Mr. Naylor is the newly minted head of advertising agency relations for Terra Lycos, the Internet service provider and portal. A cynic might conclude that's roughly equivalent to coaching the Sudanese national ice hockey team. Mr. Naylor has, by his own count, been through two failed IPOs, three ownership changes, at least three brand identities, and Lord knows how many different bosses. But the cynic hasn't contended with either the relentless optimism or the confident belief in his medium that Mr. Naylor exudes.
"It's Management 101, I guess," he answered, when I asked the big, dumb obvious question: Why had such a talented sales manager stayed true through the turmoil? "Rick Boyce, my first boss at HotWired, taught me that to be an agent of change in a place of continual change is a very good thing."
Mr. Naylor, who worked across the floor from me when I hung my hat at Wired magazine in New York, is a welcome tonic in an economy suddenly grown quite depressing. He is a reminder that all businesses depend ultimately on sales, and that great salespeople-men and women who can turn logic and vision into a great yarn, and float it on a helium balloon of hope-will be the cornerstones of the turnaround. Certainly in the media industries, and most assuredly in the unhappy "e" space.
I hadn't seen Mr. Naylor, who is 35, for more than a year when I ran into him at the American Association of Advertising Agen-cies annual meeting last spring. He was trying nimbly to engage the assembled executives in conversations about his company and the future of the portal space. I later took him to breakfast, to review his five years on the other side of the digital divide-and how he sees the next few developing.
"I left the magazine world just when I should've been seeking stability, when my oldest daughter was about to turn one," he recounted. He'd been at Vanity Fair, just as it was emerging from its post-Tina Brown period of uncertainty. "But having a child made me ask, `What gets me jazzed, and will get me jazzed for the rest of my life?"'
The answer came on a cross-country flight, during which he devoured MIT Media Lab founder Nicholas Negro-ponte's book "Being Digital."
After reading it, the notion of going back had no point," he said. "I'd drunk the Kool-Aid." He rapidly accepted an offer to become Eastern sales manager for HotWired, the pioneering search engine-cum-portal begun by Wired.
Mr. Naylor said he never subscribed to the theory that the Web would change the media game overnight, or even quickly-a central reason he stuck it out through Wired's failed public offerings, HotWired's acquisition by Lycos (after the magazine was separately bought by Conde Nast), and then Lycos' subsequent acquisition by the Span-ish phone company Terra.
"People forget that New York City isn't the real world," he said. "`Water Boy' was a movie the media elite didn't go to see," he noted. But when it premiered on the USA Network last month, four of its showings rated among the week's top 10. The elite, Mr. Naylor believes, were equally out of touch about the Internet. "Their belief that the rest of the world would gallop to the Web, that's insanity."
So, too, he says, is today's conventional wisdom-that Web media will amount to nothing.
I agree with him. Nearly half of all American adults use the Internet in a given month, according to Scarborough Research. Consumption of traditional media continues to sink. Other studies indicate that almost 50% of the crucial 12-to-24 demographic would sooner give up TV than Internet access.
In this environment, sitting at a place like Terra Lycos-the world's third-largest ISP, with a brand that, by Internet standards, is venerable-may indeed be reason enough for a salesman's optimism.
"There've been a lot of bad stories about the Web this year and last," Mr. Naylor said. "All we need is more attention to the good stories-like Staples.com making a $1 billion contribution to Staples' revenue.
"It's stories like that," he concluded, "that make me a missionary for the medium."
Mr. Rothenberg, an author and longtime journalist, is chief marketing officer at consultancy Booz-Allen & Hamilton.