That was my impression before the election, when I didn't pay any attention. I thought he was a successful bully, which wouldn't necessarily be the worst combination for a President.
After learning about his actual business history (Thanks, Trump Inc.! podcast) I think the 'succeeded' part is pretty arguable. He was born unbelievably wealthy, had a string of some unbelievable business failures, and was subsequently bailed out by some known (Deutsche Bank) as well as unknown shady actors and practices.
Now that I understand his business history, I wouldn't consider him to have succeeded in business. He could have been vastly more wealthy today by doing nothing other than invest in index funds, which to me counts as largely unsuccessful.