What the Dog Saw

That was the kind of man Niederhoffer was. He had heard of Taleb’s growing reputation in the esoteric field of options trading and summoned him to Connecticut. Taleb was in awe.

“He didn’t talk much, so I observed him,” Taleb recalls. “I spent seven hours watching him trade. Everyone else in his office was in his twenties, and he was in his fifties, and he had the most energy of them all. Then, after the markets closed, he went out to hit a thousand backhands on the tennis court.” Taleb is Greek-Orthodox Lebanese and his first language was French, and in his pronunciation the name Niederhoffer comes out as the slightly more exotic Niederhoffer. “Here was a guy living in a mansion with thousands of books, and that was my dream as a child,” Taleb went on. “He was part chevalier, part scholar. My respect for him was intense.” There was just one problem, however, and it is the key to understanding the strange path that Nassim Taleb has chosen, and the position he now holds as Wall Street’s principal dissident. Despite his envy and admiration, he did not want to be Victor Niederhoffer—not then, not now, and not even for a moment in between. For when he looked around him, at the books and the tennis court and the folk art on the walls—when he contemplated the countless millions that Niederhoffer had made over the years—he could not escape the thought that it might all have been the result of sheer dumb luck.

Taleb knew how heretical that thought was. Wall Street was dedicated to the principle that when it came to playing the markets there was such a thing as expertise, that skill and insight mattered in investing just as skill and insight mattered in surgery and golf and flying fighter jets. Those who had the foresight to grasp the role that software would play in the modern world bought Microsoft in 1985 and made a fortune. Those who understood the psychology of investment bubbles sold their tech stocks at the end of 1999 and escaped the Nasdaq crash. Warren Buffett was known as the “sage of Omaha ” because it seemed incontrovertible that if you started with nothing and ended up with billions, then you had to be smarter than everyone else: Buffett was successful for a reason. Yet how could you know, Taleb wondered, whether that reason was responsible for someone’s success, or simply a rationalization invented after the fact? George Soros seemed to be successful for a reason, too. He used to say that he followed something called the theory of reflexivity. But then, later, Soros wrote that in most situations his theory “is so feeble that it can be safely ignored.” An old trading partner of Taleb’s, a man named Jean-Manuel Rozan, once spent an entire afternoon arguing about the stock market with Soros. Soros was vehemently bearish, and he had an elaborate theory to explain why, which turned out to be entirely wrong. The stock market boomed. Two years later, Rozan ran into Soros at a tennis tournament. “Do you remember our conversation?” Rozan asked. “I recall it very well,” Soros replied. “I changed my mind, and made an absolute fortune.” He changed his mind! The truest thing about Soros seemed to be what his son Robert had once said:

My father will sit down and give you theories to explain why he does this or that. But I remember seeing it as a kid and thinking, Jesus Christ, at least half of this is bullshit. I mean, you know the reason he changes his position on the market or whatever is because his back starts killing him. It has nothing to do with reason. He literally goes into a spasm, and it’s this early warning sign.

For Taleb, then, the question why someone was a success in the financial marketplace was vexing. Taleb could do the arithmetic in his head. Suppose that there were ten thousand investment managers out there, which is not an outlandish number, and that every year half of them, entirely by chance, made money and half of them, entirely by chance, lost money. And suppose that every year, the losers were tossed out and the game was replayed with those who remained. At the end of five years, there would be three hundred and thirteen people who had made money in every one of those years, and after ten years there would be nine people who had made money every single year in a row, all out of pure luck. Niederhoffer, like Buffett and Soros, was a brilliant man. He had a PhD in economics from the University of Chicago. He had pioneered the idea that through close mathematical analysis of patterns in the market an investor could identify profitable anomalies. But who was to say that he wasn’t one of those lucky nine? And who was to say that in the eleventh year Niederhoffer would be one of the unlucky ones, who suddenly lost it all, who suddenly, as they say on Wall Street, “blew up”?

Taleb remembered his childhood in Lebanon and watching his country turn, as he puts it, from “paradise to hell” in six months. His family once owned vast tracts of land in northern Lebanon. All of that was gone. He remembered his grandfather, the former deputy prime minister of Lebanon and the son of a deputy prime minister of Lebanon and a man of great personal dignity, living out his days in a dowdy apartment in Athens. That was the problem with a world in which there was so much uncertainty about why things ended up the way they did: you never knew whether one day your luck would turn and it would all be washed away.

So here is what Taleb took from Niederhoffer. He saw that Niederhoffer was a serious athlete, and he decided that he would be, too. He would bicycle to work and exercise in the gym. Niederhoffer was a staunch empiricist who turned to Taleb that day in Connecticut and said to him sternly, “Everything that can be tested must be tested,” and so when Taleb started his own hedge fund, a few years later, he called it Empirica. But that is where it stopped. Nassim Taleb decided that he could not pursue an investment strategy that had any chance of blowing up.

2.

Nassim Taleb is a tall, muscular man in his early forties, with a salt-and-pepper beard and a balding head. His eyebrows are heavy and his nose is long. His skin has the olive hue of the Levant. He is a man of moods, and when his world turns dark the eyebrows come together and the eyes narrow and it is as if he were giving off an electrical charge. It is said, by some of his friends, that he looks like Salman Rushdie, although at his office his staff have pinned to the bulletin board a photograph of a mullah they swear is Taleb’s long-lost twin, while Taleb himself maintains, wholly implausibly, that he resembles Sean Connery. He lives in a four-bedroom Tudor with twenty-six Russian Orthodox icons, nineteen Roman heads, and four thousand books, and he rises at dawn to spend an hour writing. He is the author of two books, the first a technical and highly regarded work on derivatives, and the second a treatise entitled Fooled by Randomness, which is to conventional Wall Street wisdom approximately what Martin Luther’s Ninety-five Theses were to the Catholic Church. Some afternoons, he drives into the city and attends a philosophy lecture at City University. During the school year, in the evenings, he teaches a graduate course in finance at New York University, after which he can often be found at the bar at Odeon Cafe in Tribeca, holding forth, say, on the finer points of stochastic volatility or his veneration of the Greek poet C. P. Cavafy.

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. Winn, Danny, and Pallop look as if they belong in high school. The room has an overstuffed bookshelf in one corner, and a television muted and tuned to CNBC. 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. There is almost nothing on the walls, except for a slightly battered poster for an exhibition of Greek artifacts, the snapshot of the mullah, and a small pen-and-ink drawing of the patron saint of Empirica Capital, the philosopher Karl Popper.

On a recent spring morning, the staff of Empirica were concerned with solving a thorny problem having to do with the square root of n, where n is a given number of random set of observations, and what relation n might have to a speculator’s confidence in his estimations. Taleb was up at a whiteboard by the door, his marker squeaking furiously as he scribbled possible solutions. Spitznagel and Pallop looked on intently. Spitznagel is blond and from the Midwest and does yoga: in contrast to Taleb, he exudes a certain laconic levelheadedness. In a bar, Taleb would pick a fight. Spitznagel would break it up. Pallop is of Thai extraction and is doing a PhD in financial mathematics at Princeton. He has longish black hair and a slightly quizzical air. “Pallop is very lazy,” Taleb will remark, to no one in particular, several times over the course of the day, although this is said with such affection that it suggests that laziness, in the Talebian nomenclature, is a synonym for genius. Pallop’s computer was untouched and he often turned his chair around so that he faced completely away from his desk. He was reading a book by the cognitive psychologists Amos Tversky and Daniel Kahneman, whose arguments, he said a bit disappointedly, were “not really quantifiable.” The three argued back and forth about the solution. It appeared that