Tyler Whitman: Leading The Agency’s Hamptons Market With Passion & Precision

Hamptons Real Estate

Tyler Whitman has quickly become a force in the Hamptons real estate market, parlaying his talents as a savvy negotiator and his flair for forging personal connections into deals totaling over $700 million in sales since 2018. As the managing partner of The Agency in the Hamptons, Whitman splits his time between New York City and Long Island’s East End. His ability to seamlessly navigate these contrasting worlds has been a key to his success in the competitive luxury real estate sphere.

Whitman arrived in New York over a decade ago with ambitions of making an impact. He has certainly achieved that, earning a reputation among clients for his innovative marketing strategies, deep market knowledge, and empathetic approach that transforms the home-buying experience into something more akin to a personal journey. Those skills have been displayed for viewers of Bravo’s “Million Dollar Listing New York,” where Whitman has been a cast member since 2019. He is also the co-host of the popular “Glitter and Gay” podcast. Away from the bright lights, Whitman finds solace in pursuits like equestrian sports around his second home in Bridgehampton. This unique ability to move fluidly between the urban hustle of Manhattan and the laid-back lifestyle of the Hamptons has become a defining attribute for the broker.

Hamptons Real Estate
Tyler Whitman. Courtesy of The Agency

You’ve had a remarkable journey from your roots in Florida and Alabama to becoming a top-producing real estate professional in New York City and the Hamptons. What initially drew you to pursue a career in real estate, and how has your background influenced your approach to the industry?

When I first left my small town in the South and came to New York City, I didn’t have a plan. I have dreamed of living a big life since I was very little, but I certainly did not have a clear vision of what that would look like. When I arrived in New York, I was waiting tables at Planet Hollywood in Times Square. Honestly, I think waiting tables in Times Square should maybe be a right of passage for all real estate agents. It was really hard, and I made very little money, as the average was $30 to $40 per shift. I got a second job working at TKTS, selling Broadway tickets to tourists to try and make ends meet.

It was a pretty dark time in my young adulthood. Financial life lessons were being hurtled at me. My cell phone was routinely shut off for late payments. I don’t know if I ever paid rent on time, and I got to a point where I just ignored my phone because it was almost always a bill collector trying to track me down. That said, I learned something really important: My gift is people.

I still say that to myself all the time. I love people so much, and I knew in my gut that this gift would serve me well in a career if I could just figure out a career that would serve it. Cut to a few months later when I had to move out of my first apartment and find a sublet because I couldn’t afford rent anymore. I ended up moving into a fifth-floor walk-up in the East Village with a roommate from Craigslist who had to walk through my bedroom to get to his. He was a real estate agent, and after a few months of witnessing his life, I thought… I can try that!

I thought I’d be pretty good — and I guess I was right. A lot of agents say they got into the business because of their love of architecture and design or things like that, which I certainly love as well. But I got into real estate 100 percent for the people. And 18 years later, I still can’t get enough.

You gained widespread recognition for your appearance on Bravo’s “Million Dollar Listing New York,” where viewers got an inside look at your professional journey and dynamic personality. How has being on the show influenced your approach to real estate, and what lessons did you learn from the experience that continue to shape your career today?

The experience of the show was monumental for me. Before the show, I had struggled with obesity my entire life. Body positivity was not part of my vocabulary, and my confidence in being in front of people was non-existent. However, my family raised me to believe in myself no matter what. And while obesity made it hard to do consistently, there was always a part of me deep down that believed I was capable of doing something really amazing.

In my early 30s, I lost over 200 lbs and slowly started to step into that hidden power. It started with social media videos that eventually led to a call from the “Million Dollar Listing” producers to be the new cast member. The experience came with so many life lessons. The biggest one is that it forced me to step up to the plate in a way I had never dared to do before. I couldn’t fail in my business with the cameras rolling and the world watching, so for the first time, I said yes to every opportunity and always came with my A-game and a belief that I was worthy of the opportunity in front of me. That confidence has never left.

I show up to everything with that inner dialogue of “How would you handle this situation if the entire world were watching? What can I do to make sure this is my absolute best work?” The other big lesson that I talk to our team about all the time is something one of the producers used to say to us: “All of the best stories have a messy middle.” Now, anytime I am in the middle of a challenge, instead of freaking out, I just say, “Oh, this is just the messy middle, and now I get to play hero, so the ending is incredible.”

