To those who dare

The winning decisions that didn't stand a chance

As an entrepreneur, you’re going to find yourself torn between following the tried-and-true methods of your industry and making singular decisions that nobody else has the guts to take.

It’s a balance.

You need to learn from the best—surround yourself with people who have mastered their field, listen to their advice, absorb best practices. You’ve got to build a strong foundation before you can truly start thinking outside the box. But at the same time, if you want to truly disrupt, to achieve something remarkable, some of your decisions will need to go against everything you’ve been taught.

The irony is that while people love to praise innovation, most won’t have the nerve to make truly counterintuitive decisions. This is where entrepreneurs distinguish themselves. Sure, it’s easy to follow the patterns, to apply the lessons and play by the rules. But the most successful companies—think Uber, Airbnb—made their mark by crossing the line. They didn’t follow the script. When Airbnb sent photographers to capture listings, it wasn’t scalable; it wasn’t even logical. But it was brilliant. Uber broke rules, challenged entire industries, and created something entirely new. These decisions, that at the time seemed insane, are exactly what changed the game.

But how do you take those singular decisions the right way?

It starts with being open-minded. You can’t be closed off, convinced that you already know it all. The best entrepreneurs ask questions, they seek feedback, they listen carefully to those around them. They surround themselves with experts, not to follow them blindly, but to challenge their own thinking. You need to let yourself be challenged if you want to find that singular path that no one else sees. And once you’ve absorbed all that knowledge, only then can you decide to deviate from it.

It’s important to remember this: in venture, the best investments rarely come from consensus. It’s the same in entrepreneurship. The bold, singular decisions often come from one individual or a small group of people who are willing to go against the grain. The key is understanding that not every crazy decision will work out. In fact, most won’t. But the ones that do are the ones that make history. People remember the wild bets that paid off, not the ones that didn’t.

The reality is, most experts will resist change. They’ll tell you your idea is ridiculous because it doesn’t fit into their pattern, their experience. But that’s exactly why you need to have the courage to take those singular decisions. The experts didn’t have the ambition or the guts to start their own company, so they’ll often find a hundred reasons why your new idea won’t work. Don’t be discouraged by their skepticism—learn from it, but remember that they’re defending the status quo. Your job is to challenge it.

Taking these singular, counterintuitive decisions won’t just make you stand out—they’re the decisions that can redefine industries. Yes, there will be failures along the way, but those few bold moves that succeed? Those are the ones that will carry you far beyond what others ever thought possible.