Ashton Kutcher's Surprisingly Successful Tech Investments

From Skype to Foursquare, the entertainer's smart decisions in the startup space make most venture capitalists look like amateurs

After a couple of failed investments, Ashton Kutcher (previously known for, what, a starring role on That '70s Show? His part in the stoner comedy Dude, Where's My Car?) was convinced by Silicon Valley heavyweight Marc Andreessen to risk some of his money on Skype. He hasn't looked back since, quickly building a portfolio that would make the most successful investors jealous.

But he doesn't get a lot of coverage. At least not as much, in the tech press that is, as Peter Thiel or Ron Conway or Paul Graham. And that's probably because he still describes himself as an actor. In a recent profile in the New York Times, Jenna Wortham, a technology reporter for the paper, calls Kutcher "the most prominent entertainment figure in the high-tech venture capital game," but it might be time to switch those associations. Kutcher has invested in so many -- and had so much success with -- startup companies, that he might be called a venture capitalist first and an actor second.

Even with the Times, Kutcher would not disclose the amount of money he puts into his new investments, but Wortham's sources in the venture capital sphere estimated the range to be between $50,000 and $200,000 per property, which is a typical amount for many early-stage buy-ins. What he gets back could be many times that amount. That Skype investment? It was made in 2009 when the Internet calling service was valued at $2.75, a figure many dismissed at outrageously high. Earlier this year, Microsoft purchased Skype for more than $8 billion.

It's just one of several success stories. Here, we've collected fifteen properties that Kutcher has invested in. (He's made at least a dozen undisclosed investments in addition to these.) With many of his early investments, the venture capitalist/entertainer reached out to the founders and put his own money down. Today, he makes most of his decisions with his partners at A Grade Investments, Guy Oseary, also known as Madonna's manager, and billionaire Ron Burkle.

Image: Paulo Whitaker/Reuters.