One astonishing documentary came out of the dot com boom and bust:Startup.com.
The story of a startup called Govworks.com founded by a former banker, Kaleil Isaza Tuzman, and a programmer, Tom Herman, it won’t be giving away the story to say that Startup.com chronicles the full rise and crash of a high-profile, venture-backed Internet startup from May 1999 to December 2000.
Simultaneously poignant, funny, disturbing, and edifying, the film is now a key part of the historical record of what actually happened during that time, and required viewing for anyone who is starting a company, wants to start a company, or is even thinking that starting a company might be a fun thing to do.
Key moments to watch for: the venture capital pitch scenes in which the documentary filmmakers were not allowed to participate — filmed hilariously from outside the VC offices; what you got when you hired a roomful of super-expensive web design consultants in that era; the filmmaker’s clever demarcation of events by highlight “number of employees” at appropriate points in time; and the amazingly fast pace at which it is possible to burn through $60 million in funding (c.f. that roomful of super-expensive web design consultants) to put up a web site with which people can pay parking tickets in a few towns and cities.
Disclaimer: I met Kaleil during that time and found him to be a really nice, hard-working guy. He has since gone on to run a consulting firm that specializes in restructuring failing startups (true!).