Earlier quoted context omitted.
He's a pretty objectively terrible businessman. Like, that's the part that annoys me about him more than anything else, how he's convinced a lot of people that he's "good at business". He's not; if he had just dumped the money his father left him into basically any index fund between the 1970's until 2016, he would have made more money than he had in 2016. Any idiot can basically match the S&P500, just buy VOO or SPY…
He inherited billions and still manages to go bankrupt 6 times. The Apprentice was the OG reality distortion field and it's crazy people have trouble seeing through it all.
EDIT: Just fact checking this, it's the latter, 6 entities went bankrupt. It looks like the trump organization has 500 entities, so 1.2% bankruptcy rate.