I think it boils down to "not seeming weird." For SIAI, I think it's it's pretty simple: we need to sound plausible so that we can get more donations! For LessWrong it's slightly more complicated, but it comes down to this: if people aren't deterred by the weirdness of the local beliefs and tropes, maybe they'll stick around and learn something useful.
I've been having a bit of a back-and-forth with a friend about what appears to be a charisma problem with the SIAI, and was hoping you lovely folks had thoughts on the matter. My friend was going through the Eliezer Q&A videos, specifically Question #7, "What's your advice for Less Wrong readers who want to help save the human race?" He typed up a transcript for Eliezer's answer, and went on to say:
He went on to mention that he really likes Eliezer's writings, and that his issue rests with the verbal skills of SIAI's leadership, not with the quality of their works.
I replied:
I also suggested a couple possible (though rather outlandish) ways to make an organization wildly popular. Specifically, to hire a marketing researcher like Frank Luntz to figure out what talking points would win the hearts and minds of the greatest number of people, or alternately to get major brand loyalties by having a cult figure like Steve Jobs representing the SIAI. Of course, I am stating this much more eloquently than I did in the email.
His reply deserves full posting here (with his permission, of course):
The question is now open. Does SIAI have a PR problem? If so, is it due to finances, lack of talent, or something else? Is there an Eternal September issue with watering down the brand (would you support the SIAI if they started investing heavily in advertising campaigns, or would you get a bit suspicious?)? Should they pay Frank Luntz to figure out what transhumanism terms work best with your average family? My friend and I are dying to know.