I once worked with a guy who had been with an 8 year old startup for around 7 years. The company had stopped growing at around the 200 million dollar run rate and he’d stopped really trying to do much other than get by. Someone once directly asked why he stayed and it turned out he had a million+ options. He was never bad, never good, and never took risks or did anything that would make him stick out.
6 years later the startup is still private and hasn’t grown (it’s probably smaller today than it was then). When I think back on the experience there were a number of people who felt strangely trapped into working there and didn’t give a crap.
I worked at one other company doing the options game and saw the same thing - anecdotally I never saw this at companies giving RSUs. As a manager, it would be tough to part ways with someone if you know your stripping them of a million dollars in equity.
I wonder if this is why mid-life startups that stop growing start to feel "stale". Too many people who just want their money and to get out of dodge.