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The Daily Stoic

14 Oct 2026 · 13m · 5 chapters

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Stoicism Requires You to Stay a Student | Codie Sanchez

In short

Stoic wisdom—staying a lifelong student by reading, asking questions, getting mentors, and learning from others’ lived experience before taking big risks in business.

Guests

Codie Sanchez, entrepreneur/investor; founder of Contrarian Thinking; author of Main Street Millionaire; new book Own or Be Owned (Sept 18). She discusses scaling a business so it doesn’t depend on her, and learning from people further ahead.

Key claims

You never “get the hang of it”; wisdom is a process, not an endpoint. Don’t skip books/advice and “learn it on your own.” Trial-and-error is expensive; learn from case studies and mentors. Success correlates with having lived the problem for 10+ years.

Notable examples

Marcus Aurelius seeking Sextus the philosopher; Airbnb hosting helping her transition from corporate to full-time writing; venture/buy-business caution and need for a “mini MBA” group; example of a navy background driving shipping-profit insights (Dino at Sironics).

Written by AI. May contain mistakes.

Chapters

0:00

Travel and Local Experiences

Exploration of the benefits of travel and local interactions.

“So I have a bunch of traveling I'm doing through the end of the year on Daily Stoic Live Tour.”
1:27

Continuous Learning in Stoicism

The importance of staying a student and continuously learning in life.

“There's always some new situation, new crisis, new problem.”
2:30

Introducing Cody Sanchez

Introduction to Cody Sanchez and her contributions to business wisdom.

“little deep dive, but we had Cody Sanchez out a couple of months ago, and we walked through how each of the stoic virtues applies to business.”
6:40

Wisdom as a Lifelong Process

Discussion on the nature of wisdom as an ongoing journey rather than a destination.

“Okay, so the last virtue is wisdom, 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?”
14:00

Lessons from a CEO: The Importance of Learning

Codie Sanchez shares a pivotal moment with her former CEO that taught her the value of independence and continuous learning in business.

“And you could use a lot more time learning and experimenting and all of that.”
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Transcript

Automatic transcript. May contain errors.

0:00Ryan Holiday: So I have a bunch of traveling I'm doing through the end of the year on Daily Stoic Live Tour. I just got back from San Diego. I like to stay in the places that I'm staying. I like to book places on Airbnb so I can be like a local. I not only do some of my best writing, but I learn about things that I wouldn't have known otherwise. When I was just in San Diego, I took a walk along the water. I bumped into someone who recognized me and they told me about their favorite local bookstore, which was like two blocks from where I was staying. And I never would have known about it if it wasn't for that encounter.

0:30Ryan Holiday: It was cool to me to think that I have helped facilitate that experience for many, many people coming to Austin over the years. The first house that I bought in Austin when my wife and I first moved here, we would list it on Airbnb. And it helped me make the transition from my corporate life to being a full-time writer. So if you're going to be away, you should maybe think about listing your place on Airbnb. It can be a great way to earn extra cash while you travel. It can offset the cost of your trip or maybe even go towards whatever you're doing next. If you've got travel coming up, check out Airbnb.

1:01Ryan Holiday: Your home might be worth more than you think, and you can find out how much at Airbnb.com slash host. Welcome to the Daily Stoic Podcast, designed to help bring those four key stoic virtues, courage, discipline, justice, and wisdom into the real world.

1:21Ryan Holiday: Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. it's crazy to me right we've been doing this daily stoke thing for 10 years i've been doing this writing researching philosophy thing for 20 years and uh i know a thing or two but i'm just constantly humbled by like how much i don't know like like how first off how many new things i'm learning and then how often i'm having to learn the same lesson again and again in a new way in a new context. That's just what it is, right? Like you never get the hang of it. There's always something new. There's always some new situation, new crisis, new problem.

2:01Ryan Holiday: You have to become a student and then you have to stay a student. I talk about this in the ego book, but I talk about it a lot in the wisdom book. Like the stoic virtue of wisdom is embodied in that idea of Marcus Aurelius. Seen leaving the palace in Rome, where are you going? I'm off to see sexist the philosopher to learn that which I do not yet know. That's what it is. You're waking up every day and you got to go learn that which you don't know. You got to read, you got to ask questions, you got to listen to podcasts, got to have a mentor. That's one of the things we're going to talk about in today's episode.

2:29Ryan Holiday: You might have caught some of the previous installments of this little deep dive, but we had Cody Sanchez out a couple of months ago, and we walked through how each of the stoic virtues applies to business. Courage, it's putting yourself out there, going after it, discipline that's staying at it, justice, that's the ethics, that's the integrity, that's the values you bring to the business. And then this is wisdom. You know, how do you learn from the experiences of others? How do you make sure that you remain humble so it doesn't humble you? How do you stay hungry? How do you focus on all there is to know, not just what you do know?

3:10Ryan Holiday: And that's what we get into in today's episode. Cody is an entrepreneur, an investor, She's the founder of Contrarian Thinking. She's also the author of Main Street Millionaire. She has a new book that just came out on September 18th called Own or Be Owned, Build a Business So Good It Doesn't Need You. Again, that's something I am learning and working on. Like, how can I not be so central to everything? Because I have other priorities, I have other things going on. You know, you get burned out in some ways. How do you build a business that scales that work? And the way you learn it is by talking to and working with and modeling yourself on people who are a bit further on who have learned these lessons in painful ways and have come back to share that with you.

