One sunny morning in March, Tiffany Shlain sat down at Farley’s on Potrero Hill to talk with Professor Gernot Grabher, a researcher from the University of Bonn who studies how people use social contacts for professional advancement. Shlain has long blond hair and a Cadillac-size smile and the ability to converse with just about anyone on the planet on just about any topic. She founded the Webby Awards (the Internet’s version of the Oscars) when she was 26, has had two films shown at Sundance, and commands a hefty fee for delivering lectures about technology at places like Stanford and IBM. But none of that quite explains her knack for knowing people, for knowing people who know people, and for introducing people who should know each other.

In November she was in New York celebrating the 10th anniversary of the Webbys at an HBO-sponsored confab along with the New Yorker’s James Surowiecki and the Daily Show’s Rob Corddry. On New Year’s Eve she was at dinner at Chez Panisse, clinking glasses with movie producer Tom Luddy, Academy of Motion Picture Arts and Sciences President Sid Ganis, Esprit founder Susie Tompkins Buell, and UC Berkeley journalism school dean Orville Schell. In January she was at Sundance for the screening of her new film, The Tribe, where she sipped hot cocoa with people like Wim Wenders, Robert Redford, Todd Haynes, and the Beastie Boys. “I know a lot of people who make things happen,” she explained to me recently when I asked her about her celebrity contacts. “I’m attracted to that.”

Grabher had been interviewing well-connected people for weeks, asking questions like, “Would you include someone in your database without meeting the person? Do you keep people in your network who don’t reciprocate the favors you do for them?” These queries yielded straightforward answers when talking to Silicon Valley executives, who discussed their social contacts the same way they talked about their investments. But Shlain doesn’t think that way. When she talks about social networks, she’s thinking about chemistry, dynamics, movement, circuitry—the frisson created when an electrical impulse has a pathway to travel along. Trying to interview Shlain about the mechanics of her network is like trying to interview Jimi Hendrix about what makes a good guitar string. Within minutes of sitting down, she’s riffing on terrestrial metaphors for virtual interactions, the appeal of the tactile, Wikipedia, the spread of online niche communities, the “network effect” (in which a service’s value increases with the number of people who use it), graduated levels of online intimacy, the Internet as a conduit for film distribution, and the Pew Internet and American Life Project, which has found that the Internet has strengthened, rather than weakened, people’s social ties.

“This is what I really think,” she told Grabher, who was looking as if he had gotten much more than he had bargained for out of the interview already. “We’re connected in the womb by the umbilical cord to our mother. Then we come out and the cord gets cut, and we spend the rest of our lives trying to connect to something bigger than ourselves. I’m most fascinated by humans’ desire to connect. It gives me faith in humanity.” At the end of the interview, she reached out to shake his hand, examined his business card, and asked him to send her some of his research and a bio. “You would be a great judge for the Webbys,” she told him. Just like that, he had become part of her network.

Shlain burst onto the San Francisco scene in the late ’90s, as dot-com delirium began to grip the city, and her ambition, glitz, and affinity for center stage were sometimes at odds with the city’s laid-back sense of propriety. She was a glamour girl among techno-geeks, over the top in a town that favored understatement. In 2001, SF Gate columnist Mark Morford crystallized some of the sentiment against her when he wrote that a chief ingredient of the Webbys was “massive Tiffany Shlain divahood ego inflation.”

People still don’t know what to make of Shlain’s audacity. A common refrain has been, “How does she have the nerve?” If you’re someone who works in technology, film, or the performing arts, and you haven’t gotten the attention Shlain has despite your obvious talent, the question might be laced with bitterness. If you’re someone who works in those fields and Shlain has introduced you to someone who might be helpful
to you or invited you to collaborate with her, you may genuinely want an answer. But to be audacious is simply Shlain’s nature. A few years ago, when a reporter asked her how she had managed to persuade so many celebrities to get involved in the Webbys, she answered, “I just called them up and asked.” For years, she kept a Goethe quote hanging on a wall in her office: “Whatever you can do or dream you can, begin it. Boldness has genius, power and magic in it.”

