Why Great Startups Stall Before They Scale

Steve Osler is CEO of Wildix, a sales-oriented unified communications solution.

In 2005, my brother and I sat in a pub in Northern Italy. The town of Caldonazzo likely wouldn’t register on most startup maps, but there we sat, scribbling ideas on a napkin. We weren’t thinking about global markets or becoming a major player. We were just trying to fix something broken: business communications.

Dropped calls, outdated systems and no interoperability—the frustration wasn’t with the technology itself, but rather with the widespread acceptance of dysfunction. So, we did what seemed obvious to us by building a solution.

We never expected someone outside of Italy to email us, asking, “Can you bring this solution here?” That simple question changed everything. Our vision shifted overnight from local to global, and just like that, we faced a choice. We could wait until we were ready or leap into the unknown.

We leapt.

That imperfect decision is what led to Wildix, now serving over a million users in 135 countries, and it’s why I’m writing this.

If you’re a founder today, scaling isn’t just about ambition or technology. The real challenge, the one no one prepares you for, is the system.

The Challenge Of Expanding

Let’s start with Europe. It’s what I know best, and it’s one of the most complex markets in the world.

From the outside, Europe appears unified, but in practice, it’s a maze. Every country has its own tax codes, labor laws and compliance frameworks. Expanding across borders feels less like growth and more like resetting your company each time.

I learned this the hard way. When we entered France, we received two VAT assessments from the same office. One said we owed money. The other said we’d overpaid. When we asked for clarification, the answer was a shrug: “It depends who’s looking.”

We hit the same roadblock in Germany. The Italian tax office claimed we were leaving too much revenue there, while Germany insisted the opposite. Both sides were adamant. No universally applied rules—just a harmonized framework interpreted differently in each country.

Many of these roadblocks aren’t even codified. They’re interpretations, practices passed down like folklore, enforced with the weight of law but none of its clarity. At one point, we spent tens of thousands of euros on tax advice from a top consultancy. After months of analysis, their conclusion: “It depends.”

That kind of uncertainty costs more than money. It costs time, momentum and energy. And while this is particularly acute in Europe, it’s not unique to it.

Why Some Of The Best Ideas Don’t Scale

This isn’t about lacking talent. Whether in Europe, Southeast Asia or Latin America, the world is full of brilliant teams and bold ideas. But too many startups stall—not because of product-market fit or ambition, but because of the structural friction they face when trying to scale.

Some shrink their ambitions while others shift operations abroad, usually to the U.S., where the rules are clearer, the market larger and the system, for better or worse, more predictable.

To me, these aren’t strategic pivots—they’re concessions. When survival becomes the goal, growth gets left behind. In many regions, ambition doesn’t die in the garage; it dies at the border.

The Turning Point

With that said, change is underway. Across Europe—and increasingly beyond—there’s growing recognition that long-term reliance on foreign infrastructure, particularly U.S.-based platforms, may not be sustainable for every context. Momentum is building around the idea of buying local, supporting homegrown infrastructure and creating environments where founders can build and scale without needing to relocate or exit prematurely.

This shift isn’t driven by nationalism or protectionism, but by a desire for resilience, optionality and long-term competitiveness. Policymakers are beginning to acknowledge what many founders have experienced firsthand: the current system too often favors consolidation over innovation, and location still dictates opportunity.

In Europe, this is visible in initiatives like France’s efforts to reduce dependency on U.S. tech platforms, and broader EU moves to enable cross-border small and medium-sized enterprise (SME) growth. Even the World Economic Forum has underscored that digital sovereignty will be central to Europe’s relevance in the global economy. Rising tariff tensions and supply chain volatility have added a geopolitical dimension to what began as an economic debate.

Importantly, these issues extend well beyond Europe. Founders in emerging markets face many of the same structural challenges. What they’re asking for isn’t insulation from global competition—it’s the chance to compete on more equal footing. They want the freedom to scale without being penalized for where they were born.

The global opportunity is still on the table, but only if we create systems that let founders stay, build and win, wherever they are.

What I’d Tell Founders Today

If I could go back to that pub in 2005, here’s what I’d tell myself and any founder looking to scale:

• Move before you feel ready. The perfect moment never comes. If you wait, someone else will move faster and take the opportunity.

• Ask for the actual rule. If a consultant says something is “impossible,” don’t just accept it. Many barriers sound legal but are really just assumptions or outdated practices.

• Stay lean as long as you can. Every new legal entity adds complexity and cost. Don’t expand your structure until the demand clearly justifies it.

• Fail early and fail forward. If you can figure out how to scale in a market as complex as Europe, you’ll be equipped to scale anywhere.

• Respect rules, not rituals. Bureaucracy can be loud, but not all of it is law. Challenge tradition when it creates friction.

The Time To Build Is Now

Building Wildix from a pub in Northern Italy into a global company wasn’t seamless, but we didn’t wait for permission. And neither should you.

We’ve got a real shot at building something that keeps talent, grows ideas and competes globally. But that won’t come from big talk or press releases—it’ll come from actually fixing the system, so the people doing the building can move forward without constantly fighting uphill.

Digital sovereignty doesn’t start with governments. It starts with founders, and founders don’t wait.

Forbes Technology Council is an invitation-only community for world-class CIOs, CTOs and technology executives. Do I qualify?