I'm very regimented when it comes to email. When I receive a message, I'll ask myself "does it warrant a response?" If so, and it's not urgent, I'll wait a few hours to reply so I don't come across as a compulsive no-life loser. To ensure that I don't forget about the message, I'll star it or mark it as 'unread'. If the message asks me something that I don't want to answer right away, I'll reply with something like "I'll think about it and get back to you." Then I'll actually do it. I don't have much to be cocky about, so I feel like I've earned the right to designate myself A Damn Reliable Emailer.
For whatever reasons, a lot of the people I communicate with are not. I sometimes admire it and occasionally get steaming mad about it, but I usually just find it mildly impolite (my friend Amy once defined 'endearing' as "when somebody you like does something annoying"). However, it could present a huge problem in my quest to raise hundreds of thousands of dollars.
So why not just make some phone calls and avoid the problem altogether? Because I like to follow the Golden Rule, and my preferred method of being asked for money, by far, would be via email. It wouldn't matter if the person asking is a casual acquaintance or my own mother, or whether my eventual answer would be 'yes' or 'no' - an email would give me a chance to sort out my thoughts without being put on the spot, and it would let me do it at a time that's convenient for me. It's not a coincidence that I think telemarketers are the lowest form of life to ever exist.
My concern is that emailing people to gauge investment interest will inevitably lead to awkward phone calls and run-ins where I pretend to bring up the subject for the first time. If people start avoiding me because I send them emails about money, cold calling may be less detrimental to my relationships with them. Hopefully I'll still have friends when this is all said and done.