12 Internet players you’ll want to know about

Illustration by Mark Zurolo '01MFA. Silbermann: Pinterest HQ. Fleiss: Courtesy Rent the Runway. Ryan: Courtesy Gilt Groupe.

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3 Entrepreneurs

“I’d always thought that the things you collect say so much about who you are,” said Ben Silbermann ’03 in a speech at a 2012 conference for bloggers. “And I felt like none of that was online.” Silbermann has taken care of that. He’s a cofounder of Pinterest.

Silbermann started reading technology blogs soon after graduating from college, and they changed his life: he left his job at a consulting firm and moved to California, where he landed a post at Google. But in 2008 he left that, too, wanting to make something of his own, and teamed up with Yale classmate Paul Sciarra. Their first effort, a shopping app, failed to take off, but—inspired by Silbermann’s childhood hobby of collecting bugs and stamps—they came up with the idea for Pinterest. Sciarra has now left Pinterest for a venture capital firm, but Silbermann remains as CEO. As of last July, Pinterest had 70 million registered users.—Melanie Asmar

Morgan Stanley, Lehman Brothers, and Harvard Business School: prerequisites for a career in fashion? For Jennifer Fleiss ’05, yes. In 2009, she cofounded Rent the Runway with business school classmate Jennifer Hyman, to help women solve what Fleiss calls “the ‘closet full of clothes but nothing to wear’ problem.”

Rent the Runway—a website where users can “buy” designer clothing and accessories for the short term—now has a membership of more than 3.5 million, an inventory by 175 designers, and a valuation Bloomberg puts at around $200 million. Revenue has grown 100 percent year over year, says Fleiss. Fleiss has been named one of the top most influential women in technology (Fast Company) and a “Top 30 under 30” (Inc. magazine).—Jennifer Conlin

Look at Gilt.com once and they’ve got you. Kevin Ryan ’85, chair of the Gilt Groupe, wants you to buy what the high-end online retail site has to sell—fashion, home products, travel, and more. And the site isn’t subtle about it. The e-mails arrive often enough to keep you looking, though not so often that you block them as spam.

Ryan’s entrepreneurial career began with the 1995 launch of the Dilbert website, but he’s best known for DoubleClick. In nine years heading the Internet advertising host, he took it from a 20-person start-up in 1996 to a multi-billion-dollar industry leader, acquired by Google for $3 billion in 2008. Now chair and CEO of AlleyCorp LLC, an incubator of technology and Internet companies, Ryan cofounded the Gilt Groupe and two companies in the AlleyCorp network. He told Mashable.com that success doesn’t hinge on a brilliant idea: “Any time I’ve started an idea, including Gilt, if it’s any good at all, there are 20 people doing the same thing.… It’s all about doing it really well.”—JC

McNamee: Courtesy Elevation Partners. Glaser: Associated Press.

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2 Founding fathers

Roger McNamee ’80, who moonlights as a guitarist with the band Moonalice, long ago established “near-wizard status” (Portfolio) as a tech analyst and investor. At T. Rowe Price he invested in the gamemaker Electronic Arts in the late 1980s; he’s now founding partner of the venture capital firm Elevation Partners, which invested early in Facebook. McNamee sits on Wikimedia’s board and is a special adviser to its director.—Kate Barnes

A decade before YouTube and Pandora, Rob Glaser ’83 had the idea of bringing the Internet alive with audio and video. He was VP of multimedia and consumer systems at Microsoft, but left in 1993 and the next year launched Real, later known as RealPlayer, a pioneering service in streaming audio and video. Still at the head of RealNetworks (RealPlayer’s parent company), as chair and interim CEO, he is introducing RealPlayer Cloud, for accessing, storing, and easily sharing videos between devices. “The process of reinvention continues,” he says. He also advises startups in digital, social, and mobile media.—MA

Yale University

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1 Yale professor

David Gelernter ’76, ’77MA, has paintings in the Yeshiva University Museum and the Tikvah foundation. His books include Judaism: A Way of Being and America-Lite: How Imperial Academia Dismantled Our Culture and Ushered in the Obamacrats. But he is best known as a digital seer.

