Kitty: So this week's episode of CentsChat is a little bit different. Today we have Jason and we have Chris, and Steve is in Hawaii.

Jason: Yeah, that really tells you which one of us is making the best life decisions.

Chris: I do think for compliance purposes we should clarify that CentsChat did not send Steve to Hawaii.

Kitty: That is correct. I checked the reports. There is no travel budget.

Jason: I'm still gonna be submitting my expenses though.

Kitty: Absolutely denied. Anyways, we wanted to do something a little different today because there's a lot happening in CentsChat and a lot happening in payments and somehow those two things keep colliding in ways that give us more to talk about every single week. So today we're gonna do a little bit of a look back, a little bit of what's coming next, some payments news, and we're finally gonna talk about the fact that CentsChat is growing up.

Chris: That sounds dangerous.

Kitty: It probably is, but we're gonna do it anyways. The biggest thing coming in is that we're launching a CentsChat YouTube channel and we're gonna start putting out the full video versions of the episode, starting with this one.

Jason: So now people get to see all the things that we hide when all we're doing is editing audio. Wonderful.

Kitty: Yeah, exactly. Audio podcasting was nice because nobody knew what was happening on the other side of the microphone and YouTube has officially ruined that for us.

Chris: And I'm hearing that wardrobe is now a compliance requirement.

Kitty: For you two, absolutely yes. I'm worried.

Jason: Listen, I've been preparing for this moment my entire life. I've got my Bills hat as you can see. It'll be a staple in just about every episode that I'm part of. Go Bills.

Kitty: That somehow creates more concerns, not less. But seriously, one of the reasons we're at this point is Cynthia Sassi. Cynthia has been helping us with a lot of the marketing strategy around CentsChat: how we position it, how we grow it, how the content works together, and how we stop treating every episode like it's just one piece of audio that goes out into the world and disappears.

Jason: So you're saying we finally have a chaperone? We've got some adult supervision for once.

Kitty: Marketing adult supervision. I wanna be very clear that Cynthia is not responsible for anything Jason says on this podcast.

Chris: Great disclaimer, Kitty.

Kitty: Very important disclaimer with Jason. But Cynthia has been a huge help in getting us to think bigger about the brand and what CentsChat can actually become. If you're building a company and you're trying to get smarter about your marketing brand content or growth strategy, go check her out at CynthiaSassi.com. And Cynthia, thank you for helping us grow up a little bit. Now when we started doing more of these conversations, I don't think we fully appreciated how often the best payment story starts with somebody saying, We thought this was gonna be simple.

Jason: That for the most part is the entire payments industry and most of my dating life before I got married.

Kitty: It really is. We just did an episode around moving from card-not-present into card-present. And the premise is almost funny because it starts with we just want to add a terminal as if that's all you have to do.

Jason: Yeah, and just like in marriage, five minutes later you're talking about kids and houses. No, I'm kidding. Five minutes later in payments, you're talking about hardware, EMV certification, encryption, key management, PCI. The box gets pretty big pretty quickly.

Kitty: Which is one of the things I love about these episodes. On the product roadmap, it can look like one little box that says add in-person payments. And in real life, that little box has its own supply chain.

Chris: And its own contracts, responsibilities, support questions, risk allocation, and usually at least one thing that nobody clearly decided they owned until it broke.

Kitty: And that's also becoming a theme around here, define who owns the problem before the problem introduces itself on its own.

Chris: Exactly.

Kitty: Now we've also talked with companies expanding into the US market, trying to figure out partner selection, settlements, refunds, disputes, reporting, onboarding, and all the things that don't necessarily show up in the first API conversation.

Jason: Yeah, and that's usually because the integration is easy to draw on a whiteboard. The operating model, when you flip the switch on, that's when we find out how things actually work.

