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NEW YORK CITY-At first glance, some people in power seem ideally suited to their positions, as if their education and prior work experience were a perfect fit for their present job. The polar opposite has been true in the career of Annemarie DiCola, CEO of Trepp, who spoke about her career at a NYCREW Network breakfast Wednesday. Yet the fact that she has taken a somewhat unconventional path to the C-suite is exactly what led to her success, she said.

In 1990, “on a hot, sultry summer day,” after graduating NYU Law School and working at a firm for seven years on CRE deals—with her eyes firmly fixed on making partner—DiCola realized she was about to lose her job in the wake of a recession. She researched the areas of demand in the legal field and re-positioned herself as a bankruptcy attorney, which led to several offers. But she also reached out to an industry friend and former client, Rick Trepp, who offered to hire her as general counsel.

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