10 Movies Every Entrepreneur Should Watch

This list of ten movies includes some expected, some unexpected, but each with something valuable about unique aspects of building a business, leading a team, and adapting on the fly.

1. The Founder (2016)

Directed by John Lee Hancock
Rated PG-13

There are two key scenes in this adaptation of the true story of the founding of McDonald’s, and they illustrate two completely different ideas about business.

First is the scene where Dick and Mac McDonald explain to Ray Kroc how they had the idea for their new walk-up burger restaurant, and how they optimized it. They drew out their kitchen on a tennis court and had their staff mock a full day of burger making, adjusting and tweaking the layout until they had the perfect flow—burger assembly, sodas, fryers, and milkshakes all arranged so they minimize collisions and get orders to customers in 30 seconds. What they did was innovate and optimize. They saw customer pain points and addressed them head-on.

The second key scene comes later in the film, when Ray Kroc, now attempting to franchise the business at the behest of the McDonald brothers, meets with future business associate Harry Sonnenborn (played by B.J. Novak) who helps Ray have a realization. “You’re not in the burger business. You’re in the real estate business.” Ray Kroc decides in this scene that his business strategy will be at the expense of his partners—and with that, modern McDonald’s was born. Those competing visions of what a business is and how it’s run are fascinating to watch play out. The movie doesn’t really take sides, but it also doesn’t shy away from the realities involved—can you really build a global business with aw-shucks idealism? What’s more important, staying true to your morals and your core brand identity, or adapting, sometimes ruthlessly, in pursuit of profit?

2. The Social Network (2010)

Directed by David Fincher
Rated PG-13

This movie may be one of the best of the last decade. Yes, it’s about the founding of Facebook and the often toxic environment surrounding fast-growing startups. But it’s also really about class, entitlement, privilege, masculinity, and friendship, and how complicated those things all get when wild success changes the equation.

Featuring Jesse Eisenberg as founder Mark Zuckerberg, Andrew Garfield as Eduardo Saverin, Justin Timberlake as Sean Parker, Armie Hammer as twins Cameron and Tyler Winklevoss, and Max Minghella as Divya Narendra, The Social Network presents the founding and subsequent lawsuits at the same time. The main dispute is that the Winklevoss brothers claim that Zuckerberg stole their idea and turned it into Facebook, but the harsh reality is that an idea isn’t really worth all that much. It’s the execution that matters. That’s why the Winklevoss twins ended up settling for $65 million, and today Mark Zuckerberg is worth $121 billion.

Entrepreneurs will be especially interested in all the claims and contracts made, and seek to avoid some of those same mistakes. Choosing business partners is hard. It helps to get everything in writing. Don’t rely on handshake agreements. Not every business is going to be Facebook, but in the high-stakes and litigious world of tech startups and venture capital, it’s better to be safe than sorry.

3. The Dirty Dozen (1967)

Directed by Robert Aldrich
Not Rated

This WWII film is the precursor to Suicide Squad in premise—in this case, twelve convicts in wartime are offered the chance to have their life (or death) sentences commuted if they agree to a near-impossible mission to airdrop into France and kill a gathering of Nazi leaders in a French chateau.

The problem: how do you enforce order in a troop of men with nothing left to lose? The answer is, well, you don’t—so their commanding officer Major Reisman (played by Lee Marvin) has to figure out how to get them to work together as a team, to see their individual success tied up with the success of the mission.

Anyone with experience building a team will find lots to learn: when and how to assert authority, when to pick your battles and let things slide, and how to motivate a team. Major Reisman quickly learns that he’s not going to make progress by acting strictly as an authority figure; he’s going to be fighting alongside his team, sharing in their failures and successes. There’s a lot to be gained here about the value of improvisation, of rolling with the punches and adapting your strategy on the fly. And beyond that, The Dirty Dozen is a lot of fun—which itself is another way this team comes together; even in this group of convicts, murderers, and degenerates, sometimes there’s value in just having fun together.

4. Apollo 13 (1995)

Directed by Ron Howard
Rated PG-13

The vast majority of businesses will never face the unique struggles of going to space. (Although these days, a few actually are.) That doesn’t make the story here any less applicable or less compelling to any business, however small. In 1970, the Apollo 13 mission was meant to be the third manned crew to land on the moon. We know today that never happened.

Astronauts Jim Lovell (played by Tom Hanks), Jack Swigert (Kevin Bacon), and Fred Haise (Bill Paxton) had every intention of being immortalized alongside the other few and proud who got to set foot on the moon. But three days into their journey, an explosion and leak of their fuel cells causes the whole mission to be derailed. The rest of the film details the astronauts’ and mission control’s attempts to bring the spacecraft home safely, when “failure is not an option.”

