In my experience, the serial startup execs mostly don't live in the city. In the 90s, I knew several who also had an apartment near the office, but that's much less common now that the sort of place they'd want is going for $8K/mo.
People are leaving sv and housing prices are the reason. It's going to lead to brain drain. Why bother with that congested hell hole when you can live anywhere else and cut your cost of living by 50 percent. Your average founder is 30 and they are not into partying. Sv is for 20 year olds
I wouldn't believe that a CEO of a company that has raised $40 million is leaving because his wife needs a roommate to make rent. His wife should probably live with him if she needs to save money.
Fwiw, housing prices (rents) have barely budged in much of the Bay Area for the past 4 years. If the exodus hasn't already happened, I doubt it will.