In my opinion, all those factors (age, function, industry) matter. You need to think about each when you interact with any important contacts; start out as professional as possible, and take the relationship more personal as your contact allows you over the course of time.

I have certainly had bad communication interactions that made me question the judgment/thought-process of an entrepreneur – this has happened more than once. The entrepreneur/investor relationship has to be incredibly strong – there isn’t much leeway to damage that.

I often wonder about introductory emails / phone calls / meetings because I’m always making cold calls. How much do you think age (mine and theirs), function (investor, customer, etc.), and industry have in determining tone? Have you ever had an informal email leave such a bad taste that you pasted over an firm that was on the bubble of going through the next filter?