Yes, it does. That's the point: from the viewpoint of mathematical expectation, it's perfectly reasonable, but it doesn't fit the real-world situation particularly well.

In any case, it's not true that "almost all the time you'll come out even"; you'll never come out even - but the probability-weighted outcomes balance out. (Compare, e.g., a lottery; if you buy a $1 ticket on a million-to-one chance at a million dollars, you'll either wind up out a dollar, or up $999999.)