It is likely that he didn't lose his last contact with the reality faced by the commoners until after he built the foundation for that wealth.
At a certain point, personal wealth becomes largely self-perpetuating, without further conscious efforts, and ultra-rich people can also acquire a bubble of intermediaries that insulate them from the commoners and their ordinary problems. They can always afford the durable goods or services that solve those problems effortlessly. And the people around them may simply pre-emptively order those solutions on their behalf before the problem actually manifests.
The skills you need to earn your living expenses when you already have $50G are very different from those you need when you have $50.
At a certain point, personal wealth becomes largely self-perpetuating, without further conscious efforts, and ultra-rich people can also acquire a bubble of intermediaries that insulate them from the commoners and their ordinary problems. They can always afford the durable goods or services that solve those problems effortlessly. And the people around them may simply pre-emptively order those solutions on their behalf before the problem actually manifests.
The skills you need to earn your living expenses when you already have $50G are very different from those you need when you have $50.