Film

Startup.com

Name: Startup.com
Genre: Documentary
Released: 2001
Cast: Kaleil Isaza Tuzman, Tom Herman, Kenneth Austin, Tricia Burke, Roy Burston

Drama

A documentary capturing the dot-com boom's manic energy through two childhood friends trying to build govWorks.com. You watch millions in venture capital flow, egos collide, and a friendship fracture in real time. It's a cautionary tale about ambition, greed, and the cost of chasing the dream when the dream is built on sand. Essential viewing for anyone curious about how the internet economy almost destroyed itself—and how it damaged people along the way.

TMDb rating

3.4

Should you watch it?

Watch it if you enjoy watching friendships strained by money and ambition, and you find the human side of the dot-com boom more gripping than its gadgets or jargon.

Skip it if you want a broader view of the dot-com bubble, since this stays tightly inside two men's lives rather than explaining the wider market around them.

What it asks of you: A long sit at under two hours, mostly talking heads and office meetings moving at a steady, unhurried clip, with tension gathering in quiet moments rather than loud ones.

Not sure? Find tonight's pick in a minute.

If you liked this

The Social Network2010

Same arc of brilliant young men building something world-changing, but with Sorkin's crackling dialogue and a clearer view of the moral rot underneath the ambition.

But The fictionalized drama feels slick compared to the raw, unglamorous reality of Startup.com. You might find it too knowing and performed.

The Toys That Made Us2017

A different kind of startup story—creators fighting for their vision in a corporate machine. Shows how personal and professional failure intertwine even in less high-stakes settings.

But Lighter in tone and stakes. If you're drawn to Startup.com's darker elements, this won't hit the same way.

Fyre2019

Another documentary about charisma, hype, and the gap between promise and reality. More recent, which makes the patterns even more infuriating to watch repeat.

But It leans into the absurdity and can feel like entertainment built from other people's humiliation. Startup.com is sadder; this is angrier.

Not sure tonight? Get a pick in a minute, starting from Startup.com

The wildcard

Something you would not have found on your own.

Four Rooms1995

Both are about what happens when talented people are locked in a confined space with conflicting agendas and competing egos, real-time. Both ask: what does this reveal about them?

A real-time bottle episode where four directors, two screenwriters, and a cast of characters collide in a single night. Like Startup.com, it's about proximity and pressure revealing who people actually are, but in miniature and comedically.

But It's a weird, undisciplined mess that many people find unwatchable. The humor is broad and the structure deliberately frustrating.

WeWork: or The Making and Breaking of a $47 Billion Unicorn2021

Proof that the dot-com playbook never died—same euphoria, same delusion, same inevitable reckoning. Shows how little changed in twenty years.

But It's infuriating in a way that can exhaust rather than engage. The repetition of the pattern might feel depressing rather than instructive.

WeWork: or The Making and Breaking of a $47 Billion Unicorn poster

Halt and Catch Fire2014

A drama series that captures the same obsessive drive to build, the same ego clashes and relationship fractures. It's Startup.com's spirit rendered as prestige television.

But It's fictionalized and aestheticized in ways that soften the actual damage. Some viewers find the nostalgia layer distracting.

The Great Hack2019

A documentary about Cambridge Analytica that shows how startup culture's 'move fast and break things' ethic bleeds into something genuinely sinister and consequential.

But It can feel didactic and preachy. The storytelling is less intimate than Startup.com's fly-on-the-wall approach.

The Godfather Part III1990

Both documents the fracturing of a relationship between two men bound by history, where one wants out and one can't let go. Both are about the cost of wanting more than the other person does.

A film about an aging man trying to hand off his empire to the next generation while his partner's son undermines him. It's about succession, betrayal, and watching a friendship die in real time.

But It's the widely acknowledged weak entry in the trilogy. Three and a half hours of Coppola repeating himself. Many think you shouldn't bother.

My Best Friend's Wedding1997

Both examine whether a friendship can survive when one person's needs and ambitions diverge sharply from the other's. Both say: probably not, and maybe that's okay.

A romantic comedy where the 'friendship' at the center is revealed to be transactional, possessive, and ultimately hollow. It's funny and light, but it asks the same question as Startup.com: can friendship survive ambition and self-interest?

But It's a Julia Roberts rom-com from the '90s. If you came to Startup.com for serious documentary realism, this will feel like a trivializing detour.