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9. Kathy Ireland

Kathy Ireland
Kathy Ireland | Slaven Vlasic/Getty Images
  • Net worth: $500 million

Before she was a supermodel, she worked on a paper route. Kathy Ireland experienced a real-life rags-to-riches tale, making a name for herself as a model in the ’80s and a mogul through Kathy Ireland Worldwide. In 1993 she launched a sock line and the rest followed suit.

Kathy Ireland Worldwide rakes in an estimated $2.5 billion from retail revenue alone. Ireland owns resorts in Greece and Fiji as well as her own publishing imprint, Bendon.