Why Are Entrepreneurs So Weird?

The only way to succeed — with a startup or anything else you pursue — is to understand what makes you different and be faithful to it.

Written by Joe Procopio
Published on Apr. 06, 2022
Why Are Entrepreneurs So Weird?

Over the past two decades, I’ve been lucky enough to be a repeat startup founder, and I’ve also had the opportunity to work alongside some of the top serial entrepreneurs in the country. And there’s one thing I can say about every single one of us. 

We’re all a bunch of weirdos.

It’s something that neither surprises me nor is it off-putting in any way. In fact, taking my own weirdness into account, I not only naturally gravitate towards curious people, but I’ve come to realize that I seek them out. 

I’m not going to go so far as to declare that the stranger the character, the better the entrepreneur. But I have concluded that being strange definitely helps — once you admit it and come to terms with it, that is. 

Let’s get weird.

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Define ‘Weird’ 

Look, I’m not talking clown shoes or a fake British accent. I’m not talking about being weird for the sake of attention. I’m actually referring to those innate-but-awkward qualities that make good entrepreneurs: the qualities that drive them to swim upstream against a current that most of the world calls normal. Because “normal” is just another way to say “status quo.”

Exhibit A: Elon Musk. Dude is weird. 

Sometimes Musk will sell flamethrowers to the general public or challenge dictators to a duel on Twitter. Other times, he’ll let slip even more questionable tendencies that often get him into trouble. But he always eventually skates on his public mistakes. Why?

It’s probably because those same questionable tendencies are also what wrangle the cats in his brain to bring to reality ideas like electric cars and space-travel — ideas that his contemporaries can only drag until he gets them working. People generally understand this about him. 

It’s not out of bounds to believe that money is what allows Musk to comfortably perch on a more extreme end of entrepreneur’ weirdness — still definitely a far cry from anti-social wack-job — but most of us are much closer to the center of the spectrum. Without the money (and the podium and protection that money provides), it can be difficult to embrace our own weird tendencies, let alone lean on them.

But whether we’ve earned a safety cushion or not, if we don’t embrace what makes us different, aren’t we just perpetuating the status quo?

Why Entrepreneurs Need to Be Weird

  • To make it as an entrepreneur, you have to risk ridicule, rejection and ultimately even failure.
  • Even seemingly buttoned-up Fortune 500 leaders didn't get where they are by following the status quo.
  • The only way to succeed is to understand what makes you different and be faithful to it.


The Inevitable Weirdness Check

There’s an interesting moment that happens on almost every intro call I have with a serious entrepreneur or wannabe serious entrepreneur. At some point, usually between 10 and 15 minutes into the call, the person I’m talking to will preemptively apologize for something that they either think, do or are about to say. 

And the next thing they tell me is always something that makes me like them more. 

It’s always something not meant for mass consumption and definitely not fodder for a first impression. It might have to do with owning up to an odd hobby. It might be about not being able to live up to some standard of professionalism or even maturity. It might be about a random event in their life that impacted them so forcefully that they decided to start a business. 

It doesn’t have to make sense. It rarely does. And as an aside, it also implies a level of trust and comfort, which I take pretty seriously. 

The fact is, even the most committed entrepreneurs want their business to be perceived as a legitimate, serious business — one that could someday fit neatly among the ranks of the Fortune 500. Those are successful companies that look a certain way, act a certain way and maintain a certain status quo, from the outside, at least. They certainly didn’t get to a billion-dollar valuation being run by people like, well, people like you and me.

Except they did.

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Weird Is the Road Less Taken

These are the folks I gravitate to the most, not because of any sense of altruism or social good but because how they feel is how I still feel every single time I start turning an idea into something more than an idea. In my past, I’ve been ignored, laughed at and even scolded, in private and in public, by people I respect.

In fact, the first time that didn’t happen, it gave me the confidence to reject every other path to success except my own, and I sold my company a couple years later. I never had to pretend to be someone I wasn’t. I never had to apologize for the things I did, thought or was about to say. 

I realized I didn’t want my business to look or act like anyone’s else’s business. I wanted it to be successful for what it was and for what I (weirdly) believed it could be.


Embrace Your Weird

This is where someone else would tell you that leaning in to what makes you different is the surefire way to startup success. I’m not going to do that, because it isn’t true. 

But I will tell you that the only way to succeed — with a startup or anything else you pursue — is to understand what makes you different and be faithful to it.

You can line yourself up to walk, talk, act, think and look like any of those CEOs running any of those Fortune 500 companies. You might get far, but you won’t get to where you want to be. Success following someone else’s formula is empty success. It’s connecting dots. It’s painting by numbers. It’s a paycheck.

And listen: I wouldn’t deny anyone that kind of success. Ever. We all need to pay the bills and some of us, myself included, are very good at the pattern recognition and stylistic adoption necessary to fit in. I just decided I didn’t want to work so hard at it anymore.

If you want to truly fulfill the ideas and ideals that make you an entrepreneur, you have to risk ridicule, rejection and ultimately even failure. But when you do, you’ll realize you’re not alone. In fact, you fit right in — just by standing out.

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