Andy Weissman’s blog has the tagline “Maximizing the serendipity around you.” It’s a good philosophy. I think one of the simplest ways to do this is to ask people lots of questions when you meet them. I’m surprised how often people fail to do this. Besides being good manners, it’s also an efficient way to learn about the world and sometimes make important discoveries and connections.
About 6 years ago, when I was working at Bessemer as junior investor, I was at a dinner with a group of friends and acquaintances. The guy sitting next to me was a business school student who spent most of the dinner talking about how he was trying to get a job in venture capital. He never bothered to ask me what I did for a living and I never mentioned it.
Now, I wasn’t a particularly important venture capitalist, but getting a job in the industry is all about meeting as many people who work in it as you can. The fact that he happened to be sitting next to one was potentially serendipitous – had he only bothered to ask questions.