where they're like, it just works out for them.

• 49:23Ryan Holiday?

  Yeah, they just walk through raindrops like their whole, every time they ask, they never hear no. They get the right person at the right time. They're just like, they just get stuff they have no business getting that other people had to work very hard to like earn. There's just a kind of like, um, yeah, it's like what they say, like, may you have the confidence of an average white man? You know, just, just like, just the world is my oyster.

• 49:45Speaker 02

  Yeah.

• 49:45Ryan Holiday?

  It's like, okay.

• 49:46Speaker 02

  Yeah. Do you think there's, do you think there's something to that mindset where like, it just, in the way you come off to people or something where it just creates scenarios where things tend to work out?

• 49:58Ryan Holiday?

  I think if you're not looking very closely, or you're not very informed.

• 50:02Speaker 02

  Yeah.

• 50:03Ryan Holiday?

  Like you're not savvy, ego and confidence look very similar.

• 50:06Speaker 02

  Right.

• 50:07Ryan Holiday?

  Like mania can look like charisma.

• 50:10Speaker 02

  Yeah.

• 50:11Ryan Holiday?

  But if you, so if you've never been around someone to be like, oh, this is what a crazy person does.

• 50:15Speaker 02

  Yeah.

• 50:16Ryan Holiday?

  You're like, I pumped around this guy. You don't realize like, it's gonna crash at some point.

• 50:20Speaker 02

  Yeah.

• 50:21Ryan Holiday?

  And I think, especially if you're not confident, that the confidence of egotistical or narcissistic, I mean, like you look at the first couple of people that I worked for, I was clearly searching for something, you know, like some daddy issues stuff.

• 50:38Speaker 02

  Yeah.

• 50:38Ryan Holiday?

  Um, and it's funny because I look at my, my sister, so it's like clearly something in the upbringing where like, we want to work. Most people see that kind of boss and run the other way. We're like, I love it here.

• 50:49Speaker 02

  Yeah.

• 50:49Ryan Holiday?

  This is normal, you know?

• 50:50Speaker 02

  Yeah, yeah, yeah.

• 50:51Ryan Holiday?

  But, uh, yeah, I think there's a lack of awareness. If it works for you until it doesn't work for you, and then you, then you tweet something and you're like, what? You know, what do you mean?

• 51:02Speaker 02

  Totally.

• 51:03Ryan Holiday?

  On a long enough timeline, it becomes a disadvantage. That's why I think you can confidently go like, ego's the enemy. But it clearly, I mean, there's obviously an extraordinary amount of very successful, very egotistical people.

• 51:17Speaker 02

  Yeah.

• 51:17Ryan Holiday?

  I just think it's, it's two things. One, like the myth of, was it Croesus? Where it's like, you can't, you gotta wait till the end till you judge a person happy. But I also. Also think unless you're really, really studying them closely, you're not seeing all the ways that they actually could have been more successful.

• 51:35Speaker 02

  Right.

• 51:36Ryan Holiday?

  So it's like, maybe, yeah, that person's ego makes them shameless enough to ask for stuff that they have no business doing. But by the same token, they tend not to do the work to then earn the thing because they think they're entitled.

• 51:47Speaker 02

  Like, you know what I mean?

• 51:49Ryan Holiday?

  Like, the confidence to get, like, it seems like confidence to be like, give me the shot, game's on the line.

• 51:54Speaker 02

  Yeah.

• 51:55Ryan Holiday?

  But like, actually, a great athlete is like, they know they have to do the work to earn that, you know?

• 52:02Speaker 02

  Yeah.

• 52:03Ryan Holiday?

  And if you're just like, no, no, give it to me, but you don't have the goods.

• 52:06Speaker 02

  Yeah.

• 52:06Ryan Holiday?

  Then you're gonna lose said game when it's on the line.

• 52:08Speaker 02

  Yeah, I see what you're saying. I think that's, yeah, it's the confidence to want to get the opportunity to put yourself in that position. Even when I was starting out, it was like, you know, there's these things called bringer shows for stand-up. Have you heard of that? Like, basically, you get stage time if you bring five friends. If you bring the audience, you get stage time. So early on, I like did like an open mic and I like, there's a bringer show that, yeah, we can give you stage at the, we can give you stage time at the Comedy Store. And I'm like, amazing.

• 52:39Ryan Holiday?

  Yeah.

• 52:39Speaker 02

  And, yeah, just bring five friends. So immediately I was like, I'm already on stage at the Comedy Store. This is crazy. And then I quickly, you know, wore out all my friends. I'm like, they were like, dude, we're not coming to any more shows. I'm like, oh, and like, it was this thing where I had like the naivete or to be like, no, I can be on stage at the Comedy Store. But then quickly learning of like, oh, no, it takes, what it really takes is two to three open mics a night.

