This edition is a bit special and very different from previous editions, but no less dense with strategic content.
In communities like ours, and on LinkedIn, everyone recommends books to read, but I thought that with Q4 looming, and Halloween just around the corner, it might be best to lighten the load.
I have collected for you 17 films in which Strategy turns into a nightmare.
Straight from my secret movie list, which I share with only a very few people, the most powerful movies about business, strategy, economics and society.
I selected these films preferring stories that actually happened or were inspired by real events, with a focus on entrepreneurs and their companies.
I favored plots that not only entertain, but also provoke deep questions and stimulate reflection.
Each film was chosen for the quality of its direction, casting, and soundtracks, avoiding obvious titles such as those about Steve Jobs or The Wolf of Wall Street. Instead, I preferred to highlight hidden gems, including several Italian films, and I accompanied each film with a trailer, ensuring that each offers a valuable strategic lesson.
In today’s note
- you will learn 17 strategic lessons hidden behind compelling storylines involving entrepreneurs, companies and financial scandals;
- you will find hidden gems and little-known Italian films with deep reflections on economics and society;
- you will see how hasty or unethical business choices can lead to disastrous consequences;
- you will discover which innovative or countercultural strategies have changed the course of corporate crises;
- you’ll be able to explore the dark side of business and strategic decisions through masterpieces of filmmaking and great casts.
1 – The Big Short
Original title: The Big Short
Italian title: The Big Bet
Year: 2015
Director: Adam Mckay
Cast: Christian Bale, Steve Carell, Ryan Gosling, Brad Pitt
Abstract: In the dark labyrinth of American finance, a group of outsiders discover a terrible secret: the entire economic system is built on a ticking time bomb. As the inevitable catastrophe approaches, they are faced with a deadly choice. Ignore the signs or face the nightmare that could engulf the entire world?
Based on real events: Yes, the film is based on the book by Michael Lewis and tells the true stories of those who predicted and bet against the housing bubble that led to the financial crisis of 2007-2008.
The strategic lesson: The film The Big Short offers a crucial strategic lesson about responsibility and ethics in the financial world. It examines how leverage can amplify risk, leading to devastating losses when the market crashes. The story highlights that the decisions of a few can have catastrophic consequences for millions. It also emphasizes the importance of critically analyzing information, as many industry players ignored warning signs, contributing to the 2008 financial crisis.
2 – Enron: The Smartest Guys in the Room
REPORT also covered it: Link to the episode
Original title: Enron: The Smartest Guys in the Room
Italian title: Enron – The Economics of Fraud
Year: 2005
Director: Alex Gibney
Cast: Documentary featuring interviews with former Enron executives and employees
Abstract: Behind the gleaming doors of Enron lurks a sinister shadow. Deceptive strategies and dangerous games turn the company into a house of cards ready to collapse. A chilling descent into the abyss of human greed, where the brightest minds orchestrate their own downfall.
Based on real events: Yes is a documentary that explores the real Enron scandal, one of the biggest cases of corporate fraud in American history.
The strategic lesson: a reflection on corruption and greed in business. Shows how accounting manipulation and lack of ethics can lead to apparent prosperity while masking serious financial problems. The “pump and dump” strategy used by Enron executives highlighted the danger of incentivizing investors to bet on companies that do not adhere to basic principles of transparency and accountability. This case serves as a warning about the importance of corporate governance and accountability in corporate management.
3 – Margin Call
Original title: Margin Call
Italian title: Margin Call
Year: 2011
Director: J. C. Chandor
Cast: Kevin Spacey, Paul Bettany, Jeremy Irons, Zachary Quinto
Abstract: On a fateful night, a financial analyst makes a disturbing discovery that threatens to destroy his company and the entire economic system. As darkness falls, sinister decisions must be made. Who will escape the nightmare they themselves have created?
Inspired by real events: Yes, although the film is a fictional story, it is inspired by the 2008 financial crisis and reflects the tensions within investment banks such as Lehman Brothers.
Strategic Lesson: The Margin Call leads to reflection on ethical responsibility in the world of finance. It shows how corporate decisions, made in crisis situations, can have devastating consequences not only for the company itself but also for the entire economic system. The CEO’s decision to quickly liquidate toxic assets, while aware of the risks, highlights the conflict between corporate survival and moral principles. This scenario invites reflection on the importance of transparency and integrity in financial practices
4 – The Boiler Room
Original title: Boiler Room
Italian title: 1 km from Wall Street
Year: 2000
Director: Ben Younger
Cast: Giovanni Ribisi, Vin Diesel, Nia Long, Ben Affleck
Abstract: Seduced by the lure of easy money, a young man joins a brokerage firm that hides a dark heart. As greed consumes everything, he finds himself caught in a web of deceit from which he may never escape. Will he be able to escape before it’s too late?
