08. Why the Best Startup Moves Don’t Always Make Sense at First

Every founder wants to get it right. The pitch. The product. The plan. But sometimes, what makes the difference isn’t what you do better. It’s what you dare to do differently.

In 1980, something unusual happened during a chess championship in Sweden. On one side of the board sat Anatoly Karpov, the world champion. He was known not just for his skill, but for his discipline, his structure, and his absolutely unshakable consistency.

Karpov didn’t just play chess — he embodied the system. He represented everything that was elegant and expected about the game at the highest level.

Across the board sat Tony Miles, an English grandmaster, equally titled but far less celebrated. He wasn’t there to be feared or admired. He was the underdog. Brilliant, yes, but not the name anyone expected to win.

Now, I’m not a chess expert. But I know enough to understand that at the top level, the opening move is not just technical — it’s symbolic. It’s tradition. There are unspoken rules about how the game is supposed to begin. It’s a rhythm that players respect, a kind of ritual that carries weight beyond the board.

But Miles didn’t care about rituals. After Karpov made his first, conventional move, Miles responded with something completely unexpected. It wasn’t reckless. It wasn’t random. But it was unconventional enough to break the entire tempo of the game. According to those who were there, Karpov was visibly rattled. And that almost never happened.

He lost the match. The world champion, defeated — not by better technique, not by deeper preparation, but by someone who simply refused to follow the expected path. Not because he wanted to provoke, but because he saw a different possibility.

That fascinates me. Because that moment on the chessboard wasn’t just a game. It was a metaphor for everything that happens in startups. It was a reminder that sometimes, the most powerful move you can make is the one that looks strange in the beginning.

Let’s step away from the chessboard for a moment and talk about what this means in the world of entrepreneurship. Startups are full of unwritten rules. You’re expected to have a certain pitch deck. You’re told to follow a specific fundraising roadmap. There are best practices for everything — for your website, your onboarding, your tone of voice, even your pricing model.

But here’s the truth that no one says out loud. Those best practices might get you accepted. They might help you look like everyone else. But they rarely help you build something extraordinary.

What Miles did on that chessboard — what made him win — wasn’t brilliance in the traditional sense. It was his ability to ignore what wasn’t working for him. He didn’t follow the script because the script was never written for him in the first place.

That’s the trap so many founders fall into. They follow the expected path. They do what the books say. They copy what worked for someone else. And they hope that by following the formula, they’ll end up with the same success.

But that’s not how it works. Success, especially in startups, rarely belongs to those who play it safe. It belongs to the ones who see the board differently. The ones who risk doing something that might not make sense to others — but feels absolutely right to them.

And let me be clear, this isn’t about being contrarian for the sake of it. This isn’t about trying to be edgy or disruptive just to stand out. This is about trusting your way of thinking. About knowing when to trust the fundamentals and when to break them.

Because sometimes, the move that changes the game doesn’t come from the most experienced person in the room. It comes from the one who isn’t afraid to move first — and differently.

Now imagine this not as a chess match, but as your next pitch, your next product, your next decision. You’re sitting across from the market — from investors, advisors, or even your own inner critic. And they’re all expecting you to play a certain move. To act like every other startup in your space. To pitch what they’ve heard a hundred times before.

But what if that expected move is exactly what holds you back? What if the boldest thing you can do is not follow the pattern?

You don’t need to be reckless. But you do need to be real. You don’t need to shock people. But you do need to surprise them with something that is so deeply yours, they couldn’t have seen it coming.

Because that’s what great founders do. They build things that don’t just fit. They build things that shift.

And if you’re building something right now, and it feels unfamiliar — if people are telling you it doesn’t quite make sense yet — maybe that’s not a warning. Maybe it’s a sign that you’re playing your own game.

Not everyone will see it yet. That’s fine. You’re not here to be understood right away. You’re here to move first.

And just like Miles, you don’t need everyone to clap. You don’t even need them to agree. You just need one moment of clarity. One move that breaks the rhythm. One decision that makes the whole board shift.

And when that happens, you don’t need validation. You’ll know.

You’ll look up, just like Steve Jobs did when his team showed him something he didn’t believe in until he saw it with his own eyes. And you’ll say:

“Show me that again.”

Because that’s when you’ll know it’s time to build.