• 53:07Ryan Holiday?

  Yeah.

• 53:07Speaker 02

  Every night for 10 years.

• 53:10Ryan Holiday?

  Yeah, you need a certain amount of shamelessness to get up and do the thing when you're bad, which you invariably are at the beginning.

• 53:17Speaker 02

  Yeah.

• 53:18Ryan Holiday?

  But you also need like this humility and maybe even the self-loathing.

• 53:22Speaker 02

  Yeah.

• 53:22Ryan Holiday?

  To like, Think that you're bad.

• 53:24Speaker 02

  Yes.

• 53:25Ryan Holiday?

  So you do the work to get good.

• 53:27Speaker 02

  Yeah.

• 53:27Ryan Holiday?

  Sometimes people will have just the confidence or the chutzpah to be like, I can fucking do this.

• 53:33Speaker 02

  Yeah.

• 53:34Ryan Holiday?

  And then they get up there and they so live in their own bubble that they're just bad, but they're not feeling the shame of being bad and then doing the work to get good. So you're, you just, that's how you stay shitty for a long period of time.

• 53:49Speaker 02

  And you see that a lot, like the people who will get off stage and be like, man, I crushed. And you're like, no, you didn't.

• 53:55Ryan Holiday?

  Yeah. If you walk off feeling that you crushed, it's like the best in the world don't feel that way.

• 53:59Speaker 02

  No.

• 54:00Ryan Holiday?

  So that you feel that way, that, so that's where ego is the enemy because it's, it's making you stay as you are. It's, it's probably more pleasant to not feel shitty.

• 54:11Speaker 02

  Yeah.

• 54:12Ryan Holiday?

  But the shitty is like, um, Ira Glass talks about this. He's like, there's a taste talent gap.

• 54:17Speaker 02

  Yeah.

• 54:17Ryan Holiday?

  When you start and you have good taste, which is you know what is funny or you know what's beautiful or you know what's good writing, but like you can't do it. But the desire to bridge that gap is like the propulsive force that makes you good. But if you're just like, maybe you have good taste, but then you're also biased when it comes to yourself or you're delusional when it comes to yourself, that's a problem because now you're just not, you're just like confidently being shitty. Like just because you believe you can do something, you're not going to be able to do it. But just because you believe you can do something is not even close to sufficient to being able to do it.

• 54:53Speaker 02

  Yeah. It's always having this kind of a, this mindset of like, no, there's always room for improvement.

• 54:57Ryan Holiday?

  Yeah.

• 54:58Speaker 02

  Like you're, you're never perfect. Always a student. Uh, that's one of my favorite things is just because like, you know, you, you'll see like Bill Burr get off the stage at the Comedy Store and he, to me, I'm like, he just crushed.

• 55:08Ryan Holiday?

  Yeah.

• 55:08Speaker 02

  But to him, he's like, ah, that one bit, like I, I'm not getting it right. You know, he's, there's that criticism. There's like self criticism of like, no, I need to improve this to really kinda, it's always perfecting it. It's kind of never reaching that destination. I think.

• 55:23Ryan Holiday?

  Well, Dr. Drew did a study many years ago of he, as guests would come in to Love Line, he gave them like this narcissistic personality test. Cause like, it's interesting, like you'd think you'd be able to study narcissism, but most really successful narcissists are obviously inaccessible to like clinical research, right? Most studies are done on like college students for class credit, you know?

• 55:48Speaker 02

  Yeah, yeah, yeah.

• 55:48Ryan Holiday?

  So he was able to give this narcissistic personality test to like all the guests. So like a range of celebrities and musicians and then also like reality TV stars and whatever. And what I remember from the study is that they found that, yeah, like most celebrities are, have some level of narcissism, but it's this interesting question of like, are narcissists attracted to celebrity or does celebrity make you narcissistic? It's probably a little of both, but one of the things they found was that the more technical the thing you did was, the less narcissistic you were. So like drummers might be very famous, cause they're in a huge band, but what they do is really fucking hard.

• 56:31Speaker 02

  Yeah.

• 56:31Ryan Holiday?

  And it's like a craft that you love. So it's like inherently humbling and it's inherently about like solving this like puzzle, you know? Versus like someone who was on the Real World Road Rules Challenge is like attractive, in good shape, made a good like pitch video.

• 56:50Speaker 02

  Yeah.

• 56:51Ryan Holiday?