Inspired by real events: Yes, the film is inspired by real financial scandals related to fraudulent brokerage firms, similar to the Stratton Oakmont case depicted in “The Wolf of Wall Street,” which was released only 13 years later!
The strategic lesson: ambition and quick success can lead to ethically questionable decisions. The central strategic lesson is that success achieved without integrity is not sustainable; in the end, the consequences of wrong actions can destroy not only an individual’s career, but also personal life and relationships. The pursuit of profit must always be balanced with professional ethics….
5 – The little jewel
Original title: The Little Jewel
Year: 2011
Director: Andrea Molaioli
Cast: Toni Servillo, Remo Girone, Sarah Felberbaum
Abstract: Behind the gilded doors of an Italian food giant lies a dark financial secret. As executives orchestrate complex plots to disguise insurmountable debts, the company comes perilously close to the abyss. As the lies begin to unravel, an entire empire threatens to collapse, dragging thousands of lives with it into an endless nightmare.
Based on real events: Yes, the film is inspired by the Parmalat bankruptcy, one of the biggest financial scandals in Italian history.
The strategic lesson: The film offers a strategic lesson on the fragility of ethics in business. The central lesson is that compromising ethical values can lead to devastating consequences, not only for the individual, but also for the entire economic system.
6 – Human Capital
Original title: Human Capital
Year: 2013
Director: Paolo Virzi
Cast: Fabrizio Bentivoglio, Valeria Golino, Valeria Bruni Tedeschi
Abstract: In a northern Italian province, the lives of two families are intertwined in a whirlwind of ambition and greed. A mysterious incident triggers a series of events that reveal the shadows behind the facade of wealth. As tensions rise, uncomfortable truths emerge that could destroy all they know.
Based on real events: No, but reflects contemporary social and financial dynamics.
The strategic lesson: Several interconnected lives, reveal how personal decisions, often motivated by ambition and desire for status, can have devastating repercussions. The central lesson is that greed and the pursuit of success can lead to ethical compromises, emphasizing the importance of considering the impact of one’s actions on others.
7 – The Industrialist
Original title: The Industrialist
Year: 2011
Director: Giuliano Montaldo
Cast: Pierfrancesco Favino, Carolina Crescentini
Abstract: A Turin entrepreneur struggles desperately to save his company from bankruptcy. As financial pressures mount, he begins to tread dark paths, putting everything he holds dear at risk. In a climate of economic crisis, how far will he go to avoid the inevitable collapse?
Based on real events: No, but it depicts the difficulties of entrepreneurs during the Italian economic crisis.
The strategic lesson: The central lesson is that despite pressures to maximize profits, maintaining ethical behavior and a long-term vision is critical to corporate sustainability. The film highlights how decisions based on sound values can contribute not only to the survival of the company, but also to the well-being of employees and the community. The true measure of success lies in the ability to deal with adversity without compromising principles.
8 – All Life Ahead
Original title: All Life Ahead
Year: 2008
Director: Paolo Virzi
Cast: Isabella Ragonese, Sabrina Ferilli, Massimo Ghini
Abstract: A young college graduate enters the precarious world of call centers, where dreams and hopes are slowly devoured. In an alienating and manipulative environment, she discovers the nightmares hidden behind the apparent normalcy of modern work. As the pressures mount, the line between success and failure becomes frighteningly thin.
Based on real events: No, but offers a social critique of precarious working conditions in Italy.
Strategic Lesson: The central lesson is that professional success should not come at the expense of personal integrity and ethical values. The film invites reflection on the importance of maintaining one’s humanity and dignity in a work environment that often ignores individual well-being, highlighting the devastating consequences of a toxic corporate culture.
9 – Lord of War
Original title: Lord of War
Italian title: Lord of War
Year: 2005
Director: Andrew Niccol
Cast: Nicolas Cage, Ethan Hawke, Jared Leto
Abstract: An arms dealer builds an empire by fueling conflicts around the world. As he accumulates riches, he begins to be haunted by the deadly consequences of his actions. As the ghosts of his choices emerge from the shadows, he discovers that there is no escaping his past.
