It's strange to imply he is some kind of underdog when his net worth is probably around $100M. He can spend the rest of his days reflecting on whatever topic he wants, as can his children, and his great grand children, and their children. His great great great grand children may need to get a job though.
Unless you set up money in a trust, it has a tendency to disappear through the generations quickly. And even in a trust, by the 3rd or 4th generation there is often not too much to go around.
There's a saying where I'm from: "clogs to clogs in three generations". Man works himself up from clog-wearing poverty to wealth; son seems the dad's journey and values wealth; grandson grows up in wealth and doesn't understand how it happened so loses it.
