CentsChat

This week's CentsChat is a little different. Kitty is joined by Jason and Chris, Steve is conveniently in Hawaii, and we're taking a break from the usual guest format to talk about where the show has been, where it's going, and why payments keeps giving us more material than we could possibly cover.

The conversation looks back at a few themes that keep showing up across CentsChat episodes: payments projects that looked simple on the roadmap and became much bigger operating problems once real money started moving, the difference between integrating payments and actually operating them, and why ownership, monitoring, support, risk, and customer experience tend to collide faster than expected.

We also get into what's happening in payments right now, including recent FTC actions involving Nuvei and Humboldt Merchant Services and the growing focus on merchant screening and monitoring. At the same time, the industry is trying to figure out agentic commerce, AI-driven purchasing, authorization, consent, disputes, and whether consumers are actually ready to let software transact for them. Which is exactly why Jason is still trying to convince Kitty that CentsChat needs to become a daily podcast.

Most importantly, we're talking about what's next. CentsChat is launching full video episodes on YouTube, with help from Cynthia Sassi as we continue building the brand and expanding the way these conversations reach the industry. We also explain what we're looking for from future ISV and software-company guests: not polished product demos, but real operating stories that demonstrate expertise and give other payments professionals something useful to learn from.

Moving from card-not-present into card present sounds simple right up until a physical payment device enters the picture. For ISVs and PayFacs that have only processed online transactions—or that currently rely on a third party for their in-person payments experience—bringing card present in-house can mean taking on a completely different level of technical and operational complexity.

In this episode of Cents Chat, Kitty and Jason sit down with Lori Rainery to unpack what actually changes when a software company decides it wants more control over the card-present experience. Lori brings years of hands-on experience with EMV, POS implementations, payment technology, and ISV integrations from her time at TSYS and First American, giving the conversation a practical perspective on what happens beyond the API.

They get into the parts of card present that are easy to underestimate: EMV certification paths, increased PCI scope, device security, key injection, PIN data, tamper detection, interchange qualification, liability shift, and the downstream cost of getting transaction data wrong. The goal isn’t to turn this into an EMV engineering class, but to make clear just how many moving pieces show up when payments move from the browser to the countertop.

The conversation also digs into one of the less obvious strategic issues: device ownership and portability. Encryption keys, backend relationships, provisioning, and terminal architecture can all affect how easy—or painful—it is to change processors later. Add in the logistics of injecting, provisioning, shipping, installing, supporting, updating, and replacing physical devices, and “just add a terminal” starts looking a lot more like an infrastructure decision.

Lori also shares what she’s doing today with Polaris Crescent, where she’s helping companies use AI and automation to improve the way they operate. So while she may have moved on from the day-to-day world of EMV certifications, her perspective is still highly relevant for ISVs trying to simplify complex workflows, automate the messy parts of their business, and make smarter technology decisions before those decisions become expensive to unwind.

Expanding into the U.S. can look like a simple growth decision on paper. For an ISV, though, the reality is a lot messier. New customer expectations, different payment preferences, more demanding support requirements, and a much more complex payments ecosystem can quickly turn “launch in a new market” into a much bigger product and operations project.

In this episode of Cents Chat, Kitty and Chris are joined by Navneet Rastogi, Founder of Illumine, and AB, Director of Global Revenue and Partnership. Illumine has already built a global footprint serving early-years businesses, and their experience entering the U.S. offers a practical look at what changes when a successful international software company has to adapt its payments strategy for the American market.

The conversation covers how U.S. expansion pushed Illumine to think more deeply about the payments experience inside its platform, from reporting and reconciliation to support, disputes, and partner selection. They also dig into what ISVs should really be evaluating when choosing a U.S. payments partner, including technical maturity, scalability, service levels, documentation, economics, and whether that partner can grow alongside the product rather than becoming the thing that slows it down.

At the center of the discussion is a simple idea: expanding into the U.S. isn't just about finding a company that can process transactions. It's about deciding how much of the payments experience your platform wants to own, how much responsibility comes with that decision, and whether the infrastructure underneath your product is actually ready for where you're trying to go.

An ISV doesn’t have to store card data to have PCI responsibilities. If its software, integrations, access, vendors, or deployment processes can impact the security of cardholder data, it may already be operating as a service provider.

In this episode, Kitty and Chris sit down with Steve Levinson of LHC Advisors to break down the PCI scope trap, the service-provider requirements many ISVs overlook, and why relying on a compliant payment vendor doesn’t make the responsibility disappear. They also discuss Level 1 versus Level 2 validation, QSA-led assessments, vendor-chain attacks, breach exposure, and why strong PCI evidence is quickly becoming a commercial requirement, not just a compliance exercise.

