The Web Masters

Think of 2008 as the year the Internet got greedy. As the recession goes digital, it's no longer enough to have an easy-to-use social-networking site, or blog software that corners the market on 13-year-olds. Now, companies like Facebook and Twitter are betting their futures on the proposition that it's time to become a hub, a place from which all other Internet activities stem. In creating our list of the men and women leading the Web, we looked to those who've courted customers and held on: Hulu.com is keeping viewers glued to television without the TV set. Facebook's new Connect platform lets users monitor what their friends are doing online. InterActiveCorp (IAC) is defining what it means to invest and succeed online; the Daily Beast, Tina Brown's news aggregator, is a favorite of journalists and bloggers alike. Meanwhile, former IAC execs are climbing the Washington ranks. Here's who succeeded the most:

Tina Brown
The Daily Beast
For Brown, it doesn't matter if you break the story. You just have to tell it better than the competition. That's the model for her latest venture, The Daily Beast, which combines original content with collected links from her staff's favorite news sites. If that sounds a lot like the eponymous Web site of a certain Greek force of nature, that's because, well, they are very much the same. Still, Brown has made a career out of rethinking the ideas of her predecessors. Sometimes that works (see: Vanity Fair, 1984-1992, or The New Yorker, 1992-1998), other times it flounders (Talk, 1999-2001). So far, the Beast is on track to fall in the first category: after the site launched in October, Brown and Co. racked up more than 11.4 million page views in their first month.

One of the site's early successes was a wacky profile of Jennifer Lopez that Elle reportedly refused to publish because it was too critical. Now the site is using Brown's name (and the big-money backing of Barry Diller's IAC) to court the best of the journalism world's recently laid-off. Considering that the penny-pinching site is rumored to pay a mere 50 cents per word, you can expect the budget—and talent—to go far.

Julius Genachowski
Web Wonk
A key part of President-elect Barack Obama's campaign legacy will be that he Twittered, texted and Facebooked to victory in a way that had never been done before. Obama's courtship of the Internet constituency worked so well that many expect he'll hire a chief technology officer by the time he's sworn in next January. Who's going to keep our president aware of the latest digital trends? We're looking at Julius Genachowski, a basketball partner from Obama's Harvard days who convinced the candidate to go digital early in his campaign. After that strategy helped Obama win the election, Genachowski was named a co-leader of the Obama transition team that manages technology, innovation and government reform.

The two men have been friends since they attended Columbia for undergraduate degrees together, then law school in Cambridge, where Genachowski was the notes editor under Obama's editorship of the Harvard Law Review. Since then, Genachowski has been no stranger to Washington. After earning his J.D., he clerked under Justice David Souter. More recently, he was the legal counsel for Reed Hundt, the former chairman of the Federal Communications Commission. (If Obama doesn't create a new technology officer, this experience may put him in line for the FCC chairman position.)

But Genachowski's latest ventures suggest that he is better suited as a digital adviser. After leaving Washington, he became an Internet entrepreneur, serving on the boards of Expedia, Hotels.com and Ticketmaster. From there, Barry Diller courted him to serve as InterActiveCorp's chief business officer, a position he held for eight years before starting LaunchBox, a platform for Web and mobile startups to pitch ideas and receive seed funding.

If one thing hurts his chances for success, it will be his East Coast background. Many blogs out of Silicon Valley already wonder whether Genachowski is really a digital whiz kid or just another Washington wonk. "Genachowski is a lawyer who I'm sure can grasp net neutrality," writes Paul Boutin of Valleywag.com "But if this turns out to be Obama's idea of a technologist, I'm going home to cling bitterly to my guns and religion."