Cheaters always Win and Winners always Cheat

Ross Simmonds

I’m a competitive person.

I play to win no matter what the game is.

No matter if were playing a game of scrabble or a game of dodgeball; I play to win. And while its often a fault of mine because I’m not a fan of losing – its one thing I cant change. I love competition, I love competing and I love to win.

The one thing however about competition that I cannot stand is those who cheat.

Those who break the rules that games are ultimately found upon. I’m talking about the guy who slides a couple $500 bills under the board during monopoly.

When Cheating is Ok!?

While this mentality is applicable to games and sports; when it comes to business I say – Cheat, cheat and cheat some more. Break the rules that have been created by the old guys and write your own. Go against the norm and do something we’ve never seen before. Because in the rule breakers who find themselves being the most successful. The rule breakers are the guys who are worth talking about because they went against the norm and did something interesting.

Small Cheats are Great Feats

Today I came across a post from Luke Wroblewski discussing a  unique registration form built by Jeremy Keith for his audio sharing site, Huffduffer. Take a look,

When we talk about cheating it doesn’t have to be something huge. Sure, Amazon cheated when they decided they would have free shipping.  Sure, Starbucks cheated when they made coffee something classy. But cheating can be as small as this new design on Huffduffer.

According to Luke, this small cheat supports this claim,

Ron and his team ran some A/B testing online that compared a traditional Web form layout with a narrative “Mad Libs” format. In’s testing, Mad Libs style forms increased conversion across the board by 25-40%.

Implementing small cheats throughout your business model will result in you becoming more comfortable with going against th enorm. It will ultimately allow you to look at business more like art rather than simply a way to make some cash. However, cheating usually helps you achieve your goals.

Remember the saying?

Cheaters never win and winners never cheat.


Remember the Remix:

Cheaters always win and winners always cheat.

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About Ross Simmonds

Ross Simmonds is a digital marketing strategist who has worked with everything from Fortune 500 companies to startups to drive results using digital marketing and technology.

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This post was mentioned on Twitter by TheCoolestCool: New Post: Cheaters always Win and Winners always Cheat – I’m a competitive person. I play to win no matter what the…

Lester Bryant III
11 years ago

I believe that you may be confusing “cheating” with breaking the rules. They are not the same thing. Cheating is what Enrons accountants did; cheating is what brought us a global economic melt down. Breaking the rules has however always brought us innovation and creative advances.

11 years ago

I'd argue that breaking the rules is actually a part of cheating if anything. What Enrons accountants did cannot be considered cheating. You see, cheating takes place when you do something that gives you an advantage over your competition. In video games its described as “creating an advantage beyond the bounds of normal gameplay, usually to make the game easier.” Thus, Its when you go against what everyone else is doing and start making your own rules. Enron didn't make any new rules. Enron didn't come up with a new strategy. All Enron did was lie to the masses for… Read more »

Lester Bryant III
11 years ago

We might want to agree to disagree on this one. The first 2 transitive verb definitions of “cheating” in MerriamWebster are: 1 : to deprive of something valuable by the use of deceit or fraud2 : to influence or lead by deceit, trick, or artificeIf cooking your books to inflate stock prices and hide the real condition of your company is not cheating, I'm not sure what is? As well, what Enron did gave them a great advantage over their competion for a long period of time. I also believe that lying and cheating are very often the same thing.… Read more »

11 years ago

Good points, If were going by definitions then we will come across hundreds around the web. At the end of the day this post isn't about the word or the definition. Its about pushing the limits and expectations that have been established in an industry and going against the norm. Whether we call it breaking the rules, cheating or just plain being innovative – were still talking about the game changers. I appreciate the thoughtful comment Les. Its always good to have someone to challenge my ideas and thoughts. I do think that we will have to agree to disagree… Read more »


[…] to avoid failure is to play it safe and stick to the way things have always been. They refuse to cheat – they refuse to break the rules. And as a result they are just another boring company […]


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