4 Years Of Lessons From Running My Own Bookstore

It was a crazy idea from the start. 

My wife and I were sitting at a cafe in Bastrop, TX and we spotted an empty storefront, a building that’s part of the National Register of Historic Places.

“You know what would be amazing there?” my wife said. “A bookstore.”

We started construction the first week of March 2020. 

But 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. 

Four years in, one of the first things people want to know is how our bookstore The Painted Porch is doing, whether it’s a success. I’d say so. I’ve certainly learned a lot along the way, both about business and life, as well as publishing and people and myself. 

Here are some of those lessons: 

Counterprogramming is key. So yeah, 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. 

Have more than one way to win. This was a great piece of advice I got from Allison Hill, who owns Vroman’s and Book Soup in Los Angeles: most bookstores only survive if they’re multipurpose spaces. The Painted Porch isn’t 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.  At the same time, it probably also wouldn’t have made sense to build out this level of podcast studio or even a writing office by itself either. So multi-use allows you to do more than you ordinarily would—across the board.

Resist the pressure to scale. At least once a week, someone asks us 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. 

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—both personally and professionally. We only carry books we love. Not only did this make it cheaper and easier to run the bookstore, it makes us stand out. It gives people a reason to come in. 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. Again, counterprogramming. 

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. For me, one of the key pieces of the puzzle was figuring out what kind of marquee feature we could add that would make coming to the store an experience. I recalled a particularly cool floor to ceiling tower of books about Abraham Lincoln in the museum attached to Ford’s Theater in DC. 

This inspired our now infamous book tower, which I designed to be built on top of an old, broken fireplace in the building. It’s 20 feet tall and made of some 2,000 books, 4,000 nails, and 40 gallons of glue.

It was not cheap to do. It was not easy to do. 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. 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.

Pass it on and pay it forward. I’m proud of the books I’ve championed over the years—of paying forward what inspired me, like the Gregory Hays translation of Meditations (I loved it so much I even put out my own edition). I love looking around The Painted Porch and seeing books you don’t often see in other stores. Just last year, the publisher of Ann Roe’s Pontius Pilate told us they had to do another printing because we’d raved about it too much. Whether you’re a writer, a bookstore owner, a coach, an entrepreneur, a teacher, a parent—when you find something that helps you, inspires you, or moves you…pass it on. Tell people about it. Help others find what helped you.. 

Reading will never get old. One of the things that gets me excited about my job is just how much stuff there is that gets me excited…that until recently I didn’t even know existed. I’ve been doing this a long time—reading seriously since high school, obsessed with Greek and Roman history for most of that time. And somehow, I only just discovered Augustus by John Williams? A book that feels like it was written for me—Memoirs of Hadrian is one of my all-time favorites—and I didn’t even know this existed? And it’s not like it’s some obscure old thing—it won the National Book Award! Then just last month I discovered The Last of the Wine, an incredible historical novel that reminded me of everything I loved about Pressfield’s Gates of Fire and Tides of War. That’s what I love about reading: the more you read the more you realize there is much more to read. Even if you have read a lot, there is not just an endless list of great authors and books still to get to, but new ones come out every day! Maybe that’s how you know you’ve found your thing: when there seems to be no end in sight, and that never stops exciting you.

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.

It’s one damn thing after another. My wife suggested opening the bookstore back 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, it’s one damn thing after another. Expect it. Work through it. Keep going.

It’s easy to focus on what’s going wrong. In any business or project, it’s easy to fixate on what’s going wrong. As I mentioned, the little daily problems don’t seem to stop. Those things demand your attention, of course. But I’ve found it helpful—even necessary—to make an effort to notice and appreciate the things that are going well, the things that are working, the little wins we get every day.

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.

Be deliberate with your space. In the book Strip Tees by Kate Flannery (a great guest when she came on the Daily Stoic Podcast—listen to the episode here), there’s a story about Dov Charney walking through an American Apparel store. He stopped, pointed to the tile beneath his feet, and said, “Do you know how much rent I pay for this tile every day? Do you know how many T-shirts we have to sell just to cover the cost of this one tile?” I didn’t witness this one—but I saw many performances like that—and now that I own my own shop, the point stuck with me: every inch of space you control is costing you something. Are you using it well? Is it serving the purpose you think it is? In a bookstore—or any business—it pays to be deliberate about what goes where. What are you putting in your most valuable real estate?