But to dismiss Shlain as a publicity hound, a dilettante, or a professional schmoozer is to misunderstand her particular genius. Some people have a talent for making things, and some have a talent for connecting things. Shlain’s passion is for linkages—between people, between ideas, between images, disciplines, and technologies. Hence the “Breakfast at Tiffany’s” e-mails she sends out regularly to people ranging from Al Gore to her brother Jordan, encouraging them to check out books, performances, lectures, and causes she finds worthwhile and updating them on the status of her own projects. And hence her unusually eclectic aesthetic. She is constantly ripping things out of magazines that she might want to use someday—articles, graphics, quotes, colors. “She is really a collage artist or a remix artist,” says Maya Draisin, Shlain’s best friend and collaborator. “She’s always collecting ideas, images, and icons and then putting them together in interesting, unexpected ways.” (Even Morford is now an admirer.)

Take The Tribe, for instance, Shlain’s film about Jewish identity that had its San Francisco premiere in December. Using Barbie as the central image in her movie is
a good example of Shlain’s collagelike approach to art. Barbie’s creator, Ruth Handler, was a Jew who based her creation on the Lilli doll, a racy postwar plaything for German men. (Mattel, Barbie’s maker, denies this version, claiming Handler was inspired to make Barbie by watching her daughter play with paper dolls.) In The Tribe, Shlain uses the irony of a Jewish woman modeling an American icon on an Aryan ideal as a metaphor for the sticky question of assimilation and identity—and as a way to make the topic of Jewish identity more fun. “Because,” Shlain says, “it’s not like a lot of people would say, ‘Oh, a film about Jewish identity. Let’s go!’ They’d run away.”

The Tribe was born out of Shlain’s own perplexity about what it means to be Jewish, particularly if you’re young, hip, and not particularly religious. As a blond, blue-eyed teenager growing up in Mill Valley, she always felt like being Jewish was something she could choose to be or not. But it wasn’t until after she married artist and Cal robotics professor Ken Goldberg, another light-haired, blue-eyed Jew, that Shlain began trying to attach words and images to her questions about Jewish identity. The subject played to her strength: finding a hot topic and a sexy way to talk about it.

“She’s kind of redefining the genre of shorts,” says San Francisco filmmaker Lynn Hershman Leeson. “It’s subversive in that they’re entertaining and beautiful, so you don’t get hit over the head with the message, but it eventually seeps in.”

The Tribe’s premiere in December at the Herbst Theatre was everything a Tiffany Shlain production should be. The sky was raked by spotlights, and a film crew from New York stood in the lobby documenting the nearly sold-out crowd. The audience contained hipsters in hoodies and graybeards in tweed, activists, society matrons, and poets—some wearing yarmulkes, some wearing sequins, and one wearing a sequined yarmulke. San Francisco Chronicle columnist Leah Garchik was there, as was Gavin Newsom’s chief of staff, Mike Farrah; former Sierra Club president Adam Werbach; and Roselyne Swig, the film’s major funder. A Jewish drag queen named Hadassah Gross emceed, and there was a panel discussion afterwards, followed by an audience participation exercise and an after-party at the funky-chic Rickshaw Stop nearby. It was, as one San Francisco blogger noted afterwards, a lot of hoopla for an 18-minute movie. But when Shlain gets excited about some­thing, hoopla inevitably follows. (When she was little, her family referred to her as “Miss Enthusi-oozy-asm.”)

The Tribe layers actor and screenwriter Peter Coyote’s sly narration over found footage, slam poetry, and Gil Gershoni’s witty dioramas of Barbie and Ken in various Jewish settings (at synagogue, being led out of Egypt, getting a nose job), all in the service of posing a question: What does it mean to be Jewish? The film doesn’t provide any answers, nor is it meant to. Its purpose is to provide a framework for that most Jewish of pastimes: talking. “It was important to me that it be a short film, because I wanted to have enough time to have the discussion,” Shlain explains. “If the film is 15 minutes, then discussion is 45.” It was a big hit at Sundance, where it had six sold-out official screenings and many unofficial ones in the house Shlain rented for herself and the crew. It has since gone on to the Tribeca, Ann Arbor, and Nashville film festivals, and it won the Director’s Choice award at the Black Maria Film and Video Festival, which travels to some 70 venues around the country.

