Top Streaming Shows Every Entrepreneur Should Watch in 2026

Want to be a great founder?

It might be time to open up Netflix, grab some popcorn, and learn a few lessons the hard way without actually paying for them.

Over the years, I’ve been motivated and inspired by certain streaming shows. Most recently, the final episode of Landman pulled me out of a dark place I had drifted into. It reminded me that bouncing back is what we do as founders. That moment inspired me to post on LinkedIn and ask the community a simple question.

What’s a show every entrepreneur should watch, and what lesson did you learn from it?

The Startup Club community responded with thoughtful and real discussions. 

Below is a compilation of those shows and the lessons learned straight from founders, operators, and builders who’ve lived it.

Landman

Synopsis: A modern look at the oil business where real power lives in land rights, incentives, and behind the scenes negotiations.
Lesson I Learned: Things go bad all the time, it’s how we bounce back that makes the difference. Also control your assets instead of working for someone else making them rich.
Recommended by: Colin C. Campbell

Silicon Valley

Synopsis: A group of engineers attempts to build a tech startup while navigating VCs, accelerators, competitors, and nonstop chaos.
Lesson I Learned: Building a tech company is messy, irrational, and rarely fair. Execution matters more than brilliance.
Recommended by: Colin C. Campbell

The Bear

Synopsis: A fine dining chef returns home to save his family’s failing restaurant, bringing elite standards into a chaotic environment.
Lesson I Learned: Establishing non-negotiable matters. Clear standards and principles give teams something solid to operate against under pressure.
Recommended by: Kristine Nemec

Lesson I Learned: High standards without simplicity and buy in can turn into burnout. Leadership requires knowing when to push and when to make things easier for people to succeed.
Recommended by: Jonathan Jordan

Succession

Synopsis: A media empire fractures as family members fight for control while ownership and voting power quietly dictate outcomes.
Lesson I Learned: Manage your cap table early. Influence without control is an illusion.
Recommended by: Albert Simpson

Suits

Synopsis: A high-powered law firm thrives on negotiation, leverage, and psychological strategy.
Lesson I Learned: Outcomes are often decided before the meeting through preparation and understanding incentives.
Recommended by: Bert Herrero

Hacks

Synopsis: A legendary comedian is forced to reinvent her brand to stay relevant with a younger audience.
Lesson I Learned: Even great products and brands must evolve or they fade.
Recommended by: Dana Vanhoy

Super Pumped: The Battle for Uber

Synopsis: The rise and near collapse of Uber during its most aggressive growth phase.
Lesson I Learned: Growth without governance eventually becomes destructive.
Recommended by: Michael Gilmour

The Playlist

Synopsis: The origin story of Spotify and its battle against entrenched music industry players.
Lesson I Learned: Vision is meaningless without execution and endurance.
Recommended by: Michael Gilmour

Mr. Robot Season 1

Synopsis: A gifted but unconventional hacker challenges corporate power while battling isolation and control.
Lesson I Learned: Exceptional skill creates differentiation, but leadership still requires structure and discipline.
Recommended by: Brian Piper

Mad Men

Synopsis: An advertising agency navigates pitching, client management, ambition, and cultural change over decades.
Lesson I Learned: It reminded me of my father who ran an ad agency at the same time. I learned the importance of pitching ideas and managing clients long term.
Recommended by: Colin C. Campbell

Halt and Catch Fire

Synopsis: Early tech pioneers chase successive waves of innovation from PCs to the internet.
Lesson I Learned: How to spot a technology wave early and ride it instead of missing it.
Recommended by: Colin C. Campbell

WeCrashed

Synopsis: The meteoric rise and collapse of WeWork fueled by capital, charisma, and weak discipline.
Lesson I Learned: You can screw up a good business when too much money shows up too fast.
Recommended by: Colin C. Campbell

Billions

Synopsis: Hedge fund managers and power brokers engage in high stakes psychological and financial warfare.
Lesson I Learned: Incentives drive behavior and big deals are often made quietly in the shadows.
Recommended by: Colin C. Campbell

Abstract: The Art of Design

Synopsis: A documentary series exploring how design shapes products, brands, and systems.
Lesson I Learned: It inspired ideation across multiple companies I’ve built including Paw.com.
Recommended by: Michele Van Tilborg

Julia

Synopsis: The story of Julia Child breaking into television and publishing while redefining food culture.
Lesson I Learned: She broke through traditional barriers and never stopped going.
Recommended by: Michele Van Tilborg

I will brush off my streaming subscriptions and watch the shows I missed.

These shows aren’t just about entertainment (Although I do find them a lot of fun). They’re about how power works, how businesses break, and why discipline beats hype.

Founders who study these patterns build better instincts. Founders who ignore them usually repeat them.

We are a product of who we surround ourselves with and maybe even the streaming shows we watch.

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