2 Years Of Lessons From Running My Own Bookstore

It is only from doing hard things, the Stoics said, that we learn what we’re capable of.

A little over three years ago, my wife and I had the craziest idea we’ve ever had in our lives: to open a bookstore in Bastrop, Texas.

Opening a small business is always hard. But opening a small business during a pandemic in a small town in rural Texas? To call it a challenge would be an understatement.

We’ve learned a lot…about business, about books, and about what we’re capable of. Last year, I wrote a piece on the lessons we’d learned in our first year of business at The Painted Porch. Now, another year has passed and we have learned a few more…and re-learned some of the ones we thought we’d gotten the first time. I share them here so you can perhaps learn a little from my experiences and hopefully go create something cool of your own out of it.

[1] Anything can be a good business if you treat it like a business. Too many indie bookstores are started because people think they’ll be fun…or because they love books. No, you have to be serious. I learned this as a writer: treat it like a job.

[2] The bookstore of course is not just a bookstore. It is my office. It is my employee’s office. It is where I record podcasts and film YouTube videos. I rent part of the building to another business (a really cool record store called Astro Records). When you are thinking about taking a big risk, look for little ways to take some risk off the table. Find multiple uses, multiple options so that if one fails, you can still succeed.

[3] On the Daily Stoic podcast, Matthew McConaughey gave me a better framework for making big decisions. He told me he’s known in Hollywood as a Quick No, Long Yes. His No’s are quick. But before he says Yes to something, “I give myself about 2 weeks in each frame of mind—Yes I’m in, No I’m out—and then I measure what keeps me up at night.”

[4] Keep your eye on the prize. What is success to you? What metrics actually matter to you? Remembering why you did something and how you measure success helps you calibrate your decisions properly. I’m happy enough to be putting books out in the world, making this community better, having a physical space, challenging myself, etc…as long as I don’t lose lots of money, that’s a win.

[5] Forget the politics. It’s been interesting to watch people in our small town care a lot about what other people in the small town think. Except this small town isn’t big enough to support a bookstore. When you’re starting out doing things, you get strong opinions from people in your local scene etc. But that’s not who you should be trying to impress, or who matters in the long run. Look outward, onwards. Don’t be stuck thinking small, don’t let the scene you chanced into constrain you.

[6] Don’t be afraid to be political though. We delayed opening during the worst days of COVID. We kept up safety protocols even after the state of Texas washed its hands of its responsibilities last year. We did it even though people got mad at us for it, even though it probably cost us business. My conscience is clean and that’s what counts. Keeping your community and your staff safe is good for business in the long run anyway.

[7] Beware of mission creep. Our original plan was that we’d have only a couple hundred books, only my absolute favorite books, only the books I put in my Reading List Email. It would only be those books. But the problem is, I’m always reading and discovering new favorite books. So the temptation to add and add and add is always there. In the military, they call this mission creep. It’s hard to predict exactly how things are going to unfold, so there tends to be a gradual broadening of objectives as a mission or battle progresses. If you are setting out on a project, just something to be aware of.

[8] 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. “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 or because it sold well in the past, is not a good reason. We have to edit.

[9] Whenever I am at the store, people are excited to see me and ask a bunch of questions. Whenever my wife is there people ask her, “Where are your kids?” No one has EVER asked me that. It’s just a reminder that entrepreneurship is easier for some than others and the whole idea of just pulling yourselves up by your bootstraps is nonsense. Be aware of your advantages and privileges.

[10] Speaking of which…something that’s been hard to navigate is all the people who come to the bookstore to see me. On the one hand, it is awesome. But on the other hand, if I give everyone twenty minutes, my day is gone. This means I sometimes have to be rude…but if I am not, then I am rude to my writing, to my family, to myself.

[11] 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.