Inspired by real events: Yes, the main character is inspired by several international arms dealers. A theme
The strategic lesson: Particularly relevant at this moment in history. The central lesson is that financial success, achieved without considering social and human impact, can lead to a life of loneliness and regret. True value lies not only in profit, but also in responsibility to society.
10 – Money Monster
Original title: Money Monster
Italian title: Money Monster – The Other Side of Money
Year: 2016
Director: Jodie Foster
Cast: George Clooney, Julia Roberts, Jack O’Connell
Abstract: During a live television broadcast, a desperate investor takes a financial guru hostage after losing everything following his advice. As millions of viewers watch the event, dark financial secrets begin to emerge, revealing a disturbing plot.
Inspired by real events: No, but reflects current issues regarding financial manipulation and media responsibility.
The strategic lesson: A lesson in transparency and accountability.Lack of clear communication and the tendency to hide mistakes can lead to very major crises. In addition, the film emphasizes the importance of considering the impact of one’s actions on stakeholders, as trust is crucial to long-term success.
11 – Mr. Hula Hoop
Original title: The Hudsucker Proxy
Italian title: Mister Hula Hoop
Year: 1994
Director: Joel and Ethan Coen
Cast: Tim Robbins, Jennifer Jason Leigh, Paul Newman
Abstract: A naive recent college graduate is manipulated by the executives of a large corporation into a diabolical plan: to cause the stock value to plummet. But when his invention unexpectedly becomes a success, the plan takes a sinister turn and chaos ensues.
Based on real events: No, it is a black comedy by the Coen brothers, but it offers a satire on corporate practices.
The strategic lesson: The focus here is on creativity and innovation as engines of growth. Success comes not only from financial strategies, but also from the ability to think outside the box and embrace risk. The film emphasizes the importance of a corporate culture that values innovation, as bold ideas can lead to extraordinary results, even in difficult situations. In addition, one should not underestimate one’s human resources, and manipulating the market can backfire.
12 – The Insider
Original title: The Insider
Italian title: Insider – Behind the Truth
Year: 1999
Director: Michael Mann
Cast: Al Pacino, Russell Crowe, Christopher Plummer
Abstract: A former tobacco industry executive decides to reveal dark corporate secrets. As he goes up against a powerful corporation ready to do anything to silence him, he finds himself in a web of intimidation and mortal danger. One man’s courage can unveil the nightmare hidden behind a respectable facade.
Based on real events: Yes, the film is based on the true story of Jeffrey Wigand and the tobacco industry scandal.
Strategic lesson: His decision to speak out, despite the personal consequences, highlights how the truth can have a profound impact not only on public health but also on corporate reputation. For entrepreneurs and C-Levels, this film underscores the importance of building a corporate culture that promotes ethics and accountability, rather than short-term profit, to ensure long-term sustainability and trust.
13 – The Boom
Original title: The Boom
Year: 1963
Director: Vittorio De Sica
Cast: Alberto Sordi, Gianna Maria Canale, Elena Nicolai
Abstract: During Italy’s economic miracle, a building contractor lives above his means to maintain a lavish lifestyle. When debts overwhelm him, he receives a disturbing proposal: sell an eye for a large sum of money. Desperate, he considers the horrible choice. The nightmare of unfettered consumerism becomes real.
Based on real events: No, but it is a satire of social pressures during the economic boom.
The strategic lesson: Obsession with appearance and material success can lead to self-destructive decisions. Financial strategies must be sustainable and realistic. The film highlights the negative consequences of unbridled consumerism and the pursuit of profit at all costs, highlighting how such choices can lead to personal and social crises.
14 – Up in the Air
Original title: Up in the Air
Italian title: In the Clouds
Year: 2009
Director: Jason Reitman
Cast: George Clooney, Vera Farmiga, Anna Kendrick
Abstract: A business consultant travels the country laying off employees on behalf of companies. As his detached lifestyle is challenged by a young colleague, he begins to see the human consequences of his actions. But change comes with an emotional price that may be too high.
Based on actual events: No, but reflects business practices during periods of economic downturn.
The Strategic Lesson: This film invites reflection on the importance of human relations in the business context. The main character represents a cold and detached approach to work, and is always focused on material and professional goals. However, his evolution shows that success is not only about efficiency and results, but also about meaningful connections with people. This underscores the need to balance performance and empathy, highlighting how relationships can positively influence corporate culture and employee well-being.
