I co-founder-dated 7 people. Cut things off with 5. Broke up with 1. Now, run a company with the last.
Here’s the process I used to find the one—after getting it wrong a few times.
Most advice says: only start a company with someone you’ve worked with before.
But I’m a counterexample.
My experience:
- My 1st cofounder was a close friend. We worked together before we knew what we wanted to build but realized we had fundamentally different goals and interests. We “broke up” (but remain friends)!
- My 2nd cofounder was a total stranger, but it worked out.
Here’s what I did to make it work that 2nd time:
- Crystallize 70-80% of your idea Don’t date if you have 0 idea what you want to build. With my first cofounder, we jumped in before knowing what we wanted to build. We wasted months trying to force-fit an idea into the tiny overlap of our interests. The second time, I flipped the process: I got clear on the problem space first—then looked for someone already interested in that space. From there, we shaped the idea together.
- Create serendipity I told everyone I was looking for a cofounder. I went to events, joined forums, DMed people, caught up with friends — and created my own serendipity to chance upon the one. The right person came from a random industry meetup.
- Deal with the hard questions upfront Answer the 50 important questions to get aligned on. It’s also a fun set of questions that also help you be clear about what YOU care about in your journey Hard questions should be dealt with upfront. If my 1st cofounder and I did this, we maybe could’ve discovered our incompatibility sooner.
- Run a 1-2 week mini project Treat it like a trial run. You’ll quickly see how you build, communicate, and make decisions together. Debrief after. Be brutally honest to save yourselves the time and pain in the long run I’ve discontinued working with people because we realized that the way we communicated with each other didn’t match, and that’s ok! Better to have learned this earlier than later.
- “Cautiously optimistic” exploration My now cofounder and I kept exploring other cofounders while validating ideas together. We went deeper in collaboration but also transparently kept our options open.
- Make it “exclusive” but vibe check constantly At a point we decided to make it exclusive. There’s no dramatic moment—vibes just becomes clear. Each phase before this one derisks the relationship. But, treat it like any relationship that requires ongoing work and alignment. We, for example, have regular check-ins to make sure we’re still on the same page.
TAKEAWAY:
Cofounder dating is much like romantic dating.. maybe harder! But the right cofounder is a multiplier on everything: speed, clarity, resilience, joy. So treat the search with the same intention you’d bring to any high-stakes relationship.
Hope this helps someone who’s in the messy middle of finding a cofounder. The one is out there.