The Daily Stoic - A Stoic Masterclass for Ambitious People | Codie Sanchez

Episode Date: June 13, 2026

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 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 is an entrepreneur, investor, and founder of Contrarian Thinking, 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 and host of the BigDeal Podcast. Follow Codie Sanchez on Instagram @codiesanchez, on TikTok @Codie_Sanchez, and on YouTube @CodieSanchezCTCheck out Ryan’s episode on BigDeal by Codie Sanchez 👉 Apple Podcasts, Spotify, YouTube📚 Grab signed copies of Main Street Millionaire by Codie Sanchez at The Painted Porch | https://www.thepaintedporch.com/🎟️ DAILY STOIC LIVE | Ryan Holiday is coming to a city near you! Grab tickets here |  https://www.dailystoiclive.com/🎙️ AD-FREE | Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎥 VIDEO EPISODES| Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemailSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Welcome to the Daily Stoic podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world. 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 is 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, and 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. 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 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 an opportunity to practice virtue, right? I think the Stoics would have found business really interesting. I mean, Zeno 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. Cody 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, 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 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 TikTok, Cody underscore Sanchez, or on Instagram at Cody Sanchez. She previously worked at Goldman Sachs and Vanguard, and now she buys and sells and invest 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 is Cody and I talking about courage and discipline and justice and wisdom. Okay, so what I thought we could talk about, so the four virtues of stochism 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 and how you understand them or what you understand them to mean. 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 is 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. Yeah, well, I think, you know, entrepreneurship is probably one of the scariest things a human can do because you wrap your identity in who you are as a business person, as an entrepreneur, an author. And so when that gets rejected, you feel like you are rejected yourself.

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. That you're a person who does hard things. 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. Yeah. You know, he's a former Navy SEAL and military man. So when I say things, like, we're going to go

to war. He's like, you're literally not, you know, you give business advice. You're okay. Everybody's going to be fine, more or less. 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, I'm 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 going to quit my job and start a business. And you're like, but what if I fail? then you would just go get another job.

Which is where you all are ready. Yes. 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. Right.

You know, maybe a one-way door to decide to go swim with great white sharks without a cage. 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, this is a one-way door or a two-way door. 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. 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 realized. 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. 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 has. had to come from Iraq, where he was a translator, to the U.S. He worked with Chris. So when Chris got him out of Iraq, he came to the U.S. 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 there will be contextual change? And he said, no, he's like, I bagged groceries because it would help me. 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. Yes. You know, maybe later. It could be real risk. 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, and, you're, and, you're not thinking about. And, And so, yes, obviously 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 so you have this perception of the risk that you're taking, and it's actually not based on anything real. No, it's not. And, you know, it is always fun to say like the what if game. Yeah. Like sometimes when I'm really scared in the beginning, like when I first started a business, I wrote down all the things it could go terribly wrong because I was really scared that I might leave Goldman Sachs and States 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? Yeah. 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?

And he was like, yeah, sure. Pick your rule. So at that point, you're like, how much of the things that I'm scared are going to happen are basically just ghosts in the mind. Well, do you know the acronym for fear? No. They talk about in recovery. It's false evidence appearing real. It's true.

And so the idea of going, okay, what is the worst case scenario here? 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 what you do is, yeah, you write it down, where 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 so I think people tend to think of entrepreneurs as just plunging into the unknown, not caring about the risk, but actually what happened is they've 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 or Z, yes, $50,000 is a lot of money and it can be painful for that to go away. But 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, just a year behind my peers, is 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 notice 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 knows. They might ask where I to school because it's cool for us to talk about. It turns out we both went to this college or that college. But like, no one is concerned that you are one year behind someone else because you took a risk on something. And by the way, we're not even getting into the upside of you took that risk in the whole trajectory of your life went in an awesome direction. 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 the work. 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 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. Well, that's the problem with imposter syndrome, right? And it is presuming way too much interest in you. Like, no one is, no one is,

that you're an imposter. 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 Mark Srealius 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 his 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 to me, that's 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. 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, you're probably heading.

Those are all bad signs. Like, a boxer who steps into the ring and it's not nervous is going to get destroyed because it means you have underestimated your opponent and overestimated your abilities. 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 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? Like, okay, these days I do think that we sort of idolize the people who just jump off the bridge and somehow figure out how to build the airplane on the way down.

