This is how New York real estate billionaire Larry Friedland got his start: He was studying to be a pharmacist in the late 1950s when he met a guy named Nathan Miller.

“You could name any building in New York, give him the address, without a computer, without a land book, without anything, he would tell you the size of the building, who dropped it in 1929, who jumped off the roof, he was just incredible,” Friedland said in the first interview of his 55-year career. “He really taught me the business.”

Becoming a druggist went out the window. He was hooked on real estate. In 1962, Friedland bought a string of storefronts anchored by a Bickford’s Coffee Shop in the Manhattan community of Harlem -- a deal brokered by Nathan Miller. Friedland said he needed three mortgages and a loan to pay the $400,000 price tag.

Fast-forward 50 years to 2012. When he purchased a three- story, pre-war colonial on tony Madison Avenue for $141.5 million, he paid cash.

In the intervening years, Friedland Properties, which Larry Friedland, 76, founded with his late brother Melvin in 1960, became the biggest retail landlord on Madison Avenue with more than 20 buildings. Its properties also include New York City parking garages and lots and two luxury apartment buildings in Manhattan with another planned. On a block in the Riverdale neighborhood of Bronx, New York, his strategy of letting commercial properties stay empty until he gets the tenant, and the rent, he wants has been criticized by residents. Friedland said nobody wants to fill the vacancies more than he does.

Friedland Properties can endure prolonged vacancies because its holdings are vast, many properties are debt-free and there are no shareholders to answer to, said Faith Hope Consolo, chairman of retail brokerage at Douglas Elliman Real Estate, who’s done deals with the company. The Friedlands keep abreast of fashion trends and hand-pick tenants who’ll keep Madison Avenue vibrant, she said. And that means “no dreamers, no delis,” Consolo said.

In all, Friedland Properties is valued at $3 billion, and Larry Friedland owns half, according to the Bloomberg Billionaires Index. Friedland disputes the calculation as too high. Unlike other New York real estate billionaires, he prefers not to trumpet his wealth.

“They’re the gatekeepers to the best retail strip in the city,” said Jeff Karp, director at New York-based RP Miller Commercial.

The Friedland properties on Madison Avenue, one block east and with fewer tourists than the more famous Fifth Avenue, are worth $1.6 billion before debt, according to the index. Annual rents on the strip between 57th and 72nd streets average $1,633 per square foot, according to CBRE Group Inc. Friedland’s current tenants include shoe store Roger Vivier, handbag-maker Kate Spade, Ralph Lauren, Loro Piana, Dolce & Gabbana and furriers Dennis Basso and J. Mendel.

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