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Back in the Game

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Written by Chris Kelly (
Back in the Game

Since leaving the so-called “dark side” of venture capital last year to jump back into the startup game, I’m come across a variety of people who’ve inquired about a transition they seem to view as scary and risky. The most persistent questions have come from associates and other young “investment professionals” still figuring out a career path.  I’ve always been surprised at how few of them actually seriously considering joining an early stage startup.  A disappointing amount of them seek refuge in business development roles at larger, public companies, slink back to their earlier life in investment banking, or move downstream into private equity.

So, whenever I get the “What should I do?” question over email or at happy hours, I always say one thing.

“Don’t be afraid to get your hands dirty.”

Of course, it’s not as easy or fun as it sounds.

To an outsider, this might seem silly.  Venture capitalists and entrepreneurs seem so tied at the hip that a VC associate could tell a mortgage broker that he “does startup stuff”  without raising any eyebrows.  In reality, though, the difference between watching an entrepreneur get something done and actually getting something done is quite stark.  At best, the relationship between an investor and an entrepreneur resembles that of a football coach and player; at worst, that of a sports writer and player.  And face it, guys, no one actually likes sports writers.

If I reflect on what my “hands dirty”  advice actually entails, I suppose it’s 2 things:

  1. Rip off the band-aid. Just pull the trigger and hop to the startup side of the fence. Don’t hang on to your junior principal role for 3 more years if you know you’ll be in the same position then as now.  Yes, you’ll take a lower salary.  Yes, your hours will be much longer.  Yes, banging out wireframes isn’t as cozy as hanging out at the “VentureBucks” on Sand Hill.  Yes, you may have to look for another job in 18 months if things go south.  And yes, your MBA may not be respected by the database engineers on your team.  But hey, you moved to Silicon Valley to take a chance at hitting it big, right?
  1. Grow, baby, grow. Probably the best advice I’ve heard on this topic is to simply look for fast growth environments.  Growth isn’t necessarily tied to size – whether you’re 4 geeks in a garage or 200 hipsters in Soma, if you’re moving fast, you’re moving fast. A fast growth environment lets you punch above your weight class and be stretched to do many things at once.  I think the diametric opposite of solving for growth is solving for “cool.” I feel bad for people who start or join startups in categories that impress new friends at bars and look sexy on LinkedIn, but don’t seem to have a viable chance of turning into a real business.

Of course, there’s never a template answer to anyone’s career choice, but I think these 2 mindsets can serve as solid rules of thumb.

In the meantime, say hi to everyone at the VentureBucks for me.

Chris Kelly does Marketing for, San Francisco startup that’s building the “Weight Watchers for debt” to solve one of the largest social problem in America – debt stress.  He was previously an associate at Matrix Partners in Menlo Park, Calif and the co-founder of  Send him your thoughts at or @chriskelly on Twitter.  And no, he’s not running for Attorney General of California…


Written by ahzietsman

June 21, 2010 at 11:23 pm

Posted in Venture Capital

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