Jack Zhang, CEO of Melbourne-based fintech Airwallex, declined a $1.2 billion acquisition offer from U.S. payments giant Stripe in 2018, a decision that has since reshaped the company's trajectory. Airwallex now reports over $1.3 billion in annualized revenue, a significant leap from the $2 million it generated at the time of the offer, demonstrating the power of long-term infrastructure investment. The company processes nearly $300 billion in annual transaction volume, a testament to its "path of maximum resistance" strategy.
Before founding Airwallex, Jack Zhang navigated a complex path, shaped by early challenges and a persistent entrepreneurial drive. He arrived in Melbourne from Qingdao, China, at 15, barely speaking English, and lived with a host family. When his family's finances faltered, he took on four jobs to fund his computer science degree at the University of Melbourne, according to the Australian Financial Review.
He tended bar, washed dishes, worked graveyard shifts at a petrol station, and picked lemons on a farm during school holidays, a task he described as the most arduous he had ever faced. These experiences instilled a deep understanding of hard work. That knowledge would prove useful later.
Zhang's early ventures ranged widely, from a magazine at age 14 to real estate development. He also managed import-export operations, moving wine and olive oil from Australia to Asia, and textiles in the reverse direction, alongside running a burger chain. The idea for Airwallex crystallized while he operated a Melbourne coffee shop.
His co-founder, Max Li, struggled to pay coffee bean suppliers in Brazil, Indonesia, and Guatemala. Payments frequently disappeared into the correspondent banking system, flagged and frozen by American intermediary banks enforcing OFAC sanctions, sometimes returning weeks later. "That pushed me to really look at how correspondent banking works," Zhang said, "how SWIFT works, and how we could build our own global money movement network." This experience revealed a significant friction point in global trade. Someone had to fix it.
In 2018, at 34, Zhang found himself in Silicon Valley, sitting with Michael Moritz of Sequoia, a powerful investor. Moritz had invited Zhang to his home, a residence Zhang recalled as having multiple floors and a direct view of the Golden Gate Bridge, to discuss a potential sale. Stripe had offered $1.2 billion for Airwallex.
The Melbourne company then reported only about $2 million in annualized revenue. The valuation represented a revenue multiple close to 600 times. Moritz argued that Patrick Collison, Stripe's co-founder, was a generational entrepreneur and that the deal would "compound" into something extraordinary.
Zhang listened carefully. He spent two weeks walking around San Francisco, feeling restless, struggling to form a clear thought. He initially accepted the offer.
However, after flying nearly 8,000 miles back to Melbourne, Zhang reconsidered. "I really went deep on what motivates me to build Airwallex," he explained early this week, speaking from overseas. "I was three and a half years into the business. The business was growing 100 times in 2018. And I only just sort of tasted what it [was like] to be an entrepreneur.
And that's what I'd been dreaming about." Two of his three co-founders had voted against the deal, reinforcing his own reservations. The clearest signal, he noted, came from looking at the whiteboard in his office. The vision remained incomplete: to construct the financial infrastructure enabling any business to operate globally as if it were a local entity.
He pulled out of the deal. The decision now appears prescient. Airwallex currently claims over $1.3 billion in annualized revenue, growing at 85% year-over-year.
It processes nearly $300 billion in annualized transaction volume. This growth, Zhang contends, did not come easily. The company deliberately embarked on what Zhang frequently calls the "path of maximum resistance." This strategy involved painstakingly acquiring close to 90 financial licenses across 50 markets.
Stripe, by Zhang's estimation, holds roughly half that number. Each license, each bank integration, and every local payment rail Airwallex assembled created a deeper, more defensible layer against competitors. "You can't really vibe-code an integration with Mexico's central bank," Zhang said, illustrating the technical and regulatory rigor. "We have to have a secure room – you have to do a biometric scan just to walk in to access the central bank integration." This is not simple software development. Obtaining these licenses proved immensely time-consuming.
In Japan alone, the process required seven years. In some emerging markets, Airwallex had to acquire defunct shell companies whose licenses were no longer issued by central banks, then rebuild the underlying technology entirely. This approach contrasts sharply with many fintechs that layer services atop existing financial infrastructure.
Following the supply chain in this sector means building the rails yourself. The numbers on the shipping manifest — or in this case, the payment network — tell the real story of control and capability. This deep infrastructure ownership offers distinct advantages.
In Japan, for example, while companies like Stripe and Square can process payments, they must immediately transfer funds to a merchant's bank account. Airwallex, holding a fund transfer operator license, can retain those funds within its own ecosystem. This allows customers to issue bank accounts, issue cards, and spend money without it ever leaving the platform.
The foreign exchange economics alone offer substantial savings. A U.S. merchant settling transactions in Australian dollars avoids the typical 2% to 3% conversion fee that processors like Stripe often charge to repatriate funds into U.S. dollars. Instead, businesses can use those local balances to pay local vendors, run payroll, and cover digital marketing expenses, all at interbank rates. company anymore," Zhang explained. "You operate like a company with entities around the world, but without needing to physically set up those entities." This model effectively turns trade policy into foreign policy by other means, by streamlining the financial flows that underpin international commerce.
