This post has been retracted because it is in error. Trying to shore it up just involved a variant of the St Petersburg Paradox and a small point on pricing contracts that is not enough to make a proper blog post.
I apologise.
Edit: Some people have asked that I keep the original up to illustrate the confusion I was under. I unfortunately don't have a copy, but I'll try and recreate the idea, and illustrate where I went wrong.
The original idea was that if I were to offer you a contract L that gained £1 with 50% probability or £2 with 50% probability, then if your utility function wasn't linear in money, you would generally value L at having a value other that £1.50. Then I could sell or buy large amounts of these contracts from you at your stated price, and use the law of large number to ensure that I valued each contract at £1.50, thus making a certain profit.
The first flaw consisted in the case where your utility is concave in cash ("risk averse"). In that case, I can't buy L from you unless you already have L. And each time I buy it from you, the mean quantity of cash you have goes down, but your utility goes up, since you do not like the uncertainty inherent in L. So I get richer, but you get more utility, and once you've sold all L's you have, I cannot make anything more out of you.
If your utility is convex in cash ("risk loving"), then I can sell you L forever, at more than £1.50. And your money will generally go down, as I drain it from you. However, though the median amount of cash you have goes down, your utility goes up, since you get a chance - however tiny - of huge amounts of cash, and the utility generated by this sum swamps the fact you are most likely ending up with nothing. If I could go on forever, then I can drain you entirely, as this is a biased random walk on a one-dimensional axis. But I would need infinite ressources to do this.
The major error was to reason like an investor, rather than a utility maximiser. Investors are very interested in putting prices on objects. And if you assign the wrong price to L while investing, someone will take advantage of you and arbitrage you. I might return to this in a subsequent post; but the issue is that even if your utility is concave or convex in money, you would put a price of £1.50 on L if L were an easily traded commodity with a lot of investors also pricing it at £1.50.
The nature of the pump is not clear to me. What is the repeated action referred to by the ambiguous "this"? If it involves buying L from me at prices lower than the expected value $1.5, it runs into the difficulty of where I'm getting this infinite supply of lotteries to sell you.
Upvoted, because that is indeed a problem. With a utility concave in cash, unless you happen to have an infinity of lottery tickets to hand, you cannot be money pumped in this way.
You can, however, be exploited because of your inability to correctly price dependent contracts.