Former New York Giants running back Tiki Barber amassed 10,449 rushing yards, and millions of dollars, over his 10-year NFL career. Even though he retired with a few good years left in the tank, Barber holds almost every franchise record. After retiring Barber landed a nice gig at NBC Sports, but quickly lost his job after rumors of him dating a 23-year old intern became public (against company policy). According to reports, Barber has tried to establish himself as a “serial-entrepreneur” investing in everything from bottled water, cycling gyms, and event planning websites. Not to mention the fact he’s written eight books with his brother, former NFL star, Ronde Barber. There is little information available describing how Barber managed to squander some of his NFL riches, but one can only assume it has to do with failed business deals.