Going Infinite: The Rise and Fall of a New Tycoon

by Michael Lewis

When people asked Sam for his time, they assumed they’d posed a yes or no question, and the noises Sam made always sounded more like “yes” than like “no.” They didn’t know that inside Sam’s mind was a dial, with zero on one end and one hundred on the other. All he had done, when he said yes, was to assign some non-zero probability to the proposed use of his time. The dial would swing wildly as he calculated and recalculated the expected value of each commitment, right up until the moment he honored it or didn’t. “He’ll never tell you what he’s going to do,” explained Natalie. “You have to always be prepared it’s going to change every second.”

The tone of these private writings, in which he was in effect presenting himself to himself, were wildly different from the tone in which he presented himself to others. “I don’t feel pleasure,” he wrote one day, late in his Jane Street career. “I don’t feel happiness. Somehow my reward system never clicked. My highest highs, my proudest moments, come and pass and I feel nothing but the aching hole in my brain where happiness should be.” He knew he should feel grateful to Jane Street for finding value in him that no one else had, but he also knew that he didn’t. “To truly be thankful, you have to have felt it in your heart, in your stomach, in your head—the rush of pleasure, of kinship, of gratitude,” he wrote. “And I don’t feel those things. But I don’t feel anything, or at least anything good. I don’t feel pleasure, or love, or pride, or devotion. I feel the awkwardness of the moment enclosing on me. The pressure to react appropriately, to show that I love them back. And I don’t, because I can’

“That’s where I learned what the law is,” said Nishad. “The law is what happens, not what is written.”

That sort of argument just bugged the hell out of Sam. He hated the way inherently probabilistic situations would be interpreted, after the fact, as having been black-and-white, or good and bad, or right and wrong. So much of what made his approach to life different from most people’s was his willingness to assign probabilities and act on them, and his refusal to be swayed by any after-the-fact illusion that the world had been more knowable than it actually was.