Yahoo Finance Lessons from a startup founder at the crossroads of failure
Somewhere I heard that a startup doesn’t fail when it fails. It fails when the founders give up.
In this “money is no longer free” market, that begs two questions: When should founders give up? And how should those founders manage their psychology while seeking the answers to such a momentous question?
I am facing this exact dilemma right now. My new consumer software startup has not gone particularly well by one sort of important measure: growth. It’s been a four-year grind to find some signal of product-market fit—and we haven’t found it yet. At one point, we had 12 people. Soon, it might just be my cofounder Jen Greenwood and me, at least until we rebuild in a more methodical way.
It’s been like panning for gold in a turbulent river: Sometimes the prize feels closer, other times farther away. Still other times it feels like we are drowning in aimlessness and exasperation. An identity crisis looms for any high achiever flirting with failure, and a calculation begins on the conflicting forces of sunk costs and lost time on the one hand, and reputational harm on the other. As entrepreneurs, we struggle to separate our egos from the prospects of our startups. We conflate the fate of the enterprise with our value as human beings.
Our startup has burned through $10 million of cash, much of it our own. Were it not for the privilege of access to capital that comes from my being an “exited” founder, we’d have been dead in the water years ago. As Marc Andreessen warned me during a Zoom meeting in 2020 (which did not lead to an investment): “Make sure you don’t raise too much money—or you’ll be stuck working on this for a long time. Raise just enough to get to the milestones that justify the next raise.”
Oops.
As an entrepreneur who loves fundraising, I kept Jedi-mind-tricking myself into believing I’d achieved the milestones to raise more. Over last year’s holiday, Jen and I took stock of where we were. Years of iteration. An exhausted team. And yet: still $2 million left in the bank.
Should we try to sell or merge with another startup or company? Should we return capital to our investors, at 16 cents on the dollar? Or should we keep iterating, perhaps consider yet another pivot, even if it means we might run out of cash and end up with goose eggs for our investors, our team, and our time?
According to Ken Chenault, the legendary former CEO of American Express and current chairman of venture firm General Catalyst, the job of a leader is to deliver on two sometimes conflicting mandates: creating hope, and defining reality.
The reason we call the entrepreneurial journey a roller coaster is because—as with so much of the human experience—hope can be a peak and reality can be the pits. My observation is that it is nearly impossible to be hopeful and realistic at the same time.
To fulfill Chenault’s mandate, some days I publicly project hope, usually when I am genuinely feeling optimistic. Other days I privately suffer the reality of things going nowhere, and then attempt to share just the right amount of the difficulty with the team. At my best, I offer enough of a dose of disinfecting sunlight to build trust through transparency, but not so much that doubt and demoralization run rampant. I don’t want to lead those I’m leading to update their LinkedIn profiles.
My roller coaster is amplified by an underlying mood disorder called bipolar I. (I’ve shared my journey with the condition in a memoir and a subsequent TED Talk.) For the first nine years I spent building my previous startup, Bonobos, I was in denial that I had a mental illness. I assumed if people knew about my college diagnosis, I’d never be able to recruit a team or raise capital.
As entrepreneurs, we struggle to separate our egos from the prospects of our startups. We conflate the fate of the enterprise with our value as human beings.
In reality, there are droves of entrepreneurs with challenges like mine. According to a study from the University of California at San Francisco, neurodiversity correlates with entrepreneurial drive. Bipolar disorder might affect 2% of the adult population, but 11% of entrepreneurs. Five times higher. That type of disproportionate representation is also seen for entrepreneurial leaders with depression, ADHD, generalized anxiety disorder, and substance-use disorder.
In some strange way, I process this fact as luck. The wake-up call I received when a manic episode landed me at Bellevue Hospital for a week, and then in jail for a day, catalyzed life changes that provide mental scaffolding I didn’t have before. The foundations of my regimen look like this:
* Two sessions with my psychiatrist every week.
* Medication every day (in lieu of self-medication with alcohol).
* Eight hours of sleep a night, with a verifying screenshot from my Whoop app sent every morning to my wife, doctor, mother, and sister.
