I'm guessing Eliezer would lose most of his advantages against a demographic like that.
Yeah, they'd both lack background knowledge to RP the conversation and would also, I presume, be much less willing to lose the money than if they'd ventured the bet themselves. Higher-stakes games are hard enough already (I was 1 for 3 on those when I called a halt). And if it did work against that demographic with unsolicited requests (which would surprise me) then there would be, cough, certain ethical issues.
Update 2013-09-05.
I have since played two more AI box experiments after this one, winning both.
Update 2013-12-30:
I have lost two more AI box experiments, and won two more. Current Record is 3 Wins, 3 Losses.