The Hard Truths of International Business Expansion: Lessons from the Trenches

What they don’t tell you about taking your business global in an increasingly complex world

When we started expanding SureStep internationally in 2009, the world looked very different. The G7 dominated global economics, the US dollar reigned supreme, and “going global” seemed like a straightforward extension of domestic success. Fast-forward to 2025, and nearly everything about international expansion has changed.

COVID reshuffled the deck. Political upheaval in the US created uncertainty. The rise of BRICS has challenged Western economic dominance. The US dollar has lost significant ground. And through it all, we’ve learned some expensive lessons about what it really takes to build an international business.

If you’re a North American company considering global expansion, here’s what we wish someone had told us before we started writing checks and boarding planes.

The “Easy Market” Trap: Why Australia Broke Our Assumptions

Let’s start with the biggest myth in international expansion: that cultural similarity equals business ease.

Australia should have been our slam dunk. English-speaking, similar legal systems, established trade relationships with North America. On paper, it was the perfect first international market. In reality, Australia became one of our most challenging expansions.

Despite sharing a language and many cultural touchpoints, Australia proved to be a tough nut to crack. The business culture operates differently than North American expectations. Regional dynamics are complex and deeply entrenched—Melbourne residents barely acknowledge Sydney residents as part of “their” Australia, which tells you something about the level of parochialism you’ll encounter.

The lesson? Don’t let surface similarities fool you into thinking any market will be easy. Cultural and linguistic familiarity can actually be dangerous because it creates false confidence that masks deeper structural differences.

Sometimes these cultural gaps appear in the most unexpected moments. On my first trip to Singapore, I was delayed a day in Toronto when they needed to de-ice our plane. This caused me to miss my connection in Hong Kong and arrive a day late for a crucial client meeting. When I explained the delay to my Singaporean client—someone who had never been outside Singapore beyond Indonesia—I mentioned that “they had to de-ice the wings of the plane.” She looked extremely confused and asked, “Why did they put ice on the wings of the plane?”

It hit me that someone who’d never experienced winter weather had no context for understanding ice formation on aircraft. Cultural norms and expectations can be turned on their head where you least expect it, even in seemingly straightforward business conversations.

If Australia is complex, imagine what truly foreign markets will throw at you.

When Geopolitics Rewrites Your Business Plan Overnight

Here’s something that wasn’t in any expansion playbook from 2018: what happens when the geopolitical ground shifts beneath your feet.

We had built a solid presence in Hong Kong, leveraging it as a gateway to mainland China and broader APAC markets. Then China’s National Intelligence Law effectively eliminated any form of data privacy in Hong Kong. For a risk and analytics firm handling sensitive financial data, this wasn’t just a compliance issue—it was an existential threat.

We’re now pulling out of Hong Kong entirely. Every single one of our clients has made the same decision, relocating to Singapore instead. Years of relationship building, local staff development, and market positioning evaporated due to regulatory changes we couldn’t have anticipated.

The new reality of international expansion is that stable regulatory environments can disappear overnight. Political changes in major powers now ripple through their spheres of influence in ways that can fundamentally alter your business model. Build this uncertainty into your planning, and always have exit strategies ready.

The Pricing Reality Check That Nobody Talks About

Here’s a hard truth that will hit your P&L immediately: your North American pricing probably won’t work internationally.

Prices that clients readily pay in USD in North American markets are often far higher than most international markets will bear. We discovered that most APAC markets will pay roughly 50% or less of our standard North American rates.

Singapore stands out as the exception—they’ll pay top dollar for quality services. But for most other markets, you need to completely recalibrate your pricing expectations. This isn’t just about currency exchange rates or cost of living differences. It’s about fundamentally different perceptions of value and willingness to pay.

This pricing reality forces some uncomfortable strategic questions: Can you deliver your service profitably at 50% of your home market rates? Do you need to develop a different service model for international markets? Are some markets simply not viable given the pricing constraints?

Don’t make the mistake of assuming you can “educate” international markets about your value proposition. The market sets the price, not your spreadsheets.

