From the Valley of the Geeks Comes the Digital Diva

Decked out in an Issey Miyake metallic top, leather skirt, red snakeskin boots and matching red Nokia phone, Tiffany Shlain charged into San Francisco’s Museum of Modern Art recently for an interview like she owned the joint.

Dubbed “the Digital Diva” by San Francisco Mayor Willie Brown, the 30-year-old Shlain has brought glitz and glamour to the Valley of the Geeks by creating the only awards show for Internet sites that matters--the Webbys. To be sure, there were others before (and still are), but nothing has caught on like the Webbys. And none was ever quite so entertaining: Webbys acceptance speeches are limited to five words. (The rule was violated last year when Salon.com founder David Talbot proclaimed “I did not have sex with that woman, Miss Shlain.”)

In the four years since she founded the Webbys, Shlain has packaged herself as an authority on the convergence of high-tech and pop culture. She has been written about in newspapers and magazines, is often asked to comment about Web culture on television and lectures to groups in the U.S. and internationally.

Broadcast only on the Web, they may not be a household name like the Oscars, but they’ve certainly arrived by some measures of popular culture: Not only have the Webbys been the subject of an Absolut vodka ad (“Absolut Webby”), they’ve also been an answer on the ABC quiz show “Who Wants to be a Millionaire.”

“Tiffany has a vision in her head about making the Webbys something with cultural significance and placing the Internet in the fabric of our culture,” said Shlain’s husband, Ken Goldberg, 38, an engineering professor at UC Berkeley who has gained some renown as a digital artist.

Shlain started her career as an aspiring filmmaker but was turned off by Hollywood’s rough and tumble style: “They just build people up to tear them down,” she said. “It’s like no other place in the world, except maybe London with its tabloids.”

It’s possible, though, that Shlain has figured out that an easier way to conquer Hollywood is to make herself so appealing that the town won’t be able to resist her. Just last month, she was in L.A. meeting with TV executives interested in airing the Webbys.

Getting the Webbys on TV also resonates with her democratic instincts about how the Internet will change the world: “Hollywood has been America’s royalty for so long,” Shlain said. “In the distribution mechanisms, it was a select group of people who decided what was playing on your radio, what was showing on your movie theater and which people are made into celebrities. The world deserves a redistribution of attention, and I’m happy to help.”

But she was savvy enough to know the Webbys needed big names to make news, so she persuaded more than 200 of them to join the International Academy of Digital Arts and Sciences, the entity she created as the Webby voting body.

“We didn’t just pick flash-in-the-pans,” Shlain said. “They are heroes in our culture in each of their fields.”

BCBG fashion designer Max Azria joined the academy because of the Webbys’ “new and modern approach.” Talk magazine’s Tina Brown found Shlain persuasive because she has “tremendous flair.” Her awards show nominating judges include director Francis Ford Coppola, pop singers David Bowie and Courtney Love, ACLU President Nadine Strossen and “The Simpsons” creator Matt Groening.

That she was able to secure such luminaries attests to her confidence, which she is not afraid to flaunt. When asked how she persuaded them to sign on, she replied that “in typical Tiffany Shlain style, I just called them up and asked.”

Shlain is smart, pretty and poised for success. . . . Naturally, she has her detractors.

She’s come in for mild criticism from some who say that the Webbys, which she writes, directs and produces, are “too much Tiffany.” (They point to a bit in last year’s show where she wheeled her 95-year-old grandmother, Frances Shlain, on stage to sing a ditty about the Internet.)

“The show is my vision,” she responded. “That is what a director does.”

This year’s Webbys were the biggest ever, with 135 Web sites competing in 27 categories. The show was covered by nearly every major TV network, newspaper and news magazine in the U.S. and a few international media outlets, too. And now that the awards have grown, Shlain knows the stakes are higher for her as well. Will she be able to stay true to the funky roots of the show if it ends up on national TV?

“That’s the creative challenge with anything that becomes popular,” she said.

Shuns Silicon Valley for Trendier SoMa

Shlain works not in Silicon Valley, but in a neighborhood called South Park in San Francisco’s south of Market Street district, or SoMa. She is right at home in the area, which has a college-campus feel, with sidewalk cafes, boutiques and shiny new VW Beetles. A nerve center for creative Internet types, it is where Wired magazine, streaming music and video site WiredPlanet.com and online college bookstore BigWords.com make their homes.

The youngest of three siblings, Shlain was born and raised on the other side of the Golden Gate Bridge, in Mill Valley, by parents who divorced when she was 10. Her father, Leonard Shlain, is chief of laparoscopic surgery at California Pacific Medical Center in San Francisco. Her mother, Carole Lewis, is a psychologist in private practice in the city.

“Watching my parents love what they do, it wasn’t an option,” Shlain said. “I had to love what I did, too.”

Her parents deeply influenced her appreciation for aesthetics.

“My mom has great style,” Shlain said. “She sewed all our clothes,” including a favorite patchwork skirt made from old blue jeans. “Getting dressed has always been a creative exercise for me.”

In fact, one of Shlain’s first initiatives as president of Mill Valley Middle School was to appeal a policy prohibiting hats in class photos. “I took it all the way to the principal,” she said. “And I won.”

Leonard Shlain, who is also a writer, helped culture his daughter’s dual loves of art and technology. In a 1991 book, “Art & Physics: Parallel Visions in Space, Time & Light,” he theorized that great works of art have foreshadowed the discoveries of physicists. (The visual fragments of the Cubists, for example, portended Einstein’s theories about relativity.)

