27 Best Documentaries for Entrepreneurs

27 Best Documentaries for Entrepreneurs

If you’re in need of inspiration in your entrepreneurial journey or you’d like a break from your hectic schedule, watching business documentaries is an excellent way to unwind and learn more about your craft. Business documentaries can be both entertaining and insightful, while also providing important lessons and mental models in innovation and critical thinking.

While you can always watch business-focused movies like The Social Network, The Wolf of Wall Street, and Boiler Room, the element of authenticity in business documentaries resonates with entrepreneurs at a deeper level.

With so many business documentaries on so many different streaming platforms, it can be difficult to separate the wheat from the chaff.

Don’t worry, we have you covered!

In this post, we have cherry-picked the 27 best documentaries that entrepreneurs and business owners can watch on Netflix, Amazon Prime, HBO Max, Disney+, and YouTube.

By the time you’re done with this post, you’ll have 27 of the best entrepreneur documentaries to add to your watchlist.

Top 27 Business Documentaries That Every Entrepreneur Should Watch

1. Startup.com

Startup.com Documentary

Image Credit: Amazon

The dotcom bubble was responsible for the meteoric rise and spectacular fall of many promising startups. GovWorks was one of them. Startup.com is a 2001 documentary that explores the story of how a promising startup like GovWorks failed due to mismanagement and internal power struggles.

It always amazes me why this documentary is not as popular amongst entrepreneurs as it should be. It’s one of the best startup documentaries ever made. It brilliantly captures all the advantages and pitfalls of launching a startup with friends during exciting, yet uncertain times.

If you’d like an understanding of how startups operated during the boom and bust of the dotcom bubble era, Startup.com is a must-watch documentary. Started by friends who transformed into bitter rivals, this documentary tells a cautionary tale for entrepreneurs on how internal power struggles can prove detrimental to your company’s future.

Meticulously edited from over 400 hours of footage, Startup.com provides a behind-the-scenes look at all the things that can go wrong at a company that has everything going for it.

IMDB Rating: 7.1/10 (3,400+ user ratings)
Rotten Tomatoes Score: Not enough ratings
Where to Watch: YouTube (you can watch the full documentary here)

Watch the trailer below:

2. Fyre: The Greatest Party That Never Happened

Fyre on Netflix

Image Credit: What’s New on Netflix

Fyre Festival was supposed to be the greatest and most extravagant music festival of all time. It was promoted heavily on social media by celebrities, social media influencers, music bands, and supermodels. All the promotional materials indicated that the attendees would be served gourmet meals from celebrity chefs and that they’d get luxury accommodations on a private island previously owned by Pablo Escobar.

With serial entrepreneur Billy McFarland and well-known rapper Ja Rule at the helm, what could go wrong? As it turns out, everything. In reality, Fyre Festival was a scam and the complete opposite of what was advertised in every conceivable way. The artists that were supposed to perform at the event pulled out and the attendees were left stranded on an island in disaster-relief tents with no access to food and water.

This Netflix documentary offers an exclusive behind-the-scenes look into the fraudulent luxury music festival. Featuring shocking revelations from McFarland’s team members and festival attendees, Netflix’s Fyre is an entertaining watch and a cautionary tale for entrepreneurs who make bold promises without actually working on their product.

As it turns out, Fyre Festival founder Billy McFarland had a history of starting up fraudulent businesses and Fyre turned out to be the biggest scam he ever pulled.

Side note: You can also watch another documentary on Fyre Festival called Fyre Fraud on Hulu which was released at around the same time. The Netflix documentary is superior, but Hulu’s documentary has its moments.

IMDB Rating: 7.2/10 (45,000+ user ratings)
Rotten Tomatoes Score: 93%
Where to Watch: Netflix

Watch the trailer below:

3. Enron: The Smartest Guys in the Room

Enron Documentary

Image Credit: TV Guide

A list comprising of the best business documentaries would be incomplete without this documentary on the Enron scandal. Based on the book The Smartest Guys in the Room by investigative reporters Bethany McLean and Peter Elkind, this documentary examines the fall of Enron Corporation in 2001 and all the key players involved in the infamous Enron scandal.

Featuring interviews with the reporters who first broke the news and former Enron executives and employees, this documentary deep dives into all the nefarious activities at Enron that led to its eventual downfall. From its misleading mark-to-market accounting practices to its lavish corporate parties to the deceitful behavior of top executives, this business documentary reveals everything you need to know about one of the biggest corporate scandals of the 21st century.

