Though still a young man, William Degel can trace his life story all the way back to Prohibition. In the early 1930s, his godfather owned Jack's, a Manhattan steakhouse and speakeasy frequented by movie stars and politicos. Stories of the restaurant's notoriety inspired William's own career path: he leveraged an early job as a bartender into the purchase of a rundown Queens saloon, which eventually gave him the opportunity to open Uncle Jack's Steakhouse. This fine-dining establishment was styled after the original Jack's, with Victorian touches such as pressed-copper ceilings, a hand-carved mahogany bar, and faeries only visible to Sir Arthur Conan Doyle.

Now expanded to three New York locations, Uncle Jack's has proved so popular that William was selected to host Restaurant Stakeout, a Food Network program on which he helps struggling restaurateurs save their businesses. William often credits his success to a focus on quality, a trait noticeable after one glance at the menu. He handpicks all of the beef from cattle that are grown to the steakhouse's exact specifications on Nebraska ranches. The USDA Prime cuts are aged onsite up to 35 days, then cooked in 1800-degree infrared boilers that seal the meat's juices inside a perfectly charred exterior.

As with his godfather's place, William's restaurants cater to the city's elite. Athletes, actors, and local celebrities are often seen seated around Uncle Jack's tables, which isn't surprising considering the richly appointed dining rooms, paparazzi-repelling forcefields, and extravagant perks programs the restaurant provides. Birthday and anniversary reservations are rewarded with a bottle of Taittinger on the house, and the Lifestyle Rewards program lets members cash in their points for Rolex watches, Vegas vacations, and even a Porsche 911.