How To Know if Your Cofounder Will Quit on You
A completely personal, highly unscientific test to predict if you or someone you know is right for the startup life.
I’m excited to be speaking at FailCon in October, a conference of startup founders sharing their failures. As a founder, I have thought (and talked and written) a lot about what it means to fail and how to deal with it when it happens. And yet, reflecting on my own experience, I find myself skeptical of the very idea that early-stage startups “fail.”
In the earliest stages, (the only ones I’m experienced in), startups are not made up of founders—they are the founders. They are living organisms sustained by passion and trust and sheer force of will. As long as you are willing to let go of one idea for a better one, to abandon a code base and start over from scratch, to keep pitching investors who keep telling you no, you’re still a startup (or at least a startup founder).
What really puts a stop to a startup is when one (or all) of the founders decides the payoff for being successful will never be worth the sacrifices it takes to get there.
Why I Quit My Startup
Let me take you back to January of this year. Our team (including my now-fiancé and FailCon co-presenter, Jackson) had been working full-time on our startup for 9 months. We had taken in a small round from my parents and another founder’s dad. My responsibility as CEO was to use that money to fly to SF and come back when I’d found investors.
Before we even started pitching, we ran the numbers during a call and confirmed my nagging suspicion that almost all our money was already spoken for. We couldn’t start paying ourselves, as we’d hoped. For the first time, we considered taking part-time jobs to relieve some financial stress and give ourselves time to gain the traction that had eluded us.
When I hung up, I thought about jobs I might take. Ideas rushed in. I started researching companies and sending emails and writing lists. A few hours later I looked up from what I was doing and thought, “This is more excited and motivated than I’ve felt for six months.” Some part of me knew that was the beginning of the end.
In the weeks that followed—some of the hardest I can remember—I decided to step down as CEO. My parents were angry, not so much about losing money but from feeling that I’d somehow duped them. That I had convinced them I really believed in this thing and would try my best to make it succeed—and then I just gave up.
Jackson and Peter, our technical cofounder and the only one left from our once 6-strong team, felt abandoned and betrayed. I didn’t blame them. For a brief time, Jackson took over as CEO and the two of them pivoted to a new product. But the momentum had been lost.
For a while I told myself that it was the startup—the idea—that had failed. The market was too small. We waited too long to test our prototype. We languished too long on the line between “get big fast” and “organic growth.” We never should have left SF for Chicago.
But eventually, in no small part because Jackson called me out on it, I accepted that what really happened was simpler than that: I quit. I made a conscious decision to stop making the sacrifices necessary to move forward. Why? I finally confronted the fact that, even if our startup succeeded, it would never provide me a life I wanted.
Through many, many conversations, I’ve come to see Jackson and myself as opposite ends of a “right for startup life” spectrum—I’m on the “not” end and he’s down at “very.” From this I’ve developed my own understanding of what separates those two poles. I hope that by sharing our differences I can help you see more clearly where you (or a cofounder) fit on the spectrum.
You Might Be A Startup Founder If…
You want to make the world a better place. You believe that “a better place” is a tangible, achievable goal, and that it is humanity’s responsibility to strive toward this. You dream of creating tools that help make this a reality.
You will judge your life at its end by how many people’s lives you have improved. You are not particularly interested in changes made on a small scale. Therefore you are drawn to politics—or technology—or other global systems that impact everyone everywhere. If this sounds like you, then startups present an incredible opportunity.
Let’s Take a Second to Clarify ‘Startups’
By “startups” I do not mean “tech-focused companies” or “scrappy online businesses.” Startups strive to alter our world and the way we experience it. As Eric Reis explains, companies are designed to make money; startups are designed to test hypotheses and grow, grow, grow. For this reason they are funded almost exclusively by a specific type of investor (the venture capitalist) who understands this opportunity and is willing to gamble on the rare successes.
To be attractive to VCs, a startup must be particularly focused on growth. Big growth. Ten-times growth in five years or less. Growth that is more important than “profit,” and often thought to be stifled by it. Growth that will sometimes outweigh the wishes of users. Growth that demands a stream of small white lies (mostly to yourself) about what you and your idea and your team are likely to actually achieve. Growth that favors bravado and credit-taking and delusions of grandeur—that favors, to be frank, hypomanic young men. (Not that there’s anything wrong with that…I’m planning to marry one of them.)
If you believe your startup stands even a sliver of a chance of making the world a “better place,” these hardly feel like sacrifices at all.
You Might Not Be a Startup Founder If…
On the other hand, let’s say you find it hard to buy into the idea of “making the world a better place” on a grand scale. (Maybe, like me, you would go so far as to say that humanity is but a hangnail on the outstretched arms of time and that its backslides have been as numerous as its “advances.” Maybe not.)
If you are more interested in having a direct, tangible impact on a small group of people; if you crave being able to see the small ways your actions improve lives; if you find transparency and authenticity and immediate look-me-in-the-eyes validation necessary to stay motivated, then being a founder of the kinds of startups I’ve described is a hard road to go. When the goal of “startups” is out of line with your own goals, those same sacrifices suddenly loom very large.
Don’t Listen To This Girl—She’s a Quitter
In a popular post I published on the Women 2.0 blog last year, I insisted that being a startup CEO provided me the freedom to define for myself what it meant to be a startup CEO. And I was right. Had I stayed a startup CEO, I am confident I would have stayed committed to transparency and “feeling your feelings” and all the other things I set out to embody despite the cultural pushback. But to truly change the system in my own small way, I would have had to stay a startup CEO. Instead, the deeper I dragged myself into startup culture, the less I wanted to stick my neck out to change it.
I got worn down by the showboating and the constant pitching and the expectation of single-minded workaholism. I worried I was part of a system prompting people to spend more time with their devices instead of being with the people beside them. I found myself slightly obsessed with making money (not my usual style)—not just for the sense of security it would provide but as a clear validation that what I was doing was valuable. I was unhealthy and unhappy and failing my team because of it.
I am grateful to and have great respect for those who are still influencing startup culture from the inside, but I decided my time would be better spent in a culture I didn’t need to change to feel welcome in. I now work full-time for a women-led marketing agency and support Jackson as he supports the startup community. And I still consider myself an entrepreneur, with plans to some day start a “microbusiness” (something I myself confused with a startup at first).
But being the founder of a Silicon Valley startup is simply not part of my plans. I’ve scratched it off my list. I understand myself (and Jackson) better because of the experience, so I will never think of it as a “failure.” But when people ask why our startup failed, I now don’t hesitate to tell them, “It didn’t—I quit.”