They opened their books to FORBES, and the numbers are a lot more impressive than Dude, Where's My Car? Over six years they've turned their $30 million fund into a cool $250 million. And that's precisely what makes Kutcher and Oseary so compelling. And while those five have all been known to enjoy the taste of fame and glitz, a decidedly more staid backer, Liberty Media, recently tossed them $100 million to put to work-and to do so without Burkle, who until now has partnered actively with them.Īs a public company Liberty Media must live and die by its numbers. Except that a slew of self-made billionaires-including Ron Burkle, Eric Schmidt, Mark Cuban, David Geffen and Marc Benioff-gave them millions from their personal stashes to invest. It would also be easy to write off Kutcher, 38, and Oseary, the 43-year-old manager of U2 and Madonna, as amateurs who trade coolness for deal flow. But Kutcher's and Oseary's portfolios, which number more than 70 investments combined, include a roster of grand slams way past Uber-Skype, Airbnb, Spotify, Pinterest, Shazam, Warby Parker-with valuable startups like Zenefits and Flexport still gestating. William Shatner, after all, never has to work again after hitting it big with Priceline, and no one's going to confuse Captain Kirk with Kirk Kerkorian. It would be easy to chalk that up as one lucky bet.