Raised on real estate

Danny and Hillary Hertzberg speak millennial because, well, they are millennials. And they’re using their knowledge of real estate, social media and technology to sell high-end residential real estate to young, wealthy adults who are migrating to South Florida from all over the world. 

“We have a lot of young buyers from South America and Central America,” explains Hillary, 28, adding that they also see buyers from California, New York and New Jersey. 

The wealthy millennials the Hertzbergs work with aren’t just heirs to fortunes. They’re also business owners, inventors, techies, bankers and hedge fund managers. “They love the lifestyle, the energy and the fact that South Florida is an international scene,” adds Danny, 33.

Minimal taxes are another draw to the region. “The fact that we don’t have a high state income tax is huge for the market,” Danny says. So huge, that many affluent buyers, young and old, become part-time Florida residents in an effort to avoid that extra bill. 

But millennials are a finicky bunch, the siblings say. They aren’t merely content with fantastic homes like baby boomers. Nor are they obsessed with location like buyers from Generation X. Millennials, the Hertzbergs say, want the whole package. And it’s not a package they search for in newspaper ads or commercials. They find it through technology and social media.

The Hertzbergs understand the millennial perspective thoroughly. “We really know how to get through to them in the most efficient way,” Danny says. “We speak the same language.” 

It helps that they are also fluent in real estate. Their mother is Jill Hertzberg, who, in the early 1990s, teamed up with fellow real estate broker Jill Eber to sell homes to the affluent in Miami Beach. Proclaiming themselves “The Jills,” Hertzberg and Eber amassed a reputation for selling mansions and penthouses to powerful executives and movie stars. Within the last two years alone, The Jills, along with their team of 20 Coldwell Banker brokers, have closed more than
$1 billion in sales. Both Danny and Hillary happen to be a part of that billion-dollar selling machine.

A graduate of Tulane University, Danny has a law degree and an MBA from the University of Miami. He previously worked for home-building giant Lennar before coming to work full time for The Jills in 2009. Among the first things he did was to bring The Jills into the 21st century. “They weren’t doing anything in social media,” he remembers. “I stared working on that aspect.”

Hillary arrived at the office a couple of years later. Armed with a psychology degree from Washington University in St. Louis, Hillary worked in sales at fashion house Theory and in digital marketing at MediaVest before becoming an associate for The Jills four years ago.

Together, the siblings formed their own team, Second Generation Selling, and set about tapping into the growing luxury millennial market. Last year, Second Generation Selling’s sales volume was $83.4 million.

Selling to the next generation means showcasing properties with detailed video presentations via Instagram, Facebook, WhatsApp and other social media applications, the Hertzbergs say.

And the homes? Forget about historic mansions built at the turn of the last century. Rich millennials want brand-new, sleek, modern LEED-certified homes with open floor plans, Hillary says. 

Unlike previous generations of homebuyers, millennials have no delusions about staying in a purchased home for 10 or 20 years, Danny adds. “They’re very comfortable with moving again,” he says. 

At the same time, millennials are as interested in the perks of the neighborhood as they are in what the home they buy has to offer. “We’re more focused on advertising lifestyle,” Danny says. 

And, after all the social media and texting, once the deal is ready to be closed, it isn’t a paper contract that’s presented. Instead, millennials prefer to consummate their real estate transactions using a digital platform called Dotloop, where fingerprints are used instead of signatures. “It’s better than ink,” Hillary says.

The Hertzbergs aren’t content just to sell homes to jet-setting millennials. Two years ago, they started the Second Generation Giving Foundation.

“After every transaction, we ask our clients what charity they want to give to,” says Danny. So far, they have donated over $15,000 to more than a dozen nonprofits, including the Humane Society of Greater Miami, Habitat for Humanity, the University of Miami Miller School of Medicine and Legal Services of Greater Miami. The donation is made in the client’s name, but it comes out of the Hertzbergs” commission. “It’s paying it forward,” Danny says. ?

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Drew Limsky

Drew Limsky



Drew Limsky joined Lifestyle Media Group in August 2020 as Editor-in-Chief of South Florida Business & Wealth. His first issue of SFBW, October 2020, heralded a reimagined structure, with new content categories and a slew of fresh visual themes. “As sort of a cross between Forbes and Robb Report, with a dash of GQ and Vogue,” Limsky says, “SFBW reflects South Florida’s increasingly sophisticated and dynamic business and cultural landscape.”

Limsky, an avid traveler, swimmer and film buff who holds a law degree and Ph.D. from New York University, likes to say, “I’m a doctor, but I can’t operate—except on your brand.” He wrote his dissertation on the nonfiction work of Joan Didion. Prior to that, Limsky received his B.A. in English, summa cum laude, from Emory University and earned his M.A. in literature at American University in connection with a Masters Scholar Award fellowship.

Limsky came to SFBW at the apex of a storied career in journalism and publishing that includes six previous lead editorial roles, including for some of the world’s best-known brands. He served as global editor-in-chief of Lexus magazine, founding editor-in-chief of custom lifestyle magazines for Cadillac and Holland America Line, and was the founding editor-in-chief of Modern Luxury Interiors South Florida. He also was the executive editor for B2B magazines for Acura and Honda Financial Services, and he served as travel editor for Conde Nast. Magazines under Limsky’s editorship have garnered more than 75 industry awards.

He has also written for many of the country’s top newspapers and magazines, including The New York Times, Washington Post, Los Angeles Times, Miami Herald, Boston Globe, USA Today, Worth, Robb Report, Afar, Time Out New York, National Geographic Traveler, Men’s Journal, Ritz-Carlton, Elite Traveler, Florida Design, Metropolis and Architectural Digest Mexico. His other clients have included Four Seasons, Acqualina Resort & Residences, Yahoo!, American Airlines, Wynn, Douglas Elliman and Corcoran. As an adjunct assistant professor, Limsky has taught journalism, film and creative writing at the City University of New York, Pace University, American University and other colleges.