I'm not a great salesman, but the people I've known that have really sold expensive things well.... sold very little on the product, and very much on the relationship. Most of while they 'sold' wasn't talking about the product at all, but rather lifestyle things (girls, market tips, etc.) or 'friendship.'
I've seen/heard a number of extremely expensive systems (my city is pretty posh), and its funny that every one that toured me of it said they 'knew someone and got a deal' or had some kind of inside key: "I got these 70,000 speakers for 20,000" and so forth...
The truth is, I don't think they sell much of the super-high-end stuff. I wonder how many speakers a year Wilson Audio sells... I bet it isn't much.