Odds of Success: From Casinos to Wall Street, Kamal Gupta Harnessed the Power of Calculated Risk to Win Big

UPDATED: January 30, 2024
PUBLISHED: June 10, 2022
Odds of Success: From Casinos to Wall Street, Kamal Gupta Harnessed the Power of Calculated Risk to Win Big

Let’s be real: Most gambling stories don’t have happy endings. Fortunately, Kamal Gupta’s story does. From counting cards at the blackjack table to trading on Wall Street, Gupta has enjoyed a fantastic journey, albeit a surprising one, that he never could have anticipated. 

“People who show up on Wall Street have dreamt all their lives of working on Wall Street, that’s what they’ve always wanted,” he explains to Brilliant Thoughts’ host and editor Tristan Ahumada in a recent interview. “Whereas in my case, I actually took a vow a few years before that I [would] never work on Wall Street.”

When Ahumada asks why he made this vow, Gupta explains that to him, Wall Street was a den of thieves, full of swindlers that resembled corrupt characters like Gordon Gekko. He believed the industry’s culture viewed greed as a good thing, an idea he just couldn’t get behind. 

Despite his initial reluctance, Gupta ended up taking a chance that changed his life trajectory. In his new book, Play It Right, he details how his love for numbers, taking calculated risks and fighting against unfairness led him to unprecedented success in the world of finance, which he refers to as “the largest casino in the world.” 

Don’t be afraid to apply your skillset somewhere new. 

Gupta assumed he would spend his whole life traveling the world and playing cards, but through a random series of events, he found himself interviewing for a job at Lehman Brothers. Instead of asking him about his trading experience (of which he had none), they asked him to figure out which card was missing from a deck—in just 18 seconds. To their astonishment, he did. 

When playing blackjack, Gupta used an advanced card counting technique that helped him make split-second decisions based on probability. He used the same skills to determine the deck’s missing card, and although it resulted in a job offer, he wasn’t totally sure how his talents would translate.

“On my first day at Lehman Brothers, I did not know the most basic thing about the finance of bonds,” he shares. “I didn’t know the most basic elements of bond math. All that had to be taught to me on day one, and of course, I made a fool of myself.”

In addition to performing poorly at Lehman Brothers, Gupta was also miserable. He hated the industry and struggled to find his groove. He eventually decided to leave, and it was during this hiatus that he began to formulate a new plan. 

Find an advantageous strategy and don’t deviate. 

When Gupta returned to Wall Street, he was determined to use the same strategy he did at the blackjack table: Find a way to take calculated risks and attract better odds.

“Taking calculated risks in financial markets and casinos is captured in just one facet of the game, which is that the odds have to be in your favor,” he explains. “If the odds are not in your favor, the longer you play the game, the greater the probability that you will lose.”

And as you might have guessed, Gupta isn’t the losing type. It took him seven years to figure out how to find a consistent advantage on Wall Street, but once he established a strategy that worked, he stuck to it. 

“While managing money for the largest hedge funds in the world, I never deviated from it for even a single moment, for like 20 years,” he says. “That’s a very long time to follow the exact same strategy, day after day, you know, week after week, month after month.”

Over time, his persistence paid off. In an incredible run of successes, Gupta had 103 consecutive months of positive returns while managing money at large hedge funds. Though his peers encouraged him to take bigger risks, he refused and always chose to play it right with his carefully formulated methodology. 

Win with a purpose. 

“Fighting against unfairness—like virtually everything in my life has been defined by that, from when I was in high school to when I was in college to battling the casinos,” he says. “I thought it was incredibly unfair that casinos sometimes threw out and sometimes even beat up card counters.” 

Gupta is no exception. He’s been kicked out of several casinos and has had to sweet-talk his way out of some bad situations. When he is discovered at one of his regular casinos, the people he’s developed a rapport with feel betrayed, like they’d been tricked by an old friend. Gupta doesn’t see it that way. He views casino blackjack as a war in which any tactic is fair game. 

“On numerous occasions, I had to take all sorts of evasive measures to not get picked up, from alternate identities to fake names to stealing my own chips to make it appear I was losing more or winning less,” he recounts. “In some ways, it wasn’t fun trying to figure out creative ways to keep playing, but then I decided to make a cat and mouse game out of it.”

Move forward with an indomitable spirit. 

Ahumada says that Gupta’s life belongs on the big screen, and he’s not the first person to think that. They joke about whether Hollywood or Bollywood will acquire the movie rights first, to which Gupta says probably Bollywood. Although he spent the first 23 years of his life in India, he is surprised by how well his book has been received there, mostly because it seems like a distinctly American tale. 

“The U.S. was this land of possibility for me, which is why I came here, and at least in my case, America’s reputation has turned out to be richly deserved,” he says. “I mean, where else can somebody come to study computer science, become a professional gambler, end up on Wall Street and then write a book about it?”

Gupta defines his two guiding principles as adhering to calculated risk and fighting unfairness, but there’s another subtle thread to his success story: the power of an indomitable spirit. Through trial and error, calculations and analysis, Gupta has ensured that no matter what he tries, the odds are bound to end up in his favor. 

Order Play It Right: The Remarkable Story of a Gambler Who Beat the Odds on Wall Street through Gupta’s website and Amazon, or pick it up at a major book retailer near you. 

Brilliant Thoughts with Tristan Ahumada is no longer releasing new episodes on the SUCCESS Podcast Network, but you can still listen to the full conversation below.

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Rae Fitzgerald

Rae Fitzgerald is a freelance writer, fly-fishing enthusiast and musician on the Austin, TX-label Keeled Scales. She received her BFA in Creative Writing from Truman State University.