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How To Break the Rules to Make It As a Startup

Following the rules? If you’re an entrepreneur, the answer is likely no. The very nature of creating a self-motivated business means looking at the typical career path in an entirely new light. It’s a bold, risk-taking, exhilarating move, and the founders behind brilliant startups probably wouldn’t have it any other way.

Of course, not every rule is made to be broken. Many are based in solid logic—and stem from painful trial and error. As Matt Rissell, TSheets CEO, said in a recent video, “Don’t break the rules. Unless you have to break the rules. Then, go ahead and break them.”

Here are four rules to consider breaking to make it as an entrepreneur.

#1: Be a Rebellious Teen

So maybe you can’t go back in time, but a recent 30-year study from a nationally representative sample of 12,686 Americans “found that successful entrepreneurs have to be smart, have high self-esteem and be well-educated; but they also need the attraction to risk. Those who turned out to be the best entrepreneurs often had a history of being rule breakers in their teenage years.”

What did these teens get into? The typical nefarious activities that are the stuff of parental units’ nightmares. However, grown-up entrepreneurs earned 41% more per hour on average than similar salaried workers. It’s rebellion—originally without a cause, later with a real business purpose—you can take to the bank.

#2: Fail Harder

Successful CEOs everywhere are redefining the concept of failure. The winners-always-win attitude might work for some, but it’s only when stuff hits the fan and flies off the handle that entrepreneurs find what mettle they’re really made of—then discover how to move their company forward in ways they couldn’t even imagine at the outset.

This means going to market with a less-than-perfect product and revising in real time, with real customers, as in the Lean Start-Up model. This means rethinking the core of your product and customer base when you find what might not be working, and radically revising your business scope and purpose when necessary. This means being mentally prepared for the inevitable gut-wrenching downturns, and deciding in advance how you will negotiate the rough times with a clear head, a non-blaming attitude, and a winners-never-quit persistence.

#3: Fire Yourself

When you wear all the hats in a company, as entrepreneurs inevitably do in the beginning, it’s hard to lead effectively. It’s a myth that a CEO should serve as the be-all and end-all for the long haul.

“When you’re first starting out, you have to perform in any number of roles. So do as much as you can, but as you grow, the best thing to do is interview yourself,” Rissell advises. “Literally. Sit down. Put an empty chair in front of you. Start talking to yourself. If you wouldn’t hire yourself for the position, fire yourself as soon as possible.”

He continues: “Start firing yourself from the things you are worst at, then like the least, until you get yourself at your sweet spot. Then, I believe you can lead from any position in the company. You can be a rockstar software engineer and be the CEO. You can be in charge of marketing and be the CEO.”

#4: HQ in the Middle of Nowhere

Silicon Valley. Boston. New York City. The draw of headquartering in the standard startup locales is obvious and appealing, but the high costs of living and the competitive, even sometimes conformist, nature of doing business in big places presents downsides too.

TSheets started in Eagle, Idaho. To many, this means the middle of nowhere, but to the company’s growing team of talent, the quality of life can’t be rivaled. The cost of living is low. The outdoor recreational opportunities are abundant. The pace of life is more laid back, without slowing down the energy and passion of the company one bit.

Austin Kleon, author of Steal Like An Artist, offers this tip, “Geography is no longer our master.” The world wide web opened up a world of opportunities for business owners. So start where it feels right, and then you can really go places.

The ultimate lesson? Be a rule breaker, then go on to rule the world.





Contributor at Fundera
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