5 Movies and Shows Every Aspiring Entrepreneur Should Watch Part 1
- Ciara Bolden
- Jul 18
- 3 min read
Inspiration can come from many sources, but for entrepreneurs, movies and TV shows that champion business and innovation can provide unique insights and motivation. From fashion moguls to media pioneers, here’s a curated list of five must-watch titles (plus a bonus!) that will ignite your entrepreneurial spirit and teach valuable lessons along the way.
1. The Devil Wears Prada

Lesson: Embrace resilience and adaptability in a competitive industry.
This iconic film starring Meryl Streep as the formidable Miranda Priestly and Anne Hathaway as her assistant, Andy Sachs, is more than just a story about the fashion industry. It’s about resilience, growth, and understanding the dynamics of working with strong personalities. Entrepreneurs will recognize the importance of learning from mentors, even if their style is tough, and adapting to challenges with creativity and grit.
Takeaway: Sometimes, the most difficult environments can teach you the most valuable lessons about professionalism and perseverance.
2. She Did That (Documentary)

Lesson: Highlighting the journeys of Black women entrepreneurs.
This powerful documentary showcases the stories of Black women breaking barriers in business and entrepreneurship. Directed by Renae Bluitt, She Did That dives into the realities of building a brand while navigating systemic challenges. It’s a heartfelt and empowering film that resonates with women looking to turn their passion into a purpose-driven business.
Takeaway: Representation matters. The documentary serves as a reminder that your journey as an entrepreneur can inspire others.
3. The Bold Type

Lesson: Balancing ambition, friendship, and personal growth.
This series follows three friends working at a fictional women’s magazine, Scarlet, and tackles everything from ambition to social issues to navigating workplace politics. While it’s focused on the media world, entrepreneurs can learn from the bold risks the characters take—both professionally and personally—to build meaningful careers.
Takeaway: Success often requires stepping outside your comfort zone and challenging the status quo.
4. Girlboss

Lesson: Learn from both successes and mistakes.
Inspired by the true story of Sophia Amoruso, founder of Nasty Gal, Girlboss explores the highs and lows of building a business from the ground up. While Sophia’s story doesn’t follow a traditional trajectory, the series shows how creativity, hustle, and a willingness to fail can fuel entrepreneurial success.
Takeaway: Every entrepreneur faces setbacks, but success lies in learning from mistakes and persevering.
5. Martha (Documentary)

Lesson: Reinvent yourself and your brand.
This documentary delves into the life of Martha Stewart, the ultimate lifestyle mogul. From building a media empire to bouncing back from setbacks, Martha’s story is a masterclass in reinvention, branding, and determination. Entrepreneurs will be inspired by her ability to pivot and remain relevant in an ever-changing market.
Takeaway: Reinvention is a crucial skill for long-term success in business.
Bonus: Minx

Lesson: Recognize niche opportunities and take bold risks.
Set in the 1970s, this series follows a feminist who launches the first women’s erotic magazine. While unconventional, Minx is a fun and insightful exploration of finding your niche and taking bold risks to disrupt an industry.
Takeaway: Sometimes the most unconventional ideas are the ones that revolutionize the market.

Why These Titles Matter for Entrepreneurs
Entrepreneurship isn’t just about starting a business; it’s about finding inspiration, learning from others’ journeys, and staying resilient through challenges. These movies and shows highlight essential traits like innovation, adaptability, and self-belief while reminding us that success comes in many forms.
So, whether you’re working late on a business plan or brainstorming your next big idea, grab some popcorn and let these stories fuel your entrepreneurial journey.
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