Jack’s Place has lasted 60 yrs, but it doesn’t want to be a biz people “only remember from the past”

“Nostalgia becomes dangerous if it prevents a business from improving,” says 3rd-gen director Alvin Say

There are restaurants you eat at, and restaurants you grow up in. Jack’s Place, for many Singaporeans, is firmly the latter.

Most Singaporeans would recognise its green-and-white checkered tablecloths anywhere. You might even remember the sizzle of a steak arriving at your table, or servers weaving between diners with gravy boats in hand.

This year, the homegrown chain celebrates its 60th anniversary. Any restaurant that survives six decades is remarkable. One that remains emotionally meaningful across multiple generations is something else entirely.

Vulcan Post spoke with Alvin Say, third-generation owner at Jack’s Place, about the brand’s evolution over the decades.

A cook boy’s unlikely inheritance

The Jack’s Place story begins with an immigrant who arrived with little and built something lasting through sheer grit and skill.

Say Lip Hai came from Hainan and found work as a cook boy for British troops stationed in Sembawang, where he learned the foundations of Western cooking—roast beef, Yorkshire pudding, rich gravies, the rhythms of classic British-style dining.

By the 1960s, he was running his own venture, Cola Restaurant, when a chance encounter changed everything.

A British housewife, impressed by his food, introduced him to her husband, Jack Hunt, who owned a pub and restaurant called Jack’s Place along Killiney Road. Lip Hai was invited to manage the catering and restaurant operations.

When Jack eventually returned to England in 1974, he sold the business to Lip Hai for S$28,000.

As the new owner, Say began reshaping the business. The pub gradually gave way to a restaurant, and while it initially leaned towards Italian influences, other culinary traditions soon found their way onto the menu. French cuisine, in particular, left a lasting mark.

In its early years, the restaurant’s S$3.80 set lunches became a hit with oil rig workers and office employees along Orchard Road. Lip Hai, committed to using fresh ingredients, would personally head to the market each morning on his Vespa to source supplies.

The restaurant’s 60-seater outlet at Killiney Road quickly outgrew itself. In 1977, Lip Hai opened a second outlet at the former Yen San Building. When queues formed at Killiney, he would even ferry waiting customers to the new location down the road.

Jack’s Place also doubled as a lively watering hole in those years. The bar counter was often packed, and Lip Hai would order whiskey by the hundred. Though closing time was officially 11PM, service frequently ran late to accommodate late-night regulars.

Jack’s Place had over 15 outlets at its peak

As Singapore’s HDB new towns expanded in the 1980s and ’90s, Jack’s Place followed suit. Its first heartland outlet opened in Ang Mo Kio and remains the brand’s oldest outlet today.

The restaurant’s positioning was deliberate: dependable, familiar, and welcoming.

Back then, Western dining still carried an air of novelty and occasion. Jack’s Place wanted to create a space that didn’t feel intimidating or exclusive—a place where ordinary families could enjoy a Western meal comfortably.

At its peak, the chain operated more than 15 outlets across the island, becoming a familiar presence in neighbourhood malls and town centres.

In 2008, the family formalised its business under a corporate umbrella, JP Pepperdine Group. Alongside the flagship Jack’s Place steakhouse brand, the group expanded its portfolio with Eatzi Gourmet, a halal-certified arm that spans steakhouses and a catering division.

A family business across generations

Today, the business is managed by the second and third generations of Lip Hai’s family, alongside a team of long-serving professionals.

Alvin frames his role as stewardship rather than ownership. “We see ourselves less as owners and more as stewards of the brand,” he says. “Every generation has a responsibility to protect what people love about Jack’s Place, while making sure it stays relevant for the next generation of diners.”

That stewardship comes with its own tensions. Members of the third generation were encouraged to gain experience elsewhere before returning to the family business—a deliberate choice to ensure fresh perspectives.

You are not just managing a company. You are managing something tied to your family history and identity. Alvin Say, Director of Jack’s Place, JP Pepperdine Group

When generational disagreements arise, the tie-breaker is always the same question: what is genuinely better for the customer?

As Jack’s Place is often associated with nostalgia, Alvin takes a measured view when asked whether it is an asset or a liability.

 “It can be both,” he said. “Nostalgia is valuable because it creates emotional trust that newer brands cannot easily replicate, but it becomes dangerous if it prevents a business from improving.”

“We don’t want to become a brand that people only remember fondly from the past. We want to remain part of people’s present-day lives as well.”

That tension between preserving heritage and avoiding stagnation is one Jack’s Place has had to navigate carefully.

Some elements of the menu have remained largely unchanged for decades: sizzling steaks on cow-shaped hotplates, lobster bisque, baked potatoes. These are not just signature dishes; they are emotional touchpoints. Change them too much, and you risk erasing the memories that bring customers back.

At the same time, dining habits have shifted significantly. Today’s customers are more health-conscious, more visually driven, and far more attuned to global food trends.

They are no longer comparing Jack’s Place only with other steakhouses, but with cafés, lifestyle concepts, and a wave of well-capitalised overseas brands—particularly from China—that have entered Singapore with aggressive pricing and polished social media playbooks.

“Many of these brands move very quickly,” Alvin observes. “They operate with strong capital backing and are highly aggressive in pricing, marketing, and expansion.”

Playing the long game

To keep up with Singapore’s challenging F&B industry, operations have changed significantly behind the scenes, from technology and food safety systems to supply chain management and central kitchen support.

While continuing to protect the classics, the brand has also gradually introduced newer ideas and offerings to appeal to today’s diners.

COVID-19 was a defining moment of reinvention. With dining rooms closed, Jack’s Place had to pivot its entire business toward delivery and ready-to-eat meals almost overnight.

“It forced us to accelerate a decade’s worth of digital transformation into a few months,” Alvin shared. The shift was painful, but it proved the organisation could move faster than it had believed.

Historically, the brand has also weathered multiple economic downturns by staying lean and anchored to its core identity as a value-for-money family destination.

Part of Jack’s Place’s longevity, Alvin said, is not accidental. It comes from taking a long-term view.

While the chain operates around 12 outlets today, down from a peak of more than 15, growth is no longer defined by outlet count.

Instead, the focus has shifted to something harder to measure: strengthening the experience, improving consistency, and earning relevance with a new generation of diners who did not grow up eating their first steak at Jack’s Place—but who might, given the right reason to walk through the door.

• Find out more about Jack’s Place here.
• Read other articles we’ve written on Singaporean businesses here.

Also Read: These 3 young S’pore hawkers put cheese in a curry puff. They made S$500K in their 1st year.

Featured Image Credit: Jack’s Place/ rainbows via Trip.com