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MWAA 2026 Ep 6: 27 Years in Payments, Y2K Fraud Stories & Going Independent

In this episode of our Paycast Network series live from Chicago, 27 year payments industry veteran Jennifer Ashby joins us to share lessons learned from nearly three decades in merchant processing.

Jennifer takes us back to 1999 during the Y2K panic, preparing merchants with manual imprinters and Verifone Omni 3200 terminals. She breaks down wild real world fraud schemes, including a $10,000 cowboy boot scam and a $30,000 scuba gear chargeback. Jennifer also discusses how chip card technology and prompt security features protect merchants today, why she took the leap to go independent after…

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