May 26, 2025 · 1h 35m · 20vc
Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
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In this deep-dive interview, Airwallex Co-Founder and CEO Jack Zhang shares his extraordinary journey from a penniless sixteen-year-old working grueling manual labor jobs in Australia to building a global financial technology giant valued at over $6 billion. He details the high-stakes pivots, near-death fundraising crises, and the philosophical convictions—including rejecting a $1.2 billion acquisition offer from Stripe—that drive his vision to revolutionize the global payment landscape.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Harry as informed peer 2.1 Guest teaching 2.6 Guest disagreement 0.8 Harry pushing back 1.2
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 29:35 Jack calls Harry a bad investor
When Harry admits he wouldn't back Jack based on his background without knowing the business, Jack playfully rejects his framing, declaring 'then you are a bad investor.'
Hardest push from Harry ▶ 1:21:20 Harry challenges $6.2B valuation multipleHarry directly challenges Jack's recent round pricing, questioning why he took a ~6x ARR multiple on a business growing at 90% year-over-year.
Biggest teaching moment ▶ 1:21:30 Jack reframes revenue multiples to gross profitJack corrects Harry's simplified ARR multiple critique by re-centering investor evaluation on gross profit ($115M) and post-2021 market realities.
Harry holds his own ▶ 1:21:20 Harry presses on top-tier growth rate valuation discountHarry demonstrates strong venture market domain knowledge, pressing Jack on why public markets and private investors are refusing to reward a 90% growth rate at $700M ARR.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Welcoming Jack Zhang and the Lemon Factory Question | 1 | 1 | 0 | 0 | Harry opens with standard background questions about Jack's early life in Australia and working in a lemon factory. Jack warmly shares his backstory without friction. | |
| Meeting Co-founders and Early Entrepreneurial Ventures | 1 | 2 | 0 | 0 | Jack describes balancing computer science studies with 16-hour work shifts across bars and petrol stations. Harry listens attentively with basic follow-ups. | |
| Hardship as the Foundation of Business Resilience | 2 | 2 | 1 | 1 | Jack dismisses complaints about founder burnout, contrasting them with real manual labor hardship. Harry agrees and shares his own perspective on working long hours. | |
| Becoming a Side-Hustle Millionaire | 1 | 3 | 1 | 1 | Harry expresses surprise at Jack making millions from side hustles like import/export and real estate while working full-time. Jack downplays the complexity of B2B trading. | |
| The Origin of Airwallex and the Broken SWIFT Network | 2 | 4 | 0 | 1 | Jack educates Harry on SWIFT's 1970s architecture, highlighting intermediary bank hops and 140-character limits. Harry asks about SWIFT's continued dominance. | |
| Finding True Career Alignment and Early Business Pitches | 1 | 2 | 0 | 0 | Jack recounts early discussions about QR vs NFC payments and meeting early investor Lucy who offered $2M on a $5M valuation. The exchange is friendly and storytelling-focused. | |
| Raising the Seed Round and the Challenge of Scale | 1 | 1 | 0 | 0 | Jack details Lucy wiring $1M before signing paperwork and forcing co-founders to resign from their jobs. Harry listens in fascination. | |
| The Unsigned Wire Transfer and Lucy's Legendary Return | 2 | 2 | 1 | 1 | Jack recounts Matrix Partners signing a term sheet and then pulling it back. Harry asks about the valuation details and expresses disbelief at the VC's conduct. | |
| The Term Sheet Pullback and Cap Table Irony | 3 | 3 | 3 | 2 | Jack teases Harry by saying he would be a bad investor for not backing him based on his background alone. Harry defends his focus on founder resilience. | |
| Yuri Milner and the $100 Million Series C Meeting | 3 | 2 | 1 | 1 | Jack describes meeting DST's Yuri Milner who asked only about his upbringing before offering $100M. Harry shares his thesis on founder-led generational companies. | |
| Stripe's Acquisition Offer and the Pivot to Macquarie Bank | 2 | 3 | 0 | 1 | Jack explains cold calling Macquarie Bank to build a custom FX engine connected to interbank liquidity. Harry asks clarifying questions about execution. | |
