How Sylvia Wong Went From Lawyer And Investment Exec To Award-Winning Hotelier In The Midst Of A Global Pandemic

“This is completely different from what I’ve done for most of my life,” Sylvia Wong says, looking out on a sprawling, green field just 100 miles outside of Manhattan, in beachy Amagansett. Though it appears second nature to her—as she greets guests, readies every room, lays out a daily offering of afternoon cookies, and maps out landscaping additions—owning and operating a hotel was never exactly in the cards for Wong.

Trained as a lawyer at New York University, she began her career at a law firm in the city working on mergers and acquisitions before joining IBM. During her 15 years at the technology behemoth, Wong was posted in Singapore and Shanghai for extended periods of time and eventually oversaw all emerging markets, a job that required near-constant travel between Latin America, Africa, Asia, and Eastern Europe. “I spent most of my life traveling, and I dealt with all kinds of issues, from big contracts with customers to litigation to even having employees get arrested, so I really saw it all,” she recalls.

When she left IBM and returned to New York a few years ago, Wong started working as partner in a private investment firm that deals with a lot of real estate, and she was reminded of an aspiration that had arisen long ago as a result of her frequent travels. “I’ve always, always, always loved traveling, even when I was a poor law student; it was just my thing, and I always enjoyed going to new places,” she says. “So, I always thought that maybe someday I would open my own hotel, but like with most of those dreams, I figured I would never actually do it.”

But in 2019, she decided to make the dream a reality. “I wasn’t really sure of the location, but I knew I wanted something close enough to New York so that I could actually run the business,” she explains. “So, I was looking for a place and didn’t and didn’t really have any particular criteria beyond that.” Then, she saw a listing in the paper one day for an inn in Amagansett with a rich history and lots of lush land and decided to take the Hamptons Jitney out there the following Saturday to see if for herself.

“I didn’t know what to expect, but once I saw the property and the farmland, I realized how beautiful the place was,” Wong remembers. The place had been run as an inn for several decades and had all of the eccentricities of a mom-and-pop operation, but it exuded charm and history throughout. “When I first walked in, I saw a little sign on the neighbor’s house saying that it’s the oldest house in Amagansett, and it turned out that this was the homestead of one of the first four families that settled in Amagansett in the 1600s,” she notes of the inn, where one two-bedroom cottage is over 250-years old. “So, I thought it was pretty cool, and then when I saw the farmland, I just knew that this was it.”


Wong bought the inn and kept the former owners on for six months to teach her the ropes of running a hotel while the property underwent gut renovations to ensure it would be up and running in early 2020, ahead of the summer season. Then, the Covid-19 pandemic hit.

With hotels deemed essential businesses in New York, Wong knew it could still open and was determined to finish renovations on schedule, all while creating a plan to keep guests and her staff safe. “We opened on June 1, 2020, but didn’t have a single reservation,” she says. “No one was really traveling at the time, and we didn’t know exactly when we would actually open because things kept getting pushed back.” But as guests began to trickle in over the first weekend, it became clear that The Roundtree was everything Wong wanted it to be.

“I remember the first week, I was going to get my coffee in the morning when one of my staff members told me that a guest wanted to meet me,” she recalls. “And I of course assumed they needed to complain about something, like there was no hot water or worse.” But sure enough, when Wong went to go meet the guest, who was staying in a three-bedroom cottage with his family while their nearby home was under construction, he wanted to welcome her to the area and express how impressed he was with the hotel and everything she’d done. “Just to see that warmth and that wonderful side of humanity was so amazing,” she says. “And I loved that staying at The Roundtree wasn’t just a transaction because my vision for it was always to make it feel more like a home than a hotel.”

With five cottages, some with two and three bedrooms, and a total of 10 additional rooms and suites, the hotel can accommodate up to 40 guests and is a prime destination for groups and families—including pets. And despite its prime location on Amagansett’s Main Street, The Roundtree is surprisingly quiet. “I wanted guests to feel like this was their own backyard,” she explains as she looks onto the massive lawn. “Even when we’re completely booked, I wanted it to feel like this is all just theirs.”

And indeed, that’s exactly how guests seem to feel while visiting the property. You’ll find kids and dogs running around in the grass while their parents take Zoom calls from a chaise lounge and neighboring couples take advantage of the hotel’s complimentary bikes or share a bottle of wine by the fire.

Although The Roundtree has no official kitchen, it serves a continental breakfast to guests every morning, which can be ordered to their rooms or in the garden, and has partnered with local restaurants to pick up and plate takeout orders. It also stocks every room and cottage with complementary drinks and snacks, in addition to the coffee and tea available around the clock in the main lodge, afternoon chocolate-chip cookies, and evening s’mores. “I’m naturally very nurturing and like to take care of people, so I always try to make sure every guest has everything they need,” Wong says. But as many of her thoughtful touches suggest, she and her staff tend to fulfill their guests’ needs before their guests are even aware of their needs.

Not even two years after opening, The Roundtree has seen continued success and high occupancy rates and has received impressive accolades, including the Travel + Leisure World’s Best Award. But Wong says the biggest indication of all that the hotel has accomplished is the sense of loyalty its guests feel to the property. “So many people who come here once end up coming back, whether it’s every year or every weekend,” she says. “And in a lot of ways, our guests become like family, and the hotel becomes their second home, which is exactly what I wanted when I opened The Roundtree.”


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