How Ashton Kutcher And Guy Oseary Built A $250 Million Portfolio With Startups Like Uber And Airbnb

• “You’re not even actually taking on the taxi companies–you’re taking on the notion of owning a car,” says Kutcher.
• “There was only one guy from our community that was not just doing it but even kicking my ass and getting in all the right deals,” says Oseary.

Eight and a Half X: TV star Ashton Kutcher and Madonna manager Guy Oseary teamed with billionaire Ron Burkle to turn $30 million into $250 million with investments like Uber and Airbnb. Liberty Media is betting $100 million the duo can do it again–on their own. (Photos: Tim Pannell for Forbes).

Ashton Kutcher, one of the world’s highest-paid TV actors, can obviously afford that most essential of Los Angeles celebrity luxuries: a car and driver. But he still prefers Uber. “We’re going to go to Warner Bros.,” he dictates, as we hop into a black Chevy Tahoe with Kutcher’s business partner, music manager Guy Oseary, in Beverly Hills. “So we’ll go to Moorpark and then hit the 101.”
There’s no need for directions. Our optimal route, from the gated enclave where Kutcher and Oseary live three doors apart to the lot in Burbank where the actor is filming his new Netflix series, is already programmed into the driver’s phone. But the ever confident Kutcher can’t help himself; in this car he’s the boss. Five years ago he and Oseary invested $500,000 in Uber–that stake is now worth 100 times what they paid.

“You’re not even actually taking on the taxi companies–you’re taking on the notion of owning a car,” says Kutcher. “That’s crazy. And that’s why it has the velocity and potential that it has.”

It would be easy to chalk that up as one lucky bet. William Shatner, after all, never has to work again after hitting it big with Priceline, and no one’s going to confuse Captain Kirk with Kirk Kerkorian. But Kutcher’s and Oseary’s portfolios, which number more than 70 investments combined, include a roster of grand slams way past Uber–Skype, Airbnb, Spotify, Pinterest, Shazam, Warby Parker–with valuable startups like Zenefits and Flexport still gestating.

