It is 1999. A man in a fleece vest is standing on a stage in San Francisco, holding a laser pointer aimed at a PowerPoint slide that reads: "Pets.com: The Future of Pet Ownership." The audience is nodding. Venture capitalists are already reaching for their chequebooks. Nobody has asked how the company will make money. That question, frankly, is a bit gauche.
We 'bout ta bubble, baby. Get ya waterproof vest.
The Richter Scales saw it coming in 2007 when they wrote their now-legendary parody song warning that Web 2.0 was inflating like a rubber duck in a bathtub. They were right, of course as right as anyone who says "this cannot possibly last" always eventually is. But in the dot-com era, the original bubble, the Platonic ideal of financial absurdity, the bubble against which all future bubbles are measured, nobody was listening to the cautious voices. The cautious voices were not invited to the foam parties.
Peter Thiel was there for all of it. He watched PayPal survive the wreckage, then sat down years later to write Zero to One, his meditation on startups, monopoly, and the peculiar madness of Silicon Valley. In the book he describes the dot-com crash with the clinical detachment of a man who made it out alive: the lesson entrepreneurs drew from the carnage was to be lean, scrappy, and humble. No grand visions. No world domination. No more mascots with sock puppets.
Thiel thought this was entirely the wrong lesson.
He was probably right, but let us not get ahead of ourselves. First, the bubble.
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The Valuation Was Vibes
The Richter Scales' song ticks through the absurdities of 2007 Web 2.0 valuations. Facebook at $15 billion, YouTube, MySpace and asks, politely but musically, whether anyone had done the math. The dot-com generation didn't even pretend to do the math. Analysts invented new metrics specifically to justify the numbers: eyeballs, stickiness, mindshare. If your company had enough eyeballs, the theory went, the money would eventually find its way in through some as-yet-undiscovered orifice.
Thiel would call this "indefinite optimism" the belief that the future will be great, without any specific plan for making it so. He contrasts it with what he admires: definite optimism, where you have a concrete vision and execute it. The dot-com era was pure indefinite optimism in a turtleneck. Everyone knew the internet was going to change everything. Nobody could quite explain their burn rate.
The NASDAQ peaked at 5,048 in March 2000. By October 2002 it had fallen to 1,114. Five trillion dollars of market value evaporated. The fleece vests were quietly returned to Patagonia.