Long story short.
Good friend sees an opportunity for me to join his business. It honestly seems like a great fit for a lot of reasons.
But the conventional wisdom not to do business with friends is holding me up a bit.
Does anyone here have experience in this space? Have you stayed good friends? Have you become better friends? Enemies?
I know there’s a lot of nuance but I’m just hoping for some perspective.
Thanks all!
Opportunities with friends can work incredibly well, but only if the foundation is solid.
The biggest mistake I see—over and over—in litigation between former friends, partners, or even family members is that they relied on trust instead of documentation. Everything feels great on the front end, so no one wants to “formalize” things… until they disagree, and then the lack of clarity becomes a very expensive problem.
If you decide to move forward, I would put every expectation, responsibility, ownership interest, exit plan, and dispute-resolution process in writing. Not because you don’t trust your friend, but because clear agreements protect both the relationship and the business.
I’ve seen friendships strengthen when the business is structured well from day one—and I’ve also seen friendships implode when people skip that step. Good paperwork doesn't guarantee success, but it dramatically improves the of preserving the friendship over the course of the business.