My American dream unfolded in an unconventional manner. I started out as a bored computer scientist until a chance encounter with the game of blackjack set me on a completely different path — that of a professional gambler. In another twist of fate, my gambling skills landed me a job on Wall Street where I embarked upon a quarter-century odyssey into the unforgiving world of investment banks and hedge funds. And finally, having been a storyteller all my life, I decided to write a book about my experiences.
My journey to America began with a degree in electrical engineering from the Indian Institute of Technology in Delhi. With graduate school being the only available path to America, I applied to ten universities for a master’s in computer science. Several offered me admission and I chose the University of Wisconsin in Madison for its excellent reputation in the field. It helped that they had offered me financial aid that would cover all of my expenses.
In the eleven months that it took me to complete my master’s degree, I discovered I had little interest in computers. A stint at Honeywell in Minneapolis and Oracle in the Bay Area further reinforced my belief that my future did not lie in the computer industry.
On a ski trip to Lake Tahoe, a friend decided to try his luck at the blackjack tables. As I watched him play, I found myself becoming fascinated with the simplicity of the game; get as close to twenty-one as possible without going over. And when I discovered that counting cards could turn the odds in my favor, I was hooked. To the horror of my friends and family, I decided to become a professional blackjack player. I devoted the next two-and-a-half years of my life to the game, grew my bankroll by a factor of thirty-two, and got barred from several casinos in the process. At that point, I couldn’t imagine doing anything for the rest of my life other than traveling the world and playing blackjack.
This, however, was not to be. In another extraordinary turn of events, I found myself on Wall Street, the last palace I had imagined I’d be. I had mailed a resume to Lehman Brothers on a whim, not expecting anything to come of it. The company not only called me for an interview but also hired me on the spot (after I had correctly counted a deck of cards in sixteen seconds). I didn’t know the first thing about finance and yet, I decided to give Wall Street a try.
The move to New York City was rough. The atmosphere of the Lehman Brothers trading floor, alternately abusive and rapacious, made my life utterly miserable. The realization that I had switched sides from being a player to a dealer only made matters worse. In New York, I was employed by the house, an idea that I would have found abhorrent in Las Vegas. However, there was no other way for me to learn the game so I soldiered on. After two years though, I’d had enough. Much to the displeasure of my Lehman bosses, I walked away from Wall Street not knowing if I would return.
Three and a half months later, I did return, and with a newfound sense of purpose. Under the guise of working at an investment bank, I would devote all my efforts to creating an investment methodology for beating the U.S. mortgage market. It took another four and half years of constant thought and experimentation to create a system akin to counting cards in blackjack. I then spent the next two decades using that system to manage money for large hedge funds. During that time, I achieved an unprecedented streak of 103 consecutive months of positive returns which is quite possibly the finest track record earned by an individual in hedge fund history. In 2018, I played a key role in raising eight billion dollars for the largest hedge fund launch ever, ExodusPoint capital. In yet another unexpected twist, that experience set me on the path to writing a memoir.
Until then, my storytelling had been limited to a small group of friends and acquaintances. Seeing the effect that my life story had on complete strangers (potential investors in the new venture) convinced me that I needed to share it with the wider world. I took on the task of writing a memoir without having written so much as a one-page article before. It took four long and difficult years but that book, Play It Right, will soon be released in the entire English-speaking world.
I realize that my journey is unique, but that’s precisely what makes America special. My story, along with that of millions of other immigrants, could only happen here. More than any other country in the world, the U.S. rewards risk-taking. That ability, to take a chance and step into the unknown, is a vital ingredient for achieving the American dream. And so is the capacity to bounce back from the unavoidable reversals of fortune. I have faced numerous setbacks along the way — from getting thrown out of casinos to the abject misery of being a junior employee at an investment bank to rejection after rejection in the publishing industry — and yet, I persevered. After every misfortune, I took a step back, regrouped, and returned to the fight with a renewed sense of vigor. It wasn’t easy but, time and again, I have managed to overcome the obstacles and emerge triumphantly.
This article is living proof of that fact.
About the author
Kamal Gupta is the author of Play It Right, a memoir that chronicles his journey from India to America, from computers to gambling, culminating in a quarter-century on Wall Street. For more information, please visit kamalguptawrites.com
By Kamal Gupta
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