[tptacek]

Without wading into the politics, as I understand it, had he to do it over again, taking his inheritance and simply investing it in the S&P 500 --- like any common schmoe --- would have produced superior returns.

That seems like the definition of an "unsuccessful businessman", but I'd be interested in the semantic interpretation where it doesn't.

[drak0n1c]

Success in business can also be defined as creating a sustainable entity that builds infrastructure/buildings, provides services, and employs people. The local Ben Franklin crafts and Ace Hardware franchisee in my hometown would qualify by that definition, though his personal profit may be higher if he had instead liquidated his family's holdings and put it all in an index fund.

If you define "successful businessman" strictly by comparative potential personal profit, that would rule out a great many people who have found happiness and decent profit in what they've built, and restrict qualifiers to the idle rich and a few unicorns. That's a break from how the word "success" is used in all other contexts.

[tptacek]

You'd then be defining "successful businessman" as a subjective X-factor. But that X-factor doesn't apply here; the argument above was that, as a successful businessperson, Trump has demonstrable competence in dealmaking. If he barely beats the S&P500 (or, depending which of 5 years in the late '70s or early '80s you start counting, severely lags it), that competence hasn't been demonstrated.

[kasey_junk]

This is a quagmire I let myself get swallowed in so often that its likely not healthy, but my favorite 'Trump' stories all revolve around the crazy things he is accused of that no 'successful' business person would need to do.

The best of course is the accusation that he tried to disguise his voice to convince a forbes reporter that he was richer than he was to get on the top 400 list:

http://fortune.com/2018/04/20/trump-lied-wealth-forbes-400-l...

This is actually my own pet conspiracy theory. He didn't want to release his tax returns because he's doing shady tax dodges, he did it because it proves he's not actually rich.

[hundt]

https://www.bloomberg.com/view/articles/2015-09-03/should-do...