Tommy Hilfiger, age 67
At the age of 20, Hilfiger opened his own clothing store but he went bankrupt after 5 years. After that, he has moved to New York where he worked for several labels. By the age of 28, he created his own clothing design company called “Tommy Hill.” 6 years later, with the help of sponsors, he established the Tommy Hilfiger Corporation, which soon became one of the most famous clothing brands in the world.