[12] A few weeks ago, an employee made a bad call and the result was an unnecessary $7,000 shipping bill. It was a tough pill for me to swallow, but I tried to think of the story about the late IBM CEO Tom Watson. In the 1960s, Watson called an executive into his office after his venture lost $10 million. The man assumed he was being fired. Watson told him, “Fired? Hell, I spent $10 million educating you. I just want to be sure you learned the right lessons.”

[13] As I said last time, I think one of the best decisions we made was making our book tower. 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. Because it’s the number one thing people come into the store to take pictures of.

[14] For similar reasons, we put a tree in the bookstore (watch the video, it’s awesome). When we were lugging the tree across Main Street, people stopped us and asked what we we’re doing. We told them, we’re putting this in the bookstore to look like it’s growing out of the ceiling. Wow, people would say, that’s incredible. I talk about this in Trust Me I’m Lying— if you want to be in the news, you have to do things that are newsworthy. If you want attention, you have to do things that capture attention.

[15] 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 weeks and months to get it to where it is. It’s been a continual process of improvement and growth and making changes.

[16] The Odyssey is roughly 2,800 years old. We sold a copy of it yesterday. Books are a great reminder of the staying power of something great (there’s a latin expression: Ars longa, vita brevis. Life is short, art is long). But then again, the translation we sold (my favorite) from Emily Wilson is fresh and new. Never underestimate the power of new packaging of something timeless and old.

[17] Every month I still send out my reading list email. We sell several hundred books in the store, but a permission asset where I recommend 5-10 each month? It’s very powerful. Cultivate these assets, and practice the art of curation. It’s a recipe for success.

[18] When we find that sales are low, one thing we do is just move stuff around in the store. I don’t know why but it seems to create a new energy, not just for the customers but also for the staff.

[19] The number one thing people say when they hear we have a bookstore is “I’ve always wanted to do that.” That’s a sad thing to say. If you want to do something, do it. I’m not saying it will be easy or even fun…but Seneca is right when he said that the one thing fools all have in common is that they are always telling themselves someday.

[20] The idea of “Fuck Yes…or No” is far too simple. Dropping out of college, I was maybe 51/49 on it. Leaving my corporate job to become a writer, maybe 60/40. Opening the bookstore, I was simply terrified. The truly life-changing decisions are usually like that. If I had only ever done things I was absolutely certain about, I’d have missed out on experiences I love. Conversely, I regret a good chunk of my “Fuck yes’s.”

[21] One thing I’ve observed about people who are successful at one thing is they transfer their high standards over to new projects. The problem is when you have really high standards, 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. Like I said about Hemingway, you have to be comfortable with crappy first drafts. The bookstore today is way better than it was the day it opened, and if it’s not better next year, then we’ll have let ourselves down.

[22] In the fall of 2019, as I was thinking about doing the bookstore, I was with James Clear, Mark Manson, Shane Parish, and Tim Urban, and they all said, definitely don’t do it—there were way better ways to make money, they said…and they were probably right. But what’s the point of success if you can’t use it to do stuff that’s cool? Turning money into more money is not the only aim in life. What is the point of being successful if all you do is reinvest that money into shit you don’t really care about?

[23] One of the dangerous things that can happen when you succeed at doing something a lot of people told you was a bad idea…is that you stop listening when people tell you your ideas are bad. You stop listening when people raise doubts. This is the worst lesson you can learn in life. The bookstore worked, but that doesn’t mean my next crazy idea will work. I have to do real work to make sure the next one isn’t actually crazy, I have to work extra hard next time. That’s the lesson to take from success.

And I actually have one more bonus piece of advice: When I asked Tim Ferriss for advice when I was kicking around the idea, he said 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 sometime, just a contained time commitment.

Well, two years have come and gone and we love it. Maybe that will change in the future, but for now we’re locked in. But 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. Even if the bookstore had failed, or even if it never makes another dollar, learning the value of that advice, that insight, has changed me for the better.

So go try a hard and challenging thing. You’ll emerge better for it…probably in more ways than one.