Streaming Shows Every Entrepreneur Should Watch

In recent years, streaming platforms like Max, Netflix, Amazon, and Apple have revolutionized how we consume content. Binge-watching has become a cultural phenomenon. As an entrepreneur, I always look for valuable insights hidden within these shows—lessons that can inspire and shape how we lead, grow, and, in some cases, mitigate failure.

Here are my 10 ‘must-watch’ streaming shows every founder should check out to help sharpen their entrepreneurial skills:

10. Shōgun

A new historical drama exploring Japanese politics and culture, based on the acclaimed James Carvel’s 1975 book of the same name, takes place in the 1600s.

Lesson I learned: Startups must be adaptable and frugal — qualities that define both samurai and entrepreneurs navigating uncertain landscapes.

9. Halt and Catch Fire

A deep dive into the early days of the computer and internet industry.

Lesson I learned: Understanding how to catch a tech wave is key. Watching this show reminded me of my own experience launching internet businesses, chronicled in the book Start. Scale. Exit. Repeat. from coming up with the idea to launching in a high-growth market. If you want to take it a step further, check out Geoffrey Moore’s Crossing the Chasm, which also explores the importance of identifying and capitalizing on trends and paradigm shifts.

8. Empire

A gripping drama about the chaotic world of the music industry.

Lesson I learned: Working with family can be a double-edged sword — sometimes a strategic advantage, but often a source of conflict.

7. Super Pumped: The Battle for Uber

A dramatized look at Uber’s early days and its controversial founder, Travis Kalanick

Lesson I learned: Barriers are meant to be broken. Just because a law exists doesn’t mean it can’t be challenged—especially if you can get the voters behind your vision.

6. Billions

A high-stakes drama where politics and business collide.

Lesson I learned: The best person doesn’t always win. Success often comes down to who you know rather than just raw talent.

5. WeCrashed

The rise and fall of WeWork and its visionary but reckless founder, Adam Neumann.

Lesson I Learned: In the book, Start. Scale. Exit. Repeat., I coined the term “Silicon Valley Disease”—when a company raises too much money, loses focus on efficiency, and chases growth at all costs. This show is a cautionary tale of that exact phenomenon.

4. Shark Tank

Entrepreneurs pitch their businesses to a panel of investors.

Lesson I learned: Too many entrepreneurs give away too much equity too early. Why trade 50% of your company’s profits for just $50K? It’s like paying a lifetime tax on your business.

3. The Dropout

The shocking story of Theranos and its founder, Elizabeth Holmes, who promised to revolutionize blood testing.

Lesson I learned: There’s a fine line between vision and fraud. It’s one thing to be a bold optimist but another to knowingly sell something that isn’t possible.

2. The Profit

Marcus Lemonis invests in struggling businesses and helps turn them around.

Lesson I learned: Turning a business around is often easier than you think. The key? Making tough decisions in the best interest of the company — not your friends or family.

1. Silicon Valley

A hilarious yet insightful take on tech startups and their challenges.

Lesson I learned: It takes a community to build a startup. While I run an incubator that’s more structured than the one in the show, the reality remains: no founder succeeds alone. It takes a village to raise a startup.

Final Thought

Will watching these shows make you a successful entrepreneur? Of course not. But if you take the time to reflect on their messages, you’ll find lessons of encouragement, caution, and insight—helping you navigate the wild world of entrepreneurship.

Entrepreneurship is a trade, just like any other trade, and learning that trade is the key to success. These shows may be entertaining but they are also valuable insights into how to start, scale, and exit a startup.