Celebrity Investors That Outsmarted The Insiders

Ashton Kutcher

The “Two and a Half Men” actor is actually a savvy investor. His strategy? “I’m proactively funding brilliant people trying to solve hard problems. Focusing on this simple goal of identifying and enabling amazing entrepreneurs to create a better tomorrow is the crux of my investment strategy.” Born to middle-class parents in Iowa, Ashton Kutcher didn’t grow up with any business know-how other than the most important: a strong work ethic. His hard work and investment strategy paid off when he put $1 million into Skype in 2009. When Microsoft bought the company 18 months later, Kutcher’s investment quadrupled. A year later he co-founded A-Grade Investments which put $2.5 million into Airbnb, a stake now worth about $90 million. They’ve also invested in Uber, Spotify, Warby Parker and Houzz.