The Paycast Network

In this episode of The Paycast Network, we sit down with Brian Booth, Founder & CEO of Enroll & Pay, to explore the power of card-linked loyalty in the payments and fintech space.

Discover how turning standard credit card transactions into frictionless loyalty experiences helps local merchants drive repeat business, gather invaluable customer data, and help ISOs drop merchant churn from 25% down to just 1%. Brian shares the journey of Enroll & Pay from early hardware prototypes to embedded POS software, and explains how AI and transaction data are reshaping customer retention.

Key Takeaways:

• Card-Linked Loyalty Explained: How Enroll & Pay turns Visa, Mastercard, and Amex cards into instant loyalty cards right at the payment terminal.

• Evolution of POS Software: Moving from bulky standalone tablets to seamless DejaVoo P-Line hardware integration.

• Why "Retention is the New Revenue": Why ISOs need value-added services beyond price competition to secure long-term merchant relationships.

• Cutting Churn to 1%: How embedded loyalty software creates long-term value for merchants and increases portfolio stability.

• AI & Small Business Data: How everyday SMBs can leverage customer transaction insights to build high-converting automated campaigns.

  Episode Timestamps:

• 00:00 – Welcome to The Paycast Network

• 00:48 – Loyalty Trivia: Green Stamps to Modern Clubcards

• 02:00 – What is Enroll & Pay?

• 03:22 – Hardware Evolution: Tablets to Embedded POS Integration

• 06:00 – Differentiating Your Offering in a Commodity Market

• 07:45 – "Retention is the New Revenue" & Slashing Churn

• 10:15 – Real-World Success Stories Across Unconventional Industries

• 12:00 – Unlocking the Power of AI and Customer Data for SMBs

• 14:50 – How ISOs Can Partner with Enroll & Pay

  Connect & Resources:

• Enroll & Pay: https://enrollandpay.com

• Connect with Brian Booth on LinkedIn: Brian Booth

• ISO Contact: Email Dana Dahms at [email protected]

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In this episode of our Paycast Network series live from Chicago, Paycast favorites Steven Morris (MWAA Board Member) and Jason Isidore stop by the booth for an insider look at MWAA 2026.

Steven shares what goes into planning and executing a major payments trade show, reflecting on the success of the MLS Forum, panel dynamics, and how MWAA's intimate layout creates the ideal environment for high quality networking. Later in the episode, the team discusses the viral growth of the Sell the Duck challenge, leading into an unscripted, high stakes pitch where Steven attempts to sell Jason the exclusive Black Edition Duck for $1,999.99.

In this episode, we cover:

• Behind the scenes of planning MWAA 2026 and conference logistics.

• MLS Forum panel dynamics and key session takeaways.

• Why MWAA's floor layout fosters better networking for first time attendees.

• The viral evolution of the Sell the Duck challenge across the industry.

• The unscripted Black Edition Duck sales pitch between Steven Morris and Jason Isidore.

Sponsored by Cutter

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!

In this episode of our Paycast Network series live from Chicago, Stephen McIver and Johnathon Kiriakos from Loyalty Merchant Rewards (LMR) join us to discuss how ISOs and sales agents can break free from the traditional credit card processing rate race to the bottom.

Stephen and John explain how offering volume based merchant rewards flips the script on standard cash discounting and margin cutting. By earning points directly through their processing volume, merchants can redeem rewards for Disneyland trips, Pebble Beach golf getaways, iPhones, and gift cards, turning merchant processing into a perk instead of a cost. Plus, stick around to hear John take on our famous Sell the Duck sales challenge.

In this episode, we cover:

• Why credit card processing fee cutting has become a race to the bottom.

• How Loyalty Merchant Rewards lets ISOs offer real value through point programs.

• How merchants earn points toward Disneyland trips, golf getaways, and tech.

• Winning cash discount accounts by pitching rewards instead of lower rates.

• The Sell the Duck sales pitch challenge with Johnathon Kyriakos.

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

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

In this episode of our Paycast Network series live from Chicago, we sit down with Ben and Jordan from Greta Point of Sale to discuss how specialized vertical software is replacing standard payment processing in niche markets.

Ben and Jordan break down how Greta POS serves grocery stores, meat markets, delis, and bakeries by going far beyond basic payment acceptance. They explain the upcoming FSMA 204 food traceability regulations, USDA certified scale integration, and how automated digital shelf tags save store owners massive labor costs. Plus, stick around to hear Ben attempt our famous Sell the Duck sales challenge.

