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Film · The screening room

Startup.com

Chris Hegedus & Jehane Noujaim (dirs.) · 2001

Documentary film-makers followed a dot-com startup from founding to collapse, without knowing in advance which it would be.

Why it is here

The film crew began following the company at its founding, which means everything captured is contemporaneous rather than reconstructed. Nobody on camera knows how it ends, and that is the entire value.

What it documents that almost nothing else does is the deterioration of a founder relationship in real time — two friends, under sustained pressure, arriving at a place neither would have predicted. Co-founder breakdown is among the most common early-stage failure modes and this is the only footage of it happening.

The dot-com context dates it superficially and not at all in substance. The interpersonal dynamics are exactly what you are trying to assess when you ask founders how they handle disagreement.

Read it if

You want to see a co-founder relationship fail, which is a thing you are underwriting every time you invest.

Skip it if

You need current technology context to stay engaged.

Pair it withFounders at WorkJessica LivingstonInterviews with founders about the earliest days of their companies, before anything worked — the period every other account skips.

Startup.com: common questions

Why watch a documentary about a company from 2000?
Because it was filmed contemporaneously by people who did not know the ending, and because it captures a co-founder relationship breaking down in real time. That failure mode is as common now as it was then and there is almost no other footage of it.
What diligence question does it inform?
The one about how founders handle disagreement. After watching this, "tell me about your worst argument and how it resolved" stops feeling like an intrusive question and starts feeling like an obviously necessary one.