| Early Failures and the Stalled Tencent Pitch | 2 | 2 | 0 | 1 | Jack explains raising a $60M valuation Series A despite early product failure, and how Tencent's founder stalled the deal. Harry asks how he pitched without revenue. | |
| A High-Stakes Demo with Tencent | 1 | 2 | 0 | 0 | Jack tells the story of a live demo glitching during a high-stakes meeting with Tencent executives. Harry listems enthusiastically to the narrative. | |
| The Illusory "Dream Cap Table" | 1 | 2 | 0 | 0 | Jack outlines how strategic partnerships with Tencent and Mastercard failed to deliver initial volume, leading to cash crunch. Harry stays in listening mode. | |
| Pivoting to APIs and the Square Peg Lifeline | 2 | 3 | 1 | 1 | Jack describes a 48-hour weekend sprint to build alternative payment rails into China to save their Shein contract. Harry expresses excitement over the high-stakes execution. | |
| Declining Stripe's $1.2 Billion Acquisition Offer | 2 | 3 | 1 | 2 | Jack details turning down Stripe's $1.2B offer after Patrick Collison flew to Shanghai. Harry pushes on the personal financial upside Jack left on the table. | |
| A Founder's Commitment to the Long Game | 2 | 3 | 1 | 1 | Jack admits to lacking financial discipline and burning through Series C cash to expand product lines. Harry asks whether the rapid spending was alarming. | |
| The Multi-Product Transition and Hyper-Hiring | 2 | 3 | 1 | 1 | Jack discusses the initial failure of international expansion due to lack of product-market fit and commercial talent. Harry probes on the root causes of the mistake. | |
| Navigating the SoftBank Collapse and COVID-19 | 2 | 2 | 0 | 1 | Jack shares the drama of closing a Series D during the early COVID-19 market crash after SoftBank pulled out. Harry asks about investor sentiment during the crisis. | |
| Early Revenue Milestones and Stripe Valuation Context | 3 | 3 | 1 | 2 | Jack reveals revenue was only $2M when Stripe offered $1.2B. Harry highlights how staggering that valuation multiple was relative to standard metrics. | |
| Navigating Public Market Multiples and the Recent $6.2B Valuation Round | 6 | 5 | 3 | 6 | Harry aggressively questions Jack on why he priced his recent round at $6.2B on $700M ARR (a ~6x multiple). Jack reframes the valuation around $115M gross profit and public market multiples. | |
| Betting Big: Taking $70M in Personal Debt to Buy Back Secondaries | 3 | 3 | 2 | 3 | Jack reveals taking $70M in personal debt to buy back secondary shares. Harry challenges secondary liquidity guidelines for early vs late stage founders. | |
| The Dual Realities of Being a Chief Executive Officer | 2 | 3 | 1 | 1 | Jack shares learnings on hiring and firing traditional bankers who lacked startup conviction. Harry asks what Jack would do differently in hindsight. | |
| Fundraising Strategy and the Influence of Top-Tier VC Brands | 3 | 3 | 2 | 2 | Jack shares a story about Michael Moritz inviting him to his home to convince him to sell to Stripe, and notes why he doesn't invest in early-stage startups himself. Harry asks quickfire questions. |
Statements from this episode (70)
Jack Zhang ran early Airwallex without a budget or financial discipline
“I don't know what is financial discipline, so I don't have a budget. I'm just, like, higher as fast as possible, just blow it all up.”
Airwallex grew from zero to $1B transaction volume in nine months
“So we went from zero to a billion dollar transaction volume within, like, nine months.”
Airwallex sustained over 100% annual growth from 2015 to 2023
“So we basically never grow below a hundred percent from 2015 to 2023.”
Airwallex accelerated ARR from $500M to $700M in five months
“We went to, like, five hundred million dollar AR in August last year, then hit, like, 600 in November, 700 in January, fab.”
Jack Zhang worked 16-hour daily shifts during college
“I basically work like between four to 1130 and in a bar. And once that's finished, I started working a petrol station from midnight to eight AM. So I literally work 16 hour street. And that's, you know, like, Four or five days a week.”
Jack Zhang calls Airwallex CTO Jacob Li a hundred times smarter
“And my CTO Jacob, he's like one year older than me but like a hundred times smarter.”
