Comment by wrvn

That approach would still leave you weak to always picking 1 or 100. Without proof, I believe the optimal guessing strategy would perform equal (on average) for every number, to not give the opponent any standout choice (common for optimal strategies, but not always the case). If my math serves me right, that would be an average of log2(100) = 6.64 guesses for any number, which would make you lose 0.64$ on average.