10 Must-Watch Movies for Startup Founders and Entrepreneurs

Jan de Vries · 2026-07-28

Looking for inspiration and entertainment while traveling or unwinding during your summer holidays? We've got you covered. We've compiled a list of movies that offer an engaging look at entrepreneurship, innovation, ambition, and the realities of building a business. From dramatized true stories and corporate rivalries to fictional accounts of founders and industry disruptors, these titles combine entertainment with useful lessons about leadership, negotiation, resilience, and decision-making. So, put your feet up, get the popcorn ready, and settle in. Here is our latest watchlist for startup enthusiasts, entrepreneurs, and anyone interested in the people and ideas behind the business world. ### Air (2023) Air follows Nike executive Sonny Vaccaro as he pushes the company to sign a then rookie basketball player named Michael Jordan to an unprecedented endorsement deal. Despite Nike trailing Adidas and Converse in basketball, Vaccaro convinces the company's leadership, and Jordan's family, that betting everything on one athlete could redefine sports marketing. The film centers on persuasion and strategic decision-making rather than basketball itself. As such, it offers an excellent look at negotiation, conviction, and calculated risk-taking. The film shows how identifying a unique opportunity and structuring a win-win partnership can create enormous long-term value, making it especially relevant for entrepreneurs, marketers, and business leaders. ### The Apprentice (2024) The Apprentice chronicles the early business career of Donald Trump in 1970s and 1980s New York, focusing on his mentorship under influential and notorious lawyer Roy Cohn. As Trump builds his real estate empire, he learns the tactics of negotiation, branding, media manipulation, and aggressive deal-making that come to define his public persona. The film provides an insightful look at personal branding, negotiation, reputation management, and the power of perception in business. It also serves as a cautionary tale, showing how ambition and relentless competitiveness can fuel success while raising difficult questions about ethics and leadership. ### Flamin' Hot (2023) Flamin' Hot tells the disputed story of Richard Montanez, a Frito-Lay factory worker who rises through the company after developing an idea inspired by Mexican-American flavors and pitching it to senior executives. The film follows his efforts to overcome professional barriers, gain recognition, and turn a product concept into a commercial opportunity. The film explores innovation from within a large organization, entrepreneurial thinking, workplace ambition, and the importance of understanding underserved consumers. It also highlights how personal experience can shape product development, while offering a broader lesson in persistence, internal advocacy, and communicating an idea effectively. ### Bank of Dave (2023) Based on a true story, Bank of Dave follows UK businessman Dave Fishwick as he attempts to establish a community-focused bank designed to support local residents and small businesses. His plan brings him into conflict with established financial institutions and regulators, forcing him to navigate a system that appears resistant to new entrants. The film examines social entrepreneurship, access to finance, regulatory barriers, and the role of trust in banking. It presents business as a tool for community development, while showing how purpose-driven leadership and local knowledge can challenge conventional industry models. ### Dumb Money (2023) Based on true events, Dumb Money follows Keith Gill and thousands of everyday investors who rallied behind GameStop stock after believing it was massively undervalued. Their collective buying triggered one of the biggest short squeezes in history, challenging hedge funds and exposing tensions between retail investors, Wall Street, and trading platforms. Beyond the headlines, the film illustrates the power of communities, social media, and collective action in modern markets. It's a reminder that sometimes the little guy can win, and it highlights the importance of conviction and research in investment decisions. ### Why These Movies Matter for Entrepreneurs Each of these films offers something unique for anyone building a business. You'll find lessons in: - **Negotiation and persuasion** - Air shows how to structure deals that create value for everyone - **Branding and reputation** - The Apprentice reveals how perception can be more powerful than reality - **Innovation from within** - Flamin' Hot proves that great ideas can come from anywhere - **Purpose-driven business** - Bank of Dave demonstrates how mission can drive success - **Community power** - Dumb Money shows what happens when people unite around a shared belief These aren't just entertaining stories. They're case studies in human behavior, risk-taking, and the sheer determination required to build something meaningful. So grab your popcorn, press play, and let these films inspire your next big move.