His payoff from paypal is not something most people will have access to. The dot com boom was basically a lottery.
Compaq managed to sell AltaVista for $2.3 billion 6 months later and not long before the crash so maybe it wasn't the stupidest move on their side.
Elon family riches is uncertain: https://futurism.com/elon-musk-dad-emerald-mine
Compaq managed to sell AltaVista for $2.3 billion 6 months later and not long before the crash so maybe it wasn't the stupidest move on their side.