She was a high-flying model who appeared in Nivea and Citibank advertising campaigns, and even had a cameo role in the 2010 movie Fair Game that starred Naomi Watts and Sean Penn.
Miss Stephanie Chai, 31, then decided to quit modelling for the tech start-up scene. "I have always wanted to start my own business since I was young," she said.
Spotting a gap in the Asian market for an online luxury travel portal, such as those found in the United States and Europe, she put in $60,000 of her savings to start TheLuxeNomad.com in July 2012.
This is a members-only website that offers flash sales and the best available rates at luxury hotels and resorts. Membership is free. "I started it for people like myself who love to travel cheap but stay luxurious, and it is also something that I am passionate about," she said.
In its first six months, she paid her staff from her own pocket.
"It was very stressful, as I did not know when I would run out of money," she said.
At first, TheLuxeNomad.com only had flash sales with discounts of up to 70 per cent for luxury hotels in Asia. She soon realised that it was not a viable business model.
"We can have only so many flash sales, so we started to offer best available rates," she said.
She knew she had to offer something different. Through contacts in the entertainment industry, she got Taiwanese actor Godfrey Gao, Thai actress Ase Wang and other celebrities to review the hotels as a way of attracting potential customers.
Business picked up and has continued to grow, she said. Last August, TheLuxeNomad.com received funding of around $900,000, from Innosight Ventures, Zipan Enterprises and a silent partner, to further expand the business.
Contract obligations do not allow her to disclose revenue figures, she said, but she did reveal that sales went up by 60 per cent last November and 160 per cent in December, compared with an average month.
The portal now has eight employees, all women, up from two at launch. It offers rates at 400 hotels in 40 destinations, compared with just 60 hotels at launch.
The celebrity factor has helped to grow the business. Actor-singer Vanness Wu and his Singaporean wife Arissa Cheo booked their honeymoon hotel through TheLuxeNomad.com.
Hong Kong model Cara G, who is one of the portal's celebrity reviewers, said: "As an expectant mother, the last thing I want to be doing is spending hours online searching for the perfect resort. With TheLuxeNomad.com, life is made easy with its curated list of top hotels and villas on private sale. Luxe for less, why not?"
However, Miss Chai is not resting on her laurels. "No matter how well you perform this month, you have to start thinking of how to surpass it next month," she said.
In order to get ahead of bigger rivals such as Trivago and Agoda, TheLuxeNomad.com launched an online travel magazine with articles posted daily by its staff and partner bloggers.
She said: "The missing link in TheLuxeNomad.com was content, and we want our e-mail to be so interesting that users will always read it."
In future, she plans to start a service that automatically sends a customised travel guide to people who have booked a hotel with the portal. The guide will offer information relevant to the chosen destination, including maps, must-see places and other tips.
Passion, she said, is what still spurs her on. "Money is not something that drives me here. It is waking up and feeling excited that pushes me," she said.
Get a copy of The Straits Times or go to straitstimes.com for more stories.