Zhang's framework, the "path of maximum resistance," defines this slow, intentional build. He noted it took Airwallex six and a half years to reach $100 million in annual recurring revenue. "But after that, it took just over three years to get to a billion," he added. This acceleration underscores the compounding value of foundational infrastructure.
The competitive logic, as Zhang describes it, hinges on owning the infrastructure versus merely utilizing someone else's. If something goes wrong in the end-to-end payment workflow, and you do not control the underlying system, you cannot access the data to explain it to your customer. Extending new products cleanly on top of another company's stack also proves difficult. "Building on top of other infrastructure," he stated, "is simply not scalable." Control of the financial supply chain is critical.
For most of their existence, Airwallex and Stripe have operated in different geographical spheres, targeting distinct customer bases. That dynamic is now changing. Stripe is expanding deeper into international markets, while Airwallex has begun its first serious moves into the United States.
This creates growing overlap. Historically, Airwallex's customer acquisition has focused on CFOs, finance directors, and treasury teams in Australia and Southeast Asia, where the company is well-established. Stripe, conversely, has primarily driven customer acquisition through U.S. developers choosing a default starting point for new companies.
More than 90% of Airwallex customers initially adopt a business account product, with payments and spend management following. Over half use multiple products, Zhang reported. Despite its growth, Zhang acknowledges challenges.
Stripe holds a prominent position as Silicon Valley's "golden child," its privately held shares having created numerous millionaires across the tech industry. This creates a brand recognition gap. Airwallex needs to embed itself into the mindset of engineers and developers, not just finance teams, so that founders instinctively choose its platform. "Our brand is just not there yet," he conceded. "That's a harder competition to win." The competition is being observed closely from several vantage points.
Sequoia backed Airwallex early, with the deal sourced through Sequoia Capital China, which has since spun out and rebranded as Hongshan. It remains one of Airwallex's largest shareholders. Greenoaks Capital, another investment firm, holds stakes in both Airwallex and Stripe.
Zhang dismissed any suggestion of awkwardness stemming from these overlapping cap tables, noting that investors are betting on a large market opportunity. This situation naturally raises questions about valuation. Stripe was valued at $159 billion in a February tender offer, representing a 74% increase from a year earlier, after processing $1.9 trillion in total payment volume in 2025.
Airwallex, valued at $8 billion in December, is roughly a twentieth of Stripe's valuation. However, Zhang pointed out that Stripe's payment volume is only about six times Airwallex's volume. With 85% annual growth and projected revenue of $2 billion within the next year, Airwallex is closing the revenue gap more rapidly than the valuation gap suggests.
The market's eventual recognition of this discrepancy remains an open question. An initial public offering, which Zhang states is at least three to five years away, would force that question into public view. Why It Matters: This intensifying competition between Airwallex and Stripe is not merely a corporate battle; it reflects a broader struggle for control over the invisible infrastructure of global commerce.
For small and medium-sized enterprises (SMEs) and even larger corporations operating internationally, the efficiency and cost of cross-border payments directly impact their bottom line and ability to expand. Airwallex's strategy of building deep, localized financial infrastructure promises to reduce foreign exchange costs and streamline operations, potentially lowering barriers for businesses to engage in global trade. This could mean more diverse product offerings for consumers and more efficient supply chains worldwide, fundamentally altering how money moves across borders.
Key Takeaways: - Airwallex CEO Jack Zhang rejected a $1.2 billion acquisition offer from Stripe in 2018, choosing instead to build extensive financial infrastructure. - The company's "path of maximum resistance" strategy involved acquiring nearly 90 financial licenses across 50 markets, a time-consuming but strategically valuable effort. - The competitive landscape is shifting as both Airwallex and Stripe expand into new geographies, with Airwallex aiming to overcome Stripe's significant brand recognition. Zhang is currently focused on long-horizon targets, including one million customers by 2030 and $20 billion in annual revenue. He also aims to increase average revenue per customer from around $12,000-$13,000 today to roughly $20,000.
A suite of AI-powered autonomous finance products, designed to not just surface data but execute transactions, is rolling out now. Zhang suggests that a decade of financial data across the entire corporate finance stack, from revenue collection to treasury management and vendor payments, has created a training set that no competitor can replicate quickly. The question now is whether this hard-earned infrastructure can significantly erode Stripe's market share.
For now, the competition appears to be playing out at a distance. Zhang and Collison, once friendly during merger talks, did not speak when they both attended Greenoaks Capital's annual gathering last year. The market will watch for further moves as this rivalry unfolds.
Key Takeaways
— - Airwallex CEO Jack Zhang rejected a $1.2 billion acquisition offer from Stripe in 2018, choosing instead to build extensive financial infrastructure.
— - The company's "path of maximum resistance" strategy involved acquiring nearly 90 financial licenses across 50 markets, a time-consuming but strategically valuable effort.
— - Airwallex now reports over $1.3 billion in annualized revenue and processes nearly $300 billion in transactions, growing rapidly.
— - The competitive landscape is shifting as both Airwallex and Stripe expand into new geographies, with Airwallex aiming to overcome Stripe's significant brand recognition.
Source: TechCrunch