Small Business Spotlight: The Roundtree

Lawyer-turned-hospitality entrepreneur Sylvia Wong delights in recreating memorable experiences from her travels.

The Roundtree
(Image credit: The Roundtree)

Women running their own companies? We love to see it. In our series Small Business Spotlight, we chat with independent fashion entrepreneurs about their journey to be-your-own-boss status. Here, tips for raising funds, developing a marketing strategy, navigating social media, and more—straight from women who have done it themselves.

Once upon a time, Sylvia Wong was frequently on the road, living out of hotels as a consultant for IBM, where she was stationed overseas in Shanghai and China, running emerging market operations for Africa, Latin America, and territories in Asia. "My professional background in corporate law has nothing to do with hospitality," says Wong. "Except for two things—I always loved traveling and often got to travel to places off the beaten path." 

Those experiences planted the seed for the next stage in Wong's career. After leaving IBM and joining a small residential real estate firm, Wong decided to dive right into her passion project turned business; to start a small hotel where she could offer the same delights and forever memories she experienced on her travels. After looking in California, New York, and even Sicily, the entrepreneur saw a listing for a small, historic property from the 1600s surrounded by farmlands, located on Main Street in Amagansett on New York's South Fork. Having only experienced being a guest of a hotel, but with a willingness to learn the ins and outs of running one, Wong purchased the unassuming property and, after undergoing extensive renovations amidst the beginning of a pandemic, opened The Roundtree on June 1, 2020, without a single reservation on the books. Now kicking off her third summer season with a roster of loyal return guests, Wong reflects on learning curves, what it's like running a small business in a male-dominated hospitality industry, and why authenticity remains at the forefront of her business model.

On Leading a Team:

A community of hotel owners and general managers in the area occasionally meet to talk about our experiences, and I may be the only female hotel owner. But being a woman is an advantage. It gives me great joy to take care of people and see our guests happy—it's a natural way of continuing to improve and fine-tune the business from better offerings to better customer service. And I think a nurturing attitude and attention to detail matter significantly.

Although I had previous experience leading teams in other fields, leading a team in the hospitality industry is new to me—we have a young employee population, especially in the seasonal market—and the demands and responsibilities are unique. I owe a lot to our general manager for putting together a great team. 

I always try to recreate my great travel experiences and memories for my guests. I don't come from a hospitality background, but my strengths lie in continually trying to represent the guest's perspective. If I were a guest, what would delight me? What would I want?

The Roundtree

Details are important to Wong, who offers complimentary bike rentals to discover the town or cruise to the beach.

(Image credit: The Roundtree)

On Overcoming Setbacks:

COVID-19 presented numerous challenges, especially for the hospitality industry. We faced difficulties procuring materials for the renovation and temporarily halted the construction. It was such a strange world that we were living in during the early part of 2020. Trying to start a business to do all of this, let's put it this way—it was a unique experience and will always be part of our history. Despite the uncertainty, we decided to open in June 2020 without guest bookings. But we implemented common-sense safety measures and took extra precautions to ensure everyone's well-being. Eventually, we started noticing an increase in guests who often stayed for extended periods. 

During COVID, safety and security were our number one importance. With it in the rearview mirror, we've transitioned that mindset with priority on a high-touch experience, from fresh flowers to ice cream happy hours and freshly baked cookies to a little mini bar stocked with complimentary drinks. I strive to create an intimate and welcoming environment where guests feel at home in a serene setting. If you're watching Netflix and want some popcorn, we will bring it to you! 

The Roundtree

Nightly s'mores around the fire pit are one of the at-home luxuries Wong dreamt up for guests.

(Image credit: The Roundtree)

On Community:

The support from the guests and the local community has played a significant role in overcoming the challenges posed by the pandemic. I wasn't expecting people to be so welcoming—but it continues today. 

What was surprising to me was many of our guests are very kind, and they're very vocal. They want to engage. They say, hey, I want to meet the owner, and their feedback is insightful.

When we first opened, the team said one of our guests wanted to speak to me, and I thought something bad happened— maybe the plumbing didn't work, but it turned out he was a local resident who just wanted to meet me and see us succeed. He introduced me to some of the neighbors in the community. I wasn't expecting people to react so positively. I would say speaking to people was the first indication that we were doing something positive. People have really enjoy the laidback atmosphere and the authenticity that Roundtree offers to everyone— guests and the community alike.

Sara Holzman
Style Director

Sara Holzman is the Style Director at Marie Claire, covering runway trends and tracking down the latest finds to buy and wear. When she’s not writing about fashion, she pens about the best places to jet-off to. Over her six years with Marie Claire, Sara has reported on the ever-evolving world of fashion— covering both established and emerging designers within the industry. Sara has held fashion positions at Lucky and SELF Magazine and was a regular contributor to Equinox’s Furthermore website, where she wrote across their style, wellness, and travel verticals. She holds a degree in Journalism from the University of Missouri, Columbia, and currently resides in Manhattan. Follow her along at @sarajonewyork.