My wife and I were sitting at a cafe in Bastrop, Texas, looking across Main Street at an empty historic storefront.
“You know what would be amazing there?" she said. “A bookstore.”
We started construction on The Painted Porch the first week of March 2020.
Somehow, we didn’t lose all our money. It didn’t blow up our marriage. It’s actually been a great experience and, even more surprising, a pretty good business too.
Five years in, I’ve learned a lot—about business, about books, about myself. Here are some of those lessons:
Crazy can be a competitive advantage. Opening a physical bookstore in 2020 seemed crazy. Not just to me—everyone said so. Retail was shifting online, books were becoming digital, the pandemic was raging, bookstores were closing—not opening. But that’s exactly why it worked. It was crazy because no one else was doing it. It stands out. It’s different.
Look for disconfirmation. As I was thinking about doing the bookstore, I asked a lot of people why I shouldn’t do it. Not that I was looking to be talked out of it. I was asking so I could hear the concerns, the objections, the risks I hadn't considered. Every one of them raised something I hadn’t thought of and then was then able to address before opening.
Take some risk off the table. Most big, cool, intimidating things in life comes with a certain amount of risk. But just because you take a big risk doesn’t mean there aren’t ways to take risk off the table. A great piece of advice I got from Allison Hill, who owns Vroman’s and Book Soup in Los Angeles, was to make the bookstore a multipurpose space. The Painted Porch is of course not just a bookstore—it’s my office, my employees' office, the place where we record podcasts and film YouTube videos. So if nobody comes in and buys books, we're not necessarily losing money. Multi-use allows you to do more than you ordinarily would—across the board.
Think of it as an experiment. When I was kicking around the idea, Tim Ferriss told me to think of it as an experiment. Try it for two years, he said, and if you hate it at the end or it’s failing, then walk away. This piece of advice was so freeing. It gave me an out—which allowed me to bravely dive in. Because I wasn't betting my whole life on something, just a contained time commitment. Thinking of every venture, every project as an experiment is a great way to go through life. It lowers the stakes. It minimizes the downside. It lets you take a shot on something that otherwise might be way too intimidating.
Don’t trust conventional wisdom. One of the things I did while I was kicking around the idea is I looked up how expensive it is to start a bookstore. Search results said it was hundreds and hundreds of thousands of dollars—way more expensive than I was interested in. But then I wanted to question whether that number was real. So then I went and looked up how expensive it was to start an ecommerce business—something like Daily Stoic. Search results said it was hundreds of thousands of dollars more than I’d spent to start Daily Stoic. That was really helpful—to learn, oh, these people don’t really know what they’re talking about. Or that there’s a cheaper way, a different way to do it. You don’t have to do it the way that everyone else does it.
Be okay with mediocrity at first. A problem with having really high standards or when you expect a lot of yourself is that it can be hard to start something new. It’s hard to be comfortable with something that’s kind of crappy or mediocre or not all the way there. But there’s a reason most tech start ups think in terms of a minimum viable product. There’s a great Hemingway line—we actually have a shirt with it, and I have a print of it on my wall—it’s one of my all-time favorite quotes: the first draft of everything is shit. I love how The Painted Porch is now, but it took years to get it to where it is. It’s been a continual process of improvement and growth and making changes.
Doing interesting things usually pays off. When I was starting out as a writer, an author gave me a piece of advice I’ve never forgotten: If you want to be a great writer, go live an interesting life. He was right. Great art is fueled by great experiences—or, if not “great” experiences, at least interesting ones. That was in the back of my mind with the bookstore. Even if it failed, I knew the experience of trying to open a small business in rural Texas during a pandemic would be filled with stories. And it has been. I’ve drawn on it constantly—in my writing, my talks, in conversations with people on the podcast. So when you have the choice between the safe, boring path and the interesting one, take the interesting one. It always pays off.
Have a unique proposition. Most bookstores carry thousands of titles. The best one in Austin, BookPeople, stocks over 100,000. We carry about 1,000. It was one of the best decisions we made. We only carry books we love. Not only did this make it cheaper and easier to run the bookstore, it makes us stand out. If people want a specific book, they go to a certain trillion-dollar e-commerce behemoth. If people want to discover new books and have a unique experience, they come to us. We are the only bookstore in the world with our selection.
Create spectacles. Before we opened the store, I was in Bucharest, Romania for a talk. My host took me into a local bookstore that had an enormous globe hanging from the ceiling. I watched as customer after customer came in to take pictures beneath it, before checking out with books. This inspired our now infamous book tower, which I designed to be built on top of an old, broken fireplace. It’s 20 feet tall and made of some 2,000 books, 4,000 nails, and 40 gallons of glue. It was not cheap. It was not easy. But it’s probably one of the single best marketing decisions we made. Invariably, almost every customer that comes in takes a picture of it—plenty more come in because they heard about it and wanted to see it.
The positive externalities are the best part. I’ve gotten a lot out of the bookstore. I’ve learned a lot…about business, about books, about what I’m capable of. Sales have been strong. But the most rewarding part has been what it’s done for other people. Putting books we love out in the world. Creating a gathering place for the people in our community. Building something that makes our small town a little better, a little richer, a little more interesting than it was before.
