Unfiltered #8 – The Irrationality of Entrepreneurship


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From the CEO

Unfiltered #8 – The Irrationality of Entrepreneurship

I have done some stupid shit in my life.  There have been many questionable decisions.  But, there have also been just some flat out stupid choices.  For instance, and just to set the bar here….  In my early twenties, I lived on a boat in Stock Island, FL near Key West.  Now, this was the Stock Island of 25 years ago, not the Stock Island of today.  I lived on Shrimp Boat Row and “worked” as a salvage diver.  Another diver named Stu lived on the boat with me for a year or so.  Stu did a lot of drugs.  Stu and I partied pretty hard.

One day, Stu’s Prince Albert got hung up in the velcro of his board shorts.  When he went to open his fly, he ripped it right out.  Always there to help someone in need, I scooped up blood-covered Stu and the Prince Albert ring off the deck and loaded both into my Jeep Wagoneer.  We sped off in the hurry you would imagine – but not to the hospital.  No, we went right to this guy on Stock Island that did piercings and tattoos.  See, Stu had a date that night and he wanted his tackle right.  But, this isn’t the stupid part of the story.

As I was sitting with Stu, and the piercer was trying to find enough real estate to reinstall the Prince Albert, I got bored.  So, I had the guy tattoo me while I waited.  That is the stupid part of the story. 

And because dumb ideas seem to stick around awhile, a couple of years ago as I drove through Stock Island with my wife and kids, we passed the hovel where all of this went down and I recounted the story in vivid detail while my 6 and 8 year olds wondered who their real dad was and my wife held her head in her hands.  Stupid always keeps giving.

Flash forward a number of years to 2006.  I had decided to leave my really good job in Washington DC, move to Vermont (a landlocked mountainous state), and start Greensea (a subsea robotics company).  When I resigned, a manager at the company and the HR Supervisor looked me dead in the eye and said “This is the stupidest thing you will ever do.”  Man, were they ever wrong.  They had no idea how low that bar was.

So many entrepreneurs follow their announcement to go out on their own with a quick explanation that almost sounds like an apology: “Well, I am not getting any younger”, “Now is really the right time, before I have kids”, “It might not work, but it is just me right now”, etc.  I call this the Entrepreneurial Apologetic Explanation (EAE) because it is clear so many entrepreneurs hear the same thing I did and stammer out the same thing I did.

The thing about entrepreneurship is that it is irrational.  If it was rational, everyone would do it.  Most of us have good jobs, or at least the ability to have good jobs.  Those of us that feel the calling are typically creative thinkers, independent, not afraid to fail, action-oriented, and carry around enough gumption to get a lot done.  Great employees, really (except for the bit that we don’t work for others very well).  But we have chosen to leave the calm seas and clear destination of employment behind in favor of a rough, perilous, and unknown passage towards an imagined land far, far away.  No matter how you slice it, it is irrational.  But it is not stupid.

In fact, not following that calling would be stupid.  It would be ignoring a deep need that is hard to explain.  It would be turning the page on a good (or bad) idea that is begging to be attempted and pleading to see the light of day.  Those of us that have been there know, it was something we just had to do.

The stigma of entrepreneurship is quite a dichotomy.  On day one for the entrepreneur, the unsaid judgement by our peers is so prevalent that we have to offer a quick explanation and apology with the announcement of our venture.  When we are successful, we are heralded as Entrepreneurs (big ‘E’ this time).

I experienced all of this back in 2005 and 2006 when I first started planning the launch of Greensea.  Besides the aforementioned encounters, I offered the Entrepreneurial Apologetic Explanation to my banker, our real estate agent, my attorney, strangers, peers, and probably whoever else asked the question dreaded by so many new entrepreneurs: “What do you do.”  The few people to whom I never had to explain were my wife and her family. They always believed in me and always supported me.  So it goes for many of us.

I enjoy working with entrepreneurs striking out on their own.  I like helping them think through financing and corporate strategy and I enjoy being their cheerleader.  What many don’t understand is that entrepreneurs were called to do what they do.  When you ask them years later, after success or failure, “What motivated you to go out and start something”, they have a hard time explaining it.  This isn’t a decision made out of boredom while you wait for a friend to have his ripped out Prince Albert put back in.  For many of us, it is not really a decision at all – it is just something we have to do.  I know it first hand.  I have seen it in the faces of the starters I have worked with over the past decade.  I have even seen it in the faces of Greensea employees who have come into my office to resign because the calling became too great.  (By the way, you have to check out https://ramblemaps.com/)

So no.  Starting Greensea was not the stupidest thing I have ever done.  Not even close.  In fact, it was one of the best things I have ever done because I listened to the calling within me, didn’t turn the page, and went for it.  Entrepreneurship is not an apologetic action.  Irrational for those that have not experienced the calling but unavoidable for those of us who have.

So, to those thinking of being a starter.  Go hard and go all the way and don’t ever apologize.

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Greensea Systems, Inc.

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