It is a side effect of the "fitness function" evaluation of humans. If a person is "successful" it is taken for granted that they are doing something right even if it is irrelevant. It isn't just wealth that benefits from this - social standing or a respected talent alone can do it.

In another way it makes sense, divergent thinking is tolerated for the very purpose of evaluating how effective new ideas are, and we ourselves tolerate being weird because we believe we can prove something new.

One decides how far to push the envelope and how much they can tolerate seeming crazy. That’s how you earn trust in your judgement.

In a way it makes sense: Someone poor who is strange is a burden on others, which someone rich who is strange isn't, since they can pay for whatever weird thing they do.