Caterina Fake was one of the early entrepreneurs to glom on to the power of Web 2.0. While working on an online gaming product for a Vancouver-based company, Fake and her then-husband started Flickr as a side project. It launched in February 2004 without a single penny of venture capital—and a little more than a year later it was acquired by Yahoo! for nearly $30 million. Building upon this success, Fake launched Hunch.com in June 2009 to capitalize on the Web’s recently discovered power for crowdsourcing. Hunch is akin to Amazon.com's recommendations feature, except that it makes recommendations for everything. “You can use it, for example, to find a hotel in Dallas that you'd like, even if no one in your social circle has been to Dallas recently," says Fake. The company just secured an additional $12 million in funding, and claims 1.5 million unique monthly visitors. Though she’s nothing short of a power player, sitting on the boards of both Etsy and Creative Commons, Fake proves that an engineering degree and an MBA (she has a bachelor's in English literature) aren't the hallmarks of a successful Internet entrepreneur. Her advice to aspiring businesspeople? Drop out of college.
Poornima Vijayashanker has never been afraid to take risks. In 2006, she jumped ship on her master's in computer science at Stanford University to join the Mint.com team as its third employee and founding software engineer, aka "code monkey.” As the only female on the team, she got " picked on a lot." But she thrived nonetheless, handling nearly everything from front-end to back-end. She even came up with the company's name. Since leaving Mint in January, the self-professed " femgineer" has set out to start her own company, BizeeBee, and has been pitching her product to investors. "I came up with the concept for BizeeBee by exploring my passions, one of which is yoga,” she says. “Over the years I've noticed a lot of pain points”—in the business sense of the term—“that the owner of my yoga studio has had that I thought could be easily resolved with simple software solutions." BizeeBee will produce software for small businesses, aiming to translate the simplicity of Mint’s user experience to her own product. Despite her entrepreneurial spirit, Vijayashanker is an engineer at heart. "I truly love coding and solving engineering problems day and night," she writes on her website.
Meebo.com is already defying expectations for its against-stereotype leadership team. Of the company's three co-founders, it's the two women who bring the engineering chops. Sandy Jen and Elaine Wherry, with degrees in computer science and symbolic systems respectively, teamed up with fellow Stanford alum Seth Sternberg (MBA) to start Meebo, a browser-based, all-in-one instant-messaging service. In 2005, Jen was frustrated with having to remember all 13 screen names for her various instant-messaging accounts, and after fiddling around for a few months with Wherry and Sternberg (and leasing server space with their personal credit cards), Meebo was born. These days, Meebo claims 140 million users and has been valued in the hundreds of millions of dollars. Nielsen/NetRating has named it the fastest growing instant-messaging destination in the U.S., ahead of Google Talk and Skype Messenger. "We think about the Internet as an ecosystem, not a loose collection of sites," says Jen. "There is so much you can do once you are able to connect users in ways they want and need."
Rashmi Sinha made the jump from life as an academic to the Web when she got bored of working in a lab. She started by dipping her foot into the tech arena when she cofounded Uzanto Consulting, a company that provided user research for technology products to companies like Microsoft and Yahoo! That enterprise eventually helped launch SlideShare in 2006, where Sinha is co-founder and CEO. SlideShare is like YouTube for PowerPoint or KeyNote, creating a social network of sorts for presentations. Want feedback on your product or service? Float it out there by uploading to SlideShare, where community members can then add to, comment, and share with others. Among Sinha's notable accolades are being named to Fast Company's Most Influential Women in Web 2.0, not to mention making it onto Playboy's list of America's sexiest CEOs. "Women can have a different leadership style and if you don’t understand that style, it can be a blocker in funding women," Sinha writes about her own experience when seeking financial backing for SlideShare. "I don’t think they were against women CEOs, rather it was the particular leadership style they did not want to fund."
Ever since Heather Harde transitioned from Fox Interactive Media to CEO of TechCrunch in 2007, industry pundits have kept a close eye on her. The wildly successful and profitable tech blogs of TechCrunch, started by Michael Arrington, track the minutiae of the tech business, covering everything from products to startups. (In a coup in 2006, TechCrunch broke news of Google's acquisition of YouTube.) Harde was recruited by Arrington to grow TechCrunch from a blog to a media company, making her a major influencer among venture capitalists and technology companies. She’s used to dealing with big transactions; at Fox, she oversaw a $2 billion budget for mergers and acquisitions. In 2007, Harde and her blog empire hosted the Crunchies, recognizing key leaders in technology and innovation. She also recently helped organize TC Disrupt, a competition and conference to hook up New York startups with investors—an event for which they struggled to get a woman-led team to attend. For Harde, the move from a media company to TechCrunch was a perfect hybrid of her longtime interest in technology's impact on media. "I really do think blogs are going to be the future medial channel," Harde said in 2008, "because of the type of news that blogs are breaking."
