Trump's image as a "great businessman" was something created for TV. He was floundering before he was recruited by Mark Burnett to do "The Apprentice".
His real life board room was too shoddy to be used on the series and a set of a board room had to be created for the show. He was essentially a joke in NYC before the series started.
https://www.youtube.com/watch?v=pxxrNhEI3Jg
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