In early 2017, Holly Parker sat with a daunting list before her. On it were dozens of names she had to call with terrible news: a slump in the New York City real estate market had gutted their investments. She had long-standing relationships with these clients; some felt like family, and all were important.

While many business leaders could have panicked or shrunk from the task, Parker picked up the phone. Relying on years of experience turning setbacks into triumphs and leading people through life-changing choices, she dialed. “Hi, it’s Holly …” 

Parker’s personal investment in each of her clients is her “it” factor, the very thing that has made her a leading luxury real estate closer and one of Douglas Elliman’s top 10 performing agents over the last decade, with over $7 billion in sales. Now she would put these relationships to the test. 

Holly Parker made her first sale in fifth grade. “In elementary school, I sold my barrettes. Then I baked and sold homemade baguettes.” By 13, Parker was making $20 an hour running her own kids camp. “It was called Sunshine Daycare. It became so popular that my godfather, who was an attorney, made me shut it down because I didn’t have insurance.”

Parker’s parents were well educated and expected their daughter to succeed academically for a solid profession. “From early on, my father said, ‘Always be independent. Always support yourself.’”

Eager to excel, Parker attended Proctor Academy, a New Hampshire boarding school. “I was captain of the field hockey team, president of the dorm, and friends with the headmaster.” Parker’s confidence was bold, and some saw it as weakness. Upon making one misstep, she was made an example of.

Parker’s friends broke curfew one night, and although Parker didn’t, she was held equally accountable. Instead of getting the traditional penalty of being grounded, she was expelled. “Getting kicked out in the spring of my junior year was devastating, especially when all my parents talked about was SAT scores and college admissions,” she confides. 

Not one to give up easily, Parker argued her case to the head of the school and was able to finish her senior year, but on restricted terms. “It was a tough time, but it forced me to work harder than ever before.” 

Parker graduated on the dean’s list. Perhaps her greatest lesson learned from the experience was the  value of empathy, even putting herself in the shoes of the person who targeted her. “I think she suffered from a lack of confidence and was facing some personal battles that were dragging her under. If you can attune to others, channel and feel someone else’s pain like it’s your own, you will always prevail.”

Eager to depart her insular New England community, Parker attended the University of Puget Sound in Washington. There, she sold her meal plan and used the money to visit the quaint seaside inns in the Seattle area. “I loved seeing these magical places that people created. Even back then, real estate was my passion. I wanted to see other people’s ideas of heaven.”

By 25, Parker had moved to New York City and needed a job. With a real estate license in Boston, where she briefly lived after college, she was now entering a new market with no contacts.