Without question, for me, the best is Startup. com:
It’s a documentary. Of a start-up, started by good friends, that sort of, just barely knew what they were doing. That raised tons of money from great VCs. That blew up.
While the movie in some ways is dated (it’s a Web 1.0 story), the human side of it isn’t 1% dated. Having to fire your co-founder, when he can’t carry his weight — even though you need him. When it doesn’t go according to plan. Trying to create culture, but doing it inauthentically. The retreats. The PR. Of having a Big Vision, but not being 100% able to execute against it.
Today, it would be much different to do exactly what they did (GovWorks), and today I am sure there are many success stories in the space. Web 1.0 was much smaller. But people are the same.
Watch this. Do better.
Great nonfiction is always so much more real.