Obsessed

My childhood was a series of obsessions.

First there was money: not as a measure of wealth or a medium of exchange, but money as art. I drew hundreds of bill of my own design, and read everything I could find about the notorious “banknote artist” (and occasional counterfeiter) JSG Boggs. Then came the Wizard of Oz: I read all fourteen books (yes, the story you know is just the first in a long line of sequels) and loved the much darker and criminally underrated follow-up film Return to Oz, in which Dorothy escapes from the mental asylum she’s been committed to after telling her family about the events of the first movie and revisits Oz only to find it a charred, post-apocalyptic ruin.

After that came Legos, the Amazon rainforest, Kid Pix (a sort of 90’s-era child’s Photoshop/MS Paint on steroids), and Pokémon. Each came with an associated creative habit that I pursued compulsively: endless invented Lego worlds, papier-mâché piranhas, pages and pages of bitmap art, made-up Pokémon cards of my own design.

And that was just elementary school.

My fixations became slightly less all-consuming as I made my way through my teen years, but the general trend continued. I bounced from one obsession to the next, a serial monogamist for my passions. When I got old enough to be interested in girls (which, for me, wasn’t that old), my crushes followed the same pattern, coming one by one in rapid-fire, overwhelming bursts. I must have fallen in love a hundred times before I turned fifteen, each time for less than an hour.

“Obsession” as a concept is generally coded as negative, but the truth is I liked being obsessed. There was something pleasurable, almost spiritual, about being so gripped by an interest that everything else disappeared. Ever since I’d been old enough to think, I’d wondered what the meaning of life was. But when you’re really obsessed, that question’s answer is obvious. The meaning of life is Angela. Or writing poetry. Or Pokémon.

So when I got older and my ability to lose myself like that started to fade, it felt like a great loss, even though I knew it was an inevitable part of growing up. Like falling in love—which I’d once been able to do with any pretty girl just by looking at her for a few minutes, but which had now become an elusive matter involving personal compatibility and some kind of inexplicable magic known as “chemistry”—finding an object for my obsession had stopped being so simple. I had learned to see the world with more nuance, and everything had gotten complicated.


When I started a startup, just a few months out from my 24th birthday, I worried constantly that I wasn’t obsessed enough.

There’s a narrative in Startup World that true founders are seized by what they’re building at the expense of everything else, that you’ll only be successful at solving a problem if it’s one you can’t ever stop thinking about. And I knew I wasn’t anywhere near that obsessed with real estate. I saw an opportunity, and I enjoyed the intricacies of starting a company, and what we were doing was interesting—but so is everything, really, if you look closely enough. I certainly couldn’t identify at all with the people I met who were truly obsessed with real estate, all of whom seemed to be, well, exactly what you’d imagine when you think of the kind of person who genuinely loves real estate.

But more importantly, I doubted I was even capable of getting that obsessed with anything anymore. I’d learned to see the world in too many shades of gray, and was skeptical skeptical of a startup culture that discourages founders from questioning themselves too much, even as I immersed myself in it. And I’d developed too many disparate interests to go back to the days when I was happy to be known only as the boy who was obsessed with Oz. It’s obnoxious, but I remember thinking even then that if I were to become a world-famous entrepreneur, on the cover of Forbes, I’d be happy for about a minute before complaining, “But I’m so much more than that! Don’t they know I once wrote a musical?”

I knew that the most extreme versions of the founder obsession story were overstated—is anyone really “obsessed” with insurance billing or enterprise password management? Still, I looked around at other entrepreneurs and saw a singlemindedness, a lack of second thoughts about the path they’d chosen, that I felt like I lacked. I remember once telling the documentary crew that was following us around (a story for another time) that if our company eventually failed, deep down, it would be because we just weren’t into it enough.

And so I faked it. Perhaps all the other founders were faking it too, and the whole thing was a hall of mirrors—I’ll probably never know for sure. I played the part of the dedicated, tunnel-vision entrepreneur, and you know what? Eventually, it worked. Forget “fake it till you make it”—it’s fake it till you become it. Wear a mask long enough, and eventually it becomes a part of your face.

By the time we’d built a real team, I’d become obsessed with our company as an entity, with our culture, with the responsibilities I had towards the people who’d tied their fates to mine. There were whole years where I thought about almost nothing else, even though I never stopped worrying that I didn’t care as much as the imaginary über-founder I’d built up in my mind. (Looking back now, of course, I see the very fact of my worry as proof of its needlessness: only those who really do care worry that they don’t.)

But in the end, all of that wasn’t enough. I now believe that to succeed as a startup founder, you have to care about the problem you’re solving more than I ever did, no matter how deep your obsession with the other aspects of company-building. After all, your team, culture, and day-to-day responsibilities will all change multiple times over the course of your company’s life. Only the mission will—if you’re lucky—stay the same. And it’s a deep obsession with the mission that can keep you going when everything else feels like it’s turning to shit.

It turned out the premonition I had at 24 was right. I could, and have, ascribed our company’s failure to all kinds of practical issues: the operational complexities of property management, the unique challenges of the Detroit market, the impossibility of building a strong brand for a product where a successful performance means your customers never have to think about you. But to have a shot at overcoming any of those obstacles, you need to care enough about the thing you’re doing. Ultimately, I just don’t think I did.


The more time that goes by, the less certain I am that I’ll ever start another company. For a while I was sure I would—even in the absolute depths of my post-failure detox, I knew I’d caught the startup bug. I’ve written before about how my mental model of entrepreneurship is similar to that of addiction: the inexplicable drive to continue engaging in a behavior despite its provably harmful consequences.

But every time I’ve dipped a toe in those waters again, I’ve found it harder and harder to imagine any kind of idea that feels worthy of being the focus of such a long chapter of my life. Even as I’ve gotten better and better at coming up with promising startup ideas, I’ve become worse and worse at envisioning myself truly obsessed with any of them. Like someone who threw himself too soon into a short-lived first marriage, I have a higher bar for the next one.

I know I can never go back to the days when a months-long obsession could be triggered by something as simple as a movie trailer. But there are still a lot of times when I wish I could to quiet the voice in my head that can see everything from a hundred different angles. I think I’d like to find my way to a new manner of being consumed by something. One that’s thoughtful and nuanced and even-keeled, yes—but also a little bit obsessive.