I just left a gig like this after two years, and honestly, it was mostly good for me. It was tough at first, especially coming from being an founder myself. I had to adjust to having less control and not being on the same level as my friend, which caused some tension. But eventually, I got that it's different being an employee than a founder, and I made peace with that.

Looking back, being friends first and chatting as fellow founders probably made it harder to get on the same page. 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.

We don't talk as much now, and I'm not sure how he sees me, but I'm glad I did it. I definitely learned a lot about myself.

That said, I'm not keen on jumping back into something like this anytime soon.

If I do however, I would definitely go in with more tempered expectations of what I'm there to for, and what I want out of it.

As stupid and as obvious as it sounds, a lot of things can be taken for granted due to the prior relationship, 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 help a friend, though that's usually how the conversation starts.

This is something I've struggled with personally in the past, and this experience has helped me get better at that.