Bringing together a network of 21 million women for its annual conferences, BlogHer is an online community of female bloggers who are fixing to translate their niche posts into income by connecting advertisers with potential customers. The site draws in 20 million unique visitors a month, and its articles, culled from a network of more than 2,500 blogs, are syndicated on sites from iVillage to Yahoo! to BravoTV.com. It has empowered some women, like Elise Bauer of Simply Recipes and Jen Yates from CakeWrecks, to turn their once-hobbies into a legitimate profession. One of the company's biggest gets was when Michelle Obama penned a blog post for them in 2008 during the presidential campaign. "I’m excited to be posting on BlogHer," the first lady-to-be wrote. "Not only because blogging is something I’ve actually been able to beat my daughters to, but because it gives me the opportunity to tell you a little bit about them, my husband, myself, and our experiences traveling all over this great country." What's most impressive about the enterprise is that after two years of bootstrapping, Stone, Page, and Des Jardins are one of the few women-founded teams to have secured three rounds of venture funding, totaling $15.5 million. They're expecting to turn a profit this year.
Darcy Padilla
Before Tumblr and David Karp, there was Mena Trott. Credited for starting the blogging boom, Trott was an avid blogger with a personal blog way back in 2001. Dissatisfied with existing blogging tools, she and her husband Ben developed Moveable Type out of their spare bedroom. Since then, the Trotts have also been responsible for TypePad, LiveJournal, and Vox, all highly popular, mainstream blogging software for the masses, some of which they developed and some of which they acquired. The blogging platforms now exist under Six Apart, the company Mena and her husband started in 2002 and of which she is co-founder and president. The blogging phenomenon doesn’t look like it’s going away any time soon, and neither is Mena Trott.
A fresh graduate of the University of Minnesota in 2006, Leah Culver wanted to use her computer-science degree to forge a career in programming. With empty pockets, this future entrepreneur drew upon her creativity instead: Culver decided to sell ad space on her yet-to-be-realized laptop. The idea worked, and at $50 per square inch of ad space, Culver got her shiny new MacBook, onto which she laser etched all the ads for the real estate she sold. Culver’s self-starter attitude led her to become co-founder and lead developer of Pownce, a blogging and social-networking site that was shut down in November 2008 when it was acquired by Six Apart, the company behind a handful of popular blogging platforms. "Starting a business was more about the freedom to create my own software than about being an entrepreneur," says Culver. "The idea for Pownce came from wanting to make it easier to share fun stuff with friends." She's trying that again with her newest project, building LeafyChat.com, an Internet chatting application.
Everyone enjoys a little bit of food porn, which is why Foodspotting makes so much sense. The company is the brainchild of Alexa Andrzejewski, who, upon returning from trips to Japan and Korea, wanted a way to discover where to find the dishes she had enjoyed abroad, like okonomiyaki and tteokbokki. "My initial idea was actually not Internet-based—I wanted to create a book—a Field Guide to Food, that would essentially be like a bird guide, but with pictures of food and basic facts about the foods." After realizing that a book wouldn't help people find the dishes they wanted, and that existing guides focused mostly on restaurants, Andrzejewski came up with Foodspotting. The service is a "foodie-powered field guide” with user-generated sightings of specific foods at specific locations. Think Yelp, but focused on dishes rather than restaurants. Foodspotting has so far been able to operate without any investor money; the team is paying for everything out of pocket. An iPhone app launched in March, and has already been downloaded more than 100,000 times.
If influence can be measured in Twitter followers, Soraya Darabi's is certainly on the rise. The 26-year-old spearheaded The New York Times' push into social-media marketing. Times columnist Nicholas Kristof credits Darabi with his impressive count of Twitter followers and Facebook friends. And after winning the Gray Lady a top prize at the INMA awards in 2009, Darabi recently made the cover of Fast Company's 100 Most Creative People in business, falling between the likes of Lada Gaga (No. 1) and Andrey Ternovskiy (No. 100), the teen founder of Chatroulette. Darabi left the Times in late 2009 to become product lead at drop.io, a real-time online project-sharing, collaboration, and presentation service. Darabi graduated from Georgetown in 2005 with a degree in English literature, but says she'd "give anything to go back to college and double major in computer science." "Women are simply not taught to think technology and programming are cool and worth exploring until it may be too late," she says. So how does this savvy non-engineer get a leg up in the Internet world? By harnessing the power of her social network, of course. "It's all a game of online telephone, and I'm tapped into a network that probably hears the message first."
