Starting small but thinking big was always the plan for Stephanie Chai, who started The Luxe Nomad out of her apartment and has grown it to become the largest luxury vacation rental company in Asia-Pacific.
The “cat lady” persona has undergone a chic makeover in the age of Taylor Swift and other celebrity feline lovers.
Another dynamic, glamorous cat fan, Stephanie Chai, founder and CEO of The Luxe Nomad, has her business purring. Asia-Pacific’s largest luxury vacation rental management company has today evolved into a preferred gateway to curated villas around the region, with more than 1,300 rooms spread across 100 properties in Indonesia, Thailand and Japan.
The Luxe Nomad exclusively manages properties in the powder-rich environs of Hokkaido, as well as in Bali, Phuket and Koh Samui — three of Southeast Asia’s most alluring tropical idylls. Given these paradisiacal associations, few would guess that the seeds of the venture were sown in more homespun circumstances.
“In the early days of the business, it was just me, two full-time staff and my two cats in my apartment,” Chai says. “And for the first two years, a team of about eight of us worked out of my living room. It was that small!”
New Zealand-born Chai, a finance grad from the University of Auckland in New Zealand, chose a path less travelled after starting out in the media world as a model and TV presenter. This meant she was comfortable in the limelight even before her start-up journey. And she’s harnessed considerable personal charm and people skills in the most significant role of her career.
“Being on television taught me to think on my feet, which has been invaluable for pitching to owners and fundraising, as you never know what question you’ll get,” she says.
Shifting Gears
Indeed, significant pivots — both by choice and necessity — have been a feature of Chai’s journey as a travel industry entrepreneur. The first major shift came in 2016 when The Luxe Nomad expanded from being a villa booking portal to managing exclusive properties.
“I felt the villa industry represented a sweet spot, as it was high touch versus hotels, and whilst fast developing, the market was very much fragmented and still mom and pop,” she says. “I saw the opportunity to build a trusted villa rental brand across borders.”
By Chai’s admission, the evolution was more protracted than she would have wished.
“Our expansion was slow as in retrospect I probably didn’t push hard enough to convince my board on the pivot back in 2014, but managed to do so two years later,” she recalls. “As a first-time entrepreneur and founder, there was a big learning curve in managing investors and board members, something I have learned along the way.”
Eventually, in 2016, The Luxe Nomad acquired a company in Bali and then in Thailand in 2019. In 2023 the company achieved another milestone as it took a majority stake in NISADE, the largest property management company in Hokkaido, Japan, doubling the business in the last year alone.
Chai’s friendly, natural demeanour is central to her leadership style. She’s quick to laugh during our call and attributes her down-to-earth personality to her high school and university days in New Zealand, a country renowned for its aversion to airs and graces.
Yet her breezy manner belies an entrepreneurial spirit that was sparked at a young age. Born to a Malaysian Chinese father and an Italian/Kiwi mother, Chai spent her childhood in Kuching, Sarawak, where her father ran his business. The enterprising gene was passed down from father to daughter.
“I remember when I was 11 we had an entrepreneurship competition at school,” she says. “I decided to sell brownies and it did so well — though as my father reminded me, I had not paid him for the cost of ingredients! It is easy to avoid not paying for expenses as a child,” she adds with a laugh.
“I loved it so much that I kept selling brownies even after the competition was over,” Chai recounts, laughing as she remembers trying to increase revenue by making the slices smaller and seeing demand drop.
After graduating from that fledgling period as a brownie vendor, Chai faced the biggest challenge of her entrepreneurial life when Covid-19 arrived.
“As the leader of the company, you don’t get to turn up to work stressed or down in the dumps, no matter how hard it gets,” she says. “That’s a side you reserve for only your very senior team. At the top, you have to be the one cheering everyone on and inspiring them to stay positive, and that’s what I did on many Zoom calls. I turned pay cuts into ‘Aren’t we lucky to still have a job?’”
The Luxe Nomad weathered the pandemic, even achieving a 70% group occupancy rate in Bali during the worst of the crisis. And while Chai is under no illusions about the disastrous human and economic costs of the health crisis, she’s philosophical about the business lessons it helped instil.
“God forbid, it ever happens again,” she says. “But Covid taught me how to switch from a growth mindset to a defensive one overnight. I think in all honesty it was great training for anyone in management, particularly in travel, as you had to learn how to survive a black swan event for which there is no playbook and suddenly revenue evaporated overnight,” she stresses.
“If anything, as stressful as Covid was, I knew the silver lining would be that more partners would be open to do a merger and acquisition with us. It is because of the pandemic that partners like NISADE realised the benefits of being part of a larger group versus going at it alone.”
One For All
Chai is also finding that her sense of zen helps her run a company spread across multiple countries and cultures. She fondly refers to her diverse team as a “mini United Nations” and her leadership philosophy centres on understanding local cultures and bringing out the best in her team.
“A strong company culture comes from the top,” she says. “I grew up attending the only international school in Sarawak, Borneo, with 10 or so kids in my class, and hence was used to being around people from all over the world. As a result, I recognise the nuances in different cultures and manage our teams across Asia differently.”
“In Hokkaido, I was mindful that we were seen as the new ownership, so building trust was important. One thing we did was set a crazy sales target for the year and promised a year-end company offsite to Bali if we hit it. We achieved the target and flew 70 people from our Japan office to Bali this year. That cemented trust with our Niseko team as we kept our word to them.”
With travel continuing its incredible post-pandemic comeback, Chai is focused on strengthening The Luxe Nomad’s position in Asia-Pacific and beyond.
The company is making significant tech investments to improve the customer experience, with a goal of making booking properties and experiences as seamless as possible. By the following ski season in 2025/2026, Chai is confident that guests travelling to Hokkaido will be able to book a property and arrange everything from ski lessons to airport transfers through a Luxe Nomad app rather than email.
Another growth area for The Luxe Nomad has been expansion to new locations, such as Furano, an up-and-coming ski resort in Hokkaido that has seen occupancy nearly double year on year. Chai also rhapsodises over Natai Beach in Thailand’s Phang Nga province, just north of Phuket, where The Luxe Nomad just launched two beachfront villa estates, Sava Beach Villas and Coastal Escapes. “It’s the only area around the Phuket region where you have private beachfront luxury villas right on a swimmable beach,” she says. “You can paddleboard, kayak or just relax. One villa at Sava Beach Villas, Malee Sai, even has a pétanque court, while others have a sauna, kids’ playground and beauty spa.”
Chai is excited about what lies ahead. She’s proud of the strides her company has made and keeps making — but she’s not resting on her laurels. “Our goal for guests remains the same: we’re here to inspire you, to ensure you ‘Dream a little. Travel a lot’,” she says. “But our ambitions are always evolving, so from that perspective, we are changing.”
The Luxe Nomad has travelled far from its small-scale origins on Chai’s living room sofa. As the business grows beyond borders, Chai is thinking bigger than ever, one luxury holiday home at a time.