The answer might be that he’s actually far less successful than he claims.
That’s the reason why he won’t let anyone see his tax returns.
He shutdown his court case against the BBC rather than open the books to the lawyers.
This is a bloke that failed at running casinos. A business where suckers just hand you their money. And he failed.
He just “ain’t right good” at business but has the ego of The Big Lebowski.