  And then is maybe like dramatic. So like they, they're both famous, but one is getting their ass kicked by the craft of the thing.

• 57:04Speaker 02

  Yeah.

• 57:04Ryan Holiday?

  And the other one is mostly just thinking about like, how can I get more on TV?

• 57:08Speaker 02

  Yeah, it's like the craft itself humbles you.

• 57:11Ryan Holiday?

  Yeah.

• 57:11Speaker 02

  And keeps you in check.

• 57:12Ryan Holiday?

  Yeah.

• 57:13Speaker 02

  And uh, yeah, that makes, that makes a lot of sense.

• 57:16Ryan Holiday?

  I think to just be an actor and then become famous, obviously acting is a craft, but it's not a craft you get as many reps in as other things because it involves other people, right? But stand-up is like a thing you're going and doing every night and it's whether you're You're doing it for a thousand people or 10 people, it's fucking hard.

• 57:37Speaker 02

  And you get humbled by the audience.

• 57:39Ryan Holiday?

  Yeah.

• 57:39Speaker 02

  If you're not improving, if you're not constantly putting your A game forward, the, the audience will humble you.

• 57:44Ryan Holiday?

  Yeah.

• 57:44Speaker 02

  And I feel like for, for actors, if you're making your living as an actor, most of the time you're not acting.

• 57:50Ryan Holiday?

  Yes, that's what I mean.

• 57:51Speaker 02

  Yeah.

• 57:51Ryan Holiday?

  You're not getting that many reps.

• 57:52Speaker 02

  Yeah, you're, you're, you're acting, you know, maybe six months out of the year.

• 57:56Ryan Holiday?

  Yeah.

• 57:56Speaker 02

  And a lot of time it's just hurry up and wait. You're just sitting on set, so.

• 58:00Ryan Holiday?

  Like, how many movies is even a great director gonna do in their life?

• 58:04Speaker 02

  Yeah, I mean.

• 58:05Ryan Holiday?

  Five?

• 58:05Speaker 02

  Five.

• 58:06Ryan Holiday?

  You know, and, and a lot, so a lot of times you're not doing the thing. But you are, if you have succeeded, you're being the person, you're being the noun versus the verb.

• 58:15Speaker 02

  Right.

• 58:16Ryan Holiday?

  You're walking around, you're on panels, you're talking to classes. You know, you're negotiating contracts, but you're not like, fuck, how do we get this shot right?

• 58:25Speaker 02

  Yeah.

• 58:26Ryan Holiday?

  You know?

• 58:27Speaker 02

  It's more people asking you like, how do you, how do you come up with that?

• 58:30Ryan Holiday?

  Yes.

• 58:30Speaker 02

  How'd you come up with that shot? And you're like, oh, well, you know.

• 58:33Ryan Holiday?

  Yeah, I feel lucky because like my first book came out and did well. And then I wrote this, this, but the Stoic stuff that was much more gradual. And then I know people who like their first book had just like crushed. Now you're the person instead of like trying to be the person. You know, I spend a lot of time, a lot more time writing than being the writer. If you, if your first thing just, now you're the, you're the guy.

• 58:56Speaker 02

  Yeah.

• 58:56Ryan Holiday?

  The person who did the thing. And that I think can be destabilizing and disorienting.

• 59:01Speaker 02

  When you first started writing about Stoicism, was there like a lightbulb moment for you or?

• 59:06Ryan Holiday?

  Well, actually Dr. Drew introduced me to Stoicism.

• 59:08Speaker 02

  Really?

• 59:09Ryan Holiday?

  You didn't know this story?

• 59:10Speaker 02

  Oh, I didn't know that.

• 59:10Ryan Holiday?

  Oh, no, it's ridiculous. I was writing for the college newspaper in Riverside. And I got this call one day, no, I think they put like a slip in my, my mailbox at the, at the paper. Anyways, Trojan Condoms was sponsoring like a conference of college journalists. They were like, do you want to go? And I was like, fuck, yeah, you know? Uh, and so I went and he was the speaker and afterwards, because I used to listen to Love Line in my room every, every night before bed. And I was like, hey, you seem really smart. Like, what books would you like tell a kid like me to read? And he was reading the Stoics.

• 59:42Speaker 02

  Really?

• 59:42Ryan Holiday?

  That's how I got into. To it.

• 59:44Speaker 02

  Wow.

• 59:45Ryan Holiday?

  So I read this Stoics first, like I read, I was 20 and it sort of blew my mind. I was like, this is what I want to do and I want to write about. And I had a blog, like I started a blog the day I graduated from high school. So which I just realized is 20 years from like tomorrow.

