In this episode, Lex speaks with John Caplan — CEO of Payoneer, a public fintech company driving over $85 billion in annual cross-border payment volume. With roots as a prepaid card provider, Payoneer has evolved into a global financial operating platform serving 2 million entrepreneurs across 190 countries. Caplan shares insights from his entrepreneurial journey—from building OpenSky and scaling it to $50 million in revenue before its acquisition by Alibaba, to now leading Payoneer’s transformation into a full-service banking alternative for global SMBs. We explore how Payoneer is addressing the complex financial needs of international businesses, competing in a dynamic payments landscape, and preparing for a future that includes stablecoins, workforce management, and potentially $1 trillion in annual volume.