Charlie Youakim - Buy Now, Pay Later, Build Forever

In this episode of Leveraged Storytelling powered by Tunheim, I sit down with Charlie Youakim, co-founder and CEO of Sezzle — the fastest-growing company on the NASDAQ this year and a proud Minnesota fintech built on values as much as velocity. We dive into Sezzle’s core mission: helping the next generation of consumers build strong financial habits through its Buy Now, Pay Later platform — while simultaneously delivering the kind of performance Wall Street expects. Charlie shares how he’s managed to keep the company anchored in purpose while scaling aggressively in a competitive space. We also get into his personal journey — how a previous startup exit didn’t automatically open fundraising doors, and how that experience became the foundation for smarter, sharper decision-making the second time around. We talk about what it takes to raise capital and recruit talent from the Midwest instead of the coasts, and why that’s shaped a unique kind of resilience within the company’s culture. This episode is full of insights on leadership, perseverance, and the long-game mindset that defines Sezzle today — a breakout company many Minnesotans don’t yet realize is thriving right in their own backyard. Hosted by Arick Wierson.