8. Play The Establishment
Vince McMahon has always had a love / hate relationship with the establishment. The thing is, getting on with the powers that be is a necessity. Even when the master of his own company, he has still had many masters to serve in the television and entertainment industry. At a corporate level, it is all about networking and doing the right deals. For McMahon, he has longed for mainstream acceptance from the establishment. Particularly in the late 80's New York scene, he'd go to all the right bars and try to impress all the right people. But he was always met with snubs and mocking, save for a few guys like NBC executive Dick Ebersol. It was Ebsersol who opened a lot of doors for McMahon, proving that connections do matter. But at the same time as continually courting the establishment, McMahon is loathing of it. He has said in interviews that he prefers to go to the bar and chat to the waiter, rather than schmoozing with high society types at fancy functions. He even designed the Hunter Hearst Helmsley character as a dig at snobs in his neighbourhood. It is fine balance in the search for success, you have to get on with the right people, at the same time as doing your own thing. McMahon's done a fairly good job of walking that line.