Why I (try to) run a small business on the side

By day, I work for Basecamp, analyzing data to improve the product and business. By night, I f̶i̶g̶h̶t̶ ̶c̶r̶i̶m̶e̶ make and sell wooden topographic maps.

My small business is never going to make me a millionaire. It’s not going to make me famous. It’s sometimes physically hard and repetitive. It can be discouraging. It doesn’t really return a meaningful profit.

So why do I bother with this?

It’s not for the money

Let me get one thing out of the way: I don’t do this for the money. Quite frankly, there isn’t much of it. My woodworking business will do low five figures of revenue, and while it might turn a small profit this year, it will definitely have negative cash flow. Relative to my day job salary, my business is fairly insignificant.

I’m extremely fortunate to have a day job that pays me well and provides excellent benefits, and I recognize I’m privileged to be able to run a small business without really caring about the money. I don’t take that position lightly, but I hope you’ll believe me when I say that I’m not making maps for the money.

I love maps and so do you

Part of why I make maps is because I love them, and I always have. As a kid I had maps and globes all over my room for no apparent reason. I started my professional career by analyzing health care data to produce a variety of chloropleth maps, and I love the occasions where I get to make a map for work now. I like all cool maps, and wooden topographic maps are especially cool maps.

Lots of other people love maps too, and the way people react to seeing a wooden topographic map for the first time is gratifying. It’s especially enjoyable to see how young children react — their instinct to touch, to look for things they recognize, to find patterns in the wood, etc. (that reaction from kids is why I’m giving away maps to schools).

The making of the maps is also a fun process for me. It starts with some satisfying computer work to build a 3d model, then some physical labor to prepare wood to be cut. I get to figure out how to hold the piece of wood while it’s cut, run a computer controller router, and then turn a rough cut piece into a beautiful finished map. The processes are individually enjoyable, and every couple of hours of work you get a little hit of joy from finishing a map.

I love challenges

This map business comes with challenges in two flavors.

First, there are the technical challenges. Even though I’ve been making these maps for two years and made over a thousand to date, each new geography poses a new problem to solve, and there’s a continuing search to optimize production — how can I make maps more efficiently and of higher quality?

But the real challenge is on the business side. I’ve spent the past decade analyzing businesses both large and small and making strategic recommendations, but I’ve never run a business (other than an aborted lawn care business when I was about 11 that never got beyond designing a flyer). By and large I think I’ve given good advice and made my employers plenty of money, but that’s not the same as building something from the ground up.

If you ask anyone who knows me well, they’ll probably tell you that I’m laughably bad at sales. My typical sales strategy consists of telling people all the reasons they don’t want to buy what I’m selling (and then not being surprised when they don’t buy). I’ve gotten away with this because I haven’t had to actually sell anything in my life before that’s more significant than junk on Craigslist. When you’re running a solo small business making a custom product, you have no other choice but to learn to sell. I’m still bad at sales, but I’m getting better.

Every challenge my business has faced — legal, process, marketing, fulfillment, etc. — draws on the same principals that I’ve used in my day job for years, but the context is different, and I feel like I’m really learning important business lessons.

My side business helps my real career and life

I don’t run a side business in order to build skills that help Basecamp. I like my job, but I’m not intentionally spending my nights and weekends doing this to benefit it. Despite that not being my intention, I do think that I’ve gotten better at my “real” job as a result of running my woodworking business.

Basecamp sells primarily to small businesses, and I think I have a better understanding of who we’re selling to, what they’re thinking about, and why they’re buying than I did a year ago. I no longer have to imagine what a small business owner is thinking when they’re shopping for software; I am a small business owner shopping for software.

I’ve also had the opportunity to meet and work with other small business owners (as suppliers and customers) and to learn about their business. I’ve conducted dozens of interviews with small business owners over the years, but the interaction isn’t nearly as genuine or insightful as the conversations that come up when you’re two small businesses working together.

There have been a lot of points in the past year that have been difficult or frustrating — the parts that will be the funny overcoming of adversity in the Hallmark movie about my company in twenty years. Working through those has made me more patient and empathetic than I think I was a year ago.


I hope to be running this small side business for years to come. It’s been a challenging but rewarding experience, and I’m the better for it, even if my wallet isn’t any fatter.