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It would also be easy to write off Kutcher, 38, and Oseary, the 43-year-old manager of U2 and Madonna, as amateurs who trade coolness for deal flow. Except that a slew of self-made billionaires–including Ron Burkle, Eric Schmidt, Mark Cuban, David Geffen and Marc Benioff–gave them millions from their personal stashes to invest. And while those five have all been known to enjoy the taste of fame and glitz, a decidedly more staid backer, Liberty Media, recently tossed them $100 million to put to work–and to do so without Burkle, who until now has partnered actively with them.
As a public company Liberty Media must live and die by its numbers. And that’s precisely what makes Kutcher and Oseary so compelling. They opened their books to FORBES, and the numbers are a lot more impressive than Dude, Where’s My Car? Over six years they’ve turned their $30 million fund into a cool $250 million. The guy who until recently starred in Two and a Half Men has generated almost 8.5x.
“If you can routinely return 3x, you’re considered one of the best VCs,” says Marc Andreessen, a Midas List regular who’s raised more than $4 billion over the years with his firm, Andreessen Horowitz. “If you can return 5x, it’s considered to be a home run. I took my math classes: 8x is seriously higher than 5x.”
Andreessen isn’t alone in his appreciation. Talk privately with the heavies in Silicon Valley who have spent time with Kutcher and Oseary and watched them in action, and you hear and see the same story: These guys are legitimately smart. No “for Hollywood types” caveats. Their surprising success underscores two universal truths: how simple it is to manage other people’s money and how hard it is to do it well.
THE STRANGE ROAD OF ASHTON KUTCHER, venture capitalist, starts with a now bankrupt rapper: Curtis “50 Cent” Jackson. A decade ago 50 Cent took an equity stake in Vitaminwater parent Glaceau in exchange for becoming the face of the beverage–and earned an estimated $100 million when Coca-Cola purchased the company in 2007.
“I had done a [traditional endorsement] deal for Nikon at the time,” Kutcher recalls over a California breakfast of eggs and avocados at Oseary’s home. “I’m like, ‘Whoa, hold on, wait a second. I’ve got to figure out how to get in the equity game, because it just makes so much more sense.’”
Everything about Kutcher’s journey has been intuitive. Born to middle-class parents in Iowa, he didn’t grow up with any business know-how or lessons other than the most important: a strong work ethic. He was working construction with his dad by age 10; in high school he had a series of odd jobs, including janitor, butcher and factory worker at General Mills.
The brains were always there: When he enrolled at the University of Iowa, he planned to major in biochemical engineering–until he won a modeling competition, dropped out and moved to New York, then Los Angeles.
His big break came in 1998 with That 70s Show, where he starred as dopey hunk Michael Kelso, followed by a string of similar film roles. But while he was being typecast for stupidity, he began honing his chops. In 2003 he created and hosted a hidden-camera practical-joke show for MTV, Punk’d. By the time his Vitaminwater inspiration struck, he’d founded a full-blown production company, Katalyst. His digital chief, Sarah Ross, whom he’d poached from TechCrunch, began introducing him to Silicon Valley elites, including Ron Conway and Michael Arrington. “I spent 90% of my time just listening,” says Kutcher.
“There was definitely a period there in which very, very few people outside the Valley were taking any of this stuff seriously,” says Andreessen. “He started doing it when it really wasn’t cool.”
He learned his lessons well. Kutcher is fluent in the language of tech startups, and it isn’t just token jargon. At a private dinner at the Forbes Under 30 Summit last year, Kutcher spent a half-hour leading a vigorous debate with a bunch of media heavies on the correct ratio to optimize Web traffic and digital advertising revenue. He is, in essence, the football jock who started hanging out with the math nerds and eventually demonstrated that he was one of them. “Once you learn how to identify a snow leopard,” says Kutcher, “it’s pretty easy to see a snow leopard coming along.”
Andreessen invited him to plow $1 million into Skype in 2009. When Microsoft bought the company 18 months later, Kutcher’s outlay quadrupled in value. He was hooked. More important, he impressed his new friends in San Francisco, who were still recovering from the Great Recession.

Oseary, meanwhile, was undergoing a similar metamorphosis. Born in Israel, he moved to Los Angeles at 8 and ended up at Beverly Hills High School, where he started managing small-time hip-hop acts and mingling with the children of Hollywood power brokers like Freddie DeMann. The music manager hired a teenage Oseary to work for him at Maverick Records, the label he cofounded with Madonna. Through the mid-1990s Oseary rose from talent scout to chairman, overseeing a roster that included Muse and Alanis Morissette.
“A lot of what I do now is very similar,” he says, “which is trying to identify talent and then help them market their music [and] their vision.”

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Bitten by the startup bug, Oseary developed a relationship with Bill Gross, who raised over $1 billion for his Pasadena incubator, Idealab, in the late 1990s. But when the market cratered in 2000, it wiped out many of his burgeoning tech companies, along with plans for an IPO–and millions from Oseary, who’d gone all-in on Idealab. To add salt to the wounds, when former CAA agent Seth Rodsky offered him a chance to invest in the same Vitaminwater deal that would enrich 50 Cent and inspire Kutcher, Oseary declined.
Around the same time, he befriended Burkle, who told him the Idealab debacle was a blessing in disguise: He’d learned a valuable lesson at age 27. Oseary soon took over as Madonna’s manager, guiding her to back-to-back world tours that grossed a combined $600 million. When Rodsky came to him in 2008 with a chance to invest in Vita Coco, Oseary wrote a check for $1.2 million; the company’s valuation has increased from $28 million to $664 million since 2007. Next he scored big again with Groupon. As he began delving deeper into startup funding, he found the entertainment business heavily underrepresented in Silicon Valley.

“There was only one guy from our community that was not just doing it but even kicking my ass and getting in all the right deals,” says Oseary. “It was Ashton.” When Oseary proposed joining forces, Kutcher agreed.