Early hardship and competition build unmatched startup resilience
“I think when you grow up that if you taste, you know, what success looks like early, you know, whether it's spot or any type of mass competition or Olympic competition or any type of competition or any sort of team spots, the tough experience you know, when I …”
Startup burnout complaints show a lack of real hardship perspective
“The people ask, you know you know, I get burnout. I mean, I'm just, you know, working too hard and, you know, blah, blah, blah. I'm like, dude, what are you talking about? You know, do you know what is, you know, tough life looks like, you know, like me in, in…”
Jack Zhang worked 100 hours a week for 20 years
“Well, I did a hundred hours a week for about 20 years, dude.”
Jack Zhang earned $2M-$5M annually from side hustles before founding Airwallex
“And, you know, I'm, you know, make 200,000 a year on my full-time job more or less. And I make, you know, two, three, four, five million dollars a year on the other side hustle as kind of that business is getting more mature.”
B2B import-export requires only matching buyers and suppliers
“It's actually pretty easy. You know, you think about it, right? You literally just find a supplier, find a buyer, and you're not a producer. You're not a, you don't need to do any marketing. It's just B to B, right? You just, all you need to do is finding buye…”
Jack Zhang accumulated over $10M by age 29 from side hustles
“I probably made like, you know, more than ten million dollars when I was 28, 29, and I had you know, financial security.”
Jack Zhang scaled his side real estate business to $50M AUD projects
“At that time my real estate business is getting kind of real scale, right? You know, we start building like 40, 50 apartments, you know, 40, fifty million Aussie dollar project.”
Airwallex originated from cross-border payment issues with co-founder Max Lee
“One of the guys running that for me was my co-founder Max Lee. He's the head of product design. He went become architect and then started the real estate business with me started the coffee shop with me and which, you know, we found the foreign change and inte…”
Jack Zhang started over 10 side businesses before founding Airwallex
“So I started like probably 10 plus businesses, and what I really concluded is I don't like any of them.”
Jack Zhang kept coding job while making 10x salary on side businesses
“I keep my job of writing code. Even I'm making 10 times the money on the site. So I never resigned.”
Co-founder's name match on OFAC list blocked early Airwallex payments
“My co-founder's name is, is Max Lee. The same name is on the OFAC blacklist. So whoever that he's sending a payment using his personal name, because at that time, you know, we're still using personal name to sending money around the world. And his name, his pa…”
Peer-to-peer cross-border netting requires billions in volume to function
“When we actually build the algorithm and we realize the amount of volume we needed to make that take off, you know, it's like billions of billions.”
Airwallex's first angel offered $2M within one hour of meeting
“I made a pitch. And she's like, how much money are you raising? I'm like, oh, I'm probably going to raise a million US. And she's like, what about if I give you two million? You know, this is a girl that you met for the first time in your life and you only, yo…”
Airwallex raised its initial $1M angel investment at a $5M post-money valuation
“We agreed that she's going to invest a million because I don't want her own 40% of the company. She's going to invest a million dollar, a five million dollar post for 20% of the company.”
Angel investor wired $1M to Jack Zhang's personal account without paperwork
“Then, like, by Monday, I got a tax message from my bank account from my bank, like, which is CBA. It's like, you got a million US dollar wire to your personal bank account. Like, obviously, I'll give her the bank account, but like, I just didn't expect that sh…”
Airwallex's first angel investor stopped investing after subsequent deals failed
“I think she made a few other investments and then didn't turn out to be good afterwards, and I think she stopped investing.”
Jack Zhang resigned from his bank job the day $1M wire arrived
“I literally got the money, and I resigned the same day.”
Every Australian VC rejected Airwallex early on
“Because all the VCs kind of rejected me in Australia. It was only three VC.”
Matrix Partners signed an Airwallex term sheet then revoked it
“But I think one of the founders of the VC, that is the metrics partners, and they give the term sheet they signed, and they took it back. Yeah, so they basically said I had a call with the founder after they signed a term sheet, and they were like, oh, I don't…”
Airwallex nearly died three times before Square Peg saved its Series A+
“No, so SquarePak invested in Series A+. Essentially, that's, you know saved us from dying. So we, there's like three times that we almost died, and then and that's the second time that we almost run out of money. SquarePak invested”
Blackbird and AirTree invested at $6.2B after rejecting Airwallex multiple times
“Blackbird and Airtree was the two largest VC in Australia together with, you know, SquarePak, the three biggest VC. Yeah, but Airtree and Blackbird you know, rejected us multiple times and they now joined the right, they wrote the largest check at 6.2 billion …”
Airwallex raised at a $60M valuation with zero revenue
“We only got like a hundred customers by that time. And we were raising at a sixty million dollar valuation with no revenue.”
