A Stoic Masterclass for Ambitious People | Codie Sanchez

Ambition can open doors, but your principles determine where you go from there. In today’s episode, Ryan talks with entrepreneur and investor Codie Sanchez https://www.instagram.com/codiesanchez/?hl=en about how the four Stoic virtues of courage, discipline, justice, and wisdom can serve as a guide for building a successful career, leading well, and creating a life you actually want. They discuss why most professional risks are less dangerous than they seem, how to stop undervaluing your work, and what it means to pursue success without sacrificing your values, relationships, or reputation. Codie Sanchez https://www.instagram.com/codiesanchez/?hl=en is an entrepreneur, investor, and founder of Contrarian Thinking https://www.contrarianthinking.co/, where she teaches people how to build wealth through business ownership. After starting her career in journalism and later working in finance at firms like Goldman Sachs and Vanguard, Codie went on to buy, build, and invest in Main Street businesses. She is also the author of Main Street Millionaire https://www.thepaintedporch.com/products/main-street-millionaire-how-to-make-extraordinary-wealth-buying-ordinary-businesses?_pos=1&_sid=c81c995fb&_ss=r and host of the BigDeal Podcast https://podcasts.apple.com/us/podcast/how-to-build-self-discipline-5-step-routine-ryan-holiday/id1736593333?i=1000743293433. Follow Codie Sanchez on Instagram @codiesanchez https://www.instagram.com/codiesanchez/?hl=en, onTikTok @Codie_Sanche https://www.tiktok.com/@realcodiesanchezz, and on YouTube @CodieSanchezCT https://www.youtube.com/@CodieSanchezCT Check out Ryan’s episode on BigDeal by Codie Sanchez https://podcasts.apple.com/us/podcast/how-to-build-self-discipline-5-step-routine-ryan-holiday/id1736593333?i=1000743293433 👉 Apple Podcasts https://podcasts.apple.com/us/podcast/how-to-build-self-discipline-5-step-routine-ryan-holiday/id1736593333?i=1000743293433, Spotify https://open.spotify.com/episode/5cM8ovLGeTWHVzx7XW8GhJ, YouTube https://www.youtube.com/watch?v=aBJu95bVYAA 📚 Grab signed copies of Main Street Millionaire by Codie Sanchez https://www.thepaintedporch.com/products/main-street-millionaire-how-to-make-extraordinary-wealth-buying-ordinary-businesses?_pos=1&_sid=c81c995fb&_ss=r at The Painted Porch | https://www.thepaintedporch.com/ https://www.thepaintedporch.com/products/main-street-millionaire-how-to-make-extraordinary-wealth-buying-ordinary-businesses?_pos=1&_sid=c81c995fb&_ss=r 🎟️DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/ 🎙️AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing toThe Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content:https://dailystoic.supercast.com/ 🎥 VIDEO EPISODES https://www.youtube.com/@DailyStoic/videos| Watch the video episodes onThe Daily Stoic YouTube channel https://www.youtube.com/@DailyStoic/videos:https://www.youtube.com/@DailyStoic/videos ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://dailystoic.com/dailyemail 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.

• 0:00Ryan Holiday?

  Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world.

• 0:15Ryan Holiday?

  I think people think that like having your own business or being an entrepreneur, being your own boss, is a way to freedom, maybe even like a shortcut to freedom. You're sort of breaking off the shackles of employment or corporate life, and now you're truly free. You can do anything you want. And there's some truth to that. It is nice to be your own boss. It is nice to have your own business. It's nice to be successful. But one of the things you find is that actually this presents you with a lot of choices, a lot of responsibilities, unless you're a sociopath, some obligations and duties. That's been one of the challenges of having Daily Stoic over the years, right? Like suddenly, these choices are mine.

• 0:58Ryan Holiday?

  It's not what the board decides. It's not what standard practices decides. It's not what tradition decides. It's not what my manager or his manager or her manager or the manager above there. It's not what they decide. It's not even some like industry association or regulatory body. Like, these are all my choices. And that's really empowering and fun in a lot of ways. And it's also challenging and exhausting in a lot of ways. And that's, that's one of the things I wanted to talk about in today's episode, like how we think about business and entrepreneurship in an ethical framework and how we think about it as far as

• 1:43Ryan Holiday?

  an opportunity to practice virtue. Right? I think the Stoics would have found business really interesting. I mean, Xeno was a merchant, but I think they would have found our business world, our economic system really interesting. Certainly, they wouldn't have thought it as some special sphere outside of the four virtues, courage, discipline, justice, wisdom. Like, they thought that those virtues were designed to be applied to whatever it is that you did, whether you were a soldier or an emperor and olive oil merchant. That's what we're going to talk about in today's episode. Codie Sanchez, who lives here in Austin. She's an entrepreneur and an investor. She wrote a book, actually with my same publisher called Main Street Millionaire.

• 2:25Ryan Holiday?

  And she built this really interesting career and platform around buying businesses, usually kind of like small businesses, Main Street businesses, not like private equity in the, let's buy a big company and sell it for parts, but actually let's buy a bunch of little businesses in a town and turn them into something, build a portfolio of businesses that do real things for, for real people. And that's what we talked about today. We actually just go through all the four virtues and how they apply. As I said, Cody is a entrepreneur, an investor. You've probably seen her YouTube videos, Cody Sanchez C T, maybe on Tik Tok, Cody

• 3:09Ryan Holiday?

  underscore Sanchez, or on Instagram, at Cody Sanchez. She previously worked at Goldman Sachs and Vanguard. And now she buys and sells and invests in businesses and makes a lot of really interesting content. I was on her podcast a couple of months back. You can listen to that. But here's Cody and I talking about courage and discipline and justice and wisdom. Okay. So what I, what I thought we could talk about, so the, the four virtues of Stoicism are courage, discipline, or self-discipline, justice and wisdom. It strikes me that those are also good business virtues. You could say it's a cheat code for being an entrepreneur or a leader or a business person. So I thought we could maybe sort of run through how you think each one applies or, and what, how you understand them or what you understand them to me.

• 3:54Ryan Holiday?

  So let's start with courage, because you said, you said you didn't know if you could do some of this stuff earlier. That, that is the, the scary part of walking away from something safe or diverging from the conventional path. It's not physical courage normally, but it is what we would call moral courage.

• 4:11Speaker 01

  Yeah, well, I think entrepreneurship is probably one of the scariest things a human can do because you wrap your identity in who you are as a businessperson, as an entrepreneur, an author. And so when that gets rejected, you feel like you are rejected yourself.

• 4:25Ryan Holiday?

  Yeah.

• 4:26Speaker 01

  At least if you're not totally self-realized and your ego's completely eviscerated. And so I think that business is a really beautiful way to get better at life. I probably would not be as good of a person as I am today, although I'm still on the climb. But like, in any way, shape or form, I wouldn't be where I am if I hadn't done really hard things in business because it teaches you to keep doing hard things, that you get rewarded for it.

• 4:49Ryan Holiday?

  That you're a person who does hard things.

• 4:51Speaker 01

  Yeah, exactly. Identity shift as a person who does hard things. So, yeah, I mean, I always joke with my husband, too, because there's levels to this game of courage.

• 4:58Ryan Holiday?

  Yeah.

• 4:58Speaker 01

  You know, he's a former Navy SEAL and military man. So when I say things like, "We're gonna go to war," he's like, "You're literally not. You know, you give business advice. You're okay. Everybody's gonna be fine, more or less."

• 5:08Ryan Holiday?

  And by the way, that is a really important thing. Like, it can feel so scary. You're like, I remember when I dropped out of college, I was like, "I'm really taking my life in my hands." And it's like, "No, I'm not. Like, not at all." It seemed so scary, and it seemed so scary to my parents, who like, lost their minds about it. What you're taking for granted is, one, how privileged you are. So like, even if you totally failed, you're not ending up here, you're ending up here. And then also, like, actually, it's one of the, you just would go back to school. It's so easy. Like, you're like, "I'm gonna quit my job and start a business." And you're like, "But what if I fail?" Then you would just go get another job.

• 5:46Speaker 01

  Which is where you all are already.

• 5:48Ryan Holiday?

  Yes.

• 5:48Speaker 01

  Yeah, we call these one-way doors versus two-way doors. And in life, most things are two-way doors. They swing both ways. You can go in or out.

• 5:56Ryan Holiday?

  Right.

• 5:56Speaker 01

  You know, maybe a one-way door to decide to go swim with great white sharks without a cage.

• 6:01Ryan Holiday?

  Yeah.

• 6:01Speaker 01

  One-way door, right? Everything we do in business, mostly two-way doors. And so, a lot of times in our meetings, like, you'll sit down and go, "Is this a one-way door or a two-way door?

• 6:08Ryan Holiday?

  Yes.

• 6:08Speaker 01

  Could this kill us? And by kill us in business, make us go bankrupt, lose all our money, lose our reputational risk. That would be bad.

• 6:14Ryan Holiday?

  Right.

• 6:14Speaker 01

  But I think you're right. I mean, one of the things that breaks my heart for young people today, that for some reason, we got lucky, I got lucky, and we realize. But for young people today, I think that they have, they have like, contextual risk that they don't fully understand. Meaning... When you're young, you're like, well, I went to this school. They went to this school. We're on the same level. I got a job paying 100K. They got a job paying 100K. We're on the same level. All my friends have jobs paying 100K. So we're on the same level. Now, if I go and do a startup, that's still at the same level because it's perceived as cool right now. But if I fail and lose all my money and raise no capital and have to go bag groceries or become a barista, I have lost my contextual success versus my friends.

• 6:59Ryan Holiday?

  Right.

• 7:00Speaker 01

  And so now I'm a worse person and I'm spiraling and I've lost my place in the world. In reality, you know, we just hired a guy. He's my new chief of staff and he's incredible. His name is Mikey. And Mikey had to come from Iraq, where he was a translator, to the US. He worked with Chris. So when Chris got him out of Iraq, he came to the US. He bagged groceries and went to Starbucks, although he speaks like five languages. He's an engineer. He's a young man. And then the second that he got his citizenship, he went and signed up for the Marines, became first in his class. Then he went and got his grad school degree, whatever. But when I asked him, I said, you know, you're going to go, you're an engineer. Now you're going to come be a chief of staff. How do you feel about that change? Do you feel like that there will be contextual change?

