Sean grew up in a neighborhood in which if you didn’t gamble, you didn’t belong. Bets began at a young age with friends, as they would play baseball with each other. In his early teens, a friend introduced him to a bookie, and Sean made bets on sports games right away, putting up bets of hundreds of dollars that he didn’t have. His losses would have the bookie knocking on his parents’ door. As he got older, he would come to idolize bookmakers, with their fancy clothes and cars but never holding a real job. In high school, he would work for bookies getting his peers to make bets. After high school, he started working a normal job but would take his paycheck gambling. His descent began with a stroke of luck, winning a five-figure bet when he didn’t have the money to cover it on the chance he lost.