The chance of getting in early enough to a $2B company that exits comfortably has to be under 1%. Maybe under 0.5%. CB Insights has an article from a few years ago saying 1.28%.
Taking out companies below $2B, companies that didnt pan out so well (Magic Leap, Zenefits, WeWork), and you doing the right things to take advantage of your equity, I’m guessing that number drops to 0.35% or 0.25% or 1 in 300-400 startups.
Might as well not consider such an unlikely scenario. Plus if things don’t pan out at a startup and you’re just looking for money. You quite possibly made less during those years.