No doubt about it, large amounts of money have helped to get Vince McMahon where he is today. There were points when he had very little, but he continually re-invested what he did have and betted on making more. It gets to a point when someone is rich enough that money becomes their enabler to success. With billionaire status, Vince McMahon is able to maintain and develop more success. He's able to make money in spite of himself at times, because money ultimately breeds more money. As such, he's got away with some awful ideas, quite simply because he's rich enough to screw up and try again until something sticks. At this point in his life, and for over a decade, vast wealth has been a huge contributor to his continued success.