I have a huge suspicion through out the years that VC’s tends to invest in entrepreneurs with big personalities. Those that can withstand the glare of partner meetings and talk non-stop on the phone for hours with a VC they barely know.

Buried in a great profile of Michael Moritz by The Guardian is this priceless paragraph.

Backing start-ups is high risk and Sequoia has had its failures, the most famous being Webvan, which hoped to create a business offering delivery services to retailers, and eToys, the internet toy retailer; both collapsed. While Moritz blames the demise of the former on trying to expand too quickly, he puts other mistakes down to backing the wrong entrepreneur: executives with guns in their drawers, drug habits or a tendency to try to mow down co-founders in their car.

WOW . . . I actually only know one or two person in my whole life that I would consider capable of such a behavior. To have that many (atleast 3?) in the portfolio must mean that his selection criteria might bias his group toward that kinda of behavior.

In many cases, people with big personalities can become somewhat bi-polar. They angry easily and obsess endlessly. They are often emotionally unstable, and filled with self doubt. On the other side of the coin, their tirelessness and paranoia is perfect for the improbable world of startups.

I guess in the end, if you are looking for homeruns, you go with a home run hitter who hits 50 HR a year but has a .230 batting average than go with a 5′ 7″ shortstop who slap singles all day. The strike outs on a slider in the dirt are built into the business model . . .