I was the 1 success out of 3, preceding the two losses. I went into it with an intention of being indifferent to the stakes, driven by interest in seeing the methods. I think you couldn't win against anyone with a meaningful outside-of-game motive to win (for money or for status), and you got overconfident after playing with me, leading you to accept the other >$10 challenges and lose.
So I would bet against you winning any random high-stakes (including people who go in eager to report that they won for internet cred, but not people who had put the money in escrow or the equivalent) game, and expect a non-decent success rate for this:
(I haven't played this one but would give myself a decent chance of winning, against a Gatekeeper who thinks they could keep a superhuman AI inside a box, if anyone offered me sufficiently huge stakes to make me play the game ever again.)
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.