• 7:44Speaker 01

  And he said, no. He's like, I bagged groceries because it would help me. I don't, my ego doesn't care about that as long as I'm progressing. And I think we've lost that a little bit, like young people today. I wish they could remember that like, none of that matters in the early stages of the race.

• 7:59Ryan Holiday?

  Yes.

• 7:59Speaker 01

  You know, maybe later it could be real risk.

• 8:02Ryan Holiday?

  Well, and what you're not thinking about is how many people would kill even to be in the failed position that you're worried about being a step down. And so, yes, obviously a physical danger is very scary, but we get in our heads about these reputational dangers. Or, you know, like you're not going to starve to death. Okay. And, and so you have this perception of the, the risk that you're taking. And it's actually not based on, on anything real.

• 8:33Speaker 01

  No, it's not. And, you know, it is always fun to say like the what if game. Like sometimes when I'm really scared in the beginning, like when I first started a business. I wrote down all the things that could go terribly wrong because I was really scared that I might leave Goldman Sachs and State Street and all these big jobs and go do this little thing and it would be a failure and then for some reason they would never hire me again. And I had these totally irrational what ifs all the way down. And then I wrote them down and just next to them, I wrote, is this reasonable?

• 8:59Ryan Holiday?

  Yeah.

• 9:00Speaker 01

  That was it. And I would say of those, I wish I still had the list, but of those, probably 90% of them were completely unreasonable. And when I asked that question, like, well, I fail and then I can't go back and get this job in finance. And I said, well, maybe that is true. Maybe that's not unreasonable. So then I asked my boss, hey, if this fails in a year, can I come back?

• 9:17Ryan Holiday?

  Yeah.

• 9:18Speaker 01

  And he was like, yeah, sure.

• 9:19Ryan Holiday?

  Yes.

• 9:19Speaker 01

  Pick your role. So at that point, you're like, huh, how much of the things that I'm scared are going to happen are basically just ghosts in the mind.

• 9:26Ryan Holiday?

  Well, do you know the acronym for fear?

• 9:28Speaker 01

  No.

• 9:28Ryan Holiday?

  They talk about in recovery, it's false evidence appearing real.

• 9:32Speaker 01

  That's true.

• 9:32Ryan Holiday?

  And so, so the idea of going, okay, what is the worst case scenario here? Like, what, because, because what happens, we have these kind of vague fears, like, hey, I'm going to end up under a bridge somewhere, everyone will laugh at me, I'm going to be broke. And then, and then what you do is, yeah, you write it down, or you think about it, and then you go, okay, is this actually true? And what would it look like if that would happen? And how recoverable is it if that happens? And you find out that, oh, I have this kind of vague sense of catastrophe in my mind. But then, yeah, as you said, you go to your boss and you go, hey, if this doesn't work out, can I come back? And they're like, yeah, right? And, and so I think people tend to think of entrepreneurs as, as just plunging into the unknown, not caring about the risk. But actually, what happened is

• 10:16Ryan Holiday?

  they thought about the risk and they realized the risk is not that high. Like, a lot of entrepreneurs, I think, or investors, people don't think about it. They go like, okay, the worst thing that can happen is I'm losing the money that I put in, right? Like, there are some sort of forms of investing that are really scary, where you can lose like effectively an infinite amount of money. But like, if you put in $50,000 to do X, Y, or Z, yes, $50,000 is a lot of money and it can be painful for that to go away. But you, you can't lose more than you put in. So you go, oh, actually, the downside risk here is capped at what I'm doing. I'm betting a year of my life on this thing. Yes, it could end up being a total waste of time. But so, I just a year behind my peers. Is

• 10:59Ryan Holiday?

  that so bad? I remember when I was thinking about dropping out of college, my boss, who I was going to go work for, was like, I was like, yeah, what if this doesn't work out? And I, you know, I have to go back to school. And he was like, I spent a year in the hospital. Basically, I missed a year of school being sick. And he was like, it has never once come up. Like, no one has ever once said, hey, I noticed that it took five years for you to get your degree. They're not even doing the math. Like, and he's like, by the way, I haven't given anyone a resume in two decades. Like, nobody, nobody knows. They, they might ask where I went to school because it's cool for us to talk about. Turns out, we both went to this college or that college. But like, no one is, no one is concerned that you are one year behind someone else because you took a risk on something.

• 11:43Ryan Holiday?

  And by the way, we're not even getting into the upside of you took that risk and the whole trajectory of your life went in an awesome direction.

• 11:50Speaker 01

  Yeah. I mean, I've always found that when you are obsessing on the things that are going to hold you back in life, you just go back to the spotlight theory, right? And realize that we all imagine that we're on this stage and there's a spotlight on top of us. And every single thing that we do, everyone else is watching and judging. And none of them are clapping ever, but they're all, all thinking bad things mostly. And then you realize, in fact, you know, it's more like, uh, everybody in the world has their own spotlight. So they literally can't even see you because they're so busy looking at themselves. And that helps me a lot when I think people care about me and I remember they don't.

• 12:22Ryan Holiday?

  Well, that's the problem with imposter syndrome, right? And it is presuming way too much interest in you. Like, no, no one is, no one is concerned that you're an imposter. They're, they're quite concerned that they are an imposter. And all the people that you admire had the same thoughts. There's a famous story where Marx really is, right before he becomes the emperor of Rome, he supposedly breaks down in tears, like he doesn't think he can do this. And that night he has this dream and in the dream he has shoulders of ivory. And he realizes, oh, actually I am strong enough to like bear this load. And, and to me, that's like, uh, like an ancient story about imposter syndrome, which is like, you don't think you can do it. And by the way, everyone who has ever done it didn't think they could do it either.

• 13:04Ryan Holiday?

  And if you go into it thinking that you can do it, that you're destined for this, that it's guaranteed, that it's going to be easy, like, uh, you're probably heading, like, that's, those are all bad signs. Like, a boxer who steps into the ring and is not nervous is going to get destroyed because it means you have underestimated your opponent and overestimated your abilities.

• 13:24Speaker 01

  Yeah. You know, the other side of that is if like, I think sometimes, at least when I would listen to this back in the day and I was still scared and stayed in corporate, let's say forever. I also thought about like, what's the ways to do this with less risk?

• 13:38Ryan Holiday?

  Yes.

• 13:38Speaker 01

  Like, okay, these days I do think that we sort of idolize the people who just jump off the bridge.

• 13:43Ryan Holiday?

  Yeah.

• 13:44Speaker 01

  And somehow figure out how to build the airplane on the way down.

• 13:46Ryan Holiday?

  Yeah.

• 13:46Speaker 01

  And the truth of the matter is, most people don't figure out how to build the airplane on the way down. Most businesses fail.

• 13:51Ryan Holiday?

  Yeah.

• 13:51Speaker 01

  And like, that is totally possible for it to happen. And so I think we also have to, like, it is perfectly okay if you work in a business and you make a ton of money in somebody else's company.

• 14:03Ryan Holiday?

  Yeah.

• 14:03Speaker 01

  And you make a ton of money in somebody else's company and you keep growing. You know, I was thinking about this today. Like Goldman Sachs, I used to work there back in the day. Guess how that got started? Two gentlemen who were actually basically glorified loan brokers. They weren't anybody special. They started that business. Now, since then, that business is huge. But how many people who run the world were only ever employees at Goldman Sachs?

• 14:27Ryan Holiday?

  Yeah.

• 14:27Speaker 01

  The number's like 10.

• 14:29Ryan Holiday?

  Right.

• 14:29Speaker 01

  You know, you have, you have Blank Fine, you have Bernanke, you have members, like, members of the Fed, also members of the government across the board. Are those people any less powerful and rich because they were never an entrepreneur?

• 14:41Ryan Holiday?

  Right.

• 14:41Speaker 01

  Of course not. And so it's the same thing. I mean, whether you like the politics one way or the other, but I go back to like Bain. Bain is fascinating because Bain was a consulting company, started from one gent, right, who just gave advice, not dissimilar to you and I. And then he goes, no, I'm just going to scale given advice. I'm going to do it again and again. Then he goes to Mitt Romney and says, hey, by the way, why don't you start up a capital division for us? And if it fails, it's fine. Just come back to the business. Otherwise, I'll fund it and you build it. And that became so big that Mitt Romney, you know, ran for president.

• 15:13Ryan Holiday?

  Yeah.

• 15:13Speaker 01

  And I'd walk by his like $80 million house all the time when I'm in San Diego. It was ludicrous. And they were entrepreneurs. And so as much as I want people to go buy businesses, and I love that people buy businesses and they save small businesses, you can also go make a ton of money working for somebody else and have a life you love and take huge risk doing it, too.

• 15:32Ryan Holiday?

  And then the transition to doing your next thing also doesn't have to be you blow up your life, right? There's a story about Cortez burning the boats behind him. It doesn't have to go that way. And oftentimes, it doesn't go that way.

• 15:42Speaker 01

  Exactly.

• 15:43Ryan Holiday?

  I remember when I decided to To leave my corporate job to be a writer, I was ready to do that. Like, I decided, hey, this has gone on long enough. If I don't do it, I'm never going to do it. So I'm going to do it. And I went and I called my boss and I said, hey, I'm going to leave to be a writer. I'm going to move this book idea. And they're like, hey, that sounds awesome, but we're not ready to lose you. So what if you went and did that? And then you just also kept doing your job? And I was like, oh, I didn't even think that that was possible. So oftentimes, we think like it's incompatible in entrepreneurial life and then a corporate life or a salaried life. And actually, if you're really good at what you do, oftentimes you'll have enough leverage.

• 16:25Ryan Holiday?

