Once you have a few dozen million dollars, it's not so hard to maintain and grow that (unless you go on idiotic spending sprees) because you start getting access to the kind of investments that have much higher expected returns than the kind of investments a blue collar worker has access to.
But nerd culture values intelligence so much that we tell ourselves that of course Zuckerberg, Thiel, and others must be geniuses because a) how would they have gotten to where they are otherwise? and b) nerds like to think of themselves as geniuses as well, and therefore just one successful startup away from watching Game of Thrones with Zuck on a Sunday night.
The problem with this is that we then don't recognize when those industry leaders are acting as ignorant/stupid as any other average educated person, and instead come up with convoluted explanation about how they're contrarians and they always play the most offensive move in chess and surely that must correlate to their political choices.