Image by AMWRanes via Flickr
To be honest, I don't know. I've been back and forth on the issue on various panels and I kind of cannot make up my mind. On one hand you want to have your investors to have on hands experience, however on the other hand, having to deal with someone who was successful in the past and forces you to do things in their way doesn't really help.In the past I really looked up at the people who successfully built companies and wanted them to be close by. Over years I learned that this is the wrong criteria. Being successful in the past is not only a function of ability, there are a whole bunch of other factors as well. Some of them have nothing to do with their ability to be a good investor.
One of my best experiences with investors is with those who haven't built big and successful companies, but are rather humble in a way that they really work hard with the founder to built something big and meaningful. Even if they are investment superstars.
So I think it boils down to this: Investors that you want to work with are: intelligent, well connected and respectfully proactive.
You don't want to work with arrogant individuals that sit in shiny offices, come late to the meeting and never switch off their phones during conversation. You owe it to yourself and your business not to take this kind of nonsense.