IMDB Rating: 7.6/10 (18,000+ user ratings)
Rotten Tomatoes Score: 97%
Where to Watch: Amazon Prime; YouTube (you can watch the full documentary here)

Watch the trailer below:

4. The Inventor: Out for Blood in Silicon Valley

The Inventor Documentary

Image Credit: Hotstar

The story of Theranos’ rise and fall should be studied by every entrepreneur out there. While there’s been a lot of media covering the Theranos scandal, from John Carreyrou’s brilliant book Bad Blood to the latest limited TV series The Drop Out, The Inventor can be a good starting point to get your dose of the things that transpired at Theranos.

Once positioned to transform the healthcare industry, Theranos was one of the most talked-about Silicon Valley companies and its founder Elizabeth Holmes was a media darling and was the world’s first self-made female billionaire. It all came crashing down when everyone realized Theranos’ revolutionary blood testing technology just didn’t work. Moreover, Holmes and Theranos’ COO Sunny Balwani used a lot of intimidation tactics to suppress skepticism and criticism from the employees and tech reporters.

The film chronicles how Holmes and Balwani engaged in fraudulent practices to mislead investors and business partners, and how both of them were more interested in marketing, promotion, and fame than in getting the actual mechanics of their technology working.

While it provides a good overview of Theranos’ rise and fall, I’d highly recommend reading John Carreyrou’s Bad Blood. Carreyrou was the first reporter to report on issues at Theranos and his 2015 Wall Street Journal article prompted multiple investigations and lawsuits which eventually brought an end to Holmes’ deception and Theranos’ downfall.

IMDB Rating: 7.1/10 (12,000+ user ratings)
Rotten Tomatoes Score: 79%
Where to Watch: HBO Max; Disney+ Hotstar in India

Watch the trailer below:

5. Becoming Warren Buffett

Becoming Warren Buffet

Image Credit: Hotstar

If you want to learn about Warren Buffet’s life and investment philosophy, this business documentary is for you. Buffet is an excellent role model for young and aspiring entrepreneurs. He also happens to be one of the most likeable billionaires out there (a rare quality).

Becoming Warren Buffet doesn’t just reveal the secrets behind Buffet’s business acumen, but also delves into his personal relationship skills. If you’re seeking important life and investment lessons, this is one of the best business documentaries you can learn from.

IMDB Rating: 7.5/10 (4,400+ user ratings)
Rotten Tomatoes Score: Not enough ratings
Where to Watch: HBO Max; Hotstar Disney+ in India

Watch the trailer below:

6. Inside Bill’s Brain: Decoding Bill Gates

Bill Gates Documentary on Netflix

Image Credit: Netflix

This three-part Netflix documentary series explores the mind, mental models, and motivations of Bill Gates and takes a deeper look into his charity work with Bill and Melinda Gates Foundation, which he co-founded with his then-wife Melinda Gates.

This documentary received mixed reviews at the time of its release because of the bad press Gates was dealing with at the time. As a matter of fact, Bill Gates’ eventual divorce with Melinda Gates makes this an awkward watch at times. But to write off this documentary as “superficial” as a review at The Verge did is like missing the forest for the trees. It’s to overlook the impact that Gates had in the world of entrepreneurship, technology, and philanthropy.

Watch it to be inspired by one of the most brilliant tech visionaries of our generation.

IMDB Rating: 7.9/10 (11,000+ user ratings)
Rotten Tomatoes Score: 43%
Where to Watch: Netflix

Watch the trailer below:

7. Dirty Money

Dirty Money on Netflix

Image Credit: Netflix

Dirty Money is a critically-acclaimed Netflix documentary series that tells the stories of corporate fraud and corruption. Featuring hour-long episodes, each episode focuses on one example of corporate corruption and fraud, making it one of the best business documentaries on Netflix.

For me, the standout episode in the series was Payday (Season 1, Episode 2) that explains how amateur racing driver Scott Tucker ran a fraudulent operation of providing payday loans with extremely high-interest rates. The final episode of season 1 revolves around Donald Trump and his numerous scandals and controversies before he became the 45th president of the United States.

At the time of writing this post, Dirty Money has 2 seasons with 6 episodes each. There’s plenty of cautionary tales for entrepreneurs in this must-watch business documentary series.

