That's just it, though; for people like the ones in SV, it doesn't run out. There's always a golden parachute, always a politician willing to give a bailout, always enough money to just stop working for good.
When you reach that level, you have to work incredibly hard to screw things up.
I think you've not experienced one of the real downturns. There isn't always a golden parachute for most of the people involved.