Skip to Content

Lights, Camera, Entrepreneurship 15 Movies to Inspire Your Inner CEO

Lights, Camera, Entrepreneurship 15 Movies to Inspire Your Inner CEO

Telling business owners to take time away from their venture to watch the best entrepreneurship movies ever made isn’t easy.

Entrepreneurs commonly have trouble taking time away from work to just veg. I almost always feel behind, overwhelmed, or inspired to just keep pushing forward.

But, taking time to recharge and unplug has unintended consequences. Sometimes giving yourself space away from a project helps you gain clarity on how to do something better.

I have to force myself to put my laptop away and be present in the moment. Some of my best work has come after I took intentional breaks and let myself become more inspired from others success.

Skip to:

best entrepreneurship movies that inspires

What Makes a Great Entrepreneurship Movie

When you’re looking for the best entrepreneurship movies, you’re essentially on the hunt for films that do more than just entertain. They should inspire and resonate with your entrepreneurial spirit. I will break down the key elements that make for a compelling entrepreneurship movie.

True Stories and the American Dream

It’s often the movies based on a true story that tug at your ambitions. These films showcase real-life challenges and triumphs, giving you a raw look into the highs and lows of the business world. They capture the essence of the American Dream, where hard work and luck can lead to success.

Inspiration Meets Cautionary Tale

Great entrepreneurship movies strike a balance between being inspirational movies and serving as a cautionary tale. They ignite your drive to innovate, while also reminding you of the potential pitfalls. You’re likely to see characters who battle adversity and come out stronger, showing you that perseverance is key.

Reflecting the Business World

Above all, the best films about entrepreneurship give you a peek into the complexities of the business world. They highlight strategic decision-making, the importance of relationships, and the innovative thinking that’s essential for success. These movies aren’t just about making money but they are also about creating value and impact.

watching entrepreneurship movies

Top 15 Best Entrepreneurship Movies

Exploring the journeys of successful entrepreneurs can inspire and inform your own path in the business world. This list of best entrepreneurship movies features stories of determination, innovation, and the challenges of building a business.

1. The Social Network

“The Social Network” is a compelling narrative directed by David Fincher that presents the tumultuous inception of Facebook. Witness Mark Zuckerberg, portrayed by Jesse Eisenberg, evolve from a Harvard student into one of the most influential tech entrepreneurs, creating a social networking revolution. This film tracks the intense complexity and legal battles within the tech industry.

Overview: Chronicles Mark Zuckerberg’s journey from college student to CEO of Facebook.

Key Lessons: The importance of innovation, the complexities of business partnerships, and navigating legal challenges.

Why Watch: Insight into the rapid evolution of a tech giant and the real-life challenges faced in the startup world.

2. Steve Jobs

In “Steve Jobs,” you’ll observe the intense portrayal of Apple’s cofounder by Michael Fassbender. This film takes you backstage into the innovative mind of Steve Jobs during the launch of groundbreaking products, peeling back the layers of his complex character.

Overview: Focuses on the professional life of Steve Jobs, highlighting his role in revolutionizing the tech industry.

Key Lessons: The significance of vision, perseverance, and product innovation.

Why Watch: Offers a look at the relentless drive and passion of one of the tech industry’s most influential figures.

3. The Founder

“The Founder” explores the true story of Ray Kroc, played by Michael Keaton, a struggling salesman who transformed a small eatery owned by the McDonald brothers into the fast food giant McDonald’s. Through persistence and ambition, Kroc redefined the food industry.

Overview: Depicts Ray Kroc’s transformation of McDonald’s from a single restaurant to a global franchise.

Key Lessons: The power of scalability, branding, and strategic business thinking.

Why Watch: A compelling story of ambition, persistence, and the darker side of entrepreneurial success.

4. Moneyball

Brad Pitt stars as Billy Beane in “Moneyball,” where a sports agent challenges traditional baseball recruitment strategies to build a winning team. This real-life adaptation demonstrates that second chances can lead to unprecedented success.

Overview: Tells the story of how Billy Beane used statistical analysis to assemble a competitive baseball team.

Key Lessons: The value of innovation, data-driven decisions, and challenging traditional methods.

Why Watch: Shows how unconventional thinking can lead to success, even with limited resources.

entrepreneurship movies to learn

5. The Wolf of Wall Street

Dive into the extravagant life and true story of Jordan Belfort in Martin Scorsese’s “The Wolf of Wall Street.” Leonardo DiCaprio’s portrayal underscores the highs and lows of Belfort’s journey through wealth, fraud, and the federal government’s scrutiny.

Overview: Follows the rise and fall of stockbroker Jordan Belfort, highlighting the excesses and corruption in finance.

Key Lessons: Ethics in business, the consequences of greed, and the importance of regulatory compliance.

Why Watch: A cautionary tale about the intoxicating effects of power and money.

