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a shton 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, Oseary and he 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.
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 venture capitalists,” 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 the age of 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 modelling competition, dropped out and moved to New York, then Los Angeles.
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, Oseary and he 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.
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 venture capitalists,” 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 the age of 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 modelling competition, dropped out and moved to New York, then Los Angeles.
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