Films about business that offer valuable lessons for entrepreneurs

1. The Big Short (2015)

The Big Short (Paramount Pictures, 2015)

There are a lot of lessons for bankers to take from The Big Short, Adam McKay’s retelling of the 2008 financial crisis. For example, how to dupe customers or dodge a criminal conviction. But for entrepreneurs, the character of Steve Carrell acts as the real inspo.

When they see the mortgage bonds being flogged by the big banks, Carrell’s band of merry hedge fund managers smell snake oil, and head out into the field to see for themselves.

Based on what they find, they bet against the housing market and become some of the few individuals to profit from the downturn, rather than lose. In short, not all decisions can be made at your desk. Going to the front lines can generate invaluable customer insights.

2. Blackberry (2023)

Blackberry (Elevation Pictures, 2023)

What happens when you take a bunch of computer geeks and make them cross paths with a hungry investment banker? The answer is a world-leading communications company that underwent perhaps one of the most dramatic rises and falls of the past 100 years.

Blackberry explores what caused the phone company’s downfall. It has many takeaways on business strategy and R&D, but perhaps the biggest lesson is how vital competitor analysis can be. When Apple comes to town with the new iPhone, Blackberry quickly starts to rot.

3. The Social Network (2010)

The Social Network (Columbia Pictures, 2010)

The Social Network should be compulsory watching for any wannabe entrepreneur. Documenting Mark Zuckerberg’s invention of the founding father of social media, Facebook, it is an important tale about the importance of having a supportive network in business.

As Facebook’s user numbers rise, Zuckerberg’s friend list dwindles, until he’s left without a business partner and facing several lawsuits. Far from an inspiring watch, this is a reminder that the ‘lone wolf’ founder is a myth, and to choose your mentors wisely.

4. Glengarry Glen Ross

Glengarry Glen Ross (New Line Cinema, 1992)

Even if you’re not in a sales business, entrepreneurs will need to learn the tricks of the trade. Glengarry Glen Ross tells the story of three salesmen in a market culture who employ underhanded business tactics to outsell each other, while working under the threat of layoffs.

Richard Roma is the star of the floor, and for good reason. He does the work to understand his customer’s needs, doubts, and pain points (which he then exploits). It’s by listening to the voice of the customer that Roma succeeds at his boss’ instruction to “always be closing”.

5. The Devil Wears Prada (2006)

The Devil Wears Prada (20th Century Fox, 2006)

Before this fashion favourite came out, critics assumed it would be a slam piece on Anna Wintour, the editor of Vogue and rumoured inspiration for the lead character, Miranda Priestly. What emerged instead was a sympathetic portrayal of what it takes to be a leader.

Priestly is equally respected and feared. She’s cutthroat, authoritarian, and expects only the best. Her character arc paints a realistic picture of what it’s like to be a woman in business, and the, sometimes unpopular, leadership decisions that successful CEOs must make.

6. Office Space (1999)

Office Space (20th Century Fox, 1999)

Mike Judge’s cult classic Office Space satirises almost every aspect of the modern corporate office, from stress-inducing commutes to micromanaging co-workers. It’s a cautionary tale for employers about why you need organisational culture to motivate staff members.

Working for a company with no vision results in the washed-up workforce at Judge’s nondescript office building feeling unmotivated and bored. Create a positive environment to get people up and excited to go to work. And, preferably, leave the grey cubicles in the 90s.

7. Wall Street

Wall Street (American Entertainment Partners Amercent Films, 1987)

Bud Fox is a young stockbroker who becomes involved with Gordon Gekko, a wealthy, unscrupulous corporate raider. Their relationship anchors Wall Street, an apologue about the dangers of excess, and how a competitive, win-or-else ethos poisons the workplace.

Under Gekko’s watch, a toxic work culture turns Fox from an eager new starter into a manipulative egoist willing to betray his colleagues. It’s a great lesson in the power that leaders can have, and why hiring right is particularly essential for management roles.