As a Managing Partner of The Agency Hamptons, you’ve played a pivotal role in expanding the agency’s presence in this prestigious market. What unique opportunities and challenges have you encountered in navigating the Hamptons real estate landscape, and how do you leverage your expertise to deliver exceptional results for your clients?

Dana Trotter, my co-managing partner, and I have been crystal clear from the start that our biggest focus is to curate the right team of staff and agents. We truly believe that if we stay focused on bringing the right people on, no matter how long that takes, we will be a huge success. Every real estate broker will probably agree that recruiting is the biggest challenge and also the biggest opportunity for the company.

It is undeniably intimidating for an agent to pick up their entire book of business and move it to a new brokerage, so there has to be a great reason for them to do it. It took only a few meetings to find a gap in the industry out here, which is a lack of mentorship, training, and collaboration. A lot of firms offer high splits and big budgets, which seems appealing at first. But if there is no guidance or help in building the business, that money is useless. I go back to having a gift for people. I love helping our team navigate all the complexities of not only the transactions they are working on but also the process of growing and expanding their business while providing the best experience possible for everyone they work with. What has been amazing is that this has proven to be extremely valuable for very seasoned agents, and not just the agents that are newer to the industry.

Your experience as a Head of Sales at Triplemint and now as the leader of The Whitman Team at The Agency speaks volumes about your leadership and mentorship abilities. What principles or strategies do you prioritize in nurturing a successful and dynamic sales team?

Dana often says that our meetings feel a lot like having a life coach, which, to me, is a huge compliment. I want all of us to have a magical place to work. Somewhere everyone feels safe to share about what is working for them that will be helpful to their colleagues, and also share what challenges they are facing. I love helping people feel great and see their challenges from a different perspective. Success in sales is all about mindset, the ability to let go and be present for everyone we serve. One of my mottos is, “Teach your team everything they need to know so they can go do this without you, but treat them so well that they never want to.”

In addition to your thriving real estate career, you co-host the popular podcast “Glitter and Gay” with Glennda Baker, focusing on real estate and mindset. How do you balance your professional responsibilities with your passion for advocacy and community engagement, particularly in championing LGBTQ+ visibility and empowerment?

I get asked this question a lot, and to me, the answer is simple: they are all the same. I don’t separate the work, personal, and advocacy portions of my life. As an agent, if you don’t give back and contribute to the communities you sell, then you are stealing. While experience is important, people choose who they work with mostly based on how they feel about that person. Are your values aligned? Will you enjoy having to communicate with this person often?

I believe it is important that people know who I am as a person outside of just real estate. I am also well aware that who I am and what I believe in won’t be for everyone… and that is perfectly okay. The nice thing about putting so much of myself out there for the public to see is that if someone doesn’t want to work with me, I usually never hear from them. Which is pretty great because people who want to work with me reach out constantly.

Hamptons Real Estate
Tyler Whitman. Courtesy of The Agency

Your love for equestrianism and your dedication to training with your horse, Quinaro, demonstrate your commitment to excellence and discipline outside of the real estate world. How does your passion for horseback riding inform your approach to business and leadership?

That horse has absolutely changed my life. I really can’t over-exaggerate it. Two lessons, in particular, have impacted my career tremendously. The first is that I started riding in my mid-30s. I remember getting on the horse feeling very nervous and being in the ring with young kids on ponies that were galloping past me like seasoned professionals while I was learning the basics of walking and trotting and trying to keep my balance. It was humbling, to say the very least. So much so that I almost didn’t go back because I was so embarrassed. But I sucked it up and went back — and repeated the same embarrassing beginner journey over and over. And it led to one of the most fulfilling passions I’ve ever had outside of work.

It taught me that it is okay to not know how to do something because, with practice, guidance, and humility, you can learn anything. The second lesson came from when I started jumping. I had this terrible habit every time my horse would take me over a jump of immediately looking back to see if we knocked any of the poles down. Looking back while riding is a big no-no. Every trainer called me out for it, but I couldn’t stop doing it for some reason. Until I was taking a lesson with a new trainer about a year ago, and with the dryest, most direct tone, he said, “If you keep looking back at your mistakes like that, you’re going to mess up everything in front of you.”

