Navigating Pivotal Decisions

Airwallex is the most insane story in startups:

1. The best angel investment ever: The angel that turned $1M into $1BN.
2. One of the world's best VCs pulled a term sheet and lost $1BN. 
3. The company turned down a $1.2BN offer from Stripe. 
4. The company scaled to $1BN in transaction volume in 9 months. 
5. 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