Well, it seems like the OP was supposed to get stock options at these places where they worked, but somehow their stakes vaporized in some kind of finance shell game. But of course, it's all caveat employtor, right? Silicon valley companies were illegally depressing wages for years, and it's all about the individual workers not "negotiating good enuf". Fuck off. Capitalism is broken because the owners are scamming the workers en masse.
Yeah if it takes too long, initial valuation may suffer and stock options vaporize. Its dangerous to stick around after a revaluation downward, with no new stock options offered.