Kamal Gupta - Play It Right: The Remarkable Story of a Gambler Who Beat the Odds on Wall Street

Eighteen seconds on the clock! someone shouted. Go!

I didnt know it then, but the entire course of my future hinged on those eighteen seconds.

A crowd of traders hovered around me. One removed a single card from a well-shuffled poker deck, and while keeping it hidden, handed me the remaining fifty-one cards. I had eighteen seconds to comb through the deck and identify the missing card. As Bud Fox had said in the movie Wall Street, life indeed came down to a few moments.

This missing card trial-by-fire was the culmination of a days worth of grilling about my gambling prowess during a lengthy job interview at Lehman Brothers. I had presented myself as a professional blackjack player and the investment banks bond traders were intent on putting that claim to the test.

All day long, the masters of finance had cross-examined me about every aspect of the game that they could think of.

Why are six decks worse for the player than two? Why do you split two eights against a dealer ten? How did you size your bets to account for the fluctuating probabilities? If the odds were in your favor, would you bet your entire bankroll on one hand? How many times were you kicked out of a casino? What was your annualized return on investment?

The Lehman traders fancied themselves great gamblers and they tried over and over to trip me up. Despite their best attempts to befuddle me, I sailed through the interviews. I knew more about blackjack than all my interrogators combined, and I made sure to let them know that. Interestingly, my swagger didnt turn anyone off. They almost seemed to approve of my brash attitude.

All that remained was this grand finale, a live demonstration of my card-counting abilities.

Under normal circumstances, it would have been simple for me to figure out the missing card in eighteen seconds. I had been successfully counting cards in Reno and Las Vegas for the past two years. Being under the spotlight on a Wall Street trading floor, however, was a very different kind of pressure.

In a casino, my senses were constantly under assault. I had to keep track of the count amidst the jangle of slot machines, the screams of the gamblers who had finally won one, as well as the lounge singer belting out the oldies. At the same time, cocktail waitresses were tapping me on the shoulder every few minutes for refills. Then there were the pit bosses. They watched every player like a hawk as it was their responsibility to guard the casinos bankroll against cheats and card counters. It had taken months of practice for me to be able to count cards amongst all the distractions in a casino. In contrast, this was my first time doing it on a Wall Street trading floor.

A crowd had gathered to watch me perform this parlor trick. This made me especially uncomfortable. Blackjack had been a solitary pursuit for me, not a spectator sport. I had toiled away in obscurity, trying to separate the casinos from some of their cash, and wasnt looking forward to the public shaming that would follow if I got this wrong.

For the Lehman bosses, that was precisely the point. They wanted me to count a deck in their presence to make sure that I wasnt all talk. The audience had been assembled to test my ability to perform under pressure, a skill they considered vital for a trader.

Even more than the trading floor atmosphere and the crowds scrutiny, I was concerned that I had just one shot at this exercise. No card counter is perfect and errors are inevitable during long hours of play. In a casino, one mistake wasnt fatal and every shuffle gave me a fresh start. Not so at Lehman. Here, a momentary lapse in concentration or a slight miscalculation would not only make me a laughingstock but also destroy my job prospects.

Despite my misgivings, I was keenly aware that any sign of apprehension on my part would be perceived as a show of weakness. Even though I had spent only a short time on the trading floor, it was apparent that testosterone ruled the day. I had no choice but to bite the bullet and submit to this public test. If I failed and fell flat on my face, then so be it.

I picked up the deck and gave a nod to the timekeeper to start the clock.

He did, and I flew through the cards in a controlled frenzy. Like I had done countless times before, I scanned them in groups of two or three. It would have been impossible to count fifty-one cards individually in such a short time. I had only a fraction of a second to eyeball each bunch and determine its count.

After what seemed like ages, I reached the end of the deck and shouted, Done!

The timekeeper stopped the clock with two seconds to go.

The trader with the mystery card crossed his arms and glared at me, Okay, hotshot, whats the card?

Its a nine, I replied calmly, even though my heart was racing.

With great flourish, he flipped the card over for all to see.

It was the nine of clubs!

I breathed a quiet sigh of relief while maintaining a nonchalant attitude. Of course its a nine, what else could it be? The crowd murmured its approval and dispersed. I slumped into a chair.

A tall, bespectacled man, wearing a gray suit and a strangely benevolent smile, put the cards back in their case and motioned me to follow him. This was Michael Gelband, and he guided me to a small office off the trading floor, closed the door, and handed me a thin envelope.

Open it, he said.

Inside was a one-page letter addressed to me. It began, We are pleased to offer you a position as a junior trader at Lehman Brothers... and ended with his signature.

I sat there in disbelief, clutching the letter, reading that line over and over again. Against the advice of my family and friends, I had given up on a career in computers and devoted two years of my life to blackjack. It had been a struggle, but I had beaten the casinos and grown my bankroll to thirty-two times its original size. And now, I had thrown a Hail Mary to the biggest casino of them all, Wall Street, and scored a job offer on the spot.

I had made the journey from San Francisco to New York for this interview on a whim, figuring that I was wasting my frequent-flyer ticket on a foolish pursuit. Lehman had insisted that I pay for my own flights because you dont seem serious about this business, an obvious fact that was hard for me to argue against. After an initial reluctance, I had decided to take a chance and used my airline miles for the trip. The gamble had paid off more handsomely than I could ever have imagined.

Now that I had an actual job offer, I wasnt quite sure what to do with it. Michael expected a yes right there and then. However, sitting in that office, I wasnt prepared to uproot myself from a city that I adored and relocate to one that terrified me.

I cleared my throat and said, I need to think about it. Ill let you know in two weeks.