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From Employee 2 to 10,002: Alan Costello on the Afterpay Story

Author
Dexter Cousins | Fintech Headhunter and Founder
Published
Fri 29 Aug 2025
Episode Link
None

Kicking off a new career series on Fintech Chatter, Dexter Cousins speaks with Alan Costello, employee number two at Afterpay, about his journey from the early days of the company to its current status as a global leader in the fintech space. 

As Alan reflects on 10 years with the business he shares insights on the challenges of rapid growth, the importance of timing in business, and what it was like to meet founder Nick Molnar and join the rocket ship.

Chapters

00:00 Introduction to Afterpay's Journey
02:59 Alan's Background and Joining Afterpay
06:28 Early Challenges and Growth Strategies
11:28 Recognizing Success and Market Timing
14:50 The Role of Relationships in Growth
17:33 Scaling the Business and Cultural Changes
19:26 The Journey of Afterpay: From Startup to Success
24:42 Navigating Challenges: Regulatory Pressures and Media Narratives
27:48 Sustaining Motivation: The Highs and Lows of Startup Life
30:43 Looking Ahead: Future Aspirations and Lessons Learned









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