Idea, Execution…and Gumption

Posted on November 5, 2009. Filed under: Uncategorized | Tags: , |

It’s 10:43pm.  A former colleague of mine is sitting across the table from me in the Think Coffee on Mercer and West 4th Street.  We’ll call him Jim (for privacy’s sake).  The rings under his eyes are visible.  He hasn’t cracked a smile in two hours, and he can’t get onto the internet.  My man is beat.  To understand the gravity of his situation, perhaps it would be helpful to share a little context on the events leading up to this evening.   If I look at the economic trajectory of his 30 years on this planet, it would look something like the letter n.  He came from nothing and clawed his way to a prestigious undergraduate degree, a high paying job on wall street, a fund of funds career, and a stint at a top tier venture capital firm.  He is a worker and always has been.  By the time I met Jim at General Catalyst Partners, he had worked over 25 jobs, ranging from waiter, to beer guy for the Arizona Diamondbacks, and everything in between.   I watched this guy support himself, his older brother, and his mother, quietly and selflessly, and it was clear that he had been doing it for a long time.  So General Catalyst was the arch at the top of out letter n, but not without a fair bit of spilled sweat.

Fast forward to the sharp little point on the bottom right of our n.  Tens of thousands of dollars in debt, cancelled a first date with one of the most beautiful women I’ve ever seen because he couldn’t buy her a drink, and you might ask yourself how did he get here only 18 months.  Drug addiction? Gambling problem? Unexpected child?  Nope…entrepreneurship.  He has been financing a relatively involved software build on savings, and credit cards, and a bit of friends and family money.

So, to the present.  You might think the dark rings under his eyes are attributable to the countless hours an entrepreneur must spend creating something from nothing.  And no doubt, those hours are adding up, but these rings are dark.  Why?  Because Jim just took a full time wait job, on top of his full time Founder job, less then a month from his product launch.  He doesn’t have another choice, New York is an expensive place to live while your bootstrapping something.  Jim could break, and get a job that pays $200,000 tomorrow, instead of running himself ragged like this, but he is driven by a burning desire to fix a problem that needs fixing.  It has consumed him to the point where he has sacrificed his wealth, his health, and any sembilence of a personal life for his company, and in 3 weeks he’s going to get to see the flop.

I wrote yesterday about the qualities Michael Jackson embodies that I wish for in a VP of Product, and today I put forth Jim as an example of what I look for in a founder, or a co-founder for that matter.  With the last company I started, I picked my co-founder almost entirely on character (and of course competence and intelligence), because starting a company is fucking hard.  You need to run through wall, after wall, after wall, and keep on running, no matter how hard it gets.  People often site idea and execution as the two factors that dictate the success or failure of a startup.  Perhaps I’ll tack on gumption as a third, and say if you have the drive of my buddy Jim (and you’re the MJ of consumer internet products)…holler, I’m working on something kickass…

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at (p.s. i don’t use spell check…deal with it)


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