25 Must-Watch Documentaries Every Entrepreneur Should See
Fuel Your Business Brain with Real Stories of Innovation, Risk, and Growth
When you’re running a business, time is your most valuable resource. But inspiration, insight, and perspective? Just as essential. And that’s where documentaries come in.
Unlike fictional dramas or Hollywood-fueled entrepreneur biopics, business documentaries offer something real—raw footage, firsthand accounts, and behind-the-scenes looks at how legendary companies rise, fall, pivot, or blow up spectacularly. Whether you're stuck in the grind, scaling hard, or just need a mental shift, these documentaries will make you think deeper about your business and yourself.
We pulled together 25 of the best entrepreneurial documentaries across Netflix, Amazon Prime, HBO Max, and YouTube. These aren’t just binge-worthy—they’re toolkits for your growth as a founder, investor, or builder.
Why Entrepreneurs Should Watch Documentaries
Think of documentaries as case studies in motion. You see:
What worked (and why)
What failed (and how)
The human side of the hustle
The systems and strategies behind successful brands
More importantly, documentaries reveal the mindset and grit behind the stories—something books and blogs don’t always capture.
What You'll Learn
These documentaries teach lessons in:
Leadership under pressure
Product-market fit (and how people get it wrong)
Ethics in business (or the lack of them)
Funding, scale, failure, and survival
Market disruption and innovation
The real cost of bad UX or product failure
A Preview of Our Top Picks
Here are a few standouts from the full list:
Startup.com — A raw look at a startup rising and falling in the dot-com bubble. A must-see for anyone building with a cofounder.
Fyre: The Greatest Party That Never Happened — A masterclass in hype, fraud, and how not to launch a brand. It’s funny… until it’s not.
The Inventor: Out for Blood in Silicon Valley — Theranos’ downfall is a case study in what happens when the pitch outpaces the product.
Becoming Warren Buffett — A personal and powerful deep dive into how the Oracle of Omaha built an empire with restraint and clarity.
Inside Bill’s Brain — Explore the curiosity and focus that made Gates a tech legend and one of the most effective philanthropists alive.
Dirty Money — This series pulls no punches on corporate greed, fraud, and shady business practices. It's riveting and enraging.
The Last Dance — Not strictly about business, but packed with lessons on leadership, culture, and staying at the top.
How to Use This List
If you’re an entrepreneur, pick a few based on your current phase:
Starting Out? Watch Startup.com, The Pixar Story, or Something Ventured.
Scaling Fast? Try WeWork, Enron, Downfall: Boeing.
Need Leadership Inspiration? Go with The Last Dance, Becoming Warren Buffett, or Inside Bill’s Brain.
Curious About Ethics and Risk? Fyre, Dirty Money, and The Great Hack will open your eyes.
You don’t need to watch all 25 in one go. Save them. Bookmark this list. Revisit them during your next flight, weekend break, or when your brain needs a refresh.
1. Startup.com
Platform: YouTube
A real-life crash course in startup dynamics and dot-com era hype. Follows two childhood friends who build GovWorks—only to implode from internal conflict. Must-watch for first-time founders.
2. Fyre: The Greatest Party That Never Happened
Platform: Netflix
The infamous Fyre Festival scam captured from the inside. A cautionary tale about influencer marketing, fake hype, and what happens when the product doesn’t match the promise.
3. Enron: The Smartest Guys in the Room
Platform: Amazon Prime
Unpacks one of the largest corporate frauds in U.S. history. Great insight into how culture and accounting manipulation can destroy even the biggest companies.
4. The Inventor: Out for Blood in Silicon Valley
Platform: HBO Max
Follows the rise and collapse of Theranos. Explores how charisma and over-promising tech can lure investors into billion-dollar lies.
5. Becoming Warren Buffett
Platform: HBO Max
A personal portrait of one of the greatest investors of all time. Inspiring and humanizing insight into Buffett’s values and strategies.
