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While other Silicon Valley chieftains embraced hobbies like fly fishing, hockey, wind-surfing and whitewater rafting -- all of which had become popular among legions of adoring engineers -- Barry's were particularly expensive and elite. They also required extensive support crews, guaranteeing no copycat nerdlings would be following him onto his chosen playgrounds.

Avocations can betray everything. People seem to choose hobbies that allow them to work out their deepest and most profound personal issues.

If there is any truth to this premise, Barry's issues were plain: Insecurity. Control. Power. Restlessness.

Take his flying habit. Whereas air travel might raise feelings of dread and insecurity in many, there was one thing Barry absolutely knew for sure: It was impossible for him to feel insecure in the cockpit of the MiG-21. When he leaned on the throttle and lit up his afterburners, there was absolutely no one -- outside of the U.S. Air Force and Area 51, perhaps -- who could catch him. This did things for Barry that years of therapy and hundreds of motivational seminars could not.

Then there was the rush of control. Unlike TeraMemory, the MiG had no CFO to suggest how much fuel to burn or how fast to fly. Barry hated collaboration, and delegating authority was like pulling out his own teeth. Dependency on others made him anxious. He liked doing it all himself. The jet spoke to that need.

As for power, there was something intoxicating about having a plaything that was until very recently the supreme instrument of force of a world superpower. Never mind the raw speed and aerobatic capabilities of this aircraft; Barry had only to add his name to the former owners' to become drunk with his own power and importance: Brezhnev. Gorbachev. Dominic. Actually, his own company's market cap exceeded the national economies of what was left of the Soviet Union.

A restlessness like Barry's is only abated by an infinity of choices. Mach 2 is crack cocaine to the restless; a change of heart and a wiggle of the stick, and you could be dining in Telluride instead of Las Vegas.

Yet the cyber-billionaire could not live by afterburners alone. What the jet did for obliteration of geographic barriers, the boat did for social ones. Yacht racing is a rich man's sport, and winning is reserved for the egregiously wealthy. But it's also the quickest shortcut across class barriers available to a relentlessly ambitious, cyber-industrialist arriviste like Barry. Even the Yalies in their club ties grudgingly afforded a measure of respect when Mr. Dominic -- and the very elite, very expensive crew aboard the Singularity -- jibed victorious through another San Francisco regatta.

It felt good to be on top -- in and out of the office. But the gratification never lasted very long for Barry. His ascent had presented him with a persistently insoluble problem: No matter how often he stepped up in the world, Barry was immediately treated to a view one step above that. And to a certain kind of personality, a fundamentally insecure personality like Barry's, being one step down from anywhere -- or in this case, anyone -- was an unacceptable breach of the natural order.

Who, in particular, did Barry see on the next step, catalyzing his insecurity? Undoubtedly it was Seattle Bill, the mightiest information-age magnate of all. The specter of Bill and his billions hung over Barry like a cloud, its shadow arousing such feelings of envy and inadequacy as to drive him wild.

And drive him it did, this stolen limelight. He thought of little else but the chariot that must sooner or later present itself, shining and ready, hitched to the twin steeds of technology and capital, ready to propel him to the promised land of unexploited market share. He would WHIP the horses.
salon.com | April 24, 1999

Coming Wednesday
Chapter 13: Managing for total chaos

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ILLUSTRATION BY OCTAVIO DIAZ