What Syria and Fistfights Can Teach You About Taking Risks

I’ve run a startup with two other cofounders and dozens of contractors for nearly three years on only $131,000. Before that worked for the United Nations in Damascus, Syria. Before that I traveled around the Middle East, Africa and Asia on money earned as a bike messenger. Throughout most of that time I also spent nearly everyday getting beaten up at a mixed martial arts gym.

Risk, and a lean mentality, have been good to me. The lessons learned riding a bike in Boston, traveling the developing world, dodging gunfire in collapsing states and getting into fights are directly applicable to the risk taking mindset required for success in the startup or non-profit game. Below are the five rules I’ve created in as many years of traveling, fighting and CEO’ing to help me better understand risk and better apply lean strategy. I am far from a guru, and actually even pretty far from a startup success, but these rules have kept me and my company afloat for this long.

Only someone with a gun can tell you what to do.

If someone is trying to tell you that you can’t do something, but they are not currently in possession of a loaded firearm, then they are merely offering a suggestion. I learned this one in Egypt a few weeks after the revolution. Lots of people trying to tell me what to do, only a few actually had the power to enforce their will. In running a company I hear ‘no’ a lot. Investors, competitors, partners, advisors, lawyers, journalists, employees, co-founders, contractors and even interns all tell me no, and then tell me to do something I don’t want to do. The only person I have to listen to is the law. When you start a company, you are inherently doing something that nearly everyone thinks is going to fail. If most people didn’t think it was going to fail, there would already be lots of people doing it. The most valuable criticism you can find comes from the ones that believe in you, but not in your idea. The skill is in convincing the people without guns that your way is better.

Strength and size are powerless against speed and flexibility.

This holds true in the business world, on a bike and in a fight. Speed and flexibility are wasted if you wait for all the data or for perfect timing. Startups can beat corporations because they only rely on assumptions or basic metrics. Bikes beat cars in traffic because they never stop moving, even if that means running reds or riding on the sidewalk. A light, small fighter strikes and strangles before the bigger fighter can land a power blow.Startups outmaneuver corporations, bikes weave between cars, and the most dangerous fighters only weigh 160 pounds. Quickness and the ability to change direction always win. But executing quickly and pivoting require a fanatical dedication to being lean and a willingness to pay for risky behavior.

Risks should be contextualized by fear, and then taken despite that fear.

My hiring process at the UN was unique. I completed no application, had no formal interview and was offered no training. I bought my tickets to Syria, took a cab to the UN office the day I arrived, told security I left my keycard at home and ignored the front desk girl’s protests. I walked straight into the office of the department head I wanted to work for, told her I had come all the way from Texas for a job with her, and started translating her Arabic newspaper into English as a proof of my skills.

That sounds pretty badass but in actuality I had carefully weighed my options and established a long list of contingency plans in the same way a startup sounds badass but really is a precise orchestration of risky maneuvers punctuated by pre-planned pivots at specific milestones. Fear of failure helped shape that risk and more importantly it drove the planning process for reacting intelligently and quickly if any step produced failure. The build-measure-learn mantra of lean strategy only works if you use fear to rationally shape strategy, and then ignore that nagging timidity when its time to take a risk.

Everyone has a plan until they get punched in the mouth.

As Mike Tyson famously articulated above, bad things happen when you take risks. I’ve been hit by four different cars in Boston, been shot at in Egypt, gotten Giardia in Malaysia, crashed a motorcycle in Nepal, been knocked out in the gym on more than one occasion, and have had to come to investors and advisors with sickeningly poor quarterly financials.

What separates a risk taker from someone who just makes poor decisions is the ability to intelligently progress despite overwhelmingly negative external stimuli. The true point of Tyson’s oft quoted soundbite is that he possessed a freakish ability to perform calmly and accurately while vastly more experienced, and physically superior opponents battered him. As Dharmesh Shah, the oracle of the Boston angel investing scene says, ‘at least once a year, something will very nearly kill your startup.’ A great boxer and a great founder agree: getting punched in the mouth is the easy part, punching back in a controlled manner is what makes a champion / millionaire.

Without durability, this is all meaningless.

Our offices have been set up in a co-working space for about a year. In that time I have watched four startups and one non-profit set up shop, work for a few months (or even just a few days) and then fail. All of these companies had more intuitive concepts, more sophisticated launch strategies, more attractive market opportunities, and more experienced (and more intelligent) founders than my company. They failed because they gave up.

A few had founders that had grown fat on Bain and McKinsey paychecks and quivered at the thought of writing $0 on an income tax statement. One had a founder who had bounced from Ivy league to MIT to Ivy league racking up degree after degree and shattered once the false-confidence giving splint of academia was removed. One had a three way public shouting match between the founders involving thrown coffee and broken Mac products after their first sale collapsed. One company simply evaporated one morning, leaving all their supplies and vacating without a goodbye after they discovered an equally young competitor in San Francisco carving into their market.

The unifying information here is the same: these companies took risks, measured the results, the data added up to ‘failure’ in the founders minds, and while they had the skills, intellect and training to pivot or fight back, they capitulated out of shame. You have to be smart and well trained to run a startup or a non-profit. Most smart, well trained people do not have much experience with humiliating failure. More importantly, most smart, well trained people’s first reaction upon being presented with massively negative results is to move on to the next idea instead of jumping headlong into an apparently doomed venture.

So in effect, this has been my experience: Don’t listen to anybody unless you want to. Measure and learn but do it faster than you think is too fast. Let fear shape your strategy but not your execution. Risk will make you a success but not before it burns everything you’ve built to the ground at least once. There will come a time or an entire year when shame and logic will dictate you should quit; if you quit on your dream, someone else will build it for themselves.

Want to learn more? Visit us here.

Want more insights? Sign up for our newsletter