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 25 years in corporate, and finishes with a Chicago origin trivia challenge. In this episode, we cover: Preparing merchants for Y2K in 1999 with manual imprinters and early terminals. Uncovering wild fraud schemes and chargeback horror stories. How EMV chips and last four digit security prompts prevent modern card fraud. Leaving a 25 year corporate role to build an independent merchant portfolio. Discovering the Native American origin of the word Chicago. Curious about the true value of your payment processing residual portfolio? Whether you are looking to retire, reinvest in your business, or secure liquidity, Cutter purchases residual portfolios from agents and ISOs with no obligations, no new business requirements, and no lock in contracts. Find out what a full or partial residual sale could do for your business today: https://cutterfinancial.com/paycastnetwork/ If you are enjoying our MWAA coverage, follow the show on Spotify, leave us a rating, and share this episode with fellow payments professionals! Sponsored by Cutter