How many businesses has he had and did they fail due to him making the same mistake?
He's declared bankruptcy with 6 businesses:
1. Trump Taj Mahal
2. Trump’s Castle
3. Trump Plaza Casinos
4. Trump Plaza Hotel
5. Trump Hotels and Casinos Resorts
6. Trump Entertainment Resorts
He's also tried his hand at selling steaks, vodka, water, ice, board games, mortgages, bicycle races, football teams, etc, and failed at all of them.
His major successes are a ghostwritten book that pretends he's a great businessman, a reality show that pretends he's a great businessman, and collecting fees for slapping his name on buildings other people build and usually own. During the trial it came out the crown jewel of his empire, Trump Tower in Manhattan, is actually barely profitable.
Of course, he's most likely laundering money and taking bribes. He probably has talent there. He also, to be fair, appeared to do well recently selling NFTS to suckers, as well as bibles and sneakers haha. And collecting donations so others can pay his legal fees.
Truth Social will also be bankrupt soon, but Trump does have the potential to grift a tremendous amount of $ from the rubes there.