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. 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. 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? The number's like 10. You know, you have, you have, you've, have blank fine, you have Bernanke, you have 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? 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, give it advice. I'm going to do it again and again. And 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. And I walk by his like $80 million house all the time when I'm in San Diego. It's 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. 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. I remember when I decided 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. it. And I went and I called my boss and I said, hey, I'm going to leave to be a writer. I'm 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 salary life. And actually, if you're really

good at what you do. Oftentimes you'll have enough leverage 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 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 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, 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 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 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 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 less scary. 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. Yes. Simultaneously, if you're the best performer in the place that you are, you're an A player and you keep crushing it, the last. The allowances you get are wild. Right. 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. Right. 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, hardest working people you can find in the world. that take a bunch of risk so you can coattail their risk.

Or make them dependent on you in something. Like, if you are a part of their operations and it is expensive for them to replace you, you suddenly have leverage. Yeah. And then you have a power. That leverage becomes a powerful ally when you want to do your next thing. Yeah. 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 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 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 to be able to continue to fund the first deal. 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. 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 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.

Yep, especially in the age of AI. Yeah. Like I think, you know, the other thing with courage is to not just be a copycat forever trying to get rich quickly. Yeah. 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. Yeah. 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... There's not much of a moat there. If it's as easy as you said, then it's easy for everyone. Yes. Yeah, exactly. And it's true. So have some courage to do something creative, too. The more people doing it, the more competition you have, right? Like, I think Peter Thiel's talked about this, but 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. 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 to cross 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. 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?

Yeah. You know? 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're going to know, mine is $500, people are like, whoa, what's with this guy?

So now you're standing alone, which requires courage. And then, yeah, the risk of taking the certain way for the, on the, certain 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. We'll get to justice as the other virtue, but it's like you're not doing anyone any favors 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 keep the price of this low so school children can afford it. You're, it's, you're, you're,

These are rounding hairs for huge companies and you're just refusing to charge what you're worth. I think it comes down like, you know, you were just like the rest of us, you 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? We just have these weird program ends. 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. 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. 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've got to charge more. 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. So by remaining small and keeping things on this sort of shoe string, like perpetually on the verge of going out of business, you're not able 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 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 when they're 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 are you pricing your widgets at, but like,

what your hourly rate is as a freelancer, what, you know, you'll accept 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 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. Yeah, totally. You know what silently kills sales teams? The inability to see what's happening in their pipeline. And part of the reason they can't do that is because they use software or CRM that's so complicated that people don't even log in.

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I don't know if I call them kids, but some of the Gen Z kids on my staff had to tell me about it. They really love it because you can find vintage stuff and collectible stuff. I was looking at some videos of people selling vintage band teas and records and watches. And it's real people selling. Like if you're going to an estate sale or a really cool trendy shop, not, you know, overpriced stuff, not produce stuff. There's no ads, no marketing. And people are on there explaining their stuff, why you'd like it, what's cool about it, where they got it. Like I love buying stuff on auctions.

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and they're not just browsing, they're bidding, and buying, and coming back. So you can go live, show off your projects, and turn that into real income. People selling on What Not sell 10 times more than on other major marketplaces, And that's because you're not just listing products. You're building real connections with buyers. Download the What Not app today and get free shipping on your first order. Just search What Not, W-H-A-T-N-O-T in the App Store to start scoring amazing deals. 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 marking compensation, it's a lot less scary. Because you go, hey, I don't know. I mean, I've had people do it to me. Go, I would like a raise. I go, yeah, me too. Yeah, sure. You know? And this isn't just why I saw in glass door, the range is here to here.

Because your boss also knows their shit. Yeah, exactly. And they go, nobody, I could walk across the street and verify in two seconds that this is not actually what here and here. No, no. If you can get that over there, by all means, I'll give you a recommendation, right? So you have to know your real shit from real work, not just, you know. Yeah, and what your value is. I mean, I think a lot of getting what you're 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. I'm like, 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 want to, 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. Sure. No problem. It's not that difficult. The problem is most people just want to say, I want a salary increase, which is a very quick way to say, I just want you to pay me more and me to have zero risk. Yeah, I would like to keep doing the same work for more money, which is, of course, the deal everyone wants.

