The startup journey is filled with ups and downs, victories and failures, and countless lessons learned. While books and podcasts offer valuable insights, documentaries provide a unique, immersive look into the real stories behind successful (and failed) startups. In this comprehensive guide, we’ll explore the 20 must-watch startup documentaries that offer invaluable lessons for entrepreneurs.

20+ Must-Watch Startup Documentaries for Entrepreneurs (2024 Guide)

In the fast-paced world of startups, learning from others’ experiences can be the difference between success and failure. While books and podcasts offer valuable insights, documentaries provide an unfiltered, immersive look into the real stories behind both triumphant and failed startups. Let’s explore the most impactful startup documentaries that every entrepreneur should watch.

Essential Startup Documentaries

1. “Startup.com” (2001)

Despite its age, this documentary remains remarkably relevant today. Following GovWorks.com during the dot-com bubble, it captures the raw emotional journey of two friends whose relationship crumbles under the pressure of building a startup. The parallel between the early internet boom and today’s tech bubble makes this film particularly poignant.

2. “The Social Dilemma” (2020)

Former Silicon Valley executives reveal the hidden mechanisms behind social media platforms, offering crucial insights for tech entrepreneurs about the ethical implications of their products. This documentary forces founders to confront the question: “What responsibility do we have to our users?”

3. “WeWork: Or the Making and Breaking of a $47 Billion Unicorn” (2021)

A masterclass in what not to do when scaling a startup, this film chronicles WeWork’s meteoric rise and spectacular fall. It’s a sobering reminder that even the most valuable startups can collapse under the weight of unchecked ego and unsustainable business practices.

4. “Miss Americana” (2020)

While not strictly a startup documentary, Taylor Swift’s journey offers invaluable lessons about brand building, pivoting in response to market changes, and maintaining authenticity while scaling. It’s particularly relevant for founders building personal brands or creator-economy startups.

5. “The Inventor: Out for Blood in Silicon Valley” (2019)

The Theranos story serves as a crucial warning about the dangers of “fake it till you make it” culture in Silicon Valley. Elizabeth Holmes’s journey from celebrated founder to convicted fraudster offers sobering lessons about transparency and accountability.

6. “AlphaGo” (2017)

This compelling documentary about DeepMind’s AI beating the world’s best Go player offers fascinating insights into the future of artificial intelligence and its impact on society. Essential viewing for tech founders working in AI and machine learning.

7. “Print the Legend” (2014)

Following several 3D printing startups, this film showcases the challenges of hardware startups and the importance of timing in emerging markets.

8. “General Magic” (2018)

A beautiful tribute to visionary thinking, this documentary follows a company that conceptualized smartphone features decades before their time. It’s a powerful reminder that being too early to market can be just as devastating as being too late.

9. “Coded Bias” (2020)

An eye-opening exploration of bias in artificial intelligence, this documentary is crucial viewing for tech entrepreneurs building AI-powered products. It raises important questions about responsibility in technology development.

10. “Lo and Behold: Reveries of the Connected World” (2016)

Werner Herzog’s unique perspective on the internet and its impact on human society offers valuable insights for digital entrepreneurs about the broader implications of their work.

11. “Downloaded” (2013)

The rise and fall of Napster isn’t just about music sharing – it’s a crucial lesson in disruption, regulation, and the challenges of changing established industries.

12. “Silicon Cowboys” (2016)

The story of Compaq’s challenge to IBM’s dominance shows how startups can take on industry giants and win through innovation and determination.

13. “Crocodile in the Yangtze” (2012)

Jack Ma’s journey building Alibaba offers invaluable insights into entrepreneurship in emerging markets and the challenges of global expansion.

14. “She Did That” (2019)

A powerful exploration of Black women entrepreneurs, offering important perspectives on diversity in entrepreneurship and overcoming systemic barriers.

15. “The New Breed” (2020)

This documentary explores the rising trend of social entrepreneurship, showing how modern founders are combining profit with purpose.

16. “Betting on Zero” (2016)

A gripping look at Bill Ackman’s crusade against Herbalife, offering crucial lessons about business models, market manipulation, and corporate warfare.

17. “Capital C” (2014)

Following entrepreneurs using crowdfunding to launch their dreams, this film shows the power and challenges of alternative funding methods.

18. “Design Disruptors” (2016)

An inspiring look at how design-driven companies are reshaping industries, featuring insights from the world’s top product designers.

19. “Small Business Revolution” (2021)

While more focused on small businesses than startups, this series offers valuable lessons about business transformation and community impact.

20. “American Factory” (2019)

This Oscar-winning documentary explores the challenges of global business operations and cultural integration in modern manufacturing.

21. “LuLaRich” (2021)

A four-part series examining the rise and fall of LuLaRoe, offering crucial lessons about scaling, supply chain management, and the dangers of unsustainable growth.

22. “The Last Dance” (2020)

While focused on Michael Jordan and the Chicago Bulls, this series offers invaluable insights about leadership, team building, and maintaining excellence under pressure.

23. “Banking on Bitcoin” (2016)

Essential viewing for crypto and Web3 founders, providing historical context for the cryptocurrency revolution and its implications for financial technology.

Frequently Asked Questions

Why aren’t there more documentaries about successful startups?

Most successful companies are too busy building to allow documentary crews behind the scenes. Additionally, many success stories are still unfolding, making it difficult to tell a complete narrative. Failed startups often make for more dramatic and instructive stories.

How relevant are older startup documentaries in today’s landscape?

While technology and markets have evolved, human nature and basic business principles remain constant. Older documentaries often provide clearer insights because we can see how their stories played out over time.

Should I watch these documentaries before starting my company?

While these documentaries provide valuable insights, they shouldn’t delay your entrepreneurial journey. Watch them gradually as part of your continuous learning process, not as prerequisites to starting.

What’s the best order to watch these documentaries in?

Start with documentaries most relevant to your industry and current challenges. For example, if you’re in tech, begin with “Startup.com” and “The Social Dilemma.” If you’re focused on innovation, start with “General Magic” and “Print the Legend.”

How can I find more startup documentaries?

Follow film festivals like Sundance and SXSW, which often premiere startup and tech documentaries. Also, many streaming platforms now have dedicated business or startup documentary sections.

How to Make the Most of These Documentaries

To maximize learning from these documentaries:

1. Take Notes: Document key insights and strategies that apply to your business.
2. Watch with Partners: View these documentaries with your co-founders or team members to spark discussions about your own business strategies.
3. Follow Up: Research where these companies are now in 2024 to understand the long-term impact of their decisions.
4. Apply the Lessons: Create action items based on the insights gained from each documentary.

Final Thoughts

These documentaries offer more than just entertainment; they provide invaluable real-world lessons that every entrepreneur can apply to their journey.

As the startup landscape continues to evolve in 2024, the fundamental principles of leadership, innovation, and responsible growth remain steadfast. By learning from the successes and failures documented in these films, entrepreneurs can gain insights to better navigate their own startup journeys.