> At a bare minimum, he has created several incredibly successful businesses in his lifetime, so he must be doing something right.

No, this is a common fallacy.

The main reason to get crazy rich and successful is statistics: be lucky. I.e., accidentally do the successful things. And usually starting rich helps, so you have the opportunities.

Crazy success is not a measure for capability. There is no correlation. Yes, it is sad, so despite this, the fallacy is a great motivation for many.