It is. Yeah, me too. Some days, you know, find me on the right Tuesday. I want to go back to it. Okay. So the next virtue for the Stoics is this idea. Sometimes it's rendered as temperance, which is moderation. I prefer to see it as self-discipline or self-s sort of ownership in the sense of being in command of your emotions, your desires, your urges, your envy, all of these things. So talk to me about why that's an important skill as a business owner. 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. 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. 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. 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 is reasonable or when you could at all want to. 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 going to 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. Yeah. And it's not my desired state to sleep on a factory floor. 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. It calls it like demon mode or whatever. Whereas like someone with more of a plan or more of a corporate structure around them or could delegate better, wouldn't have to do that. Yeah. But I get your point, which is like, you got to do the work. I think it comes down to what do you want to build. Yeah.

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. Right. Like Jeff Bezos, to me. Also pretty driven. Yeah. 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. 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. And you said it's pretty miserable to be him. Right.

So I don't think you have to be that. In fact, I think you should love the business that you built. Right. And because most people don't want to be him. Right. 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-disciplined clones in the organization. I guess that'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. Yeah. 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 one's you.

Yeah. I do think there's this idea of 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 senator. where he says, no one is fit to rule who is not first ruler of themselves. And so they think, like, I think that being in charge, running a big business is 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?

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. Oh, yeah. I mean, I have two sides of 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. 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. Yeah. 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. And we don't have to have this hustle porn misery addiction to trauma bonding over being an entrepreneur. There's two sides of the idea of discipline. So discipline isn't just I work harder. I sleep less.

I push my boundaries more. it's also the restraint to go, this is what we're doing this year, no more and no less, right? where these are the hours that I operate in, these are my priorities. One of the things you find when you have, like we open this bookstore a couple 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 bookstore. which would 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. I'm not going to jump on every problem that comes up. I'm not going to do every interview that comes up. 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 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 what your limits are. 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. That's what you would tell in New York Times reporter because you want them to write a story about you. 100%. Yeah. And we would both know because we've written titles before. 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. One of 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. It's like the discipline even to like let go of some of the control. These are all, we tend to think of discipline as just working harder and doing more. Yeah. And it's much more subtle than that. Oh, no. I mean, God, if you want to win, you have to say no to so much, it feels uncomfortable. Yes.

And I do it nonstop. I mean, the idea that doing more is going to make you win is I think why so many entrepreneurs are miserable. Yeah. Because they have bought into the idea. If I just do one more, I will become better, bigger, richer, etc. And in fact, it's usually what are the 10 things you need to stop doing right now that are burning up time that you can't even picture? And one of the two things that if you did them would make everything else meaningless.

And if you find those, then you really win. Yeah. And the discipline 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. And you might not get to that. that point. 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 detention, you know, 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. Is you balanced out by another person? They're like, what are you doing? Exactly. Yeah, this is crazy.

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. They're, they also tether you to reality. 100%. You're sounding like an insane person right now. Yeah, yeah. 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?

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, you know, spouses that sign up for that, like, they need a medal too. Yeah. 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. And he is also. And he's, you know, something like a P&L or a spreadsheet that you're not going to remember in 50 years. Chances are if you are driven, if you're talented, if you're successful, if you've built something, chances are you need more of a check than you do an enabler. It's so true. That's a good point, actually.

You don't need encouragement. You have plenty of that. 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? Right. 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 oars at my company. But if all you do is row a left or on a boat, you go on a circle.

Yeah. You have to row left and then right and then left and then right. And that is the beauty of partnership. 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-sided, 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. It's so funny. We actually, we created something called the boardroom, I can turn 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. And I was scared of the downside of boards, which is that they can be non-a-scentive 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 realize 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 peers, you need advisors, and then you need people that are like 10 or 20 years ahead of you. And with those three things,

you can just move faster because you can steal people's 10,000 hours. Yes. All right, so I got these two talks in Portland and San Francisco in early June, and I've got to figure out what I'm going to wear. You know, normally I just wear a heavy metal shirt and running shorts or something,

but I can't do that on stage. And I can't wear the same stuff on stage for all of the events because it would screw up the video. And that's why I'm shopping on Quince right now. I want something that looks good on stage, that I'm not going to sweat through. It's not going to get super wrinkled. Quince has got great t-shirts.