It hit me in a place I didn’t know I needed to be hit. It used to be very easy for me to make a mistake and then have a total shame spiral over it. Now, my process is much more peaceful. If I make a mistake, I finish what I’m doing as best as I can, do a quick review to see what I can do better, and move right on.

With your extensive experience in negotiation and deal-making, what advice would you offer to aspiring real estate professionals looking to hone their negotiation skills and navigate complex transactions successfully?

Negotiating doesn’t mean lying. Honesty and valid information is the best way to win the best deal for whoever you are representing. Does that mean you need to give every piece of information you have? Absolutely not. But the facts are your best weapon in securing the best deal to be had.

As someone deeply connected to both New York City and the Hamptons, what do you believe sets these two markets apart, and how do you adapt your strategies to meet the distinct needs and preferences of clients in each location?

The markets could not be more different! Really the only thing they have in common is that a lot of the Hamptons homeowners are people who live in New York. Most buyers and sellers in New York City have a very strong specific motivation for transacting. It is usually related to daily life needs ranging from a growing family, a new job, a new school, or other factors that make the need for a move very important and having a deadline. In the Hamptons, there is rarely a deadline unless we are working with a 1031 exchange. Otherwise, most people are buying here for a want versus a need, and that work requires an entirely different skill set than the timely demands of New York City real estate.

Hamptons Real Estate
Tyler Whitman. Courtesy of The Agency

Looking ahead, what goals or aspirations do you have for The Whitman Team and The Agency’s continued growth and success in both the city and the Hamptons?

My goal is to nurture and cultivate the next generation of real estate superstars in both markets. I want to help them make all of their dreams come true. I have never been motivated by rankings in the slightest. They mean nothing to me — I don’t even report my numbers in New York City anymore. So, to me, it isn’t about where my numbers fall in comparison to other companies. I care about finding amazing people at various stages in their careers and helping catapult them to the level of success they desire. And to do that, I will never have or want hundreds of agents. I want a small handful that I can help become the absolute best. And wherever that lands us on the rankings is fine by me.

You’ve mentioned enjoying the lifestyles offered by both New York City and the Hamptons. Can you share some of your favorite spots or activities in each location that you enjoy outside of work?

Oh goodness — for NYC, the two things that keep me falling in love with the city endlessly are Broadway and Central Park. I am such a theatre lover, and if it were at all reasonable, I would go to a show every night. And Central Park is beautiful every day of the year and never gets old to me. Whether it’s crystal clear and sunny, covered in snow, or even a rainy walk with an umbrella — I love it so much. In The Hamptons, I live a much more social life than in the city, oddly enough. I love going to the beach with my friends, with Two Mile Hollow being my personal fav — going out on boats is amazing, and dinner at Leon in Shelter Island, The Beacon in Sag Harbor, or Crow’s Nest in Montauk are always among my top choices.

Lastly, what legacy do you hope to leave behind in the real estate industry, and what impact do you strive to make on your clients, colleagues, and the communities you serve?

Our industry, as much as I love it, has an underlying culture of being very secretive and leaves a feeling that you can’t trust anyone. I hope that what we have built is a shining example that being a good, ethical, honest person is the most enjoyable ride to the top. There is so much opportunity and need in both communities that I do my best to stay involved in as much as possible. It is up to all of us to make sure New York City and the Hamptons remain amazing places for generations to come. If I can do that, I will be very pleased with the life I have lived.

To learn more about Tyler Whitman and peruse his properties and history, click here.

Ty Wenzel

Co-Publisher & Contributor

Ty Wenzel, a recent breast cancer survivor, started her career as a fashion coordinator for Bloomingdale’s followed by fashion editor for Cosmopolitan Magazine. She was also a writer for countless publications, including having published a memoir (St. Martin's Press) and written features for The New York Times. She is an award-winning writer and designer who covers lifestyle, real estate, architecture and interiors for James Lane Post. She previously worked as a writer and marketing director for The Independent. She has won multiple PCLI and NYPA awards for journalism, social media and design, including best website design and best magazine for James Lane Post, which she co-founded in 2020. Wenzel is also a co-founder of the meditation app for kids, DreamyKid, and the Hamptons social media agency, TWM Hamptons Social Media.

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