6. The Big Short

“The Big Short” tells the gripping story of the 2008 financial crisis, focusing on the housing market’s collapse. Christian Bale and an ensemble cast bring to life the characters from Michael Lewis’ book, navigating through one of the darkest times in financial history.

Overview: Explores the build-up of the housing and credit bubble leading to the financial crisis of 2008.

Key Lessons: Critical thinking, skepticism in investing, and understanding financial markets.

Why Watch: Provides an educational perspective on the financial crisis, making complex concepts accessible.

7. Jerry Maguire

Tom Cruise is a sports agent with integrity in Jerry Maguire, striving to succeed under the mantra, “Show me the money!”

Overview: A sports agent finds his moral compass and seeks success with a new business model.

Key Lessons: The importance of honesty, integrity, and personal relationships in business.

Why Watch: Combines the world of sports with business, offering lessons on loyalty and value.

8. The Aviator

Leonardo DiCaprio plays Howard Hughes in The Aviator, a film about the aviation pioneer and film director’s career and personal struggles.

Overview: Chronicles the life of Howard Hughes, focusing on his aviation and film achievements.

Key Lessons: Dealing with competition, the drive for perfection, and managing personal demons.

Why Watch: Highlights innovation and the challenges of pioneering in uncharted territories.

9. Wall Street

Michael Douglas’s iconic role in Wall Street as Gordon Gekko coined the phrase, “Greed is good,” highlighting the excesses of the financial industry.

Overview: A young stockbroker gets involved with a wealthy, unscrupulous investor.

Key Lessons: Moral integrity, the allure of quick success, and the ethical dilemmas of the business world.

Why Watch: A classic film that examines the greed and excess of Wall Street.

Free Stocks on Webull

10. Boiler Room

Boiler Room is a 2000 film that throws you right into the aggressive world of brokerage firms. With its main character caught in a moral crisis, it depicts the gritty reality of telesales and the desperation to succeed at any cost. It’s a compelling watch that offers cautionary tales about the darker sides of entrepreneurial ambition.

Overview: A college dropout gets a fast-paced job in an investment firm, leading to moral conflicts.

Key Lessons: Ethics, the realities of high-pressure sales environments, and personal integrity.

Why Watch: Provides a glimpse into the high stakes and pressures of the investment world.

11. The Pursuit of Happyness

Will Smith delivers a moving performance in The Pursuit of Happyness, a tale of a struggling salesman’s journey to becoming a successful business owner.

Overview: A true story of a struggling salesman who becomes a successful stockbroker.

Key Lessons: Perseverance, the impact of personal drive, and the pursuit of happiness.

Why Watch: An inspirational tale showcasing the challenges and rewards of relentless effort and optimism.

watching wall street

12. Glengarry Glen Ross

Based on an award-winning play, Glengarry Glen Ross showcases a gripping tale of real estate agents involved in unscrupulous business practices. Featuring an iconic performance by Alec Baldwin and Jack Lemmon, this film serves as a stark reminder of the ethical dilemmas one may face in the pursuit of success. It’s a must-watch for insights into the high-pressure tactics used in sales and the impact of corporate greed on personal integrity..

Overview: Focuses on four real estate agents participating in a sales competition.

Key Lessons: Sales tactics, the harsh realities of a competitive workplace, and the human side of business.

Why Watch: An intense look at the pressures of sales and the lengths people will go to succeed.

13. The Devil Wears Prada

Meryl Streep and Anne Hathaway star in The Devil Wears Prada, revealing the harsh realities of the fashion industry and corporate world.

Overview: A young woman lands a job as an assistant to a powerful fashion magazine editor.

Key Lessons: Work-life balance, career aspirations, and navigating the workplace hierarchy.

Why Watch: Reveals the demanding nature of the fashion industry and corporate life.

14. Office Space

Office Space is a satirical look at the mundane life within a typical office, offering a comedic take on the workday and corporate culture.

Overview: A comedic take on the monotonous, frustrating life of office workers.

Key Lessons: The importance of job satisfaction, creativity, and breaking free from mundane routines.

Why Watch: Offers a humorous perspective on office culture and the desire for more meaningful work.

Fun Fact: This is the movie that inspired me to pursue enough wealth to do nothing.

Peter Gibbons: What would you do if you had a million dollars?

Lawrence: I’ll tell you what I’d do, man: two chicks at the same time, man.

[Peter laughs and then notices Lawrence’s dead serious expression]

Peter Gibbons: That’s it? If you had a million dollars, you’d do two chicks at the same time?

Lawrence: Damn straight. I always wanted to do that, man. And I think if I were a millionaire I could hook that up, too; ’cause chicks dig dudes with money.

Peter Gibbons: Well, not all chicks.

Lawrence: Well, the type of chicks that’d double up on a dude like me do.

Peter Gibbons: Good point.

Lawrence: Well, what about you now? What would you do?

Peter Gibbons: Besides two chicks at the same time?

Lawrence: Well, yeah.

Peter Gibbons: Nothing.

Lawrence: Nothing, huh?