8. Chef (2014)

Chef (Open Road Films, 2014)

Many films on this list focus on the big. They feature New York office buildings and loud-mouthed stockbrokers. Chef takes a humbler route, telling the story of an unhappy head chef who decides to open his own food truck to rediscover his love of cooking.

Chef can almost be an instructional video on launching a street food business. While it might be unbelievable at times (a viral marketing campaign happens almost every minute in this film), it’s ultimately a heartwarming depiction of the journey from idea to startup.

9. Air (2023)

Air (Amazon Studios, 2023)

Air follows shoe salesman Sonny Vaccaro, and how he convinced Nike to secure a winning partnership with a newbie basketballer named Michael Jordan. It’s a master class in sales and marketing, but its mantra is simple: when starting a business, you have to go all in.

Despite Nike insisting that Jordan wasn’t going to be a star, superfan Vaccaro stuck to his guns. He was willing to put his career on the three-point line for Jordan, showing a staggering level of commitment and self-belief that entrepreneurs need to get off the ground.

10. Up in the Air (2009)

Up in the Air (Paramount Pictures, 2009)

This lesser-known business film tells the story of a travelling corporate “downsizer” played by George Clooney, who flies around the USA firing staff on behalf of corporations. Until a green trainee named Natalie suggests doing it via video conferencing (this was in 2009).

Up in the Air has many important takeaways for HR managers. Chiefly, in an age of AI, technology can’t fully replace human connections in customer service. Natalie is unprepared for the impact of her robotic redundancy technique, and it ultimately leads to disaster.

11. Jerry Maguire (1996)

Jerry Maguire (Sony Pictures, 1996)

Centring on a young Tom Cruise as a jaded sports agent who is looking for meaning in his work. Known for giving us such iconic, quotable lines as “show me the money” and “you had me at hello”, it is also chock-a-block with manager lessons on the importance of integrity.

Jerry’s decision to write a mission statement advocating a more personal approach to management means he chooses people over profit. It’s a lesson in staying true to your core values as an entrepreneur, and cultivating meaningful client relationships built on trust.

12. Baby Boom (1987)

Baby Boom (United Artists, 1987)

On the face of it, Baby Boom should be just another bad 80s comedy. Diane Keaton’s yuppie leading lady gets lumped with her dead sister’s baby, who she then has to look after while balancing a high-flying office job. Shoulder pads and brick phones at the ready, folks.

But Baby Boom’s underlying theme is about the difficulties of being a working parent, and the hard choices that (usually women) are forced to make when choosing between a career and childcare. It might be thirty years old, but as Keaton’s character struggles to achieve work-life balance without flexible working, its message will chime with mums and dads today.

13. Boiling Point (2021)

Boiling Point (Ascendant Films Burton Fox, 2021)

Boiling Point serves up a plate of exposure therapy for anyone who has ever worked or run a busy restaurant. Filmed in real-time, it follows Andy Jones (played by a profusely sweaty Stephen Graham) who is Head Chef of Jones & Sons, an upmarket restaurant in London.

It’s a claustrophobic, anxiety-inducing 92 minutes filled with lessons on what not to do when you’re running a silver service establishment. In order: don’t overbook your tables, don’t forget about food safety regulations, and don’t start snorting pills in the back office mid-shift.

14. Joy (2015)

Joy (20th Century Fox, 2015)

You probably haven’t heard of Joy Mangano, a self-made millionaire who created her own empire. But you’ve likely heard of her invention, the miracle mop. The film tells her story from struggling airline worker, to bankruptcy, to successful independent business woman.

Starting a company is not without hurdles, and the film doesn’t shy away from showing them. But despite a catastrophic first product launch, and various personal setbacks, Joy handles failure like a seasoned entrepreneur should: take responsibility, learn, and don’t give up.

Inspired to start your own business? Check out our list of over 100, Oscar-worthy small business ideas.