In the given game, the collective loses money just as the individual does. The collective wealth is the summation of the individuals' wealths, and both the collective and individual wealths drop over time. Write a simulation and try it if you don't believe me. I did, because I couldn't work out how the collective wealth could grow while the individual wealths drop, and the answer is that it does not.
The only way it looks like the collective makes a gain is if you try to say that x_i(t) = x_i(t-1)*1.05, but that's a simplification that doesn't hold in either the individual or the collective case.
But if you forget the part about the supposed misalignment between individual and collective, then the idea that the expected value of 1 iteration can be positive while the expected value of repeated iteration can be negative is very fascinating!