Molly Bloom

Yes, she had a Italian mobster put a gun to her head. Yes, the buy-in for her underground high-stakes poker game, where regulars included Ben Afleck and Toby Maguire, was originally $10,000 and eventually grew to $250,000. Starting as a waitress at the games, Molly Bloom eventually became the banker and once saw a man lose $100 Million in a single night. Bloom originally aspired to reach the highest level of mogul skiing, the Olympics, not the lowest depths of an FBI raid, which came after she began taking a percentage of the pot and broke a federal law. Bloom's wild tale was made into a fascinating movie, "Molly's Game"