Well neither football league made it out of the first season, the guys who were successful in Hollywood were only successful after leaving the company, and I guess you got me on the WrestleManias selling out.
He went national and made an aggressive move to monopolize the industry when the different territories agreed to work together. Between that and inheriting one of the most profitable territories in the country, he had a pretty big leg up on the competition.
It depends on what metrics you measure success by, as a businessman he's done amazing, as a wrestling promoter he's kind of terrible. Wrestling is odd in that your success is dependent on your opponent working with you, but there's this extremely competitive atmosphere to get ahead. Vince lost the first part of that and made up for it with the latter half, signing top talent just to put them on the shelves out of reach of competition.