Kutcher was nothing like the dopey characters he played. He absorbed everything he could about the technology industry, resolving to use his trend-spotting skills in a more lucrative way. He worked with Guy Oseary, Madonna’s manager, to sort through all the opportunities, and ended up giving money to dozens of companies—not just in social media—including Uber, Airbnb, Spotify, and Instagram competitor Path. “Whenever there was a new type of experience for consumers, there would be like three companies doing the same thing,” he remembers. There were several versions of Instagram, Pinterest, and
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