IMDB Rating: 8.1/10 (9,000+ user ratings)
Rotten Tomatoes Score: 100%
Where to Watch: Netflix

Watch the trailer below:

Related: 10 Best TV Shows for Entrepreneurs

8. Downfall: The Case Against Boeing

Downfall on Netflix

Image Credit: Netflix

This documentary offers a classic lesson on what happens when a company values financial gain over safety of its customers, and creates a toxic workplace which stifles innovation.

Directed by Rory Kennedy, whose documentaries typically revolve around social and political issues, Downfall examines two major airline crashes involving Boeing planes and how Boeing’s negligence and culture of concealment made these tragedies unpreventable.

Worse still, Boeing tried to evade accountability and shifted the blame on pilots. Even when Boeing was finally held accountable for the crashes, they got away with a slap on the wrist.

Featuring interviews of former Boeing employees, victims’ family members, and aviation experts, this documentary makes a compelling case on how Boeing’s greed and toxic work environment cost hundreds of lives. It also showcases Boeing’s transformation from a team of safety-conscious engineers who took pride in their work to a company with greedy and incompetent leaders whose only goal was to maximize shareholder value.

IMDB Rating: 7.4/10 (8,000+ user ratings)
Rotten Tomatoes Score: 90%
Where to Watch: Netflix

Watch the trailer below:

9. The Pixar Story

The Pixar Story

Image Source: Hotstar

Pixar played a huge role in pioneering a new generation of animation with hits such as Toy Story, Finding Nemo, The Incredibles, and several others. This 2007 documentary offers a behind-the-scenes sneak peek of Pixar Animation Studios.

The Pixar Story offers an insight into the first few years of Pixar, starting from the success of Toy Story to the company’s relationship with its parent company Disney to the role Steve Jobs played in the initial years. It also profiles the contributions of Pixar’s co-founders Ed Catmull and John Lasseter.

If you’re a fan of Pixar movies, then it goes without saying that this is a must-watch documentary. Not only will you learn a few things about how the company functions, but you’ll also find important lessons on how to succeed against surmounting odds.

IMDB Rating: 7.7/10 (6,600+ user ratings)
Rotten Tomatoes Score: 86%
Where to Watch: Disney+; Hotstar Disney+ (India)

Watch the trailer below:

10. Betting on Zero

Betting on Zero

Image Credit: Amazon

If you’ve watched John Oliver’s segment on Herbalife on Last Week Tonight, you’d know there’s something deeply wrong with the business practices of Herbalife. It’s a global multi-level marketing (MLM) company disguised as a nutrition company.

Betting on Zero chronicles the controversial billionaire hedge fund manager Bill Ackman’s journey to expose Herbalife as the largest pyramid scheme in history. The documentary starts by explaining Ackman’s short position of over a billion dollars on the Herbalife stock and follows his attempts to expose Herbalife’s controversial business practices.

The film also examines Ackman’s public feud with Herbalife’s former CEO Michael Johnson and fellow investor Carl Icahn. Equally important, it also reveals how MLM companies like Herbalife rely on the power of messaging to generate millions of followers.

IMDB Rating: 7.2/10 (5,300+ user ratings)
Rotten Tomatoes Score: 100%
Where to Watch: Amazon Prime

Watch the trailer below:

11. Steve Jobs: One Last Thing

Steve Jobs: One Last Thing

Released a few weeks after Steve Jobs’ death in 2011, this short documentary features reflections from Jobs’ friends, colleagues, fans, and rivals on his life and achievements. It also includes excerpts from an interview with Bill Gates and Steve Jobs shortly after Jobs was diagnosed with pancreatic cancer.

If you’ve already read Steve Jobs’ biography by Walter Isaacson, then this documentary will probably not reveal anything you didn’t know about Jobs. But if you want a quick overview of Jobs’ achievements and business philosophy, this hour-long documentary is perfect.

IMDB Rating: 6.7/10 (800+ ratings)
Rotten Tomatoes Score: Not enough ratings
Where to Watch: YouTube (you can watch the full documentary here)

Watch the trailer below:

12. The Last Dance

The Last Dance

Image Credit: The Sporting News

This 10-part Netflix documentary series is not just for Michael Jordan and Chicago Bulls fans. As a matter of fact, you don’t even need to be a basketball or sports fan to appreciate how brilliant this series truly is. I’ve included this series in the list of best documentaries for entrepreneurs because it offers deep insights into Michael Jordan’s leadership style and how he motivated not just himself but his entire team to strive for the best.

