At heart, Stupak is a gambler. What elevates him above your usual assortment of card sharks is an entrepreneurial instinct and the persistence to lay it all on the line, time after time. Even 'Ol Blue Eyes would be proud of how this guy picks himself up and gets back in the race.

When he arrived in Vegas, Stupak had already run illegal card games in his hometown of Pittsburgh, fashioned himself a lounge singer under the moniker "Bobby Star," raced motorcycles, sold coupon books, and hit it rich with a giant telemarketing gig down under. Flush with cash, Stupak took his first steps in Vegas with Bob Stupak's World Famous Historic Gambling Museum. Off the strip and anemic by Vegas standards, the place burned down within two months of opening.

Stupak was undeterred, opening his Vegas World with insurance booty from the fire and some assistance from legendary banker E. Thomas Parry. Using his knowledge of card games, Stupak created hundreds of gimmicks that made gambling at Vegas World unlike anywhere else in the world. Though he was still off the strip, his willingness to take, and make, big bets at his sports book and relentless self-promotion made his joint a success. It also cost him a few million in gaming board violations.

When you're born to take risks, success is just a means to a much bigger jackpot. Not content with a profitable hotel/casino, Stupak wanted to make his mark on the Vegas skyline, and construction of the Stratosphere Tower began before he'd even found investors. With a near-fatal motorcycle accident, a fire during construction and a small pool of willing investors, it would seem the project was doomed. Not for Stupak. Nothing was going to stop his dream of a towering billboard that promoted itself.

Though the Stratosphere went bankrupt under his guard, it still stands as a testament to the real Vegas spirit. True to that, Stupak soldiers on, looking for the next wager worth making.