Evan Sharp & Ben Silbermann
The guys behind Pinterest look to take the wildly popular site beyond social.

The virtual bulletin board Pinterest had more than 48 million unique visitors in December 2012—more than 10 times its traffic a year earlier. Now cofounders Ben Silbermann and Evan Sharp, both 30, are looking to capitalize with an upcoming redesign and a retooled business model that they hope will shed the site's image as a hub for DIY crafters and bored brides-to-be. Sharp insists that the company's goal is to offer users "endless opportunities for discovery." But turning all those clicks into dollars is the next step, and tellingly, Pinterest has cemented a major entertainment deal with NBC's The Biggest Loser and acquired the recipe aggregator Punchfork, a purchase that was likely motivated by three letters: API. Punchfork may look like a simple food-porn palace, but its unique application programming interface has the power to turn Pinterest into a lucrative e-commerce site. The company could have developed its own API, but with Google and Amazon on the march in the one-click-purchase market, it acted quickly, using its wealth (estimated valuation: $2.5 billion) to buy a proven system. When Pinterest 2.0 rolls out and you see a shirt you like, you'll be able to not only pin it but also buy it—and, of course, Sharp and Silbermann will pocket a commission on the sale.

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Five More Entrepreneurs

Ryder Ripps
26, cofounder of digital creative agency OKFocus
Mission: Treat client jobs like art commissions, turning Web 1.0 artifacts (glitter graphics, nineties-era animated GIFs) into addictive sites.
Backstory: After starting as a conceptual artist, Ripps began creating renegade websites and digital marketing campaigns (with partners Jonathan Vingiano and Jules Laplace) for clients like M.I.A. and Google.
Calling card: WhoDat.biz, a site that posed as a Kanye West start-up; the prank was covered by the Washington Post and Gizmodo, proving Ripps'claim that OKFocus is "good at the Internet."

Ryan Holmes
38, CEO of HootSuite
Mission: Build a cloud-based tool to manage multiple social-network accounts—Twitter, Facebook, LinkedIn—from an easy-to-use dashboard.
Backstory: In high school, Holmes founded what would become the top online paintball-equipment supplier in Canada. He later dropped out of college, owned a pizza restaurant at 23, and started Invoke Media, where he launched HootSuite in late 2008.
The revolution will be socialized: "When Egyptians used HootSuite to post to their social-media accounts during the Arab Spring because Twitter and Facebook were blocked, we knew we had created something special."

Gillian Casten
27, founder, RateYourBurn
Mission: Create a Yelp for workout fanatics, who can review and rate trainers and instructors. The site currently covers New York City, Los Angeles, and Boston and will expand to three more cities in March.
Backstory: Casten worked in private equity and "saved every penny" before launching RateYourBurn out of frustration with the poor quality of pricey fitness classes she attended.
Blowing the gym whistle: "The fitness industry is grossly unregulated. Someone can get 'certified' in a matter of hours."

Ben Lerer
31, cofounder, Lerer Ventures
Mission: Invest in fashion-minded social-commerce sites like the eyewear-maker Warby Parker and the apparel e-tailers Everlane and Flint and Tinder.
Backstory: Lerer turned his popular men's-lifestyle newsletter, Thrillist, into a $50 million juggernaut by integrating it with fulfillment house JackThreads, opening his eyes to the power of combining content and commerce.
Team of rivals: "There may have been a time when my thinking was 'Keep your friends close and your enemies closer,' but there's space for a bunch of people to be really successful here."

Phil Ivey
37, founder, IveyPoker.com
Mission: Teach the world how to play poker with an app and a subscription site, IveyLeague.com, where users can watch instructional videos, get expert tips, and bet against star players.
Backstory: Ivey, considered by some the game's best player, is returning to the spotlight after a 2011 scandal in which the gaming site Full Tilt Poker—for which he was a spokesman—shut down.
Why he's all in: "I just played 15 hours straight in Macau, and I learned things. And I'm one of the better players. So there's an opportunity for people to get the same enjoyment I've had all these years."

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The Digital Mavericks

Jack Dorsey (Square)
+ 3 More Reinventors of Retail

Kenna (Myspace)
+ The Protégés of
Apple's Jonathan Ive
+ The Evangelists of Tumblr

Carter Cleveland (Artsy)
+ The Race to Create
the Instagram of Video
+ The Rise of the Social-Media
Image Consultant

Jennifer Pahlka
(Code for America)

+ 3 More Digital Change Agents

Evan Sharp & Ben Silberman

+ 5 More Entrepreneurs

Jared Leto (VyRT, The Hive)
+ How Twitter Became
the Best Place for Comedy