  Or you can work out a compromise and you can do both. And I wrote my first three books while I was also collecting a paycheck. And then what that allowed me to do actually was take much more risks creatively. So when I went to my, my first book was about marketing. So there was a sort of an overlap between my corporate life and my, my writing. But then when I went to my publisher and I said, hey, I want to write about an obscure school of ancient philosophy, they were like, uh, well, that's not really worth very much to us. And so they were like, here's, here's the most we would pay. And I was like, cool, I don't care. This book money is, is, is like a side hustle for me. I just want to do this. And so oftentimes, not only should you not jump off the cliff and try to figure out

• 17:07Ryan Holiday?

  the airplane on the way down, people might help you subsidize that thing, right? Like you can go to your boss and go, hey, I want to get a degree in X, Y, or Z. What do you think about this? And they might be so afraid to lose you that they'll support you. Now, sometimes that can be a form of golden handcuffs and eventually you do have to, to walk away. But again, it only seems scary until you start moving in the direction of the risk. And then it turns out it's, it's less scary.

• 17:33Speaker 01

  Yeah, you know, it's also funny because I think like, There's a lot of people these days that hate bosses and hate corporate culture for many understandable reasons.

• 17:41Ryan Holiday?

  Yes.

• 17:42Speaker 01

  Simultaneously, if you're the best performer in the place that you are, you're an A player and you keep crushing it, the allowances you get are wild.

• 17:51Ryan Holiday?

  Right.

• 17:51Speaker 01

  Now, if you're a mid to low performer and your performance starts to dip, you got no allowances. You got nobody helping you buy the plane. And one of my great gifts in finance was I saw this all the time. It's very normal in finance. People will fund your next fund. Like they'll give you money to compete with them in an investment structure. That's like normal.

• 18:08Ryan Holiday?

  Right.

• 18:08Speaker 01

  It's normal to have somebody go fund your startup. You know, if you are a high performer and you leave. And so, yeah, if I was a young person, I'm like, go work for like the smartest, hardest working people you can find in the world.

• 18:19Ryan Holiday?

  Yes.

• 18:19Speaker 01

  That take a bunch of risk so you can coat tail their risk.

• 18:23Ryan Holiday?

  Or make them dependent on you in some, like if you are a part of their operations and it is expensive for them to replace you, you suddenly have leverage.

• 18:33Speaker 01

  Yeah.

• 18:33Ryan Holiday?

  And, uh, and then you have a power, that leverage uh, becomes a powerful ally when you want to do your next thing.

• 18:41Speaker 01

  Yeah, it's, it's, I totally agree with that. And I think as like leaders, which I know, like you talk a lot about this, about leadership and these virtues that are so important for, for somebody who's aspiring to be a leader. You know, if you can teach your team, I love that quote. I can't remember if it's, it's one, it's a saint something, but how they talk about, if you want to teach your people to build a boat, don't teach them about ropes and nails and wood. Teach them to yearn for the vast and endless sea. And I go back to that so often because I think your job as a CEO is really only to do like three things. And the first one is to give them a vision so big that they can see themselves winning bigger with you than without you. The second is to course correct and be very clear on what explicitly you're going to do next. And then the third is to make sure that you never run out of money

• 19:26Speaker 01

  to be able to continue to fund the first two. And I think a lot of leaders forget that. And like, if you can teach your team to yearn for the thing, you'll win. And every time in business, when we're not yearning for the thing is when we're not winning. And I see it again and again and again.

• 19:43Ryan Holiday?

  Okay, so last note on courage. I will say, though, it is always scary and it's good that it's scary because if it's not scary, you're either delusional, as we were talking about, or what you're doing is safe and therefore probably not much upside, right? Like, if it seemed like a good idea to everyone, if it was guaranteed to work out, well, then everyone would do it and there probably wouldn't be much of a market position in it. Like, it is by definition, all the good things, all the good businesses have to seem crazy, or stupid, or weird, or dangerous, or they'd already be commodified.

• 20:22Speaker 01

  Yep, especially in the age of AI.

• 20:23Ryan Holiday?

  Yeah.

• 20:24Speaker 01

  Like, I think, you know, the other thing with courage is to not just be a copycat forever trying to get rich quickly.

• 20:29Ryan Holiday?

  Yeah.

• 20:30Speaker 01

  Because right now, I sort of giggle on X when I see these, "I made $70,000 in 20 minutes with this one-shot thing I coded on AI."

• 20:38Ryan Holiday?

  Yeah.

• 20:39Speaker 01

  And I always go, "Well, next question. If you one-shot coded it in AI with 20 minutes, what's going to stop the next guy from doing it?" And so...

• 20:45Ryan Holiday?

  There's not much of a moat there. If it's as easy as you said,

• 20:48Speaker 01

  Yeah, exactly.

• 20:48Ryan Holiday?

  Then it's easy for everyone. Yes.

• 20:50Speaker 01

  Yeah, exactly. And it's true. So have some courage to do something creative, too.

• 20:55Ryan Holiday?

  The more people doing it, the more competition you have, right? Like, I think Peter Thiel's talked about this, where it's like, "Do you want to be like the 80th restaurant selling the exact same thing in the town that you're in?" Like, it has to be a little crazy and different if you want to stake out a good position, which means, like, when you propose it to people, they're going to be like, "What? No, don't do that. Do the thing everyone else is doing."

• 21:19Speaker 01

  Yeah. You know what I see the most in business owners these days? That's the weirdest thing. I'm kind of playing around with calling it, like, it sounds too close to Robert Kiyosaki, but I'm calling it rich owner versus poor owner mindset. And it's so consistent across owners, like, almost all owners. Underpriced themselves and their lack of confidence shows in their pricing. And they don't actually have the courage to charge more. They charge too little and they don't realize that you have a massive volume game then. And that is a really hard game to play. And it would just be way easier if you sold things to rich people and you charge them more.

• 21:52Ryan Holiday?

  Yes.

• 21:52Speaker 01

  And you can always start that way. I think people feel like it's elitist or they're not capable or they have the wallet share phenomenon where they believe, oh, because I would never pay for that, somebody else would never pay for that. Terrible way to do business. So half my job is literally getting in business owners' businesses these days and saying, why are you 100% underpriced to market?

• 22:13Ryan Holiday?

  Yeah.

• 22:13Speaker 01

  You know?

• 22:13Ryan Holiday?

  The courage to charge what you're worth doesn't seem like that would require much bravery, but it does because it requires awkward conversations. It requires hearing no, right? It requires getting out there a little bit. Like if everyone is charging $5 for something and you go into a minus $500, people are like, whoa, what's with this guy? So now you're standing alone, which requires courage. And then, uh, yeah, the, the risk of, of, of taking the, the certain way for the uncertain path. Again, this doesn't feel like courage. It's not the same as running into a burning building, but it does require a certain amount of confidence. It requires a certain amount of risk. Now, we'll get to justice as the other virtue, but it's like, you're not doing anyone any favors,

• 22:57Ryan Holiday?

  yourself included, by charging less than your worth. Like accepting less than market rate or leaving money on the table. You're not helping anyone. This isn't like, oh, hey, I, I keep the price of this low so, so schoolchildren can afford it. You're, it, you're,

• 23:12Speaker 01

  That is true.

• 23:13Ryan Holiday?

  These are rounding errors for huge companies and you're just refusing to charge what, what you're worth.

• 23:17Speaker 01

  It, I think it comes down like, you know, you were just like the rest of us. You were all indoctrinated, we were all indoctrinated, I think, from a very young age, to believe in institutions telling us what to do. To believe that charging for things is somehow wrong. You know, what is the root of all evil? Money. We just have these weird programments. And I think you're just, you're exactly as successful as you programmed yourself to be. And you will only program yourself to be successful by reading all the things you were probably typically not told to read. In school and by doing things that allow you to continue to grow and succeed. You can't win in business if you're the cheapest one continuously over time unless you're the best operator in your area. Like unless you're Sam Walton of Walmart level good, you should not be the low cost provider.

• 24:02Speaker 01

  He was a psychopath. That's why he was so good at this, you know? The man would fly his airplane over parking lots to see which stores were full. Then land in the parking lot and go yell at everybody about why nobody was there. I mean, he was unhinged.

• 24:17Ryan Holiday?

  Yeah.

• 24:17Speaker 01

  They would find him laying on the ground with a tape measure in between aisles to see if the aisles were too far apart because he needed everything really close together in order to have massive volume. Like if you're that intensive an operator, you can be cheap. If you're not, you can't. You gotta charge more.

• 24:31Ryan Holiday?

  Also, again, this also ties back to justice, which is like the more you charge, the more generous you're able to be with the people on your team. Like so, so by remaining small and keeping things on this sort of shoestring, like perpetually on the verge of going out of business. You're not able to to bring as many people into said business or you're not able to build an organization that could support and help and grow. You know, just generally be better in the world. So yeah, the, the courage to go, hey, this is, this is what I'm worth. This is what it's worth to me. Also, I think someone gave me this advice one day, like it's not what it costs you. It's what it's worth to them. That's what their price is, right? And it's, it's hard for people to do that. And not just talking about what, what are you pricing your widgets at?

• 25:14Ryan Holiday?

  But like what your hourly rate is as a freelancer, what you know, you'll accept as, as a deal or a contract, as an athlete or a musician or a writer. And then also we're talking about the courage to, to, to stand up, to go into your boss at an annual review and go, hey, I want this promotion. Or hey, this is the salary that I need or deserve, given the value I bring to the organization. And it takes courage to do that.

• 25:39Speaker 01

  Yeah, totally. You know what's also a great way to get more courage or to find just answers is like to know your shit. And so like, you know, when you have the data on what you should actually charge, on what you should actually get market compensation, it's a lot less scary.

• 25:55Ryan Holiday?

  Sure.

• 25:55Speaker 01

  Because you go, hey, I don't know. I would like, I mean, I've had people do it to me. Go, I would like a raise. I go, yeah, me too.

• 26:01Ryan Holiday?

  Yeah, sure.

• 26:01Speaker 01

  You know?

• 26:02Ryan Holiday?

  And this isn't just a, well, I saw on Glassdoor, the range is here to here. Because your boss also knows their shit.