Peter Gibbons: I would relax… I would sit on my ass all day… I would do nothing.

Lawrence: Well, you don’t need a million dollars to do nothing, man. Take a look at my cousin: he’s broke, don’t do shit.

Office Space Dialogue Courtesy of IMDB

15. Pirates of Silicon Valley

This film charts the early rivalry and entrepreneurship of tech giants Apple and Microsoft, featuring the startup founders’ struggles and successes.

Overview: Traces the early competition between Steve Jobs (Apple) and Bill Gates (Microsoft).

Key Lessons: Innovation, competition, and the birth of the personal computer era.

Why Watch: Provides a historical look at the rivalry that shaped the tech industry.

friends are watching together

What Can We Learn from These Movies

Entrepreneurship often seems like a rollercoaster of trials and triumphs. The best entrepreneurship movies reflect the reality of starting and running your own business, offering both inspiration and hard-earned lessons. Watching these movies, you can gain insights into business acumen, the virtues of hard work, and the varied pathways to success.

True stories are particularly compelling, as they showcase real struggles and victories of startup founders. For instance, “Joy” tells the tale of a determined entrepreneur who turns a simple idea into a successful enterprise. Learn from her perseverance, and understand that success often means overcoming significant obstacles.

Here’s what else these films teach you:

  • Hard Work and Determination – They often highlight that the best way forward involves resilience.
  • Business Acumen – Characters exhibit sharpness in understanding and dealing with a business situation effectively.
  • Startup Founders – Portrayals of founders capture the essence of driving a concept to fruition, despite facing skepticism and financial hurdles.

By watching these narratives unfold, you equip yourself with a sensory learning experience. You witness what it takes to build and run a business, the challenges you may encounter, and the dedication required to persevere. Embed these lessons into your approach, and let them guide your own entrepreneurial journey.

Also read:

How to Use These Movies for Your Entrepreneurial Journey

When you watch the best entrepreneurship movies, it’s not just for entertainment. These films can be powerful tools to inspire and educate you on your entrepreneurial path. Consider these movies as case studies. Observe the challenges faced by characters and take note of the innovative solutions they implement.

loading your favorite movie

Reflect on Their Strategies

Identify the core strategies and business principles displayed in the films. Think about how these insights apply to your own business and where you could make improvements.

  • Inspiration – Allow the success and determination displayed to motivate you as an entrepreneur.
  • Learning from Mistakes – Notice the critical errors made by characters and plan how to avoid similar pitfalls.

Engage with Fellow Entrepreneurs

Discuss the movies with fellow entrepreneurs. Insights and viewpoints from diverse backgrounds can deepen your understanding and expose you to new ideas.

  • Networking – Use these discussions as networking opportunities to foster relationships.
  • Resourcefulness – Sharing experiences can lead to creative, resourceful approaches to business.

Take Action

After watching and reflecting on these inspiring movies, take actionable steps. Create a plan that incorporates your new insights to become a better entrepreneur.

  • Goal-Setting – Set clear, achievable goals based on the lessons learned.
  • Implementation – Apply the strategies to your business and monitor the results.

Remember, these films are more than entertainment. They are a catalyst for growth. Let them guide you to new heights in your entrepreneurial journey.

Taking Action Beyond Inspiration

After watching the best entrepreneurship movies, you may feel a wave of inspiration washing over you. In that case, harness the energy and channel it into taking concrete steps. These films often showcase success stories, but remember, the protagonists found a better way to navigate the often complicated world of big companies and emerged as the smartest guys in the room.

Real life is not a screenplay, and your journey will be unique. Take cues from these films to learn resilience and the importance of innovation. Translate the struggles and triumphs you see on screen into actionable plans for your own ventures. Keep the narratives of these movies in your arsenal as a motivational tool when you face challenges.

Remember, success stories in entrepreneurship are not just about the eureka moments but they are also about persistence. As you witness in these films, taking action means constantly seeking a better way to approach problems, never resting on your laurels, and striving for growth. Your real-life success story starts with action and persistence, drawing from the lessons taught by some of the smartest minds in business.

take action beyond inspiration

Transforming Inspiration into Entrepreneurial Triumph

Resist the urge to compare your journey to any of the stories in these films. Instead, use their success or failure as motivation for pursuing your own path.

Also realize there is more to the story than what is depicted on screen. Elements are always left out for clarity. And those details may be why you think they had it easy or would change your perspective on decisions they made.

Let these cinematic experiences embolden you and guide your path to success. These films are a source of motivation and a catalyst for innovation. Your entrepreneurial education is complemented by the powerful stories these movies tell.

No Title

No Description

No Title

No Description

FAQ: Best Entrepreneurship Movies


  • Veronica Hanson

    Veronica Hanson blogs from whatever country she happens to be in at the time, currently she's hanging out in Japan. She's been living as a nomad remote entrepreneur with her family since 2020.

    View all posts

Leave a comment

Your email address will not be published. Required fields are marked *

CommentLuv badge