The key scene in this film is one of team problem-solving. When their oxygen supply dips and temperatures onboard plummet, the two teams separated by hundreds of thousands of miles of empty space must figure out how to fit a square filter onto a round hole in order to save the lives of the three crew members using only what they have on board.

The lessons of teamwork and improvisation in the face of failure are powerful. Not every entrepreneurial roadblock will be a life-and-death situation, but this film shows the value of trusting in your team members’ expertise and working together to find the best solution.

5. Ratatouille (2007)

Directed by Brad Bird
Rated G

Its inclusion here may come as a bit of a surprise, but don’t dismiss it—this isn’t (just) a children’s movie.

“Everyone can cook.” That’s the motto of Chef Gusteau, the (now dead) head of a (formerly) top-of-the-line restaurant in Paris. Remy, a rat, takes that to heart, and when he ends up in Paris with his spectacular nose and tendency to walk upright, he makes the most of it, bringing the restaurant to new heights by operating the cleaning boy from under his hat by pulling on his hair like a marionette.

This animated film directed by Brad Bird may be one of Pixar’s best. Included is an incredibly accurate look at the inner workings of a high-end restaurant, including the specific roles and politics involved in the kitchen. It’s a group of highly dedicated people, each having worked hard to achieve their positions, who don’t take kindly to the arrival of the new wunderkind chef/janitor even before they find out there’s a rat under his toque.

Entrepreneurs will recognize major personality types in the Gusteau kitchen—and smart ones will recognize the potential downfall of any venture, which is illustrated by maniacal head chef Skinner trying to keep a tyrannical grip on what he sees as his kitchen. Failing to recognize talent and trying to claim credit instead of sharing it are common pitfalls for any business. In the kitchen, anyone can cook—even, in this instance, a rat—and in business, talent can and should be cultivated from diverse sources as well. Putting aside prejudices and properly sharing credit and blame where it’s deserved can be great building blocks of an enterprise.

6. The Wolf of Wall Street (2013)

Directed by Martin Scorsese
Rated R

Let’s start off here with a disclaimer. If you’re watching Wolf of Wall Street for business tips, you should probably recalibrate. It’s Martin Scorsese’s interpretation of the true-life memoirs of a truly terrible guy: Jordan Belfort, who pleaded guilty to securities fraud and money laundering in 1999 for his role in running a penny-stock scam. It sounds bleak, but the movie plays like a carnival ride with no dull moments.

Scorsese has a knack for depicting the lives of bad dudes, of people who believe their own lies until it’s too late, and he does it with panache. That translates in this case to an intoxicating first half—the rise part of “rise and fall.” Jordan Belfort, played charmingly by Leonardo DiCaprio, is an ambitious and gifted salesman, and uses that talent to his benefit. He hires a crew of other unscrupulous grifters and they create a stockbroking empire collecting 50% commissions on sales of penny stocks. He used his obscene profits to fuel a lifestyle of drugs, prostitution, greed, and general excess. If you stop the movie there, that sounds pretty great to a lot of terrible people.

But this isn’t a movie about a wildly successful guy getting everything he wants and living happily ever after, despite almost inviting you to think that. This is, with different trappings, another Scorsese mob movie, and justice will come. It helps that we already know the ending. Pay particular attention to the last shot of the film, and make sure you’re not one of the people in Jordan Belfort’s audience, willing to pay real money to hear advice from someone you should never take advice from.

Sure, you could probably learn some sales tactics from this film, but really it’s a pretty clear depiction of what not to do: don’t commit fraud; don’t make your enterprise more important than your personal life; don’t do drugs; don’t be intoxicated by money at the expense of the law; don’t work with people who remind you of Jordan Belfort. It’ll end badly.

7. Molly’s Game (2017)

Directed by Aaron Sorkin
Rated R

The business being built here is an empire of high-stakes poker nights run by Molly Bloom, former Olympic skier, played by Jessica Chastain in this true story adaptation. We get the background of the poker game she set up, framed by the present-day reality of the consequences of running the game—she’s been indicted as part of an investigation into the Russian mob. As she works with her lawyer (Idris Elba) to present her case and protect her dignity, we learn how she went from winter sports to having dirt on celebrities, world leaders, and mafia members.

It’s unlikely anyone reading this ebook is looking for tips on how to start up an international high-class high-stakes gambling ring, but any entrepreneur could gather some valuable tips from this story by applying it to their own business. The biggest theme here is Molly’s almost pathological desire to keep control without showing force, and part of the way she does that early in the film is by recognizing when it’s time to end her partnership. When faced with an impossible deal and an unlivable working situation from her skeezy boss (played by Jeremy Strong), she strikes out on her own, taking all the clients with her. Depending on what perspective you take, there are some important lessons here:

First, don’t be difficult to work with, especially if you’re running an illegal business. You’re just asking for trouble. Second, don’t give leverage to the wrong people; always make sure you trust your business partners. Third, never get involved in the Russian mob. They’re just bad news.

