Bill Gurley — the very sage Benchmark partner and incidentally perhaps the tallest VC in the game (6’9”) — was interviewed by Om Malik recently. I encourage you to watch them, but two clips in particular, about thinking about risk that I want to particularly highlight in adjacent posts:
First, he notes that a venture capitalist’s reputation might be created by just one investment. That creates a tension, since you need experience – a period of developing pattern recognition and “rules” – but then the one investment that defines your career might be one that defies those and other rules. Listen to the first clip on the link above and then here is an excerpt of my rough transcript:
Waiting around to hit the one out of 10,000 pitches and getting it right; that’s a tough game to play and it’s really easy to miss…and a lot of the ones that become the breakout players break any rule set that you have created…
So, you have a rule set through experience, discussion, learning, but then you also need the wisdom, instinct, and courage to break those rules in order to truly hit the grand slam. This strikes me as the tension in truly doing anything great — knowing the rules, but also knowing that you need to break certain of them sometimes because ultimately it’s not a formula.