It’s easy to take unlikely risks when you already have a “never need to work again” windfall.
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).
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).