The world of entrepreneurship has a complicated relationship with the concept of "rules." On the one hand, certain industries have specific practices, guidelines and ideas about the "right" and "wrong" way of doing things. Send e-mails at this time. Keep your politics to yourself. Never, under any circumstances, do X, where X is the industry's ultimate faux pas.

On the other hand, being an entrepreneur pretty much requires you to break the rules at some point. After all, to be an entrepreneur, you have to be creative and forward-thinking, especially with respect to your industry and the "normal" way of doing things.

In my time as an entrepreneur, I've come to realize that sometimes the best way to treat the "rules" is to never learn them. Here are four things you gain from never learning the rules.


This one is pretty easy, but it's also pretty easy to forget. In the age of, "I have this great idea, it's like Uber but for X," it can be difficult to stand out. We live in the golden age of ideas, which means we have a lot of successful entrepreneurs to observe.

But the thing that makes them so successful is that they all did things their own way; we can't just read their playbook, because it's unique to their specific product. We have to write our own playbook, as we go.

But this is what makes us unique; it's what creates the Jeff Bezos', Steve Jobs and Bill Gates' of the world. The reason you know their names is because they're individuals in the truest sense, who never learned the rules and wound up better for it.

Improvisational Skills

Most entrepreneurs are setting out to do something that hasn't been done before, which means that there aren't always examples to look to for guidance if you're going through a crisis or dealing with a specific problem.

It's the price of being an innovator, but it's also the beauty of it all: By never learning the rules, you force yourself to think on your feet, and that's not something everyone can do.

Fun fact: I always look for sales candidates with a background in comedy or drama, because those people likely have some level of improv training. Those skills really make all the difference.


Think about the entrepreneurship as a poker game. The scariest person at the table isn't the veteran player; it's actually the novice; the one who doesn't have it all figured out yet, but is still sitting at the table and ready to play.

The novice can't be read; their moves aren't calculated, because they don't know how to calculate them. Sure, they could mess everything up--or, they could accidentally clean out everyone else sitting with them. There's a 50/50 chance of either outcome, and that's terrifying.

Same goes for entrepreneurship. My first pitches for Kiip weren't exactly home runs; I had a few slides that I had created with my HTML knowledge, and that was about it. You'd laugh at them now, but back then, they allowed investors to focus on my passion for the product, rather than how well I adhered to unspoken rules and standards.

An Open Mind

For a long time, young people's views have been heavily influenced by the people who raised them. However, millennials, and even Gen Z, are breaking that mold; we're seeing more and more young people with more progressive ideas than their parents.

This isn't to say that either way is right or wrong; the point here is that young people are, at the very least, opening themselves up to multiple points of view and belief systems, rather than accepting what has already been outlined for them as "the right way" of doing things.

By not learning the rules, you allow yourself to keep an open mind, constantly absorbing knowledge and information from a variety of sources, and utilizing it in a way that will benefit your unique journey.