I agree he is a promoter first but any successful business man takes risks and sometimes those risks fail. Stock pickers sometimes pick bad stocks. Baseball pitchers sometimes pitch bad throws. If he never failed be would never take risks.
The real issue is does he learn from his failures and avoid them in the future. He failed in Iowa, does he learn from that in other states?
I'll concede that, but, a true leader takes responsibilities for his failures, and doesn't stiff the creditors. He wouldn't be nearly so rich if he had manned up, and paid back his losses.
You can’t steal Second base while keeping one foot safely on First. And occasionally you get picked off.