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

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 2025-05-27

01:26:48

Airwallex is the most insane story in startups:

The best angel investment ever: The angel that turned $1M into $1BN. One of the world's best VCs pulled a term sheet and lost $1BN. The company turned down a $1.2BN offer from Stripe. The company scaled to $1BN in transaction volume in 9 months. The company has never not grown 100% in a year.

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 $130B in annual payment volume, $720M in ARR, and a global team of 1,800+ employees. Under his leadership, Airwallex has raised over $1.2BN from investors including Square Peg, Lone Pine, and Tencent.

In Today’s Episode We Discuss:

00:00 – The Best Angel Investment Ever: From $1M to $1BN

06:55 – From Lemon Factory and Petrol Station to Billionaire: The Early Days

15:20 – $5M side hustle while working full-time: how Jack did it

24:45 – Failing Three Times Before Product-Market-Fit

31:00 – The Term Sheet That Got Pulled and Lost Matrix $1BN

34:40 – Why We Rejected Stripe’s $1.2BN Acquisition Offer

49:05 – 0-$1B transaction volume in 9 months: How Shein Saved Airwallex

1:03:40 – We F****** Up Scaling internationally... & Burnt $200M/year

1:08:00 – When COVID hit, they lost 50% of revenue overnight

1:11:45 – Why Jack raised at 6x revenue and is now buying back stock himself

1:15:00 – The truth about secondaries and how much is “enough”

1:18:00 – The hiring mistakes that almost broke the culture

1:20:15 – Why Jack is Taking Out a Line of Debt for $70M

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The Twenty Minute VC (20VC) interviews the world's greatest venture capitalists with prior guests including Sequoia's Doug Leone and Benchmark's Bill Gurley. Once per week, 20VC Host, Harry Stebbings is also joined by one of the great founders of our time with prior founder episodes from Spotify's Daniel Ek, Linkedin's Reid Hoffman, and Snowflake's Frank Slootman.

If you would like to see more of The Twenty Minute VC (20VC), head to www.20vc.com for more information on the podcast, show notes, resources and more.

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