Ashton Kutcher took the stage with Charlie Rose at the TechCrunch Disrupt conference this week to talk about his new hobby: venture capitalism. Most famous tech-wise for his relentless championing of Twitter, Kutcher turned some heads with early stage investments in startup darlings like Foursquare, iPad reader Flipboard, photo-sharing site Path and most recently Airbnb, a schmanzy-er version of Couchsurfer.com. Investing in tech companies started off rocky for the Punk'd star. Kutcher admitted to Rose that his first foray into startups with the fated Ooma, an internet-based phone company in which Kutcher both invested and served a managerial role, failed in 2004. It wasn't until Netscape founder Marc Andreessen approached him in 2009 to invest in Skype that Kutcher hit a cord. "He came to me and said Skype could use some help with being more popular in the U.S. and we would like to bring you on to do that,” Kutcher said.

Making things popular seems to be Kutcher's primary appeal to buzz-hungry startups and their ambitious investors. According to a report in today's New York Times, Airbnb approached Kutcher with the same intentions as Andreessen and his not-yet-mainstream company. “We realized Airbnb needs to leverage pop culture and social media,” Airbnb founder told the Times, adding that Kutcher could offer both. "I have some expansive social media reach, but what I’ve become relatively good at is bringing things that aren’t mainstream…into the mainstream,” said Kutcher at the TechCrunch conference. With a combined 6.8 million followers on Twitter and 9.7 million fans on Facebook, Kutcher's social media dominance has won him spokesman roles at companies like Popchips, Nikon and Pepsi.

What Kutcher admits he lacks, however, is the knowledge of and patience for the details of investing. "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 told Rose in explaining how he'd "become immune" to conversations about things like market cap. In addition to Andreessen, Kutcher's friends include VC sluggers like Y-Combinator's Paul Graham, angel investor Ron Conway and billionaire Ron Burkle. Silicon Valley savvy meets Hollywood celebrity with the launch of Kutcher's new venture fund, A-grade, which is backed by Burkle in collaboration with Madonna's manager Guy Oseary. With the hope to invest in short-form content creators, A-grade complements Kutcher's other projects, Twitter curation app A.plus and production company Katalyst.

A year before being approached by Andreessen to invest in Skype--a deal in which Kutcher tripled his money after this month's Microsoft purchase--Kutcher eagerly announced Blah Girls at another TechCrunch conference. "Blah Girls, a South Park for teens, shot to fame and quickly flamed out, but Kutcher--who produced the Web cartoon under his Katalyst media company--made valuable connections in the tech space thanks to the production," reported Portfolio. Kutcher appreciates the learning opportunity, though. He told Rose this year, "The failures that we have are sometimes expensive educations."