5. Northpoint Communications

What it does: Competitive local exchange carrier
IPO Date: May 5, 1999
Money raised: $360 million

At the time of its IPO, NorthPoint, a company that handled data transmissions for ISPs, was one of the most promising companies of the 1999-2000 dot com boom. And then the bubble popped. With almost every company incurring serious losses, NorthPoint lost many customers which, in turn, hurt its yearly earnings for 2000. It was so bad, Verizon, which was on pace to purchase the company to merge its DSL service, took back its offer. A year later, NorthPoint  filed for bankruptcy.