The Venturepreneur

5. Silicon Valley

I know, not technically a movie. Still, this one might be the most accurate portrayal of an actual startup that I’ve seen. So much so that I actually can’t watch it for any length of time – it’s so realistic it conjures up PTSD from my startup days.

Things that resonate the most for me

1. It’s about a team. Sure, Richard Hendricks (portrayed by Thomas Middleditch) is the lead, but the team is the story. It’s an ensemble approach with rich individual characters, a lot like life.
2. Startup teams (especially guys) that live together are just like this. Messy, always working, trying and usually failing to have lives beyond work, unrealistic expectations, and trivial conflicts that become huge business issues.
3. Really smart people who can’t tell the difference things that matter and things that don’t.

What I didn’t like

As the name indicates, too much of the project is Valley-specific, especially the obsessive predominance of startup culture in which all the characters wallow. Other startup regions have more going on beyond startups, so it wasn’t as relevant to those of us outside.

4. The Social Network

Clearly the poster child for the startup movie genre, but it’s lower on my list because of that. Still, it’s great story and covers some good territory.

Things that resonate the most for me

1. Money changes people. The wrong kind of investors – and greed – can force otherwise normal people to do things that they would never do.
2. Going into business with your friends can be a problem. I’ve seen friends succeed in business (first hand), but more often I’ve seen the opposite.
3. The myth of the solo entrepreneur. One message that becomes quite clear in the film, and contradicts the marketing done for it (movie poster attached being exhibit A) is that Facebook was NOT a venture that Zuckerberg did all alone. He was the figurehead and decisionmaker, but it was a team that made it happen.

What I didn’t like

Probably because we all know how Facebook turned out, the fact that the company would be successful didn’t ever seem in any doubt to any of the characters. No matter how much of a juggernaut you may be riding on, the likelihood of failure is always on your mind.

3. Sneakers

Set in a startup and taking place in Silicon Valley, this one has a phenomenal cast including the late lamented River Phoenix. Sure, the movie isn’t about being part of a startup per se, and it precedes the quest for meteoric unicorn growth that feels so natural in our post-dotCom startup culture, but it nonetheless captures the spirit of what it’s like to work for a startup and a technical one at that.

Things that resonate the most for me

1. The constant quest for clients. The movie starts with Martin Bishop / Martin Brice (Robert Redford) trying to determine whether the visitors have budget to hire his company based on the quality of their shoes.
2. Dan Ackroyd’s character. Ackroyd plays “Mother” Roskow, who seems like the epitome of every hardcore sysadmin I’ve ever worked with.

What I didn’t like

Some of the technology, especially the well-funded stuff Ben Kingsley’s character is into, is more Hollywood than realistic. Too much slick glass and chrome and flickering LEDs. (Spoiler alert) I’m also a bit ambivalent about the “box” at the center of the plot – I guess the idea that universal decryption can be embedded in a chip that has to be accessed by the clever application of electronic probes is possible, but even for the time this was a bit of a Hollywood foil.

2. Ghostbusters

Spengler: “This ecocontainment system Ray and I have in mind is going to take a load of bread to capitalize on. Where are we going to get the money?”

Venkman: “I don’t know.”

At it’s heart, one of the world’s best movies is a startup story. Kicked out of academia, the characters have no choice but to take their ideas and go into business for themselves. Few movies show the sheer delusional confidence founders need to have to put everything on the line for their dreams. Venkman: “The franchise rights alone will make you rich beyond your wildest dreams.”

What resonated the most for me

1. It’s about a team. The three main characters know and trust each other, each one brings their own skills to the table, and none of them could do it alone.
2. They almost fail. Spengler: “This magnificent feast in front of you represents the last of the petty cash.”
3. The first employees outside the founders. They don’t share the vision in their bones. Winston Zeddemore: “If there’s a steady paycheck in it, I’ll believe anything you say.”
4. The euphoria of your first real client. Janine Melnitz: “WE GOT ONE!” I still think all startups should have an alarm bell they can punch when they make a sale.
5. What it feels like to have product-market fit. Janine talks on the phone while other lines ring incessantly in the background. “Is it just a mist or does it have arms and legs?”

What I didn’t like

Not much. My biggest disappointment wasn’t actually in the movie – it was learning that despite saving New York and the world via the most epic guerilla marketing PR even in history the business had fallen on hard times prior to the start of the sequel. I mean come on: ghosts are incontrovertibly real and there’s only one company that is positioned to take advantage of it? How on earth do you screw that up?

1. Tucker

One of the greatest startup movies out there. Not nearly as well known as the others on this list, Tucker is about a ‘transportation tech’ business in 1947, pre-dating Tesla by about 60 years. I’m sure Elon Musk has a well-worn DVD version of it in his library.

What resonated the most for me

1. Once again, it’s about a team. Tucker knows it can be done, but it’s the people around him that
2. The impact and involvement of Tucker’s family. Every inch of the story is about the family who support him and to whom he is devoted. This might be one of the few startup stories where that’s true.
3. The spit-and-baling wire that holds together their MVP. (Spoiler alert) Having set up a PR event far in advance of the product being ready (which is absolutely realistic), the team has to improvise to get it to work.
4. The pressure of finding and having investors. Tucker gets no after no and finally finds a kindred spirit. But the well is not bottomless and the venture is always on the verge of letting them down.
5. The fine line between confidence and confidence man. The thrust of the entire plot: how much was force of personality plus wishful thinking and how much was fraud? Flip this story around and you get Elizabeth Holmes and Theranos.
6. The sheer American-ness of the story. Tucker is about an underdog with grit and fortitude and good ideas and force of personality that sets out to make something that benefits his customers. It’s not about greed or betrayal, except on the part of those who want to thwart him.
7. The ending. (Spoiler alert) Sure, Tucker lost everything. But he – and all the circles around him – actually won. He did what he said he’d do.

What I didn’t like

As much as Tucker is a heroic, quintessentially American tale with first rate screenwriting, acting, costumes, and period sets, it’s ultimately a truly sad movie. The fact that Tucker is a mostly forgotten footnote to history – and that the movie about his story is hard to come by – is deeply depressing to me.

Joy

Barely a startup movie. While good on many levels and featuring a wonderful performance by Jennifer Lawrence, the main character is an inventor, not an entrepreneur. Nothing wrong with that, of course, but they’re not the same. It also feels like much of the story was about Lawrence’s character persuading others to help her rather than doing it herself.

The Founder

Not a startup movie. In fact it’s about the guy who usurped the founder title from the greatest startup people in history. When it comes to celebrating entrepreneurship, this one glorifies the opposite. It’s like if the protagonist of Tucker were the CEO of General Motors.

Steve Jobs / Jobs

Let’s be clear: I am a huge Steve Jobs fan. He’s on my list the way Babe Ruth is on the list of every baseball fan out there. The story of Apple’s early days is a truly amazing story, and both Ashton Kutcher and Michael Fassbender do epic work. But the Jobs movies of the 2010s – while very good – focused less on Jobs as a founder than as a visionary of a company long after product-market fit. Interesting, but not a startup movie.

Erin Brokovich

Seriously? This movie appears on many lists and I have NO idea why. Erin Brokovich was a paralegal, consumer advocate, and environmental activist. The movie was about a whistleblower and a publicly traded company. Not a bad movie, it just doesn’t belong on any list.