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Celebrity Tech Investors Ashton Kutcher

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Ashton Kutcher

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Investments: In what could eventually become an interesting case of life imitating art, Kutcher will be playing an Internet billionaire as Charlie Sheen's replacement this fall on 2 1/2 Men. Over the last few years, Demi Moore's younger half has invested undisclosed amounts in some of the tech world's hottest start-ups, either independently or through his investment firm A Grade Investments. Some of his best-known deals include early-round investments in social magazine app Flipboard, location-based service FourSquare, vacation rentals web service Airbnb, and photo sharing app Path. He was also part of a group of investors that bought a stake in Skype in 2009 and later sold it to Microsoft for about three times what they'd put in.

Investing and celebrity don't always mix: His guest editing of a special issue of Details magazine about social media could potentially land him in hot water with the SEC, since the publication recommended some companies Kutcher has invested in without explicitly noting that fact.

Background: In a Q&A in Details, Kutcher says he first became interested in social media and technology after his production company did a deal with AOL to produce short-form content. But with the arrival of Facebook and Twitter, he soon realized he could access a large audience without having to go through a big media company. At a technology conference in May, Kutcher told interviewer Charlie Rose that he uses his training as an actor to evaluate potential investments: "As an actor, when we receive a script, we start breaking down every character by their want ... I look at technology the same way. I'll think, 'I'm a user of this platform. What do I want and how badly do I want it?'"

Fun fact: Kutcher's initial forays into tech investing — an Internet calling service called Ooma and an animated web comedy show called The Blah Girls — didn't work out so well, at least while Kutcher was still involved with them (he left Ooma in 2008). But they did bring Kutcher to the attention of Marc Andreesen, the venture capitalist and founder of Netscape, who wound up convincing Kutcher to invest with him in Skype.

Number of Twitter followers: 7.5 million (@aplusk)

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