Becoming Superman

October 18, 2010, 7:00 AM UTC

A few years ago Jeff Skoll, recently arrived in Hollywood from Silicon Valley, took a call from George Clooney. Clooney had directed Good Night, and Good Luck, one of the first films that Skoll financed, and positive reviews had begun fueling Skoll’s reputation for backing serious projects. Clooney, it turns out, was doing someone else’s bidding: Veteran newscaster Dan Rather wanted an introduction. “Well, George,” Skoll teased the perennial Sexiest Man Alive. “I hate it when people use you to get to me.”

This is how life has changed for the 45-year-old Skoll: Because he is superrich (he was the first full-time employee of eBay) people want access to him — and they’re willing to go to extraordinary lengths to get an audience. It amuses him and his friends, many of whom confess to wanting to shield him from opportunists and glad-handers. Skoll, you see, is about the shyest, quietest, humblest media mogul and philanthropist imaginable. “He’s not in the swagger game,” says Jim Berk, the entertainment industry executive Skoll hired to run his film company, Participant Media, which he founded in 2004. “If you put 50 people in the room and tried to find the billionaire, you’d get into the 40s before you found Jeff Skoll.”

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You may not recognize Skoll, but you certainly know his movies and many of his friends. On a windowsill of his Beverly Hills office sits a framed photo of Skoll with actor Matt Damon on the set of Syriana, which Participant funded. Another picture shows Skoll with Robert Redford, who tapped the film industry newcomer to help build an arts center at the Sundance Institute. He’s signed Bill Gates and Warren Buffett’s Giving Pledge. His wall displays a photo of Nelson Mandela — taken by Tipper Gore. Skoll helped turn Al Gore’s traveling lecture into the highly profitable and Oscar-winning global-warming film, An Inconvenient Truth. He and Truth director Davis Guggenheim teamed up again to produce Waiting for “Superman,” a new documentary about America’s schools that is garnering rave reviews and Oscar buzz.

Skoll may be one of the latest carpetbagger billionaires to roll into Hollywood with dreams of making movies. He’s worth $2.5 billion, all of which came from his early grants of eBay (EBAY) stock. But unlike predecessors like Howard Hughes, Skoll isn’t preoccupied with meeting starlets or expanding his fortune. In fact, he’s pretty sure he’s going to leave town with his wallet a bit lighter — and that’s okay with him, since he has bigger ambitions: saving the world.

Skoll’s films aren’t typical Hollywood fare: They tackle weighty subjects such as eco-Armageddon, petro-terrorism, education reform, and women’s rights. In short they tend to reflect Skoll’s progressive, and ultimately optimistic, worldview that shining a light on the world’s problems will inspire people to band together to bring about change on a large scale. (Indeed, the name “Participant” evokes a call to action.)

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And while he’s been willing to finance a few money-losing movies, Skoll remains an unabashed capitalist who believes good works supported by entrepreneurial urges — a combination he calls the “double bottom line” — can cure all kinds of societal and economic ills. His Skoll Foundation advocates “social entrepreneurship,” a teach-them-to-fish variant of philanthropy that stresses market mechanisms over handouts, and he convenes an annual event, the Skoll World Forum, that tries to find ways to use technology and business to affect social change. (For all his modesty, Skoll understands the value in using the Skoll “brand” to promote his causes.) Even his private wealth-management firm, Capricorn, aims to make “principled” investments in companies such as a sustainable salmon fishery. Participant shrewdly invested in mainstream studio Summit Entertainment, best known for the Twilight vampire series.

As Skoll’s reputation and credibility as a film producer grow, though — his movies have garnered more than a dozen Academy Award nominations in just a few years — industry skeptics doubt production company Participant can avoid “going Hollywood,” and it will inevitably be making bigger, less-cause-oriented films.

Skoll, who says he personally approves every script Participant green-lights, thinks he’ll have no trouble finding high-quality material that matches his passions. “Virtually everyone I talked to — a writer, an actor, a director, an agent, a lawyer — said the projects they were most proud of in their careers had been the ones that made a difference in some issue that they cared about,” he says. “And they recognized that the system was really not set up to do those kinds of films.”

“If you put 50 people in the room and tried to find the billionaire, you’d get into the 40s before you found Jeff Skoll,” says one movie exec.

For all his hobnobbing with bold-faced names, Skoll has flown under the radar for a decade now. He grants few interviews about his work and is even more guarded about his personal life. He prefers to stand at the sidelines of the high-wattage events he attends — including those his own organizations host. A genuine aversion to the limelight seems in part to explain his low profile. Another explanation is his provenance. “There’s a part of Jeff that is really Canadian: quiet, not brash, not boastful,” says Roger Martin, dean of the University of Toronto’s business school and a director of Skoll’s foundation. “Canadians are like Americans, but dialed down.”

