I would tend to favor your father's position; I'm a libertarian. I put in the context of some are our industries brightest and best have had some remarkable ideas and luck but how many times did it take them to get there? Like an old Ted Turner story about his smart quotes and the remarks of just how many bad ones it took to get there.
the issue with this in society is the ability of people to have enough bad outcomes to arrive at the good one. can we level that playing field or do we first need to find out why so many don't have the drive to try? Do we discourage people too early in life, do we give some the excuse they need to not try?
Your ability to handle the consequences of either making bad choices or being unlucky is dependent in large measure on factors like financial resilience (can you afford to take a risky project without running the chance of being homeless?) and social support (will your partner be prepared to support a change of direction, do your parents recognise the value of trying and failing at difficult things, will your country help you retrain if things go wrong?). These things are not evenly distributed.
I'm now in some senses on my third career (I'm 35). Each of those decisions to change direction, take risks and grow as a person were made a lot easier because I had a good enough salary to put money aside to cover the risks, and a wife who happens to be both adventure-loving and locationally-flexible. Not to mention that the most recent career change (moving into academic research) basically required a self-funded MSc as a preparatory to funded PhD study (I was moving into quite a different field, and there's basically no funding for taught Masters courses in the UK). That's more than half the people who could benefit from it priced out from the start.
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.
the issue with this in society is the ability of people to have enough bad outcomes to arrive at the good one. can we level that playing field or do we first need to find out why so many don't have the drive to try? Do we discourage people too early in life, do we give some the excuse they need to not try?