8. Joy (2015)

Directed by David O. Russell
Rated PG-13

Joy Mangano, the real-life inventor and genius saleswoman, is the subject of this feature, played in an Oscar-nominated role by Jennifer Lawrence. In 1990, faced with a variety of family and personal setbacks, Joy gets frustrated at a simple, everyday domestic task—mopping. In something so practical and quotidian she finds an opportunity. She creates the Miracle Mop, a self-wringing mop that can be wrung out without getting your hands wet and dirty. But as any inventor or consumer product entrepreneur knows, that’s just the beginning.

Selling a product is completely different from creating one, and that’s where this movie shows the reality—manufacturing, patents, licensing, and litigation, not to mention the people trying to rip Joy off at every turn. But what makes this movie special is when Joy takes things into her own hands. She knows best what makes her product great, and when she convinces the people at QVC to allow her to demonstrate it herself, she sells 18,000 mops in half an hour.

Since then, Joy Mangano has turned creating consumer goods into an enormous empire selling hundreds of millions of dollars of practical everyday products. Anyone in the consumer product space can find something to learn from—and maybe something to commiserate within this true success story.

9. Moneyball (2011)

Directed by Bennett Miller
Rated PG-13

Moneyball, the true story of the team that changed baseball recruiting forever, also happens to be the third film on our list written by Aaron Sorkin. The reality of pro sports is that there are big markets and small markets—ones with huge budgets for recruiting, facilities, and so forth, and others with less of all of that, who have to figure out how to make do and compete on the same scale with drastically less money. That might be a familiar obstacle to many entrepreneurs—how do I build a winning business when my competitors can outspend me in every way?

For Billy Beane, general manager of the Oakland Athletics (played by Brad Pitt), that problem is his reality. Until he meets a young Yale graduate in economics, played by Jonah Hill, who has a new statistics-based idea on how to properly value players. Throwing out all conventional knowledge including scouting reports, Billy Beane decides to focus on the one stat that actually leads to runs, and wins—on-base percentage. Doing that allows the A’s to acquire overlooked talent for cheap. Despite some headaches and some resistance from the coaching staff, it works—and the A’s start winning.

Since then, the Moneyball method has become standard not just in baseball but across sports. And business leaders can gain something from it too. What is the one stat that matters in your industry? How do you focus on that? How do you retain talent, and let go of things that may be holding you back? Those are complicated questions, but worth examining.

10. The Big Short (2015)

Directed by Adam McKay
Rated R

This film is a comedy that’s designed to make you mad. Heavily inspired by The Wolf of Wall Street, The Big Short does a great job of explaining the circumstances surrounding and leading up to the housing market crash and the Great Recession of 2008. It’s presented at a breakneck pace, taking little pauses to break the fourth wall so celebrities (like Margot Robbie in a bathtub, or Anthony Bourdain not in a bathtub) can explain complicated financial concepts to the audience.

The big short referred to is a bet made by investors who foresaw the coming crash. Instead of crashing with the rest of them, they shorted the housing market—and ended up increasing their investment fund by billions.

The movie will have you asking several questions—mostly, why is this legal? And: why is everyone wearing a bad wig? Hairstyles aside, The Big Short is an enlightening and energetic film that brings light on a poorly understood subject that had far-reaching consequences around the world of economics, politics, and more. Whatever your industry, you’ll be able to share in the frustration of corruption at the highest levels and avoid some of the same mistakes.

Additional Entrepreneurial Movies and TV Shows

If that’s not enough, here are a few more movie and TV suggestions. They’re all either about entrepreneurs or have valuable lessons for running a business, working as a team, or taking advantage of once-in-a-lifetime opportunities.

• The Outlaw Josey Wales (Directed by Clint Eastwood, 1976) – A man on the run for a crime of revenge can’t help but fall in with a band of unlikely outcasts.
• The Pursuit of Happyness (Directed by Gabriele Muccino, 2006) – A struggling salesman takes custody of his son as he’s poised to begin a life-changing professional career.
• Rocky (Directed by John G. Avildsen, 1976) – A near-nobody from Philly gets a chance at the heavyweight boxing championship, and the chance to mean something to himself.
• Citizen Kane (Orson Welles, 1941) – The rise and fall of a newspaper magnate loosely based on the media giants of the early 20th century.
• It’s a Wonderful Life (Frank Capra, 1946) – A young man redefines what his life means as he tries to save his town from a greedy real estate kingpin.
• The Devil Wears Prada (David Frankel, 2006) – A woman learns what it takes to survive in the cutthroat world of high fashion.
• Breaking Bad (5 seasons) – A high school chemistry teacher and his former student create a drug empire from scratch.