20VC: The Most Insane Story in Startups: Airwallex: The Angel That Turned $1M into $1BN | The Fund That Pulled a Term Sheet & Lost $1BN | Rejecting Stripe's $1.2BN Offer | Scaling to $1BN in Revenue & 100% YoY Growth for 8 Years with Jack Zhang

Airwallex's founder refused Stripe's $1.2bn and kept building

Airwallex is a cross-border payments company built by a founder who grew up with little money and kept choosing to build over cashing out. Investors rejected it early and Stripe offered $1.2bn, yet it compounded near 100% a year to about $700m in recurring revenue. The costly mistakes came after funding, when cash went into too many products and markets at once.

Takeaways

• Zhang rejected Stripe's $1.2bn offer. Stripe approached in October 2018 and Patrick Collison flew to Shanghai. The offer was $800m on the cap table and $350m to the founders. Zhang nearly accepted, but about 90% of senior staff voted to keep building.
• Growth has compounded near 100% for eight years. Zhang says Airwallex grew at least 100% a year from 2015 to 2023 and still grows about 90% year on year. Annual recurring revenue reached about $700m in early 2025, and Stebbings projects revenue above $1bn by year end.
• Aggressive expansion after fundraising wasted cash. After DST's $100m round, Zhang put most of the money into new products like card issuing and merchant acquiring instead of the core business. International expansion failed, the UK took three years to reach product-market fit, and burn neared $200m in 2022.
• Early hardship and side businesses built resilience. Zhang arrived in Australia at about 15, lost family financial support at 16 and worked in a restaurant and a lemon factory. Side businesses had earned him over $10m by his late twenties, while he held a full-time job.
• Founders should sell secondary to cover life. Zhang recommends late-stage founders take enough secondary sales to cover their families' needs, around $20m to $30m above a billion-dollar valuation. He is borrowing $70m himself to buy secondary shares.
• Top investors matter, but judging founders is hard. Zhang says only the top five venture firms make a material difference. He doubts his own ability to judge early-stage founders, regrets hiring the first 100 people himself, and calls deciding without real knowledge his biggest mistake.

From idea to first backers

1. A payment by cofounder Max Li was blocked on SWIFT because of a name match, which made Zhang question why cross-border money moves so slowly.
2. The first model was a point-to-point netting system, which he dropped after seeing the volume it needed.
3. Lucy, a former investment banker, invested $1m for 20% at a $5m post-money valuation and wired it before the company was registered.
4. Matrix Partners signed and then withdrew a term sheet for $2m at a $10m post-money valuation.
5. Airtree and Blackbird rejected Airwallex repeatedly, yet later wrote its largest check at a $6.2bn valuation. Square Peg backed a $6m Series A extension.