Leaning Into the Unknown

By Karen Tee
Photography by Darren Gabriel Leow
Styling by Grace Lim, assisted by Teo Xiu Wen
Grooming by Nikki Fu
05 Jun 2023

The millennial founders of ski and snowboarding company The Ride Side are bringing the slopes and waves to the heart of Orchard Road with the upcoming launch of Trifecta, Asia's first snow, surf, and skate facility.

American tech mogul Sheryl Sandberg may have popularised the phrase “lean in”, but in snowsport circles, it is a term that enthusiasts use to describe conquering the fear of falling.

Artist’s impression of Trifecta, which is slated to open in the latter part of this year

“When snowboarding, the scariest part is having to lean in as that is the only way down,” explains Daphne Goh, co-founder of ski and snowboarding company The Ride Side. “When riders get scared, they tend to lean backwards on the mountains, but that is when they actually fall.”

These days though, Goh and her other two co-founders, Alex Hsu and Terry Tan, are also embracing Sandberg’s more metaphorical aspects of leaning in, especially as they have embarked on their most ambitious venture yet.

Armed with a big dream to make snowsports, as well as surfing and skating more accessible in Singapore, the three millennials are launching Trifecta, a high-tech snow, surf, and skate attraction in Orchard Road.

Touted as the first of its kind in Asia, this complex, which is slated to launch later this year, will offer state-of-the-art training machines for these three popular board sports. These machines are designed to allow users to replicate actual movements on the slopes or on waves for a realistic practice. 

The training areas will also be paired with virtual experiences including an indoor surfing simulator and a VR ski simulator to better mimic the sensations of being on an actual slope or real waves.

“The scale of what we are doing with Trifecta is vastly different from what we are familiar with, which is organising social and fuss-free ski and snowboarding trips. Now that travel has resumed, it does feel like falling back into our comfort zone would be easier but at the same time, leaning into this big venture is exciting,” admits Goh, 32, who oversees marketing and business development. 

Unable to resist another snowboarding analogy, lead web developer and community builder Tan, 35, who is also one of The Ride Side’s lead travel hosts, says they are giving Trifecta the “full send”. He chips in, “It is a concept that when you do a trick, you have to go all out and be committed to it.”

The skate arena will house the world’s first hybrid skate bowl designed for both skateboarding and surfskating

They are driven by a passion to grow the community of board sports enthusiasts here in Singapore and to make these sports – especially snowboarding and surfing – more accessible here. To complement the “trifecta”, a skate arena will house the world’s first hybrid skate bowl designed for both skateboarding and surfskating.

Trifecta is in some ways the missing link to their original business model. They launched The Ride Side in 2015 to offer more interested individuals the opportunity to travel in groups for snowboarding holidays, something which Hsu, 34, found lacking in the market. “I founded the company because I wanted to create something that would give me more opportunities to travel and go snowboarding,” recalls Hsu, who oversees operations and the travel business.

Daphne wears leather jacket and leather dungaree by Coach, boots Stylist's own / Alex wears Necklace by Coach, sweater, leather shorts, and sneakers by MCM / Terry wears knit vest by MCM, trousers by Loro Piana, and Sneakers by BOSS

Hsu and Goh are a couple, while Tan was then a digital nomad living in Niseko. Hsu had befriended Tan during their frequent snowboarding trips there and united by a common passion for snowboarding, it made sense to team up to form The Ride Side.

“The whole idea behind The Ride Side was to make it easier for like-minded people who have the itch to experience more adventurous sports to come together,” says Hsu.

For the company’s first full season in Niseko, Japan in 2016, the company had over 200 travellers sign up over three months. Since then, The Ride Side has organized trips to various parts of Japan, New Zealand, and Europe and they estimate that their community of enthusiasts are about 10,000 to 20,000 strong.

But after several years of running winter trips, they realized that because it is impossible to pick up boarding skills in Singapore, where there is neither snow nor mountainous slopes, many people ended up spending most of their overseas holidays painstakingly learning the basics of the sport.

“When we noticed that many travellers spent very little time riding the slopes, we felt that for them to really be able to experience the sport, it would be better if they could learn the skills in Singapore before travelling abroad. So, we came up with some ideas on how to develop an infrastructure to let people train here,” says Tan.

During the pandemic, when travel came to a standstill, the trio began searching in earnest for a suitable location to create this training complex in Singapore. “The need to have this facility really urgently surfaced when we realized we might not be able to travel to enjoy the sport we love,” says Hsu.

At the same time, they knew their brainchild had the potential to be much more than a niche venue tucked away in a far-flung corner of the island. “Our most important criteria was that we wanted this to be a part of people’s daily routine where they can conceivably go for a surf lesson during lunch instead of the gym or a snowboard run after work. We did not want it to be just a tourist attraction or a one-time sport,” says Hsu.

In 2021, they submitted their concept for Trifecta to a tender held by the Singapore Tourism Board, Singapore Land Authority, and Urban Redevelopment Authority for the vacant site between Somerset Skatepark and Killiney Road. Their youth-oriented facility, which dovetailed nicely with STB’s master plan of transforming Orchard Road into a lifestyle destination, won the tender.

While shopaholics might say that the Orchard Road strip is first and foremost a shopping paradise, Goh points out that there has always been a lifestyle element to visiting this iconic destination.

“Orchard Road is one of the few places you think about when you have a checklist of what you want to explore in Singapore,” says Goh. “Trifecta complements the current businesses as you not only get to shop, eat, and enjoy yourself, you will also be able to experience a hotspot in the area.”

Plus, with board sports growing in popularity and gaining mainstream acceptance – for instance, skateboarding is a new sport added to the Olympics roster – they are confident Trifecta is well placed to foster more youth participation.

Daphne wears double-breasted blazer and straight-leg pants by ANINE BING via NET-A-PORTER / Alex wears Navy jacket and pants by Loro Piana / Terry wears Striped shirt and blazer by BOSS

“Skateboarding has become a CCA sport in international schools and is trickling down to the local schools,” observes Hsu. During the pandemic, The Ride Side also expanded into summer sports by offering skateboarding, surfskating, and longboarding lessons, which turned out to be very popular among locals looking to escape the mundanity of the pandemic life. 

“What we would like to do is to also make snowboarding and surfing as easy now that there is a facility to train at. For any sport, we need to start them young to push growth in it,” says Hsu.

It is also very much aligned with their fearless ethos of leaning in. Goh says, “We see this not just as a space for existing snowboarders and surfers, but also part of the larger picture of encouraging more people to go out of their comfort zone and to dare to try new things.”