![]() 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.
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