“Most surgeons don’t write books,” he said. “I raised the bar for my children. All three have wanted to emulate and achieve.” (Shlain’s sister, Kimberly Brooks, 34, is chairwoman of ShoppingtheWorld.com and her brother, Jordan Shlain, 33, is a physician and the CEO of MedicinePlanet.com.)

He also likes to take credit for helping Shlain find her husband, because they met at one of his lectures in San Francisco.

“We basically went out to dinner that first night with a whole bunch of people and didn’t even notice them,” said Goldberg, whose artwork was exhibited at the Whitney Museum of American Art’s 2000 Biennial show in New York last spring. (His most well-known installation, TeleGarden, lets Internet users direct a robot to plant seeds in a garden at a museum in Austria.)

They were married two years ago on the summer solstice (“Since it is the longest day of the year, we could extend the reception,” he joked). The couple recently bought a home on the once-industrial, now gentrifying Potrero Hill that they’ve filled with art and customized with robotics. Because Shlain likes to wake up to sunlight, for example, Goldberg rigged the shades to go up when the alarm clock goes off.

Shlain said she’s been fascinated by technology since she flipped on a light switch as a toddler and became a self-proclaimed “evangelist of the Internet” as soon as she accessed her local library from her home computer at 14.

While at Redwood High School, Shlain and a friend founded an after-school club called UNITAS, United Nations in Telecommunications and Software. They wanted to set up a way for students in different countries to communicate by computer. At 17, she traveled to the Soviet Union through the People to People Student Ambassador Program to talk up her idea.

Already speaking in sound bites in 1988, she told a reporter back then: “We aren’t businessmen and we aren’t politicians--we are students who believe the world will benefit from this unbiased form of communication.”

At 19, while studying film at UC Berkeley, she started a business making customized computer covers in whimsical prints and called them Apple Skins.

“People were always so intimidated by technology,” she said. “I wanted to figure out a way for them not to be.”

She considered dropping out to build the business, but her brother, who was on a World Teach program in Africa at the time, persuaded her not to leave.

“He was teaching kids in Africa who would have loved to be in my place,” Shlain said.

In 1992, she graduated as a valedictorian of her class and began writing and directing what she hoped would be her first feature-length film, about a sculptor’s struggle to stay true to his artistic vision.

The trailer for the unfinished feature, “Zoli’s Brain,” is shot in dramatic black-and-white style, inspired by the great Italian director Federico Fellini, one of her creative heroes. (She commemorates her admiration each year at the Burning Man Festival in the Nevada desert, by hosting a Fellini Cocktail Party at her Winnebago, complete with champagne and caviar.)

To fund “Zoli’s Brain,” Shlain worked intermittently in high-tech jobs, developing a CD-ROM with pop singer Sting in London in 1994, designing Web sites for Industrial Light and Magic in Hong Kong in 1995. She never asked her family for help.

“My father definitely taught us the value of a dollar,” she said. “We always worked.”

In 1995, Shlain decided she was sick of being a struggling filmmaker and abandoned the project.

“My whole life I had succeeded at everything. I thought it was the worst thing in the world when I was 24 to have not finished a feature film,” Shlain said. “But I learned so much more about myself. You can’t just keep doing something because you don’t want to be a quitter.”

Then, in 1996, she was offered the opportunity that would change her path. Greg Mason, publisher of a magazine called the Web, owned the word “Webby.” Impressed by her background, he asked Shlain, who was designing a Web site for him, to produce an Internet awards show.

“It was a blank canvas,” said Shlain. “I had a vision of how huge it could be.”

Show Goes on Before Magazine Folded

The first Webby Awards took place in 1996 at Bimbo’s Supper Club in San Francisco. Mason’s magazine folded soon thereafter. But the Webbys lived on under the magazine’s parent company, Boston-based International Data Group, publisher of the Books for Dummies series and Cliffs Notes. Shlain is now CEO of Webby Awards Inc., a division of IDG. She is also the creative director and executive producer of the show.

“Tiffany has not only created an event, she’s sold it to others, which is a great endorsement of her skills as an impresario,” said IDG President and CEO Kelly Conlin. “The Webbys have a great future.”

Two years ago, New York Mayor Rudolph Giuliani offered to provide a new home for the Webbys, and after Shlain declined, the press in both cities had a field day.

“I say no to a lot of things,” she said. “Mayor Brown has attended the Webbys since Year One. But it would be incorrect to say the fact that Giuliani wanted the Webbys didn’t increase the city’s participation,” said Shlain. “It’s not like we get special treatment. It’s just important to the city.”

So important, apparently, that this year’s Webbys, on May 11 at the Masonic Auditorium, featured a post-party in Nob Hill’s Huntington Park, the first time in memory the city had allowed such a thing.

“It was unique event,” said Sandy Lee of the city’s Recreation and Parks Department, “the first and maybe the only that will ever be held there.”

The Webbys may be in the off-season now, but Shlain isn’t slowing down. She wants to write a book comparing the Internet revolution to the Renaissance and spend more time in her art studio. There are speeches to give and awards to receive (she nabbed a Shining Star Award from the American Women in Radio and Television last month).

And despite the lesson she learned about “Zoli’s Brain,” Shlain still hopes to finish the film, maybe even release it on the Web.

“I now know that there is a way to be true to one’s vision, however alternative that may be, and still reach a large audience,” Shlain said. “I have experienced it with the Webby Awards.”