When Will Silverman finally realized that his chosen path as an investment banker was not all that was promised, he simply made a decision to change careers—and never looked back.
With no experience to speak of, Mr. Silverman fled a high-paying job at JP Morgan Securities in 2002 and set his sights on the real estate industry, particularly on a job as an investment sales broker at Insignia/ESG.
Thanks to an acquaintance with Insignia’s then-CEO, Stephen Siegel, Mr. Silverman was able to land a coveted meeting at the well-regarded firm with building broker Woody Heller, an experience that the younger man simply describes as “the weirdest interview I’ve ever had in my life.”
“He picked up the phone and he made a phone call and the call lasted about 10 or 15 minutes, which seemed interminable at the time,” recalled Mr. Silverman of the Insignia meeting. “When he hung up the phone, he said, ‘O.K., what building was I talking about? Where is it? Who’s the retail tenant at the building?’ He was trying to ascertain if I knew the basics.”
The two men hit it off well, but Mr. Heller decided that Mr. Silverman was simply too green to be hired. Mr. Silverman did not necessarily agree.
“For the next five months I called him, I emailed him, I sent him writing samples, I had people call on my behalf—everything,” Mr. Silverman recalled last week during an interview in his Park Avenue office. “I just hammered away at him.”
And hammer away he did. He read textbooks and the biographies of real estate titans like William Rudin, all the while hounding anyone he knew with a broker’s license. In short, reader, he was a nag and a pest—and it paid off.
Perhaps exhausted from the deluge of phone calls, Mr. Heller finally relented. Six months after his first interview, Mr. Silverman was given a tryout at Insignia/ESG, where he was tasked with selling a pair of nursing homes during the day and given homework assignments during the evenings.
“Woody said, ‘If at the end of the week we think it’s working, you’re hired,’” recalled Mr. Silverman. “‘And if not,’ he said, ‘I’ll cut you a personal check for your time and we’ll figure out an equitable solution for that.’”
MR. SILVERMAN IS NOTHING if not persistent, a personality trait he gladly acknowledges has guided his rapid ascent in the real estate business.
Indeed, since transitioning from investment banking to Insignia/ESG, and then moving to Studley with Mr. Heller in 2003, the wunderkind has amassed sales transactions of $2.1 billion and more than 7 million square feet. In 2005, Mr. Silverman was named the youngest managing director in Studley’s history—at the ripe old age of 26 years old. He attributes his success to neuroses.
