Reese Witherspoon — From Teen Actress to $400M Mogul

Witherspoon debuted at 14 in The Man in the Moon (1991), won an Oscar at 29 for Walk the Line, then did something no actress had done: she built a media empire. Hello Sunshine produced Big Little Lies, The Morning Show, and Daisy Jones & The Six. She sold the company to Blackstone-backed Candle Media for $900 million in 2021. Her personal cut: approximately $400 million. She went from Legally Blonde to legally loaded. The most successful actress-to-executive transition in Hollywood history, and she did it by buying the rights to books before anyone else realized adaptations were the future.