I may have been a bit hyperbolic about freeloaders.

The bigger point I want to make is that the standard deviation on returns of a single venture like Trump's is so large that you cannot meaningfully compare it to a highly-diversified basket of stocks.

To use your analogy, it'd be like evaluating the effectiveness of a coach in a swimming event by picking a single one of their swimmers and comparing them to the average times of the U.S. Olympic team. Does this necessarily imply anything at all about the skill of the coach?