• 1:00:00Speaker 02

  Oh, cool.

• 1:00:01Ryan Holiday?

  You know what? Like, so I've been doing this. I realized I've been doing this for 20 years now.

• 1:00:04Speaker 02

  Yeah, yeah.

• 1:00:05Ryan Holiday?

  But that's what I wanted to write about. And then I had this marketing career and I, I knew I wanted to write about that, but I, I understood at some level that no one was going to let a 20 year old write about ancient philosophy.

• 1:00:16Speaker 02

  Right.

• 1:00:17Ryan Holiday?

  So that's why I worked for Robert Greene. But I did the, I knew I had to do the other books first. And then I could write about what I wanted to if I, after you have a little bit of heat, then people are willing to take a shot on something crazy.

• 1:00:29Speaker 02

  Yeah. And you worked for, what did you do for Robert Greene?

• 1:00:32Ryan Holiday?

  I was his research assistant.

• 1:00:33Speaker 02

  Oh, you were? Okay.

• 1:00:34Ryan Holiday?

  For math, for the 50th law and mastery, and then a little bit on some of the other books.

• 1:00:39Speaker 02

  Yeah, he's awesome.

• 1:00:40Ryan Holiday?

  So I was maybe like 23 or 24 and I wrote this article about Stoicism. And this publisher found it and they were like, we'd like you to do a book about this. And I was like, Robert, like I have a book deal. What do you think? And he was like, no. And I was like, what do you mean? He's like, he was like really blunt. He was nice, but he was like, you have to say no to this. He was like, it's too early. You're not qualified to write this book. You'll be a better writer later. And I'm very glad I listened to him. But like, you think you're ready and you're probably not ready.

• 1:01:14Speaker 02

  It's similar in stand up. Like when you start, if you're getting laughs, a lot of times it's, it can be just the joke structure or whatever. And but you, as you keep doing it, you notice a difference in laughs and it's, and it's, you know, when I was like 24, I'm like, oh, I'm going to talk about partying in college. Cause like, you know, and you don't realize at the time that how much life experience informs like your relatability and like how much you can connect to an audience. Like, no, like most audiences, they don't want to hear from like a 23 year old or just.

• 1:01:44Ryan Holiday?

  That's exactly what Robert was saying.

• 1:01:45Speaker 02

  Yeah.

• 1:01:45Ryan Holiday?

  And, and like, you think these people are screwing you over by not giving you shots.

• 1:01:50Speaker 02

  Yeah.

• 1:01:51Ryan Holiday?

  You know, like you're like, if they would just let me do, I can do. I'm ready. And they're like, no, wait.

• 1:01:55Speaker 02

  Yeah.

• 1:01:56Ryan Holiday?

  You think you're being like help. Like, I remember on my first book. So I I hired a publicist for Trust Me, I'm Lying. I remember it was $20,000. I had to pay $20,000. And they were like, here's what you do. You make a list. The campaign we agreed to is I I picked $20,000 and I picked 20 outlets that I wanted to be on. The Daily Show, you know, CNN, I picked all the things, right?

• 1:02:17Speaker 02

  Yeah.

• 1:02:18Ryan Holiday?

  And like, that's what I was paying. There's obviously no guarantees, but that's. And they got zero of the things.

• 1:02:23Speaker 02

  Right.

• 1:02:24Ryan Holiday?

  Like, not one of the things.

• 1:02:25Speaker 02

  Yeah.

• 1:02:25Ryan Holiday?

  I have subsequently checked. I have subsequently gotten almost all the things on that list. Like, over the next 15 years, I did get all of those outlets. But I thought like, either they were not doing a good job, or like, these gatekeepers are like fucking me over.

• 1:02:42Speaker 02

  Yeah.

• 1:02:43Ryan Holiday?

  And like, if I had gotten any of those 20 things the first time, I feel like maybe my whole career would have turned out differently. Like, in a negative sense, because I I thought I was ready and I wasn't even close to being ready.

• 1:02:54Speaker 02

  Yeah.

• 1:02:55Ryan Holiday?

  There's this story I actually have in my, in the wisdom book about this like samurai master and the student comes to him and he goes like, I'd like to become a master. How long will it take? And he says, like, it'll take 10 years. And he goes, no, no, I'm very serious. I'll pay extra. Like, I'll work really hard. How long will it take? And he goes, 15 years. And then he goes, no, no, you don't understand. I don't have that much time. I'm I'm want to speed the process up. What do I have to do? And he goes, okay, it'll take 20 years.

• 1:03:24Speaker 02

  Yeah.