• 26:08Speaker 01

  Yeah, exactly.

• 26:08Ryan Holiday?

  And they go, nobody, I, I could walk across the street and verify in two seconds that this is not actually what here and here, right?

• 26:16Speaker 01

  No, no.

• 26:17Ryan Holiday?

  If, if you can get that over there, by all means, I'll give you a recommendation. Right? So you, you have to know your real shit from real work, not just, you know,

• 26:24Speaker 01

  Yeah, and what your value is. I mean, I think a lot of getting what your worth is figuring out, what do you drive? And honestly, it shocks me how few people realize what their value is to the company, or like what the company needs and how it makes more money.

• 26:40Ryan Holiday?

  Right.

• 26:40Speaker 01

  I'm like, don't, aren't you curious at all? Because if you knew that, you could ask for more because you'd say, hey, I know this month, we actually wanna, I don't know, we want to bring more people into contrarian thinking. We want more people to sign up for our workshops in our boardroom. Okay, great. Well, what would that mean? Well, if I drive some additional above and beyond, could I get a cut of that? Yeah, sure.

• 27:02Ryan Holiday?

  Sure.

• 27:02Speaker 01

  No problem. It's not that difficult. The problem is, most people just want to say, I want a salary increase.

• 27:07Ryan Holiday?

  Yes.

• 27:08Speaker 01

  Which is a very quick way to say, I just want you to pay me more and me to have zero risk.

• 27:11Ryan Holiday?

  Yeah, I, I would like to keep doing the same work for more money, which is, of course, the deal everyone wants.

• 27:17Speaker 01

  Yeah, me too. Some days, you know, find me on the right Tuesday.

• 27:19Ryan Holiday?

  Yeah, yeah.

• 27:20Speaker 01

  I want to go back to it.

• 27:21Ryan Holiday?

  Okay, so the, the next virtue for the Stoics is this idea, sometimes it's rendered as temperance, which is moderation. I, I prefer to see it as self-discipline or self, sort of, ownership, in the sense of being in command of your emotions, your desires, your urges, your... Your envy, all of these things. So, so talk to me about why that's an important skill as a, as a business owner.

• 27:43Speaker 01

  Well, the business will fall to your level of activity, not your level of desire. And so, you know, you have to be the ultimate standard in your business. And your team, like children, will not listen to what you say. They will watch what you do and then do a little bit less than that. And so that is the hard truth.

• 28:01Ryan Holiday?

  Yeah.

• 28:01Speaker 01

  And so if you want to win in business, you have to be unreasonable in your level of activity, at least for quite a while, so that your team aspires to a level that is less than that. And that is, by the way, very reasonable for them.

• 28:13Ryan Holiday?

  Yeah.

• 28:13Speaker 01

  Because they don't have all the upside that you do. So you're always going to work harder and care more than most of your employees. Now, the great employees, the ones that I turn into partners over time, are the ones that care just as much as I do. And then I want to travel through time with them. But I find that a lot of people want to get into business or want to be really successful with money. But they aren't willing to do the absolute boring, mundane work that is the game of business.

• 28:38Ryan Holiday?

  Yeah.

• 28:39Speaker 01

  Like, business to me, more than anything else in life, is who can handle doing the most monotonous, boring things for the longest period of time, far past when it's reasonable or when you could at all want to.

• 28:50Ryan Holiday?

  Yeah.

• 28:50Speaker 01

  And if you can do that, you'll actually be really, really successful. Because it's not the really bright moments. It's, it is the moment, again and again and again, where, you know, I go to like, some of the people that I admire a lot in business, at least, which would be like, an Elon Musk, who's like, I'm just gonna sleep on the factory floor until I get this rocket built, and I'm going to work right alongside you, and we're going to stay in this misery.

• 29:14Ryan Holiday?

  Yeah.

• 29:14Speaker 01

  And it's not my desire to stay to sleep on a factory floor, but it's-

• 29:18Ryan Holiday?

  I would disagree. I think he creates a lot of the misery by, by being impulsive and emotional and by making somewhat irresponsible decisions, which he then has to- I think he sometimes glamorizes the life or the grind.

• 29:34Speaker 01

  The hustle.

• 29:34Ryan Holiday?

  He calls it like demon mode or whatever.

• 29:36Speaker 01

  Yeah.

• 29:36Ryan Holiday?

  Whereas like, someone with a-

• 29:38Speaker 01

  Hardcore.

• 29:38Ryan Holiday?

  More of a plan or more of a corporate structure around them, or could delegate better, wouldn't have to do that.

• 29:45Speaker 01

  Yeah.

• 29:45Ryan Holiday?

  But I get, I get your point, which is like, you gotta do the work.

• 29:48Speaker 01

  I think it comes down to what do you want to build?

• 29:51Ryan Holiday?

  Yeah.

• 29:51Speaker 01

  You cannot be corporate and take society to the moon and to Mars faster than the government and all corporate institutions and even beat Jeff Bezos.

• 30:01Ryan Holiday?

  Right.

• 30:01Speaker 01

  Like Jeff Bezos, to me-

• 30:03Ryan Holiday?

  Also pretty driven, yeah.

• 30:04Speaker 01

  Is very driven, but probably much more corporate, reasonable, time-bound, decision-based, hyper-successful. Elon is, in many ways, not, in my opinion, as much of a business builder as he is a mission-driven leader.

• 30:19Ryan Holiday?

  Sure.

• 30:19Speaker 01

  So it is emotional and it is chaotic because nothing like that has ever been done before in history. But do I think you have to be Elon? No. In fact, I think it would be miserable to be him. I couldn't even imagine-

• 30:29Ryan Holiday?

  And you said it's pretty miserable to be him.

• 30:31Speaker 01

  Right. So I don't think you have to be that. In fact, I think you should love the business that you built.

• 30:35Ryan Holiday?

  Right.

• 30:35Speaker 01

  And because most people don't want to be him.

• 30:38Ryan Holiday?

  Right.

• 30:38Speaker 01

  Most people don't want to build billion-dollar businesses. Building a billion-dollar business is miserable. I mean, we're on the path and, you know, our business is worth a couple nine figures and we do a lot of revenue a year and there are many days where it's miserable. But the one benefit, I think, to the way we run businesses at least, is because we are so systems-oriented, you have what you just talked about, which is we just kind of know every single day what foot to put in front of the other, how to hire, how to train people, and how to processize it, where our self-discipline clones in the organization.

• 31:10Ryan Holiday?

  I just know it's like you crash the car in a ditch and then you rally the troops to pull it out of the ditch. That, you know, I don't think you get credit for the long hours of pull, like, I just spent Christmas pulling the car out of the ditch. It's like, okay, but you were drunk when you drove it in there and that's on you.

• 31:26Speaker 01

  Yeah.

• 31:26Ryan Holiday?

  I do think there's this, um, there's this idea, people want to be their own boss. They want to be in charge. They want to control their own destiny. And I think they think that that somehow exempts them from like anyone getting to tell them what to do. And that's like, there's this line from Seneca where he says, "No one is fit to rule who is not first ruler of themselves." And so they think, like, I think they think that being in charge, running a big business, it's like, it's awesome because nobody's bossing you around. But it's actually, no, you have to be the boss of yourself. You have to boss yourself around and you- Don't have the benefit of anyone checking in with you and going like, hey, did you, did you make sure to do that thing? Like, hey, did you get up early? Did you stay up late? Did you work harder than you want to work?

• 32:10Ryan Holiday?

  And so there is this, I think glamorization of working for yourself, being the boss, being the leader. And what people are forgetting is it's actually forcing you to do the job you were doing before and your boss's job, but just of yourself.

• 32:24Speaker 01

  Oh, yeah. I mean, I have two sides to the coin on this. I've really been thinking about it a lot lately. One side is if you want to be in charge, you are going to have to work harder than anybody else in your company for longer than anybody else. And there is no other way around it. You can also make more money than anybody else. You can probably have a bigger impact than anybody else. And you can see what you're actually made of. You can see what you're capable of. It's incredible. On the other hand, I think that we have really started to obsess on this trauma bonding around being an entrepreneur.

• 32:57Ryan Holiday?

  Yeah.

• 32:57Speaker 01

  And it's almost like it's so miserable and hard. And if you don't think it's miserable, you're lying and you're not in the game. And I'm a little bit lately, like, my life's pretty fucking rad.

• 33:08Ryan Holiday?

  Yeah.

• 33:09Speaker 01

  And do I just have a baseline level of kind of happiness? Yeah. But also it's really sweet to be an owner of business. And not in like hustle, you know, Lamborghini Ferrari, private plane type. But in that you do get to be your own architect. And so, I don't know, I'm going back and forth with this real pushback to, can't you be really quite successful? Running a business that does a couple million dollars a year? Doing it your way? Maybe it's in a small town. Maybe it's with a small team, but you are in charge and the CEO is on the door and that's your name. But you simultaneously still get to go to the kids' events and you still get to have your activities. And I think that is totally doable.

• 33:50Speaker 01

  And we don't have to have this hustle porn misery addiction to trauma bonding over being an entrepreneur.

• 33:57Ryan Holiday?

  There's two sides of the idea of discipline. So discipline isn't just, I work harder, I sleep less, I push my, my boundaries more. It's also the restraint to go, this is what we're doing this year.

• 34:11Speaker 01

  Yeah.

• 34:11Ryan Holiday?

  No more and no less.

• 34:13Speaker 01

  Yeah.

• 34:13Ryan Holiday?

  Right? Or these are the hours that I operate in, these are my priorities. One of the things you find when you have, like, we opened this bookstore a couple of years ago. The first thing people do is like, are you going to open another one? No, the discipline to say, the project was to do one thing. And that this is what success on that thing is like. Now, it's not the end of my ambition, there's other things I want to do. But that's the culmination of that particular ambition. And that reminding myself that my dream was not to have a chain of bookstores, which should be a distraction, both from what I actually want to be doing and what I want my life to look like. And so you have to have the restraint to go, hey, I'm going to keep my head down. I'm going to do what I'm supposed to do. I'm not going to go to every conference that invites me.

