My daughter and son are lobbying me for their annual pilgrimage to HersheyPark next weekend.  If you haven’t been there – think chocolate factory, on a heat sinking Dessert Shield tarmac, meeting countless upside down, inside out and water shooting devices of mass terror and destruction.  My idea of a party…… Just the thought of an upside down roller coaster makes my stomach flipflop.

Meanwhile, I am living the dream of VChood -- working with my portfolio companies, talking with new entrepreneurs, and living first hand the ups and downs of entrepreneurship.  It is absolutely amazing how quickly a start up company’s prospects can change.  Each day is different from the next.  I realize that it really is the grown up equivalent of an upside down super soaker vertical climbing rocket coaster.  So, if I hate roller coasters, why do I like working with start ups?

And, more to the point, why do entrepreneurs subject themselves to this?

A good friend of mine describes being an entrepreneur this way: “Being an entrepreneur is riding home in your car at the end of a day thinking that you can’t possibly be more screwed than you are at that moment, and then finding out in the morning that you were wrong.”  He says this with a smile, having been part of a number of successful start ups.  Another friend describes working with a start up as riding a roller coaster where you know the dips are coming you just don’t know whether the dip is a large one or a small one because the hill is too steep.  And she says this with a smile too.

So, what are these folks?  Masochists?  Certifiable lunatics?  Thrill seekers?  And, what does that make me, since I invest with these people……

Clearly what roller coasters and entrepreneurship have in common are the thrills (or terror) that they can create.  But, I don’t think that means that entrepreneurs are thrill seekers, looking for a quick burst of sensation and the resulting endorphin rush.  Rather, I suspect that it’s something more subtle.  I think it is the longer term sense of accomplishment that comes from quelling a fear, or mastering a situation.  In other words, it’s not the roller coaster that’s exciting it’s the riding that matters.

I’m reminded of the face on my daughter when she rode an upside down coaster for the first time.  Her face at the top of the loop was frozen in what looked to me like primal fear.  Yet, as she bounded off the coaster her first words were “that was fun, I want to do it again.”  There was a palpable air of accomplishment about her.

And, this is where I see the overlap.  Entrepreneurs have in common a number of traits.  One of the most prevalent (if not the most prevalent) is that entrepreneurs are “doers”.  They live to make things happen, to shake up the world around them; in other words, to conquer situations and master them. That’s why when they talk about the ups and downs of being an entrepreneur they don’t complain (mostly), instead they smile, shake their heads and look forward. 

There is another point to make, however.  The best entrepreneurs are able to moderate their desire for accomplishment and mastery.  Sometimes the best path forward is not to change things, but to sit tight. And, sometimes taking a risk just isn’t worth it.  The same way that you would not want to spend the day at an amusement park with someone that wanted to continually ride the roller coaster, you don’t want to invest with someone that is always looking to shake things up.

The intangible balance between facing and mastering change, creating change for its own sake, is probably one of the largest personality criteria VCs apply to evaluating entrepreneurs.  My best advice is that if you are a person that wants to be in constant motion, and always mastering changes, you should have as a business partner someone who values continuity.  And, if you value continuity above all others – well you probably should consider carefully starting a company.  But, if you do, find someone who will balance your desire for the status quo.

For my part, although I will try to convince my daughter that I get sufficient thrills from being a VC, I suspect that some time over the next week I will find myself upside down hanging from a roller coaster seat.  But, only in moderation…..