I've worked in environments like this both with amazing owners and with truly horrifying owners.
There's a particular type of person who runs these businesses and that person is extremely common. They cannot delegate and micromanage everything so once they get beyond their ability to manage every facet of operations themselves, their leadership ability breaks down and a bunch of people end up leaving and the cycle repeats. They very often have temper/anger management issues as well.
From that point i always ask questions about the employee count across the years, the projection and average retention.
We will need to grow a bit in the next couple years, but mostly in (I'm guessing) testing and support.
Before this I was in some other small orgs with generally good management, but they failed. We had lean years at this firm -- there was a furlough period, with 4-day workweeks and 80% salary, and I thought about leaving but honestly also enjoyed the extra day off, too.
We made it over that hump, and are now doing well. My main concerns at this point are leadership succession at the top, and also at the top of the actual dev group. The latter is more easily addressed than the former.
