Play It Right

A real-life underdog tale of one man turning the tables on the casinos and Wall Street without selling his soul to the devil

All around the world, the words “Wall Street” conjure up a powerful image. For some, it is the center of America’s capitalist system and the engine of its economic growth. For others, it is the home of rapacious bankers and reckless traders whose greed would lead to a global financial crisis. For an Indian-born blackjack player, Wall Street represented something else entirely — a chance for him to play in the largest casino in the world.

Kamal Gupta’s improbable journey, from a wide-eyed Indian immigrant to an ultimate insider in the rarefied world of investment banks and hedge funds, is a uniquely American story. Nowhere else would it have been possible for a scrawny computer scientist to enter the world of high finance solely on the basis of his gambling abilities. After spending seven years creating an investment methodology, Gupta went on an incredible run, generating an unprecedented 103 consecutive months of positive returns while managing money at large hedge funds. His success did not go unnoticed, and he found himself under constant pressure to take bigger risks to make even more money. He refused and always played it right, knowing that there was such a thing as “enough” money, something very few, if any, of his Wall Street peers understood.

Much like Maria Konnikova’s bestseller, The Biggest Bluff, Play It Right isn’t so much about money as it is about the human condition and beating the odds, whether at a casino, on Wall Street, or in life itself.

Kamal Gupta earned an undergraduate degree in electrical engineering from the Indian Institute of Technology in New Delhi — entering the elite institution after only completing eleventh grade — and received a master’s in computer science from the University of Wisconsin-Madison in just 11 months. Bored in the tech world, he turned himself into a professional blackjack player. An unexpected turn of events brought him to Wall Street, where for over two decades he beat the odds in every imaginable way. Gupta lives in the greater New York City area with his family.