Such people have transcended the usual entrepreneur "take risks with other people's money" success story and reached "take risks because even if I lose every bet, I'm still unimaginably rich". Musk theoretically lost $30 billion buying and mismanaging Twitter, and it doesn't matter: he got control of a major social-media network, and if it no longer produces revenue, who cares?

I would like to ensure that you are aware of an Elon Musk anecdote that strongly supports your point here: "Elon Musk and the Infinite Rebuy"

[Max] Levchin was at a friend’s bachelor pad hanging out with Musk. Some people were playing a high-stakes game of Texas Hold ‘Em. Although Musk was not a card player, he pulled up to the table. “There were all these nerds and sharpsters who were good at memorizing cards and calculating odds,” Levchin says. “Elon just proceeded to go all in on every hand and lose. Then he would buy more chips and double down. Eventually, after losing many hands, he went all in and won. Then he said “Right, fine, I’m done.”