Most of the time, the person isn't even a millionaire or billionaire when the company starts/grows -- but even at the very early stages, there is something different and slightly batshit about them.
And speaking from personal experience as someone who has also worked at high-profile startups (some very early stage), that's kind of part of the appeal. An audacious leader can be charismatic and compelling. And then once you're "in it" you start to normalize the increasingly batshit stuff you see, writing it off as "that's just X being X" -- which can often be unhealthy because with no accountability, things can go from "eccentric/audacious but ultimately helpful" to "this is insanity and is harming more than it is helping."
Two problems tend to arise from it:
1. Ex ante, people who don't understand it think that just by being weird, they will have exceptional (weirdly good) results. So they are libertine or uncivil and that alone doesn't drive anything useful.
2. Ex post, people who achieved highly attribute the success to the weirdness, and take it as extra license to let the id flow free.
In fact, my belief is that a good bit of weirdness both causes and is the effect of some other qualities that in turn correlate with success: obsessive knowledge of a domain, obsessive levels of effort, single-mindedness, manic level charisma, inordinate confidence (itself charismatic), and willingness to be contrarian / unorthodox.
But man is it annoying when people are just assholes and wave it off blithely as coming with the territory.