At one point, Amazon lost more than 90% of its value. But long-term investors still got rich

Amazon's next big hurdle? The dot-com bubble.

In the late 1990s, dot-com companies became all the rage on Wall Street.

Amazon's customer growth and savvy capital fundraising combined to help it rapidly expand its offerings. Soon books became just one part of an expansive online retailer connecting customers with everything from power tools to Pokemon cards.

The company's valuation soared, hitting more than 50 times its IPO value in December 1999.

But Nasdaq peaked shortly after on March 10 2000, at 5,132.52. And the bubble burst, sending the composite down to barely 1,100 by October 2002.

As the crash set in, dot-com companies began folding left and right. Geocities, Webvan and Boo.com were suddenly gone. Hot start-ups like Pets.com and Kozmo that Amazon had invested in itself disintegrated.

Amazon's stock tumbled month after month as well, losing more than 90 percent of its value in two years.

The company weathered the storm, reportedly because of shrewd management and a lucky last-minute infusion of capital right before the bubble burst.

But even for those who bought in at Amazon's dot-com era peak, the investment still paid off. A $1,000 purchase of Amazon in December 1999 would be worth $15,500 today.

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