• 34:57Ryan Holiday?

  I'm not going to jump on every problem that comes up. I'm not going to do every interview that comes up. That, that was one thing that happens if you're a public facing person is you go, hey, I got here, I built this brand by jumping on every publicity opportunity, by doing every project, and then go, I don't like that pitch. I'm going, I'm going to let that pitch go by and I'm going to wait until there's one I can really get behind. And that requires restraint. It's this two sides of like drive and ambition, but then also restraint and a sense of, of what your limits are.

• 35:26Speaker 01

  Yeah, it's a great point. And also the discipline, like, if you want to be successful long-term, I'm pretty sure you can't do it by yourself. I know that now lots of people will say, well, there's a billion dollar business built with one person and that's going to happen. I think that that is fake and I do not believe that. And I do not think that will ever be true.

• 35:46Ryan Holiday?

  That's what you would tell a New York Times reporter because you want them to write a story about you.

• 35:49Speaker 01

  A hundred percent. Yeah. And we would both know because we've written titles before. Like, that's just not reasonable. So like what you actually have to do is one, you have to hold your own boundaries. And then two, you've got to bring along other people who are super disciplined. You are disciples in your same discipline. And so, you know, this idea, and you talk about it all the time with the Stoics, but. Of the great leaders of men. And so your best discipline, I always believe, is really pouring into your team and getting them to be these disciples that go out and do the things for you. Theoretically, if you actually wanted to, you could have a chain of 100 bookstores, but you'd have to have an incredible team to make sure that Ryan could still write the books that tens of millions of people read, as opposed to spending time on the invoices of the books in the stores, right? And so I do-

• 36:33Ryan Holiday?

  Well, the discipline to bring people on is like so sharing. And like, if you're like, no, this is all for me, it's all about me, like, the discipline even to let go of some of the control, these are all, we tend to think of discipline as just working harder and doing more.

• 36:46Speaker 01

  Yeah.

• 36:47Ryan Holiday?

  And it's, it's much more subtle than that.

• 36:49Speaker 01

  Oh, no. I mean, God, if you want to win, you have to say no to so much, it feels uncomfortable.

• 36:53Ryan Holiday?

  Yes.

• 36:53Speaker 01

  And I do it nonstop. I mean, the, the idea that doing more is going to make you win is, I think, why so many entrepreneurs are miserable.

• 37:01Ryan Holiday?

  Yeah.

• 37:02Speaker 01

  Because they have bought into the idea, if I just do one more, I will become better, bigger, richer, et cetera. And in fact, it's usually, what are the 10 things you need to stop doing right now?

• 37:12Ryan Holiday?

  Right.

• 37:12Speaker 01

  That are burning up time that you can't even picture? And what are the two things that if you did them would make everything else meaningless? And if you find those, then you really win.

• 37:22Ryan Holiday?

  Yeah, and, and the, the discipline to, to understand, you know, there's an infinite amount of money in the world and a finite amount of time. And which do you value more? What is the point of being successful if you can't use it to buy time and you can't use it to live the actual life that you want? There is this kind of insane, like, to be an entrepreneur, you have to have a good sense of delayed gratification, but you'll end up missing the whole point if you endlessly delay gratification, right? Like, if you never get to enjoy it, if you're sort of in harness your, your whole life. Or if you're like, yes, it's miserable, I hate this thing, but at some point I'll sell it and then I'll be happy. You don't know that that's true.

• 38:05Ryan Holiday?

  And you might not get to that, that point.

• 38:09Speaker 01

  It's actually a good, like, frame, that idea of, are you in harness or are you out? Are you free in the field or are you under plow? And, and I think- You know, if you're an entrepreneur and you're thinking about that, it's like, how much time do you actually spend under tension in that harness? And then how much time do you spend on long walks, on vacation? One of the most useful things I ever did to have better discipline about enjoying life, because that's not my natural state, is getting married. And like, I think partnership and marriage is one of the best ways possible to offset.

• 38:40Ryan Holiday?

  You're bounced out by another person. They're like, what are you doing?

• 38:43Speaker 01

  Exactly.

• 38:44Ryan Holiday?

  Yeah, this is crazy.

• 38:45Speaker 01

  Yeah, and it's, everybody talks about, oh, the old ball and chain, or they hold me back, or they don't. I go, that's the point.

• 38:51Ryan Holiday?

  They tether, they also tether you to reality.

• 38:54Speaker 01

  A hundred percent.

• 38:55Ryan Holiday?

  You're sounding like an insane person right now.

• 38:57Speaker 01

  Yeah.

• 38:58Ryan Holiday?

  And then they're also saying like, well, what about me? You know, what about, when are we going to live this life that you promised?

• 39:03Speaker 01

  Yeah. And so I actually think, I know that a lot of people today are like, well, you know, the best partner is the one that supports everything you do unequivocally all the time. And being married to an entrepreneur is such a blessing. No, it's not. Being married to an entrepreneur can be extremely miserable and extremely self-focused. And the spouses that sign up for that, like, they need a medal too.

• 39:25Ryan Holiday?

  Yeah.

• 39:25Speaker 01

  And so, and you know, my husband is in the game with me, but he is also the very first one to say, life is way bigger than this. And he has actually seen life or death. And to pull you out of the moment where you're obsessed about something like a P and L or a spreadsheet that you're not going to remember in 50 years.

• 39:40Ryan Holiday?

  The chances are, if you are driven, if you're talented, if you're successful, if you've built something, chances are you, you need more of a check than you do an enabler.

• 39:50Speaker 01

  It's so true. That's a good point, actually.

• 39:53Ryan Holiday?

  You don't need encouragement. You, you have plenty of that.

• 39:56Speaker 01

  Yeah. But that is sort of the advice, I think, by and large, these days, is that your person should agree with everything you do politically. They should agree to everything you do work-wise. They should support both unequivocally. And if they don't do that, then they're holding you back. They can't see your vision. You know, they're not a real partner. And I think we have to kind of question that and go, is that true?

• 40:17Ryan Holiday?

  Right.

• 40:17Speaker 01

  Or is this person actually the person who's going to allow you? I mean, things go a lot faster. We call them the two O's at my company. But if all you do is row a left oar on a boat, you go in a circle.

• 40:27Ryan Holiday?

  Yeah.

• 40:27Speaker 01

  You have to row left and then right, and then left, and then right. And that is the beauty of partnership.

• 40:31Ryan Holiday?

  Well, we should talk about this when it comes to wisdom, but people think you want a board of directors that lets you do whatever you want. You think you want complete corporate control and that tends historically not to go well. That's actually not the role of the board of the directors. The board of directors, yes, it's a committee and committees can be short sighted, but committees do tend to prevent you from driving off of a cliff or burning yourself out or doing something that is illegal or, you know, very irresponsible. Their job is to be like, that's not a good idea. You need that.

• 41:02Speaker 01

  So funny. We actually, we created something called the boardroom at Contour and Thinking. And the reason why is because I needed in my business, a group of people around a boardroom who would help me make non stupid decisions and talk me out of the singular focus I can have when I am driven. And we started it because I didn't want to give away equity in the company. I didn't want a real board.

• 41:23Ryan Holiday?

  Right.

• 41:23Speaker 01

  And I was scared of the downside of boards, which is that they can be not incentive alive, conservative, blah, blah, blah. So I wanted somebody who I could listen to, but couldn't run everything for me. Like I was the skin in the game because I realized most entrepreneurs, they don't have that. I mean, your friends are often your competitors. So you have to be a little careful of that. You know, your family is sometimes a little tired of hearing from it. Your employees are going to tell you what you want to hear, or they're going to tell you what is the least amount of work for them. And so you need this group of peers around you sometimes. I really think you need three. You need, you need peers, you need advisors, and then you need people that are like 10 or 20 years ahead of you. And, and with those three things, you can just move faster because you can steal people's

• 42:08Speaker 01

  10,000 hours.

• 42:09Ryan Holiday?

  Yes.

• 42:11Ryan Holiday?

  Okay, let's talk about justice. So I think when people think business, they're probably not thinking justice, right? Because they're thinking the law, they're thinking legal standards. But I would say it's good that we live in a capitalistic society. It's this powerful engine. It unlocks creativity and there's more resilience to it than there is in central planning. But I've always believed that, that with that freedom comes the sort of voluntary responsibility.

• 42:36Speaker 01

  Yeah.

• 42:36Ryan Holiday?

  Right, which in a way makes it harder because it's like, if, if you lived in a, in a world where Right and wrong was very prescribed by the law, then it would be clear what you're supposed to do and not supposed to do, and you wouldn't have to think that much about it. But, but a business world where you can basically do whatever you want within some reason means that the business owner has a lot of discretion about how they choose to run their business and their life. This is why I've always admired John Mackey at Whole Foods. Like, nobody, he's like as libertarian as they come. He's, he's like, the government should not tell anyone how to do anything. But he's like, with my business, I want to pay my workers well. I want to make sure the, like, these are my environmental standards. These are my, my humane standards for like meat and stuff like that. This is the benefits I want to provide.

• 43:21Ryan Holiday?

  This is how I want to give back. So he's saying, you, government, don't get to tell me what to do, but I'm going to tell myself what to do beyond what you probably would have told me what to do if you, if you had to say.

• 43:33Speaker 01

  Yeah. Well, I, I think actually what's happened with our businesses is we become less just as humans every time we remove ourselves a little bit further from the hand on the fire. And so in my mind, one of the biggest things that's gone bad for business when it comes to justice is public stocks, third-party investors, and short-term incentives. And so I think most CEOs and business owners actually want to be John Mackey.

• 43:59Ryan Holiday?

  Yeah.

• 43:59Speaker 01

  Because you see it on the small business spectrum. They actually have pretty good compensation, market rates. By and large, these people treat their employees well. Their, uh, small business employee happiness is 40, 60% higher than big business employee happiness. So like the net normal, we are all some version, maybe less slightly altruistic than John Mackey. What happens then? Well, then you start to get people who are shareholders in the financial benefit of the company, but nothing else.

