Rules; Break Them or Follow Them?

I was reading my friend Jimmy Odom’s post on his startup.  It’s crypto-focused and he bootstrapped it. He’s doing well.  Jimmy broke some rules when he launched, and he paid a price.

I say this with all sincerity, I’d never experienced such raw hate and absolute vitriol from Chicago’s tech “leaders” as I did on that day. One “leader” went so far as to attempt to shout from the rooftop of a globally circulated business publication calling my partners and me “bozos”. In that piece, he went on to beg anyone who bothered to pay attention to him to NOT do business with us. This was not the only event nor the worse and while I won’t expound on the others here, one thing that became concisely clear was they were not isolated. This came from a city that promotes a public narrative of how forward-thinking it’s “leaders” are and how much they champion it’s tech entrepreneurs.

Happens when you break rules.  Great entrepreneurs always upset apple carts and break a few eggs.  Remember Steve Jobs speech about “here is to the crazy ones”?  Yup, used it for branding at Apple but he really did feel that way.  He drove over the speed limit constantly and always parked in the handicapped spots. But, he broke more rules than that.  In the short run, it hurt him.  In the long run, it paid off for the company.  I am not sure Apple breaks a lot of rules today but I digress.

I remember learning about blue laws and they certainly seem dumb.  I think it’s safe to ignore almost all of them.

Your parents are integral to your understanding of laws.  They raise you and teach about acceptable behavior so you can navigate civil society.  But, those rules are all subjective, and not objective.  They can vary from society to society, culture to culture, vary over time, and even vary from state to state.

Personally, I am not a big rule follower.  Being an independent commodity trader will tell you to break rules.  But I follow some.  For example, you will do better by buying a no-load mutual fund that replicates the S&P 500 over the long term than trying to pick bottoms and tops and single stocks.  Math reinforces the rule.

Some rules have a bigger purpose. Let me explain.  When I was at the Air Force Academy, we were learning how to drill.  I thought drill was a total waste of time but I understood why we had to learn it.  We marched to lunch every day and there were parades and we had to look good for the people that came to the Academy to see their tax dollars at work.

But I was wrong.

One day an upperclass cadet ripped into my entire flight.  We were totally screwing up.  Drilling in the hot Colorado sun at altitude with white gloves under arms was not pleasant.  We were all tired from the adjustment from civilian life to Academy life.  My ears were getting sunburned since I had my head shaved and they hadn’t seen the sun since the 1960s. I was ready to break some rules.

He looked at us all tersely and said, “You know why this makes a difference?”  Of course, none of us were bold enough to open our mouths and answer, we’d done enough push-ups for one day.

He went on,” Imagine yourself flying in formation.”  Not hard for a lot of us to do since most of us wanted to be in a cockpit someday.  He continued, “You are on an attack.  The leader of the formation shouts over the radio, ‘Break right’.  Instead of breaking right, you didn’t listen to your drill instructor.  You broke left because it doesn’t matter right?”  We looked at him nakedly and unsure of what was going to come next.  He finished, “So, you broke left.  You just killed everyone in the formation.”

Silence.

My flight won the drill competition for the entire Academy later that summer.  We got coke and popcorn as a reward and it was great.  Sometimes it’s the simple things.  We learned to follow the rules of drill.

Some rules are in fact there because they have a higher calling.  So you have to do your research before you actively break them.

But, if you want to be an entrepreneur, break them.  You will ruffle lots of feathers. That’s a sign you might be onto something.  When the big companies come to try and regulate you, you know you are onto something real because it threatens their business model.

Usually, the best ideas are also stupid.  But, it would be really cool if they really worked.

Breaking rules also include “entrepreneurial ecosystems”.  Most of the time the self-appointed leaders of an ecosystem have their interests at heart, not yours.  The elites anoint them.  Then they carry on and cheerlead.  Many have no real stake, like their own cash or a meaningful amount of cash, in the game.  In many cases, it’s more about their legacy.

All I know is my whole life if I followed the rules, I wouldn’t be where I am.

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