6. Inside Bill’s Brain: Decoding Bill Gates
Platform: Netflix
A 3-part series offering a look at Gates’ problem-solving mindset, both in business and global health initiatives. Valuable perspective for systems thinkers.
7. Dirty Money
Platform: Netflix
A series showcasing corporate corruption across industries. Each episode is a deep dive into fraud, manipulation, and greed.
8. Downfall: The Case Against Boeing
Platform: Netflix
Reveals how Boeing prioritized profits over safety, leading to two fatal crashes. An eye-opener on culture, risk, and the price of shortcuts.
9. The Pixar Story
Platform: Disney+
Chronicles Pixar’s growth from a small animation company into a world-class brand. Insight into creativity, leadership, and product-market fit.
10. Betting on Zero
Platform: Amazon Prime
Follows hedge fund manager Bill Ackman’s quest to short Herbalife, calling it a pyramid scheme. A crash course in finance, regulation, and business ethics.
11. Steve Jobs: One Last Thing
Platform: YouTube
A brief documentary reflecting on Jobs’ legacy, leadership, and impact. Good for fans who want a concise overview of his influence.
12. The Last Dance
Platform: Netflix
A 10-part documentary on Michael Jordan’s final season with the Bulls. Not just for sports fans—packed with leadership, mindset, and branding lessons.
13. Capital C
Platform: YouTube
Explores the power of crowdfunding by following three creators using Kickstarter to launch products. Honest look at the emotional rollercoaster of building something from scratch.
14. Silicon Cowboys
Platform: Amazon Prime
Tells the story of Compaq and its battle against IBM. A “David vs. Goliath” tale that captures the heart of entrepreneurial grit.
15. Triumph of the Nerds: The Rise of Accidental Empires
Platform: YouTube
Classic tech doc exploring the early days of Apple, Microsoft, and others. Includes rare interviews with Gates and Jobs. Required viewing for tech founders.
16. Banking on Bitcoin
Platform: YouTube
Perfect primer for those curious about crypto. Covers the origins, philosophy, and controversy surrounding Bitcoin.
17. LulaRich
Platform: Amazon Prime
Follows the rise and unraveling of the multi-level marketing company LuLaRoe. Essential for understanding modern business manipulation.
18. Money, Explained
Platform: Netflix
Short, sharp episodes exploring personal finance, credit cards, scams, and more. Great for entrepreneurs looking to strengthen financial literacy.
19. Steve Jobs: The Man in the Machine
Platform: Amazon Prime
Offers a more nuanced, critical look at Jobs’ leadership and personality. Contrasts his brilliance with his personal flaws.
20. WeWork: Or the Making and Breaking of a $47 Billion Unicorn
Platform: Hulu
A deep dive into Adam Neumann’s explosive rise and fall. A textbook case on cult-like founders and VC excess.
21. Print the Legend
Platform: Netflix
Documents the race to dominate the 3D printing industry. Ideal for makers, hardware startups, and future-tech enthusiasts.
22. Something Ventured
Platform: YouTube
Tells the story of the early VCs who backed Apple, Intel, and Cisco. A must-watch if you're fundraising or learning how VCs think.
23. Generation Hustle
Platform: HBO Max
Each episode spotlights a different scammer or hustler. Entertaining and educational, with plenty of red flags to learn from.
24. White Hot: The Rise & Fall of Abercrombie & Fitch
Platform: Netflix
Tracks how the brand dominated youth culture before collapsing under controversy. A brand and marketing case study in one.
25. The Crime of the Century
Platform: HBO Max
Breaks down the opioid crisis and corporate greed behind it. Focuses on Purdue Pharma and Insys. Harrowing, but important.
Final Thought
Every one of these documentaries contains valuable lessons for entrepreneurs—from scaling and funding to ethics and leadership. Whether you want to study startups, avoid pitfalls, or understand the big-picture impact of business decisions, there’s something in this list for you.
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