Serena Williams

She earned $94 million in career prize money — the most in women's tennis history — but Serena Ventures has invested in 78+ companies including MasterClass, Tonal, and Impossible Foods, with a combined portfolio valuation exceeding $14 billion. She also owns stakes in the Miami Dolphins and Inter Miami CF, adding sports equity rarely seen among female athletes. Her S by Serena fashion line and lifetime Nike deal generate ongoing revenue streams. Retired in 2022 with 23 Grand Slam singles titles, she remains one short of Margaret Court's record — a gap that fuels her relentless ambition.