But Shlain doesn’t want it limited to the festival circuit. She is distributing it online (www.tribethefilm.com) along with the Unorthodox, Unauthorized discussion kit containing a “Guide from the Perplexed,” which amplifies some of the film’s ideas, and conversation cards printed with trigger words like circumcision, Israel, and Christmas. Orders and invitations have streamed in from many sources, including synagogues, museums, universities, and even a group of Jewish midshipmen at the U.S. Naval Academy. Having nearly sold out of the first 2,000 copies, Shlain recently ordered a second printing.

And all of this started from one particularly bold, Shlain-like move: how many young filmmakers would have the gumption to approach philanthropist Roselyne “Cissy” Swig, widow of hotelier Richard Swig and an icon of genteel San Francisco, and ask her to bankroll a film that would feature animated Barbie dance sequences and a poem called “Hebrew Mamita”?

“She’s fascinating because she embodies fearlessness,” says San Francisco Chronicle columnist Leah Garchik. “I speak from the perspective of someone who works for
a weekly wage. When I look at people like Tiffany who are fascinated by something and pursue it without waiting for someone to say OK or give them a grant, I’m kind of awestruck.”

Shlain’s fearlessness was the key ingredient 10 years ago, when Greg Mason, publisher of The Web magazine, asked the 26-year-old freelance Web designer if she would be interested in producing an awards show for websites. How Mason knew that Shlain would be an unbeatable proselytizer for a medium that had heretofore been the province of the pocket-protector crowd is a mystery. But he clearly was on to something. The dot-com boom has come and gone, but the Webbys have survived and prospered. The 10th anniversary show will take place June 12 at Cipriani Wall Street in New York with Rob Corddry hosting. The more than 500 judges include Larry Ellison, Beck, Arianna Huffington, and Ira Glass.

Shlain had been thinking about the connective potential of computers since high school. In 1988, she and an Iranian friend were electrified by the discovery that they could use their home computers to contact their high school library. The two wrote a proposal suggesting that students in different countries use their computers to communicate with each other directly, transcending the tension created by the Cold War and the hostage crisis. The pair was a bit ahead of the technological curve, but the proposal did earn Shlain a trip to the Soviet Union as a student ambassador.

“We are students who believe the world will benefit from this unbiased form of communication,” she told a reporter, already sounding like the Internet cheerleader she would end up becoming.

The youngest of three children, Shlain grew up in Mill Valley with parents who valued intellectual achievement. “Respect for the brain was big in my family,” Shlain says, but so was innovation. There was a geodesic dome in the backyard, and when the family couldn’t find a suitable synagogue in south Marin, they founded a “synagogue without walls” on Mt. Tamalpais.

Tiffany was not the only one who lived by Goethe’s maxim. Her mother, Carole Lewis Jaffe, went back to school to get her master’s and then PhD in clinical psychology when Shlain was 7, a move that Shlain often cites as one of her inspirations. Her father, Leonard Shlain, is chair of laparoscopic surgery at the California Pacific Medical Center in San Francisco. He once brought a bucket containing a human brain into Tiffany’s fourth-grade classroom so he could show the kids the difference between the right and left hemispheres. In the late ’80s he got interested in the relationship between art and physics, studied up on both, and wrote an influential book called Art and Physics—then went on to write two similarly cross-disciplinary best-sellers. Tiffany’s brother, Jordan, is a San Francisco doctor who founded San Francisco On Call, a group of doctors who perform house calls. Her sister, Kimberly, is a Los Angeles artist and Web designer married to the actor and director Albert Brooks.

Watching and discussing movies over Chinese food was a Sunday night tradition in the Shlain family, and Shlain majored in film theory at UC Berkeley and won an Eisner Award, the campus’s top artistic prize, for her student work. After graduation, she began working on a feature about a sculptor with a creative block, but kept running out of money. In the meantime, she supported herself by doing various kinds of tech jobs, first by making CD-ROMs and then, when the Internet was still in its infancy, by designing websites. It was while she was working on a CD-ROM for Sting that she saw her first website, a bulletin board for Sting fans. “I thought, ‘This is going to change the world,’” she recalls, and her conviction has never wavered. Throughout the hyperbolic boom times and the despondent bust, Shlain has remained convinced that the Internet was notable not for producing instant millionaires or instant paupers, but for changing the way people live, work, and think.

“I love the nonlinearness of the work style that we have been able to create with the Internet,” she says. “When I work, I have 15 files open. The phone rings, and that makes me think of something, then I do some more research and think of something else. I used to feel like ‘I’m all over the place,’ but now I think that we’ve finally created a work environment that mirrors our stream of consciousness.”

