Observations: The Paradox of Being a “Smart” Venture Capitalist

My last post, and observation of business & government students, was popular enough that I think I’ll share a second one here.   This is an observation that I’ve shared with a large number of people in the past seven years, as part of my greater set of take-aways on working in venture capital.

I worked for Atlas Venture from 2001-2002 as an Associate, and during that time I had the chance to observe quite a the interesting paradoxes that make up success in early-stage venture capital.  This particular observation is about the paradox surrounding being seen as “smart”.

In the short term, venture capitalists often look smart by saying “No”.  But in the long term, venture capitalists can only look smart by saying “Yes”.

This applies generally to new people joining the industry, regardless of level.  New associate, venture partner, general partner.  Venture capitalists deal with exceptionally long cycles.  It takes the better part of a decade to build most businesses, and it can take that long to really determine who in venture capital is doing the job, and who is just playing the part.

In the long term, the metric is simple: how many successful entrepreneurs & companies did the venture capitalist fund & help build to extraordinary outcomes.

In the short term, people are desperate for any tangible signal that will predict the long term.   Unfortunately, in many cases, the short hand for this becomes evaluating their critical thinking about risks and issues on every pitch.

As a product leader, I see this behavior play out on a regular basis outside of venture capital as well.  More experienced product managers will review the work of junior product managers, and will prove their capabilities by highlighting problems.

They don’t realize that they will never be great by pointing out flaws.  They will be great by translating that knowledge into solutions for other people’s products, as well as leading their own innovative initiatives.

I could always tell when a general partner, whether at Atlas or another firm, was “ready to fund”.  You would see their posture in meeting shift radically from finding ways to say no to finding ways to say yes.

Not surprisingly, my fondest memories of venture capital surround the start-ups where I said yes.