Several people I've tried to introduce the site to have been turned off at the title: they interpreted "Less Wrong" to mean something akin to "We are a community of arrogant internet atheists who are Less Wrong than all of those stupid people".

I believe the potshots at religion in major articles also fed into this view for at least one person; he was interested in some of the articles, but used those potshots and selected comments to argue that the community was terrible. He now is interested in many of the ideas, but is semi-actively opposed to the community (e.g. he'll say derogatory things about it if it's brought up.)

In it's current form, I think the site is dangerous to share with anyone who is (a) religious or sensitive to poking fun at religion, or (b) cynical with regard to "atheist communities" which is what LessWrong is at risk of pattern matching as. I'd love to have a good resource for sharing rationality with those friends, although for some of them the well of "rationality" is poisoned by their negative associations with Less Wrong.

The site can be just a wee bit culty sometimes, by which I mean it pattern matches in a non trivial way to some other cult-like organizations, not that it's literally a cult.

I could list off some of them but then we'd get into the game where people pick each element in isolation and argue that it is not 100% correlated with actual cults.

It's not that less wrong ticks all the cult checkboxes or that every cult checkbox is conclusive but it does check more than most organization and enough to give it a vibe that makes people wary.