Prabowo Widodo
At the age of 34, just three and a half years into the demanding journey of running his startup, Jack Zhang found himself in a position that few entrepreneurs ever reach: sitting across from Michael Moritz, one of Silicon Valley’s most formidable investors from Sequoia Capital. The setting was Moritz’s elegant San Francisco home, boasting multiple floors and an unobstructed panorama of the iconic Golden Gate Bridge, a backdrop to a momentous proposition. Stripe, the formidable payments giant, was extending an offer to acquire Zhang’s burgeoning Melbourne-based company, Airwallex, for a staggering $1.2 billion. At the time, Airwallex commanded an annualized revenue of approximately $2 million, making the offer an almost irresistibly high revenue multiple, hovering near 600 times. Moritz, a seasoned venture capitalist, presented the case with conviction, highlighting Stripe co-founder Patrick Collison as a "generational founder" and arguing that the acquisition would allow Airwallex’s potential to "compound" into something truly extraordinary. Zhang listened intently, grappling with the monumental decision. He spent two weeks wandering the streets of San Francisco, restless and overwhelmed, eventually assenting to the deal.
Yet, the definitive "yes" proved fleeting. Following his initial agreement, Zhang embarked on a nearly 8,000-mile journey back to his home base. This transatlantic flight became a period of profound introspection. "I really went deep on what motivates me to build Airwallex," Zhang recounted earlier this week 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." The entrepreneurial spirit, freshly ignited and rapidly accelerating, proved a more potent force than the allure of an early exit. Adding weight to his internal conviction, two of his three co-founders had independently voted against the proposed acquisition, providing a crucial external validation. However, the most unequivocal signal, Zhang recalls, came from the whiteboard in his own office. The company’s ambitious vision remained etched there, still unfinished: to construct the foundational financial infrastructure enabling any business, anywhere in the world, to operate seamlessly as if it were a local entity. This unfulfilled mission solidified his resolve, leading him to ultimately decline Stripe’s lucrative offer.
The Genesis of a Vision: A Founder’s Journey and the Inception of Airwallex
Zhang’s entrepreneurial drive and resilience are deeply rooted in a challenging personal history that predates Airwallex. He was born in Qingdao, a bustling port city in northeastern China, and at the tender age of 15, he made the significant move to Melbourne, Australia, unaccompanied by his parents. Arriving with a minimal grasp of English, he navigated life with a host family, quickly adapting to a new culture and language. His formative years in Australia were marked by hardship, particularly when his family’s finances experienced a severe downturn. To support himself through a computer science degree at the University of Melbourne, Zhang took on an array of demanding jobs, often juggling four simultaneously. As reported by the Australian Financial Review, these included bartending, washing dishes, working graveyard shifts at a petrol station, and enduring the physically taxing labor of picking lemons on a farm during school holidays—a job he frequently cites as the hardest he ever had. These experiences instilled in him an unparalleled work ethic and a profound understanding of the value of perseverance.
After graduating, Zhang spent several years immersed in the high-stakes world of finance, writing trading code in the front office of an Australian investment bank. While the position offered considerable remuneration, it ultimately failed to provide him with a sense of "deep fulfillment." This internal dissatisfaction fueled his desire for something more impactful, more aligned with his inherent drive to build and create. Before the genesis of Airwallex, Zhang had already embarked on an impressive array of entrepreneurial ventures, estimated to be around ten in total. These included launching a magazine at the ambitious age of 14, venturing into real estate development, orchestrating import-export operations—shipping Australian wine and olive oil to Asia, and textiles in the reverse direction—and even establishing a burger chain. Each of these endeavors, regardless of their ultimate success, served as a crucial learning ground, honing his business acumen and deepening his understanding of diverse markets and operational complexities.
The pivotal idea for Airwallex finally crystallized while Zhang was running a coffee shop in Melbourne. It was during this period that his co-founder, Max Li, encountered persistent and frustrating challenges when attempting to pay coffee bean suppliers located in Brazil, Indonesia, and Guatemala. Payments would frequently vanish into the opaque and labyrinthine correspondent banking systems, often flagged and frozen by American intermediary banks enforcing OFAC sanctions rules, sometimes only bouncing back weeks after their initial dispatch. This chronic inefficiency and lack of transparency proved to be the catalyst. "That pushed me to really look at how correspondent banking works," Zhang explained, "how SWIFT works, and how we could build our own global money movement network." The existing global financial plumbing, designed for a different era, was clearly inadequate for the demands of modern cross-border commerce, presenting a glaring opportunity for innovation.
The $1.2 Billion Crossroads: A Defining Moment
The offer from Stripe, facilitated by Michael Moritz, represented not just a financial windfall but also a validation of Airwallex’s early potential. In 2018, the fintech landscape was rapidly evolving, with a growing appetite for innovative payment solutions. Stripe, already a revered name, was actively expanding its global footprint, seeking to integrate promising technologies and talent. Moritz, with his legendary track record at Sequoia, was a key figure in identifying and backing transformative companies, making his personal involvement in the acquisition discussions particularly significant. His invitation to his home, a rare gesture, underscored the seriousness of Stripe’s intent and the perceived strategic value of Airwallex.
