Sure, he got into the business with help from his dear old dad, promoter Vincent J. McMahon. But after buying his dad’s company in 1982, the younger Vince turned it, unleashing Hulkamania along the way, into a worldwide phenomenon that has at times been rumored to be worth over $1 billion. We wonder if he decided to stick with wrestling after his stint at Fishburne Military School in Waynesboro, Virginia (he’s shown here in 1964 during his senior year), taught him that in the military, the outcome of the fight isn’t predetermined.