21 Inspiring Movies Every Entrepreneur Should Watch

Entrepreneurs often seek inspiration to navigate their journeys, and few sources are as powerful as storytelling through film. Movies can inspire, challenge, and push us beyond our limits, which makes them essential companions for anyone on the entrepreneurial path. Whether you’re just starting out or are already entrenched in the business world, here are 21 inspiring movies that every entrepreneur should watch.

1. The Social Network

Directed by David Fincher, this film chronicles the creation of Facebook by Mark Zuckerberg while at Harvard. Sparked by lawsuits and personal conflicts, it highlights how small beginnings can lead to colossal enterprises.

• Why watch it? It illustrates the intersection of ambition, friendship, and business disputes.
• Best Scene: When Zuckerberg meets Sean Parker for the first time.

2. Pirates of Silicon Valley

This movie explores the rivalry between Steve Jobs and Bill Gates, chronicling their journey from fledgling tech enthusiasts to leaders of iconic companies.

• Why watch it? It provides insight into the foundations of two groundbreaking companies and the evolution of technology.
• Best Scene: Steve Jobs interviews a prospective employee at Apple.

3. Startup.com

A documentary about the dot-com bubble, this film follows GovWorks, a startup that crumbled due to internal conflicts and mismanagement.

• Why watch it? It serves as a cautionary tale of how friendships can strain under business pressures.
• Best Scene: Just watch the film to grasp its full impact.

4. Wall Street

This classic features the infamous “Greed is good” speech by Gordon Gekko, played by Michael Douglas. It tells the story of Bud Fox, who becomes embroiled in the darker side of finance.

• Why watch it? It warns against the perils of letting greed dictate decisions.
• Best Scene: Gekko’s compelling speech about the nature of greed.

5. Glengarry Glenn Ross

Starring Al Pacino and Alec Baldwin, this film dives deep into the high-stakes world of real estate sales.

• Why watch it? It exposes the intense pressure and shrewd tactics needed to survive in competitive sales.
• Best Scene: Baldwin’s motivational speech to the sales team.

6. The Big Short

Based on real events, this film showcases the individuals who predicted the 2007-08 financial crisis and profited from it.

• Why watch it? It explains complex financial concepts in an approachable way, emphasizing the importance of foresight.
• Best Scene: When Mark Baum meets a questionable CDO manager.

7. The Wolf of Wall Street

Following the rise and fall of Jordan Belfort, this film highlights the excesses of the finance world.

• Why watch it? It serves as a vivid reminder of what not to become in the entrepreneurial world.
• Best Scene: Matthew McConaughey’s chilling advice on stock brokerage.

8. Boiler Room

Focusing on the shady practices of stock brokerage, this film portrays the drive for wealth and the ethical dilemmas that come with it.

• Why watch it? It illustrates the lure of quick riches in a morally ambiguous industry.
• Best Scene: The chaotic group interview showcasing the cutthroat culture.

9. Fyre: The Greatest Party That Never Happened

This documentary exposes the ill-fated Fyre Festival, a luxurious event promoted through social media that turned into a disaster.

• Why watch it? It highlights the dangers of overpromising and underdelivering in business.
• Best Scene: Andy King’s surprising confession about the festival’s failures.

10. The Aviator

A biopic of Howard Hughes, showcasing his entrepreneurial spirit alongside his struggles with mental health.

• Why watch it? It inspires perseverance against personal and professional challenges.
• Best Scene: The intense Senate hearings that Hughes faces.

11. Moneyball

Billy Beane, the general manager of the Oakland A’s, utilizes sabermetrics to build a competitive baseball team on a budget.

• Why watch it? It illustrates innovative thinking in overcoming limitations, echoing many startup journeys.
• Best Scene: Beane’s breakdown of the team’s problems and finding solutions.

12. The Founder

This film portrays Ray Kroc’s rise to build the McDonald’s empire, focusing on his controversial decisions and business acumen.

• Why watch it? It highlights the complexity and moral ambiguity of franchising.
• Best Scene: Kroc tries his first McDonald’s meal.

13. Margin Call

Set in an investment bank during the early stages of the 2007-08 crisis, this film uncovers corporate greed and poor decision-making.

• Why watch it? It serves as a valuable lesson on ethics in business and the fallout of greed.
• Best Scene: The emergency meeting amongst top partners.

14. Steve Jobs

Featuring Michael Fassbender, this biopic encapsulates key moments of the Apple co-founder’s life.

• Why watch it? The film delves into Jobs’ complexities as a visionary and leader, providing insights into his character.
• Best Scene: Jobs confronting John Sculley about his ouster.

15. Thank You for Smoking

This satire follows Nick Naylor, a spokesperson for Big Tobacco, showcasing the art of persuasion and marketing.

• Why watch it? It illustrates the skill needed to sell anything, no matter how controversial.
• Best Scene: Naylor demonstrates his spin on a talk show.

16. The Pursuit of Happyness

Based on a true story, the film portrays Chris Gardner’s struggle with homelessness while pursuing a career as a stockbroker.

• Why watch it? Gardner’s resilience offers a relatable narrative for many entrepreneurs facing adversity.
• Best Scene: His emotional moment of landing a job.

17. Enron: The Smartest Guys in the Room

This documentary provides an in-depth look at one of the most infamous corporate scandals in history.

• Why watch it? It serves as a stark reminder of the consequences of greed and lack of accountability.
• Best Scene: The examination of the tactics employed by Enron executives.

18. Any Given Sunday

A behind-the-scenes look at a fictional football team explores the dynamics of pressure in competitive sports.

• Why watch it? It demonstrates grit and resilience, valuable traits for any entrepreneur.
• Best Scene: Pacino’s motivational speech before the championship game.

19. The Inventor: Out for Blood in Silicon Valley

This documentary explores the rise and fall of Theranos and its founder, Elizabeth Holmes.

• Why watch it? It showcases the dangers of ambition when driven by deception.
• Best Scene: Watch the film for a comprehensive view.

20. The Great Hack

This documentary reveals the Facebook–Cambridge Analytica scandal, exploring data privacy and ethics in business.

• Why watch it? It raises crucial questions about data ethics in our increasingly digital world.
• Best Scene: The film offers several eye-opening moments about data manipulation.

21. Becoming Warren Buffett

This documentary showcases the life of Warren Buffett, one of the most respected investors in history.

• Why watch it? Buffett’s values and business philosophy serve as an inspiration for entrepreneurs.
• Best Scene: The film provides various insights into Buffett’s life, making it necessary to watch in full.

Watching these films can ignite your passion, offer profound insights, and provide valuable lessons for your entrepreneurial journey. Each film has its unique message, illustrating the complexities, ethics, and challenges entrepreneurs face. Enjoy the cinematic inspiration!