Here’s how it felt in the weeks before I resigned from my last startup: I couldn’t sleep. I couldn’t eat. Resting pulse at 120. I had reached a point..
Here’s how it felt in the weeks before I resigned from my last startup: I couldn’t sleep. I couldn’t eat. Resting pulse at 120. I had reached a point where I couldn’t agree with my co-founder over the future of the company. I had to step away from the startup for which I shed blood, sweat and tears. I didn’t want to do it, but I reached a point, physically and mentally, where I couldn’t handle the stress anymore.
This is the first public post in which I’ve ever talked about it, but through advising hundreds of startups, I’ve learned that my story is not uncommon.
Every co-founder situation is different, but one common problem that keeps popping up revolves around how the founders engage in conflict: either not enough, or far too much.
Founder drama happens even in situations where you wouldn’t expect it to crop up. Success will cover up many sins. When things are going up and to the right, things might be going wrong underneath and you won’t be aware of it. It’s the black ice of startups. It’s dangerous because every startup will hit the skids sooner or later. You can’t count on good times forever — winter is coming.
Posterous, the startup I co-founded in 2008, grew 10X yearly and became a top 200 Quantcast website in that time. But by the end of 2010, growth had flatlined. When things were going well, we were too busy keeping the site online to have anything to disagree about.
I learned the hard way that if you haven’t prepared for conflict in your co-founder relationship, you’ll be at each other’s throats right at the moment when you most need to be working well together.
The mistake that my co-founder and I made was in avoiding the dynamics of our co-founder marriage altogether. We rarely spoke directly and honestly with one another. We didn’t stop to reflect on what he needed or I needed. We never sought professional support to ensure the health of our partnership. When the honeymoon ended, there was no healthy foundation to support the company.
During my time as a partner at Y Combinator, we always looked closely at how well co-founders knew each other before they started. Most people think of good co-founding pairs in purely functional terms: a business person paired with a technical person. This is deeper than that, because when conflict does arise (and it always does), if you have nothing in common other than the startup, you’ll struggle to find common ground at the worst of times. It’s necessary for founders to have something in common, but not sufficient in and of itself.
In my case, I had known my co-founder for more than eight years, and we had been friends since college. We had history, but we learned history is not enough — you’ve got to maintain it like any relationship. It isn’t enough that you’ve been friends for years. It matters what your relationship is like now.
With hindsight, I now realize my rift with my co-founder was entirely preventable. We stopped spending time together because we were avoiding conflict. I wanted so much for us to succeed, and I wanted so much for us to be great co-founders (and to maintain the narrative that we were close and had a good partnership) that I skipped the hard work that it takes to get that relationship and do our best work: embracing conflict and resolving it. It’s a problem that I’ve recognized over and over again in founders with whom I’ve worked both as an advisor and investor.
