Be Smart Enough to Be Naive Enough
There’s a saying I keep coming back to: be smart enough to be naive enough to not know what you can’t achieve.
I first heard it at an Under Armour all-hands in 2010. Kevin Plank stood on stage and reminded the room that reaching $1 billion in annual revenue, once the audacious goal, had been done. The next target, he said, was dethroning Nike. No hedging. No qualifications. Just conviction.
Under Armour was still the hungry underdog then. Hearing Plank treat the company’s naivety as a competitive advantage, not a liability, was something I didn’t forget.
That phrase has carried me through some of the biggest, most improbable bets of my own life.
When I set out to build Orion’s Kin, what eventually became a TV show, a media company, and a full storytelling platform, I had no background in media production. No formal training. No investors lined up. No reason, on paper, why it should have worked.
What I had was a conviction that stories matter. A belief that people are hungry for authentic human narratives about resilience, adaptability, and growth. And a refusal to let the quiet voice in the back of my head win. The one that says this is too big for you.
Looking back, I’m certain of one thing: if I had been too smart, I never would have started. If I had spent enough time analyzing the market, the barriers, the capital requirements, the odds, I would have talked myself out of it before I took a single step.
The naivety wasn’t ignorance. It was a choice to not let knowledge become a cage.
That’s the line worth understanding. You need to know the rules well enough to bend them without letting them become walls. You need to see the risks clearly without letting them freeze you. You need enough awareness to navigate and enough belief to ignore what you’re supposedly not allowed to attempt.
Valor Cycles worked the same way. I wanted to build the first 3D-printed carbon fiber road racing bicycle to win a stage of the Tour de France. I didn’t have decades of manufacturing experience. I had prototypes made from PVC pipe and printed lugs that were, generously speaking, not pretty. But they gave me real data. And real data, even from ugly prototypes, is how you find out whether the thing you believe is actually true.
That’s what naive enough actually means in practice. It means you start before you’re ready, you learn in the friction, and you let the work tell you what’s possible rather than deciding in advance.
The people who build things that matter are rarely the ones who were certain they could succeed. They’re the ones who didn’t know they were supposed to fail, or knew and went anyway.
So the question worth sitting with: what have you shelved because you got too smart about it? Where did analysis replace action? What would you attempt if you gave yourself permission to not know what you can’t do?
The first step is usually the one you’ve been overthinking.