I've had mostly good experiences doing this across two startups. The biggest challenge I've seen is the awkwardness around people who have previously been peers now being stacked in a hierarchy. The best way I've found to get around this is to think about your career as a long road where roles can change e.g. "You're working for me now, but next time I may be working for you". I had a former manager and friend work f…
For example, when you moved from being a peer to a position lower in the hierarchy, did this alter the nature of your friendship? And similarly, what changes occurred when the roles were reversed?