title: “Testing the limits of the world around you” date: 2025-12-16T22:25:03-0800 draft: false description: “” tags: [“founders”, “entrepreneurs”, “risk”, “self-awareness”, “shamelessness”, “self-reflection”] categories: [“thoughts”] ShowToc: true TocOpen: false ShowReadingTime: true ShowBreadCrumbs: true ShowPostNavLinks: true ShowWordCount: true

To be a successful founder, there are many traits one needs to embody: adaptability, discipline, perseverance, grit, humility, curiosity, integrity, and the list goes on.

Some of these come naturally. Others are learned. And even the ones you’re born with usually still need to be cultivated, strengthened, and refined.

One trait I never struggled with is shamelessness.

I get nervous. I get anxious. I care what people think. But growing up, I was pretty shameless. I’d say or do silly things, just to have fun.

It took me a while to learn how to be shameless without being rude or disrespectful. That required self-awareness, and self-awareness did not come naturally to me.

In this podcast about Lee Kuan Yew, Ben Wilson shares a quote that stuck with me:

At Raffles College, he does extremely well. He kind of goofs off and doesn’t pay much attention. He’s a prankster. And I’ll just highlight this, that if you want to find really great talent, look for the pranksters. Thomas Edison was a prankster. Steve Jobs was a prankster. John Wooden was a great prankster. Alexander Hamilton was something of a prankster. The list goes on. It’s a great way, for whatever reason, to spot talent. Very intelligent, very capable people. You know, I think what it is is they like to test the limits of the world around them and therefore they enjoy pranks.

The line I keep coming back to is the last sentence:

They like to test the limits of the world around them and therefore they enjoy pranks.

That feels like the underlying behavior of a certain kind of founder.

Rules. Beliefs. Practices. Regulations. Constraints. Ideas. Unspoken social scripts. I’ve never been particularly impressed by the status quo. If you have no shame, there’s less friction between curiosity and action. You’re more willing to poke at reality and see what moves.

And if you’re willing to live with the consequences of breaking a rule, you might discover that the rule wasn’t as important as you were taught.

Being a prankster requires risk tolerance. Entrepreneurs tend to have more of it. That’s why they push. They test. They stress the system.

Change requires stress.

To change the world, you have to test its limits, break what’s brittle, and rebuild what’s better.

Be shamless. Test the limits of the world around you. Think Different.

I finally understand what Steve meant.