Pony Ma rejected Tencent's investment in Airwallex to build WeChat Pay internally
“The founder of Tencent didn't approve. After three months process, RCO pass you know, he just basically is like, because the idea is that this is going to help Tencent to do global, you know, VHAP settlement. And then Pony, the founder was like, why can't we b…”
Sequoia refused to invest in Airwallex until Tencent committed
“The deal was stored and Sequoia was not willing to invest until Tencent kind of make a decision and are basically running out of money.”
Tencent's investment in Airwallex brought in Sequoia and Mastercard
“So we got the investment the day after that. And then obviously you know, Sequoia and then Mastercard also came in with the, with Tencent.”
Early Airwallex VC delayed wiring funds for five months post-term sheet
“The VC that kind of supposed to invest you know, together with Lucy they didn't wire the money, I mean, until like five months later after they signed the term sheet. So they were basically like, show me the demo before they wire the money.”
Jack Zhang bought out an early investor who delayed wiring funds
“I bought out that investor in this round, by the way, I'm very happy about it.”
Airwallex's Tencent deal took 3 years as Tencent built competing tech
“The Tencent deal took me three years. After that point it's just a big corporate, right? It's just take a long time. And it's the same thing from the, WeChat paid department. They were like, why can't we build ourself? So they end up built like essentially wha…”
Mastercard delivered under $1M in volume for Airwallex despite $1B projection
“And Mastercard supposed to give us a billion dollar volume from the Mastercard same product, but we got less than a million dollar.”
Airwallex failed with peer-to-peer and invoicing products before pivoting
“2016, the peer-to-peer algorithm failed. You know, in 2017, I sort of, the invoicing also failed in 2017.”
Shein accounted for roughly 90% of Airwallex's business in 2018
“Well, it's kind of 90% of the business at a time.”
Tencent and Sequoia led Airwallex's $80M Series B at $400M pre-money valuation
“Tencent and Sequoia said, we want to lead another round. So they basically lead a 400 dollar at a four hundred million dollar pre they invest eighty million dollars, so a 404 hundred eighty million dollar post. So they basically, but at that time the business …”
Stripe CFO Will Gaybrick initiated acquisition talks with Airwallex in 2018
“Will Gabrick, the CFO at the time I think now he's CPO, he reached out through Sequoia and he said, just want another, have a conversation to see what you guys are up to.”
Stripe offered nearly $1.2B to acquire Airwallex in 2018
“Essentially it's a complicated deal construct. Essentially it's eight hundred million on the cap table, and three hundred fifty million to me and my co-founders, and I think it's a fifty million dollar I think twenty-five million dollar to the employees, of th…”
Jack Zhang would have made $3B accepting Stripe's acquisition offer
“If I know Stripe gonna get to a hundred billion, I mean, I will probably make, like, at least three billion dollars.”
Airwallex leadership voted 90% against Stripe acquisition offer
“It's surprisingly only one people wanted to sell. Like literally like, 90% of people said, you know, they think we can build a bigger business.”
Jack Zhang commits to building Airwallex for life
“I don't think I wanna, you know, like, Be doing another startup when I'm a 38. I think I'm gonna give it a shot on this one and put all my life into it.”
Patrick Collison told Jack Zhang he will build Stripe for 20-40 years
“Patrick just like said to me that he's going to build Stripe for the next 2030, 40 years.”
Airwallex scaled headcount from 100 to 700 within a year
“We went from like, I think like a hundred something people to like 600 or 700 people like in a year.”
Jack Zhang invested over $50M into unproven products post-Stripe offer
“I basically put most of the money out of the hundred million to build this new product and not investing in the existing product. And that kind of is the biggest bet I made.”
Airwallex took three years to reach product-market fit in the UK
“Yeah, it took me three years to get PMF in the UK.”
Airwallex revenue grew from $2M in 2018 to $20M in 2020
“I think we went, let me just think about again, so we went from like, strap acquisition at that time, we were only two million dollars in 2018, so we went ten million dollars in 2019, so we five times the revenue in 2019, so ten million, then 20 20, we had twe…”
Airwallex raised $400M in 2021, growing valuation to $5.5B
“Yeah, we raised four hundred million dollars in 2021. Like the valuation went from 1.7 to five and a half.”
