Trump has said he received a million dollar loan to get started (circa early 1970s?). The return he generated, to say the least, was extraordinary.

Further, even going by that bogus story, not all sectors of the economy generate the same returns. A person is not to be shamed for making less money in retail or dog food than in tech or oil. One has to consider the results they generated in the field they chose to focus in. It's disingenuous, and then some, to hold all business people up to the standard of: well if you had just put all your money, at some arbitrary high point, into an index fund for N years, you'd be richer - that would discredit nearly all successful business people.

Hey Sam Walton, if you had just liquidated all of your Walmart shares in 1992 before you died and put the wealth into an index fund, your family would be richer. That's mathematically correct and ridiculous. Off the top of my head I can list dozens of examples like this among the Forbes 400 past or present.