The Hamptons are now in full swing, and Sylvia Wong is certainly feeling it as the owner of the Roundtree hotel in Amagansett. For the NYC attorney, the road to hotelier was quite circuitous but a natural transition given her love of travel.
After studying law at NYU, Wong began her career at Paul, Weiss, Rifkind, Wharton & Garrison, a large law firm in the city, focusing on mergers and acquisitions, representing clients who acquired or sold businesses.

“As a young lawyer, it was an incredible learning experience to work alongside some of America’s best lawyers who are intelligent, creative and client-focused,” she said, noting that although it was a demanding job, it helped her build a strong foundation of skills in the legal and business realms, as well as personal development. “I think back about those years with fond memories.”

Wong then joined IBM and was based in Asia for about 10 years. In 2012, she returned to New York and was appointed chief compliance officer, leading the company’s worldwide ethics and compliance program.

Then, in 2015, another turning point: Wong was hired by Western Technology Investment, a private investment firm with a large real estate portfolio. As the company was looking to grow, hospitality became an organic extension of their holdings, and Wong’s too.

“Travel has always been one of my passions,” she said. “I was fortunate to have the opportunity to visit many incredible places around the world. Lots of wonderful memories are from visits to interesting places and stays at small hotels that offer understated luxury and excellent service.”

It wasn’t Wong’s initial game plan to open up shop in the Hamptons, specifically, but a fortuitous online property listing changed all that in early 2019. At that time, the now-hotel was a family-owned property called Gansett Green Manor, and one winter weekend, she took the Hampton Jitney to see it firsthand. “The jitney stopped directly across the street from the property. I still remember the crispness of the air vividly — it was a beautiful, chilly day. When I started to explore the property’s grounds, I immediately fell in love with it,” said Wong, who co-invested in the purchase of what would become the Roundtree with WTI. “Its expansive lawn and the surrounding farmlands offer such a peaceful and tranquil environment,” she added. “Yet it is located right on the main street, close to the wonderful local shops and restaurants, and within a short walk or bike ride from miles of beautiful white sand beaches.”

Wong was also drawn to the history of the property. “It was the homestead of one of the first four families who settled in Amagansett around the 1650s — we have a barn and several cottages that are hundreds of years old.”

After purchasing the property, the renovation process proved quite the feat. “There was so much work that needed to be done and having so many historic structures on the property made the process that much more tedious,” said Wong, noting the pandemic created an additional set of hurdles.

“About midway through the process, the state of New York suspended most construction projects aside from a very narrowly defined group of projects, and we were not able to determine whether we were able to proceed, so out of caution, we stopped without knowing when we’d be able to finish or even resume the work we were doing.” Ultimately, they were able to complete renovations just behind their original schedule. In 2022, the Roundtree also unveiled the Beach House, a compound of two dwellings just minutes from the main property that were once owned by playwright Neil Simon.

The site overhaul was “equal parts nerve-racking and exciting” with the pandemic exacerbating the challenges of debuting a hotel.

“In addition to making sure that our guest experience was everything we wanted it to be, we had to figure out how to create an environment that our guests felt safe in and how best to protect them. In the early days of the pandemic, there was no rule book to follow,” Wong said.

Thankfully, when the hotel opened its doors in June 2020, everything fell into place.
“We decided to take a simple approach — do what we would normally do if we were hosting friends and loved ones. When we opened, we had no reservations. We were so busy that we didn’t even have time to worry,” she said. “Very soon, when the first guests found us, we were met with a tremendous amount of appreciation and support from them.”

In their first year of business, about 80% of their guests came from NYC and the tri-state area. Now, that makes up half their guests, with the rest trickling in from the West Coast, Texas, Florida and “lately quite a few from Europe.

“For those who have a lifelong dream of opening an inn, Wong finds her secret sauce in remembering the little things.

“In my mind, passion, authenticity and attention to details are some critical success factors,” she said. “You must love what you do. It is a demanding job, but it won’t feel like it when you enjoy it. Do your research and utilize the resources that are available to you in terms of personal learnings, contacts and opportunities for mentorship.”

The entrepreneur also stresses the importance of learning from life experiences “to create a vision for what you want your guest experience to look like and what you want guests to take away from their time spent at your property.”

In the process of creating the Roundtree, Wong had countless people tell her “this is always how it’s done.” Still, relying on her own intuition to determine right from wrong was invaluable.

“It’s important to listen to advice but make your own decisions after that,” she said. “Ask questions, be inquisitive and trust your gut.”