Ashton Kutcher’s Smart Money Friends

Just don’t ask about 'Two and a Half Men'

Ashton Kutcher has no delusions about his talents. He’s an actor, a Twitter user, a producer, an endorser, a brand, and sometimes, he’s a businessman. He is not, however, a numbers guy. That’s why he’s befriended powerful moneymen like Ron Burkle, Marc Andreessen, Ron Conway, and Guy Oseary, and the relationships have paid off handsomely.

Charlie Rose interviewed the movie star and nascent venture capitalist at TechCrunch Disrupt this morning. Off-limits topics included Kutcher’s new role as star of Two and a Half Men and his hat (it was not a trucker hat, for those curious).

Within-limits topics included Kutcher’s lucky, lucky play for Skype, a deal he was invited into by Netscape founder and venture capitalist Andreessen. Based on the reported earnings of his co-investors, Kutcher likely minted 3x his money in just 18 months when the company sold to Microsoft this month for $8.5 billion.

He’s also backed high-profile startups like Foursquare, Ubermedia, Path, and Airbnb. His fund, called A-Grade, is a partnership between Madonna’s manager Guy Oseary, supermarket magnate Ron Burkle, and himself. And while Kutcher doesn’t bring number-crunching prowess to the table, his celebrity, his understanding of social media (he has a combined 9 million followers on Twitter and Facebook), and his talent for marketing brands (he’s worked with Levi's, Gatorade, Intel, and Pepsi) is invaluable to a startup. Good looks and a little charm don't hurt, either.

Kutcher admitted his investment know-how isn’t stellar: he’s “become immune” to conversations about macroeconomics and deal intricacies, he said. “That’s why I have a lot of friends who are a lot smarter about those things than I am . . . Let them be smart about that,” he explained to the audience at Pier 94. Of course, he wasn’t always so lucky to have experienced, well-connected dealmakers around. Kutcher’s first foray into the VC big leagues was a pitch for a company called Blah Girls, which Kutcher described as a South Park for teenage girls. “We thought we were really bright,” he said. Unsurprisingly, it failed.

Until he paired up with his trusted circle of tech heavyweights, Kutcher’s early success as a businessman remained in entertainment. He starred in and produced the TV prank show Punk’d, which worked, he said, because it mimicked the Internet. “[Punk’d] created ‘short attention span’ theater in the form of three- to five-minute segments. It was exactly the type of content units people were consuming on the Web,” he said. But Punk’d was early to the Web video market. In the early 2000s, “brands were just starting to come into entertainment properties on the Web,” he said.

Now, through his production company Katalyst Media, Kutcher hopes to create and deliver Punk’d-like bites of video online. “We’re trying to create a Y-Combinator model for short-form media creators for the Web,” he said. The timing seems right—Web video is having its moment. And the Y-Combinator business model? Kutcher has a friend for that. He counts Paul Graham, a partner at the incubator, among his circle of VC gurus.