Sep 10, 2026 5:06 PM

Sezzle CEO Charlie Youakim joins TheStreet Roundtable's 100th episode: what a 44% stake does to his leadership, the Q2 numbers that matter, why the stock fell on raised guidance, Sezzle Cash & Send, building with AI, the BNPL regulatory maze, and profitable growth vs Affirm & Klarna.

0:00 What Sezzle is

1:38 Owning 44%: how a big stake shapes his leadership

4:10 Q2 by the numbers: which one tells the real story

6:02 Guidance raised again, so why did the stock drop?

8:20 Beyond checkout: Sezzle Cash, Send & money movement

10:38 Building products in weeks with AI

14:02 Why the new products were left out of guidance

15:48 Reading consumer strain in the data

18:14 The BNPL regulatory maze & the national bank path

21:15 Profitable growth vs. the competition 

23:53 The one metric to watch

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