The proposed valuation of $1.2 billion for a company with only $2 million in annualized revenue was an extraordinary multiple, reflecting the intense competition for promising fintechs and the perceived future growth potential. For many founders, such an offer from a market leader like Stripe, championed by a titan like Moritz, would be an undeniable exit strategy, promising both financial security and the opportunity to integrate into a larger, influential organization. Zhang’s initial "yes" was a testament to the compelling nature of the proposal and the weight of the moment. The two weeks he spent in San Francisco, deliberating, reflect the immense pressure and the profound internal conflict of choosing between a guaranteed, life-changing payout and the unquantifiable potential of an unproven vision.
However, the decision to ultimately decline the offer was driven by a deeper conviction that transcended immediate financial gain. Zhang’s reflection during his journey back to Melbourne, coupled with the support of his co-founders, reinforced the nascent company’s unique mission. The vision articulated on that whiteboard – "to build the financial infrastructure that lets any business operate anywhere in the world as if it were a local company" – was not merely a business strategy; it was a blueprint for a fundamental shift in how global commerce would function. Zhang’s own challenging background, his years of unfulfilling work in investment banking, and his myriad previous entrepreneurial attempts had all culminated in Airwallex. The prospect of foregoing the chance to see this deeply personal and ambitious vision through to fruition proved too great a sacrifice. It was a decision rooted in the intrinsic motivation of creation, rather than acquisition.
The Path of Maximum Resistance: Airwallex’s Unconventional Growth Strategy
Airwallex’s subsequent growth trajectory has vividly demonstrated the prescience of Zhang’s decision. The company now boasts more than $1.3 billion in annualized revenue, exhibiting a robust year-over-year growth rate of 85%. Its platform processes an impressive transaction volume approaching $300 billion annually. This remarkable expansion, Zhang readily admits, "none of it has come easily – and Zhang argues that’s precisely the point." This ethos underpins what he frequently refers to as the "path of maximum resistance" – a strategic approach that has deliberately chosen the most arduous route to building foundational infrastructure.
This path involves painstakingly acquiring close to 90 financial licenses across 50 markets, a stark contrast to competitors like Stripe, which Zhang estimates holds roughly half that number at best. The process of securing these licenses is immensely time-consuming and complex. In Japan alone, for instance, the regulatory approval process stretched over seven years. In some emerging markets, the company faced the unique challenge of having to acquire existing "shell companies" whose specific licenses were no longer being issued by central banks, then completely rebuilding the underlying technology to meet modern standards and integrate them into Airwallex’s global network.
Zhang emphasizes the stringent security and technical requirements involved in these integrations. "You can’t really vibe-code an integration with Mexico’s central bank," he noted, highlighting the seriousness of the task. "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 level of deep, regulatory-compliant integration is not merely "regulatory window dressing." It provides Airwallex with a distinct competitive advantage. In markets like Japan, while competitors such as Stripe and Square can process payments, they are typically required to immediately transfer funds out to the merchant’s local bank account. Airwallex, armed with its fund transfer operator license, can legally hold these funds within its own ecosystem.
This capability unlocks a suite of powerful functionalities for its customers. A business using Airwallex can issue local bank accounts, issue cards, and spend money without the funds ever needing to leave the platform. The foreign exchange economics alone are substantial. For example, 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 back into U.S. dollars. Instead, the merchant can leverage those local balances to pay local vendors, run payroll, and cover digital marketing expenses, all at significantly more favorable interbank rates. "You don’t really operate like a U.S. company anymore," Zhang elaborated. "You operate like a company with entities around the world, but without needing to physically set up those entities." This allows businesses to achieve true global operational fluidity without the burden of establishing multiple legal entities in each country, simplifying compliance and reducing costs.
The deliberate, slow build of this intricate infrastructure has been foundational to Airwallex’s accelerated growth in recent years. As Zhang explains, "It took us six and a half years to get to $100 million in annual recurring revenue. But after that, it took just over three years to get to a billion." This demonstrates the compounding effect of foundational infrastructure; once the complex groundwork is laid, scaling becomes exponentially faster. The competitive logic, in Zhang’s view, boils down to a fundamental distinction: owning infrastructure versus merely building upon someone else’s. Without end-to-end control of the payment workflow, companies lack the granular data necessary to diagnose issues for customers. Furthermore, extending new products cleanly on top of a third-party stack is inherently constrained. "Building on top of other infrastructure," he asserts, "is simply not scalable."
The Looming Battle: Airwallex vs. Stripe
For much of their respective lifespans, Airwallex and Stripe have largely operated in distinct geographical territories and targeted different customer segments. Airwallex historically found its primary buyers within the CFO’s office in Australia and Southeast Asia—finance directors, treasury teams—where the company is now deeply entrenched. This required a sales motion focused on enterprise-level financial decision-makers. In contrast, Stripe’s customer acquisition has been predominantly driven by U.S. developers, who instinctively turn to its platform as a default starting point for new companies and online ventures. This divergence created a relatively clear competitive field.