• 44:29Ryan Holiday?

  Yeah.

• 44:30Speaker 01

  And that, I think, is where capitalism's gone a little screwy and why I like private companies and not public companies. Because public companies are beholden to four months. You know, they have quarterly goals and, and that's it. And every, you know, three-month session when the quarter comes, they're using the next quarter to think ahead about what the next quarterly call is.

• 44:51Ryan Holiday?

  Yeah.

• 44:51Speaker 01

  And so I'm curious to see, because this is a little technical, but, you know, we've seen since basically the 1990s was the height of public stock market investing. That was also when most companies ever were listed on the public exchanges. Since then, We have had, that was about 9,000 companies were publicly listed. Now there's about 4,000 companies publicly listed. Why? Because you get a colonoscopy nonstop.

• 45:13Ryan Holiday?

  Yeah.

• 45:14Speaker 01

  Because you have to have like three people in your mind, which is your shareholders, your employees and your customers. They're kind of all at war slightly with each other, but definitely the shareholders are at war. And then you have all this government red tape about what you got to do with your company overall. And so I think that what happened in our society is that public companies and the stock market created this false buffer between what happens to employees and customers and what happens to shareholders and Wall Street.

• 45:43Ryan Holiday?

  Right.

• 45:43Speaker 01

  And because of that, we have really bad incentives. And environmental standards are really hard to care about when you work in three-month cycles.

• 45:52Ryan Holiday?

  Yeah.

• 45:52Speaker 01

  And so, all of that to say, when you run a small business, the great part, you can actually compete with the big guys in a lot of ways that they can't.

• 46:00Ryan Holiday?

  Well, I would also say that one of the perks of running a small business is it's both the perk and the burden of it, which is like, as a regular person, it's really easy to have opinions. Like, this is what I think the minimum wage should be. This is what I, I think outsourcing is gross or unethical, or I think people should do this or that. And then, yeah, then you have a business and you have to buy employee uniforms and making them in the US costs $20 a t-shirt and making them in China costs $4 a t-shirt. And now all of a sudden, this principal costs you money. And you might think, okay, so the business says, we'll obviously go with the cheaper one.

• 46:39Ryan Holiday?

  But if it's your business and it's your reputation and you have to justify and rationalize all these decisions, both to yourself and to other people, then all of a sudden you have to, you, you get to decide, right? And, and you have a responsibility to decide.

• 46:53Speaker 01

  Yeah.

• 46:53Ryan Holiday?

  And so, to me, there's something really empowering about running a business because it's like, you don't control the world. You, you only have one vote in an, in an election. But in your business, you get constant votes and says over how you think things should be done. And then you get to do them that way.

• 47:09Speaker 01

  Oh.

• 47:09Ryan Holiday?

  Or not. And turn out you're full of shit.

• 47:11Speaker 01

  And you get to see the consequences of actions.

• 47:14Ryan Holiday?

  Yes.

• 47:14Speaker 01

  Because a lot of time- Sometimes you can say things that sound great and are idiotic in life.

• 47:18Ryan Holiday?

  Yeah.

• 47:19Speaker 01

  Like, you know, there are lots of arguments to raise the minimum wage and you could believe in that or not. But when you do it inside of your business, you go, okay, so when I raised it that much, now I can't hire these other 10 people.

• 47:29Ryan Holiday?

  Yeah.

• 47:30Speaker 01

  So what is that good or bad?

• 47:31Ryan Holiday?

  Yeah.

• 47:31Speaker 01

  I don't know, but there's actually data and math associated. You can't have everything all at once.

• 47:36Ryan Holiday?

  Yeah.

• 47:36Speaker 01

  And so you get to start to play with the supply and demand economics. The other cool part about having a business is if you have a strong opinion, go put some money and work behind it.

• 47:45Ryan Holiday?

  Yeah.

• 47:45Speaker 01

  And so I think these days, like I loved the line, God, I can't remember who it was from, but the line was basically like, oh, I think it's Jordan Peterson, when he talks about like, before you go try to change the world with charity, why don't you go try to make your first dollars because dollars often move further than straight charity.

• 48:00Ryan Holiday?

  Sure.

• 48:01Speaker 01

  Do I agree with that in every way? No, but dollars do move the world. I've seen it firsthand. It's one of the reasons we run businesses the way that we do, because my belief is if we put more small businesses in the hands of local citizens, those businesses will keep money in the local economy, they'll hire from the local economy, and they will have happier citizens. Plus, like, I don't want to go to another Starbucks. I want to go to the coffee shop next to Ryan's store on Bassdrop, right? I just like that local experience. And so I've put my money where my mouth is, which is I could very easily, the way we started our business was buying a bunch of businesses. And I still own many businesses, but I used to buy them outright. That's private equity. And at some point I was like, well, if I keep doing that, I am the thing I hate in the world.

• 48:45Ryan Holiday?

  Yeah.

• 48:46Speaker 01

  And so I can't.

• 48:47Ryan Holiday?

  You roll them up, you create a centralized structure, you eliminate inefficiencies.

• 48:52Speaker 01

  You cut costs over time. So I could have kept doing that. And then I said, well, instead, let's go educate people about how to buy these businesses. Now, what's fascinating is we're so indoctrinated to the way that society works that people think private equity and running businesses like that is better than teaching people online. They think that if you teach people online to buy businesses, it's some sort of scam or shill or whatever. And I kind of understand that because there's a lot of people who shill things. But I go back to like, when did we get indoctrinated to that? That if I took 2 and 20, which is how they do expenses and private equity, of your dollars. That would be better than a one time fee that will be one one thousandth the cost of a business that you buy. And so you do have to pick. That was my stance.

• 49:33Ryan Holiday?

  Yeah.

• 49:33Speaker 01

  And I think the cool part about when you run a business, pick a stance and see, see what you're capable of holding the line of. And how strongly do you actually believe in the things? We, I, I think every company should have a creed, uh, the mission statement. There's lots of ways to do it. A lot of them are bullshit.

• 49:47Ryan Holiday?

  Yeah.

• 49:47Speaker 01

  I've seen them all. Everybody thinks you need to throw one up on the wall. Um, I believe they deeply, deeply actually change how a business operates. And ours, we have, we have a contrarian creed. There are 13 rules, 13, because we believe in making our own luck. And the first one is, um, that those who believe that is impossible should get out of the way of those of us who are doing it. And so like every single line on that creed says what we stand for. You know, you should tell the truth, even when it hurts, maybe especially then. And, um, then it gets to maybe, maybe you get to indoctrinate more people into your ideology in the world. And what a better way to do that than business.

• 50:25Ryan Holiday?

  Well, and it's, as I say, it's not a principle until it costs you something, right?

• 50:28Speaker 01

  That's good.

• 50:28Ryan Holiday?

  And I, I told this story and for many years, when I would talk about the stoic virtues, about this decision that CVS made like a decade and a half ago. They just decided that if we're like a health company, why do we sell cigarettes? Like that, it's bad for people and we're going to stop. So they, they do, and it costs them, I don't know, a billion dollars a year or something in revenue. And people were like, why? Like the, the rationalization to sell it is lots of other stores sell cigarettes. And if people want to get cigarettes, they'll just buy them somewhere else. And, and, and so they're like, look, if, if people buy this many cigarettes a year and CVS stops participating, the same amount of cigarettes will be sold. It'll just be distributed a little

• 51:08Ryan Holiday?

  bit differently. But actually what happened is cigarette sales nationwide go down, not like significantly, but just some percentage of those people that used to buy it from their neighborhood CVS or the one they would walk by in New York City, just stopped. They, they smoked less cigarettes because they were harder to get. So, so they make this decision that's, that's probably mostly about branding and, you know, uh, reputation and they got a lot of press when it came out. But actually they Effect nationwide, the sales of cigarettes, which, you know, blah, blah, blah, less people die from lung cancer as a result of this decision. And I would talk about that and I always thought it was cool. And then a couple of years ago, there's this little grocery store down the street from here. It's been in business since the 40s and it went up for sale.

• 51:50Ryan Holiday?

  My wife and I ended up, long story short, owning this thing. Not our dream, not what we expected. We were going to be like silent partners in it and now it's ours and we're running it. And as we're sort of doing the diligence after having bought it, which is not how you're supposed to do. I'm looking at what are the most popular, like, what are our most successful sales? And month in and month out, it's tobacco products. And now I have to go, fuck, okay. I don't like this. I don't want this. And so you, you take them out. And then what you're actually doing is just putting a giant hole in the, in the, in the P and L of a business. And, and not only are you doing that, but people are coming in and going, what? You know, they're like mad at you for changing the place.

• 52:34Ryan Holiday?

  But I had to go, hey, I can't just go around talking about this thing and saying that I believe it when somebody else does it. But then when it, in my own business, not want to remove 8% of revenue or whatever it is. And then have to be creative and come up with a way to compensate. But that, that is what owning a business allows you to do. Is take these sort of vague, abstract notions or values or opinions that you have. And then you either have, you have to put up or shut up.

• 53:01Speaker 01

  Yeah. You know what else is interesting too, is when you put yourself out into the world, the world tests it. And so, you know, like, I kind of always chuckle, we're, we're pretty hardcore at my company. We're intense. We work a lot. I'm pretty intense. I give a lot of feedback. And I imagine at some point there will be a hit piece. Cause that just tends to happen. It happens a lot with women CEOs too.

• 53:25Ryan Holiday?

  You let go of a certain number of people, some percentage of them are disgruntled.

• 53:28Speaker 01

  A hundred percent. And we're getting it, blah, blah, blah. And I always kind of chuckle at that because I go, when they say that, I'm just going to respond, I resemble that comment. Because the, the truth is that if you hang out with Cody over here and you hang out with Cody online, she's kind of the same thing. At least, like, I don't try on purpose. I mean, less makeup, you know, not as put together, like those things, right? But. The cool part about when you put yourself online is you really have to look yourself at the face because somebody will find you if you are not. And we have seen it. We have seen all the people who pretend to be X and then one day that real self comes out and it will destroy you. It can absolutely eviscerate your reputation. And I always liked the Warren Buffett-ism, which is you can make a mistake with a dollar,

• 54:13Speaker 01

  but you can't make a mistake with my reputation. If you do so, you'll be fired. And he says it more eloquently than that, but I believe that to the deep core of my being, you know? The only thing you can really do wrong in my business is if you lie, cheat, or steal, or you hurt a reputation.

