Caitlyn Jenner | $100 MILLION

Once an Olympic gold medal-winning decathlete, William Bruce Jenner, is now a famed transwoman going by the name Caitlyn Jenner. For 65 long years, Caitlyn was an accomplished man and went by his original name William Bruce Jenner. In 2015, she decided that she’d live as a woman. From her humble beginnings of living in a one-bedroom house in Malibu Hills, she worked her way up to build a $100 million net worth.

Of course, most of the income came from her TV reality series I Am Cait and the royalties of her book credit in The Secrets of My Life. Prior to her career in the limelight and after her successful Olympic career, Caitlyn appeared in a box of Wheaties and became its spokesperson, but was replaced by Mary Lou Retton in 1984. She also appeared in a few TV shows like CHiPS, 20/20, and Keeping Up with Kardashians.