How to Choose a CoFounder
Darrell Silver, CoFounder and CEO at Thinkful
Dan and I founded Thinkful in 2012, six months after our first meeting and after two months of daily discussion of whether we could work together for a decade. Seven years later, we sold the company for $100M, and are still together helping adults get better careers as part of Chegg. I’d love to tell you there’s a silver bullet to finding a cofounder, but there isn’t. Instead, there’s luck, luck, luck, and a few best practices I’ve learned. Thanks to Tribeca Venture Partners for being one of our early investors and allowing me to share a few of them.
Communication
Dan and I have a rare and easy ability to understand what the other is trying to achieve and then help them or push them to achieve it. At a startup, the easy times between cofounders are the strategic decisions and big moves in the face of imminent demise. For us, the hard discussions always happened when our roles were in question because one of us was stumbling or losing motivation. Our ability to trust one another and be honest about our strengths and weaknesses led to the reinvention of our roles and responsibilities every year or two. If you think there’s no hope, the first thing that disappears is communication. Our ability to always respect each other and talk through challenges saved us many times.
Complementary Career Interests
Look for a cofounder with complementary interests. The skills you need will change at every stage, but your interests are more durable, especially if they’re supported by your cofounder. When your cofounder has complementary interests to your own, they’ll come to push you to develop them. If you have the same interests, then look out: you’ll find yourself competing with that person for opportunities, and that’s a disaster. If you don’t know your interests (including listing “make our company a success” — which is a cop-out), then you may not be ready for a cofounder. As your interests evolve, you’ll need to communicate with your cofounder to remain highly effective in your job and relationship.
Process Over Roles
Nothing about your relationship will remain stable through this journey. What matters is that you have a process that allows and encourages this change rather than clings to what you once needed. For Dan and me, we keep monthly meetings after hours to discuss our relationship. We adopted the best practices from The Partnership Charter into a living document that serves as our agenda. Often these meetings seemed unnecessary, but sometimes they led to key debates about what we wanted in our lives, in our hearts, for the team, our investors, and for each other. It also led us, in mid-2018, to set out on the course that led to our successful exit in October 2019.
Finding a cofounder is both luck and process, I hope these insights will help you to move one step closer.