• 1:03:24Ryan Holiday?

  Right? And like, you think it, you think you want it to happen sooner or faster, and you almost certainly don't. And if you got the opportunities, not only are you not getting screwed over by not getting the opportunities early, you're probably being given a gift.

• 1:03:41Speaker 02

  Yeah, we kind of experienced that with, um, we got a show on Netflix.

• 1:03:45Ryan Holiday?

  Yeah.

• 1:03:45Speaker 02

  And it was great. The whole experience was great. And and but to me, it was like, actually, I was listening to Ego's Enemy a lot during it. Cause I'm like, I was like, gotta keep the ego in check. Like, don't become like too.

• 1:03:56Ryan Holiday?

  Yeah.

• 1:03:57Speaker 02

  And, you know, it kind of like, it was like the dream, especially growing up. It's like, if you're a comedian, like getting a TV show, you're like, that's the career maker. And to me, I was like, when this comes out. I'll, you know, I'll be cruise.

• 1:04:10Ryan Holiday?

  You're a made man.

• 1:04:11Speaker 02

  A made man, exactly. And like, the whole experience was awesome and, and we're really proud of how it came out. But it came out and next day it was, you know, you're kind of like, and nothing happened.

• 1:04:22Ryan Holiday?

  Where's the parade?

• 1:04:23Speaker 02

  Yeah, exactly.

• 1:04:24Ryan Holiday?

  Yeah, yeah.

• 1:04:25Speaker 02

  And I'm saying, I'm like, I was miserable for like two weeks where I was like, and, and my fiance was kind of like, what, what's your deal? You just expect everything to be easy from that point and to, and then, but it kind of humbled me in a sense to where I was like, I was like, oh, I just, I need to get back to that open mic mentality of just getting back to the craft and,

• 1:04:44Ryan Holiday?

  Yeah.

• 1:04:44Speaker 02

  and just putting the work in every day. Like there's, there's, there's never going to be a moment where you're kind of just on easy street.

• 1:04:50Ryan Holiday?

  Yeah, you think, cause you think for someone else, you're like, if they would just put this on the homepage of Netflix, it would blow up.

• 1:04:56Speaker 02

  Yeah.

• 1:04:56Ryan Holiday?

  And then everyone will, and you think you, that you think that's what you want.

• 1:05:00Speaker 02

  Yeah.

• 1:05:00Ryan Holiday?

  I remember once I read this thing from one of the founders of Google where they were saying like, early on, they knew that the algorithm was getting better every day.

• 1:05:09Speaker 02

  Right.

• 1:05:09Ryan Holiday?

  And so that actually, understanding that made them not feel anxious or slighted when they weren't getting press.

• 1:05:16Speaker 02

  Right.

• 1:05:16Ryan Holiday?

  Because they were like, every day later, the press comes, the better it will convert because the thing is better.

• 1:05:22Speaker 02

  Yeah.

• 1:05:23Ryan Holiday?

  Again, I'm like, I'm thinking, hey, I need to be like, this is my first book. It's about this thing. Why am I not on the Daily Show? Why am I not getting this thing? And it's like, first off, I would have almost certainly been an underwhelming guest.

• 1:05:34Speaker 02

  Yeah.

• 1:05:35Ryan Holiday?

  Because I'm 25 years old. I've never, like, I think for my first television appearance, I'm going to go into the fucking lion's den of like, one of the funny, you know, like, who am I to think I'm going to pull this off? Right? And then also, let's say I had, then however many hundreds of thousands of people are watching, some percentage of them are going to buy that book. And you know what they're going to think? This is a okay first book.

• 1:06:00Ryan Holiday?

  Like, I'm much happier that it happened. 10 years later.

• 1:06:05Speaker 02

  Mm hmm.

• 1:06:05Ryan Holiday?

  And I had gotten 10 years better at the thing.

• 1:06:09Speaker 02

  Mm hmm.

• 1:06:10Ryan Holiday?

  Obviously, this is contingent on you not quitting or, you know, like bouncing out like that. You have to have that sort of stick to itness. But yeah, the idea like to know like, no, I'm getting better every day. So actually, like, I don't need the attention right now.

• 1:06:24Speaker 02

  Mm hmm.

• 1:06:25Ryan Holiday?

  I'm just gonna keep doing the thing. It's probably a better. When people go, wait, isn't humility like a disadvantage? No, that's actually, it's actually kind of a confidence.

• 1:06:33Speaker 02

  Mm hmm.

• 1:06:34Ryan Holiday?

