An Insight From Michael Dermer
Finding Your Playground
If you don’t define your own playground, AI will replace you — because AI can copy almost anything.
Your product, your price, your features, even your personality. If you’re trying to differentiate between A and B, you have already lost.
What a Playground Actually Is
The playground is a field where the rules bend in your favor — where competition turns into contrast, where the goal is not to be the best, but to be the only.
When Michael Dermer built SENT1, the company didn’t try to become the best in an existing market. Health insurers were buying separate reward solutions — diabetes here, smoking there, maternity somewhere else. SENT1 showed them they needed one enterprise-wide platform covering every condition, and created a new market: rewards for healthy behavior. Once that frame was defined, everyone else was stuck selling something the market had outgrown. SENT1 didn’t compete in the category. It defined it.
The Five Tactics for Finding Your Playground
Don’t Penetrate Markets — Define Them. “If you can Google it, it’s not a Playground. You don’t win by competing. You win by defining.”
Entrepreneurs die trying to capture 1% of somebody else’s huge market — but 1% of a crowded market can still be death. Before they existed, ride-sharing, home-sharing, and bottled water were markets worth zero. Uber wasn’t a better taxi company. Airbnb wasn’t a better hotel. They created new fields.
If your market size looks like zero, you may be onto something.
Insight + Risk. “See What They Don’t — And Show The Risk of Not Knowing.”
Everyone says their product is better, their customers love them — that’s noise. You become indispensable when you reveal something the customer didn’t see, and show the risk of not knowing it. Insight without risk is trivia. Risk without insight is fear. Together they create urgency and gratitude.
A local election: a challenger asked what he’d do first said “fix the pothole on 5th and Collins.” The polished incumbent replied he’d fix every pothole in the city. The challenger answered: “There is no pothole on 5th and Collins. I’ve lived here my whole life.” One line exposed the risk of electing someone who didn’t know the community.
Put Things That Don’t Go Together. “If You Want to Create a Playground, Combine What Doesn’t Belong — Until It Does.”
Most entrepreneurs add sprinkles to the same ice cream cone — new features, new delivery, new packaging. AI can copy those sprinkles overnight. A real playground is created when you collide two worlds that seem alien.
Hamilton combined an overlooked founding father with hip hop and became one of the highest-grossing musicals ever. The Savannah Bananas collided baseball with a circus, a comedy show, and a TikTok spectacle — they didn’t make baseball better, they made it unrecognizable, unforgettable, and theirs.
Positioning Is More Important Than Product. “Founders spend 80% on product. 20% on Positioning. Flip it and flip your fate.”
Nike does not win because every runner believes it makes the most technically advanced shoe. Nike sells victory. The product can be copied — meaning lives in the customer’s mind.
80% positioning. 20% product. 100% survival.
Apples vs. Oranges. “Put competitors in one bucket — and stand in your own.”
While other car makers sold speed, style, and performance, Volvo sold safety. It did not polish the same apple. It became the orange.
When everyone sells apples, the orange does not compete. It owns the shelf.
“The most dangerous place is the middle of the field, where everyone tells the same story to the same customer. Ideas don’t die because they are bad. They die because they are not different enough to matter.”
Stop competing. Start creating. Don’t fight for a slice — bake a new pie and name the flavor. Find the playground where no one else is playing. Then own it.
Find Your Playground With TLE
Playground Report
A researched, data-backed report scoring your company’s actual whitespace — where a playground already exists for you, and where it doesn’t yet.
Entrepreneur Survival Guide
Finding Your Playground is the first of the Six Weapons entrepreneurs need to survive and thrive in the age of AI.
Sidekick Consulting
A senior partner in the trenches for CEOs of $5M–$50M companies — including the hard call on where your real playground is.
The Learning Community
One place for the answers, tools, and trusted support founders need to define a playground instead of competing in someone else’s.