However, this comfortable separation is rapidly diminishing. As Stripe intensifies its push into international markets, and Airwallex makes its first serious inroads into the United States, the competitive overlap is growing significantly. Industry analysts predict that this convergence will lead to an increasingly direct confrontation for market share in key global regions. While both companies operate in the broader fintech space, their initial customer acquisition strategies have shaped their product approaches. More than 90% of Airwallex’s customers first engage with its business account product, with payments and spend management capabilities following as natural extensions. Zhang notes that over half of their customer base is now utilizing multiple products, indicating a strong platform stickiness and integrated financial workflow.
Despite Airwallex’s robust growth and differentiated strategy, significant challenges remain, which Zhang does not attempt to minimize. The most prominent is Stripe’s entrenched position as Silicon Valley’s "golden child." Its privately held shares have famously minted millionaires across the tech industry, granting it an almost mythical status among founders and developers. This translates into a substantial brand gap that Airwallex must bridge. To truly compete on a global scale, Airwallex needs to embed itself deeply into the consciousness of engineers and developers—not solely finance teams—so that its platform becomes an instinctive choice for new ventures. "Our brand is just not there yet," Zhang conceded. "That’s a harder competition to win." Building developer trust and mindshare requires not just superior technology, but also extensive community engagement, accessible documentation, and a developer-first ethos that has been a hallmark of Stripe’s success.
The burgeoning competition between these two fintech titans is being observed closely from multiple vantage points. Notably, Sequoia Capital, through its now spun-out and rebranded Hongshan (formerly Sequoia Capital China), was an early backer of Airwallex and remains one of its largest shareholders. Furthermore, the investment firm Greenoaks Capital holds stakes in both companies, creating an interesting dynamic of overlapping cap tables. Zhang, however, dismisses any suggestion of awkwardness stemming from these shared investors. He notes that these sophisticated investors are ultimately betting on the vastness and continued expansion of the global payments and financial infrastructure market, implying that there is ample room for multiple dominant players. Their diversified investments reflect a strategic hedge against market uncertainties and a belief in the long-term potential of both companies.
Valuation Discrepancy and Future Ambitions
The valuation disparity between Airwallex and Stripe remains a focal point for market observers. In a February tender offer, Stripe was valued at an astonishing $159 billion—a 74% increase from the previous year—after processing an estimated $1.9 trillion in total payment volume (TPV) in 2025. Airwallex, in contrast, was assigned an $8 billion valuation in December following its Series G funding round, roughly a twentieth of Stripe’s valuation. However, Zhang points out a critical discrepancy: Stripe’s payment volume is approximately six times Airwallex’s ($1.9 trillion vs. approaching $300 billion), not 20 times. This suggests that, based on current transaction volumes, Airwallex may be significantly undervalued by the market. With an 85% annual growth rate and projections pointing towards $2 billion in revenue within the next year, Airwallex appears to be closing the revenue gap with Stripe at a pace faster than the current valuation gap would suggest.
Whether the market will eventually recognize this potential and adjust Airwallex’s valuation accordingly is a separate question—one that an initial public offering (IPO) would undoubtedly force into the open. Zhang indicates that an IPO is still a strategic target, likely three to five years away, allowing the company to further mature, consolidate its market position, and demonstrate sustained profitability.
In the interim, Zhang remains intently focused on a set of ambitious, longer-horizon targets for Airwallex. By 2030, the company aims to reach a million customers and achieve an impressive $20 billion in annual revenue. Concurrently, it plans to significantly increase its average revenue per customer (ARPC) from the current $12,000-$13,000 range to approximately $20,000. A significant part of this future growth strategy involves the rollout of a suite of AI-powered autonomous finance products. These are envisioned as sophisticated "agents" that will move beyond merely surfacing data to actively executing transactions and managing financial workflows autonomously. Zhang posits that Airwallex’s decade-long accumulation of proprietary financial data—spanning the entire corporate finance stack from revenue collection and treasury management to vendor payments and expenses—has created a unique and invaluable training set for these AI models. This vast, specific dataset, he suggests, represents a competitive moat that no rival can replicate overnight, providing a distinct advantage in the race to automate and optimize global financial operations.
The Unspoken Rivalry
The journey of Airwallex, from a bold rejection of a significant acquisition to its current status as a formidable player in global fintech, is a testament to Jack Zhang’s unwavering vision and strategic tenacity. The competition with Stripe, once geographically distant, is now becoming increasingly direct, particularly as both companies expand into each other’s historical territories. The underlying battle is not just for market share, but for the future architecture of global business finance.
The personal dynamic between the two founders, Zhang and Collison, offers a subtle reflection of this evolving rivalry. While they were reportedly friendly during the merger discussions years ago, their paths have since diverged. A poignant anecdote highlights this: at Greenoaks Capital’s annual gathering last year, both Zhang and Collison were present, yet they did not exchange a single word. This unspoken acknowledgment underscores the intensifying competition and the high stakes involved as Airwallex strives to carve out its unique place in the global financial landscape, proving that the "path of maximum resistance" can indeed lead to extraordinary destinations.
