This week I had lunch with two Portland based angel investment funds.

If you have ever sat down with someone who makes investments in high risk seed companies for a living, you know how the first 30 minutes goes. First, they eye you warily and wait for “the pitch.” Next, when the pitch doesn’t come, they start to relax and steer the conversation toward purely innocuous matters; family, weather, sports, anything that doesn’t make it a clear path back to “so I have this idea I want you to hear.”

This particular lunch was set up by a third party who knew us all and just thought we might have mutual business interests. Since the angels in this case knew nothing about MasterPlans or our business, they probably assumed I was there with some kind of pitch when in fact I wasn’t, but it gave me some real good perspective into what investors might think anytime they are introduced to someone, “this person wants money from me.

In this business we often paint the picture of the investor as the guy to be got, the fish to be landed, the evasive emotionless “vulture capitalist.”

I came away from this lunch feeling a little sad for these guys with the gold. What it must be like to fear everyone you meet might just want to actually sneak pitch you something, always wondering what relationships are genuine? After 45 minutes of figuring out I wasn’t after anything from them, the conversation became candid about business. What kind of plans are you seeing? How many clients do you get? Are any of them anything I would be interested in? Since I never brought it up, it made it much more comfortable for the investors to set the tone and pace of the business conversation and I walked away with a single piece of advice I can give to our clients. Meet 5 potential investors and never pitch a thing to 3 of them. You’ll learn quickly once they know you are genuinely interested in them, they may become genuinely interested in you.