... until Oroborous broke it.
I only ever lost one bet where the bet was a personal bet about a real-world prediction (as opposed to games of chance or general investment and speculation). Not that I bet very often. Nor do I bet much money - as shown in the picture above, a dollar is my favorite amount. (That plaque was created by a guy who watched me win a long streak of bets, then bet against me and also lost.)
The vast majority of the bets I've taken were against gloom and doom scenarios where given objective market prices and volatility the odds were at least three-to-one in my favor. In these case, either a whole lot of people are quite wrong and are going to lose a lot of money, or the person I've taken the bet against was a little bit over passionate about how bad things are going to be. In many of these cases, if the bet was large enough, I could literally cover my position with puts or calls and guarantee myself profit whether or not I won the bet! The bets were never large enough to do that, but it's still a good bet.
So along comes Oroborous, once a co-blogger at The Daily Duck, and just before the collapse of the housing bubble and resulting financial crisis he states that the stock market is going to drop precipitously. I look at the S&P500 index and its volatility and calculate 95% confidence bands for various time frames (that effectively gives me 20-to-1 odds). Oroborous picks a time frame and its associated index level, takes the bet, and the day before time is up the S&P500 drops below that level.
So I finally lost one. This is old news in that I lost this bet over 3 years ago. However, Oroborous seems to have dropped off the face of the earth so I've been unable to pay him. Recently, Hey Skipper (a one-time co-blogger of Oroborous) gave me Oroborous' email address and I sent Oroborous an email asking how I should pay but got no response. Perhaps he'll show up again one day.
At 3-to-1 or even 20-to-1 odds it was inevitable that I'd eventually lose. I'll have to admit that I'm surprised that I lost because of something Oroborous foresaw. Usually such losses are caused by random, or nearly random events and/or fluctuations. Like a war starting. Or a particularly bad set of politicians being elected. Or an Oil embargo. Or something like that.
That it was foreseeable and only Oroborous and a relatively small number of others foresaw it is remarkable. He's either amazingly lucky or incredibly prescient. Or both.