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Go to quince.com slash stoic for free shipping on your order and 365 day returns, and now available in Canada, too. That's Q-U-I-N-C-E.com slash stoic for free shipping and 365-day returns, quince.com slash stoic. 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 with that freedom comes the sort of voluntary responsibility, right, which in a way makes it harder because it's like if you lived 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 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 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 these are my environmental standards. These are my humane standards for like meat and stuff like that. This is the benefits I want to provide. This is how I want to give back. So he's saying, you, the 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 had to say. Yeah. Well, 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. Yeah. 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 small business employee happiness is 40, 60 percent 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. And that, I think, is where capitalism's got a little script. really, 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 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. Yeah. And so I'm curious to see, because this is a little technical,

but, you know, we've seen since basically the 1990s with 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. 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've 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. And because of that, we have really bad incentives. And environmental and standards are really hard to care about

when you work in three-month cycles. 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. Well, I would also say 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 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 U.S. costs $20 a T-shirt and making them in China cost $4 a T-shirt. And now all of a sudden this principle costs you money. And you might think, okay, so the business says, we'll obviously go with the cheaper one. 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 other people, then all of a sudden you have to, you get to decide, right? And you have a responsibility to decide. And so to me, there's something really empowering about running the business because it's like you don't control the world. You only have one vote 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. Or not. And turn out your full of shit. And you get to see the consequences of actions. Yes. Because a lot of times you can say things that sound great and are idiotic in life. 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. Yeah. So is that good or bad? Yeah. I don't know. But there's actually data and math. You can't have everything all at once.

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. Yeah. 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. Sure. 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.

I don't want to go to another Starbucks. I want to go to the coffee shop next to Ryan's store and Bastrop, 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 out right. 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. Yeah. And so I can't. You roll them up. You create a centralized structure. You eliminate inefficiencies. 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 at 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? If I took two 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-thousand-th the cost of a business that you buy. And so you do have to pick, that was my stance. Yeah.

And I think the cool part about when you run a business, pick a stance and see what you're capable of holding the line of. And how strongly do you actually believe in the things? I think every company should have a creed. The mission statement, there's lots of ways to do it. A lot of them are bullshit. I've seen them all. Everybody thinks you need to throw one up on the wall.

I believe they deeply, deeply actually change how a business operates. And ours, we have a contrarian creed. There are 13 rules, 13 because we believe in making our own luck. And the first one is 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 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.

Well, and as I say, it's not a principle until it costs you something, right? And I told this story. And for many years when I talk about the Stone Furtures 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, it's bad for people and we're going to stop. So they do. And it costs them, I don't know, a billion dollars a year or something in revenue. And people are like, why?

Like 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 so they're like, look, 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 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 smoked less cigarettes because they were harder to get.

So they make this decision that's probably mostly about branding and, you know, reputation and if they got a lot of press when it came out. But actually, they affect 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 that's been in business since the 40s and it went up for sale. My wife and I ended up long story short owning this thing. Not our dream, not what we expected. We are 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 problem. And now I have to go, fuck, okay, I don't like this. I don't want this. And so you take them out. And then what you're actually doing is just putting a giant hole in the, in the, in the, in the P&L of the 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. 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 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 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 to put up or shut up. 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 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 because that just tends to happen. It happens a lot with women CEOs still. You let go a certain number of people. Some percentage of them are disgruntled.

100%. 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 truth. is if you hang out with Cody over here and you hang out with Cody online, she's kind of the same thing. Yeah. 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've 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 like the Warren Buffettism, which is you can make a mistake with a dollar, 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 businesses is if you lie, cheat, or steal, or you hurt a reputation. Yeah. If you make mistakes, if you want to leave, if you give me hard feedback, even 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. Yeah.

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? Yeah, I did a piece a couple 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. Yeah. And I think early in my career, there were things I did for money. that we're not in accordance with my values and the discomfort from that or the 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 to try to genuinely do your best to bring like how you operate in accordance with like who you want to be. Mark Shrewis has this line of not doing anything that requires curtains. 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 got to change. 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. Yeah.

And we just have a hard line. That is one of the fireable offenses. Yeah. Yeah. And it's what if they saw it? And also, what if they realize that's what we think? of them. Yes.

