Stephanie Chai and the business of being trusted

Stephanie Chai took five minutes to decide she wanted to start a travel business. A friend had sent her a link to an American booking site. She liked travelling, liked beautiful places, and had been looking for an idea. Her reply was swift. The education that followed would be considerably less so.

The Luxe Nomad launched in Singapore in July 2012. In its first month, sales came to S$2,000, including a booking made by Chai herself. A founder can be her own customer, although it does complicate the applause. She had put S$60,000 of savings into the venture. The first month's receipts made a rather modest welcome party for that money.

She chose Singapore partly for its investment community. Her friends in entertainment helped make the new business visible: stays at appealing properties became reviews and photographs shared online. She had a network, a small team and an eye for an image. What she still had to build was a reason for people to trust a company they had never heard of.

Today, she is the founder and CEO of a business managing holiday properties across Indonesia, Thailand and Japan. Her ambition has become more exacting with experience. Getting someone to click on a lovely villa is one task. Being responsible for what happens when they arrive is another. Chai gradually chose the latter, with all the awkward conversations and operational detail it brings.

Before the villas, a very persuasive eyeliner

The urge to make things and sell them arrived early. During school holidays in New Zealand, Chai dreamed up an eyeliner that worked like a pen with several colours. She drew the design and sent it to The Body Shop, Clinique and Lancôme. No manufacturer took up the proposal. Letters and free products came back instead. For a schoolgirl, that was at least a respectable response rate.

At King's College in Auckland, her subjects included calculus, statistics, economics, accounting and English. English was the one she particularly enjoyed. She and a friend could divert their teacher into telling stories, including his recollection of seeing the Berlin Wall. Accounting later proved useful in business. Her affection for calculus remained rather more restrained.

New Zealand was one part of her upbringing; Kuching, in East Malaysia, was another. She has described childhood there as quiet enough that school-holiday travel felt like an event. Those journeys gave her something to anticipate. Later, modelling assignments would supply a different kind of departure: travel built into the working week, with a shoot waiting at the other end.

She studied finance and international business at the University of Auckland while pursuing modelling. The combination makes more sense than a neat career-switch story allows. A camera teaches a person to present herself. Commercial work also involves contracts, rates and negotiation. Chai credits a petite but formidable Thai agent with teaching her to bargain; she later negotiated some overseas contracts herself.

Her first online venture was Wedding Guide Asia, launched in 2009. The bridal directory came before the travel company, an early exercise in bringing businesses and customers together on a website. By the time The Luxe Nomad arrived, Chai had already worked across modelling, television and online publishing. She had accumulated useful experience without collecting it under a single job description.

The photograph is the easy part

For a travel company, a photograph can do an enviable amount of work. Blue water requires little explanation. In 2015, Chai's advice on Instagram was unapologetically visual: choose beautiful images and give credit when sharing other people's photographs. She understood the appeal of the scene. Behind it was a founder carrying a laptop onto flights and tidying a desktop that she admitted could get messy.

Her own description of herself was cheerfully unpolished: “Funny, I think, passionate and a dreamer.” The hesitation before funny is a nice touch. In the same conversation, she talked about cold-calling and getting things done with limited money. Daydreaming had a place in her working life. So did asking strangers for something and following through.

It would be easy to mistake the former model's visibility for the whole business. Chai's memories of the early years are less decorative. She recalls spending a Saturday night cropping 1,000 photographs for the website. Finding the right technology team took three attempts. Fundraising meant learning unfamiliar terms and meeting sales conditions. There was plenty to do after the pictures had been chosen.

She has also resisted treating every social occasion as a hunt for useful contacts. Her approach to smaller businesses was to help where possible, even when a collaboration offered them more than it offered her. On the practical side, she would ask acquaintances whether they knew someone at a brand, or contact executives on LinkedIn. Friendship and an introduction need not be the same transaction.

“Funny, I think, passionate and a dreamer.”

Stephanie Chai, 2016

A holiday with a maintenance checklist

A working-week diary from 2018 catches Chai in motion: Hong Kong, Kuala Lumpur, Bali, then Tokyo. On the Hong Kong leg she checked out boats for a possible event with her friend Antonia Dacruz. By noon she was back online. The sunlight had been real; so were the departmental updates waiting for her.

