The top inspirational startup movies and documentaries

Like most, I love watching films and documentaries. But I especially love those that chronicle the building of something great. It might be the story of a business or startup, but really anything that tells a story of incredible growth and success.

These films are not always especially accurate, and most of them are dramatised with fictional betrayal or some otherwise overlay dramatic elements that never occured, but at the core many are very entertaining.

Once upon a time I used to believe that watching a great film could inspire me. That I could bottle up the experience and translate it into a lasting source of motivation for whatever I’m working on in the real world. But as I’ve got older, it’s become clear this isn’t how I operate, and I think I’m safe in thinking this is the case for the vast majority of others too.

A bit like a good gym workout, a good film will leave you feeling mentally ‘pumped’ and inspired to accomplish great things with haste. We’ve all had that feeling — I remember walking out of the cinema after just having seen ‘The Matrix’ for the first time, and it felt incredible, a feeling like I could take on the world. I also very much wanted a leather long jacket and dark sunglasses, which is rather embarrassing to think of now.

But in reality, life quickly seeps back in, and the feeling begins to erode. It’s probably say to say the half life of this inspiration is probably a few hours at most.

The reality of creating something big, especially a company, is a grind — a successive sequence of small tasks and accomplishments day after day, week after week, month after month, which of course is nothing like most films. They’d be pretty boring otherwise.

I believe true long-lasting motivation has come from inside: a burning desire to change something in the world, like an itch you just have to scratch. And when you’re in the thick of it, it’s often just a matter of survival —a very different to the feeling to the one you get after watching an amazing film, but far more powerful.

I love the way Jobs described his inspiration:

As such, I now just consider films, tv shows, and documentaries as great bite-sized sources of entertainment, and they’re usually now a reward rather than a means to an end.

With that in mind, I thought I’d put together a list of my favourite, ranked by my preference. I’ve also produced a publicly editable Google sheet where you can rank by IMDB or Rotten Tomatoes score.

If you know of any other good films in this category, please add them!

• The Social Network (2010), Rotten Tomatoes (96%), IMDB (7.7)
• Steve Jobs (2015), Rotten Tomatoes (86%), IMDB (7.2)
• The Founder (2016), Rotten Tomatoes (81%), IMDB (7.2)
• Limitless (2011), Rotten Tomatoes (69%), IMDB (7.4)
• Wolf Of Wall Street (2013), Rotten Tomatoes (79%), IMDB (8.2)
• The Aviator (2004), Rotten Tomatoes (86%), IMDB (7.5)
• Margin Call (2011), Rotten Tomatoes (87%), IMDB (7.1)
• The Pursuit of Happyness (2006), Rotten Tomatoes (67%), IMDB (8)
• Equity (2016), Rotten Tomatoes (83%), IMDB (5.5)
• Molly’s Game (2017), Rotten Tomatoes (82%), IMDB (7.4)
• Page One: Inside The New York Times (2011), Rotten Tomatoes (78%), IMDB (6.9)
• Fyre Fraud (2019), Rotten Tomatoes (79%), IMDB (6.8)
• Who Killed the Electric Car? (2006), Rotten Tomatoes (89%), IMDB (7.7)
• FYRE: The Greatest Party That Never Happened (2019), Rotten Tomatoes (91%), IMDB (7.2)
• Jobs (2013), Rotten Tomatoes (28%), IMDB (5.9)
• Pirates of Silicon Valley (1999), Rotten Tomatoes (90%), IMDB (7.3)
• Moneyball (2011), Rotten Tomatoes (87%), IMDB (7.6)
• The Fifth Estate (2013), Rotten Tomatoes (36%), IMDB (6.2)
• Micro Men (2009), Rotten Tomatoes (-), IMDB (7.5)
• Something Ventured (2011), Rotten Tomatoes (-), IMDB (7)

On my ‘to watch’ list:

• Startup Kids (2012), Rotten Tomatoes (-), IMDB (6.7)
• Generation Startup (2016), Rotten Tomatoes (71%), IMDB (6.7)
• Barbarians at the Gate (2003), Rotten Tomatoes (71%), IMDB (7.2)