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2000 - Dot-Com Crash Begins

In January 2000, ubiquitous Internet service provider AOL moved aggressively into content creation by agreeing to buy Time Warner for a staggering $164 billion. It was the largest corporate deal ever, engineered by Time Warner chief executive Gerry Levin (left) and AOL boss Steve Case.

Wall Street had already seen a flood of dot-com businesses looking to go public in the late 90s, and when they did issue IPOs, the staggering market capitalizations made some nebulous companies, like TheGlobe.com, temporary market heavyweights.

But the bubble burst, as investors pulled out of companies that promised cool offices and high burn rates and shifted into actual revenue and profit-generating businesses.

Photo: Getty Images