Armed with her belief that the Internet would turn out to be as revolutionary an invention as the camera, the airplane, and the steam engine, Shlain took the trademarked name “Webbys” and with no budget, set about producing the first Webby event in 1997 at Bimbo’s 365 Club. Eleven companies donated money or goods, and Cintra Wilson agreed to emcee. To everyone’s surprise, the show was one of the most sought-after tickets in town. More than 700 people attended.

The Web magazine folded soon afterward, but the Webbys lived on, sponsored in part by IDG, the magazine’s parent company. But it was always Shlain’s production. From the beginning she concocted a uniquely San Francisco potion of enthusiasm and outrageousness, spectacle and satire. Because she found the acceptance speeches at the Oscars deadly dull, Webby winners were told to limit their speeches to five words or less, a requirement that has spawned a genre of haiku-like one-liners. Her imprint was on every aspect of the event, from the experimental films she made and showed during the ceremony, to the guest appearance by her 94-year-old grandmother in 1999. She even previewed—and sometimes disallowed—the emcee’s jokes and choice of attire.

Some people groused about Shlain’s ubiquitousness at the Webbys, but Heather Gold, a writer and comedian who is now one of the Webby judges, insists she earned the right. “She put the whole frickin’ event together. Did she self-promote harder than a lot of guys did? I don’t think so. It was a self-promoting era.”

As the dot-com bubble inflated, so did the Webby Awards, becoming more glitzy and spectacular with every passing year. In 1998, Shlain decided to create a separate organization to handle the judging and asked Draisin, whom she knew from her CD-ROM days, to help. Together, the two founded the International Academy of Digital Arts and Sciences, and—with characteristic moxie—invited celebrities like David Bowie, Matt Groening, Tina Brown, and Deepak Chopra to join. By now, the Webbys were being held at the city’s swankiest locales, with sponsors like Adobe, Hewlett-Packard, and Intel. In 2000, as dot-com mania infected the entire city, the theatrical foofaraw included aerialists dangling from the roof of the Masonic Auditorium and actors dressed as 1940s paparazzi fawning over the guests.

“It epitomized the fun and folly of the whole era,” says Gary Kamiya, executive editor of the online magazine Salon, which won a number of Webbys during the boom. “There was an attempt to make a self-fulfilling prophecy. If you give out awards and say the Internet is an important medium, it’ll become one. And in that respect the Webbys have fulfilled their promise.”

And the Webbys have somehow survived long enough to say, “I told you so.” In 2003 and 2004, as San Fran­cisco woke from the fever dream that had been the dot-com boom and Shlain found herself preoccupied with motherhood (her daughter, Odessa, is now 3), there was no awards show at all; the prizes were simply announced online. But the Webbys were only hibernating. Last year, the winners in 65 categories were chosen from among 4,400 entries, more than twice the number of any year in the show’s history. No one has to explain why the Web is important anymore—most of us can’t imagine functioning without it. In 1995 there were 16 million people online; now there are more than a billion.

While Shlain is still the Webbys’ public face, she no longer works on the day-to-day operations. “I used to spend all my creative energy on this one evening a year,” she says. “I would rather focus that kind of creative energy onto film, which has a longer life.”

On the desk where she works, in a corner of the bedroom of her Potrero Hill condo, Shlain keeps a glass paperweight that contains a dandelion head inside, a gift from Goldberg. It is a compelling image for her, one that seems to encapsulate everything she loves about the Internet, and everything she wants to accomplish with her films—a cluster of seeds that can be dispersed in a thousand directions by a single breath.

In fact, Seed is the working title for Shlain’s next project, a feature-length film that will explore issues of reproduction, technology, and the environment in what has become her trademark collage/comedic style. She’s already begun talking to funders and started hashing out ideas with collaborators Goldberg, Carlton Evans, and Maya Draisin. Between planning the Webbys, promoting The Tribe, lecturing, raising Odessa, and repackaging her reproductive-rights film—Life, Liberty and the Pursuit of Happiness—as a discussion kit for the 2008 election, you might think that Shlain had enough on her plate already. But that would be underestimating how seriously she takes Goethe’s exhortation. “She has so much energy and drive and optimism,” says Draisin. “Anything she wants to make happen, will happen. And happen at the highest level.”