Skoll was born in Montreal and grew up in Toronto. A bookworm as a kid, Skoll figured he’d be a writer, but the entrepreneurial bug interrupted his scribbling urges. He started two small tech companies in Canada after earning a degree in electrical engineering from the University of Toronto. His entrepreneurial instincts eventually made him into an extremely wealthy man. He moved to the U.S. to attend Stanford’s business school, and after graduating in 1995 his friend Pierre Omidyar asked him to help him make a company out of his after-hours hobby. At first Skoll turned Omidyar down, but eventually he agreed to be eBay’s first president. He wrote the company’s business plan, handled all things financial and operational, and generally applied a level of business rigor that Omidyar, a software engineer, couldn’t have done himself. “In many ways, Jeff is the unsung hero of the early days of eBay,” says Meg Whitman, eBay’s longtime CEO and currently the Republican candidate for governor in California. “At my early staff meetings, Jeff was the one with all the analytics. It was very unusual for a startup.”

It was also at eBay that Skoll had his first brush with how public policy affects people, in this case himself. Despite the fact that 3,000 people reported to him, his visa application had been denied, threatening his ability to remain in the U.S. Steve Westly, another early eBay executive turned politician, had been urging Skoll to get involved in politics. “He told me, You’re either a participant or a victim,” says Skoll. “After my visa was denied, I went to him and said, ‘Okay, Steve, I’m a victim. Now what do I do?’ ” (What connected tech execs do is call Sen. Dianne Feinstein, who helped him resolve matters, says Skoll, who has since become a U.S. citizen.) When Skoll left eBay after four years at the company, he was a man with a purpose. He decided to return to his childhood passion for telling stories, and decamped for Hollywood, where he was simultaneously wooed and discouraged by media veterans. “I kept hearing similar phrases,” he says. ” ‘The streets of Hollywood are littered with the carcasses of people like you who think they’re going to come to this town and make movies.'”

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Undeterred, Skoll founded Participant in 2004 with the heretical notion that he would finance only films with a social message. Skepticism notwithstanding, everyone takes a meeting with a billionaire, and Skoll hired the Creative Artists Agency to introduce him to people who mattered. Industry stalwarts took him under their wings. “I had a protective feeling about him initially because he was new in a town full of smarmy, ultrasmooth people,” says Robert Redford. The naysaying died down when Participant got out of the gate fast with high-quality, if not financially successful, movies like Syriana and Good Night. Participant-backed films earned 11 Oscar nominations in 2006 alone.

Participant is unique in Hollywood, where profits rule. “Everything I put into Participant, I don’t expect to get back,” explains Skoll. “I expect the money to be refunneled to do more films and more projects.” The upshot is that while profits are preferred, a film doesn’t have to kill at the box office for Skoll to consider it a success. North Country, a 2005 film starring Charlize Theron as a single mom facing sexual harassment in Minnesota’s iron ore mines, made a mere $6 million its opening weekend, a bomb financially. Yet its release coincided with Congress’s consideration of an extension of an act punishing violence against women, legislation that wasn’t a “slam dunk” in the Bush era, notes Skoll. Participant screened the film on Capitol Hill and otherwise drummed up support for the bill, which was enacted. “From a social-action standpoint, it accomplished exactly what we set out to do, and we’re very proud of it.” Another Participant film, The Visitor, a sorrowful and charming story about the plight of illegal immigrants in the U.S., was partly inspired by Skoll’s own immigration problems.

Good films matched with Hollywood’s aspirational do-gooderism means heavy-hitters are gravitating toward Participant. Director Steven Soderbergh made the quirky corporate price-fixing drama The Informant, starring Matt Damon, with Participant. Soderbergh also is directing the upcoming star-studded thriller Contagion, which plays to another Skoll concern, global disease. Though Warner Brothers (like Fortune, a unit of Time Warner (TWX)) is best known for so-called tent pole movies that appeal to the masses, executives at the company say they’re happy to co-invest with Skoll. “There’s no eye-rolling over him,” says Alan Horn, president of the studio. “He doesn’t just throw money at the wall.”