15 – The Mattei Case
Available in Free Streaming on RaiPlay: Link
Original title: The Mattei Case
Year: 1972
Director: Francesco Rosi
Cast: Gian Maria Volonté, Luigi Squarzina, Gianfranco Ombuen
Synopsis: The mysterious rise and tragic end of Enrico Mattei, powerful ENI chairman, are intertwined in an international intrigue. As he challenges the great oil powers, he enters a dangerous game. Shadows lengthen around him, until a fatal plane crash raises disturbing questions. Was it really an accident or a ruthless move to eliminate a threat?
Based on real events: Yes, the film tells the true story of Enrico Mattei and the mysterious circumstances of his death.
The strategic lesson: Facing established interests without adequate precautions can be fatal. Geopolitics requires thoughtful strategies and risk awareness. A rash move can trigger uncontrollable chain reactions. Therefore, responsible leadership must always consider the long-term impact of its actions while maintaining an open and constructive dialogue with all stakeholders involved.
16 – God’s bankers
Original title: God’s Bankers – The Calvi Case
Year: 2002
Director: Giuseppe Ferrara
Starring: Omero Antonutti, Giancarlo Giannini, Pamela Villoresi
Abstract: Roberto Calvi, powerful chairman of Banco Ambrosiano, finds himself at the center of an intricate maze of corruption, mob ties and the Vatican. As he manipulates billions, dark forces begin to move against him. His suspicious death under a London bridge opens the door to a nightmare of intrigue and conspiracy. Who was really pulling the strings?
Based on real events: Yes, the film is based on the true story of Roberto Calvi and the Banco Ambrosiano scandal.
The strategic lesson: Dangerous connections and illicit financial practices can lead to deadly consequences. Transparency and ethics are indispensable in business as are robust corporate governance and effective internal controls. The absence of adequate oversight and excessive concentration of power in the hands of a few can create a breeding ground for unethical behavior. Companies must foster an organizational culture that values integrity, accountability and compliance with applicable regulations.
17 – The medicine salesman
Original title: The medicine salesman
Year: 2013
Director: Antonio Morabito
Cast: Claudio Santamaria, Isabella Ferrari, Evita Ciri
Abstract: A pharmaceutical sales representative is under pressure to meet unrealistic sales goals. Pushed to the limit, he begins bribing doctors and manipulating information. But when his actions begin to cause real harm, he finds himself caught in a web of blackmail and threats. The nightmare of his conscience becomes unbearable.
Based on real events: No, but it is inspired by corruption scandals in the pharmaceutical industry.
The strategic lesson: Ethics cannot be sacrificed for profit. Illegal practices damage reputations and can have serious legal and moral consequences. In an increasingly connected and transparent world, unethical practices quickly come to light, causing loss of consumer trust, legal penalties, and reputational damage that is difficult to recover from. The film emphasizes the importance of corporate social responsibility. Companies must recognize that their long-term success depends on the trust and well-being of the community they serve. Investing in safe and effective products, complying with regulations, and acting with integrity are not just moral obligations, but essential strategies for sustainability and growth.
What to bring to the office
From films inspired by true stories, we can learn valuable lessons that are immediately applicable in our business context. These films not only tell exciting stories, but also reveal strategic mistakes, courageous choices, and ethical challenges that every business leader may face in his or her own reality. Here are some of the key lessons you can take with you to the office to improve your strategies and the day-to-day management of your business.
- Anticipating market trends (The Big Short – #1): Anticipating signs of crisis and acting against the tide can save your company from major financial disaster.
- Importance of business ethics (Enron: The Smartest Guys in the Room – #2): Transparency and integrity are essential to avoid failure and scandal.
- Risk Management (Margin Call – #3): Making thoughtful decisions in crisis situations is crucial to avoid devastating consequences.
- Strategic Innovation (Mr. Hula Hoop – #11): Seeking innovative solutions and thinking outside the box can lead to unexpected strategic breakthroughs.
- Impact of business decisions on people (Up in the Air – #14): Taking into account the well-being of employees is critical to the sustainability of the company.
- Dangerous Connections (God’s Bankers – #16): Avoiding alliances with unethical or risky partners is vital to the health of the firm.
Social responsibility (Lord of War – #9): Business decisions must always consider the impact on society to build a lasting reputation.
