I think there are people who take big unlikely risks. Statistically some of them succeed. Now they are big risk takers with survivorship bias and illusions of self importance, AND lots power/money. And that can be scary.
I can’t risk my retirement nest egg.
If Peter Thiel ended PayPal with $55 million that means he could set aside ~$5-10 to live the rest of his life and risk the rest.
So really I would argue that having a risk-adjacent personality isn’t related to skill. Thiel was willing to throw half a million dollars at random tech startups done by college dropouts and he also had a social network of his own thanks to doing the same with PayPal.
So it’s about networking, capital, and timing more than skill.
Thiel would be a nobody if he was born 10 years later. Where is the PayPal-like opportunity in today’s tech landscape? The modern startup is wildly capital heavy and loses money for possibly decades (e.g., Lyft just made its first profit EVER in 2024).
What he's had is an army of internet bots pumping up his supposed credentials (visible even in the voting patterns here on YN)
In every instance, a lot of other people did all the work. Musk provided funds, which a machine could do.
And, he did fail. A lot. But the more money you have, the more you can fail.