Ashton Kutcher & Mila Kunis ($300 Million)

$300M combined. Kutcher turned $30M VC fund into $250M. Kelso wins.

Ashton Kutcher and Mila Kunis amass $300 million, driven by Kutcher's VC firm A-Grade Investments, which turned $30 million into $250 million through early stakes in Uber (12x return), Airbnb, Spotify, and Warby Parker—a track record that outperforms Ryan Reynolds' gin exit by 20% in ROI. Kunis adds $75 million from acting, including Bad Moms and Family Guy voice work, but the actor once known as Kelso is now Hollywood's most successful celebrity investor.

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