Slouching Towards Entrepreneurship

How I fell ass-backwards into startups

I ended up in the startup world almost completely by accident.

As a kid, I was about as non-entrepreneurial as you could be. I was artsy and a bit of a space cadet, and I saw “business”—whatever that even was—as the exclusive province of the boring. It didn’t help that almost no one in my family had a career outside of medicine, law, and teaching. True, as a self-employed lawyer, my father technically owned his own business, but I’ve never heard him describe himself as a small business owner. He’ll probably read this and get into some debate with me about whether a sole proprietorship even counts as a business at all.

Whether my parents intended it or not, I grew up under the impression that there was something inherently unseemly about doing anything too explicitly businesslike. When my friend Alex visited Japan in fourth grade and returned with a plan for the two of us to resell Japanese Pokémon cards to our classmates, my father convinced me that we’d be taking advantage of our friends with the markup we planned to add. Though I doubt I put up much of a fight: I hadn’t cared about the money at all, I just thought it would have been a fun thing to do.

I did get into tech at a young age, but every technical skill I picked up was driven by a creative urge. I taught myself HTML in fifth grade because I wanted to put my short stories online and it was either learn to code or slum it with GeoCities. I learned Final Cut in middle school because I wanted to adorn my dumb little home videos with special effects beyond what iMovie could do. I learned Photoshop, Illustrator, and InDesign because they were the natural next step after I’d mastered Kid Pix. But I never associated any of these technologies with business, and I don’t think I even knew what a startup was. I remember being impressed by then-new tools like Flickr and YouTube, but it never occurred to me that there were companies behind them. If I thought about their origins at all, I imagined them as the products of individual creators, maybe not too different from myself.

And so all throughout my childhood and teen years and even well into college, I assumed I would end up as some kind of artist. The running joke in my family was that my academically superior and more hardworking younger sister would end up supporting me financially for my entire life.

I took my first steps into the startup world because of two people: my friend Josh, and Andrew Yang.

Before he was a UBI activist, Presidential candidate, and constant meme, Andrew was a former tech executive no one had ever heard of launching a nonprofit called Venture for America, who planned to send recent grads to work at startups in quote-unquote “emerging” cities like Detroit. Andrew came to Wesleyan my senior year to recruit for VFA, and made his pitch in a dingy room in the student center to what couldn’t have been more than ten people. It wasn’t a talk I had planned on attending: I had no interest in moving to Detroit, and I definitely didn’t have any interest in working for a startup. But Josh was going—he had bailed on our plans to hang out to attend Andrew’s session instead—and since I had nothing better to do at the time, I tagged along.

I don’t remember that first pitch at all, so I can only assume that I was swayed by some combination of Andrew’s charisma and the infectious energy Josh had then for almost everything, good and bad alike. I applied to VFA on a whim but didn’t think I’d actually do the program until the final round of the process later that year, an all-day group interview in New York, where I was so blown away by the other candidates that I left determined to do whatever it was they were doing, whether becoming garbagemen or medical test subjects. Though I didn’t know it at the time, that day was the beginning of a long series of career choices made mostly based on the people I’d be working with.

Even then, though, I thought of VFA and startups as a short-term detour. At their Training Camp that summer, Andrew asked that whole first cohort of 40 recent grads who among us thought we might start a company someday, and I was the only person who didn’t raise my hand.

I’ve told the story of how I ended up starting a company anyway before, so I won’t go through the whole thing again. The short version is that it was a series of small steps, none of which I thought of as leading me towards entrepreneurship at the time: I bought an abandoned mansion with some friends, got deep in the real estate world, and ended up starting a company with them based on the issues we’d run into as small-time landlords.

Actually, though, it’d be more accurate to say they ended up starting a company with me. They were the ones who took the initiative, and when they asked me to join them, I dallied for a long time before saying yes. I wish I could say that there was some grand moment when I finally saw myself as an entrepreneur, but in reality only two things happened. First, I realized that I would have unbearable FOMO if my two best friends started a company without me, especially when we were all living in the same house. And second, I came back from a music festival in Las Vegas soaked in the kind of warm afterglow that leads one to make impulsive life decisions. A day or two after watching Kanye rant from the top of a neon Ferris wheel, I finally told them I was in.

Even then, it was a long time until I became comfortable thinking of myself as a “real” startup founder, and even longer until I felt I’d grown into a real CEO, the role I’d eventually taken on because no one else wanted it. But there were many ways in which the cozy glare of hindsight made it seem like entrepreneurship had been the obvious path for me all along. I’d always liked charting my own path, rallying teams, feeling like I was competing in the big leagues. And I found I actually enjoyed having my creative output pulled out of me by the demands of the market, instead of having to come up with it all on my own. There’s no such thing as “founder’s block” because your customers are always telling you exactly what they want you to build next.

Of course, that company fell apart in the end. And although my current job is highly entrepreneurial, I’m not a founder anymore—for now, at least. In fact, sometimes I’m not even really sure whether I still work in tech at all. On Deck is very much a tech startup, but my day-to-day mostly involves working with writers. I like having one foot in each world. Although entrepreneurship is a way of life for me now, I still have mixed feelings about being “in tech,” whatever that even means anymore. I started a tech company because that’s what ambitious entrepreneurs do these days. If I’d been born four hundred years prior, I would have made ships; two thousand years prior to that, and I probably would have started a religion.

There are still times when I wonder what might have been if I’d decided to just go for it and write novels, or musicals. Maybe I still will, someday. The older I get the more I feel like every door I walk through leaves a hundred others slamming shut forever in my wake.

And the sister my parents joked would have to support me forever? Turns out she became an academic and I got a high-paying tech job. Who’s gonna be stuck supporting who now?

Yours in having made myself super nostalgic through Kid Pix by writing this,