Cross-cultural marketing lessons don’t always arrive in tidy frameworks or training decks. Sometimes they appear in the middle of a 50,000-person pop concert. Sometimes they emerge during a diplomatic luncheon with two prime ministers. And sometimes — unexpectedly — both moments echo the same truth. This is a story about what a global popstar, two small nations, and a budgeting app from Dunedin can teach us about how small players win on the world stage.
If you were alive in 2023-2024, it would have been hard to escape the noise generated by The Eras Tour. Taylor Swift brought her 3.5-hour show all around the world, and her longest run of shows anywhere on Earth took place in Singapore. Six consecutive concerts in March 2024!
And something magical happened there, every single night, in front of a 50,000-strong crowd. During her “Red” era rendition of We Are Never Ever Getting Back Together, she’d sing the lyric “Like, we are never getting back together,” then pass her mic to the human manifestation of sunshine — her backup dancer Kam Saunders — who’d usually say “like ever!”
But for every single concert in an international location, he’d replace “like ever” with a local, often colloquial phrase and often one in the native language. On night one in Singapore, Kam replaced it with the iconic Singlish phrase: “No lah!”
In Singapore, that little segment grew so popular — and Kam’s Singlish got so consistently better — that there were calls for him to be granted honorary citizenship. He got his own write-up in The Straits Times, fans made reels compiling all his variations, and he became a national treasure overnight.
This moment cut through like a cool knife through kaya (if you know you know). It showed me localisation in action, and to see it play out in real time, with real energy and real-world ripples, was incredible.
If you take the time and effort to understand — really understand — the local culture, customs and zeitgeist, you don’t just build trust and camaraderie with your audience. You build a shared empathy that transcends demographics.
The famed Taylor Swift friendships bracelets in action.
I can hear the challenges mounting already:
“Of course it’s easy if you’re Taylor Swift. She’s got a gigantic world stage. Her brand is ubiquitous, so any small localisation, performative or not, is bound to be picked up by media all over the world.”
And that’s fair.
But the localisation lesson doesn’t end with a pop concert. To understand why it matters for the rest of us — those without global stages or billion-dollar brands — we need to step out of a stadium in Singapore and into a completely different setting. One where the stakes are higher and the spotlight smaller, yet the strategy looks oddly familiar.
So let’s jump to October 2025, into a skylit event hall on Auckland’s waterfront. Specifically, a state luncheon in The Cloud on Queen’s Wharf, celebrating the signing of the Comprehensive Strategic Partnership between Singapore and New Zealand.
I was invited to attend the lunch, hosted by Prime Minister Christopher Luxon, as a member of the Kiwi tech export community, and also, I’m assuming, as a Singaporean who calls Aotearoa home.
As I sat and listened to Singapore Prime Minister Lawrence Wong address the room, a connection between The Eras Tour and that present moment landed clearly for me. Here’s what he said:
“Singapore and New Zealand are small, open economies, outward-looking, connected to the world, and deeply connected to each other…
Ours is a partnership anchored by trust and a shared strategic outlook…
May these bonds continue to grow and flourish as our nations move forward together…
The strong bonds between our two countries will provide anchors for all of us to navigate these uncertainties ahead and emerge stronger together.”
Hearing his words in that familiar Singapore accent, a learning dropped into my lap — metaphorically, thankfully, because I was wearing white and a real mishap would’ve been disastrous.
In Singapore, a single moment of cultural fluency on a concert stage lit up an entire stadium (and country). There in Auckland, cultural fluency wasn’t delight — it was diplomacy. It was how two small nations, without giant megaphones, navigate a world filled with bigger players.
For small countries that export to the world, like Singapore and New Zealand, which don’t have global stages, massive resources, or cultural ubiquity, the question is: How do we stay relevant and competitive in a world stacked against us?
The answer is simple, but not easy:
This philosophy — trust, values, partnership — is exactly what small, successful countries do well.
And it’s also exactly what PocketSmith has learned on its own journey.
Prime Ministers Lawrence Wong (L) and Christopher Luxon (R) celebrating the signing of the Comprehensive Strategic Partnership between Singapore and New Zealand.
Sitting in that room in Auckland, I realised how deeply this mindset shapes the way we grow at PocketSmith. We’re not a global juggernaut. We’re a small, bootstrapped, remote team in New Zealand, building something for the world from one of the far edges of it. And that reality demands a different kind of strategy.
Before we enter a new market, we spend real time understanding it. We don’t guess or project, and we are almost hyper-aware of unconscious bias or unsurfaced assumptions.
When we expanded into Australia, we didn’t assume we “got” Aussie culture because we’re closer in time zone and share a sporting rivalry. We spent time on the ground. We wanted to understand what the day-in-the-life of an Aussie Household CFO actually looked like.
So we listened to actual Australians talk about money, trust, shame, humour, habits. We tested language. We adjusted tone. We worked with people in-market who told us what resonated — and what didn’t.
We take the same approach with the UK and other communities we’re keen to serve. We don’t go in with preconceived notions. We’re intensely aware of the cultural gulf that exists between countries, more so around attitudes to money. We start from a place of humility, respect, and curiosity.
Because we’ve all seen what happens when brands skip this work:
PocketSmith works with organisations that already have trust in their markets — people whose values feel aligned with ours. We want mutual wins, not transactional relationships. We look for collaborators who operate at a similar scale and who believe in long-term partnership rather than short-term extraction.
Just like Singapore and New Zealand, our strength isn’t scale.
It’s trust. Shared values. Cross-cultural empathy. And the willingness to do the groundwork that others overlook.
These are profound strengths when you’re small.
And this is where we loop back to music — because whether you love or hate Taylor Swift, she’s not the point. She’s the contrast, the cultural monolith whose smallest gestures echo around the world, if you will.
PocketSmith is not that. And we don’t need or want to be.
If PocketSmith were a musical act, we would obviously not be Taylor Swift. This is about to get mildly controversial (and I’m sure a few PocketSmithers would have different takes), but I think we’d be the band with a fiercely loyal following people tell their friends about. The group whose songs chart in Denmark, Jamaica, and Japan for reasons nobody can quite explain — but no one begrudges.
We’re small, but we’re loved. We’re niche, but for the right people, we’re essential. And we’re proud to be building from the edges — thoughtfully, humbly, and with the kind of cultural curiosity that small players never take for granted.
Because whether it’s a stadium in Singapore, a state luncheon in Auckland, or a money management app built in Dunedin, the same truth shows up again and again:
When you don’t have the biggest stage, you don’t compete by being louder. You succeed by understanding deeper.
And that’s how the small — countries, artists, and yes, companies like ours — make their mark on a very big world.
From teeny tiny Dunedin to a diplomatic event with multiple national leaders — small players can play big, too!
Field Notes From Cross-Cultural Marketing is a new series by PocketSmith CMO Dora Yip, exploring the unexpected places where culture, identity, and marketing meet in the real world. Each piece examines what it means to build a global personal finance brand from a small country with curiosity, empathy, and heart.
Dora is Head of Marketing here at PocketSmith. She’s the mum of two boys, and calls both Singapore and New Zealand home. She’s obsessed with succulents, sci-fi and bubble tea, and is waiting for the day a novel will combine all three. Maybe she should just write it herself.
