When Friedland bought his first Madison Avenue property in 1965, the street was crowded with hardware stores, haberdasheries and drug stores, he said.

It wasn’t until the 1990s that Madison Avenue began attracting luxury retailers, said Gene Spiegelman, vice chairman and head of North American retail services at Cushman & Wakefield.

“You just need to have a good feeling about an area, you have to sort of look at it from a different angle and sort of look to the future,” Friedland said.

Early in his career, Friedland was vacationing in Puerto Rico and was struck by the number of Banco Popular branches. He said he walked into one and told an employee he thought he had a choice location for the bank in New York. The bank ended up signing a deal for one of Friedland’s Harlem storefronts, and Banco Popular began financing his deals.


Old School


The Friedland family is known among realtors as old school. A handshake means a deal and the rest is left to lawyers, Spiegelman said. 

Phone calls placed by realtors often go unanswered if the Friedlands aren’t interested in what’s on offer, said three realtors who asked not to be named for fear of damaging ties with the company. Friedland said it’s nothing personal. When he got started, he emulated his mentor Nathan Miller and began reviewing on a daily basis every sale of every building in the city, a routine he still maintains. That way,“if a broker calls me up with a left-field deal that makes no sense, I immediately know to say no,” he said.

While Friedland Properties is a family affair, Larry’s son William partnered with hedge fund billionaire Bill Ackman in a 12,850-square-foot retail property on Broadway in Manhattan, according to mortgage documents filed by Morgan Stanley, which underwrote a $65 million loan for the deal in 2013. The property houses a Chase Bank, luggage-maker Tumi and a pharmacy.

“It was his first deal going out on his own,” Ackman said. “He brought us what we thought was a very interesting deal.”

Ackman describes the investment as a “home run.”