It also shows Jordan’s growth mindset at its peak which made him such a fierce competitor on the court who believed in winning at all costs. You may not agree with his leadership style or his way of motivating his teammates (Jordan has his critics), but even his harshest critic won’t doubt the sheer grit, determination, and the winners’ mentality he possessed.

The Last Dance neatly juxtaposes Michael Jordan’s last season with the Chicago Bulls alongside his early years when he was still a rookie at Bulls. Also documented are the careers of Jordan’s teammates Scottie Pippen and Dennis Rodman, and Chicago Bulls’ head coach Phil Jackson.

If you were a Michael Jordan or Chicago Bulls fan in the 90s, then it’s a no-brainer that you should watch this documentary. But like I said, even if you have no interest in basketball, this documentary is a compelling watch that’s filled with lessons for entrepreneurs and other achievers.

The Last Dance may be a sports documentary series, but if you analyze it closely, each episode contains a plethora of lessons for entrepreneurs from all walks of life. It’s hands down one of the best Netflix documentaries for entrepreneurs.

IMDB Rating: 9.1/10 (110,000+ user ratings)
Rotten Tomatoes Score: 97%
Where to Watch: Netflix

Watch the trailer below:

13. Capital C

Capital C Documentary

Image Credit: YouTube

This little-known business documentary is probably the only documentary film about crowdfunding. The movie itself was co-funded by a crowdfunding campaign on Kickstarter.

Capital C focuses on the hopes, fears, and struggles of independent creators in the digital age. Shot over a period of three years, the documentary revolves around poker card designer Jackson Robinson, hippie Zach Crain, and video game veteran Brian Fargo as they embark on a journey to crowdfund their business ideas.

The movie features interviews from Seth Godin, Felix Salmon, Eric von Hippel, and many other experienced entrepreneurs, authors, and technologists who share their views on startups and crowdfunding.

IMDB Rating: 6.8/10 (270+ user ratings)
Rotten Tomatoes Score: Not enough ratings
Where to Watch: It’s quite hard to find the full documentary online, but if you live in the UK, you can watch it on Amazon Prime.

Watch the trailer below:

14. Silicon Cowboys

Silicon Cowboys Documentary

Image Credit: YouTube

This 2016 documentary chronicles the journey of three friends, Rod Canion, Jim Harris, and Bill Murto, who founded Compaq in the early 1980s and their decade-long battle against the mighty IBM for PC supremacy. It’s the ultimate “David vs Goliath” story that all entrepreneurs will enjoy and derive lessons from.

Silicon Cowboys examines the rise of Compaq and how the company began making inroads in the lucrative personal computing industry. With the launch of Compaq Portable, the company achieved mainstream acceptance and IBM finally began to take notice. IBM responded with its own portable computer and thus began an intense rivalry for PC supremacy that would last a decade.

This documentary features a ton of archive footage and interviews with all the major players in the personal computing industry from the 80s to give you a complete breakdown of the fierce rivalry between Compaq and IBM.

IMDB Rating: 6.8/10 (2,000 user ratings)
Rotten Tomatoes Score: 100%
Where to Watch: Amazon Prime (US & UK)

Watch the trailer below:

15. The Triumph of the Nerds: The Rise of Accidental Empires

Triumph of the Nerds

Image Credit: Amazon Prime

Even if you have not seen the full documentary, I’m fairly certain you’d have seen a few clips from it on YouTube, particularly this one of Steve Jobs explaining his frustration with Microsoft.

Based on the book Accidental Empires, this three-part documentary features candid interviews of all the important people connected with the rise of personal computer, including Bill Gates, Steve Jobs, Steve Wozniack, Paul Allen, Steve Ballmer, Larry Ellison, and many more. It also features commentary from Douglas Adams, the author of the cult classic sci-fi series The Hitchhiker’s Guide to the Galaxy.

Triumph of the Nerds examines the steady development and rise of the personal computer from World War II to 1995. Released in 1996, this documentary was released just before Jobs’ second stint with Apple began.

It may be dated, but it’s still one of the best documentaries for entrepreneurs who’d like a sneak peek into the inner workings of some of the most dynamic tech entrepreneurs who paved the way for the future.

