The 10 Richest Self-Made Women in America The top spot goes to ... a roofer By Arden Dier, Newser Staff Posted Jun 2, 2016 7:20 AM CDT 7 comments Comments Oprah Winfrey in New York in October. (Photo by Greg Allen/Invision/AP, File) (Newser) – As USA Today puts it, "the richest self-made woman in America is a roofer." Diane Hendricks, who owns America's largest wholesale roofing and siding distributor, tops Forbes' second annual list of the country's richest self-made women—meaning they earned rather than inherited their cash. The youngest woman on the list is 26-year-old Taylor Swift with a new worth of $250 million, but she sits at the 60th spot. Here's the top 10. Diane Hendricks, co-founder of ABC Supply: $4.9 billion Oprah Winfrey, TV personality and Weight Watchers rep: $3.1 billion Judy Faulkner, CEO of Epic Systems: $2.4 billion Doris Fisher, co-founder of Gap: $2.4 billion Johnelle Hunt, co-founder of J.B. Hunt Transport Services: $2.3 billion Marian Ilitch, co-founder of Little Caesars: $2.1 billion Meg Whitman, Hewlett Packard CEO: $2.1 billion Lynda Resnick, co-owner of Wonderful Company and Fiji Water: $2 billion Jin Sook Chang, co-founder of Forever 21: $1.9 billion Judy Love, co-owner of 300 gas stations and convenience stores: $1.9 billion Click for the full list or see why one woman suddenly dropped off it completely.