• 54:26Ryan Holiday?

  Yeah.

• 54:27Speaker 01

  If you make mistakes, if you want to leave, if you give me hard feedback, if you have a little attitude sometimes, okay, that's fine. We can do all those things. But I do think business is a great mirror.

• 54:38Ryan Holiday?

  Yeah.

• 54:38Speaker 01

  And money is a cool metric because scoreboard often can tell you, like, am I believing and doing the things correctly that I say I would in the world?

• 54:48Ryan Holiday?

  Yeah, I did a piece a couple of years ago that was, you are what you won't do for money. So like, where do you draw the line? Where you're like, somebody's offering you X to do Y, and money is a hard thing to say no to.

• 55:01Speaker 01

  Yeah.

• 55:01Ryan Holiday?

  And I think early in my career, there were things I did for money that were not in accordance with my values and the discomfort from that, or the risk inherent in that, you learn, you learn over time that the best and the safest thing is to like, mean what you say and to not be a hypocrite and to try to genuinely do your best to bring like, how you operate in accordance with like, who you want to be. Mark Schulz has this line of not doing anything that requires curtains.

• 55:35Speaker 01

  Oh, that's good.

• 55:36Ryan Holiday?

  Like, anything that you wouldn't want, like, if your customers knew where your product was made, or the conditions under which it was made, or how you talked to people over email or whatever, if you have this exposure to like, hey, if people found out about this, that would be bad for me, the market is giving you a really strong signal, not to get better public relations or, you know, to enforce stricter NDAs, it's telling you, you gotta change.

• 56:07Speaker 01

  Oh, yeah. You know, it's... I remember I had an employee, actually. That was incredible employee. Really thought highly of her. She could have gone far at the company, but she broke one of the golden rules, which is she said really bad things about a client in a channel to our team.

• 56:21Ryan Holiday?

  Yeah.

• 56:22Speaker 01

  And we just have a hard line. That is one of the fireable offenses.

• 56:25Ryan Holiday?

  Yeah.

• 56:26Speaker 01

  Yeah. And it's, it's what if they saw it? And also, what if they realize that's what we think of them?

• 56:31Ryan Holiday?

  Yes, right.

• 56:32Speaker 01

  Like, how could you go and spend your life trying to make our clients' life better if you think they are dumb and incapable and should never be in this? If that is what you think, then one, we should say, hey, you're not a fit for us.

• 56:43Ryan Holiday?

  Right.

• 56:44Speaker 01

  Because X, or you should never say that about your customers. And it's actually a really good lesson in business that all of us have to remind ourselves about because you're, a customer is going to drive you fucking crazy at some point.

• 56:54Ryan Holiday?

  Well, and then it presents you, like when we say the obstacle is the way, the opportunity there is as expensive as that is and frustrating as that is, it's also a chance for you to say to everyone else, hey, this person, I, I don't want to lose this person. This person does drive value for the business, but they acted in a way that is in violation of our values and I'm willing to take the hit. This is the problem that Uber got in, in before the sort of turnaround, which is like, they would make these exceptions for the star performers, right? And what that created was a sort of culture where sexual harassment was prevalent and that people were saying things that like, by the way, when the, when the lawyers discovered them in discovery,

• 57:37Ryan Holiday?

  they were, there was a vulnerability to it, right? Like you, the decision to go, hey, I'm going to let this person go, even though they drive value to the business because they don't follow the rules or they do X, Y, and Z. That's a really, it's a hard thing to do, but it's also a really powerful thing to do inside the company.

• 57:54Speaker 01

  Yeah. You know, and the other thing, it's also okay for you to pull this stuff up and show it to your boss. Like, I think too seldom. People don't hold the person who is ahead of them in line, too.

• 58:08Ryan Holiday?

  Oh, sure.

• 58:08Speaker 01

  And so like, you know, if you're an employee and your boss has rules and the boss doesn't stick with the rules. If you're an employee and you're being held to a standard, but they're not holding the standard. I think you might be surprised at what happens when you bring that boundary up to them and say, hey, I am happy to do that. But I just want to note, because I know that you, as the head,

• 58:27Ryan Holiday?

  Yeah.

• 58:27Speaker 01

  are the representative for everybody else at the company. And you care more than anybody else what happens here because you want to make more money, more success. You're such an incredible leader, a little flattery goes a long way. And then you can say, but you're doing this and I don't think that's in concert. Like, you can say that to your boss. And in fact, if you're in a place where you cannot say that to your boss, you should leave.

• 58:46Ryan Holiday?

  Yeah. Hey, I thought our values, we only, we only make stuff in the US. But like, here we are, the people who make our boxes, doing it cheaper X, Y, and Z. Is you, you want like, I'm bringing this contradiction. It's ultimately your call as the boss, but like, I'm going to present this contradiction to you. And yeah, if you're a good, a good lesson to learn. I remember I was having to talk to my agent about something. And I was like, I was talking to my wife about it. I was like, what if he gets mad? You know, what if I, what if, if I, I think, hey, I think this part of our arrangement's unfair and I want to change it. And I was like, what if he gets mad? And she was like, that's such an insight into your childhood that you, you're concerned about doing something that's right and getting yelled at for it.

• 59:29Ryan Holiday?

  She's like, if, if he doesn't respond well, he shouldn't be your agent anymore.

• 59:34Speaker 01

  Yeah.

• 59:34Ryan Holiday?

  And like, that's a really bad sign. And, and so I went to him and I was like, hey, I don't think this is fair. And he was like, you're totally right. Let's fix it. And I was like, oh, okay. So, so that's exactly what you would want to see. And so, yeah, this is also why you want to do business with ethical people as well.

• 59:48Speaker 01

  Yeah. You know, and I think there's nothing wrong with you bringing up the truth in business to people around you. And more often than not, it's really hard.

• 59:57Ryan Holiday?

  Yeah.

• 59:57Speaker 01

  And there is someone right now that you're picturing who doesn't treat you right in business, who doesn't treat other people next to you right. And I think like, it's a very powerful thing to just lean into them. And I always like to do it this way and say, hey, I don't know if you're open to feedback, but if you are, have a little thing that I think might be helpful for you. Who's going to say no to that? Very few people. So you say, they say, okay, yeah. You say, well, I've noticed that the way that you've treated Samantha kind of demoralizes her.

• 1:00:29Ryan Holiday?

  Yeah.

• 1:00:29Speaker 01

  And it doesn't seem like it's working. And I only know that because it's happened a few times to me, too. I think that it might be more helpful if you did it like this. Are you open to trying a different way? And what you're doing right then? You're sandwiching the tough feedback with two open-ended questions that are very kind and hard to say no to.

• 1:00:47Ryan Holiday?

  And if they do say no, they've told you a lot, right?

• 1:00:49Speaker 01

  If they say no, you say, that's not for me. Or you, you know, do, uh, like one of the things my mentors taught me back in the day, if they say no, you do something very simple, which is, you know what? That doesn't work for me. And a lot of times, there's not, there's not a way to argue for that doesn't work for me.

• 1:01:06Ryan Holiday?

  Yeah.

• 1:01:06Speaker 01

  And so you might have to leave, you might have to change, but you might also be shocked how often it works.

• 1:01:11Ryan Holiday?

  Yeah, no, I have a, I talked about this in the courage book. I had a moment like that where I, I went to my boss when I was at American Apparel. He'd asked me to do something I thought was unethical. And I was like, I don't want to do that. And, and I was nervous about losing my job. And it's like, why would I want to? Why would I be nervous about losing a job that's asking me to do something unethical? In fact, that should be very clarifying, right? It could be just, the answer could be disappointing, but, but it shouldn't be something you're afraid of, because if, if you don't get the answer you want, you did get the answer you want to another question, which is, should I continue to be a part of this?

• 1:01:46Speaker 01

  Or you might even have something happen, which is you didn't understand the whole picture. You know, so I might be like, why do you keep demoralizing Samantha? She might be like, Samantha's on her fourth port performance review and we should probably let her go, go when she stole last month. And you're like, oh, fuck, okay, well, maybe I'm, maybe I'm wrong. There could be some likelihood, you know?

• 1:02:04Ryan Holiday?

  Okay, so the last virtue is, is wisdom, uh, which I think people tend to think of as like this thing that you have at the end of your life, not a thing you're accumulating through the course of your life, right? Like, like it's not this place that you arrive. It's more of a, a process. It's a byproduct of, of learning and experience and mentors and all these things. But it is, it is weird how often people will be like, I'm gonna, I'm gonna risk my entire life, all my money to go start this business. And then, by the way, I'm not going to read any books about it. I'm not going to ask for anyone's advice and I'm going to totally learn it on my own as if nobody has done this before. It's crazy.

• 1:02:43Speaker 01

  It makes, you know, one of my lessons that I learned early on in life is like, I remember talking to one of my mentors. He gave me a piece of advice that was basically like, Whatever you learn from somebody, try to be the person that they tell other people about. And I thought about that and I was like, oh yeah, because all my success stories, people who have listened to me and gone on, I can name them.

• 1:03:05Ryan Holiday?

  Yeah.

• 1:03:06Speaker 01

  You know, and we have a lot. And so if you are the person that listens so intently to other people on your journey, and then tells them a little thank you, like, hey, Ryan, I just read your book. It was incredible. Thank you so much. Here's a small thing. You get those all the time, right? But what I love about that little drop, he's not, he's not asking you to respond. He's just saying, this is great. And if you're doing it with people who aren't that well-known on the internet, most people have never given somebody advice and have them say, thank you, I used it and it worked. And then given somebody advice and then have them say, thank you, I used it and it worked.

• 1:03:37Ryan Holiday?

