Last week I had a meeting with a prospective limited partner (“Mr. X”) who is long time investor in venture capital funds. He’s extremely experienced, well respected, and has a phenomenal track record. He’s also very provocative, which always spices up a meeting like this.

As we were discussing the backgrounds of the various partners at Mobius Venture Capital, I made the statement that we all have had meaningful experience as entrepreneurs and technology executives (VP level or higher) prior to becoming venture capitalists.

X immediately asked me if I had any data to support my view that this was a good thing. He said “take the top 50 individual VCs (based on historical returns) and correlate their experience – what does it show?” I thought for a minute and ran through my head some of the great VCs I know. Before I reached a conclusion, X said “it’s random – totally random – there’s no correlation to performance.”

At first, this surprised me (I was about 50/50 in my quick mental sort when he answered for me). Then – as I thought more about it – I realized that operating experience is merely an attribute that someone has rather than an indicator of performance. Experience by itself (whether operating experience or venture capital experience) is not enough – I’ve certainly worked with some abysmal VCs who have a lot of “venture capital experience” (and I’ve also worked with some abysmal VCs who have plenty of operating experience).

I pushed on what he thought actually correlated with success. He responded that the great VCs he knew had a combination of incredible instincts honed by experience combined with the ability to quickly and accurately size up situations and draw effective conclusions. He labelled this “pattern matching” – which is a good phrase for this capability.

I think the combination is what is critical – neither operating experience or pattern matching alone is enough (e.g. “I’ve seen this before, but I don’t know what to do”).

I’m sitting in a technical advisory board meeting for one of my companies (Rally Software Development). I’m moblonging from my Danger – pretty cool (at least to me).

We’re having a great meeting. I’ve sat in on a bunch of these over the last 10 years since I started investing in (vs. running) software
companies. Often, these meetings are a complete waste of time because of some disconnect between the goal of the meeting, the group of people in the room, the facilitated process – or worse – the complete dominance of one or two people.

We’ve got 15 people in the room – 5 from Rally and 10 advisors. The
chemistry is awesome – Rally is about to go GA with the first version of their product so we’re dealing with tangibles (instead of the abstract of “what should we do, where should we go”). Management is facilitating well – leting people talk, but keeping them on topic. The richness of the discussion is noticeable to everyone involved – which causes the discussion / debate to feed on itself.

This is one of the funnest parts of this job – seeing / being involved with a group of people passionate about trying to create something new and revolutionary where six months ago there was nothing.