Webvan

Louis Borders, who had earlier founded the Borders bookstore chain, started Webvan in 1996 on the idea that groceries would be ordered on the web and delivered within a 30-minute window. Rather than start small, the company signed Bechtel to build automated mega-warehouses city after city, before demand had been proven in a single one.

The 1999 IPO valued Webvan in the billions. In July 2001 it went bankrupt, and alongside Pets.com its name became the stock example of dot-com excess. The irony is that the idea was right: Amazon and others now build roughly the same thing, just more slowly and funded by another business.