$53M → $3B in 36 Months: The Sezzle Growth Blueprint | Founder Charlie Youakim

Interviews with Leaders in Fintech & Web3

Today’s guest on the show is Charlie Youakim, Co-founder & CEO of Sezzle, the fast-growing Buy Now Pay Later (BNPL) platform.
In this episode, host Matthew Cheung sits down with Charlie to unpack:
✅ Sezzle’s business model
✅ How Sezzle makes money
✅ The shift that led to their rapid profitability & explosive growth
✅ How a billion-dollar company thinks about hiring
✅ Why BNPL is shaping the future of commerce, and what’s coming next
If you’re a founder, CEO, operator, or anyone building in fintech, this conversation is a masterclass.
From understanding how business model innovation can change a company’s trajectory to learning how top fintech leaders hire and scale, this episode is packed with insights.

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บท

1. Trailer (00:00:00)

2. Charlie’s Early Days (00:00:04)

3. Introduction (00:01:14)

4. Lessons from the First Company (00:07:22)

5. What Led to the Idea of Sezzle (00:10:35)

6. How to Win in an Overcrowded Market (00:12:06)

7. Detailed Breakdown of the BNPL Market (00:14:46)

8. How Sezzle Makes Money (00:17:17)

9. Sezzle IPO Story (00:18:48)

10. Impact of COVID on the Stock (00:21:30)

11. Market Crash ($1B to $35M) and the Road to Profitability (00:26:00)

12. Future of the BNPL Market (00:33:34)

13. How Sezzle Helps Young People (00:36:35)

14. Lessons from Building a $3B Company (00:39:45)

15. Hiring Framework (00:41:15)

16. Picking a Winning Sector (00:44:39)

17. Mentors (00:46:18)

18. Business Opportunities (00:47:11)

19. Advice for His 25-Year-Old Self (00:48:56)