  Cause you're like, I'm not going anywhere. I'm getting better. I'm just gonna do this fucking thing. And like, yeah, if you're like, you get a show on Netflix and you're like, I made it. I'm amazing. That's like as good as you're gonna get.

• 1:06:44Speaker 02

  Yeah.

• 1:06:44Ryan Holiday?

  But if you're like, and I'm doing stand up tomorrow.

• 1:06:47Speaker 02

  Yeah.

• 1:06:47Ryan Holiday?

  Then you're gonna be that one, one rep better plus a TV show.

• 1:06:51Speaker 02

  Exactly. Yeah. And it's, it's, you think like, uh, I remember I was like, I was like, oh, I'm sure, you know, after this show comes out, we're gonna be playing theaters.

• 1:06:59Ryan Holiday?

  Yeah.

• 1:06:59Speaker 02

  Stand up, you know? And I'm so glad it didn't turn out that way because like, we didn't really tour before that. So it, you know, gave us the opportunity to tour, which is amazing, you know? But it's, you know, it's, it's clubs and it's, and you go from like stand up in LA to where you're doing like 10 minute sets. And, and it, you realize really early on that like, holding an audience for 30 to 40 minutes is something entirely different. And giving people a show is something entirely different than doing 10 minutes at the improv. I'm so grateful that it humbled me in a way to where it's like, it's like, oh, now I understand how to put on a show.

• 1:07:31Ryan Holiday?

  Yeah.

• 1:07:31Speaker 02

  Now I understand what I wanted. If I go on the road, if, if I'm playing to a crowd of people, I, I know what I want to give them. I, I now have the skills.

• 1:07:39Ryan Holiday?

  Yeah.

• 1:07:40Speaker 02

  To, you know, give them something to where they leave feeling satisfied.

• 1:07:45Ryan Holiday?

  Yeah.

• 1:07:46Speaker 02

  And if everything, and you'll, you'll see that too. People like early on, if like the industry is very hot on them, they're like, they're like, you, you're the next Chappelle. Like it kind of ruins their trajectory.

• 1:07:57Ryan Holiday?

  Totally. No, I think, um, one of the blessings and curses of social media is that it can just, it can skip all that.

• 1:08:04Speaker 02

  Mm hmm.

• 1:08:05Ryan Holiday?

  And so if you don't have the goods.

• 1:08:09Speaker 02

  Yeah.

• 1:08:09Ryan Holiday?

  You're not going to develop the goods. It's like if you decide to get into sports because you're really tall.

• 1:08:15Speaker 02

  Yeah.

• 1:08:15Ryan Holiday?

  Or you're just really strong or like, you're not going to develop the technique. You want to be, you want to be genetically gifted, but not so much so that you're used to coasting.

• 1:08:26Speaker 02

  Yeah.

• 1:08:26Ryan Holiday?

  Right? And so, yeah, you notice like, I, I notice this like with people who like, they have a big podcast and then like they'll sell a book. Or like a TV show, but it's like, it's not that podcasts are easy. It's just that you didn't start as a writer.

• 1:08:42Speaker 02

  Yep.

• 1:08:42Ryan Holiday?

  And so you just think that because you succeeded over here, that transfers over here. And it's like, no, this is a totally different medium. And that's, it's actually a much more demanding medium because you're doing all the work.

• 1:08:55Speaker 02

  Yep.

• 1:08:55Ryan Holiday?

  And so I'll notice it's like, oh, you have the goods to carry on an hour of conversation or even a three hour conversation.

• 1:09:02Speaker 02

  Yeah.

• 1:09:03Ryan Holiday?

  But you can't do a book that might take 20 hours to read. Like that's so much like.

• 1:09:08Speaker 02

  Yeah.

• 1:09:08Ryan Holiday?

  That's it. You just realize like people were blessed by the algorithm, but they were also cursed by the algorithm because they're not developing like the all around skills required to succeed in different mediums.

• 1:09:21Speaker 02

  Yeah. And you see it too, like in people nowadays are, I just keep citing like Bill Burr and Bargatze, but like they, they were, you know, in their thirties, they were in.

• 1:09:31Ryan Holiday?

  Comedy is interesting because it's one of the few that you actually do get the, like music, it's like, sure. But culture also favors you when you're young. So there's something raw and authentic about it. And then there's an expiration. It's like sports.

• 1:09:44Speaker 02

  Yeah.

• 1:09:45Ryan Holiday?

  Whereas like comedy, oftentimes the biggest comic in the world does have 10, 20, 30 years of experience. Because it's not as, it's not, it's not photogenic, but there's something not like where we, we were more generous with who we allow to succeed in the medium.

• 1:09:59Speaker 02

  Yeah.