Does it make you better or worse? In the middle of the project, when the whole thing seemed impossible and doomed to fail—as we tried to open a bookstore, raise two kids when schools were closed, and make sense of the world—I wrote a note to myself: “2020 is a test: will it make you a better person or a worse person?” That was the test that I reminded myself of over and over again: will this make you a better person or a worse person? If starting a business makes you a worse person—if it stresses you out, if it tears your relationships apart, if it makes you bitter or frustrated with people—then it doesn’t matter how much money it makes or external praise it receives. It’s not successful.

A sense of urgency matters. A couple of weeks ago, a shipment of books came in on a Friday afternoon. I heard someone on the staff say, “We’ll unpack those tomorrow.” I’m glad I heard it because I had to stop them and explain that, unless the books in those boxes were opened and the orders waiting on them were fulfilled (in time for the morning mail pickup on Saturday), they would not even begin traveling in the customer’s direction until Monday afternoon. So what seemed like a little delay until the next morning was really like a 72-hour delay. Every small delay or shortcut has second-, third-, and fourth-order consequences. That’s why it’s important—whether you’re packing boxes, replying to emails, or making big strategic calls—to think a step or two ahead. Don’t procrastinate. Do it now. Do it with urgency.

Ask why it’s being done that way. One day I noticed our team was packing shipments in a pretty inefficient way. I asked why. The answer? That’s how so-and-so showed me when I started. No one had questioned it since. This happens all the time—in businesses, on teams, in life. People inherit a process, follow it out of habit, and never stop to ask: Is this the best way? Does this still make sense? The most useful question in any system is often the simplest: Why are we doing it like this?

Know the history of your space. I was talking to Jeni Britton Bauer—the founder of Jeni’s Ice Cream—and she told me the first ice cream shops date back to the late 1600s or early 1700s. Her point was that what feels trendy or modern is often something old coming back around. That applies to bookstores, too. Or really any craft or creative business. What you’re doing might feel new or niche, but it probably has deeper roots than you think.

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.

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, for example, 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. This has always been good advice, but with these 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 and a kind of sign: 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. It can be very easy on a project to get caught up in the immediacy of what’s in front of you, to get caught up in the day-to-day of running a business or chasing a goal. But every project, every place, every person is part of something much bigger—something that started long before us and will continue long after.

There’s always problems you aren’t even aware of. What started as a small construction project at the bookstore recently led to uncovering another issue, which led us to another thing that needed fixing…and that led to something else entirely. We’re lucky we tackled the initial project. One thing that keeps you up at night is all the things you don’t know are happening. The controversial Samuel Zemurray’s line—per Rich Cohen’s amazing book The Fish That Ate the Whale—was “Never trust the report.” He went to South America or Boston or wherever the business was being done and saw the situation up close for himself. He wanted first hand knowledge so as a leader he could make the right decisions. 

I will leave you with one final bonus piece of advice: hard things are good for you. It is only from doing hard things, as the Stoics said, that we learn what we’re capable of. Seneca would say that he actually pitied people who have never experienced challenges. “You have passed through life without an opponent,” he said. “No one can ever know what you are capable of, not even you.”

Opening a bookstore during a global pandemic has been the hardest thing I’ve ever done. It’s been challenging. Expensive. At times overwhelming. There were setbacks we didn’t anticipate, problems we didn’t know existed, and moments where it would’ve been easier to walk away.

Which is what’s made it one of the most interesting, meaningful, and rewarding experiences of my life. We’ve learned so much—about business, about books, about what we are capable of. We’ve built something that matters to our community and to us. And in the end, those are the things that stay with you—not the easy wins, not the shortcuts, not the stuff or the money.

So if you’re thinking of doing something difficult, if you feel called to do something big…do it. Regardless of whether it succeeds or fails, you’ll be better for it. No one will wonder what you were capable of. Not even you.