Charlie Youakim is the co-founder and CEO of Sezzle (SEZL), a buy-now-pay-later company now valued at over $3 billion. He previously co-founded Passport, a mobile payments business for parking, and built Sezzle into one of the largest BNPL providers in the U.S. despite raising roughly $120 million in total, a fraction of the capital raised by competitors like Klarna and Afterpay. Sezzle first listed on the ASX in July 2019 and direct-listed on the Nasdaq in August 2023; its market cap bottomed at roughly $35 million during that stretch and has grown to over $3 billion in under three years, roughly an 85x return.

This discussion took place live on May 13th, 2026, on the MicroCapClub Community. Join MicroCapClub and unlock the ability to listen and participate live in these discussions - https://microcapclub.com/#join

In this episode, Charlie discusses why he started over after his first exit, how Sezzle pivoted to profitability after a failed merger with Zip, his data-driven hiring approach built around IQ and GPA, and how the company operates as a fully remote, internationally distributed team. He also walks through Sezzle's push beyond BNPL into checking, savings, and cash management products, and how AI is reshaping the way the business runs internally.

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Chapters

00:00 The Journey of a Serial Entrepreneur

04:21 Understanding Sezzle's Business Model

07:02 The Evolution of Sezzle and Market Competition

09:55 Navigating Profitability and Growth Challenges

12:59 Hiring Standards and Company Culture

15:54 The Impact of Location on Business Success

18:54 Remote Work and Its Advantages

21:50 Learning from Industry Peers

41:01 Building Relationships in Business

43:59 The Value of Common Sense

45:36 Defining Success and Winning

47:03 Innovative Cash Management Solutions

51:05 Misunderstandings About Sezzle

53:11 Scaling with Focus and Founder Mentality

58:44 Leveraging AI for Efficiency

01:02:04 Optimism About AI and Job Markets

01:10:17 Competitive Advantages in Fintech

01:12:00 Philosophy on Stock Ownership

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