Jack Zhang on Failure, Growth, and Building the Future of Global Finance

In an episode of Grit, the startup podcast hosted by Joubin Mirzadegan, Airwallex co-founder and CEO Jack Zhang shared the extraordinary story behind building one of the world's most valuable fintech companies. The conversation went far beyond fundraising and billion-dollar valuations—it explored personal loss, relentless resilience, difficult leadership decisions, and the mindset required to build a global business from the ground up.

Long before Airwallex became an $11 billion fintech company, Zhang experienced a dramatic reversal that permanently reshaped how he viewed money, ambition, and entrepreneurship. His journey—from working overnight shifts in Australia to turning down a billion-dollar acquisition offer from Stripe—offers invaluable lessons for every founder navigating uncertainty.

Many startup success stories begin with a garage.

Jack Zhang's began with losing everything.

Survival Before Startups

Entrepreneurship wasn't Zhang's immediate escape.

Survival was.

Unable to rely on family support, he worked nearly every job he could find while attending university:

• Washing dishes
• Bartending
• Overnight shifts at a gas station
• Computer repair
• Farm work picking lemons

Some weeks meant working from 4 p.m. until 8 a.m. while still trying to finish his degree.

It's tempting to romanticize hustle.

Jack doesn't.

Instead, he describes those years as a period of simply trying to survive while rebuilding confidence after losing nearly everything.

For founders, it's a reminder that resilience isn't glamorous. Often, it's repetitive, exhausting work that no one sees.

Curiosity Creates Opportunity

Before Airwallex, Zhang tried nearly everything.

Architecture.

Real estate.

Coffee shops.

Burger restaurants.

Software development.

None became his life's work—but each taught him something.

One seemingly ordinary frustration eventually changed everything.

His business partner struggled to send money internationally. Transfers disappeared for weeks because outdated banking infrastructure relied on multiple intermediary banks, limited payment information, and manual compliance checks.

Rather than accept the system, Zhang asked a simple question:

Why can't money move directly?

That question became Airwallex.

Great companies often begin this way—not with revolutionary technology, but with founders who refuse to accept that "this is just how it's done."

Raising a Million Dollars Over Dinner

Every startup has an unbelievable moment.

For Airwallex, it happened over dinner.

After explaining his vision for building a modern alternative to SWIFT, Zhang mentioned he planned to raise $1 million.

Investor Lucy Liu surprised him.

"What if I give you two?"

By the following morning, she had agreed to invest $1 million at a $5 million post-money valuation—and joined as a co-founder.

Years later, that investment became worth hundreds of millions of dollars.

The lesson isn't that fundraising is easy.

It's that conviction attracts believers.

Investors rarely back PowerPoint slides.

They back founders whose clarity makes impossible ideas feel inevitable.

The Danger of Hiring Experience Over Thinking

One of Zhang's most valuable lessons came after Airwallex began scaling.

Like many first-time founders, he hired executives from prestigious financial institutions believing experience would accelerate growth.

Instead, many attempted to recreate legacy banking systems inside a startup designed to replace them.

Looking back, Zhang says one mistake stood out:

He trusted credentials more than first-principles thinking.

Experience matters.

But experience solving yesterday's problems doesn't always solve tomorrow's.

For early-stage founders, this is a critical hiring lesson.

Hire people who can think—not just people who've done the job somewhere else.

Saying No to Stripe

In 2018, Stripe reportedly offered to acquire Airwallex for approximately $1.2 billion.

On paper, it made perfect sense.

The companies were highly complementary.

Investors supported it.

Financially, Zhang and his co-founders would have secured generational wealth.

He nearly said yes.

Then he asked himself a different question:

Would I actually be happy afterward?

The answer wasn't clear.

He realized he wasn't finished building.

Walking away from life-changing money wasn't about ego.

It was about unfinished purpose.

Today, Airwallex is worth many multiples of that original offer.

But at the time, Zhang had no way of knowing the future.

He simply chose the path he believed he would regret least.

Success Doesn't Guarantee Happiness

Perhaps the most surprising moment in the interview comes near the end.

Despite leading an $11 billion company operating across dozens of countries, Zhang admits he still isn't as happy as he was when he was 14 years old building that first magazine.

Why?

Because childhood offered simplicity.

Everyone believed in the mission.

Nobody worried about politics, regulation, organizational complexity, or managing thousands of employees.

As companies grow, leadership becomes less about excitement and more about responsibility.

That's an honest perspective many founders rarely share publicly.

Lessons Every Entrepreneur Can Apply

Jack Zhang's journey offers several enduring principles:

• Hardship can become your greatest competitive advantage.
• Start with painful customer problems, not flashy technology.
• Conviction attracts exceptional people.
• Hire for judgment and adaptability—not just impressive résumés.
• Don't confuse wealth with fulfillment.
• Keep building because the mission matters, not because success is guaranteed.

Final Thoughts

Airwallex didn't emerge from Silicon Valley.

It emerged from adversity.

Jack Zhang's story reminds entrepreneurs that resilience isn't a personality trait—it's a decision made repeatedly when circumstances make quitting feel reasonable.

His journey also challenges one of startup culture's biggest myths.

Building a great company isn't about chasing happiness.

It's about pursuing work meaningful enough to make the struggle worthwhile.

For founders still in the messy middle, that's a lesson worth remembering.