In this episode, we cover:

• Why the payments industry is shifting toward deep vertical specialization.

• FSMA 204 regulations and food traceability requirements for food merchants.

• How integrated scales and digital shelf tags automate pricing across physical stores.

• Eliminating labor inefficiencies in retail grocery environments.

• The Sell the Duck sales pitch challenge.

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

In this episode of our Paycast Network series live from Chicago, we sit down with local industry professionals Lucio Viezca and Joe Ayala from Neighborhood Payments.

Lucio reflects on nearly two decades in merchant services, covering the evolution from traditional terminal processing to complex, integrated POS systems. Joe shares what it is like navigating his first three years in payments, leveraging new AI software, and growing a team of sub agents. Together, they discuss the power of cross generational mentorship, securing capital to compete with big tech, and the importance of continuous learning in an ever changing industry.

In this episode, we cover:

• How MWAA has grown and expanded over the last decade in Chicago.

• Major industry shifts including cash discounting, EMV chips, and integrated point of sale software.

• How new agents can leverage AI and veteran mentorship to scale their business.

• Strategies for recruiting sub agents and securing capital to stand out against big tech competition.

• Testing Chicago history knowledge with a famous Great Chicago Fire myth.

Sponsored by Cutter

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!

In this episode of our Paycast Network series live from Chicago, returning guest Clay Shivers stops by the booth to share his experience at MWAA 2026.

Clay breaks down why regional conferences like MWAA offer a more intimate, community focused vibe compared to massive industry shows like ETA. He dives into how he is building specialized platform software for pool service contractors, the value of evolving from payments into vertical fintech, and what it felt like having his previous Paycast trivia clip go viral with over 100,000 views across social media.

In this episode, we cover:

• First time impressions of MWAA 2026 versus larger national trade shows.

• Developing specialized software solutions for pool contractors and field service industries.

• The reaction to Clay's viral trivia moment on social media.

• Why your network is your net worth in the payments industry.

• A quick test of Chicago mob history and prohibition trivia.

Sponsored by Cutter

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!

In this episode of the Paycast Network series live from Chicago, we are joined by MWAA President Rod Katzfey for an inside look at MWAA 2026.

Rod reflects on the record breaking turnout of over 1,600 attendees, the vital role of intentional networking, and why stepping outside your usual circle creates real business value. He also gives us a sneak peek into preparations for next year's 25th anniversary event, including plans to expand keynotes and continue growing partnerships with organizations like Paytech Women and Midwest Fintech.

In this episode, we cover:

• Highlights from day two of MWAA 2026 and managing record breaking attendance.

• The importance of expanding your network beyond familiar contacts at conferences.

• Previewing the upcoming 25th anniversary MWAA conference.

• How to get involved as a volunteer on the MWAA advisory board.

• A friendly Chicago skyscraper trivia challenge between Rod and the hosts.

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 five star rating, and share this episode with fellow payments professionals!

Sponsored by Cutter

The full Paycast Network Livestream of the MLS Forum form MWAA 2026. The MLS Forum unites the merchant services industry’s top leaders, innovators, and game-changers in one can't miss panel discussion.

We are officially kicking off the Paycast Network interview series live from MWAA 2026 in Chicago!

Following our kickoff hype video, our very first full interview features payments industry veteran Jason Isidore. Fresh off co-hosting the live MLS Forum, Jason breaks down the energy of the opening day, why he's passionate about helping newcomers navigate the merchant services landscape, and what it’s like stepping up to a live, unedited stage.

Plus, stay tuned until the end as we put Jason’s local knowledge to the test with a round of Chicago trivia (including the unexpected historical origin of "The Windy City").

In this episode, we cover:

• Recapping the MWAA 2026 MLS Forum and supporting new talent in the industry.

• The difference between pre-recorded content and live conference broadcasting.

• What’s ahead for the rest of the MWAA conference schedule.

• Chicago history & trivia challenge.

Paycast Network is brought to you by Cutter. Find out what a full or partial residual sale could do for your business today: https://cutterfinancial.com/paycastnetwork/

Enjoying the series? Follow the podcast, leave us a 5-star rating, and share this episode with fellow payments professionals!