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Different styles
Successful investors come in very different styles. John Doerr is very salesy and relationship-oriented, while Michael Moritz is introverted and an incredible thinker. Benchmark's partners show the same range: Peter Fenton and Bill Gurley think about business and approach it very differently.
The curiosity trait
Some great investors are quantitative and some qualitative, some people-oriented and some market-oriented. What shows up consistently is curiosity. When there is something they do not understand, or a mistake they made, they dig in: they talk to people, ask questions, pull information, and try to form a point of view about what they missed.
Competitiveness
The other trait is competitiveness. They want to win, and they want to be the best.
Why does venture capital reward outlier picks?
Most startups return little or nothing, while a few return many times a fund's size. A loss is capped at the amount invested, but a win has no ceiling, so investors hunt for outliers. Peter Thiel wrote in Zero to One that the best investment in a successful fund equals or outperforms all the others combined.
How was Benchmark's partnership set up?
Benchmark was founded in 1995 as a small partnership in which the partners share equal economics. The structure was meant to keep partners focused on the companies rather than on rank within the firm. Bill Gurley, a Benchmark partner, led the firm's 1997 investment in eBay.
Why do some firms publish the deals they missed?
Reviewing misses is one way investors form a view about what they overlooked. Bessemer Venture Partners publishes an Anti-Portfolio page listing well-known companies it passed on, including Apple and Google. The page treats those misses as lessons rather than secrets.