Airwallex rejected SoftBank's proposal for an $8B valuation round in 2021
“Like, then you raise, like, three rounds, and end of the twenty-twenty-one, SoftBank was talking to me about, you know, leading an eight billion dollar round, and obviously we didn't, you know, entertain that conversation.”
Airwallex would have died without raising $400M in 2021
“I think air wallets will be dead without twenty-twenty-one. Right. We raised four hundred million dollars.”
Airwallex burned close to $200M annually around 2022
“And obviously we raised a flat round in 20 and 22, because at that time we were burning close to two hundred million dollars a year and we weren't really sure like how long we're going to last.”
Airwallex raised its recent round at a $6.2B valuation
“Well, we raised the round at 6.2, like literally when announced last week or this week.”
Airwallex will generate over $400M in gross profit this year
“People, people are looking at gross profit, you know, we doing about 104 hundred fifteen million dollar gross profit. So this year, so essentially it's you know, 13 times of this year gross profit.”
Jack Zhang is taking $70M in personal debt to buy Airwallex secondaries
“I'm actually buying back the Airwaller stock myself, so I actually in the process of taking a debt of seventy million dollars to buy Airwaller secondaries.”
Jack Zhang confirms taking secondary liquidity as Airwallex founder
“I took some secondaries, not a massive amount of money, but, ah, I did.”
Jack Zhang says late-stage founders should take $20M-$30M in secondaries
“I recommend founders take enough secondary so that they can live an account for life, right? They don't need to worry about how do they feed the family? How do they support the kids? How do they, you know, buy a house? You know, I think they should, you know, …”
Jack Zhang dislikes everyday CEO duties but stays to control Airwallex's destiny
“I don't like the everyday of the job of a CEO and I like I able to control the destiny of the company, and I ultimately answer to the outcome of the event, like the outcome of the company, the outcome of the customer the outcome of the employee, right? I wante…”
Jack Zhang personally sourced Airwallex's first 100 employees on LinkedIn
“I hired the first a hundred people in Airworks by myself on LinkedIn.”
Do not over-invest in international expansion without product-market fit
“Don't over invest in international expansion when you don't have part of market fit.”
Airwallex revenue halved in 2020 at the onset of COVID-19
“We lucky that Ian closed around in 2020 when our revenue halved and COVID happened and, you know, stock down 30%”
Startup success depends on curiosity and resilience over bank experience
“None of the people know, none of the people think they know how to build a startup that worked. And ultimately it's not about experience, it's about the competency, right? It's about the curiosity, the determination, about the resilience, and about the belief …”
Founders should prioritize investor leverage over the highest valuation
“You should always prioritize in what gives you the biggest leverage. The leverage on brand, the leverage on hiring that leveraging on commercial opportunities.”
Jack Zhang says only the top five VC firm brands matter
“Only the top five make the difference. So having Sequoia makes a big difference. Huge difference.”
Michael Moritz hosted Jack Zhang at home to urge selling Airwallex
“Michael Morris invited me to his home, tried to convince me to sell the company.”
Jack Zhang predicts Revolut is Airwallex's future competition
“I don't know about Revolut. I mean that's my competition ultimately in the future.”
Pre-PMF investing relies on evaluating personality over data
“I think it just, you know, like before product market fit is really just based on people's personality. I don't know how to make an investment decision based on people's personality.”
Biggest decision errors stem from unaccounted missing knowledge
“Generally people are making decisions based on the knowledge they have, and I think generally that is not the right thing to do because what, the biggest mistake you make is from making a decision based on the knowledge you don't have.”
Airwallex aims to be bigger than Citi or HSBC by 2035
“I hope we have built no, the, one of the largest global payments and banking platform to power more than businesses around the world. I hope we have built a bigger business than city or HSBC because you know, when we succeeded doing that millions of businesses…”
Shorts cut from this episode
▶ How Yuri Milner Invested $100m in Airwallex · 20VC with Harr (@34:14)
▶ The Best Angel Investment In History? · 20VC with Harry Steb (@23:44)
▶ Focus On The Vision · 20VC with Harry Stebbings (@1:25:26)
▶ The $10BN Tencent Meeting That Went Wrong · 20VC with Harry (@44:53)
▶ 0 to $1bn Volume in 9 MONTHS! · 20VC with Harry Stebbings (@0:00)