Welcome back to The Paycast Network’s coverage of the Midwest Acquirers Conference (MWAA) 2026 in Chicago, brought to you by Cutter. Here is the breakdown of our four bonus episodes released live from the show floor, featuring Episode 5 with Gretta POS and Episode 6 with Jennifer Ashby.
Episode 3: Clay Shivers on Virality, Networking, and Specialty Contractor Tech
Returning guest Clay Shivers dropped by the booth to share his perspective on attending his very first MWAA compared to massive industry events like ETA.
Key Highlights & Takeaways
- Intimate Community Vibe: Clay noted that while megashows like ETA feature every corporate giant in the room, MWAA feels far more personal and community-driven, making it easier to sit down and build genuine relationships.
- Going Viral: The Paycast team revealed a recent trivia clip featuring Clay exploded on social media, racking up over 60,000 views on Facebook and 70,000 views on Instagram.
- Evolving Beyond Terminals: Clay discussed his vision for evolving from traditional payment processing into a specialized fintech platform for pool services and contractors. The goal is to deliver a SaaS alternative to platforms like Housecall Pro, Jobber, Skimmer, and Pool Brain.
- The Power of Industry Relationships: As Clay put it, “Your network is your net worth.” Even if two processors don’t partner directly, the connections made at regional shows pave the way for referral networks and long-term business growth.
“No one here should be afraid to walk up to someone and introduce themselves. You’re door-knocking all day long anyway, so walking up to someone who can hold a conversation should be second nature.” — Clay Shivers
Episode 4: Neighborhood Payments on AI, Capital Partners, and Big Tech Competition
Local Chicago processors Joe Ayala and Lucio Viezca from Neighborhood Payments joined the booth to break down what it takes to scale an ISO in today’s tech-driven environment.
Key Highlights & Takeaways
- Major Industry Shifts Since 2007: Lucio reflected on his nearly two decades in payments, citing EMV chip migration, cash discounting, and the transition from standalone terminals to deeply integrated POS software as the biggest structural shifts.
- The Challenge of Big Tech: To compete with massive tech players entering merchant acquiring, Neighborhood Payments has actively secured capital partners to fund robust POS systems for their merchants.
- Leveraging Artificial Intelligence: Joe highlighted that a primary focus over his three years in the industry has been integrating AI-driven software for merchant research, automated lead routing, and workflow optimization.
- Mentorship & Recruitment: Success in payments requires blending veteran wisdom with young energy. Neighborhood Payments is actively recruiting sub-agents and training them using hard-learned operational lessons.
Episode 5: Gretta POS on FSMA 204 Mandates & “Selling the Duck”
Ben (Founder & CEO of Journey Business Solutions) and Jordan (Director of Partnerships) stopped by to discuss Gretta Point of Sale, a platform tailored specifically for grocers, butcher shops, meat markets, delis, and bakeries.
Key Highlights & Takeaways
- Payments is More Than Processing: Ben emphasized that modern ISOs cannot win specialty merchants by talking strictly about processing rates. Specialty merchants care about operational pain points: reducing food shrink, yield cut-testing, recipe costing, and vendor cost management.
- The FSMA 204 Regulatory Mandate:
- Under the FDA’s Food Safety Modernization Act (FSMA) Rule 204, every business in the U.S. selling meat, seafood, or produce is required by law to have end-to-end traceability built into their point-of-sale and scale software.
- Gretta POS is one of the few platforms in the U.S. with USDA-certified traceability fully integrated across both POS terminals and deli scales.
- Automated Price Syncing & Digital Tags: To eliminate Monday morning labor overhead, Gretta syncs price changes across POS systems, scales, and digital shelf tags simultaneously from anywhere in the world.
- Sell the Duck! The episode closed with Ben taking on Paycast’s “Sell the Duck” challenge—pitching our giant yellow booth duck as the ultimate trade show icebreaker and conversation starter.
Episode 6: 27 Years of Payments, Legacy Fraud, and Going Independent with Jennifer Ashby
In one of the most story-rich episodes of the series, Jennifer Ashby—a 27-year payments veteran who started her career in 1999—and Carlos walked down memory lane to discuss how merchant acquiring has transformed.
Key Highlights & Takeaways
- Y2K & Manual Imprinters: Jennifer recalled starting in 1999 during the Y2K panic, setting up merchants on Verifone Omni 3200s and handing out manual “knuckle-buster” paper imprinters with voice authorization instructions in case the internet and phone lines collapsed.
- Classic Fraud Scams & Terminal Tricks:
- The Fake Authorization Phone Number: Jennifer recounted a bank teller losing a $5,000 chargeback because a fraudster gave a fake “authorization center” number on the back of a declined card. The teller called the fraudster’s friend, who gave a fake 6-digit approval code over the phone.
- The Last 4 Digits Prompt: Carlos explained a critical safety feature every processor should enable: programming terminals to prompt the cashier for the card’s last four digits. This immediately stops fraudsters using skimmed magnetic stripes cloned onto fake plastic.
- How EMV Chips Stop Magstripe Cloning: Jennifer explained that unlike static magnetic stripes, EMV chips trigger a unique dynamic number sequence with the issuing bank on every transaction.
- The TDD Scam: Jennifer warned against a classic fraud vector where a “buyer” uses a hearing-impaired relay line to order $10,000 in custom goods (e.g., custom cowboy boots) and asks the merchant to key the card and ship the items.
- Leaping into Independence: After 25 years heading an entire department at a single corporate company, Jennifer made the decision to step out on her own to build her own merchant portfolio and achieve true work-life balance.
The MWAA 2026 Chicago Trivia Corner
Here is how our guests fared with this week’s Chicago-themed trivia questions:
Question 1: Which prohibition-era mob boss operated out of Chicago’s Lexington Hotel?
- Guest: Clay Shivers
- Answer: Al Capone. (Clay nailed it instantly!)
Question 2: Did Mrs. O’Leary’s cow actually kick over a lantern to start the Great Chicago Fire of 1871?
- Guests: Joe & Lucio (Neighborhood Payments)
- Answer: No! The story was completely fabricated by newspaper reporter Michael Ahern to create a colorful story angle. The actual cause of the fire remains unknown. (Joe & Lucio correctly guessed it was a myth!)
Question 3: What is the linguistic origin of the word “Chicago”?
- Guest: Jennifer Ashby
- Answer: It originates from the indigenous Miami-Illinois word Shikaakwa, which translates to “wild garlic” or “smelly onion,” referencing the wild ramp plants that grew abundantly along the Chicago River.
From the regulatory impact of FSMA 204 compliance to survival strategies for independent sales agents, MWAA 2026 delivered incredible insights. Stay tuned to The Paycast Network for future show recaps, and head over to our YouTube channel to watch the full video interviews and live streams!