12 Lessons From 12 Months Owning A Bookstore

It's going to take longer than you thought, but it will be worth it in the end. By the first week of March 2020 the world was entrenched in a pandemic. What began with such excitement for Ryan Holiday and his wife Samantha ended up taking much longer and costing way more than they had expected. In this video Ryan breaks down the 12 most important lessons that he's taken away from the first year being in business. Sign up for Ryan Holiday's Reading List Newsletter: https://ryanholiday.net/reading-list/Get the Ernest Hemingway "First Draft" Tee at the Painted PorchCome visit The Painted Porch on Main Street in Bastrop, TX or shop online at https://www.thepaintedporch.com/Sunday can help you grow a beautiful lawn without the guesswork OR nasty chemicals. F​​ull-season plans start at just $129, and you can get 20% off at checkout when you visit GETSUNDAY. COM/STOIC. Sign up for the Daily Stoic email: https://dailystoic.com/dailyemailCheck out the Daily Stoic Store for Stoic inspired products, signed books, and more. Follow us: Instagram, Twitter, YouTube, TikTok, FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. 📢 Share | ⚙️ Manage Subscription

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

• 0:06Ryan Holiday?

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

• 0:49Ryan Holiday?

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

• 0:55Ryan Holiday?

  Hey, it's Ryan Holiday. Welcome to another Weekend episode of the Daily Stoic Podcast. As you know, Stoicism is a philosophy you try to actually apply. You try to actually use, whatever it is that you're doing. Of course, I write about Stoicism, but I have to use it in my life as I write about Stoicism, right? Whether I'm putting out a book, or working on a book, or, you know, dealing with the heat here in Texas. I try to think about how to use Stoicism the way that the Stoics used it, which was on big problems and little problems all the same. And as you know, the big sort of project of the last couple of years of my life is not just this Four Virtues series I'm working on, but this bookstore I opened here in Bastrop, Texas, in the middle of the pandemic, when it felt like the world was falling to pieces.

• 1:40Ryan Holiday?

  And over the last year or so of it being open, I learned a lot about business. I learned a lot about myself. I learned a lot about my wife. And I, of course, learned a lot about applying Stoicism to problems, big and small. In today's episode... I want to give you a bunch of lessons that I learned in that process, where you, you know, you write and you study and you think about Stoicism, then you experience something and the wisdom of it, that how it works, comes to you, you come to understand it in a different way. Of course, that's what Marcus Aurelius means when he says that we never step in the same river twice. And I came back to a lot of these Stoic teachings and understood them from a new perspective, a new angle in so many ways.

• 2:24Ryan Holiday?

  And of course, Stoicism all traces its roots back to a bookstore, where Zeno is introduced to Stoicism and philosophy, at a bookstore after washing up in Athens. It's fascinating little story, which we dig in today. But in today's episode, I wanted to give you some important lessons that I've learned from the Stoics, from life, running this little bookstore here in Ambassador, Texas, where I am recording right now. And you are welcome to come anytime. We'd love to see you. We've got a great philosophy section. And it's called The Painted Porch, because that's where Zeno founded Stoicism, after that experience in the bookstore. But without further ado, here are 12 lessons from 12 months of owning a bookstore, my bookstore, The Painted Porch, which wouldn't be here without Stoicism,

• 3:08Ryan Holiday?

  and wouldn't be here without the many of you listeners who've come out and supported it. Enjoy.

• 3:15Ryan Holiday?

  It always takes longer than you think it's going to take. That's Hofstadter's Law. We had this idea to open the bookstore in the fall of 2019. We got really serious about it in the late winter, early spring of 2020. And we thought maybe we'd be ready by the summer of 2020. And then there was a pandemic, and that pushed us a full year. Then it took many, many months to get up and running. And then every time we thought the pandemic was, was over and things were about to go back to normal, you know, it never went back to normal. And the idea is, if you think, starting a business, doing anything is going to be easy, that it's going to be straightforward, that it's going to be clean, like, you're fooling yourself. It always takes longer than you think it's going to take.

• 4:00Ryan Holiday?

  One of the things you learn doing a business like this, doing anything, is that you have to be really patient. It's going to take so much longer than you think it's going to take. And if you're rushed, if you, if you expect it now, if you can't pass the marshmallow test of delaying gratification and, and deferring things into the future, you're just going to get crushed.

• 4:22Ryan Holiday?

