Fundraising & customer acquisition are like dating; logic doesn't get you very far. The points PG makes might be valuable in convincing yourself that it's a field worth pursuing, but for convincing people to give you their attention and their cash, you need a different approach, which will usually involve some combination of: stories, charisma, status, social proof, exclusivity, to name just the first that come to mind.
The best material I've found about this kind of stuff is: Robert Cialdini's "Influence", and some of the less creepy pickup material, particularly to do with "inner game". Also, this new book by Australian business journo Valerie Khoo looks interesting:
Try the Richard Feynman approach - if you really want to understand what you're doing, try to teach it. Like, write a manual about what your business does, explain it to mom, etc.
+1 for teaching. I find that explaining deep technical problems to people who are smart, but otherwise clueless about technology, forces me to understand the issue myself at a much deeper level. My girlfriend is the best rubber ducky debugging buddy ever.