• 1:10:00Ryan Holiday?

  And that's, so it's, that's a, it's a really good example of like, no, no, fucking do your act. Get really good at it. That's how you succeed. Not like these tricks and whatever. I'm being maybe a little bit dismissive of social media too, where it's like, you also see people who are like, I. See this where like, there's people who know more about philosophy or know more about like the technical stuff, or maybe they're even better writers. And then, and then they think like, the social media stuff is easy.

• 1:10:26Speaker 02

  Right.

• 1:10:27Ryan Holiday?

  Right? And it's like, I don't think you actually understand how hard it is. Take a complex philosophical lesson and make it accessible to millions of people. Because most people not only aren't interested, they're anti-interested. Do you know what I mean?

• 1:10:41Speaker 02

  Yeah, yeah, yeah.

• 1:10:41Ryan Holiday?

  Like, it's not like they were dying. Like, people are like, oh, he's a popularizer or something. And it's like, people weren't dying for me to do this.

• 1:10:49Speaker 02

  Right.

• 1:10:49Ryan Holiday?

  You know what I mean?

• 1:10:50Speaker 02

  Yeah.

• 1:10:50Ryan Holiday?

  They had stereotypes, preconceived notions of how they were not. Like, there's a headwind.

• 1:10:55Speaker 02

  Yeah.

• 1:10:55Ryan Holiday?

  And so, yeah, it's like, that's where ego's the problem. Like, the Midas touch is a cautionary tale. Like, if you think you have the golden touch, you're gonna fuck shit up because you're not gonna do the work.

• 1:11:05Speaker 02

  Yeah.

• 1:11:06Ryan Holiday?

  To be careful about the other thing.

• 1:11:08Speaker 02

  Totally. And it's, there's also conversely with social media, there's people who will come along and be like, I know the tricks of the algorithm. Like, here's like how, you know, here's how you hook the audience. And so, and then so people who are trying to like, make it big on social media, they'll, you know, they'll create kind of trash content because they're like, oh, this will get views. And it, but they're

• 1:11:28Ryan Holiday?

  They're garbage views.

• 1:11:29Speaker 02

  Garbage views. They might get the views, but there's no substance to like, whatever following that creates to where it's

• 1:11:36Ryan Holiday?

  There's no actual relationship because there's nothing there.

• 1:11:38Speaker 02

  Yeah, that you're not creating, like, if you're trying to create fans, you're not creating true fandom, because it's just, uh, yeah. So I think it's having that realization that in every, there's no, there's no, you know, free parking or, you know.

• 1:11:53Ryan Holiday?

  Well, I bet you, like, the viral city council meeting stuff.

• 1:11:57Speaker 02

  Yeah.

• 1:11:57Ryan Holiday?

  Probably does the best.

• 1:11:59Speaker 02

  Yeah.

• 1:11:59Ryan Holiday?

  But like, who goes and sees that person?

• 1:12:02Speaker 02

  Yes.

• 1:12:02Ryan Holiday?

  In a, in a theater, because like, it's not a city council meeting.

• 1:12:05Speaker 02

  Exactly.

• 1:12:06Ryan Holiday?

  So you have to, you're like, would I rather have the city council thing do 10 million views?

• 1:12:10Speaker 02

  Yeah.

• 1:12:11Ryan Holiday?

  Or this like, funny sketch or bit that I came up with to 100,000 views?

• 1:12:15Speaker 02

  Mm hmm.

• 1:12:16Ryan Holiday?

  One is much smaller, but probably much actually better for you.

• 1:12:19Speaker 02

  Yeah.

• 1:12:19Ryan Holiday?

  Because the goal isn't just to have a large number of numbers.

• 1:12:24Speaker 02

  Yeah.

• 1:12:24Ryan Holiday?

  Next to your account. It's to have fans.

• 1:12:27Speaker 02

  Yeah, oh yeah, I learned that too. It's like virality does not translate to, you know, a career in the sense of like, of like, yeah, you need to, yeah, creating a relationship with the fans or like getting that like, people go to see certain comics because they love their stand-up.

• 1:12:46Ryan Holiday?

  Yeah.

• 1:12:46Speaker 02

  And so it's not like just by being, a lot of times too, sometimes people will become popular and then they'll get people to come out.

• 1:12:54Ryan Holiday?

  Yeah.

• 1:12:54Speaker 02

  But they don't have the goods and then they just ruin that.

• 1:12:57Ryan Holiday?

  Yeah.

• 1:12:58Speaker 02

  And it's, yeah, it's like, so it's, it's understanding that there's, you gotta work hard at everything.

