Welcome to all the new subscribers who found me through my appearance in Substack’s recent “Desire” roundup! I have no idea what you’re expecting, but I hope this is it.
Almost as soon as I started a company, I started imagining what it’d be like if it failed.
It was impossible not to, with statistics left and right about the 90% of new businesses that don’t make it and stories of failed startups everywhere around us. If we were going to go down this road, I believed, we had to steel ourselves for the possibility—the likelihood, really—of failure.
But failure was also the easiest outcome to imagine. Success was fluid and ineffable: I barely understood what it meant to be the 24-year-old founder of a startup so new it wasn’t really a company at all, just three best friends stumbling around in the dark—and I actually was that person. Imagining myself as the CEO of a big, successful company felt like imagining myself at 200 years old. Failure, though—failure wasn’t hard to picture at all. I’d shut everything down, go back to my old life, become a regular person again. Not that I had ever really been a regular person.
By the time our failure actually approached—four years, four million dollars, and twenty hires later—imagining it had become even easier. As we geared up for a fundraising round we weren’t sure we could pull off, we knew there was a real possibility this was finally the end. Like anticipating a breakup, I found myself repeatedly picturing the moment where I’d tell our team, running through the exact words I’d use in my head over and over until it started to feel like I was revisiting a memory, like we’d failed already. I didn’t want to fail, but there was still a perverse comfort in the fantasy. As Epictetus said, “What is death? A scary mask. Take it off—see, it doesn’t bite.”
The day we decided to shut down, I took a red-eye from San Francisco to Michigan to deliver the news firsthand to our team in Detroit. I sat in our office, on the couch that we’d taken out of my first apartment, and I heard the same words I’d gone over so many times in my head tumble out of my mouth. For a second I wondered if my habitual visualizations of this moment hadn’t somehow manifested our failure into reality. “I’ve imagined this so many times,” I told the team. “But that isn’t making this any less hard.” And I realized I had imagined saying that exact phrase too. Eventually I made it to the end of my little speech, or just ran out of things to say. Our team enveloped me in a giant and highly unprofessional group hug. And then, at last, it was over.
Except, of course, that it wasn’t. Before I’d ever started a company myself, I imagined that failing was kind of like dying in a video game—you get eaten by the flower or you fall off the ledge and then bam!, that’s it, game over. But in reality, shutting down your company is never something that just happens to you—it’s always, in the end, your choice. Because no matter how dire things are, there’s always a Plan B or C or D. You can always find a way to keep going.
Our Plan B was actually better than a lot of other companies’ Plan A’s. We had an offer on the table for a million-dollar bridge round—not quite the money we wanted to raise, but enough to get us through at least the next six months. But we had reluctantly concluded that taking it would have left us no closer to success than we’d been before, only having burned through another half year of our lives and another million dollars of other people’s money.
But although I was as certain as I could be that shutting down was the right decision, the fact that it was a decision in the first place made it near-impossible to avoid dwelling on the what-ifs, and I desperately craved the certainty of failure as I’d previously imagined it. When I told my cofounders I thought it was time to throw in the towel, a part of me was devastated that they agreed.
We had lost faith. And losing faith in your company is like a balloon popping: it can happen in an instant and it’s impossible to undo. If, moments after we’d decided it was over, the best VC in the world had offered to lead a giant Series A for us, I don’t think we would have been capable of saying yes. Failure had been easy to picture, but deciding to fail had been unimaginable. And then, as soon as it became real, it was the prospect of continuing on that became impossible.
The other way that your company failing isn’t like dying in a video game is that it takes a lot of work and a lot of time. In our case even more than usual: unlike, say, a social media app, a property management company (or at least, an ethical one) can’t just shut down overnight. We needed to give our customers time to transition to a new provider, and we needed to make sure our tenants knew where to send rent and who to call if a pipe burst. On top of that, despite having been warned dozens of times by dozens of people to be absolutely sure this didn’t happen, we ended up without enough money to pay off all our debts. That’s a long story for another post, but let me just say this: if you’re a founder, you do not want to make that same mistake. Bankruptcy and the corporate veil can protect your assets, but they won’t do shit for your emotions.
Running your company when it’s already failed is just like running your company under normal circumstances, except everything is a hundred times shittier. You have all the usual stress of being a founder, plus all the added stress of having to shut things down. The company has already failed, so nothing you’re doing really matters, but if you screw any of it up there might be serious consequences. Everyone is mad at you, except for all the people who aren’t mad at you, and they make you feel even worse. On the roughest days I fantasized about our investors calling and yelling at me for losing all their money. But actually almost all of our investors were incredibly supportive. The nice ones made me feel the most guilty—I’d rather have just been yelled at. Sometimes kindness is the hardest reaction to accept.
Mixed in, though, is a deep sense of relief: you finally know how the story ends. Building a startup is a constant exercise in wondering if you’ll make it and trying desperately to avoid the 10,000 ways you might not. It sucks to fail, but at least you don’t have to wonder anymore. Once you’re already dead, you’re invincible.
Banksy said, in a quote he stole from someone else, that you die twice: once when you stop breathing, and again when somebody says your name for the last time. Your startup dies twice too: first when you decide it’s over, and again when you actually stop working on it. For the first few months after we decided to shut down, I was still a startup founder, still working on my company every day. In a weird way, my routine and identity hadn’t actually changed that much.
But eventually, of course, it did. And then I had to decide what to do next. For years I’d spent almost all of my working hours doing not what I most liked doing, but rather whatever I thought the company and the team needed from me. (I’ve written before about the paradox of liking my job despite often not liking most of the individual activities it required from me day to day.)
At first, thinking about what I actually wanted was like working a muscle I hadn’t used in a long time. It turned out to be a harder question to answer than I’d thought. Mostly the answer was that I wanted to do nothing, and so that’s more or less what I did for the next year.
Now the company is a distant memory and the person I was when I ran it is a stranger. Sometimes the whole thing feels like just a phase I went through, no different from my childhood obsession with Legos. I’m pretty sure I’ll start another company someday, even though I’m also pretty sure I’m much happier now than I was then. In a lot of ways 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.
I’m not a fan of the over-valorization of failure, of the idea that my startup wasn’t “really” a failure because it impacted so many people so positively along the way. We didn’t work so hard and make so many sacrifices just for some personal growth and a few amazing stories. But although I have an infinite list of things I’d do differently, all in all, I have no regrets.
Before we started the company, my cofounders and I asked each other: “If we do this for the next chunk of our lives and it doesn’t work out, will it still have been worth it in the end?” We decided it would be, and I haven’t changed my mind since. But I’m not really sure that whether or not something was “worth it” is a question that can actually be answered. This was a thing I did for a while, and then it was over. Maybe there isn’t any more to it than that.
Yours in acknowledging that every time I self-deprecatingly joke about having lost a bunch of investors’ money, it’s also a humblebrag that people trusted me with millions of dollars in the first place,