Around the Web--and the World Business traveler Craig Newmark started one of the Web's most powerful sites--but uses a travel agent to book his trips.

Here's some Web 2.0 irony for you: Craig Newmark, the guy behind one of the most successful websites ever-one that allows buyers and sellers from Boston to Beijing to connect instantaneously and (mostly) for free-spends a lot of time traveling to meet people face to face.

Newmark (the Craig behind Craigslist) is a frequent contributor on the social-networking site Twitter. One recent "tweet" read: "Starting several weeks of extended travel, getting too old for this." Based in San Francisco, he often combines business trips with his personal interests. A self-described "libertarian-influenced moderate," he travels to support causes including voter registration and "real support for the troops" through Iraq and Afghanistan Veterans of America. In September he was in New York to attend the Global Creative Leadership Summit and discuss the future of journalism with the New York Times Editorial Board. In October, his schedule included a D.C.-New-York-Boston-Vegas-L.A.-Detroit marathon.

Interestingly, this major internet figure says he recently started using a travel agent to book his trips. "I don't want to have to learn to use Expedia or other travel sites," he says. "The travel agent also makes it easier to cash in my frequent-flyer miles for upgrades. I'm 55, and the older I get the more important it is to be comfortable when I travel."

Tech companies sell videoconferencing systems that are more Star Trek than webcam.
After launching Craigslist in 1995 as a quick and dirty way to keep his friends up to date on events in his neighborhood, he and C.E.O. Jim Buckmaster developed the site into a gargantuan destination offering everything from personals and discussion forums to help-wanted ads and event calendars (not to mention the occasional offer of a kidney in exchange for two tickets to a Barack Obama speech). Today, Craigslist covers 567 cities around the world and gets 12 billion pageviews a month. Time magazine has named Newmark one of the world's 100 most-influential people.

Newmark himself is a quirky guy. His official title is Customer Representative and Founder and, while he's also chairman of the board, he gives over most of his day to helping users with their problems. Recently, he explained to a New York City apartment agency where they might best post on Craigslist, later acting as an intermediary between two bickering users.

When Newmark is on the road, his carry-on fairly bristles with high-tech equipment intended to make him more productive. In his e-arsenal: an iPhone and a Nokia N95 mobile phone, which serves as a mobile hot spot so he can connect his ThinkPad X300 laptop to the internet from almost anywhere. He used to carry a Sprint cellular modem until Sprint capped user throughput, a move, he says, that "doesn't strike me as very reasonable." Recently he began carrying a Kindle e-book capable of storing up to 30 titles. Convenient, yes. But cost effective too. "I'm guessing it'll pay for itself in 18 to 24 months just in the savings on hardcovers," he says.

And if all this gear doesn't keep him busy enough while flying through the troposphere, Newmark says he can't wait for airlines to begin offering in-flight WiFi.

"I'll be able to get much more work done," he says. "Keeping up with customer service, staying up to date with the news. Plus, there'll be even more entertainment options."

But Newmark says the prime benefit of traveling is the serendipitous meetings with people he might not otherwise meet, learning things he might not otherwise learn. While attending a recent conference, for example, he was introduced to Nita Lowey, Representative for New York's 18th Congressional District. Their conversation turned to the topic of lobbyists, a Washington species Newmark says he'd long been suspicious of.

"Representative Lowey convinced me that a small number of predators gives the lobbyist industry a bad name; that most are simply trying to get a fair shake for their clients, and some even lobby as a public service," he says. "When I later met her during the Democratic National Convention, I told her how our discussion had really changed my point of view."

Visit Portfolio.com for the latest business news and opinion, executive profiles and careers. Portfolio.com© 2007 Condé Nast Inc. All rights reserved.