IMDB Rating: 8.4/10 (1,300+ user ratings)
Rotten Tomatoes Score: Not enough ratings
Where to Watch: YouTube (you can watch the full documentary here)

I couldn’t find the trailer of this movie online, but you can watch a short segment of Steve Jobs’ introduction in the documentary:

16. Banking on Bitcoin

Banking on Bitcoin

Image Credit: YouTube

This documentary is a must-see for crypto entrepreneurs, investors, and enthusiasts. Naval Ravikant once said, “Bitcoin is a tool for freeing humanity from oligarchs and tyrants, dressed up as a get-rich-quick scheme.” This documentary perfectly exemplifies Naval’s statement by making a compelling case for the adoption of bitcoin while simultaneously offering opposing viewpoints.

Banking on Bitcoin explains the fundamentals of bitcoin, its origins, and features interviews from crypto entrepreneurs and financial journalists who’ve covered the phenomenal rise and volatility of bitcoin in the last few years. It’s a business documentary that both crypto beginners and long-time investors will appreciate.

IMDB Rating: 6.6/10 (3,600+ user ratings)
Rotten Tomatoes Score: Not enough ratings
Where to Watch: YouTube (you can watch the full documentary here)

Watch the trailer below:

17. LulaRich

LulaRich Documentary

Image Credit: YouTube

A documentary series from the makers of Fyre Fraud, LulaRich chronicles the rise and fall of the LuLaRoe leggings multi-level marketing (MLM) company. Although this documentary is not as well known or mainstream as Fyre Fraud, it’s still an entertaining documentary about business scam and deception.

Featuring exclusive interviews with retailers, employees, the company founders, and more, this four-part Amazon Prime documentary series delves into all the things that went wrong at LulaRoe. It also features Robert L. FitzPatrick, author and president of Pyramid Scheme Alert, who does a great job breaking down how MLMs and pyramid schemes operate.

IMDB Rating: 7.7/10 (3,400+ user ratings)
Rotten Tomatoes Score: 100%
Where to Watch: Amazon Prime

Watch the trailer below:

18. Money, Explained

Money, Explained

Image Credit: Netflix

From the makers of the popular Explained series on Netflix, this spinoff documentary series explores how money works and the different ways in which we spend it, borrow it, and save it. It deconstructs topics like financial scams and get-rich-quick schemes, credit cards, student loans, gambling, and retirement.

The first season consists of 5 episodes. For me, the standout episode was the first episode which delves deep into the world of financial scams. It documents the history of con artists and scammers and how technology is making it easier for scammers and fraudsters to flourish.

IMDB Rating: 6.9/10 (2,100+ user ratings)
Rotten Tomatoes Score: Not enough ratings
Where to Watch: Netflix

Watch the trailer below:

19. Steve Jobs: The Man in the Machine

Steve Jobs: The Man in the Machine

Image Credit: Amazon Prime

The second Steve Jobs documentary in this list, this film takes a deeper look at the professional and private life of Steve Jobs. It’s one of the best business documentaries on Amazon Prime that you can watch right now.

Steve Jobs continues to be a divisive figure in the tech industry and this documentary film doesn’t shy away from exploring the dichotomy in Jobs and takes a more balanced view of an entrepreneur who’s equally revered for his genius and reviled by critics for his controlling and megalomaniacal nature.

This documentary reminds us to accept Jobs with his genius as well as his flaws. He was human just like the rest of us, after all. And humans are imperfect creatures. It’s only when we accept this fact that we can truly appreciate his contributions to the world.

IMDB Rating: 6.9/10 (6,000+ user ratings)
Rotten Tomatoes Score: 74%
Where to Watch: Amazon Prime

Watch the trailer below:

20. WeWork: Or the Making and Breaking of a $47 Billion Unicorn

WeWork Documentary

Image Credit: Engadget

This business documentary examines the rise and fall of WeWork, a company that was once valued at $47 billion dollars. It focuses mainly on the six weeks leading up to WeWork’s disastrous IPO and offers a behind-the-scenes look at the frat-boy culture prevalent within WeWork.

With a narcissistic founder like Adam Neumann at the helm, WeWork was doomed from the start. Despite running what was essentially just a cozy co-working space, Neumann envisioned WeWork to be a technology company. Investors bought into Neumann’s lofty dreams and invested billions of dollars in the company. It was only when Neumann decided to take his company public that WeWork’s finances and leadership came under intense scrutiny, revealing its shady business practices and Neumann’s extravagant lifestyle.