3:56Ryan Holiday: You can follow Cody on Instagram at Cody Sanchez, on TikTok at Cody Sanchez with an underscore in between. You follow her on YouTube at Cody Sanchez CT. I've been admiring some of the stuff she's been doing on YouTube and trying to learn from it, right? That's what this is all about. You can grab signed copies of Main Street Millionaire by Cody Sinches at The Painted Porch. We don't have signed copies of Own or Be Owned because it wasn't out yet when she came out to do it. But you can check the show notes to listen to the other episodes or watch the full episode on our YouTube channel, which I will link to.

4:25Ryan Holiday: Today's podcast is sponsored by Rayneo, a brand at the forefront of augmented reality and smart eyewear. And they are thrilled to announce their new IO smart glasses. designed to be comfortable daily eyewear ranio io smart glasses integrate powerful smart technology features that enhance your everyday life with lifelog you can effortlessly capture daily moments hands-free as a second brain that remembers what you see and experience and that allows you to stay fully present through automated journaling ai curates your day by summarizing activities interactions and highlights into a beautifully organized personal journal and with their AI multi-model subscription service, users can access Rainio AI in Gemini for free or upgrade for$9.99 a month to experience ChatGPT and DeepSake.

5:12Ryan Holiday: There's even a voice memo and AI summary feature that can record meetings and sudden inspirations and let the AI instantly transcribe and summarize them for you. The Rainio IO smart glasses are perfect for professionals, parents, or anyone handling high information density. You can check them out at rainio.com, r-a-y-n-e-o dot com. AI isn't just opening new business opportunities, it's changing the way businesses get work done. Questions they ask, the decisions they make, the routine tasks that can be handed off. That's the idea behind NetSuite Next, the next generation of NetSuite, with AI woven into the tools that your business already relies on.

5:51Ryan Holiday: NetSuite Next surfaces insights exactly when you need them, puts agents to work on routine tasks and problems, and lets you ask complex questions in plain language, like talking to a knowledgeable colleague. But technology is only part of the story. AI is also shaping how people and teams work together. That shift is underway. And that's why there is a new expert created business guide for you. It's called Aligning for the Agentic Era, how AI is changing everyday work. And right now it's totally free. It can explain how AI can reshape work across your entire organization and how businesses like yours can prosper from it.

6:29Ryan Holiday: If your revenues are at least in the seven figures, get this free business guide aligning for the agentic era at netsuite.com slash stoic. The guide is free to you at netsuite.com slash stoic. Okay, so the last virtue is wisdom, 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, 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.

7:10Ryan Holiday: 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. 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. And we have a lot.

7:43And 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 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.

8:12And 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 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.

8:29Ryan Holiday: 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. 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?

9:00Ryan Holiday: 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? 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. Oh, 100 percent. I mean, it's one of the things that keeps me up at night.

9:33If 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.

9:38Ryan Holiday: 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.

10:09You 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 five to 10 % of what he does is action. 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 pushing it off. But if you are committed and disciplined to 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.

10:46I mean, we know. We know in our group about 30 to 40 percent of people who join buy a business. The average amount of people that buy a business is like 0.03 percent.

10:56Ryan Holiday: 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 at something that you have not made yourself a student of. And the industries, 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.

11:33Ryan Holiday: 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 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.

12:10You 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. And so I almost always will choose lived experience and pain is the direct driver to profit over almost anything else. And of course, there are exceptions to this, but usually those are second or third time founders. 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 Sironics it's a you know 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.

13:05And in reality, most millionaires are 50 plus. Most billionaires are in their 70s. Most people who start a business are in their 30s or 40s. This is not always a young person's game. You're not broke. You're just early.

13:18Ryan 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 30s and 40s and 50s. What I'm doing now is learning, developing all different kinds of experience. 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.

13:59Ryan Holiday: 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 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.

14:31I 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. 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 it yourself.

15:06Ryan Holiday: Yeah. And he had the discipline 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.

15:39And 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?

16:03Ryan Holiday: Yeah. And I bet nine times out of 10, 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 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.

16:34Yes. And so otherwise, don't burn the bridge. Actually, keep it there. You know, you might need to be some commerce later over that bridge. You don't even have to go back. Just send some stuff.

From the publisher

You might have a great idea, some success, or the confidence to risk everything. But you still have something to learn.


🎥 Watch the full episode with Codie Sanchez here: https://www.youtube.com/watch?v=gTRmrzSCbaI


👉 Follow Codie Sanchez on Instagram @codiesanchez, on TikTok @Codie_Sanchez, and on YouTube @CodieSanchezCT


📚 Books Mentioned:


Grab signed copies of Main Street Millionaire by Codie Sanchez at The Painted Porch | https://www.thepaintedporch.com/


Check out Codie's NEW book: Own Or Be Owned: Build a Business So Good It Doesn’t Need You


🎟️ 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/


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