  There's this great Hemingway line, we actually have a shirt of it I love, and I have a print of it on my wall. It's one of my favorite all-time quotes. Hemingway said, "The first draft of everything is shit." I'd never done something like this. I love how it is now, but this wasn't how it was a week in, two weeks in, six months in, a year. And it wasn't how it was when we opened. It's been a continual process of improvement and growth and making changes. So you have to be able, you have to be comfortable starting small. And the problem is when you have really high standards, when you expect a lot of yourself, it's hard to get comfortable with something that's kind of crappy or mediocre or not all the way there. So when you say "the first draft of everything is shit," and I love the print and I love the shirt,

• 5:05Ryan Holiday?

  and you can check it out, we sell them here at the store, of course. Don't demand perfection of yourself early on. Give yourself the permission to experiment, to try. It's not perfect the first go around. No business is everything it could or should be on opening day. You have to be comfortable getting better as you go.

• 5:28Ryan Holiday?

  So I don't agree when people say money is the root of all evil, but money can be a distraction. It's not usually the best way to measure success. So like when we did this bookstore, The Painted Porch, right? It was obviously not to make lots of money because there are so many better, easier, cheaper ways to make money in this life. So you have to understand how you're going to measure the success of what you do. And almost always, money is not that thing. If this makes no money, if it loses money, if it loses obscene amounts of money, it goes out of business. We can't continue to exist. Profit is fuel, it's what makes the car go. But it's really important that you think about how you're going to measure what you're doing. We wanted to think about impact.

• 6:13Ryan Holiday?

  We wanted to think about whether it improves our lives, whether we have fun doing it, whether we help bring books into the world, whether we make this community better. You have to be careful that money doesn't creep in and corrupt or distract you from what you're trying to do or how you should be trying to measure success.

• 6:37Ryan Holiday?

  There's never going to be a shortage of reasons why you can't do something, why it's too expensive, why it's too hard. So one of the things I did while I was kicking this around is I looked up like, "How expensive is it to start a bookstore?" It was like hundreds and hundreds of thousands of dollars, like way more expensive than I could possibly afford. But then I wanted to question whether that number was real. So what I did was I went and I looked at how expensive it was to start like an e-commerce business, like what Daily Stoic is. And they said it was hundreds of thousands of dollars more than I'd spent to start that business. And that was really helpful. It's like, oh, these people don't really know what they're talking about. Or that there's a cheaper, a different way to do it. You don't have to do it the way that everyone else does it. So when you get criticism, when you get information, when you get facts, and of course, you have to look for those things.

• 7:22Ryan Holiday?

  But you also have to take them with a grain of salt. You have to really look at them. You have to put them up to the test, as the Stoics say, to find out which ones are real, which ones are counterfeit, which ones you can trust and which ones you realize are not fully accurate. So that was really, really important. It was questioning some of those assumptions, the facts on the ground, and getting to the real core of how it was. And it turned out it was still very expensive to start, but it wasn't as expensive as those people said it was. And it actually was doable for us to do it.

• 7:55Ryan Holiday?

  When I was thinking about opening my bookstore, I asked Tim Ferriss, I said, "You know, is this something I should do? Am I crazy? Am I going to lose all my money? Is it going to blow up my life? I really want to do it, but I'm not sure." And he said, "Think about it as an experiment." He said, "How are you going to know if it's something you want to do if you haven't tried doing it?" And so the decision to see it as an experiment, not as a permanent, forever life choice, was so freeing because it allowed me to go into it knowing, "Okay, for the next two years, this is something I'm committed to, but I can change my mind after that." And so this idea of seeing everything as an experiment is totally life-changing, and it's what made doing this bookstore possible.

• 8:39Ryan Holiday?

  People talk about like trusting their gut or whatever, but that's something you have to earn. I talk about this in Ego is the Enemy. Like, there's a difference between confidence and ego. Ego thinks like, whatever I want to do, of course, I'm going to be successful. I'm great. Confidence is something you earn. Something you earn over time. It's something you earn by having an idea, bringing it into reality, learning what you're capable of, learning what's possible, learning why you do deserve to trust yourself. On the other side of this, having done this scary thing, having done a thing that a lot of people said it wasn't a good idea, you're like, oh, I can do this. I'm capable of this. Seneca says, like, I pity the person who's never gone through adversity, who's

• 9:21Ryan Holiday?

  never done anything difficult, because they don't know what they're capable of. The greatest wealth that comes out of this experience is that trust and that confidence and that sense of what I'm capable of.

