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Dana Trotter
Tyler Whitman
When Dana Trotter was 22 years old, she joined a boutique real estate firm in Bridgehampton that was soon acquired by Sotheby’s International Realty. She remained there for 26 years, growing her career to becoming one of the top producers in the Hamptons.
But now, after resisting offers to jump to other brokerages over the course of more than two decades, Trotter has joined a new venture, The Agency Hamptons.
The Sagaponack resident will serve as managing partner alongside Tyler Whitman, who is the head of The Whitman Team at The Agency New York as well as a podcaster and a former cast member of Bravo’s “Million Dollar Listing New York.” With common approaches to business and disparate personalities that complement each other, they plan to build a new boutique-style real estate office in Bridgehampton.
Trotter moved to the East End in the late 1980s. Her mother was in real estate and her stepfather was a developer.
“I sort of grew up around real estate,” Trotter said on Friday. “I never thought I’d be in the business. I went to school for accounting and decided when I was graduating, I didn’t want to be a CPA. And I was riding horses actually professionally at that point. I was like 21, and my mother said, ‘Just get your license and help me with the rental season.’ And so I did, and I quickly just kind of fell in love with it and decided that horses were going to be my hobby, not my career.”
Meanwhile, Whitman grew up in the Florida Panhandle and lived in Alabama prior to relocating to New York. He joined the real estate startup Triplemint not long after it was founded in 2011, and joined The Agency last year when The Agency acquired Triplemint. Today, he splits his time between Sag Harbor and New York.
Whitman said he decided in November last year that he wanted to start up the Hamptons office after speaking with Mauricio Umansky, the founder and CEO of The Agency. Immediately, Whitman met with four or five top producers in the region. Though he knew Trotter because they both ride horses at Two Trees Farm in Bridgehampton, he said of the brokers he met with, he had the least personal relationship with Trotter at the time. Still, they found a connection.
“We sat down, and from the get-go I just had like this special feeling,” he recalled. “We just communicate so well. We’re on the same page about a lot of things. I think while our personalities are a little bit different and our brands are different, I think we really sync up when it comes to business and how we want to do things. And so I just felt this instant comfort with her.”
He credited Trotter with bringing local credibility to The Agency Hamptons.
“And then what I like to bring is leadership,” he added. “That’s my favorite thing about my job, is coaching people, training people and really empowering people to hit their goals.”
Whitman discusses both real estate and secrets to building a dream life on the podcast he co-hosts, “Glitter and Gay.”
Real estate agents’ brains go crazy and they tend to spiral, he said. “One of my gifts is helping people through their spirals and get a clearer picture of what they need to do as their next step and staying positive. I really feel like that’s what I was put on this planet to do.”
He said he’s seen real estate careers help many people get to their dream life. “And if I can help a lot of local people out here find that place and find a way to do this job in a way that makes them happy and live the life that they want to live, that’s like a dream career for me,” he said.
Whitman said he and Trotter want an office with a nice mixture of heavy hitters who do big business and rising talent — “people who are just getting their foot through the door and trying to build their careers.”
Trotter said that over the years every other agency out there had tried to get her to come over.
The Agency’s offer was different.
“This was not a lateral move for me,” she said. “This was not going to be a broker at another firm. This is a partnership in a new venture, and I’m super excited to work with Tyler — and we have a great synergy. I think we’re really good kind of yin and yang. We do things a little differently, and I think that’s great.”
At the onset of The Agency Hamptons, the team consists of just Whitman and Trotter, but growth is on the horizon.
“We’ll probably start making offers to a few key agents in July, and then we’ll officially open in August,” Whitman said.
He said the business plan, as he always does, is to go “low and slow,” getting systems in place and making sure everything is running smoothly. “And then have more of an organic growth from there instead of just coming out guns blazing.”
Trotter pointed out that she has never built up a team of her own and said that’s because managing people is not her forte. “I love being out in the field and I love selling and I love finding my buyers their dream property, and that’s my happy place, is just making those connections,” she said. “… That’s why we make a good team because Tyler is fantastic at leadership and I’m better in the field.”
Though they were not prepared to say just yet exactly where it will be, they plan to open an office in a prime location in Bridgehampton.
“A lot of Dana’s listings are coming with her, and there’s a lot of new listings going live,” Whitman said. “So Dana is coming over and transacting right away, but my plan is actually to be more of a sales manager than transactions.”
He said he wants to create an environment of healthy competition and not toxic competition, which, he added with a laugh, is a delicate line.
Trotter said since the news broke about her and The Agency Hamptons she’s had an onslaught of texts and emails from people who are intrigued.
“I actually took after my mother in that I’m extremely well liked in the brokerage community in the Hamptons,” she said. “I don’t think there are many people who have really anything bad to say about me, and to do that and be a top producer is pretty hard because most of the top producers have pissed a lot of people off. So I tried very hard to not burn any bridges throughout my career.”
