Trade like Taleb

Taleb runs Empirica Capital out of an anonymous, concrete office park somewhere in the woods outside Greenwich, Connecticut. His offices consist, principally, of a trading floor about the size of a Manhattan studio apartment. Taleb sits in one corner, in front of a laptop, surrounded by the rest of his team — Mark Spitznagel, the chief trader, another trader named Danny Tosto, a programmer named Winn Martin, and a graduate student named Pallop Angsupun. Mark Spitznagel is perhaps thirty.

There are two ancient Greek heads, one next to Taleb's computer and the other, somewhat bafflingly, on the floor, next to the door, as if it were being set out for the trash.
pen-and-ink drawing of the patron saint of Empirica Capital, the philosopher Karl Popper.

The economist Eugene Fama once studied stock prices and pointed out that if they followed a normal distribution you'd expect a really big jump, what he specified as a movement five standard deviations from the mean, once every seven thousand years. In fact, jumps of that magnitude happen in the stock market every three or four years, because investors don't behave with any kind of statistical orderliness.

Taleb likes to quote David Hume: “No amount of observations of white swans can allow the inference that all swans are white, but the observation of a single black swan is sufficient to refute that conclusion.”

He doesn't bet on minor fluctuations in the market. Why bother? If everyone else is vastly underestimating the possibility of rare events, then an option on G.M. at, say, forty dollars is going to be undervalued. So Taleb buys out-of-the-money options by the truckload.

Buying a stock, unlike buying an option, is a gamble that the future will represent an improved version of the past. And who knows whether that will be true?
So all of Taleb's personal wealth, and the hundreds of millions that Empirica has in reserve, is in Treasury bills.

Taleb buys options because he is certain that, at root, he knows nothing, or, more precisely, that other people believe they know more than they do.

At Empirica, then, there are no Wall Street Journals to be found. There is very little active trading, because the options that the fund owns are selected by computer.
What Empirica has done is to invert the traditional psychology of investing. You and I, if we invest conventionally in the market, have a fairly large chance of making a small amount of money in a given day from dividends or interest or the general upward trend of the market. We have almost no chance of making a large amount of money in one day, and there is a very small, but real, possibility that if the market collapses we could blow up.

In the book that Pallop was reading by Kahneman and Tversky, for example, there is a description of a simple experiment, where a group of people were told to imagine that they had three hundred dollars. They were then given a choice between (a) receiving another hundred dollars or (b) tossing a coin, where if they won they got two hundred dollars and if they lost they got nothing. Most of us, it turns out, prefer (a) to (b). But then Kahneman and Tversky did a second experiment. They told people to imagine that they had five hundred dollars, and then asked them if they would rather (c) give up a hundred dollars or (d) toss a coin and pay two hundred dollars if they lost and nothing at all if they won. Most of us now prefer (d) to (c). What is interesting about those four choices is that, from a probabilistic standpoint, they are identical. They all yield an expected outcome of four hundred dollars. Nonetheless, we have strong preferences among them. Why? Because we're more willing to gamble when it comes to losses, but are risk averse when it comes to our gains. That's why we like small daily winnings in the stock market, even if that requires that we risk losing everything in a crash.

At Empirica, by contrast, every day brings a small but real possibility that they'll make a huge amount of money in a day; no chance that they'll blow up; and a very large possibility that they'll lose a small amount of money.

Empirica's positions, anyone at the firm can tell you precisely how much money Empirica has lost or made so far that day. At 11:30 A.M., for instance, they had recovered just twenty-eight percent of the money they had spent that day on options. By 12:30, they had recovered forty per cent, meaning that the day was not yet half over and Empirica was already in the red to the tune of several hundred thousand dollars. The day before that, it had made back eighty-five per cent of its money; the day before that, forty-eight per cent; the day before that, sixty-five per cent; and the day before that also sixty-five per cent; and, in fact-with a few notable exceptions, like the few days when the market reopened after September 11th — Empirica has done nothing but lose money since last April. “We cannot blow up, we can only bleed to death,” Taleb says, and bleeding to death, absorbing the pain of steady losses, is precisely what human beings are hardwired to avoid.

“Say you've got a guy who is long on Russian bonds,” Savery says. “He's making money every day. One day, lightning strikes and he loses five times what he made. Still, on three hundred and sixty-four out of three hundred and sixty-five days he was very happily making money. It's much harder to be the other guy, the guy losing money three hundred and sixty-four days out of three hundred and sixty-five, because you start questioning yourself. Am I ever going to make it back? Am I really right? What if it takes ten years? Will I even be sane ten years from now?” What the normal trader gets from his daily winnings is feedback, the pleasing illusion of progress. At Empirica, there is no feedback. “It's like you're playing the piano for ten years and you still can't play chopsticks,” Spitznagel say, “and the only thing you have to keep you going is the belief that one day you'll wake up and play like Rachmaninoff.”

“The key is not having the ideas but having the recipe to deal with your ideas,” Taleb says.