239: The Importance of Being Bold in Business, With Real Estate Mogul Dottie Herman

You don’t become the richest self-made woman in American real estate by playing it safe. Dottie Herman has proved time and time again that bold moves pay off. In the 1980s, in a maneuver that solidified her path to the top in real estate, Herman flew to California and convinced Merrill Lynch to hire her to help the company expand into the real estate market. In 1990, when Prudential decided to sell its regional holdings, Herman then persuaded the company to lend her $9 million to purchase its own Long Island real estate offices. And in 2003, Herman expanded her empire into New York City with the nearly $72 million purchase of the most prominent Manhattan real estate company, Douglas Elliman (again convincing Prudential to finance the deal). “If you don't ask, you don't know,” Herman says. “And the worst that can ever happen is someone says no.” Key Takeaways How Dottie Herman got into real estate Her bold move that convinced Prudential to lend her money to purchase one of its own companies How she weathered a recession while running her business The story behind acquiring Douglas Elliman, a prestigious real estate company in Manhattan Why she wanted to expand her real estate empire into New York City Her thoughts on branding How she maintains a good working relationship with her employees What she hopes to do next