There's "rich", and there's "enough money to rot your brain". I can believe Trump started with the latter, but the other two were less than that. IIRC GWB was "just" a multimillionaire even when he became president, about the same as Musk when Zip2 got sold.

The only reason we hear about Musk is because the gamble on PayPal gave him enough to then roll the dice again on a few more things, of which SpaceX and Tesla kinda actually worked.

Though with Tesla, their lifetime profits being ~= lifetime government subsidies to them and their consumers, by "worked" I mean "you can buy them and drive them" rather than it being a genuine business opportunity.

While this is a dick move, when the question is "is he smart?", it's still a positive result.