Did he really win? His kids all hate him, his wives all left him, he has no real friends. Anyone he interacts with is purely after money and power they can get from him. He spends all day being angry on twitter.com.
I think the point of the Rogen quote is that there's no real way to win. This is not cope by the not mega-rich and famous. It's an inevitable result of wanting universal acclaim.
Musk has more money than most of us would dream of, but the game isn't over until it's over.
Speaking just for myself, I've lost respect from Elon Musk. I admire Musk's accomplishments, especially Starship and the Falcon rockets. But I don't respect Musk's personal judgement, his moral integrity or his ethics.
He doesn't know me, and he doesn't care about my opinion (or care about ethics for that matter). But there are a lot of people like me who used to respect him and no longer do. He's surrounded himself with fawning sycophants. At some level he's got to know this, and that the people pretending to pay him respect aren't themselves worthy of respect.
Is that winning?