Dave Portnoy is an American sports media figure and internet entrepreneur who worked his way out of a place called, I kid you not -- Swampscott, Massachusetts – to become the CEO of one of the most popular sports content sites in the world, Barstool Sports, making himself worth an estimated $100 Million in the process. I don’t too much about Swampscott, but I’m willing to bet that most people born and raised there don’t imagine themselves ever accomplishing a feat like that, but from the very beginning, Dave Portnoy was a different kind of person. Someone willing to gamble big on success and despite it all, succeed.