why aren't all 60 resolved? a statement only gets an assessment when the public
record can support or contradict it. opinions and what-ifs never can, and 2 checkable
ones are still open, waiting for their date. predictions held up or didn't;
assertions are supported or contradicted. on every card:
▮▮▮▮▮ certainty ·
▮▮▮▮▮ debate potential. speakers are clickable
Prediction Held up
O'Driscoll: US fintechs will use anti-China messaging against foreign rivals
“Competitors are going to be the people who use it first. Because if I was an all-American fintech company, I'd have my all-American flag out there and say, these guys are a bunch of commies. They have commies looking at your data. We're, you know, our stuff is…”
Disclosure
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…”
Jack Zhang May 26, 2025 ▶ 30:51 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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 May 26, 2025 ▶ 1:23:20 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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…”
Jack Zhang May 26, 2025 ▶ 44:02 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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 May 26, 2025 ▶ 1:30:45 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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…”
Jack Zhang May 26, 2025 ▶ 48:56 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Prediction Open · timeframe May 2035
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…”
Jack Zhang May 26, 2025 ▶ 1:34:10 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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.”
Jack Zhang May 26, 2025 ▶ 1:19:21 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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.”
Jack Zhang May 26, 2025 ▶ 49:23 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Insight
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 May 26, 2025 ▶ 9:09 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Supported
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 May 26, 2025 ▶ 1:00:51 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Supported
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 …”
Jack Zhang May 26, 2025 ▶ 32:37 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Open · timeframe Sep 2027
Stebbings: Tech companies like Klarna build their own customer support AI
“And then the worst thing about this market is that for any sophisticated buyer, an Airwallex, a Klarna, a Navan, a technology-facing company, everyone has built their own.”
Opinion
Stebbings: Willing to pay triple valuation for top founders
“Actually, there are founders like Alan Chang at Fuse or Jack at Airwallis. You could treble the price and I'd still pay it today.”
Opinion
Lemkin: Airwallex at $8B valuation is a market dislocation opportunity
“I think ADEX ARR is a good deal. You trust great founders to figure it out. I think it's a fine deal. It sounds like a dislocation in the market, and you could do worse than invest in a dislocation in the market.”
Assertion Not checkable as stated
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”
Jack Zhang May 26, 2025 ▶ 32:22 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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.”
Jack Zhang May 26, 2025 ▶ 0:00 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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 May 26, 2025 ▶ 1:22:03 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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 May 26, 2025 ▶ 47:52 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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.”
Jack Zhang May 26, 2025 ▶ 1:20:08 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
What-if
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.”
Jack Zhang May 26, 2025 ▶ 1:19:52 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Supported
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 May 26, 2025 ▶ 1:04:38 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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.”
Jack Zhang May 26, 2025 ▶ 42:50 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Prediction Held up
Airwallex full-year revenue will exceed $1B
“More than a billion.”
Jack Zhang May 26, 2025 ▶ 1:21:31 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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.”
Jack Zhang May 26, 2025 ▶ 1:08:36 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Insight
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 May 26, 2025 ▶ 1:29:19 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Supported
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 May 26, 2025 ▶ 0:22 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Insight
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 …”
Jack Zhang May 26, 2025 ▶ 1:28:35 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Opinion
Stebbings: Deep integrations and physical coordination protect companies from AI disruption
“There's two areas where I find value and security. It's one where there's deep integrations and partnerships, which are difficult, and they'll never do. We're an investor in Airwallex. We've discussed before. They have hundreds of banking relationships and par…”
Assertion Not publicly verifiable
Airwallex sustained over 100% annual growth from 2015 to 2023
“So we basically never grow below a hundred percent from 2015 to 2023.”
Jack Zhang May 26, 2025 ▶ 0:17 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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.”
Jack Zhang May 26, 2025 ▶ 48:30 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Insight
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.”
Jack Zhang May 26, 2025 ▶ 22:53 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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.”
Jack Zhang May 26, 2025 ▶ 25:40 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
Shein accounted for roughly 90% of Airwallex's business in 2018
“Well, it's kind of 90% of the business at a time.”
Jack Zhang May 26, 2025 ▶ 54:01 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Prediction Not checkable as stated
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.”
Jack Zhang May 26, 2025 ▶ 1:32:05 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Not checkable as stated
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.”
Jack Zhang May 26, 2025 ▶ 44:46 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Opinion
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 May 26, 2025 ▶ 1:25:57 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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…”
Jack Zhang May 26, 2025 ▶ 26:32 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Supported
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.”
Jack Zhang May 26, 2025 ▶ 1:19:10 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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%”
Jack Zhang May 26, 2025 ▶ 1:27:36 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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 May 26, 2025 ▶ 1:24:22 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
Every Australian VC rejected Airwallex early on
“Because all the VCs kind of rejected me in Australia. It was only three VC.”
Jack Zhang May 26, 2025 ▶ 30:12 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Disclosure
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.”
Jack Zhang May 26, 2025 ▶ 1:21:40 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Partly supported
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 May 26, 2025 ▶ 1:07:28 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Supported
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.”
Jack Zhang May 26, 2025 ▶ 56:09 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Supported
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.”
Jack Zhang May 26, 2025 ▶ 52:08 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Supported
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 …”
Jack Zhang May 26, 2025 ▶ 54:29 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings
Assertion Supported
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.”
Jack Zhang May 26, 2025 ▶ 47:01 Airwallex CEO & Co-Founder, Jack Zhang: The Angel That Turned $1M into $1BN · 20VC with Harry Stebbings