WeWork and Adam Neumann’s eventual fall from grace has several lessons for business leaders. Above all, it’s a cautionary tale for entrepreneurs and venture capitalists alike. It shows us how one can be easily deceived by a founder’s “cult of personality” even when they have nothing unique to offer. At the end of the day, a company’s product, fundamentals, business model, and work ethic should always take precedence over the founder’s charismatic salesmanship and brilliant vision for the company.

This business documentary offers a good primer on the WeWork fiasco, but if you’d like to learn more about Neumann’s notoriety and the whole WeWork fiasco, I’d urge you to read Billion Dollar Loser by Reeves Wiedeman or watch the Apple+ limited series WeCrashed, starring Jared Leto as Adam Neumann and Anne Hathaway as Rebecca Neumann. The business podcast that the show is adapted from is also worth a listen.

IMDB Rating: 6.6/10 (2,800+ user ratings)
Rotten Tomatoes Score: 76%
Where to Watch: Hulu (US)

Watch the trailer below:

Related: 10 Most Entertaining Business Podcasts

21. Nobody Speak: Trials of the Free Press

Nobody Speak Documentary

Image Credit: Netflix

When Terry Bollea (better known as Hulk Hogan) filed a lawsuit against Gawker Media for invading his privacy, very few thought the outcome would end up bankrupting Gawker. What we didn’t know at the time was that Hulk Hogan’s lawsuit was being bankrolled by billionaire venture capitalist Peter Thiel who saw this as a perfect opportunity for his own personal vendetta against Gawker.

Hogan’s lawsuit against Gawker proved to be a deciding factor in the company’s downfall. It was the final nail in their coffin. I’m no fan of Hulk Hogan, but it’s hard to sympathize with Gawker, a company which took numerous journalistic liberties while they were operating. As Variety describes it, “Gawker didn’t just kick you when you were down; it kicked you with a lip-licking grin.”

While Nobody Speak is biased towards Gawker in particular and the media in general, it’s still a good watch to get a lowdown of the whole Bollea v. Gawker lawsuit. But if you’d like a little more nuanced version of the whole saga, I’d highly recommend Ryan Holiday’s brilliant business thriller Conspiracy.

IMDB Rating: 6.5/10 (4,000+ user ratings)
Rotten Tomatoes Score: 91%
Where to Watch: Netflix

Watch the trailer below:

22. The Great Hack

The Great Hack on Netflix

Image Credit: The Great Hack

The 2018 Facebook-Cambridge Analytics data scandal shocked the world. It revealed to us the extent to which our personal data on Facebook could be harvested for advertising purposes. While you may already have a fair idea as to what Facebook does with our personal data, the scale at which the company takes liberties to do this may surprise you.

This Netflix documentary film examines the Cambridge Analytica scandal through people who were involved in it. Produced and directed by Jehane Noujaim and Karim Amer, who previously directed Startup.com, The Great Hack investigates the nefarious work of Cambridge Analytica in the politics of various countries, including UK’s Brexit campaign and the 2016 US elections, with the help of Facebook.

The most frustrating part of the whole scandal is that Facebook got away with this with a mere slap on the wrist.

IMDB Rating: 7/10 (23,000+ user ratings)
Rotten Tomatoes Score: 85%
Where to Watch: Netflix

Watch the trailer below:

23. Print the Legend

Print the Legend

Image Credit: Netflix

Print the Legend is a Netflix original documentary that deep dives into the history and growth of the 3D printing industry. It focuses on startups, established companies, and even a few controversial figures involved in the 3D printing industry.

One of these controversial figures is gun-rights activist Cody Wilson who got a lot of media attention when he fired the first 3D-printed gun. He is interviewed extensively in the documentary, offering a contrarian view on how the 3D printing industry may be used, or in his case, misused.

It’s a thought-provoking documentary that reveals the inner workings of the 3D printing industry and how a seemingly innocuous technology can be transformed into something disruptive.

IMDB Rating: 7/10 (2,000+ user ratings)
Rotten Tomatoes Score: Not enough ratings
Where to Watch: Netflix

Watch the trailer below:

24. Something Ventured

Something Ventured

Image Credit: YouTube

When you think about successful companies like Apple, Intel, and Cisco, it’s sometimes hard to imagine that only a handful of people believed in the revolutionary nature of these companies.

