I’ve been around the block a few times in tech startups, two separate startups the founders were friends before I joined as an employee. In both cases I met and

I’ve been around the block a few times in tech startups, two separate startups the founders were friends before I joined as an employee. In both cases I met and became friends with them at previous startups where we were all employees in different departments. If you set boundaries and accept that you will see a different version of your friend as soon as the pressure of vcs and boards employees and management and pride and direct communication and so on take hold then you’ll be ok. This is especially true for first time founders who do not realize how unprepared they really were for the realities of being a founder. Having been a founder myself before I joined I maybe had greater empathy for the way they became completely different people under those pressures and the dynamics of your friendships can change in different settings. My advice is to expect and make space for that, and leave on good terms when you start to see that their emergent coping mechanisms with those pressures start to affect your friendship with them and the way you see them. Treat the friendship as paramount, don’t do it if you don’t have financial security to prevent money or layoffs from feeling personal, don’t make yourself a bus factor, let them have a learning experience and be ok with them not taking your advice.