Right. 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 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 a customer is going to drive you fucking crazy at some point. Well, and then it presents you, like when we say the obstacles the way, the opportunity

there is as expensive as that is in front of. as frustrating as that is, it's also a chance for you to say to everyone else, hey, this person, 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 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 cultural or sexual harassment was prevalent and that people were saying things that, like, by the way, when the, when the lawyers discovered them in discovery, they were, there was a vulnerability that, right?

Like you, you, the decision to go, hey, I'm going to let this person go, even though they drive values 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. 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. Oh, sure. 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 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 at a place where you cannot say that to your boss, you should leave.

Yeah. Hey, I thought our values, we only make stuff in the U.S. but like here we are the people who make our boxes doing it cheaper X, Y, and Z is you, you, 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 I, if I, if 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're concerned about doing something that's right and getting yelled at for it. She's like, if he doesn't respond well, he shouldn't be your agent anymore. And like, that's a really bad sign. 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 it. And it 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. Yeah. 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. 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. Yeah. 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. And if they do say no, they've told you a lot. Right. If they say no, you say that's not for me. Or you, you know, do 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 a way to argue for that doesn't work for me. Yeah. And so you might have to leave. You might have to change, but you might also be shocked how often it works. Yeah. No, I have a talk about this in the courage book. I had a moment like that where I went to my boss when I was at American Parry. He asked me to do something I thought was an ethical. And I was like, I don't want to do that. 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? Or you might even have something to 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 performance review and we should probably let her goal go and 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. Okay, so the last virtue is wisdom, which I think people tend to think of is 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, it's not this place that you arrive. It's more of a process. It's a

byproduct of learning and experience and mentors and all these things. But it is weird how often people will be like, I'm going to 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. 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. Yeah. 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. 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 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, it worked. 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. Yeah, 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 exposés and articles about out, 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 aren't 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 did things not last in this town? 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

to open the 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. Oh, 100%. I mean, it's one of the things that keeps me up at night. If there's one thing that scares me, it's that we talk about buying businesses on the internet and then somebody just goes and buys one. Yeah. And then they go, what the fuck did I just do? Yeah. 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. 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, of course isn't enough. You have to actually have real humans and almost treat it like a mini MBA. 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. And then, you know, let's call 5 to 10 percent of what he does is action. And, you know, 90 to 95 percent 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 pushing it off. But if you are committed and disciplined of 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%. Yeah. 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. It's very unlikely you're going to be successful. It's something that you have not made yourself a student of. And 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 disrupt an industry that I, by the way, know fuck all about. Like I read an article about it and I'm a customer, so 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 all should be. be maintained. But there's a logic to them and most of them can be traced to some kind of underlying decision or regulation 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. Yeah. You know, it's funny. We have a venture capital fund. And the number one in indicator of success in our portfolio companies is who has lived this problem for more than 10 years. Yeah. And so I almost always will choose lived experience and pain is the direct driver to profit over almost anything else. Right. And of course, there are exceptions to this, but usually those are second or third time founders. Yeah. 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 at Seronics, it's an autonomous shipbuilder. It's worth, I don't know, eight billion dollars 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's like a little bit of a veneer today on being new, being young. And in reality, most millionaires are 50 plus. Most billionaires are in their 70s. Right. Most people who start a business are in their 30s or 40s.

This is not always a young person's game. Like, you're not broke. You're just early. 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 30s and 40s and 50s. What I'm doing now is learning, developing all different kinds of experiences. 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 to 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. But chances are you are not ready for the thing that you think you're going to be successful at and you could use a lot more time learning and experimenting and all of that. I remember like the exact moment when I knew I was going to go do my own thing.

Yeah. And I was on a walk with my CEO at the time. And I was building out of 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 Trambo. 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. 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 yourself. 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. You have a lot to learn. 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. 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. And 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? And I bet nine times out of ten, they're going to say, No, go try it. Right. And if it fails, come back to me. Yeah, and keep the door open because you're going to have a million questions and you need a lot of advice while you're doing it.

And that's part of remaining a student of what you do too. 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 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. Yes. And so otherwise, don't burn the bridge.

actually keep it there. You might need to be some commerce later over that bridge. You don't even have to go back. Just send some stuff. This is awesome. You want to do a walk through the book? Let's do it. I would love to.