The documentary "Startup.com" (2001) gives an interesting behind-the-scenes look that depicts the hard work involved in building the dot-com startup company Govworks (govWorks), founded by high-school friends Kaleil Isaza Tuzman and Tom Harman in 1998.
Govworks sought to provide citizens with a service that enabled them to manage city services online such as paying traffic tickets. The company raised $60 million in venture capital during its three years of operations, until it was affected negatively by the 2000 dot-com bubble and went bankrupt.