In Bali, she was checking maintenance and service at Villa Suami, listening to staff and considering changes to the menu. Even a unicorn pool float made the list. A holiday business contains some decisions that would look peculiar in a bank's board minutes. They still have to be made by somebody.

The villa-management expansion became established in 2017, including the acquisition of a Bali operator. Chai's work now reached beyond marketing a property to inspecting it, training teams and pitching owners. The distinction was tangible. A guest could forgive a website for displaying an unappealing photograph. A disappointing stay would be much harder to repair with better copy.

There was a human limit to growth, too. Some properties were too secluded or too far away to take on. She wanted to see them herself. However appealing a location looked online, the business had to be able to work there. Luxury was acquiring a geography of practical constraints.

The owner has to hand over the keys

Chai had proposed a move towards full management in 2014. Winning her board over took another two years. She has acknowledged that she could have argued harder for the change sooner. It is a revealing admission from a founder: conviction about an opportunity and the ability to persuade the people financing it do not always develop at the same speed.

The attraction was a fragmented villa industry, where a recognisable brand could cross borders. But an owner's trust could take months to win. “Every villa is someone’s baby,” she said. A management agreement asks for more than permission to advertise. It gives another team responsibility for a place into which its owner has put money, taste and feeling.

Japan brought a larger step in 2023, when The Luxe Nomad took a majority stake in NISADE. One financing meeting involved pandan cake and pineapple tarts. Chai spent much of two hours discussing the investor's other businesses, and came away with an offer of half the funding. It was a reminder that a deal has people on both sides of the figures.

Once the Japanese team joined the group, trust still had to be earned. Chai promised a Bali offsite if the team reached its sales target. They did, and 70 people travelled from Japan to Bali. An incentive became a demonstration that the new owners would keep a promise. The destination was familiar; the relationship was still being built.

Who gets to rise?

Chai's early company was predominantly female. By 2023, she described a more balanced split, while pointing to women who had worked in operations, senior leadership and general management. Her account of that history is practical rather than ceremonial: early reservations and marketing vacancies attracted few male applicants, while hiring should still come down to the best candidate.

Asked what power meant to her, she answered, “The ability to implement change.” That definition makes room for decisions well below the level of a public speech. Who is allowed to advance? Who gets credit? Who is trusted to run a department? Her stated advice includes remaining humble and sharing recognition with the team.

The growing company also changed the usefulness of doing everything herself. In the earlier business, Chai had been closely involved in finance, operations and marketing, down to Instagram copy. Hiring a chief operating officer in 2016 marked a change in how responsibility could be distributed. In her productivity advice, delegation features more prominently than any elaborate morning ritual.

“The ability to implement change.”

Chai on the meaning of power, 2023

The mountain, finally

In 2015, Chai said she would love to try skiing in Niseko. By March 2026, she was offering her own guide to the place. On one Sunday visit she arrived at seven in the morning and was on the mountain by eleven. “Never waste the weekend!” was her verdict. The former item on a wish list had become somewhere she knew well enough to advise other people.

Her recommendations are pleasingly specific: reserve the instructor and dinner tables ahead of time; try Rin Izakaya for a cosy meal, Bang Bang for yakitori or Del Sole for pizza. She likes visiting the spring-water fountain at Fukidashi Park in the warmer months. A destination becomes more personal once the recommendations go beyond the view from a room.

Elsewhere, her travel memories return to company and food. Venice matters because it was her maternal grandparents' hometown. A pear-and-gorgonzola gnocchi dish remained in her memory afterwards. In Italy she has travelled with friends arriving from several different countries, delighted by how much they laugh together. The founder selling a place to stay is often describing the people she wants beside her.

Her 2026 inclusion in EY's Entrepreneurial Winning Women Asia-Pacific programme places her alongside other founders preparing to grow internationally. The published ambition is to reach US$100 million in gross booking value within three to five years, with further acquisitions part of the plan. It is a target, rather than a result already in the bag.

Chai's business has travelled a long way from its first website. Her own story gives the distance a more useful measure than the itinerary alone: she has learned to negotiate, ask for backing, make a case to a board and look after teams across borders. Five minutes was enough to choose an idea. The years afterwards have been spent making other people comfortable saying yes.