I just left a gig like this after two and half years (a leadership role at a 1-10 stage startup), and I have to say it was a overall a net positive experience for me.<p>NGL it took time to get used to it. Being an ex-founder, it was doubly difficult as not only did I have less agency than I was used to (and frankly expected), I was also no longer on an equal footing to my friend. This led to some friction and disagreements of how things should be done, but at the end of the day, it came down to perspective differences as a founder and as an employee, and I learned to make with peace with the fact it was his company, and not mine.<p>In retrospect, I think the fact that we were friends first, and had spoken a lot as fellow founders beforehand, made it harder to align expectations in this dynamic. Thankfully, we parted on good terms, and I'm still helping them out as a consultant, which feels like a nice middle ground for me.<p>That said, I'm not looking to jump back into something like this anytime soon.<p>If I do however, I would definitely go into any future engagement with more tempered expectations of what I'm there to for, and what I want out of it.<p>As obvious as it sounds, a lot of things can be taken for granted due to the prior relationship (on both sides), and its important to lay out as much of your thoughts and expectations upfront, so that there is as little ambiguity and misunderstandings down the line. No detail is too trivial, especially around compensation, and its important to recognize and remember that you're there to do a job, not just helping out a friend, which is how the conversation usually starts.<p>This whole thing has taught me a lot about handling that balance, and a lot more about myself as well.