10 Best Movies for Entrepreneurs to Watch

Everyone of all shapes and sizes, of all ages, and of all experiences, needs a little downtime. For busy minds, however, downtime is just another word for research. After all, inspiration doesn’t come to those who wait; it comes to those who seek it out.

The road to inspiration is often filled with many u-turns and avenues, instead of a straight path.

However, often the straightest path is to sit down and watch some thought-provoking movies.

With nearly a thousand movies made per year, it’s impossible to sit down and view them all. Luckily, this list offers ten of the best films that any entrepreneur worth their salt should have on their watchlist.

Wall Street (1987)

Rated R

Starting off our list is an obvious film for any entrepreneur. With Its infamous “Greed is good” speech, this one has become a pop culture touchstone. Its stellar casting, with Michael Douglas as the charismatic Gordon Gekko, is iconic, and it has a relatable protagonist in Bud Fox: an entrepreneur who is lured into the world of Wall Street by promises of wealth and fame.

As Bud Fox meets his hero and gets carried away by his glamorous lifestyle, every entrepreneur should take note how easy it is to be lured in and trapped by greed. 

Beyond just being a great film, Wall Street offers us a gentle reminder about how ambition can be our undoing if we’re not careful. Experience it for the first time (or the tenth!) on Apple TV and Amazon Prime.

Glengarry Glen Ross (1992)

Rated R

Glengarry Glen Ross tells the story of a group of real estate salesmen who are running out of time when things don’t go the way they should. This film is perfect for those who are going through tough times who want to know they’re not alone. 

With a colorful cast of characters, the film shows the full spectrum of personalities working in the hustle and bustle of a New York City real-estate office. However, even those not interested in sales will be struck by the film.

What happens when everything goes wrong? How do last year’s mistakes affect this year? When the pressure of earning a living becomes overwhelming, this is the film for you, and luckily Hulu, Amazon Prime, and Apple TV have you covered.

Jerry Maguire (1996)

Rated R

Directed by Cameron Crowe, Jerry Maguire tells the story of what happens when a sports agent decides to go independent. Entrepreneurs take note, for the film shows that success can be driven by virtue even when you are pinned against the odds. 

Remember that when the going gets tough, as it does in Glengarry Glen Ross, a good amount of ambition headed by virtue, not greed, goes a long way. Watch it on Amazon Prime today and you won’t be sorry.

Pirates of Silicon Valley (1999)

Rated TV-14

Directed by Martyn Burke, Pirates of Silicon Valley shows the beginnings of Steve Jobs and Bill Gates’ legacies, as they build their technological empires set to dominate the early twenty-first century.

Highlighting their rivalry, the film shows how two entrepreneurs, with widely different philosophies and principles, can help guide each other through a shared competitive drive. 

Both Steve Jobs and Bill Gates might have had similar ideas, but they were oceans apart in how they executed those ideas.

Any entrepreneur should watch this for the reminder that it doesn’t matter if someone copies your idea; it matters what you do with it. Catch it the next time you’re on Netflix!

Erin Brockovich (2000)

Rated R

Directed by Steven Soderbergh, Erin Brockovich shows how even someone down on their luck can rise to a challenge.

While others look down at her for her appearance and personality, Erin rises above them and finds out that a large company is illegally dumping toxic waste and poisoning the surrounding areas. In this classic David and the Goliath setup, Erin goes into the ring and sets up one of the biggest class action lawsuits in American history. 

Any entrepreneur down on their luck and looked down upon should take inspiration from this movie to keep moving forward even when cornered. If you have an account on Peacock or Amazon Prime, check it out ASAP.

Startup.com (2001)

Rated R

The first documentary on this list, Startup.com offers this insight by following GovWorks, a promising start-up that rose quickly before falling just as fast.

In short, the film is about how GovWorks was mismanaged, and how internal power struggles lead to its downfall. In the bigger picture, the film looks at how inflated ideals and dreams of instant wealth became supplanted by harsh economic realities and broken promises.

Any entrepreneur looking to make a change in their business practices by entering a fresh new enterprise, should take note of this cautionary tale. The documentary is available to watch on Tubi and Apple TV.

The Aviator (2004)

Rated PG-13

Directed by Martin Scorsese, this film examines the highs and lows of Howard Hughes’ life. Peeling back the curtain, the film looks beyond Hughes’ luxurious lifestyle and his flings with iconic women, and into how not everything can be fun and games. The film shows that as Hughes grew in success, his battle with depression and phobias only grew larger. 

Any entrepreneur should watch this film—especially those who think success is the key to all their problems, because, quite often, it can be the opposite. Catch this instant classic on Pluto TV, Amazon Prime, or both!

The Pursuit Of Happyness (2006)

Rated PG-13

Even after landing a job as an intern at a prestigious brokerage firm, single father Chris Gardner has nothing but a young son he has to care for. Despite his many hardships, Chris refuses to give in to despair. 

With its touching portrayal of fatherhood and failure, this film is for any entrepreneur trying to make a better life not just for them. Catch it the next time you’re either on Netflix or Amazon Prime.

The Social Network (2010)

Rated PG-13

Directed by David Fincher, The Social Network tells the story of Facebook’s inception. Flashing between Zuckberg and his friends at Harvard creating the controversial website and the litigation between Zukberg and his friend-turned-partner-turned-rival Eduardo Saverin.

Any up-and-coming entrepreneur can take both inspiration and caution from the story of how a college student became the world’s youngest self-made billionaire. Watch it on either Netflix and Hulu.

Steve Jobs (2015)

Rated R

Right beside Pirates of Silicon Valley and The Social Network, is Steve Jobs. Directed by Danny Boyle, the film stars Michael Fassbender as Steve Jobs, giving the audience an in-depth look at three pivotal points in his life.

Through these sequences, Steve Jobs both grows into the iconic figure the public knows him as, and fails to live up to those expectations. 

For any entrepreneur, it’s a reminder that not only can failure happen to anybody at any moment regardless of who you are, but that sometimes success in one area means failing in another. Catch it on Netflix or Amazon Prime when you’re ready.