The Partnership Decision Matrix: When to Cut Your Losses

Not every market is worth the squeeze, no matter how large it looks on paper.

We’ve concluded that Thailand, Indonesia, Vietnam, and India are all partnership-only markets for us. The bureaucratic complexity of establishing business presence and banking facilities simply isn’t worth the time and resources required. In Thailand and Indonesia specifically, language barriers and taxation complexity make local partnerships essential.

Here’s what tips the decision toward partnership rather than direct presence:

Regulatory complexity that requires deep local expertise: If you need a lawyer and an accountant just to understand how to open a bank account, partner instead.

Cultural barriers that go beyond language: Surprisingly, language isn’t always the biggest factor. We’ve completed full implementations in Thailand without anyone on our team speaking Thai. But cultural nuances around business relationships, decision-making processes, and trust-building often require local partners.

Markets where the setup costs exceed reasonable payback periods: If it takes two years just to establish legitimate business presence, your opportunity cost may be too high.

The partnership route isn’t admitting defeat—it’s recognizing that your resources are better deployed where you can establish direct presence effectively.

What “Local Presence” Actually Means (Hint: It’s Not What You Think)

Every expansion guide talks about establishing “local presence,” but they rarely define what that actually means in practice.

From a legal standpoint, real business presence requires local incorporation and local staff. That much is straightforward. But from a market acceptance standpoint, the timeline is sobering.

To be seen as truly “local enough” to overcome parochialism can take a decade or more of consistent presence and relationship building. It’s not just about having an office and staff—it’s about becoming part of the local business community fabric.

The good news is that establishing legitimate business presence does make the parochialism issue largely disappear in day-to-day operations. You transition from being seen as “foreign company trying to do business here” to “local business with foreign ownership.” But true insider status? That’s measured in generations, not quarters.

This has practical implications for your expansion timeline and relationship-building strategies. Don’t expect to be treated as a local player just because you’ve rented office space and hired regional staff.

The New Rules for a Fragmented World

The world has become more uncertain and difficult to navigate since 2018. The rise of BRICS, the relative decline of G7 dominance, currency volatility, and increased regulatory nationalism have all made international expansion more complex.

Some tactical adjustments we’ve made:

Build regulatory redundancy: Have backup markets ready when primary markets become politically risky. Our Hong Kong experience taught us that even stable jurisdictions can change overnight.

Price for uncertainty: Build risk premiums into your pricing for politically volatile markets. The additional margin helps offset the costs of potential rapid exits.

Focus on quality markets over quantity: Rather than trying to establish presence everywhere, we’ve focused resources on markets that offer both stability and pricing power—primarily Singapore and select Western markets.

Leverage dual tax avoidance treaties strategically: These remain one of the few areas where international cooperation still works well. For example, paying maximum 17% tax in Singapore eliminates double taxation in Canada. Understanding these structures can provide significant competitive advantages.

The Bottom Line

International expansion in 2025 is fundamentally different from what it was even five years ago. The old playbooks assumed a stable, Western-dominated world order that no longer exists.

Success requires accepting some uncomfortable realities: markets that look similar may be surprisingly complex, geopolitical stability can’t be assumed, your pricing probably won’t work internationally, and true local acceptance takes generational time.

But for companies willing to navigate these realities with clear eyes and flexible strategies, international markets still offer significant opportunities. The key is approaching expansion as a long-term strategic investment rather than a short-term revenue grab.

Most importantly, be prepared to make hard decisions quickly. Whether that’s exiting markets that become politically risky, accepting lower margins in price-sensitive regions, or choosing partnerships over direct presence in complex markets.

The world has become more fragmented and uncertain, but it’s also created opportunities for nimble companies that can adapt to new realities. The question isn’t whether international expansion is worth it—it’s whether you’re prepared to do it on the world’s terms, not your own.

SureStep has been navigating international expansion since 2009, with operations across Toronto, London, New York, Singapore, and Australia. These lessons come from real experience in real markets, not consulting theory.