Sophia Amoruso — Nasty Gal & Girlboss

Amoruso was dumpster-diving and shoplifting when she started selling vintage clothing on eBay in 2006. Nasty Gal grew to $100 million in revenue by 2012 — making her the poster child for millennial entrepreneurship. Then it all collapsed: Nasty Gal filed for bankruptcy in 2016. But Amoruso's story became a Netflix show (#Girlboss) and she pivoted to Girlboss Media, a community platform for women in business. She's no longer a billionaire — she may never have been — but her arc from dumpster diver to $100M revenue to bankruptcy to reinvention is the most honest entrepreneurship story on this list.