Break The Rules! These 11 Founders Did

What happens when you blow off the traditional wisdom of starting a business? Take it from these 11 entrepreneurs: Things can work out even better.

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There’s an old saying that floats around the internet, always popping up in those collections of inspirational phrases: “Learn the rules like a pro so you can break them like an artist.” Did Pablo Picasso say it? The Dalai Lama? Alexander McQueen? All have been cited as the source, but whatever—its origin doesn’t matter. It endures because it’s true.

Entrepreneurs are rule breakers, too, but the smartest among us know that you don’t go smashing windows just because. We don’t break rules for the fun of it. We break rules when we understand the systems that created those rules—and then, with careful thought and steely resolve, we can see bending that system to our will. We learned the rules. We know what we’re doing. And that’s why, when the time is right, we don’t follow them.

On the following pages, we offer a celebration of rule breakers. And unlike that quote above with the cloudy origin, these words of inspiration are fully attributable: Eleven entrepreneurs tell us how they built their businesses by ditching the old ways. Learn from them—and then, when you see fit, go do something else entirely.

Chris Stang

COFOUNDER AND CEO/ The Infatuation

RULE BROKEN/ Follow what your industry does

In 2014, when most digital publishers knew only one way to build an audience, Chris Stang and his cofounder, Andrew Steinthal, chose a very different path: They started sending text messages.