When Flickr co-founder Caterina Fake was young, she didn’t want to be a technology start-up guru — she dreamed of becoming a writer and an artist.
Fake, a Filipino-American from Pittsburgh, pursued her dream to an elite liberal-arts college located in the heart of the Hudson Valley, earning a degree in English and dabbling in art. When she arrived in San Francisco in the 90s, the tech bubble was starting to swell, and she had the perfect opportunity to mix her artistic aspirations with burgeoning technology.
In 2004, Fake with her then-husband, Stewart Butterfield, created Flickr. A year later, they later sold the photo-sharing site to Yahoo. While she no longer works for Yahoo, and divorced Butterfield, she still keeps busy with start-ups and watching her first love, Flickr, continue to thrive.
Life Takes an Unusual Turn
Starting out, Fake held a wide variety of jobs, which fed her novel way of looking at technology. From 1991 to 1994, she worked at an investment bank, as a painter’s assistant, in a dive shop in Arkansas and even on a crew with “Seinfeld.” Her move west was bumpy, and settling in San Francisco marked a turnaround in her career. It wasn’t easy at first — her Vassar education didn’t include programming and coding, but her enthusiasm overcame these obstacles. As she told the New York Times, she taught herself how to program from scratch.
“I stayed at my sister’s house for several months and I started to teach myself HTML and then began building Web sites,” she said in the interview. Afterwards, things started clicking and Fake became an art director for Salon.com before moving on.
Blazing a Trail
Fake has a talent for marrying her passions with the times. After getting her English degree, she discovered working online best fit her artistic temperament. She got in early on blogging, and her website Caterina.net pioneered an online following. In fact, that’s how she met Butterfield, an early fan with strong computing skills of his own.
Their relationship flourished, and on a ski trip in British Columbia, they discussed co-creating a website. After Fake moved to Vancouver in 2001, she and Butterfield started Ludicorp with the goal of launching a multiplayer contest, “Game Neverending.” The game never took off, but Ludicorp’s side project — a photo-sharing option for gamers — became a hit. Switching gears, they shut down Game Neverending within months, and concentrated on the photo site, which they named Flickr.
“Had we sat down and said, ‘Let’s start a photo application,’ we would have failed,” Fake told USA Today. “We would have done all this research and done all the wrong things.”
Flickr Is Born
Fake and Butterfield saw what others hadn’t: people want to share photos. In 2004, the idea at the heart of Flickr was born, and their timing couldn’t have been more perfect. Prices of digital cameras plummeted, and people subscribed to broadband in droves, making uploading large photo files quicker and easier. And though they struggled for those few months, Yahoo called and scooped up Ludicorp for $35 million.
With Yahoo and Back Again
Shortly after the buyout, Fake took a job running Yahoo’s Technology Development Group, known for its Hack Yahoo program. After a successful run, in 2008, she resigned from Yahoo to strike out on her own.
“I treated it like a university experience,” she told the New York Times. ” I jumped into search, but it was soon pretty clear whatever replaces search was going to be a social experience.”
Armed with early success and her self-described Yahoo education, she went on to co-found Hunch.com, a site that built a “taste graph” of Internet activity. Hunch proved popular, reaching 1.2 million visitors a month, and selling to eBay for $80 million in 2011.
A seasoned businesswoman, Fake moved on to explore other interests, launching Findery, location-based storytelling site, in February.
Findery — the Latest Challenge
Findery shows how some ideas that didn’t work can re-emerge as technology advances. The site, which lets you pin and share personal notes of places, works like a communal scrapbook. The idea has been evolving since 1999, Fake told Inc. Magazine.
“One misconception is that start-ups start with a Eureka moment when the entrepreneur is sitting in the bathtub,” she told Inc. Magazine. “It doesn’t happen that way.”
In fact, she didn’t realize the idea had been germinating until her ex-husband called to congratulate her on the project. “He actually reminded me of a conversation we had in ’99 about how cool it would be to be able to leave notes in places like doorways and street corners and various places around the world.”
Back then, leaving electronic notes in random places wasn’t possible, because people didn’t have smartphones or GPS. The site, run by a small team operating out of San Francisco, is gaining steam and visitors are discovering new places where others have been.
“Someone at LinkedIn did this wonderful set of notes of all the locations of all LinkedIn’s offices. Subsequently there was a little office with five people here, then a bigger office with 20 people, there,” Fake told Inc. Magazine. “That’s what I love about it. There are infinite ways people could use it.”
Starting Over, Yet Again
Findery is Fake’s third major start-up, and of course, as her fame grows, finding funding has become easier. But expectations are high.
“A lot of times entrepreneurs are afraid of taking risks as a second-time entrepreneur. People are afraid of losing what they’ve already gained, so they take fewer risks,” she continued in the interview. “That’s not what you want to do when you’re running a start-up; you want to embrace risk.”
She doesn’t mind starting over, and she sees it a challenge, often giving advice to other entrepreneurs.
“Hiring’s one of the most important things you can do. Entrepreneurs need to start building today,” she added. “The barrier to entry in tech is low — so start designing, start coding it, launch it, build prototypes, build a working version of it.”
The Accidental Success
Fake admits she’s an “accidental business person,” which is what makes her so successful. She’s not in it to make money, but instead to explore the creative side of the Internet, whether it’s through community or connection. And through the process, she’s parlayed her lack of tech experience into the creative ideal of the “beginner’s mind,” which lets her see solutions in technology that others don’t.
As a result, she’s infiltrated the male-dominated world of Silicon Valley, and joined luminaries like Twitter’s Evan Williams and Biz Stone, who now operate a new start-up called Obvious, and Sean Parker and Shawn Fanning, who moved from Napster to Airtime.
She also won several awards, including BusinessWeek’s Best Leaders of 2005; Forbes’s 2005 E-Gang, Fast Company’s Fast 50 and Red Herring’s 20 Entrepreneurs Under 35. Even more impressively, in 2006, Time Magazine named her to its list of the World’s 100 Most Influential People. She also appeared on the cover of Newsweek that same year.
Fake won’t rest on her laurels, since awards and accolades aren’t a major driving force. Instead, she looks to creativity for motivation. In fact, she even joined the board for Etsy, the huge online crafts and antique marketplace, in the site’s early days, when CEO and founder Rob Kalin sent her an e-mail.
“I saw it, and I immediately loved it,” she told the New York Times. “At the time, it had only about 5,000 users, but it had a flourishing community.”
Unlike some, she isn’t on the board as a figurehead. She’s worked hard to ensure the site thrived, securing funding and delving into day-to-day operations. For example, she used a lesson she learned at Flickr to help manage Etsy’s comments — feature the voices of those who should be heard while stifling the trolls.
Even with all the fame and fortune, not to mention the awards, Fake says being an entrepreneur isn’t all about the money.
“The Internet has amazing powers of distribution,” she told Inc. Magazine. “You can test your ideas. You can see if it works, if it doesn’t work, whether it’s fun, and whether you’re sufficiently motivated. People who go into entrepreneurship to get rich aren’t going to be happy. It’s the building of things that makes you happy.”
Spoken like a true artist. ♦