This business documentary is about these few individuals, the original venture capitalists who engaged in a game of high stakes to fund the companies very few people believed in at the time.

The film features interviews with prominent venture capitalists and entrepreneurs of the 1960s, 1970s, and 1980s. Examined from the perspective of venture capitalists, Something Ventured chronicles the thrills and spills involved in building some of the greatest companies of the 20th century and the behind-the-scenes drama that unfolded at these companies.

IMDB Rating: 7/10 (750+ user ratings)
Rotten Tomatoes Score: Not enough ratings
Where to Watch: YouTube (Watch the full documentary here)

Watch the trailer below:

25. Generation Hustle

Generation Hustle Documentary

Image Credit: Warner Media

This 10-part documentary series offers a broad summary of ten recent scammers and con artists of varying levels of notoriety. From the scam pulled by Anna Delvey (real name Anna Sorokin) in upscale Manhattan to the cult of Adam Neumann at WeWork, you’ll discover the lengths some people are willing to go to in pursuit of fame, wealth, and power.

For me, the standout episode was the Anna Delvey episode. It did a better job exposing Anna Delvey as a fraud than the Netflix series Inventing Anna, which presented a biased version of the events and vilified one of the victims.

IMDB Rating: 7.3/10 (400+ user ratings)
Rotten Tomatoes Score: Not enough ratings
Where to Watch: HBO Max

Watch the trailer below:

26. White Hot: The Rise & Fall of Abercrombie & Fitch

White Hot - Netflix

Image Credit: TV Insider

Abercrombie & Fitch was one of the coolest fashion brands for the 18-22 year olds in the late 90s and early 2000s. With aggressive advertising campaigns, catchy slogans, and innovative store concepts, A&F captured the attention of their demographic better than any of its competitors.

But over time, the company started indulging in offensive and problematic ad campaigns and t-shirt slogans and practiced exclusionary hiring practices, all of which resulted in consumer backlash, bad press, and a steep decline in the brand’s status.

Through interviews with former A&F employees, models, and reporters, White Hot reveals the secrets behind A&F’s success in the 90s and 2000s and explores all the factors that led to its eventual downfall.

IMDB Rating: 5.6/10 (2,000+ user ratings)
Rotten Tomatoes Score: 67%
Where to Watch: Netflix

Watch the trailer below:

27. The Crime of the Century

Crime of the Century

Image Credit: Variety

The Crime of the Century is one of the best business documentaries on HBO Max. Directed by Alex Gibney, this two-part documentary follows the opioid crisis in America and the companies that enable the abuse of opioids.

Part 1 of the film examines the role of Purdue Pharma to get the painkiller OxyContin approved for wider use, while downplaying its addictive potential. Part 2 of the documentary focuses on another addictive opioid Fentanyl and how the now-defunct Insys Therapeutics bribed doctors to overprescribe fentanyl.

Gibney’s documentary presents a grim picture of corporate greed and deconstructs the role played by Big Pharma and government regulations in the ongoing opioid crisis.

IMDB Rating: 8.1/10 (3,000+ user ratings)
Rotten Tomatoes Score: 95%
Where to Watch: HBO Max

Watch the trailer below:

Final Thoughts

So these are the 27 documentaries I’d recommend to entrepreneurs. If you think I’ve missed out on your favorite business documentaries, please let me know in the comments section. I’m always looking for more recommendations when it comes to business documentaries.

As entrepreneurs, it’s important that we embrace the growth mindset and become perpetual learners. As such, we should always be on a lookout for resources that can help us learn more about our craft. If you’re looking for more recommendations, check out these entrepreneur-focused posts on my blog:

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Editor’s Note: This article was first published on May 9, 2022 and has been updated regularly since then for relevance and comprehensiveness.

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Sandeep Mallya
Sandeep Mallyahttps://www.startupcafedigital.com
Sandeep Mallya is the Founder & CEO of Startup Cafe Digital, an award-winning digital marketing agency in Bangalore, India. He is an active member of the startup community, having worked with several early-stage startups and accelerators. 99signals is Sandeep's online marketing blog. The blog currently features 200+ in-depth articles, how-to guides, and hacks on a wide range of online marketing topics such as SEO, social media marketing, content marketing, blogging, and more.


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