
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.
NOTABLE DISCUSSION POINTS:
TOPICS
Payoneer, Alibaba, OpenSky, Stripe, Wise, Airwallex, Mercury, NuBank, digital banking, embedded finance, stablecoins, blockchain, regtech, B2B payments, SPAC, supple chain, ecommerce
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TIMESTAMPS
1’06: John’s Career Journey: From OpenSky to Alibaba to Payoneer
6’18: Inside OpenSky: Serving Global Sellers and Financing the Supply Chain
9’54: Finding Traction: Failure, Product Market Fit, and China’s E‑Commerce Leap
13’42: Global Distribution: Universal Ambitions, Local Execution
15’52: Behavior Change Beats Legacy: Why Users Digitize When It Matters
17’21: Payoneer at $85B Volume and $1B Revenue: A Platform for Global SMBs
20’49: From Prepaid Cards to Core Operating Account: Evolving Payoneer’s DNA
25’32: Inside Payoneer’s Architecture: Global Bank Network and Internal Ledger
28’26: Global Growth Corridors: LatAm, APAC, and T