Power Broker: Dottie Herman, Self-Made Real Estate Titan

After visiting Southampton as a child, Dorothy “Dottie” Herman knew that one day she would call the quaint, waterside village “home.”

She did not know, then, just how many others she would help find the same “home” on Long Island’s East End—and far beyond.

Fast forward to 2020, and Herman is a national power player and perhaps the most noteworthy female figure in the real estate industry.

She is lauded for her career as a “self-made” titan of real estate. Herman is the epitome of the American Dream, which brings us to Long Island’s East End.

Herman is the CEO of Douglas Elliman Real Estate and in her current role, she oversees over 7,000 agents nationwide. The company had a whopping $27.8 billion in sales last year alone.

But her career, unlike many of society’s most successful, was not without obstacles. She learned resilience through the tragedy of loss at age 10—her mother was killed in a tragic car accident that also seriously injured her father—and it was the strength she learned then, out of necessity, that has made her such a force in real estate. Herman recalls her first major obstacle in her professional life, when she was a Regional Manager at Merrill Lynch. 

The company had chosen to sell the real estate division to Prudential. Prudential wanted to franchise, tasking Dottie with searching for a new buyer for Long Island—little did she know it would be herself. Only in her late 20s, Herman was inspired to find a way to use this sale to her advantage.

Instead of remaining on the sidelines, she began seeking individual and corporate investors to purchase the 36 Long Island offices and keep the region that she had managed intact. She recalls that many investors “laughed her out of the room.” 

Many more doubted her ability to purchase even one office, let alone 36. But, she recalls, not soon afterwards, she found herself in front of 2,000 employees across the New York-Metropolitan region saying: Prudential plans on selling the franchises, I intend to buy Long Island and Queens, and, “We are a family, let’s stick together. Together, we are strong.”

“Sometimes, it all seems surreal,” Herman recalls. “When I speak to real estate agents about my career, or to college students who seek to get into business, I can’t believe it.” The intangible that kept her going was love—for real estate, for the people she worked alongside, for the communities in which she was selling and the love for building something from scratch. “I never thought about being rich, or did it for the money. I did it because I loved it. My career is so amazing because I did what I loved, and I did not only do it for me.

“All of the success of Douglas Elliman is not only because of me, it is all the people who I have surrounded myself with,” she says. What makes Herman particularly interesting is the origins of her career in the Hamptons. Many who have familiarity with the real estate market on Long Island will remember that, before Elliman, there was a tight-knit community of real estate brokers on the East End. “New York Magazine wrote an article calling me ‘the broker from another planet,’ after I opened in the Hamptons. In those days, there was no MLS, and the major brokers boycotted me…but that did not stop me,” she recalls, referencing that many in the industry were longstanding brokerages, relying much on word-of-mouth business. 

Not being from the East End presented unique challenges to her when she first opened her office in East Hampton, and the second being in Sag Harbor, acquired from Earnest Shade. From there, she grew, opening in every town in the Hamptons. “But, as people started to learn about me, I earned the respect of the Hamptons brokers. I came from a middle class family, it was as much a dream of mine to have a house here as it was to open a business here,” she says. Herman now resides in the quaint Village of Southampton.

While she has been from the beaches of California, to the historic villages of New England—and everywhere in between—she says there is just no place like the East End. She expresses admiration for every one of the region’s quaint hamlets, saying that no one is more beautiful than the other, and that the integrity of the East End is a sum of all of its parts. Herman has spent more time in Southampton since the dawn of the global pandemic, but recalls a different “hustle-and-bustle” time, when the Hamptons were moreso a summertime weekend abode. “When I pass exit 70 on the LIE, every stress in my body starts to leave,” she says of the anticipation she feels as she nears Hamptons. “The open air, the beaches, the wineries, the boutiques, the small-town feel. Nearly every morning, I get my cup of coffee and drive two minutes to the ocean. It’s just like a different mode when you are on the East End. 

“There is nothing not to love,” she adds. 

“When I was just a girl, I visited a friend’s home in Shinnecock, and I swore I would have a house here someday. There truly is no better place in the world,” she remembers.

This same love is on display when she opened her business here. The love for the Hamptons is what guides her and her employees in her East End offices.

As those who live on the East End, the winter—and more specifically, the holidays—present an unrivaled beauty.

When asked what it was like on the East End during the holiday, Herman so adequately equated it to a “winter wonderland.”

Herman has a sign in her home, labeling it “My Tara,” a reference to the American movie classic Gone with the Wind.

“That sign really expresses how I feel about the Hamptons—how everyone feels about the Hamptons,” she says.

Whether you are a Hamptons Power Broker, or just a Hamptons resident, this statement rings true: We all have found our “Tara,” here on Long Island’s breathtaking East End.

Todd Shapiro is an award-winning publicist and Associate Publisher at Dan’s Papers.

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