Trump's greatest attribute/detriment has always been his willingness to take everything he owns and plow it into an idea that he believes in, and then do it again. When it works, everything is sunshine and roses. When it doesn't, you crap out. Trump is a gambler, pure and simple. Sometimes he's the calculating gambler -- the card counter at the single deck blackjack table. Sometimes he's the guy who's rubbing a magnet on the side of a slot machine to get the right symbols to come up. But, he's the guy that's going to play all of his chips on every hand, and come out a big winner, or a big loser.
If you've watched the show, or followed Trump regularly, you'll know that the key words in his life are "bigger and better" -- whether it be wives (better, not bigger), buildings, investments or whatever, the thing Trump strives for is to live up to his namesake and trump the competition, whoever they might be.
Simply put, this is why some will look at him and admire him, while others will look at him with disdain.
Self-made? Not exactly, but then again, I bet nearly all of us feel we had an "average" upbringing--though I'll be willing to wager that that "average" upbringing varies greatly among us. Trump has increased his position in life through a combination of skill, talent, guts, luck, and opportunism.
His stock is down 900% since the IPO in 96....not very impressive.
I admire his moxie but I steer clear of self aggrandizers like him routinely in my own business life.