Date before you marry a co-founder

My old self: Smart, motivated, and excited about the same idea. That was enough for me to hand someone co-founder equity.

My new self: That's how my first co-founder breakup happened, and I've watched other builders make the same mistake since. A co-founder relationship is a business marriage. You'll spend more time with them than with your actual spouse, and if it goes wrong, unwinding equity is brutal.

Many founders learned the same lesson the hard way. They show up with different levels of commitment, with different understandings or interpretations of what it is that they are doing.

The trick is to treat finding a co-founder like dating: try them as a contractor first, see if your visions actually line up under real deadlines, not just over coffee.

I should say the second time I tried this, it worked a little better, but it still eventually ended in another breakup. That wasn't because the contractor-first approach failed. It was because I still didn't have a clear idea of what I needed or why I wanted a co-founder in the first place.

Then when you pop the question, you got to get the prenub right away. Put in a vesting cliff, a year with nothing, then four years of earning it. It protects both of you.

The mistake is skipping the dating phase because you're excited or in a hurry, and once you've built IP together with someone on the cap table, getting them off it is a legal headache, not a conversation.