"The Lost World of the Late Nineties"

Every happy family is alike, Tolstoy observed -- but what about every rich one? As it turns out, there are numerous ways to react when you stumble into a major fortune. Some Amazonians went on buying binges: cars, boats, clothes, art, fine wines, real estate, jewelry, first editions, more real estate. One programmer (and Harley Davidson enthusiast) strolled into a taco joint near the office and loudly announced that he had hit his lifetime trifecta: "I've got a hog, a house, and a hot tub!"

Others preferred to plough their gains back into a new, diversified portfolio. You had your hedge funds and T-bills, your bond ladders and blue chips. If you felt even more irrationally exuberant than usual, you could sink some spare change into the latest IPO-telecom, B2B, optical fiber -- and keep your fingers crossed. Whatever you did, the market kept behaving like a Roman candle, so it made no sense to park your cash in some chicken-feed bank account: that was the equivalent of losing money, throwing it out the window. You had to keep it circulating. Without a little bounce, a touch of Brownian motion, the dollars would go dead on you. They were always the means to some taxable, teleological end, which is to say, more dollars.

Then there were the people like me, who essentially behaved as though nothing had happened. Oh, it was a wonderful feeling to be relieved of all those financial pressures. Yet most of my old, neurotic inhibitions about money remained intact. We replaced none of our dilapidated furniture: when the cheapo particle-board table from IKEA finally busted, we threw it away and left a vacancy, like a bald spot, in the living room. I still found it difficult to buy a shirt, a watch, a compact disc. And every time I pondered a big-ticket purchase, I heard Chris's voice in my ear, urging me to avoid his dumb (and dumber) mistakes. This went beyond indifference: I was seeking protective camouflage. The idea wasn't to look poor, only invisible. Once in a long while, I took a hedonistic plunge: I bought an Ermenegildo Zegna tuxedo for my sister's wedding, whose upswept lapels seemed designed to accommodate a bigger wallet, and a beautiful Steven Andersen archtop guitar. Mostly, though, I continued to wear my underwear with the holes in it, not wanting to identify with the ruling class even on my way to the shower.

No doubt this reluctance on my part had less to do with thrift than with pathology. My father, a research scientist, always taught me to value creativity (which he had) over cash (which he didn't). He was right, of course. Still, there may be nothing in this world more crushing than a good lesson taken to heart. It made me suspicious of my own luck. This proved to be prescient in the long run -- as it so often does -- but it also made my lucre seem filthier than it really was. No wonder I kept my distance from it. In any case, I had found the ideal setting for operating as a stealth plutocrat. Seattle had a long custom of quiet wealth, invisible wealth. Even Bill Gates, the richest man on the planet and the jewel in the crown of the city's entrepreneurial mythology, followed suit. If he built himself a house as big as the local Sheraton, he had the good taste to bury much of it in a hillside.

I seldom discussed these matters, and never in any detailed way. Early on, a couple of months after the company went public, my sister asked me: "Are you a millionaire now?" I told her, honestly, that I wasn't. But once I was, I never mentioned the fact to her, nor to my oldest friends, who worked as hard as I did but weren't being rewarded with such insane sums, who simply weren't dwelling in the same Cloud Cuckoo Land as I was. An exception: at a certain point, I shared a few figures with my parents. In part this was to reassure them that they would no longer have to prop me up financially, as they had done for so many years. Yet I also wanted to prove that I had made good, that I had hit the jackpot, a childish impulse that I feared would fly right in the face of my father's ambivalence about material success. I needn't have worried. He embraced my riches with real gusto, and felt that I deserved much, much more. During his toast to the happy couple at my sister's wedding, he digressed for a moment to inform the audience that his son had virtually created the Internet's flagship retailer, and then implored Jeff to ante up: "Mister Bezos, surely James should be given a billion dollars." My brother, a bass player with a predictably erratic income, glanced down at the table. Thrilled and mortified, I perspired like mad into my fancy tuxedo.

In fact, my father was more in touch with the spirit of the age than I was. To get to the heart of an epoch, you can safely ignore its statements of purpose, its fiery declarations. Listen instead to the questions it asks. In 1863, surveying the panoramic misery of pre-industrial Russia, Nikolai Chernyshevsky asked: What Is To Be Done? In 1997, at which point the United States was supposed to be gliding into a radiant, post-industrial future, the question of the moment was: Who Wants To Be A Millionaire? The answer, needless to say, was everybody. But what made the Lost World of the Late Nineties so extraordinary was that such wealth seemed feasible, not merely to robber barons but to college students and taxi drivers, waitresses and pharmacists and postal carriers. Plenty of people -- most people -- were still scraping to pay their bills. The rich were undeniably getting richer. Yet the arbitrary nature of the boom, and the way it plucked its beneficiaries from all corners of the economic map, did suggest a certain leveling of the field. Egged on by Regis Philbin, every American could now dwell in Possibility.

Until, that is, March 10 of 2000. On that date the NASDAQ hit its all-time high, closing out the day at 5,048.62, and then commenced a long, ruinous slide, which would eventually siphon $3.8 trillion from our collective pockets. Most Amazonians were slow to panic. We had already seen the stock take a beating on several earlier occasions, then stage a miraculous recovery. And despite the sputtering economy, all the signs pointed to a blowout holiday season, in the course of which Amazon was primed to move more than a billion dollars worth of merchandise. Surely we would ride out the storm. In fact, the company might even benefit from a little culling, and enter the next year as the ultimate dot-com survivor.

Next Page: The Great Depression, 9/11, and why the author leaves his lights on

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