Building the American Dream

Rup Singh sees real estate as key to the American Dream – for himself and others.

Rup Singh, a rising star in metro-area real estate, is a lot like George Bailey in the Christmas classic “It’s a Wonderful Life.”

Just as Bailey wanted to use the family’s Bailey Brothers Building and Loan business to give the residents of Bedford Falls the chance to be homeowners, Singh — founder of The Legacy Group, part of RE/MAX — would like to create a community of jobs and homes within the next five years, a place where people can pursue the American Dream. 

“I don’t chase money,” says the 28-year-old Singh, whose company grossed $30 million in 2019. “If you do something out of your heart and follow your passion, the money will come to you.”

A passage from India

Singh, who grew up in Westchester and Dutchess counties, has always been passionate about real estate and not just property but what you can do with it.

“I was always into handmade things,” he says. “I love architecture, the idea of building.”

As soon as he could, he bought a house for his family in Yonkers — father Paul, mother Sabi, brother Manu and maternal grandmother Swaran — complete with his mother’s dream kitchen. (Paternal grandmother Harbans and grandfather Ajit, who were also big influences on his life, are deceased.) The family hails from Punjab in India — a country with a long tradition of oldest sons caring for the parents and multiple generations living together. They are in many ways the classic immigrant story, with Paul, his American name, working a variety of jobs in gas stations and convenience stores before becoming head supervisor at Yonkers’ Domino Sugar plant. Today, Paul and Sabi own the revamped Paulie’s Gourmet Deli at 34 Tuckahoe Road in Tuckahoe. (Their real estate-minded son is very precise about addresses, down to the zip code. Mention this article, Singh adds, and get a free cup of coffee there.)

As a first-generation American, born at Lawrence Hospital in Bronxville, Singh is acutely aware of the idea that the first generation plants the tree whose fruits subsequent generations will enjoy. It’s why he named his company The Legacy Group. 

“I wanted something more for the team,” he says of his five employees. “I wanted them to have their own identity. I wanted to leave a legacy, to leave wealth.”

And because this is a classic immigrant story, it is really the tale of two countries. Singh has visited India and is engaged by its complex politics. He is fervent in his support of its protesting farmers — many of whom are minority Sikhs from the states of Punjab and Haryana — who’ve been camped outside New Delhi since November over the recent repeal of government protections, which they believe puts them at the mercy of potentially greedy investors.

But he was in many ways also a typical American kid, attending Sacred Heart Grade School in Yonkers and becoming an all-star Little League pitcher in Wappingers Falls, where the family moved to and where he attended Roy C. Ketcham High School. 

At Boston University, he abandoned a brief flirtation with medicine. Indians share the rest of Asia’s respect for academia and in particular the medical profession. Singh’s parents worried about real estate as a career choice. At the time, Singh says, it wasn’t the going concern it is today. And while they gave him their blessing, their fears were almost immediately realized. Singh remembers the $5,000 commission he earned on a New Rochelle home in 2014, not only because it was his first commission but because it was his only one that year. At the time, his parents’ deli wasn’t doing so well either. But Singh believes that “good things come with time.” By 2015, things were looking up.

“Now they tell everyone their son does real estate,” Singh says of his parents’ pride. “That to me is a blessing.”

View to the future

Singh’s success goes hand in hand with an ability to anticipate trends in the commercial and residential real estate markets in the metro area. With interest rates low, Westchester and Fairfield counties remain both buyers’ and sellers’ markets amid a continuing Covid-19 exodus from New York City.

“A one-bedroom unit on the Upper West Side can cost you $1 million,” Singh says. “People figure they can get much more for their money in the suburbs,” where, he adds, houses can begin around $500,000.

And while the commercial market has taken a hit, Singh sees opportunity in the transition of office buildings to mixed-use spaces with residences, a little retail and other businesses and with whole buildings becoming warehouses — what he calls the Amazoning and eBaying of America. But though it may take a couple of years, he is optimistic about New York City and the return of residents who will find themselves in a position of greater purchasing and negotiating power. Even in its darkest days, New York continues to reimagine itself, recently opening Penn Station’s triumphant new Moynihan Train Hall. (See story on Page 10). Central Park was built amid the panic of 1857; the Empire State Building and Rockefeller Center, in the early 1930s, amid the Great Depression.)

Buildings like the Empire State and its rival, the Chrysler Building — that bauble of Jazz Age dreams, which was topped just as the market crashed in October 1929 — were mainly unoccupied for years. So the idea of empty office space in Manhattan isn’t new.

Singh says structures like these and the new Vessel — a dazzling honeycomb of staircases between the restaurants and shops of Hudson Yards — will never go out of style.

“These landmarks are always going to live,” he adds.

While he keeps one eye on the Big Apple skyline, the other looks lovingly on the suburbs where he sees great community support and where he is determined to do his part. He not only donates food to homeless shelters but has seen to it that youngsters there receive haircuts at Royalty Chop Shop in White Plains.

“I want to make a difference in the world,” he says. “That is my greatest passion.”

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