• 9:34Ryan Holiday?

  At my ranch here in Texas, we've got about 40 or so acres, which I don't obviously manage the way one would manage a lawn. But then there's a little yard around the house. And because of all the different grasses, because the animals sometimes try to get in there, and then because of the immensity of the rest of the yard we have, it is not the easiest yard to take care of. And that's why we've been customers of Sunday, well before they sponsored the podcast. Traditional lawn care lays down like 90 million pounds of pesticides each year. Sunday is different, and they're on a mission to change how people care for their yards. Sunday's different. You don't have to choose between having a beautiful yard and keeping your family out of harm's way, which I also have to think

• 10:19Ryan Holiday?

  about because I've got chickens that walk around the yard, and I've got my dog, and sometimes we've got baby animals. We can't just dump your regular pesticides and stuff on there. Sunday can help you grow a beautiful lawn without the guesswork or the nasty chemicals. Their custom plans include fertilizer and everything you need to easily care for your lawn with ingredients like seaweed, iron, and molasses. You can feel good with kids and pets being around. All you have to do is visit getsunday.com, put in your address, and their lawn analysis tool does the rest. Then they use soil and climate data to create a personal nutrient plan delivered to your door when you need it. And you just attach this ready to use pouch to your garden hose and spray. It takes less than 15 minutes. Best of all, it really works. Sunday is offering

• 11:00Ryan Holiday?

  our listeners 20% off. Full season plans start at just $129 and you can get 20% off at checkout when you visit getsunday.com/Doak. That's 20% off your custom plan at getsunday.com/Doak.

• 11:15Ryan Holiday?

  When I first started my reading list newsletter, this would have been 2008, 2009. The idea was that I wanted to celebrate other people's works because I didn't have any of my own books. I thought maybe that by celebrating other people's works, by saying, "This is a book that will change your life. This is an amazing book," I could build a relationship with people that later, years in the future, if I ever did any of my own books, they would know that I have good taste or judgment, that I could buy myself from them by putting out value into the world, eventually earn the trust or the respect that when I came out with one of my own books, they would at least know that I know what a good book is. To me, the bookstore is an extension of the idea of celebrating other people's work.

• 11:58Ryan Holiday?

  And when you do that, when you create value for people, when you celebrate other people's work, when you're generally a positive force in your industry, in your space, you develop a reputation. People want to support you. People want to help you. And so now, when I say, "Hey, buy this book from the painted porch," people have been buying books that I've been recommending for 10 years. They trust me. The world is not zero sum. The more you help others, the more you help yourself.

• 12:24Ryan Holiday?

  This is a note I wrote to myself when we were opening the bookstore in the middle of the pandemic. I said, "2020 is a test. Will it make you a better person or a worse person?" If it makes you worse, if it stresses you out, if it tears your relationship apart, if it makes you bitter or frustrated with people, then it doesn't matter how successful it is. It's not successful. I just wanted to think about as I was going through it, like, what does success look like? And we just decided that success was going to be becoming more community minded, becoming more responsible, becoming better organized, having more fun, like making a positive contribution. We didn't want to contribute to the problem. We wanted to contribute to the solution. That's community. That's public

• 13:08Ryan Holiday?

  health. That's all that stuff. If you succeed, but it comes at the cost of happiness, or... Other important things in life, it's not success. So that was just something I thought about. That was the test that I wanted to remind myself of over and over again. Will this make you a better person or a worse person? If it makes you a worse person, what's the point? It would be wonderful, of course, if marketing didn't have to exist. If things could be bare-boned, if presentation didn't matter. That's just not how life works, never has and it never will be. And like, that was something we thought a lot about at the painted portrait. I think one of the best decisions we made, and it's a lesson for me. We put up this book counter. This is like 2,000 books.

• 13:53Ryan Holiday?

  It's 20 feet tall. It weighs 2,000 pounds. It's 4,000 nails and 40 gallons of glue. Like, it was this whole creation. It's like an art piece. But it's the number one thing that people come into the store and take pictures of. People want experiences, right? Like, if they just wanted price, if they just wanted ease, they'd buy online. It was not cheap to do. I'll tell you, it was hard. It took forever. We had to solve all sorts of logistical problems to make it work. But it's also probably one of the single best marketing and business decisions we made in the whole store. Do interesting stuff. Do stuff that commands attention. How you make it stand out, how you draw attention like a magnet. It cannot be underestimated. There's a great line from Peter Thiel.

