Who he is: Co-founder of Curves International
How he lost his money: In 1976, Heavin dropped out of college at age 20 and started his first gym, Women's World of Fitness. Success came right away, and he was a millionaire by age 25. However, Heavin's aggressive expansion plans didn't add up. He added amenities to the gym, such as tanning beds and swimming pools, that were expensive to maintain. "At 25, it was all about me, and that's a foundation for disaster," Heavin told Kiplinger. By 1986, overhead costs began to exceed the amount the company was bringing in from new memberships, and at age 30 his business went bankrupt.
How he came back: Tried again with the same business idea, applying lessons learned from his initial failure.
Marrying his future business partner, Diane, gave Heavin the motivation he needed to give entrepreneurship a second try. In 1992, the couple opened the first Curves, a women-only gym, in Harlingen, Texas. Heavin once again found immediate success. In 1995, the pair turned the business into a franchise; today, there are 10,000 Curves locations across the world. In 2000, he released his first book, "Permanent Results without Permanent Dieting: The Curves for Women Weight Loss Method," and it became a New York Times bestseller. On finding success a second time around, Heavin says, "I had to lose everything I owned before I was capable of running a business the right way." Today, he's a billionaire.