Risk keeps moving even when the rules look settled. We sat down with Kevin Woodward, senior editor at Digital Transactions (https://www.digitaltransactions.net/), to trace where the real pressure is building in payments: Visa’s VAMP and its oversight shift, tokenization that works until it doesn’t, and AI that can help teams underwrite faster without surrendering judgment. The conversation starts with a hard truth—most portfolio fires begin with poor or selective underwriting—and follows that thread into how VAMP could push acquirers toward cleaner books by making constant onboard-offboard cycles a red flag, not business as usual.

Then we get practical. Tokenization has reduced fraud and enabled seamless recurring billing, but when a high-risk merchant is terminated, those vaulted credentials often become immovable. Without a secure and standardized path to token migration, legitimate businesses face revenue cliffs and consumers face needless friction. We explore why that gap exists, how incentives lock data in, and what a fair migration framework could look like for processors, merchants, and cardholders.

Finally, we dig into AI’s real uses: accelerating document checks, classifying business models, scanning web footprints, and predicting attrition so portfolios don’t bleed out quietly. It’s not about replacing experts; it’s about turning noise into signal so risk teams can act early. Along the way, we talk fines versus fairness, communication gaps in new program rollouts, and the small credibility details—like clear, compliant content—that still matter to regulators and partners.

If you care about underwriting discipline, token portability, and AI that actually reduces risk, this one’s for you. Follow and subscribe for more conversations at the edge of payments, and drop a review to tell us where you’re seeing the most friction today.

**Matters discussed are all opinions and do not constitute legal advice.  All events or likeness to real people and events is a coincidence.**

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A payments podcast of Global Legal Law Firm