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

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

27 May 2025

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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  

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