Reel Leadership: Iconic Movies That Teach Entrepreneurship and Success

By Karry Kleeman
3x SaaS Exited CRO | Board Member | Investor | Advisor | GTM Executive

Great leaders and entrepreneurs find inspiration in many places—books, mentors, experiences, and yes, even movies. Films have a unique way of conveying powerful messages about vision, perseverance, and resilience. The best leadership and entrepreneurial stories aren’t just entertaining; they ignite something within us, urging us to think bigger, act bolder, and lead with purpose.

As someone who thrives at the intersection of business growth and human connection, I’ve always found that movies are more than just entertainment—they are masterclasses in leadership, innovation, and overcoming adversity. Here are some of my favorite films that every leader and entrepreneur should watch.

1. The Social Network (2010)

Lesson: Innovation and the Price of Success

This film chronicles the meteoric rise of Facebook and the challenges that came with it. It’s a fascinating study in ambition, vision, and the complexities of scaling a disruptive business. It also highlights the importance of maintaining strong relationships and ethical decision-making in the pursuit of success.

Key Takeaways:

  • Disruptive ideas can change the world, but execution is everything.
  • Leadership isn’t just about innovation—it’s also about integrity and partnership.
  • Success comes with tough choices; not all of them will be popular.

2. Moneyball (2011)

Lesson: Data-Driven Leadership and Challenging the Status Quo

Billy Beane, played by Brad Pitt, revolutionizes baseball management by using data analytics to build a competitive team on a budget. This film is a must-watch for any entrepreneur looking to challenge conventional thinking and make smarter business decisions based on insights rather than instinct.

Key Takeaways:

  • Data-driven decisions can disrupt entire industries.
  • Leadership requires the courage to challenge norms.
  • Success isn’t about resources; it’s about resourcefulness.

3. The Pursuit of Happyness (2006)

Lesson: Resilience and Never Giving Up

This powerful film, based on the true story of Chris Gardner, showcases the sheer determination and grit required to overcome adversity. It’s an emotional reminder that success often comes down to persistence and self-belief, even in the face of overwhelming odds.

Key Takeaways:

  • Resilience is the key to success.
  • Hard work and perseverance can change your life.
  • Every great entrepreneur has faced moments of doubt—pushing through is what sets them apart.

4. Jerry Maguire (1996)

Lesson: Passion and Building Relationships

One of the most quotable movies in business circles, Jerry Maguire is all about passion, integrity, and believing in your vision. Tom Cruise’s character leaves a high-powered agency to start his own venture, proving that great businesses are built on relationships, trust, and unwavering belief in your mission.

Key Takeaways:

  • Success isn’t just about money—it’s about purpose.
  • Building strong, authentic relationships is key in business.
  • Sometimes taking a big risk is the only way to truly succeed.

5. The Wolf of Wall Street (2013)

Lesson: The Power (and Danger) of Sales and Charisma

While this film is a cautionary tale, it’s also a fascinating look at the power of persuasion, confidence, and the impact of leadership—both good and bad. Entrepreneurs can take away valuable lessons on motivation, sales strategy, and the ethical responsibility that comes with leadership.

Key Takeaways:

  • Confidence and salesmanship are powerful tools—use them wisely.
  • Ethical leadership is crucial for long-term success.
  • Vision without integrity leads to downfall.

6. Ford v Ferrari (2019)

Lesson: Leadership and Taking Risks

This film tells the true story of how Ford challenged Ferrari’s dominance in motorsports. It’s a masterclass in leadership, teamwork, and pushing the boundaries of what’s possible. It’s also a reminder that great leaders empower their teams and trust them to execute ambitious ideas.

Key Takeaways:

  • Innovation requires boldness and risk-taking.
  • Strong leadership means trusting your team’s expertise.
  • Competition fuels excellence—embrace it.

7. The Founder (2016)

Lesson: Scaling a Business and the Cost of Ambition

The story of Ray Kroc and the rise of McDonald’s is both inspiring and controversial. It showcases the importance of vision and scalability while also serving as a cautionary tale about ethics in business growth.

Key Takeaways:

  • Visionary thinking can turn a small idea into a global empire.
  • Scaling a business requires process, branding, and consistency.
  • Business ethics matter—success shouldn’t come at the cost of integrity.

Final Thoughts: Leadership Lessons from the Big Screen

Great leaders and entrepreneurs know that learning never stops, and sometimes the best lessons come from unexpected places—including Hollywood. Whether it’s about resilience, innovation, ethics, or relationship-building, these films offer valuable insights into what it takes to lead and build something great.

So, next time you need a little inspiration, skip the business book and turn on one of these classics. You just might find the spark that drives your next big idea.

About Karry Kleeman

​​Karry Kleeman is a seasoned software executive, go-to-market strategist, and revenue leader. He thrives at the intersection of business growth and human connection, blending a sharp instinct for scaling companies with a deep passion for people and a commitment to infusing a human touch into the process. He is known for bringing energy and clarity to organizations—rallying teams around a common mission, driving execution, and creating momentum that fuels growth.

With a career spanning decades in enterprise software, Karry has built and led high-performing revenue organizations from early-stage startups to IPOs and strategic acquisitions. He has played a pivotal role in scaling multiple companies to successful exits, generating well over $1 billion in enterprise value. At LogicGate, he architected a go-to-market strategy that propelled the company from $1M to $50M in ARR. At SpringCM, he led the revenue function through its $270M acquisition by DocuSign. And at Mobius he helped scale the business from $3M to over $100M, culminating in a successful IPO.

Karry’s ability to inspire and energize teams is a core part of his leadership. Just as he commands attention and engagement when performing live music, he brings the same presence and intensity to leading teams—aligning them around a shared vision, setting the pace, and ensuring everyone is moving in rhythm toward ambitious goals. When he’s not driving business growth, you’ll find him performing classic rock hits anywhere he can find a live mic.