Skoll—a billionaire by way of eBay, where he was the first president—wanted to start a film-production company that would foster social change. Movies seemed an opportune way to draw attention to the world's problems and inspire viewers to address them. But Skoll, MBA '95, was met by a nearly united front of agents, lawyers, writers and actors who advised him over endives not to set fire to his money. There was no surer way to shrink his billions to millions, they told him, than to presume he could avoid the fate of other Hollywood outsiders whose "carcasses" were piled up near the studios' gates.
That was 22 Academy Award nominations ago for the company Skoll created, Participant Media. It was before Skoll and others persuaded Al Gore that they could make his slide show into An Inconvenient Truth. Before Skoll produced documentaries such as The Cove, spotlighting dolphin hunting in Japan, and Waiting for "Superman," a searing look at public education. Before a string of Hollywood dramas crackled with performances by George Clooney, Matt Damon, Tom Hanks, Julia Roberts and Charlize Theron. Before The Help flexed new box-office muscle by being the only one of the nine 2011 best-picture nominees to gross more than $100 million in the United States.
Behind this success is the only contrarian trait Skoll, 47, makes obvious—inexhaustible hopefulness. It's a wellspring of tenacity that's rooted, says friend and ally Sally Osberg, in an unyielding "belief in the power of human beings to create the communities and the world they want." Skoll's unassuming manner seems otherwise devoid of any insistent temperament; he's constantly described as the consummate listener and consensus builder. It's his fiercest friends and admirers who say that in a room of movers and shakers, he's the wallpaper. Employees exult about how empowered they feel. Skoll's only absolute mandate, his only intractable passion, is for everyone to think big.
That applies to his media impact, which he intends to extend to cable or satellite television, and his not-for-profit ventures, which feature goals so planetary that they include an effort to confront nuclear proliferation. The core enterprise is the Skoll Foundation, which since 1999 has awarded some $300 million to an international brigade of social entrepreneurs and organizations. There's also an investment firm dedicated to ethical money management and TakePart.com, a Participant Media offshoot that works to convert people's concern about issues into individual and collective action. Finally, there's the Skoll Global Threats Fund, established three years ago to joust with haunting disaster scenarios: nuclear catastrophe, pandemics, water shortages, climate change and conflict in the Middle East.
"Sisyphus gets a bad rap," says Larry Brilliant, who oversees the mountain-moving initiatives of the threats fund. Brilliant, a physician and public health expert who helped drive the worldwide smallpox eradication program in the 1970s, is undeterred by steeply uphill challenges. The former head of Google's charitable operations, Brilliant relates to the idea that quixotic goals can be rendered manageable. But the scope of Skoll's vision stunned him. "Nobody ever said to me, here's a chance to tilt at the toughest windmills in the world."
"I feel like the issues of the world are getting worse," Skoll says. "I think we're living in increasingly perilous times. I do think there are small wins along the way, and that's great. We need some bigger wins. And as far as my organizations go, I'm very proud of the work they're all doing. But this is a world of big issues that we're tackling and sometimes we just may not be enough.
"But we're going to try."
When Skoll left Stanford with his MBA, he enlisted in the newspaper business, which was soon to be pummeled by the digital age. He took an information management job with the now-defunct Knight Ridder company, in part because he thought newspapers like its San Jose Mercury News would be the logical platform for monetizing electronic content and putting classified ads online.
For a while, he resisted an overture from Pierre Omidyar, an entrepreneur he had met through mutual friends in Silicon Valley, to help construct an online auction firm. But after too many dead-end discussions about the Internet at Knight Ridder, Skoll recalls, "I finally said to Pierre, 'I think you're on to something. Let's go do this.' " Skoll wrote eBay's business plan using a typical five-year projection. "We actually hit the five-year numbers in the plan by our second year," he says.
"Jeff and I worked all the time," Omidyar recalled in an email. "We were both heads down and extremely focused. We rarely took breaks. We had a small office, sitting side by side, and just worked constantly. The business was growing at such an exponential rate that most days, we were just trying to survive the ride."
The company went public in 1998, making Skoll his fortune. Forbes—which last year calculated that Skoll was one of only 20 people who have donated $1 billion or more during a lifetime—puts his net worth at $2.7 billion.
As surprising as the notion may seem, eBay amounted to a test bed for Skoll's approach to global betterment. The firm's success didn't hinge only on collector mania for Pez dispensers or baseball cards. It depended on a basic sense of trust between buyers and sellers—a fundamental faith in people and their behavior as a community. "We had this premise," Skoll says, "that people are basically good, and if you give good people the opportunity to do good things with each other, they will."
