Compounding Curiosity: The Skill Nobody Teaches
Why curiosity compounds like interest, how it's made me a better builder and operator, and why most people stop being curious too early.
Key Points
- Curiosity is a learned skill that compounds exponentially over time, not a fixed trait
- Cross-domain curiosity (combining insights from different fields) creates unfair competitive advantages
- Most people stop being curious after school because they’re trained to find THE answer, not keep asking questions
I’ve built 23 businesses in the past decade. I haven’t gotten smarter. I’ve gotten more curious.
That might sound like semantics, but it’s the difference between chasing novelty and building a real advantage. Curiosity is like compound interest—the early returns feel invisible, but give it five years and you’re unstoppable.
The Philosophy-to-Operator Pipeline
When I was 22, I was a philosophy major. When I was 26, I was building software. When I was 28, I started a marketing agency. When I was 30, I was helping other founders scale their businesses.
Each jump felt completely unrelated. Philosophy to tech made no sense. Tech to marketing made even less sense. But here’s what I know now: every field taught me something that made the next field easier. Philosophy taught me how to ask better questions. Tech taught me how systems work. Marketing taught me how to think about human behavior. Business taught me how to connect all of it.
That’s curiosity compounding.
Albert Einstein said it best: “I have no special talents. I am only passionately curious.” He wasn’t being humble. He was being honest. The skill that matters isn’t being the smartest person in the room. It’s being the most interested person in the room.
The Latticework of Mental Models
Charlie Munger, Warren Buffett’s partner at Berkshire Hathaway, talks about building a “latticework of mental models.” You can’t just know business. You have to know psychology, history, math, physics, economics, and systems thinking. When you understand how different domains work, you see patterns that specialists miss.
That’s what curiosity does. It builds the latticework.
When I started Rotate (our marketing agency), I wasn’t the best designer or copywriter. But I was curious about how great designers thought, how great copywriters worked, and how those two disciplines connected to business metrics. I could see when something was both beautiful and effective because I’d spent years understanding both sides.
When I invested in Point Party (a credit card loyalty rewards newsletter), I wasn’t a fintech expert. But I was curious about financial incentives, newsletter distribution, and community building. I understood why it would work before we built it.
Curiosity connects the dots. Specialists see dots. Curious people see the connections.
Why People Stop Being Curious
Here’s the problem: school trains you out of curiosity.
From kindergarten through college, the entire system rewards one thing—finding THE right answer. You don’t get points for asking interesting questions. You get points for answering the test correctly. We spend eighteen years teaching people to converge on a single solution, and then we wonder why nobody thinks in original ways.
By the time you enter the working world, curiosity isn’t a reflex anymore. It’s a choice. And most people stop choosing it.
They read their industry’s top publications. They go to their industry’s conferences. They talk to people in their industry. And slowly, they become very knowledgeable about one small corner of the world. Which might be fine, except that the most valuable insights come from adjacent fields.
The best marketing ideas often come from psychology. The best product insights come from customer service. The best business strategy comes from understanding history. But you only see those connections if you’re curious enough to wander into those domains.
Building the Curiosity Habit
Curiosity isn’t magic. It’s a learnable skill, and like any skill, it compounds with practice.
Here are the three things that work for me:
Read widely, not deeply. I used to think I had to become an expert in everything. Now I read one great book per domain—one on psychology, one on history, one on marketing, one on systems thinking. You don’t need to be an expert. You just need to understand the core ideas.
Talk to people outside your industry. Some of my best business insights have come from conversations with architects, teachers, and musicians. They think differently because they solve different problems. Borrow their thinking.
Ask “why” one more time. When something breaks or succeeds, don’t stop at the first explanation. Dig deeper. Why did that customer churn? Why did that feature work? Why do people buy this? The second and third “why” are where the real insights live.
The Compounding Effect
Here’s what happens when you practice curiosity consistently:
Year 1: You feel like you’re reading a lot and learning, but it mostly feels inefficient. You’re bouncing between topics. Nothing connects yet.
Year 3: You start seeing patterns. You notice that the marketing principle you learned connects to the psychology concept you read about last month. The connections start multiplying.
Year 5: Curiosity becomes an unfair advantage. You spot opportunities that specialists can’t see. You understand why something won’t work before you even try it. You ask better questions in meetings because you’ve borrowed frameworks from six different fields.
Year 10: You’re operating in a completely different category of effectiveness.
This is why integrators—people who understand all the parts of a business—tend to become the best operators and leaders. They’re not smarter than specialists. They’re more curious. They’ve spent more time understanding how sales connects to product, how product connects to operations, how operations connect to strategy.
The book “Thinking in Systems” by Donella Meadows talks about this—that the ability to see systems and connections is the real leverage point in any organization. Most people see isolated problems. Curious people see systems. Systems thinkers see leverage points.
The Compounding Advantage
The unfair part about curiosity compounding is that it’s not immediately obvious.
If I’d asked you in 2014 whether understanding philosophy would make me better at business, you’d say no. If I’d asked you in 2016 whether my marketing background would help me understand software, you’d say probably not. If I’d asked you in 2018 whether my software knowledge would help me advise 20+ founders, you’d have said that’s too diversified.
But compound anything long enough, and it becomes invisible—because it becomes normal. I don’t think of myself as applying philosophy to business. I just make better decisions. I don’t think of myself as combining marketing and software. I just see patterns others miss.
That’s the compounding effect. The work you do to build curiosity today won’t pay off for five years. But when it does, it’ll feel effortless.
Start Small
You don’t need to overhaul your life. You need to add one small curiosity habit.
Pick one domain that’s adjacent to your work but not your work. Start with one book. Ask one person in that field how they think about problems. Notice one connection. That’s it.
Do that consistently for six months, and you’ll be surprised by how many dots connect. Do it for three years, and you’ll operate in a different league than people who stuck to one discipline.
As Richard Feynman said, curiosity is a gift. But like all gifts, you have to decide to use it. Most people don’t. That’s exactly why the ones who do end up building things that matter.
The skill nobody teaches in school is the skill that compounds the longest. So teach it to yourself.