If the experience was humbling, it certainly didn’t dampen Mr. Weiss’ ambitions. Already a Syracuse University grad, he enrolled in night classes at N.Y.U. to bone up on real estate and took courses on the art of negotiating at Fordham Law School. He sat in on tutorials by financial analysts and became a voracious reader of real estate primers. (He would complete a David Rockefeller Fellowship in 2005.)
The education paid off, and soon Mr. Weiss watched his stock rise. After a two-year stint at Studley, he took a job at development firm Olympia & York—“I hated it,” he says plainly—before accepting a broker position at the Edward S. Gordon Company, which would later be sold to the Insignia Financial Group. He returned to Studley in 1991, where he worked for 10 years until signing on with Newmark Knight Frank in 2002.
“I think I took a step back and realized they were full of shit and that perhaps they weren’t succeeding as much as they said they were,” said Mr. Weiss of the so-called peacocks he encountered in his first year at Studley in 1984. “At that moment, I remember seeing with complete clarity and saying, ‘Ignore everyone else. Focus on learning.’”
Mr. Weiss attributes his ambition and steely focus to his working-class roots. The son of a factory worker and a language interpreter, he suggested his childhood in Merrick, Long Island, may not have been so dissimilar from some of his colleagues.
“Very few of them, if any, come from any kind of silver-spoon background,” said Mr. Weiss, the father of three young boys who lives with his wife on the Upper East Side. “It’s almost as if you look at the subset of people who are successful as commercial brokers and see that failure wasn’t an option for them because they had no fallback position. I think I saw that early on.”