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

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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Chapters

• 0:00 Trailer
• 0:04 Charlie’s Early Days
• 1:14 Introduction
• 7:22 Lessons from the First Company
• 10:35 What Led to the Idea of Sezzle
• 12:06 How to Win in an Overcrowded Market
• 14:46 Detailed Breakdown of the BNPL Market
• 17:17 How Sezzle Makes Money
• 18:48 Sezzle IPO Story
• 21:30 Impact of COVID on the Stock
• 26:00 Market Crash ($1B to $35M) and the Road to Profitability
• 33:34 Future of the BNPL Market
• 36:35 How Sezzle Helps Young People
• 39:45 Lessons from Building a $3B Company
• 41:15 Hiring Framework
• 44:39 Picking a Winning Sector
• 46:18 Mentors
• 47:11 Business Opportunities
• 48:56 Advice for His 25-Year-Old Self