In the early 1980s, he designed a programming language for linking computers together in networks. A few years later, he and a colleague demonstrated how to build a class of fast parallel programs that would prove to include web search engines and that anticipated the development of the digital cloud. Mirror Worlds, a company he had founded, argued in 2008 that Apple had drawn on its ideas, though it lost a patent infringement claim.

Regardless, Gelernter’s reputation has been made. The cofounder of Sun Microsystems once called him “one of the most brilliant and visionary computer scientists of our time.”—JC

Gordon: KPCB. Sze: Courtesy Greylock Partners.

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2 venture capitalists

When Bing Gordon ’72 graduated, he moved to New York City with dreams of becoming an actor. When he found he’d become “an expert waiter” instead, he tried several more jobs, including a stint as a commercial fisherman.

Then he enrolled in business school at Stanford. That was where he met the fellow student who went on to found Electronic Arts, in 1982; Gordon joined and spent the next 26 years there, becoming chief creative officer and helping to create such successful games as SimCity, John Madden Football, and Need for Speed. He is now a partner at the VC firm of Kleiner Perkins Caufield & Byers, where the companies he has invested in include Zynga, maker of FarmVille and Words with Friends; and ngmoco, which makes games for Android and Apple systems. “I try to see every new game company with potential,” he says.—MA

David Sze ’88 spent four years working for the early search engine Excite at a time, he says, when “everyone was in over their heads. You were making it up as you went along.” Today, as an investor at Greylock Partners, he’s drawn to small tech companies that have yet to make a profit—“the classic couple [of] people, a dog, and a garage.” One of his small-company investments, in early 2006, was a closed network of several million college students. Some questioned his judgment, but he stuck with the venture. It’s called Facebook.

Sze’s other investments include the networking site LinkedIn and the music streaming service Pandora. He funded Pandora at a time when many said no one could make money on music. But when VCs support a company, says Sze, “our job is to figure out the reasons it could succeed.”—MA

Mark Ostow

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1 journalist

“The weird thing about my winding up with a science/tech career is that I’m not a scientist or technologist,” says David Pogue ’85, who graduated from Yale with distinction in music. “I’m always the one seeking understanding, not the one possessing it.” Fair enough, if you leave out the part in which Pogue, tech reviewer extraordinaire, shares what he’s learned with millions of readers. “Millions” is literal: he cowrote seven books in the For Dummies series and created the Missing Manual series (more than 120 books on operating systems and applications). There are now over 3 million copies of his books in print.

Until last fall, Pogue was probably best known for his weekly column and blog in the New York Times. But he recently moved to Yahoo, where he is running a new multimedia consumer-tech site.—JC

And don’t miss…

Ime Archibong ’03 says he has the best job at Facebook. As director of strategic product partnerships, he works with companies such as Spotify and Nike to develop products that allow Facebookers to share the music they’re listening to or how far they ran on Tuesday.

Apps such as the Nike+Running App take it one step further, by allowing your Facebook friends to “like” your run in real time. The project has grown enormously, says Archibong: “It’s gone from a thing I’m doing solo to a scaled marathon experience.”—MA

Matt Wallach ’94 views one of his jobs as helping to get the right medications to the right people. As cofounder and president of Veeva Systems, he develops cloud-based software for life sciences companies like Pfizer. That includes e-mail, customer portals, and technology that helps pharmaceuticals sales representatives to manage their interactions with physicians. “This industry gets kind of a bad rap,” Wallach concedes. But, he says, the sales reps have to educate doctors on which new drugs are available and how they should be used. And he wants to help them do that more effectively.—MA

Courtesy Floodgate

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Ann Miura-Ko ’98 majored in electrical engineering at Yale, where, as a work-study student in engineering, she once gave a tour to Hewlett-Packard’s CEO. That led to a week shadowing HP executives, a week that convinced her to go into business. She went to graduate school at Stanford—where she now teaches entrepreneurship classes—and has cofounded a Silicon Valley venture capital firm, Floodgate. Her investments include ModCloth, a vintage-inspired clothing retailer that, she says, exceeded $100 million in revenues in 2012; and Lyft, a ridesharing app that recently secured a $60 million investment from another VC firm. —MA