Founder Insecurities and My Martyr Complex

Like most people, I’ve always had an incredible ability to be insecure about all the wrong things.

In my mid-twenties, the most prominent among these was my identity as a startup founder, a role I fell into more or less by accident. I had never been the kind of kid who set up lemonade stands or arbitraged my lunch by trading with the other third graders: I was sensitive and weird, and thought of myself as an artist all throughout my childhood and teenage years. Whatever “business” even was, I knew it wasn’t for me.

I stumbled into startups when Andrew Yang came to campus my senior year to recruit for Venture for America, his then-new entrepreneurship program—a talk I saw only because a friend dragged me to it. At VFA Training Camp that summer, I was the only person in the room who didn’t raise their hand when Andrew asked which of us thought they might start a company someday. I became a startup founder two years later, at 24, mostly because my best friends were going to start a company together with or without me, and I knew I’d have major FOMO if I turned them down. And I ended up CEO a few months later only because neither of them wanted the role.

Looking back now, of course, my insecurities about fitting the mold of a startup founder seem preposterous. I was a young white guy from a good school who’d always had an interest in technology: only my love of art and (I’d like to think) above-average social skills prevented me from being a full-on tech stereotype. But at the time it didn’t feel that way. I’ve never felt myself a full member of any group I’ve been a part of. In high school I was a theater kid who knew that most theater kids are super annoying (and that Rent sucks); in college I was a writer who prided myself on being more practical than most.

Being a startup founder is—I am not breaking new ground here—very hard. When you’re young and doing it for the first time, you inevitably get most things wrong; what separates the founders who make it from the ones who don’t is how quickly your error rate decreases over time. In a culture that valorizes pouring everything you’ve got and then some into your company, you could always be doing more. But it’s hard to be doing “more” when you’re not even sure what you should be doing in the first place. I would have gladly worked sixteen-hour days in our company’s first year, if I’d only been able to come up with sixteen hours of stuff to do that would have actually driven us forward.

Since I didn’t know how to prove to myself that I belonged where I was, I turned to the only method I could come up with: treating my personal suffering as a proxy. The rest of my life becoming less and less put together must have meant that I was throwing more and more of myself into the company, and therefore that no one—least of all me—could question my commitment or whether I was cut out for this. And so I partied too much and foreclosed any real connection with the people I was dating and just generally revelled in everything around me being a bit of a mess.

During those first few years my cofounders and I were living what is now, in retrospect, a crazy life: we’d moved into this abandoned mansion in Detroit that we were still in the middle of rehabbing, sleeping on mattresses on the ground and trying not to get sawdust all over everything we owned. We’d set up the entire first floor as an office, where we spent our days desperately trying to figure out what “starting a company” actually meant. Oh, and we were also being followed by a documentary film crew one week a month.

A lot of this was fun, but I was stressed and anxious all the time; there was both a euphoria and a terror in feeling like my life was moving so fast that the whole thing threatened to go off the rails at any moment. I would look around and think to myself, this must be what really living is all about. And whenever I felt like an imposter as a founder, I’d use the corresponding messiness of my personal life as proof that I was giving the company my all.

Of course, none of this made any logical sense, and none of it made us more successful. A stable relationship almost certainly would have been a support system that helped me be a better founder; at the very least, it’s hard to do good work when you were out till 4 a.m. doing drugs with strangers the night before. But that’s the thing: I wasn’t optimizing for actually making my company successful. I was optimizing for assuaging my own insecurities.

Although the specifics vary from person to person, I’ve seen a lot of other young founders get caught up in this same mental trap. We’re all worried we’re not good enough, worried we’re secretly frauds, and grasping at any shred of “proof” that we’re not, no matter how illogical. Looking back now it’s obvious that I was committed to what I was building beyond all reason, and that no one but me ever doubted it. But, like that old story about the fish who doesn’t know what water is, I couldn’t see it at the time.

Which is not to say I regret any of this, necessarily: I like being able to look backwards at my “wild youth,” even though I know that’s mostly just a story I tell myself, and even though at least half of that wildness didn’t feel so good when I was actually in the middle of it.

Still, If I’m ever a founder again, I’ll make it a priority to put my mental health first, knowing that I’m doing so not just for my own well-being, but for the company’s. And I’ll try not to get so caught up in my own narratives—or at the very least, when doing so is inevitable, I’ll try to make up healthier narratives to get caught up in.

Yours in suspecting that for half the people who read this the only takeaway will be that I know Andrew Yang,


Read of the week: This Atlantic article about the near-elimination of Down syndrome in Denmark, through prenatal testing and voluntary abortion, raises some impossible questions about parenting, choice, and how we think about disability.