10 Must-Watch Movies for Entrepreneurs: Stories of Ambition, Risk, and Success

Entrepreneurship isn’t just about building a business—it’s about crafting a story, chasing a vision, and fighting through every obstacle that stands in the way. It’s about risk, triumph, failure, and finding the courage to start again. Movies have a unique way of capturing these moments, blending the thrill of ambition with the humanity of the people who dare to dream big.

These ten movies aren’t just for entertainment; they’re for reflection. They are windows into the grit, creativity, and relentless drive it takes to make it to the top. Every entrepreneur can find a piece of themselves in these stories, from the excitement of the first spark of an idea to the quiet moments of doubt that demand perseverance.

1. The Wolf of Wall Street (2013)

Few films capture the raw energy of ambition like this one. Jordan Belfort’s rise as a stockbroker is a whirlwind of persuasion, charm, and unstoppable drive. He doesn’t just sell—he electrifies. Every deal he closes is a step closer to the empire he envisions and he goes on a high figuratively and literally. But as his world grows, it becomes clear that success built on excess and dishonesty comes at a cost and can make you lose yourself. The passion of Jordan Belfort’s story is one that is moving but also heartbreaking, it shows the downfall of excess of a good thing.

For entrepreneurs, this film is a rollercoaster of inspiration and caution. Belfort’s charisma and belief in his own vision show the power of confidence, but his story also warns of the dangers of losing sight of what matters most. It’s a vibrant, unrelenting reminder that how you achieve success is as important as achieving it. It also showcases how empires can quickly rise and just like that — quickly crumble.

Why Watch:

• Learn the art of persuasion and the importance of self-belief.
• Reflect on the balance between ambition and ethics.
• It’s an unforgettable, electrifying ride through the highs and lows of business.

2. The Social Network (2010)

This film is more than a story about Facebook’s creation; it’s a raw and complex tale of vision and ambition colliding with human flaws. Mark Zuckerberg’s journey from a Harvard dorm room to creating one of the world’s most influential companies is both inspiring and unsettling. His ability to see what others couldn’t—how people connect—changed the world.

For entrepreneurs, “The Social Network” is a study in how ideas evolve, how partnerships can fracture, and how relentless focus can lead to both triumph and isolation. It shows the brilliance of innovation but doesn’t shy away from the personal cost of striving for greatness.

Why Watch:

• Witness the power of turning a simple idea into a global phenomenon.
• Reflect on how success can test relationships and loyalty.
• It’s a sharp, thought-provoking exploration of ambition.

3. Moneyball (2011)

“Moneyball” isn’t just about baseball; it’s about changing the game entirely. Billy Beane, the Oakland A’s general manager, sees potential where no one else does, using data and strategy to defy the odds. He faces ridicule, pushback, and doubt, but his belief in his unconventional approach never wavers.

For entrepreneurs, this film is a testament to the power of seeing opportunity where others see limitations. It’s a story about taking risks, breaking the rules, and trusting your instincts even when the world says you’re wrong.

Why Watch:

• Learn how innovation thrives when you challenge the status quo.
• Find inspiration in resilience against doubt and criticism.
• A reminder that creativity often emerges from constraints.

4. The Pursuit of Happyness (2006)

This heart-wrenching story follows Chris Gardner, a man who refuses to give up on his dreams despite overwhelming odds. Homeless and struggling, he takes an unpaid internship at a brokerage firm, working tirelessly to create a better life for himself and his son.

For entrepreneurs, “The Pursuit of Happyness” is the ultimate lesson in grit and perseverance. It shows that success isn’t always about talent or luck—it’s about resilience, the willingness to fail, and the strength to keep going no matter what.

Why Watch:

• A reminder that perseverance and hard work can overcome any obstacle.
• Highlights the personal sacrifices often required to chase a dream.
• An emotional journey that will reignite your determination.

5. Steve Jobs (2015)

This biopic takes an intimate look at the life of one of the most influential entrepreneurs in modern history. Steve Jobs wasn’t just a tech innovator—he was a visionary who pushed boundaries and demanded excellence at every turn. But the film doesn’t shy away from his flaws, exploring the complexities of his relationships and his relentless pursuit of perfection.