• 1:13:05Ryan Holiday?

  Yes.

• 1:13:05Speaker 02

  And were there any other notable figures in culture kind of talking about philosophy in the way that you were?

• 1:13:13Ryan Holiday?

  That's a good question. I don't know. I mean, this was definitely, I started writing in 2000, I started writing about Stoicism in like, 2007 and eight, so like well before even social media and well before influencers. So that wasn't really the model. That came later, like in the eighties, there were some authors that did books about like Machiavelli, or did books about Genghis Khan or the Art of War that popularized them like to Wall Street.

• 1:13:41Speaker 02

  Right.

• 1:13:41Ryan Holiday?

  And I'd read about that. I was like, oh, that's interesting. They were able to like take this thing and make it popular to people who were trying to use it in a different sphere.

• 1:13:49Speaker 02

  Yeah.

• 1:13:50Ryan Holiday?

  And then obviously I knew Robert Greene and Robert's sort of a model for that too. So I had some sense that you could take something that was esoteric or impractical and make it accessible to people. So I had that. And then, I think people always think there's some plan, you know, they're like, you know, like, how'd you know? It's like, I was actually writing about marketing books. And then I wrote about like, the order didn't exactly happen in the way people thought it did, right? I also had a day job, so it kind of like, none of it really mattered, you know? But then you add, it wasn't like, I was like, okay, I'm gonna do this and then this and then this and then it'll end here. It's more like, I'm doing this thing that I really like and then I'm looking at other people. It's like, oh, like here's, here's Instagram. Well, like people post quotes.

• 1:14:35Ryan Holiday?

  It's do that. And then I was like, we noticed. Like, for instance, we would post like the quotes and then I'd be like, I have a new book out. And then they'd be like, who? Who are you?

• 1:14:44Speaker 02

  Yeah.

• 1:14:45Ryan Holiday?

  And I was like, oh, they're following the account for the quotes.

• 1:14:47Speaker 02

  Right.

• 1:14:48Ryan Holiday?

  Know that that's, I'm doing it. And so part of the videos and the other stuff came from like needing to make the connection between stoicism and me, that sort of translator, popularizer of it, right?

• 1:15:02Speaker 02

  Yeah.

• 1:15:03Ryan Holiday?

  It's kind of, you make these individual decisions as you go. And then later, people are like, well, this was obviously the plan.

• 1:15:08Speaker 02

  Right.

• 1:15:09Ryan Holiday?

  And you're like, no, I was just going from cool thing to cool thing.

• 1:15:13Speaker 02

  Yeah, that's cool. Yeah, it's, um, I remember when I first read, because when you first came on our podcast, the book was Stillness is the Key. And so I read it and-

• 1:15:22Ryan Holiday?

  Why did you guys even have me? Did you know who I was? Or was it just, you like, thought it was a funny pitch?

• 1:15:28Speaker 02

  You know, uh, JT's girlfriend at the time?

• 1:15:30Ryan Holiday?

  Yeah.

• 1:15:31Speaker 02

  My co-host. Uh, we got an email, I think, for you, uh, from your publicist. And, uh, his girlfriend at the time was like, oh, I love his books. He just have them on.

• 1:15:39Ryan Holiday?

  Hilarious.

• 1:15:39Speaker 02

  Yeah, yeah. And, um, but then I like, I, I read the book and I studied philosophy and I love it. And so it's just like what I love to read about the most. And I think the way you were able to deliver it in like a way that's just, you know, sometimes you read these philosophy books, they're so dense. You're like, I was reading like Nietzsche. I'm like, what is going on?

• 1:15:59Ryan Holiday?

  Yeah, exactly.

• 1:16:00Speaker 02

  It's like, it takes like so long to get through a page and understand what you're reading.

• 1:16:04Ryan Holiday?

  And then you're like, is this actually good? Or is someone just telling me that it's good?

• 1:16:09Speaker 02

  Right.

• 1:16:09Ryan Holiday?

  Like, I don't know.

• 1:16:10Speaker 02

  Yeah. I even reread Meditations during COVID. And, uh, even that, you know, it's, you really got to take your time. And, um, so it was such a cool thing, you know, stumbling upon your work.

• 1:16:22Ryan Holiday?

  Likewise.

• 1:16:23Speaker 02

  Yeah. Oh, thanks. Yeah, yeah. It was a great meeting of the minds.

• 1:16:26Ryan Holiday?

  Yeah.

• 1:16:29Ryan Holiday?

  You want to go check out some books?

• 1:16:30Speaker 02

  Yeah.

• 1:16:36Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it and I'll see you next episode.