The gambling scheme which Kirk calls "Win by Losing" is based on Parrondo's Paradox, a real result in the branch of mathematics called "game theory". It is not actually a paradox in the literal sense (not like Russell's Library Paradox), but rather just a surprising and unexpected result. The point is that it is possible to combine two games with a low probability of winning into a single game in which one is more likely to win than lose. You can see how it might be possible to turn this into a "win by losing" scheme such as Kirk supposedly develops in this novel. However, it is not likely that there are any such applications of Parrondo's Paradox as there are some very strong assumptions one must make about the two games and the way they are linked together. (In other words, don't expect that you can do this with the games offered by casinos!)

But, the result has seen at least theoretical application within physics and mathematical biology. So, the description in the book (where Kirk encounters the idea while reading up on quantum physics) is plausible...and could possibly be the author's source and inspiration!