Building a company is a mentally unhealthy endeavor. It attracts folks with mental health issues, perhaps exacerbating them, and it may create mental health issues for others.
Still, each of us, neurodivergent or not, has mental fitness to maintain. And while everyone is different, everyone needs a regimen. Whether that regimen entails meditation, medication, exercise, therapy, executive coaching, eating keto, morning sunlight, cold plunges, or just listening to Andrew Huberman podcasts on repeat, do it.
If we don’t secure our own oxygen masks, we’re not going to be able to secure anyone else’s either.
The financial health of a company and the mental health of its founder often track together.
For our last round of fundraising, in the back half of 2022, venture capital was beginning to evaporate. In some ways, I deserved to be stymied. I hadn’t proved that I could find a product that worked.
To stay alive, I sought out a high-net-worth entrepreneur to lead a down round that enabled us to keep operating. I used to think down rounds spelled the end. But with the support of seasoned insiders like venture capitalists Kirsten Green and Jeremy Liew, who realized they’d rather own some of their stake for something rather than 100% of it for nothing, and with a rebooted equity pool for the team, a down round could be a new beginning. Sure enough, both Green and Liew invested more.
Flat is the new up. And down is the new flat.
The entrepreneur who led that round is precisely who I called this past December to get advice.
Ev williams, cofounder of Twitter and the founding CEO of Medium and Blogger, picked up the phone. I laid out my hopes and fears for him about where we were. He asked all the right, skeptical questions—about our metrics, our team’s morale, and where I was. And at the end of the call he delivered a judgment that was more upbeat than I expected:
“I wouldn’t stop right now. Keep going.”
Keep going.
Those words rang in my ears the rest of winter break. Jen and I made some tough decisions in the ensuing days. We planned to take the team down to the studs and rebuild from there. Some good people would be going part-time, or leaving. At least three months of severance helped dull the blow—something we could do because we assessed the crisis that was coming before it became an actual crisis. We reduced burn by two-thirds, deciding to focus on go-to-market rather than deepening our technical investments.
With this renewed focus, we actually started growing at over 10% a week. We moved the headquarters of the company. And we went all-in on one key product move, and on one key market: sweet home Chicago.
Things are picking up. Or are they? More aptly put: How long will it be before the roller coaster tops out and begins a new plunge?
Hope springs eternal in the world of startups. Because it has to.
As we embarked on 2024, I resolved to microdose reality every day, rather than wallowing in the troughs, to make it possible to metabolize the hard stuff and stay more buoyant, more stoically and resiliently optimistic, every day.
Past need not be prologue.
The truth is that we sometimes have a moral obligation to keep going—to our teams, to our customers, and to our shareholders. It’s not always about what’s best for us in the moment. The memories of having been through difficult times at Bonobos, and having endured, provide ballast. The lasting culture we built, the solid financial outcome, the fact that the brand has doubled in size since we sold it—it’s all a reminder that it can be worth it.
It calls to mind something that kept me going during darker days at Bonobos, when catatonic depression had me sometimes feeling like I didn’t want to live. It was a book one of our first employees, Kevin Kelleher, gave me called Cowboy Ethics. One page had a photo of a cowboy on horseback, getting pummeled by freezing rain.
The caption reads: When you’re riding through hell, keep riding.
Of course in pop culture, cowboys are stoic loners who push their bodies and minds to the limit. They’re not typically paragons of vulnerability. But in real life, we entrepreneurial cowboys and cowgirls need to take care of body and mind, and ask for help when we need it. We also need to hold ourselves accountable for our own mental health, and make sure we don’t cause harm to others. Stick to that mentality, and you’ll have the fuel you need, whichever way your company goes.
And if you can, and if you should …
Keep going.
Andy Dunn is the founding CEO of Bonobos and Pie and the author of Burn Rate: Launching a Startup and Losing My Mind.
This article appears in the February/March 2024 issue of Fortune with the headline, “Face to face with failure.”
This story was originally featured on Fortune.com
