A gambler in the casino called Wall Street

Play it right

Author: Kamal Gupta

Publisher: Bloomsbury

Pages: 276

Price: Rs 799

Somerset Maugham once wrote that the majority of people live their lives like tramcars, shuttling from one end of the line to the other, and back. Each day they set out from their home for their workplace and then return in the evening. On their way back, they may take a detour for shopping or a drink. That is the sum total of the variety their systems can ingest.

But some people are wired differently. They seek out novelty and adventure. If they find their current job unexciting, they chuck it and venture into more challenging endeavours, undeterred by society’s disapproval, or that they may not have tried their hand at anything remotely similar in the past. They take enormous leaps of faith and live to tell the tale. Play It Right is the story of one such intrepid spirit. 

After completing his engineering degree from the Indian Institute of Technology, Delhi, Kamal Gupta headed to the United States where he completed his Masters in Computer Science in under a year. He then spent a few years in well-paying jobs with Honeywell and Oracle.

So far, so good. The only problem with his picture-perfect progression through life was that he found writing code irredeemably boring. His search for an antidote led to blackjack. His boss, another blackjack aficionado, told him the house could be beaten using the methods described by Ken Uston in his book Million Dollar Blackjack.

Much to his middle-class parents’ dismay, Mr Gupta then devoted himself completely to learning Uston’s techniques. He shut himself up in his apartment and spent months practising card counting. When he felt ready, he ventured into a casino.

His initial forays were disastrous. It is one thing to count cards in a silent apartment and another altogether to do so in the noisy, distracting environment of a casino. 

Mr Gupta then lowered the size of his bets so he could make his bankroll last longer. Playing for lower stakes had a calming effect on his nerves and he gradually became acclimatised to that environment. Just as he became convinced he could earn a living as a professional gambler, another impediment cropped up. Applying the maxim that it takes a thief to catch a thief, casinos employ card counters to spot those applying this black art (from the casinos’ standpoint). One such spotter caught Mr Gupta and he was evicted. The author felt his world had come crashing down around him. What was he to do if he would not be allowed to employ his talents, which he had developed with so much diligence and perseverance?

Soon enough, he came up with a workaround. Moving to a new casino, he also took on a new persona, pretending to be a globetrotting importer-exporter from India. Unlike the sober and calculating gambler he was, he put on an act of being loud, maniacal, and drunken. He was thus able to ply his trade for two years, multiplying his bankroll 30 times.

Mr Gupta’s life then took another dramatic turn. During a visit to New York, he met a few acquaintances at a club. When asked what he did for a living, he said he was a professional gambler. That elicited a number of excited queries. One member in the gathering handed him Michael Lewis’s Liar’s Poker (Mr Lewis’s account of a stint as a bond trader at Salomon Brothers) and said you ought to be a trader on Wall Street.

The idea, while ostensibly outrageous (Mr Gupta hadn’t studied finance), intrigued him. On a whim, he applied to several investment banks, highlighting his skills at blackjack.

During the interview at Lehman, the traders asked him tons of questions about this card game, all of which he answered easily. Then came the agni pariksha. He was given one chance to guess, within 18 seconds, which card had been removed from a well-shuffled deck. Using his card counting skills, he answered correctly, and thus landed a job many Ivy League graduates would have given a limb for.

In the second part of the book, Mr Gupta describes his journey through the murky world of finance, where selling lemons to customers was regarded as the highest art form. He soon grew disgusted and decided he would develop a trading system that would allow him to become a fund manager. After a lot of trial and error, he succeeded in doing so. He then deployed it to create an enviable record as a money manager over the next many years.  

Mr Gupta is a raconteur par excellence. His autobiographical account could give any good work of fiction a run for its money. Those keen on blackjack and bond trading may even pick up a handy trick or two and have a jolly good time devouring this utterly enjoyable read.