What is the expected payout vs other ways to fundraise?
I'm not sure any profit below 500k$/year would be even worth considering, in light of the high risk of long-term emotional damage (and decrease in productivity, on top of not doing research while doing this stuff) to a high-value (F)AI researcher.
500k is a conservative figure assuming E.Y. is much more easily replaceable than I currently estimate him to be, because of my average success rate (confidence) in similar predictions.
If my prediction on this is actually accurate, then it would be more along the lines of one or two years of total delay (in creating an FAI), which is probably an order of magnitude or so in increased risk of catastrophic failure (a UFAI gets unleashed, for example) and in itself constitutes an unacceptable opportunity cost in lives not-saved. All this multiplied by whatever your probability that FAI teams will succeed and bring about a singularity, of course.
Past this point, it doesn't seem like my mental hardware is remotely safe enough to correctly evaluate the expected costs and payoffs.
long-term emotional damage
Are you worried he'd be hacked back? Or just discover he's not as smart as he thinks he is?
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.