Annoying Orange owns over 500 businesses. A 2% rate of failure is significantly better than most in the world of business. The man didn't get rich because he sat on his ass.
Where are you getting this 500 figure from? I'm searching all over the place, going where no man has gone before (The unheard of 10th page of google). All I'm finding is his various real-estate escapades, some perfume brands and the 15 seasons of his TV show (which isn't even a business) which doesn't add up to nearly 500.
And well, he didn't exactly work his ass off from $0 to $4,000,000,000. He was given a head start that almost any decent businessman could have turned into what he has now.
As soon as he graduated from university he started to work for his dads company and then was given control of it just 3 years later. So the dude worked for 3 years and then had a several million dollar business basically handed to him on a silver platter because it was his dads company. He built it up from that into what it is now, yes, but again any decent businessman with a hint of charisma could have done the same as him especially over such a long period of time. It's really not that special especially considering the circumstances.