Is this Celebrity also a Secret Investment Whiz?

We know Ashton Kutcher can act, we’ve broken down laughing before his on screen antics, (just watch”Dude Where’s My Car,” or “That 70’s Show” reruns), but what we didn’t know about the Hollywood mainstay is what the New York Times (NYSE:NYT) is now reporting, that the former model has also been getting his hands dirty as a start-up speculator.

The betrothed and beloved of Demi Moore has apparently been hitting it big in Silicon Valley, as one of the earliest investors to jump in on Internet startups Foursquare, Path, Flipboard, and Skype (NASDAQ:MSFT) in recent years. Kutcher told reporters in a recent interview, “I look for companies that solve problems in intelligent and friction-free ways and break boundaries,” when asked about how he places his bets in the Valley.

It is unclear how much money the Hollywood funny-man has made through these transactions, though we do know that he was part of a group of buyers that got in on Skype in 09′ when the company was valued at $2.75 billion. Skype was recently purchased by Microsoft (NASDAQ:MSFT) for $8.75 billion, over 3x its valuation in 2009, so Kutcher likely rode his bucks to the bank on that deal.

According to the Times, Kutcher had made earlier VC forays, collaborating with smaller internet startups such as web-calling company “Ooma” in 2007. Kutcher recently conceded that his earlier ventures were less than profitable, telling a conference in New York bluntly “we failed.”

Now on the rebound though, Ashton was “roped Mr. Kutcher into investing in Skype” by Netscape founder and Valley legend Marc Andreesson, and has since become a partner in “A Grade,” a Cali-based venture capital group headed by billionaire Ron Burkle. Most recently, “A Grade” has been linked to “Airbnb”, “a start-up company in San Francisco that matches budget-conscious travelers with local people who are willing to rent out their spare bedrooms.”

As for Kutcher’s role in the deal, “We realized Airbnb needs to leverage pop culture and social media,”says co-founded Brian Chesky. Boasting followings of 6.8 million fans on Twitter and 9.7 million on Facebook, it seems as though Ashton is the right man for the job.

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