Went public: June 8, 1999

Drkoop.com was hailed as the WebMD of its time. This health information domain created by former Surgeon General Dr. C. Everett Koop drew 1.4 million unique visitors per month and easily raised $88.5 million for its IPO. AOL caught wind of the company and shares began peaking at $45.75 each, resulting in a 4-year deal that rewarded the site $89 million. But like most start-ups in the late 90s, it became entrenched in the dotcom crash and bled tens of millions each quarter, flatlining in late 2001.