Indeed, Skoll has made some savvy business deals since coming to Hollywood, proving that he’s more than a vanity filmmaker. In 2007 he bought a significant chunk of Summit Entertainment, the “mini-major” studio behind Twilight and The Hurt Locker. Skoll then signed a nonexclusive distribution agreement with Summit, which will enable Participant to distribute its films more efficiently than other production companies of its size. In a separate deal widely praised in Hollywood finance circles, Participant last year persuaded Imagenation Abu Dhabi, a government-backed investment vehicle, to establish a $250 million fund to finance 15 to 18 films over five years, a move that essentially enables Participant to make movies without relying exclusively on Skoll’s money. And yet something perverse has started to happen: Less than a decade after the billionaire arrived in Hollywood, filmmakers are interested in more than Skoll’s money. They want his name attached to their projects too. “There’s an incredible continuity to [Skoll’s film portfolio],” says Waiting for “Superman” director Guggenheim. “Before you know it, you’re going to say, ‘You know, all these movies that Jeff is making are adding up to a larger statement.'”

If Skoll is slowly gaining recognition in Hollywood, he’s already a superstar in the discrete corner of philanthropy known as social entrepreneurship. At the Skoll World Forum, the Skoll Foundation makes a handful of grants to organizations whose programs encourage those in need to help themselves. Past recipients include Wendy Kopp’s Teach for America and lesser-known outfits like KickStart, which sells inexpensive irrigation pumps in Kenya.

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What makes Skoll’s aid unique is that it’s unrestricted, meaning that organizations can spend the grants — typically between $500,000 and $1 million — however they like. That’s a big deal in the philanthropy world, where grantees frequently feel hamstrung by layers of bureaucratic requirements. In accepting her award this past April in Oxford, Molly Melching, whose group works to end the practice of female genital cutting in Africa, expressed her gratitude to Skoll personally by performing a traditional Senegalese dance, ambling over onstage to Skoll, who clapped and awkwardly swayed for a moment to her beat.

Skoll certainly realizes that he can use his money in a variety of interesting ways. Unable initially to find someone to manage his personal finances, he started his wealth-management firm, Capricorn. Today the firm is branching into eclectic investments such as lending to midsize health care companies. It’s also an investor in Tesla Motors (TSLA) — Skoll drives a fire-engine-red Tesla Roadster — and other companies that bill themselves as solutions to global warming. Though Skoll is Capricorn’s “anchor client,” says Stephen George, its chief investment officer, the firm has begun soliciting additional investors. One early taker is Al Gore. Ultimately, though, Skoll plans to give his money away. He’s signed Bill Gates and Warren Buffett’s pledge to give the majority of his wealth to philanthropy.

“I had a protective feeling about him initially because he was new in a town full of smarmy, ultrasmooth people,” says Robert Redford.

Skoll also invests in the loftiest of projects, one with no shot at a short-term payback: world peace. He’s a financial backer, along with business and entertainment luminaries like Richard Branson and Peter Gabriel, of The Elders, a group of retired politicians including Mandela, Desmond Tutu, and Jimmy Carter, who jet around the world (sometimes on Skoll’s jet) promoting nonviolence. Skoll feels great affection for these former dignitaries, who have been known to make waves for their rebukes of government officials in hot spots such as Israel and Sri Lanka. The feeling is mutual. Tutu, the retired Episcopal archbishop of South Africa and Nobel laureate, calls Skoll a “wonderful young man” who is “earnest without being boring about it.”

Even as Skoll is doing his part to improve the world, his friends worry that his intensity is taking a toll on his personal life. “There’s a piece of me in my heart that wants to make sure he’s pursuing his own personal ambitions,” says old pal Omidyar, who also spends much of his time on philanthropy.

For his part, Skoll acknowledges a void in his life. He suffers from chronic back pain, the result of a birth defect, and has endured five surgeries that have failed to correct the problem. “I’ve had these episodes where the back just flares up, and all of a sudden I can’t do stuff for a period of days, weeks, or months. It makes it difficult to really forward-plan commitments.” Unbidden, he continues, “Candidly, one of the things that has been on my mind is, I’m 45 years old, I’d like to have kids and a family.”

To be clear, Skoll is no hermit. He recently joined the new Soho House club in West Hollywood, where he’s on backslapping terms with the celebrities and industry insiders who frolic there. He’s an accomplished guitar player who enjoys jamming into the wee hours. Lately he’s been thinking about returning to his childhood ambition of storytelling. Skoll confesses that he has seriously considered taking a break from overseeing his social-action empire and taking classes in screenwriting. “I’d love to find the time to not be sitting in an office in L.A., but rather to be working on my own stuff, hands-on,” he says almost wistfully. There’s no question any Skoll-penned screenplay would get green-lighted. But for now there’s a planet to save.

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