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Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN

Airwallex is the most insane story in startups. Jack Zhang is the Co-Founder and CEO of Airwallex, one of the world’s fastest-growing global payments and financial infrastructure companies. Since founding the company in 2015, Jack has scaled Airwallex to over $100B in annual payment volume, $360M in run-rate gross profit, and a global team of 1,500+ employees. Under his leadership, Airwallex has raised over $900M from investors including Square Peg, Lone Pine, and Tencent. ---------------------------------------------- In Today’s Episode We Discuss: 00:00 Intro 01:03 From Lemon Factory and Petrol Station to Billionaire: The Early Days 11:39 $5M Side Hustle While Working Full-time: How Jack Did It 23:14 Failing Three Times Before Product-Market-Fit 30:22 The Term Sheet That Got Pulled and Lost Matrix $1BN 35:28 Why We Rejected Stripe’s $1.2BN Acquisition Offer 51:37 0-$1B Transaction Volume in 9 Months: How Shein Saved Airwallex 01:15:52 When COVID Hit, They Lost 50% of Revenue Overnight 01:19:03 We F****** Up Scaling Internationally... & Burnt $200M/year 01:23:14 Why Jack is Taking Out a Line of Debt for $70M 01:24:00 The Truth About Secondaries and How Much is “Enough” 01:28:00 The Hiring Mistakes that Almost Broke the Culture ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on X: https://twitter.com/HarryStebbings Follow Jack Zhang on X: https://twitter.com/awxjack Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #jackzhang #airwallex #founder #ceo

Jack ZhangguestHarry Stebbingshost
May 25, 20251h 35mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

From Lemon Factory To Fintech Unicorn: Jack Zhang’s Relentless Ascent

  1. Jack Zhang, CEO and co‑founder of Airwallex, recounts his journey from financially insecure immigrant teenager in Australia working 16-hour menial shifts to building a multi‑product, global fintech platform approaching $1B+ in annual revenue. He describes a decade of side businesses that made him millions before Airwallex, multiple near‑death company moments, and turning a stranger’s $1M angel check into a stake now worth around $1B. The conversation covers failed product iterations, hard pivots, rejected term sheets, a declined $1.2B acquisition offer from Stripe, and the discipline learned after raising and burning hundreds of millions of dollars. Throughout, Zhang emphasizes resilience, founder quality over ideas, and his ambition to build an AWS‑like global financial infrastructure that can rival Citi or HSBC by 2035.

IDEAS WORTH REMEMBERING

5 ideas

Early hardship can build abnormal resilience and drive.

Zhang’s experience losing family financial support at 16, working 100‑hour weeks in physically demanding jobs, and self‑funding his education created a baseline of toughness that later made startup stress and long hours feel manageable rather than exceptional.

You can be financially successful yet still feel unfulfilled without mission‑fit work.

Before Airwallex, Zhang ran multiple side businesses (import/export, real estate, phone accessories, etc.) generating millions annually, but he openly says he didn’t enjoy any of them; he kept his coding job because he wanted to eventually build something meaningful and technical at scale.

Founding stories often hinge on unlikely, high‑conviction believers.

Lucy, a 20‑something ex‑banker Zhang met for the first time at his coffee shop, wired $1M to his personal account within days, pre‑incorporation, for 20% of Airwallex; that first‑time angel check is now roughly a $1B position, illustrating the outsized impact of one early believer.

Winning companies usually endure multiple product and strategy failures before product‑market fit.

Airwallex’s initial P2P FX algorithm, SME invoicing product, and early Tencent/Mastercard platform bets all failed to scale; PMF only arrived after pivoting to API‑based infrastructure for large enterprises and landing a few huge customers like Shein and tuition‑payment platforms.

Founders must balance aggressive ambition with financial discipline.

After raising large rounds (e.g., $100M from DST), Zhang admits he had no budget, rapidly scaled headcount 6–7x, over‑expanded internationally without PMF, and repeatedly nearly ran out of cash—lessons that later pushed him toward profitability while still growing ~90–100% annually.

WORDS WORTH SAVING

5 quotes

I did 100 hours a week for about 20 years, dude.

Jack Zhang

Making money is not gonna make you happy. I started more than 10 businesses and realized I didn’t like any of them.

Jack Zhang

Why has this thing been around for 50 years and processes trillions a day? Why can’t we fundamentally build a new system to move money like data?

Jack Zhang (on SWIFT and cross‑border payments)

This is the girl you met for the first time in your life…and she’s offering you $2 million.

Jack Zhang (on Lucy, Airwallex’s first angel investor)

We basically never grew below 100% from 2015 to 2023.

Jack Zhang

Jack Zhang’s early life, financial hardship, and work ethic formationPre‑Airwallex entrepreneurial experiments and building financial securityAirwallex founding story, early funding, and the $1M angel checkProduct pivots, failed ideas, and eventual product‑market fit in cross‑border paymentsNear‑death moments, fundraising cycles, and investor dynamics (Tencent, Sequoia, DST, SoftBank, Hedosophia)Stripe’s attempted $1.2B acquisition and Zhang’s decision to remain independentScaling to a global multi‑product fintech platform, culture, hiring, and leadership lessons

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