Well, he's not taking risks anymore by doing this. He has already proven himself, he's rich, and he's paid incredible amounts to do whatever he likes.
I wonder if, societally, it's true though, or if statistically the more reliable way to "succeed" in life, is getting good at selling and defending ideas, even the bad ones.
It hard to spot, while/when you are doing it.
I think what you're talking about here "stand up for what you believe in" is maybe a position you should take with others.
While "kill your darlings" is a devil's advocate position you should take with yourself when you don't have someone giving you constructive criticism.