They learn and with some time they can become excellent - or simply just good enough - at running a business.
The 'ballsy' ones are disproportionally represented in the stellar successes camp as well as the miserable failure camp, with the majority of them in the latter.
If you are not risk averse at all you will have to be extremely lucky to survive an extended stretch of entrepreneurship. For every phase of managing a company there is a different profile that works best, and the best entrepreneurs are the ones that adapt their personalities to the situation they find themselves in.
Serial gamblers can have a winning streak, but they eventually always lose.