Merchant onboarding used to be relatively straightforward. Today, businesses have more complicated payment flows, harder-to-explain models, evolving compliance requirements, and fraud threats that can make even legitimate merchants look risky on paper.

In this episode of CentsChat, Kitty and Jason sit down with Allen Kopelman of Nationwide Payment Systems to discuss what it takes to board merchants that do not fit neatly into standard underwriting boxes. They explore how clearer documentation, better flow-of-funds explanations, and stronger communication with underwriting partners can turn a confusing application into an understandable business. The conversation also covers synthetic identity fraud, AI-assisted document review, and why complexity does not automatically mean risk—but unexplained complexity usually creates problems.

In this episode of Cents Chat, Kitty and Steve look at the APM conversation from both ends of the spectrum: OpenUSD, stablecoins, and the future of programmable money on one side, and the humble cash drawer on the other. Then Kyle Hatfield from Centsless joins to explain why cash may be the alternative payment method ISVs forgot to build for. With the penny disappearing, merchants are already facing exact-change signs, rounding rules, state-by-state legislation, refund headaches, split-tender complexity, EBT/SNAP considerations, and reconciliation gaps that a simple POS toggle will not fix. Cash may be old, but the software problem around it is brand new.

In this episode of Cents Chat, Kitty leads a conversation with Koard about what happens when the phone becomes the payment terminal. Joined by co-host Jason for the technical deep dive, the discussion breaks down why card-present payments are still harder than they look, why so many ISVs default to card-not-present flows, and how Tap to Pay can help platforms bring in-person acceptance directly into their mobile apps.

Koard’s Behailu explains how their platform helps ISVs, PSPs, and software companies navigate the messy parts: EMV complexity, Apple approval, processor routing, cryptography, merchant onboarding, and the operational reality hiding behind one simple tap.

Because payments are never “just an API.”

In this episode of Cents Chat, Kitty and Jason sit down with Jordan Thaeler, founder of POS+, to talk about one of the biggest tensions in embedded payments: the difference between a preferred payments partner and a payments prison. For years, ISVs have built real revenue streams by integrating payments into their platforms, and when done well, that model can create a better experience for everyone. The trouble starts when “preferred” quietly becomes “mandatory,” pricing drifts out of line, functionality lags, and merchants realize they are not choosing a payments provider so much as being cornered into one.

Jordan breaks down how POS+ is pushing back on that model by giving merchants more payment choice without forcing them to rip out the software they already use to run their business. The conversation gets into merchant frustration, ISV monetization, payment flow workarounds, AI-driven adaptability, and why the smartest platforms should stop treating friction like a moat. The takeaway for ISVs is simple: pick a great default payments partner, make the economics fair, keep the experience strong, and give merchants a reasonable path to alternatives. Most merchants will choose the preferred option if it actually earns the business. But nobody likes being trapped.

In this episode of Cents Chat, Kitty and Chris sit down with Sean Ogden, Co-Founder of GiveTech, to talk about one of the least glamorous but most important parts of payments: merchant onboarding. GiveTech’s mission is to make giving so simple it can happen at a stoplight, but that kind of frictionless donation experience only works if the platform also has strong controls behind the scenes. The team digs into how GiveTech replaced clunky PDFs, DocuSigns, and awkward PII collection with a branded, mobile-first onboarding workflow that feels simple for customers while supporting underwriting, KYC, and fraud prevention.

The conversation also looks at why onboarding has become a bigger responsibility for ISVs and platforms. With card-network monitoring expectations increasing, fintech regulation shifting, and donation platforms becoming attractive targets for fraudsters, getting merchants live is no longer just an administrative step. It is the front door to trust, risk, compliance, and money movement. GiveTech’s story shows how better onboarding can reduce sales friction, protect sensitive information, validate identities, and help legitimate organizations start accepting donations faster without making the platform easier for bad actors to exploit.

Cents Chat is back with a new format, sharper opinions, and a very clear mission: help ISVs, PayFacs, marketplaces, fintech teams, and payments operators make sense of the messy parts of modern payments.

In this relaunch episode, Kitty kicks things off with Jason, Steve, and Chris to explain what the new Cents Chat is all about: real pain points, practical payments strategy, current industry changes, and conversations with ISVs solving actual operational problems.

The team covers why payments can no longer be treated like background plumbing, how API integrations, onboarding flows, merchant risk, compliance obligations, contracts, and interchange fights are becoming platform-level issues, and why future episodes will focus on the problems payments teams are actually trying to solve.

They also preview the first ISV guest conversation, which will dig into onboarding flows and how one company streamlined a process that had become too slow, manual, and messy.

If you build, operate, support, or monetize payments inside software, this is the reset episode. Payments got messy. Good.