I didn't downvote, but: there are plenty of entrepreneurial people you could bring up with regards to this, but Ted Turner went to prep school & collage in an age when most people didn't go to college. His parents were well off business owners who presumably not only set him up as a good position in life, but more importantly - and this is to your point - was a safety net so he even COULD fail over and over again.

The vast majority of the population are not put in a position to be able to fail over and over again like Ted Turner was, so since you used him as your example the answer to your question should be obvious.