AOL and Time Warner combined at the peak of the Internet boom in a stock merger that promised digital-media convergence but instead exposed the danger of valuing strategic fit at bubble prices.
Webvan raised hundreds of millions of dollars and built automated grocery infrastructure at national scale before proving that online grocery orders could support the capital intensity.
Boo.com raised and spent more than $100 million trying to build a global online fashion retailer, but technical complexity, international expansion, and heavy marketing exhausted its runway.
Yahoo paid several billion dollars in stock for Broadcast.com in 1999, betting that streaming audio and video would become central to the web long before broadband economics stabilized.
Yahoo's multibillion-dollar GeoCities acquisition bought one of the web's largest user-created communities, but the portal model failed to convert that early social-web position into durable platform leadership.