Garth Saloner, dean of Stanford's Graduate School of Business, singles out Skoll for "an understanding of the social fabric," be it at eBay or in humanitarian entrepreneurship. "That's who Jeff really is."
Skoll started his namesake foundation while at eBay with the help of Community Foundation Silicon Valley. But not long after, he had to confront the kind of event that turns life upside down and leaves it there. In a skiing accident, he injured his back badly enough that it became the primary reason he left eBay. "In 2000, my last full year at eBay, I was in agony," he says. "I couldn't sit. I would take meetings lying on a conference table."
Doctors suggested surgery, but Skoll concluded an operation was unlikely to resolve the problem. While he explored alternatives, he turned more attention to his foundation and created Capricorn Investment Group to ensure that his portfolio reflected his social principles. He hired Osberg, founding executive director of the Children's Discovery Museum of San Jose, to be the Skoll Foundation president, a role she remains in 11 years later. His back showed improvement with the help of injections from a doctor he now provides with research funding. His foundation grew steadily in international impact and reputation.
Participant Media's movie mojo and the fund that throws down against global catastrophes have an undeniable wow factor, but the Skoll Foundation is the bedrock. Osberg describes "a very special partnership" she has with Skoll, based on a relentless stamina for gigantic battles. Her job, she adds, is to keep that spirit "alive and on the edge."
The foundation intends to spur sweeping change; its funds support social entrepreneurs aimed like arrows at situations that seem particularly ripe for an "outsized impact." Initial multiyear operating grants range from $500,000 to $2 million, and the recipients come from all continents. Sakena Yacoobi, for example, runs the Afghan Institute of Learning, providing education to tens of thousands of women and children, as well as training teachers and community leaders. Mark Plotkin and Liliana Madrigal created the Amazon Conservation Team to partner with indigenous populations in preserving the rainforest; the work has included land-use mapping for more than 60 million acres. Andrew Youn established One Acre Fund to assist impoverished rural farmers in Kenya and Rwanda. More than 24,000 families have tripled their food production and doubled their profit per acre, and mortality rates for children from birth to 2 years old have plunged within the fund's areas of operation.
It's these types of initiatives, involving scores of individuals who are part innovator/part adventurer, that allow Skoll to savor measurable, replicable achievements. Closer to home, he points to Bill Strickland, who decided to pay forward the kind of life-altering mentorship a ceramics teacher had given him. The arts and vocational programs he established in a depressed section of Pittsburgh have become a model for educational outreach. "The same kids that were dropping out—the dropout rates in that neighborhood are 70 percent—that were going to Bill's after-school programs were graduating at 90 percent," Skoll notes.
Strickland also epitomizes Skoll's ideal that people should multiply their impact by making their activism an inspiration to others. Skoll's catchphrase goal is "to live in a sustainable world of peace and prosperity," and he thinks the best outcome depends on igniting an army of educated and motivated citizens.
Amid all the goals that are "really hard, and really hard to win," says Skoll, there's also a joyful sense of reward in the efforts of people like Strickland. "Some things are kind of easier to see and cheer on."
Skoll doesn't grant a lot of interviews. When he does open up, his childhood tends to be a central theme. He was born in Montreal, lived in Toronto from age 13 to 28 and was deeply influenced by the serious reading he did as a kid. "My family used to go camping in upstate New York," Skoll explains, "and there really wasn't a lot to do except read. There was a library nearby and every week we'd go out to the library and come back with a boxful of books."
By the time he entered his teens, Skoll already was thinking globally. "I could kind of see a lot of trends in the world were getting scary, that by the time I was older the world would have problems with population and resources and potentially deadly diseases and all kinds of things that kind of scared me. And I thought I'd like to get involved in these issues, make people aware of them, and as a kid I thought I would actually do it by being a writer. So that was my first goal."
With a little more thinking, he decided it would be pragmatic to build a more reliable career, then figure out what he might accomplish as an author. He had seen his father run a business and seen him survive a nasty bout with cancer, kindling Skoll's entrepreneurial spark and a deep appreciation for living with a strong sense of purpose.
It could sound like a tedious adolescence, but Skoll's precocious get-up-and-go generated lighter moments, too. He was living in Montreal when he tried selling Amway products door to door. There was a simmering question of whether the province of Quebec would separate from the rest of Canada. "I was living in a French-speaking part of Montreal," Skolls recalls, "and my French wasn't all that great." One of his products was a little electronic music keyboard that people would ask him to demonstrate. "The only song I knew how to play was O Canada," says Skoll, laughing. "I had a lot of doors slammed in my face. That's the onset of my entrepreneurial career right there."
