Ashton Kutcher, a former model, rose to fame in Hollywood by playing a handsome ditz in "Dude, Where's My Car?" and on "That 70s Show." But in certain circles, people know that he is no dummy when it comes to technology.
In recent years, Mr. Kutcher has become a smart early investor in some of the most talked-about Internet start-ups, including Foursquare, the mobile social network; Path, a photo-sharing application; and Flipboard, a news-reading app for the iPad.
He has also clearly mastered the utopian lingo of Silicon Valley: "I look for companies that solve problems in intelligent and friction-free ways and break boundaries," he said in an interview this week.
It is too early to say how Mr. Kutcher's approach will pay off, but one of his investments has clearly jumped in value. He was part of a group of investors that bought into the Internet calling service Skype in 2009 in a deal that valued it at $2.75 billion. Last month, Microsoft agreed to buy Skype for more than three times that amount.
Mr. Kutcher, 33, would not discuss the size of his investments, which he has recently been making through a partnership called A Grade. People in the venture capital world estimated that they were in modest amounts, perhaps $50,000 to $200,000 -- on par with what other early-stage investors would be putting in.
His firm's latest and largest investment, to be announced Thursday, is in 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.
Airbnb has more than 60,000 listings, from seaside apartments in Barcelona, Spain, to houseboats in the San Francisco Bay Area. It charges a fee for each reservation and says its users have booked more than a million nights through its service.
Many celebrities, including M. C. Hammer and Justin Timberlake, have flirted with tech businesses. Kim Kardashian, for one, is a founder of an e-commerce start-up called ShoeDazzle. But Mr. Kutcher is the most prominent entertainment figure in the high-tech venture capital game, and he puts more than his money into it.
He has been known to drop into General Assembly, a co-working space in Manhattan that is the home of one of his investments, the fashion site Fashism. He advised Path on ways to let users comment and give feedback on each others' photos. And on Monday, UberMedia, another of his investments, released A Plus, a free program for desktop computers that revolves around everything Ashton, including his Twitter updates, photos and other material he endorses.
"He gives capital, yes, but he also offers creative collaboration," said Dave Morin, who started Path and was an early employee of Facebook.
Mr. Kutcher's first forays into the tech industry were flops: an Internet calling service called Ooma in 2007, and an animated Web comedy show aimed at young women, called the "Blah Girls,." in 2008.
"We failed," he conceded on stage in New York this week at TechCrunch Disrupt, a technology conference.
But Mr. Kutcher's interest in the Internet grabbed the attention of several Silicon Valley heavyweights, including Marc Andreessen, the venture capitalist who was a founder of Netscape. He roped Mr. Kutcher into investing in Skype. Since then, Mr. Kutcher has built up a circle of fellow investors.
"I have a bunch of interesting and really smart people that I sit with and talk to quite frequently because of the investments I've made, and between their networks and mine, I get to see things really early," he said.
Mr. Kutcher initially invested directly in these companies, but he is now a partner in A Grade with the billionaire Ron Burkle and Guy Oseary, Madonna's manager.
David Lee, who co-founded SV Angel, an early-stage investment firm in Silicon Valley, said he once had doubts about Mr. Kutcher.
"When I first met him, I was deeply skeptical of him because he's an actor and famous, and I thought he just wanted to dabble," Mr. Lee said. "I've seen his movies, I've seen 'Dude, Where's My Car?' and was not sure what to expect."
But Mr. Lee said that as his firm began to collaborate with Mr. Kutcher's and invest in the same companies, he saw Mr. Kutcher in a different light. "I've come to realize he's one of the most insightful investors I've worked with," he said.
Adding to Mr. Kutcher's appeal, many say, is his extensive reach online and off. Besides his TV and movie audience, he has a large following on Twitter and Facebook -- 6.8 million and 9.7 million fans, respectively, which could help a start-up rise above the online chatter.
With Airbnb, the company had already built up a customer base and raised $7.2 million from Sequoia Capital and Greylock Partners. The only thing missing? Mainstream adoption.
"It felt like we are at a juncture where Airbnb is ready for the rest of the world," said Brian Chesky, one of the founders of the service. "We realized Airbnb needs to leverage pop culture and social media." Mr. Kutcher, he said, could help the company with both of those.
Mr. Kutcher was impressed by Airbnb's approach, which focuses on reviews of both the lodging and the lodgers.
"It's moving social trust into commerce," he said. "Your home is a very private place, so building trust around turning that into a consumer offering is unlike any other site."
First Published: May 26, 2011, 4:00 a.m.
