Fintech Chatter: Insights From Fintech Leaders From Employee 2 to 10,002: Alan Costello on the Afterpay Story
Aug 29, 2025
In a captivating discussion, Alan Costello, the second employee at Afterpay, shares his remarkable journey from the startup's humble beginnings to its rise as a global fintech giant. He delves into the challenges of rapid growth and the critical importance of timing and relationships in business success. Alan reflects on the emotional rollercoaster of entrepreneurship, the impact of external factors like the pandemic, and what it truly means to scale a company while maintaining culture. His insights offer a unique window into the dynamic world of fintech.
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Joining Afterpay Over Coffee
- Alan met Nick in a coffee shop and was immediately impressed by his passion and vision.
- He left eBay to join Afterpay as employee number two and brought a willingness to 'take a punt'.
Cash Needs Drove Early Growth Targets
- Afterpay needed to reach ~100 merchants quickly to attract investors and raise cash.
- The business model required upfront cash to fund consumer purchases, creating a cash growth constraint tied to merchant scale.
Balance Hustle With Data Capture
- Capture customer and merchant feedback early even while pushing hard to hit growth targets.
- Balance relentless outreach with basic processes so you can scale learnings efficiently.