• 14:38Ryan Holiday?

  He says, "Competition is for losers." The point being, when you're doing something, you can kind of see how everyone else is doing it. You can see how it's supposed to be done. And there's a safety and a security in that because it's a well-trodden path. But that's not really where success comes from. When you want to succeed at something, you have to find a way to differentiate yourself. You have to find a way to do it in a way that no one else is doing it. The way that only you can do it. The big decision on the bookstore, it's a lesson that I've learned over and over again, but it was really codified here, was like, I didn't want to be like every other bookstore. Most bookstores have thousands and thousands of books, like between 10,000 and 15,000 books. But what we decided here was we'd have like a couple hundred books, only my absolute favorite books,

• 15:24Ryan Holiday?

  the books that I put in my reading list email, which I've sent out for like a decade now. It would only be those books. I think the lesson over and over again is, don't compete with other people. Do your own thing. You don't need to be first. You want to be the only. You want to be the only one doing it. You want to have a unique proposition. You want to have something that only you could do. And that's what makes you stand out. That's what makes you special.

• 15:51Ryan Holiday?

  A lot of people don't know that Stoicism was actually founded in a bookstore. Xeno, he's a successful merchant. He suffers a shipwreck. He loses everything and he washes up in Athens completely penniless. And he ends up in a bookstore. And there in that bookstore, he hears the bookseller reading the works of Socrates. And it's there, he falls in love with philosophy. He falls in love with the idea of this sort of philosophical mentor that was Socrates. And he goes up to the bookseller and he says, "Hey, where can I find a man like that?" And the bookseller says, "Well, look right there. And there was a guy, a philosopher, walking by named Krates." And this becomes Xeno's mentor. And shortly thereafter, Xeno founds his own philosophical school, which becomes Stoicism. Sto apo kiloe in Athens is where he founds Stoicism.

• 16:36Ryan Holiday?

  That's the name of my bookstore, The Painted Porch. He realized in that bookstore, hearing the works of Socrates, that a bookstore was a place to talk to the dead. So many of the authors in this bookstore are dead. Like, look, here's the Indian. Right, there's a 2,000-year-old book. Here's Epictetus, a 2,000-year-old book. Here's the Odyssey. We don't even know how old this is, right? But you can talk to those authors as if they're still alive. And I think the real lesson from opening a bookstore, the power of books to me, remains that idea that Xeno got 2,500 years ago. The idea that through conversations with the dead, talking to the wisest people who ever lived, who are no longer with us,

• 17:19Ryan Holiday?

  but survived to us in the form of books. That is the secret to wisdom. That's the wonderful thing. And over and over again, even when things were really hard, I just turned to books, which I loved. I continue to have those conversations with the dead. To me, that's what makes bookstores so powerful.

• 17:39Ryan Holiday?

  You might notice I'm not at the bookstore for this one, and that's because the bookstore is closed. All our employees are out sick. We're not able to be open. Is it going to be five days of being closed? Is it 10 days of being closed? How much money is it going to cost? I don't know. I know that there wasn't anything we could have done to avoid this. We were immensely safe. We took every precaution. We even, we were controversial at how many precautions and protections we put in place. My conscience is clear, but that doesn't change the fact that it affects the business. But, but this is life, right? In The Obstacle is the Way, I quote this Haitian proverb that I like, that behind mountains, there are more mountains. That's just how life is. You don't overcome one obstacle. You don't get through the first year of your business, and then you're magically done with obstacles.

• 18:25Ryan Holiday?

  That's not how life works. Life is one obstacle after another. You have to keep going. And, and that's what we're going to do. We're not judging the success of this business purely in dollars and cents. What matters to me is, are the employees okay? What matters is, are we doing the right thing? Are we acting in accordance with our values? Are we doing what's right for the community? So we'll have to endure this. We'll have to eat this. And, and that's just life. That's just business. We'll take it day by day. We'll get through this. We won't be deterred by it. We'll continue to do the right thing, which is all a person and a business and a stoic can do.

• 19:00Ryan Holiday?

  Thanks so much for listening to the Daily Stoic Podcast. If you don't know this, you can get these delivered to you via email every day. Check it out at dailystoic.com/email.