  Right.

• 1:03:37Speaker 01

  And if you do that a few times, you turn people into mentors that you didn't even really mean to. And they certainly didn't mean to mentor you because that's a big, you know, burden. And so I think you're crazy to not take the wisdom of others and apply it to your life. I've always tried to be the best student of anybody I learned from.

• 1:03:54Ryan Holiday?

  Yeah, it's, we sort of celebrate learning by experience as if that's not the least efficient, most expensive way to learn. I mean, it's obviously great and you have to, there's some things you can only learn by experience. But like, the idea of learning it by trial and error, when people have been in your exact position and written books about it, people have been in your exact position and made catastrophic mistakes that there are exposes and articles about, like even, you know, just opening a business on this main street. I'm looking around, we're doing it and it's like, why are all these shops empty? And it's like, I went around, I asked the Chamber of Commerce, I asked all the real estate, I was like, why do things not last in this town?

• 1:04:34Ryan Holiday?

  And it's like, oh, there are these reasons. And some of those reasons are avoidable. Some of those reasons are, give me feedback on things I have to do differently. But it's just the idea of like, look, somebody went out of business in this space that you're trying to open a store in, right? Why? It would probably be good for you to figure that out before you've taken out a home equity line of credit on your house.

• 1:04:57Speaker 01

  Oh, 100%. I mean, it's one of the things that keeps me up at night. If there's one thing that scares me,

• 1:05:01Ryan Holiday?

  Yeah.

• 1:05:02Speaker 01

  it's that we talk about buying businesses on the internet and then somebody just goes and buys one.

• 1:05:05Ryan Holiday?

  Yeah.

• 1:05:06Speaker 01

  And then they go, what the fuck did I just do?

• 1:05:08Ryan Holiday?

  Yeah.

• 1:05:08Speaker 01

  And it scares me, which is why we originally had a course on buying businesses. And now we don't. And the reason why is because I don't think that that is enough. I think you have to actually have a group of people around you for the full year you were going through this process.

• 1:05:23Ryan Holiday?

  Yeah.

• 1:05:23Speaker 01

  And you need people to call on the dead of the night. And you need them, you need to see other people's reps real time. You need to see all the mistakes they made. You need to look at the case studies. And so we actually killed it because we were like, not only is a book not enough, a course isn't enough. You have to actually have real humans and almost treat it like a mini MBA. And, and so I feel so strongly in that. Like every chance I get, I often think about how Warren Buffett, the only thing he does most days is read and learn.

• 1:05:50Ryan Holiday?

  Yeah.

• 1:05:51Speaker 01

  And then, you know, let's call 5 to 10% of what he does is action.

• 1:05:55Ryan Holiday?

  Yeah.

• 1:05:55Speaker 01

  And, you know, 90 to 95% of what he does is data accumulation. And I think a lot of people these days would say that's mental masturbation and you're, you're pushing it off. But if you are committed and disciplined, the type of person that is going to make a move, but you do it from a data and knowledge basis, your likelihood of success is just so much higher. I mean, we know, we know in our group, about 30 to 40% of people who join buy a business. The average amount of people that buy a business is like 0.03%.

• 1:06:25Ryan Holiday?

  Yeah.

• 1:06:25Speaker 01

  Now, there's some bias there because this is a self-selected group and all of those things. But I wonder why, again and again, we are so willing to get distracted by all the little learnings in life, but not go deep into the one learning that might actually change our life.

• 1:06:40Ryan Holiday?

  It's very unlikely you're going to be successful at something that you have not made yourself a student of. And the, the industry's startup entrepreneurs are especially guilty of this. Like Silicon Valley, they're like, oh, this is a huge industry. I'm going to, I'm going to disrupt an industry that I, by the way, know fuck all about. Like, like I read an article about it and I'm a customer, so obviously. Obviously, I understand it and it's like, no, you don't understand the incentives, the history, the evolution of it. You don't understand why certain things are the way they are. And that isn't to say that they're, they're, they all should be maintained, but there's a logic to them. And most of them can be traced to some kind of underlying decision or regulation,

• 1:07:22Ryan Holiday?

  or it evolved that way for a reason. And if you don't know it, then you could be right about knowing why it should change, but you don't actually know how best to change it. You don't know why it's particularly entrenched. You actually have to like do a deep dive into this thing way more than like, oh, it would be cool to do this.

• 1:07:41Speaker 01

  Yeah. You know, it's funny. We have a venture capital fund and the number one indicator of success in our portfolio companies is who has lived this problem for more than 10 years.

• 1:07:50Ryan Holiday?

  Yeah.

• 1:07:50Speaker 01

  And so I almost always will choose lived experience and pain is the direct driver to profit over almost anything else.

• 1:07:58Ryan Holiday?

  Right.

• 1:07:58Speaker 01

  And of course there are exceptions to this, but usually those are second or third time founders.

• 1:08:03Ryan Holiday?

  Yeah.

• 1:08:04Speaker 01

  So their lived experience is building companies and can sort of see the widget factory in every single industry. But yeah, I mean, if we, like some of our best performers, I'm like Dino, it's a Ronics. It's a, you know, autonomous ship builder. It's worth, I don't know, $8 billion now. And he was in the Navy and he saw firsthand the problem with, you know, shipping and the problem with acquisitions, because he did part of it. And so, you know, I think oftentimes there, there's like a little bit of a veneer today on being new, being young.

• 1:08:36Ryan Holiday?

  Yeah.

• 1:08:37Speaker 01

  And in reality, most millionaires are 50 plus.

• 1:08:40Ryan Holiday?

  Yeah.

• 1:08:41Speaker 01

  Most billionaires are in their seventies.

• 1:08:42Ryan Holiday?

  Right.

• 1:08:43Speaker 01

  Most people who start a business are in their thirties or forties. This is not always a young person's game. Like you're not broke, you're just early.

• 1:08:49Ryan Holiday?

  Yes. And you should be like, hey, this is the part of my career that is setting me up to be that person who is successful in their thirties and forties and fifties. What I'm doing now is learning, developing all different kinds of experiences. Like also, it's like, hey, yeah, you could be totally right about this problem in this industry and how much potential it has, but you haven't learned a bunch of the skills required for You'd actually realize that, whether it's how to lead people, whether it's managing pressure and stress, whether it's emotional maturity, there's all these other things. And sometimes you can be so right, you can have such a monopoly, or you can have such a big target that you can kind of learn those things on the job.

• 1:09:30Ryan Holiday?

  But chances are you are not ready for the thing that you think you're going to be successful at, and you you could use a lot more time learning and experimenting and all of that.

• 1:09:41Speaker 01

  I remember like the exact moment when I knew I was going to go do my own thing.

• 1:09:44Ryan Holiday?

  Yeah.

• 1:09:45Speaker 01

  And I was on a walk with my CEO at the time, and I was building out a business in Latin America. It was pretty big and successful by then. And I was like, we need to do this, and we've got to do more direct sales, and we've got to be online and a lot of the stuff that I'm doing now today. And I remember he's an older gentleman, you know, very, very wealthy billionaire, many times over, and I have a lot of respect for him. And he looked at me as I was going on my rant and said, here, we get rich quietly. We don't do it that way. And we're on a boat going right. And if you want to go left, you got to get your own boat.

• 1:10:17Ryan Holiday?

  Yeah.

• 1:10:18Speaker 01

  And at the time, I was really mad. I was like, you're an idiot. You don't get it. You're going to miss the internet, you know, me with my non billions.

• 1:10:26Ryan Holiday?

  Yes.

• 1:10:26Speaker 01

  And so I knew I had to leave. But now I look back at that moment, and I'm like, what a gift this man gave me. Because he told me like, hey, if you are really committed to this, and you already know this market and all these things, just go do it yourself.

• 1:10:37Ryan Holiday?

  Yeah. And he had the discipline not to not to be distracted by what you were saying, but also the discipline not to be like emotional or condescending or threatened by what you were saying. He could just be like, hey, this is where I'm going. I have a sense of my path, and this is the path that you want to go on. I'm not threatened by that. I'm going to encourage you to do it. But like, he's basically also saying, you have a lot to learn. Like, you have a lot to learn.

• 1:11:02Speaker 01

  And you know what? And he was right. I mean, thankfully, I went out and did my own thing. But without the, you know, five or six years working for him, I would not be where I am today.

• 1:11:10Ryan Holiday?

  Totally.

• 1:11:11Speaker 01

  And so I think sometimes you can get into a company or a job, and you'll know you're ready to leave when you're like, no, no, I know the way.

• 1:11:17Ryan Holiday?

  Yeah.

• 1:11:18Speaker 01

  And I I've seen it, and let me show you, and it's working. And they won't let you continue that way. And I hear a lot of people, that's the moment that you know you need to go try it for yourself. And then the same thing, say, hey. You might be right, I might be wrong. Do you think I'm crazy for going and trying this by myself?

• 1:11:35Ryan Holiday?

  Yeah.

• 1:11:35Speaker 01

  And I bet nine times out of 10, they're gonna say, "No, go try it."

• 1:11:39Ryan Holiday?

  Right.

• 1:11:39Speaker 01

  And if it fails, come back to me.

• 1:11:41Ryan Holiday?

  Yeah, and keep the door open because you're gonna have a million questions and you're gonna need a lot of advice while you're doing it. And that's part of remaining a student of what you do, too.

• 1:11:48Speaker 01

  Yeah, and I don't actually think you should almost ever burn the bridge, unless they are a terrible person that has done awful things that you do, that you never want to engage with. And often, I think, especially when you're a young employee, they're not, even if you think they are. You just don't understand yet because you're not a CEO.

• 1:12:05Ryan Holiday?

  Yes.

• 1:12:06Speaker 01

  And so, otherwise, don't burn the bridge. Actually, keep it there. You know, you might, it might need to be some commerce later over that bridge. You don't even have to go back, just send some stuff.

• 1:12:14Ryan Holiday?

  This is awesome. You want to do a Walks in the Bookstore?

• 1:12:16Speaker 01

  Let's do it, I would love to.