John Brockman occupies an office in the Fifth Avenue penthouse that once housed the New York Playboy Club, a detail he very much enjoys sharing. He is the type of agent who can make the words “three thousand dollars, MIT Press” sound like the rudest insult, and this was the kind of answer he traditionally gave Rheingold to his book ideas. But in 1991 he called with a more Brockmanian offer: an editor in New York had heard about something called virtual reality and was willing to offer $75,000 for a nonfiction account. The only problem was that Rheingold was not especially interested in virtual reality. He was interested in virtual community—the new possibilities for disembodied, multiparty conversation that he had discovered on the Well. But in 1991 online communities had no cachet. Editors believed the internet was a flash in the pan. But virtual reality—now there was crucial techno-cultural innovation. “I’ll strangle you if you do not write this book,” said Brockman.

“No, I’ll strangle you if you do not write this book,” said Maas, when Rheingold told his wife of the offer he was going to refuse. So Rheingold wrote the book, which served a valuable delaying function, for by the time he finished with it there was more widespread recognition that the internet might be interesting, after all. His next book, The Virtual Community: Home-steading on the Electronic Frontier, was a best seller.

The first promoters of online communication harbored serious hopes that these new technologies—modems, bulletin boards, internet sites—would contribute to the resolution of social problems. By reducing the cost of publishing and by shielding appearance, accent, and other particulars of identity, online technologies might prove an antidote to prejudice and chauvinism. Rheingold shared this idealism and presented it forcefully. He was embraced by the next wave of internet promoters and embarked on a successful speaking career. He became, for a brief time, the executive editor of a commercial web site, HotWired (where I worked for him briefly), and then launched his own internet company, Electric Minds.

Neither of these forays into business was successful. Rheingold fought ferociously with the founder of HotWired and resigned after a few months. Electric Minds was generously funded by venture capitalists, then quickly went bankrupt.

“I was caught up in the excitement of the moment,” Rheingold says. “You could tell someone a story and they would give you two million dollars. But they wanted twenty million back in eighteen months.” Such returns were impossible to provide, and his investors pulled the plug. “It was really embarrassing to crash a dot com back in 1997, before everybody did it.”

The publication of The Virtual Community and his association with two early internet businesses earned Rheingold his “guru” label. The evident weakness of the internet as an ultimate cure for social conflict also earned him accusations of naivete. But he says he has never been overly credulous about the promise of technology.“At Whole Earth I published articles by Jerry Mander, who believes that things started to go wrong with the introduction of agriculture. And I published Kevin Kelly (author of Out of Control: The Rise of Neo-Biological Civilization), who is firmly convinced that we will happily live with twenty billion people on earth.”

Rheingold promises that his next book will articulate his criticisms more sharply. His subject this time is the social effect of pervasive computing—of the digital processors that will inhabit all of our appliances, and, eventually, our bodies. He has been spending time in Japan and Finland, where mobile communication is more advanced than in the U.S. Decentralized, highly mobile computer networks create opportunities to harness enormous power outside traditional channels. Individuals can build social, business, and political contacts, move funds, and collaborate on work across great distances, even, when necessary, maintaining anonymity and shielding their communications behind strong encryption. Such powers can be harnessed to any variety of ends. “What it is,” says Rheingold, in a message he includes at the end of every email he sends, “is up to us.”

Today Rheingold spends most of his time in a small office near Mt. Tamalpais, with a lush garden outside his door and an enormous flat-screen Apple monitor on his desk. “I’ve created my own fantasy world,” he says. “It is a combination of a quietist Zen retreat and a Reed conference.” His style of thought remains resolutely individualistic and countercultural. But he declines to interpret his retreat as a withdrawal. In fact, he still anticipates the end of the world, and still hopes that spiritual progress will spark a transformation in advance of obliteration.

“I believe that the world can be transformed instantly through the right idea,” he says. “If we don’t succeed, the process starts again with the cockroach. If we do, we’ll live in a different type of world. We are racing towards some kind of climax, and everybody has a contribution to make.”

Gary Wolf is a contributing editor at Wired magazine.