Beware of mission creep. Our original plan was that we’d have only a couple hundred books, only my absolute favorite books. But I'm always reading and discovering new favorites. So the temptation to add and add and add is always there. In the military, they call this mission creep—a gradual broadening of objectives as a mission progresses. If you are setting out on a project, it’s something to be aware of.
For everything you add, take something away. There’s a great story of Mark Parker who, just after he became CEO of Nike, called Steve Jobs for advice. Is there anything Nike should do differently? Parker asked. “Just one thing,” Jobs said. “Nike makes some of the best products in the world. Products that you lust after. But you also make a lot of crap. Just get rid of the crappy stuff and focus on the good stuff.” “He was absolutely right,” Parker said. “We had to edit.” Because we’ve always done it this way, is not a good reason. Or in our case, because we’ve always carried this book, is not a good reason. We have to edit.
Have the discipline to not scale. At least once a week, someone asks if we're going to open a second location. And at least three struggling bookstores have reached out about us acquiring them. The answer is a polite no. "Do Not Go Past The Mark You Aimed For" is one of the most important laws in The 48 Laws of Power. Know when you’ve won. Know what enough is. Know your limits.
Behind mountains are more mountains. That’s a Haitian proverb I love. My wife suggested opening the bookstore in the fall of 2019. Then COVID delayed us a year. Then we didn't feel right opening for another year. Then a freak storm and some political incompetence shut down the power grid—burst pipes, busted roof. Then a global supply chain crisis made books hard to get. There’s the day-to-day stuff too: employees get sick, the internet goes out, shipments arrive damaged, a toilet leaks, the door won’t shut properly all of a sudden. But that’s how it goes. With most things in life, you don’t overcome one obstacle, you don’t get through the first, second, or third year of your business, and then suddenly you're magically done with obstacles. No, it’s one damn thing after another. Expect it. Work through it. Keep going.
Learn from the cats. When we were thinking about opening a bookstore, I bought a course from a bookstore consultant. I talked to friends. I talked to bookstore owners while on a book tour. I got a lot of advice, gathered best practices, and learned what worked for others. And yet, the single most popular thing about The Painted Porch is something that never came up…the cats. In 2021, we took a family road trip to Cerro Gordo, the ghost town Brent Underwood has been restoring—my kids are obsessed with his YouTube videos—and came home with two cats who have lived at the bookstore ever since. They’re literally the most popular thing about the store. As one Yelp reviewer put it: “Nice collection of books, clean, very comfy atmosphere, but I’m not going to lie to the great people of Bastrop…I come for the cats.” Lol. So yes, do your research. Yes, learn from others. But keep in mind, some of the best parts of any project are things you can’t possibly predetermine.
Don’t overlook simple solutions. There’s a tendency—especially when you care a lot about something—to overthink it. To assume everything has to be big, polished, expensive, professional. But great ideas can be cheap and easy too. One of my favorite bookstores in the world, Gertrude & Alice in Bondi Beach, puts sticky notes inside their books. Just little handwritten notes from employees about why they liked this or that book. No fancy plaques. No expensive signage. We started doing it at The Painted Porch too. It’s fun, it’s human, and customers love it.
Do things only you can do. Something that’s happened with Daily Stoic over the years is as it has grown, so has the number of copycats. And so we're constantly asking, what can only we do? With the bookstore, we're lucky to have authors constantly passing through to record the podcast. While they're here, they sign books. Sometimes we do live events with them. Those books, those experiences—you can't get them anywhere else. With AI tools making it easier and easier to copy and replicate and reproduce, it’s more important than ever to find and focus on the things only you can do.
Zoom out. When we were doing a small construction project at the bookstore recently, we moved an old antique bar and found some paint on the wall, covered in plaster. Carefully scraping it away, we found a date: January 16, 1922. What was happening in the world that day? Who were the people who stood there and supervised it being painted? What kind of business was in this space a hundred years ago? How many others have come and gone since? It was a humbling reminder: we're not the first people to try something in this building, and we won't be the last. Every project, every place, every person is part of something much bigger—something that started long before us and will continue long after.
If you’re successful, your people should be successful. Nothing feels better than distributing profits or raises to the team. If you don’t take pleasure in that, you're doing it wrong, prioritizing the wrong things.
If you’ve always wanted to do it…do it. This has happened to me more than once. When my wife and I moved to a farm, I couldn't believe how many people said, “I’ve always wanted to do that.” Same with opening the bookstore. People hear you have a small-town bookstore and they light up—“I’ve always wanted to do that.” Casey Neistat has a great line: “The right time is right now.” If you’ve always wanted to do something, do it. Stop romanticizing it. Stop overthinking it. Try it. Do it small. Do it your way. But do it.
There are many ways to measure success. One of the first things people want to know is how the bookstore is doing, whether it’s a success. I like to joke, my wife and I are still together, so yes, that’s a big win. We survived. We kept ourselves together despite it all.
The real answer is that early on, we asked ourselves, what does success look like? And we decided that success was going to be: becoming more community minded, becoming more responsible, becoming better organized, having more fun, making a positive contribution.
With any project or endeavor, there are many ways to measure success. Has it made you a better person? Has it made your community better? Did it challenge you in ways you needed to be challenged? What metrics actually matter to you? Remembering why you did something—and how you defined success at the start—helps you calibrate your decisions along the way.
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