For entrepreneurs, “Steve Jobs” is an exploration of leadership, creativity, and the cost of greatness. It shows the brilliance of his vision and the personal challenges that came with it, offering valuable lessons about what it takes to turn bold ideas into reality.

Why Watch:

• Discover the balance between vision and execution.
• Reflect on how leadership challenges relationships.
• An inspiring story of turning innovation into legacy.

6. The Big Short (2015)

This sharp and satirical film dives into the financial world, chronicling the outsiders who predicted the 2008 housing market crash. It’s a story of seeing what others ignored, taking risks, and standing by your convictions even when the world doubts you.

For entrepreneurs, “The Big Short” is a reminder of the importance of critical thinking and the ability to see opportunities where others see chaos. It’s as much about resilience as it is about foresight.

Why Watch:

• A lesson in spotting opportunities in unexpected places.
• Shows the importance of research, strategy, and conviction.
• Balances humor with hard-hitting truths about risk and reward.

7. Joy (2015)

“Joy” follows the journey of Joy Mangano, a struggling single mother who becomes a self-made millionaire through sheer determination and creativity. Her story is one of resilience, resourcefulness, and the courage to pursue an idea despite countless setbacks.

For entrepreneurs, this film is a celebration of innovation and grit. It’s a story about believing in your own potential even when the odds are stacked against you.

Why Watch:

• A testament to the power of persistence and ingenuity.
• Highlights the challenges of breaking through in competitive industries.
• A moving story of triumph against the odds.

8. Boiler Room (2000)

“Boiler Room” is a gripping look at the high-stakes world of stockbroking, following a young broker tempted by the promise of fast money. It’s a cautionary tale about the dangers of chasing success without considering the ethical consequences.

For entrepreneurs, it’s a reminder that building something meaningful requires more than ambition—it requires integrity.

Why Watch:

• Reflect on the importance of values in the pursuit of success.
• A stark look at the allure and risks of high-reward ventures.
• Offers insight into the dark side of salesmanship and ambition.

9. You’ve Got Mail (1998)

On the surface, “You’ve Got Mail” is a charming romantic comedy, but beneath its lighthearted exterior is a compelling tale of business and competition. It follows two bookstore owners—one running a small independent shop, the other a corporate chain—as they navigate rivalry and change in their industry.

For entrepreneurs, it’s a thoughtful exploration of adapting to disruption, balancing personal values with business realities, and finding ways to thrive in a changing landscape.

Why Watch:

• A heartfelt story of competition and reinvention.
• Highlights the importance of adapting to market changes.
• Shows the human side of business, blending strategy with emotion.

10. Erin Brockovich (2000)

Erin Brockovich’s story is one of relentless determination and advocacy. As a legal assistant, she takes on a powerful corporation polluting a town’s water supply, fighting for justice despite overwhelming odds.

For entrepreneurs, it’s a reminder that business isn’t just about profit—it’s about making a difference. Her resourcefulness, grit, and belief in her mission show that even the smallest voice can spark meaningful change. It is also an inspiring movie for businesswomen as it shows that the journey Brockovich went through to gain respect in the corporate world.

Why Watch:

• A powerful story of resilience and purpose.
• A reminder that businesses can drive social good.
• Inspires the courage to stand up for what matters.

Honorable Mention: American Psycho (2000)

This dark and unsettling film dives into the culture of the corporate elite during the height of yuppie materialism. "American Psycho" explores the competitive, status-driven world of 1980s Wall Street, where success is measured by wealth, appearances, and the superficial trappings of power. From the obsession with designer suits to the infamous scene comparing business cards, the film critiques the hollow ambition of a culture focused on image over substance.

For entrepreneurs, the film serves as both a cautionary tale and a biting satire of the dangers of valuing material success over meaning. It’s not just a thriller—it’s a lens on the darker sides of business culture, the need to "one-up" peers, and the personal cost of chasing status at any price.

Why Watch:

• Offers a sharp critique of materialism and corporate superficiality.
• Explores the cutthroat competitiveness of yuppie culture.
• A satirical take on the emptiness of defining success through appearances.

These movies pull back the curtain on the worlds of business, ambition, and innovation, showing the thrill, the drama, and the human stories behind great ideas. They highlight the power of strategy, the art of negotiation, and the complexities of success in ways that inspire and challenge. For anyone passionate about the intersection of creativity and business, these films are essential viewing, offering new perspectives with every watch.