He earned an undergraduate degree in electrical engineering at the University of Toronto and then got on a plane for the first time in his life to fly to London, where he started an improvisatory year of backpacking around the world. Back home, he developed two businesses, one in engineering consulting and the other renting computers.
The rental business "was called Micros on the Move," he says with a smile, "and it was very well named, because people kept stealing the computers." That and the relatively drab prospects of his consulting business prompted the realization that he could benefit from a business degree. That turned out to mean Stanford, followed by a cyber flea market dubbed eBay.
The Skoll Foundation is headquartered in Palo Alto, but Skoll, who became a U.S. citizen in 2007, lives in Beverly Hills to better shepherd the movie ventures. Not surprisingly, his travel is sometimes glamorous. January included the Sundance Film Festival, and early February found him among an array of scientists, executives and activists in Antarctica who were getting a first-hand look at melting ice. (The trip was organized by The Climate Reality Project, founded by Gore.)
But his typical schedule is substantially devoted to Participant Media. His credit on films is executive producer, a role that spans the conception, financing and marketing of a project. His ardent involvement in everything from the kickoff ideas for films and their script approval to their parallel social-action campaigns is especially fulfilling for him: This is the storytelling he dreamed about on those childhood camping trips.
Documentaries such as The Cove, a 2010 Oscar winner, have been forged in the same creative furnace as marquee attractions such as Contagion, last year's unnerving thriller about a pandemic. All get released with campaigns meant to engage the average filmgoer. The Cove was accompanied by a public-awareness push about seafood contaminated with mercury; Contagion was linked to community flu-tracking efforts. But the messages generally haven't drowned the pizzazz.
Actress Natalie Portman, who had a production deal with Participant a few years ago, says the company has crafted its identity with sharp artistic instincts. "The thing that they've done that's really smart is making movies that are still entertaining. No one wants to be taught at the movies."
Skoll has a variety of anecdotes that illustrate the ties among all his endeavors. Consider the Skoll Global Threats Fund, which has been underwriting causes such as the build-out of biosecure laboratories in the Middle East and North Africa. Fund overseer Brilliant also worked with a team of experts and writer Scott Z. Burns to create Contagion as a way of bringing attention to the public's vulnerability to pandemics. The result was a melding of scientific credibility and box office allure.
"We had an immense number of scientific advisers on that project, including a virologist named Ian Lipkin, who was on the set the whole production," says Skoll. When something didn't look right medically, "Lipkin would jump up, and he'd yell 'Cut!' and Steven Soderbergh, the director, would be like, 'What the hell?' "
Skoll ran Participant directly for more than three years before hiring Jim Berk, onetime chief executive of Hard Rock Café International, as CEO. Berk quickly became an apostle of "the film as the watering hole" for people on all sides of an issue. The goal is less to promote a given idea or viewpoint than to spotlight topics that instigate an ongoing civic conversation.
Like almost everything else Skoll is behind, the task has a utopian aura. For the road map that's needed, Participant prepared to-do lists and wish lists for every division and function of the company. The results were ambitious, even extravagant. Then Skoll reviewed all the plans and offered an admonishment: People weren't thinking big enough in some areas.
"How cool is this?" Berk asks. "But in a way, I'm pissed off. How am I going to make my own fortune if I'm so happy helping him spend his?"
Skoll, who has promised to give away the majority of his wealth as part of the Bill Gates-Warren Buffett philanthropy pledge, seems personally content. He's in the thick of combat with the menaces he always wanted to take on, and he notes how privileged he feels to have enough resources to carry the fight. He's a devoted pet owner—his Labradoodle is named Maya—and he sings and plays guitar in a band named Los Idiotos. There's some big stuff on the horizon, too.
"One of the regrets I've had over the years is getting older and not having had a family yet," he says. "Part of it has been just working too hard and not prioritizing enough. Part of it has been not necessarily finding the right person."
Now, he adds, "I'm happy to say I have a very lovely girlfriend now." And the family? "It's a huge priority for me."
Complacency is not in his DNA. His thoughtful mien disguises a profound vigilance. Despite the breadth of the foundation's accomplishments, Skoll began several years ago to dwell on its limitations. "I could see where we probably were not doing enough on the urgent issues of the day. And that's why I started the global threats fund. What I haven't ruled out is that there might be something else. And I don't know what that something else is.
"But I do know that if we can't make the changes in the world that I aspire to see, then there might be something else that I could be doing. I just don't know what it is yet."