Getty Images / Jeff Gentner | Vince McMahon and his wife, Linda.
After (just barely) graduating from East Carolina University in 1968, McMahon worked selling paper cups and crushing rocks at a quarry, a job he says he spent 90 hours a week at.
Finally, at age 27, he persuaded his father, owner of what was then known as the World Wide Wrestling Federation, to let him promote matches in the far-flung Bangor, Maine, region. The younger McMahon succeeded, climbed the company ladder, and he ultimately took over for his father in the early 1980s.
Soon after, McMahon began growing the company from a regional entity to a national one, and in 1984, he signed megastar Hulk Hogan.
As a result of his rapid ascent from rags to riches, McMahon is quick to dismiss people who say their upbringing has prevented them from becoming successful.
“When I hear people from the projects, or anywhere else, blame their actions on the way they grew up, I think it’s a crock of ****,” McMahon tells Playboy in a 2001 interview. “You can rise above it. This country gives you opportunity if you want to take it, so don’t blame your environment. I look down on people who use their environment as a crutch.”