He quite explicitly says that ugliness (quite apart from simplicity) actually has some advantages, like earning the trust of a certain class of users.

It's fine to disagree, but to suggest that he's "confused" when he's stated that so clearly is kind of condescending.

I think he may be right, and I think the "ugly == trustworthy" idea is also lent credence by the hideous ads in small newspapers, in "Coupon Clipper" type mass-mailings, ugly signs for small local businesses, etc.

He has made up this elaborate theory that ugly sites sell because they're ugly, when Occam's razor says they sell despite being ugly. Thinking that muddy can accurately be called confusion.

"Elaborate?" His notion is, if anything, radical in its simplicity.

Websites, advertisements, et al. do not exist in a vacuum. If websites "sell despite being ugly" then the whole design business is a scam, and at the end of the day you've got a much more complex situation to explain. What does Occam's razor tell you about that?

The point he's making is that design sends a message. Certain types of "bad" design included. And that certain types of "bad" design send a message that may actually appeal to some users. Is that really so elaborate, so confused?

I didn't mean elaborate in the sense of how many words it takes to express.

Right on. Another factor is the content of the site. This is something I only recently realized.

I always used craigslist's success in spite of ugliness as my reason for not thinking hard about style. But people expect classifieds to be ugly. People don't expect the place where they put their photos to be ugly. I've contracted a designer.

Here's a meatspace comparison. You talk to two salespeople. One is plain looking in plain clothes that could be bought at Target (or some equivalent box store). The other has a similar message, but is stunningly beautiful and wearing amazing designer clothes. Do you trust one more than the other (assuming all other factors are equal)? How many people would walk into a car dealership and approach the salesperson who was most attractive?

I think some "pretty" design smells like salesmanship to the savvy consumer, and this is reinforced by the fact that many of the most valuable sites (Craigslist, Amazon, Google, Ebay, Gmail, Del.icio.us, Reddit) aren't pretty to look at.

This isn't about usability and it isn't about simplicity. It's about the spectrum of ugly ranging to beauty and whether people have a bias against pretty/slick design (I think that a lot of people do).

Yes, I trust the beautiful one more, and I also consider her more intelligent. Not consciously of course, but it's definitely there. It is a somewhat disturbing fact that most people do this, although many won't admit it. See Robert Cialdini's book "Influence - the Psychology of Persuasion".

I don't know whether or if this translates to design though.

I agree. There is probably an element of survivorship bias; plenty of poorly designed sites don't last long enough to become part of a statistic.