Building a Company with a Friend

I've built with friends more times than I should have. And honestly, it's been a bad idea more often than not.

The Room was with my high school friend. We've known each other forever. That's supposed to be a good thing, right?

The Problem

When things get hard — and they always get hard — you can't just have a professional conversation. Everything is loaded with history. Every disagreement feels personal.

You end up protecting the friendship more than you protect the company. Or worse, you protect neither.

What I Learned

Building a company stress-tests relationships in ways nothing else does. The stakes are real. The pressure is constant. Small annoyances become big resentments.

I'm not saying never do it. But think twice. Make sure you can have hard conversations. Make sure the friendship can survive failure.

Because statistically, the company will fail. Can the friendship survive that?