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Photo by John MidgleyGeorge Gilder listened to the technology, and became guru of the telecosm. The markets listened to his newsletter, and followed him into the Global Crossing abyss. yet he's never stopped believing.

The lunch plates were cleared long ago, and the waitress gazes vacantly out over an otherwise empty dining room. But George Gilder, his legs propped on a nearby chair, seems rooted in place, not quite ready to leave. We're lingering at a restaurant down the street from his office in Great Barrington, a hamlet set along a rural highway that winds through the southern tip of the Berkshires in western Massachusetts. Here, one of the tech world's more famous – and controversial – prophets is contemplating how he could have been so right over the past half-dozen years and yet seen everything turn out so terribly wrong. A look of anguish clouds his face.

"I knew that it was going to crash, I really did, " Gilder says, looking out a window on to Main Street. Since 1996, he has published the Gilder Technology Report, a monthly newsletter that in its heyday was arguably the most influential tout sheet on Wall Street.Photo by John Midgley He glances my way and notices my arched eyebrows. I had plowed through several years' worth of issues, and while I read page after page of praise for a lengthy list of seemingly promising telecommunications companies, I saw nary a hint of warning in anticipation of the Nasdaq's March 2000 tumble and the financial tumult that followed. He adds quickly, "I told people in early 2000 they should sell half their shares in these companies." Then he says, in a tone of self-rebuke: "I didn't say it often. I didn't put it in a newsletter."

He made the recommendation to sell, he admits, only within the limited confines of the Telecosm Lounge, his online salon for newsletter subscribers. He fumbles for words, starting one sentence, then another, before growing uncharacteristically silent and staring off into the distance.

Photo by John Midgley

Photo by John MidgleyFor a moment, he seems to be imagining what might have been if things had turned out differently. Gilder, 62, is the author of a dozen books; he has been shouted down by feminists on The Dick Cavett Show in the 1970s, faced off with Dan Rather over trickle-down economics on 60 Minutes in the 1980s, and debated the future of technology with the likes of Andy Grove and Bob Metcalfe in the 1990s. Now many of his partisans are calling for the tar and feathers. He starts another sentence, and again cuts himself off. Suddenly he squares his body, turns to me, and expels a slight, disbelieving laugh. "When you're up there surfing, " he says, "the beach looks beautiful. You never think about what the sand in your face might feel like until after you've crashed."

For a short stretch during the late 1990s, Gilder's newsletter made him a very wealthy man. Anyone taking a cursory look at it might wonder why. Every issue is densely freighted with talk of lambdas, petahertz, and erbium-doped fiber amplifiers. The eighth and final page, however, explains how so geeky a publication attained, at its zenith, an annual subscription base of $20 million. It's on the back page that Gilder lists the stocks he has dubbed "telecosmic" – companies that have most faithfully and fully embraced the "ascendant" telecom technologies in which he believes so wholly and deeply. "For a few years in row there, I was the best stock picker in the world, " Gilder says ruefully. "But last year you could say" – here, for emphasis, he repeats each word as a sentence unto itself – "I. Was. The. Worst." Most of the companies listed have lost at least 90 percent of their value over the past two years, if they're even in business anymore.

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