Kitty: And that's really what I think CentsChat has started to become. We get to take the sentence, we added payments, and ask, okay, but what actually happened after that? That's usually where the useful story actually is. And the funny part is those stories don't stay in one lane. A conversation that starts as a product decision can turn into a support problem, a compliance question, a revenue problem, or a customer trust problem pretty quickly.

Jason: Yeah, that's because payments is an entire ecosystem, not just a button. The API is one part of it, but at the end of the day you're moving real money, there's real risk, and hardware in some cases, dependencies that the customer never sees all have to cooperate and work together at the same time.

Chris: And usually several companies are involved, which means several different definitions of who owns what. That's where it gets interesting, because the customer doesn't care which agreement says whose fault it is. They care that the payment worked, the refund showed up, and somebody answers the phone when it doesn't.

Kitty: And that's probably one of the biggest things I've learned from doing this. From the outside, payments can look like this tiny, narrow specialty. But when you actually get into it and realize it touches basically every part of the customer experience, once money starts moving.

Jason: And that's why stories keep finding us from all aspects of the payment supply chain.

Kitty: And that's apparently why I can't have a normal conversation anymore without someone explaining interchange or merchant monitoring to me.

Jason: Come on, Kitty, our lunch conversations are totally normal.

Kitty: Yes, very much. I'll take another beer. And while we're doing all of that, payments itself is not exactly giving us a quiet week.

Jason: Hey Kitty, this is where I'm gonna make my proposal again.

Chris: He hasn't even made it, Kitty.

Kitty: I don't care. No.

Jason: Listen, I've been saying we should do a daily CentsChat podcast, only three to five minutes every day. Well, just Mondays through Fridays. And all we're gonna do is talk about what happened in the last 24 hours. There's infinite material. Here's why that matters.

Kitty: No.

Jason: Goodbye.

Kitty: No, Jason, I have a life outside of payments and I would like to keep it.

Jason: I can certainly fix that for you.

Kitty: No, this is specifically the part I'm trying to protect. We're good.

Chris: I would like the record to reflect that Kitty has rejected the daily podcast proposal.

Jason: For now, but everything's negotiable.

Kitty: Don't make me call Cynthia on you. But the annoying thing is Jason almost actually has a point because look at just the last couple of weeks. We covered the FTC's action involving Nuvei, where they alleged that the processor opened and maintained accounts for merchants it knew or should have known were engaged in deceptive activity. The settlement includes $4.85 million and requirements around merchant screening and monitoring.

Jason: And the bigger payments lesson here isn't really just about the settlement amount. We all know money grows on trees in payments companies. It's a reminder that underwriting isn't just a one-time gate. You don't get to just approve the merchant, turn monitoring off, congratulate yourself, and head straight to the casino. It's an ongoing exercise.

Chris: That's right, Jason. The responsibility question keeps going after onboarding. What are you monitoring? What are the escalation triggers? Who has to act? What happens when the data starts telling you something you don't want it to tell you?

Jason: You run.

Kitty: And just to be clear, we're not trying to flatten every enforcement case into the same story. The facts matter, the allegations matter, and every case is different. But when two payment processor actions land that close together, it's hard not to notice the operating theme underneath them.

Chris: That's the right way to look at it. Don't jump from an allegation in one case to a universal legal conclusion, but do ask what the enforcement action is telling you about the controls regulators are looking at, the screening, the monitoring, the escalation, and whether warning signs actually lead to action.

Jason: I'm really good at seeing the writing on the walls in the payment space. And this is a trend that I think is going to just continue to evolve. From a system standpoint, that turns into a very practical question. Can you even see the warning signs? Right? Does your technology support you being able to detect things that don't follow the patterns that you expect? Can somebody tell when chargebacks, complaints, transactions, or account changes start moving in the wrong direction? Or are you waiting on card brand fines or regulators to show up at your door to be the ones who tell you there's a problem?

Kitty: And I think that's a very CentsChat way to ruin the phrase. We have monitoring. Okay, what monitoring? Who sees it? What happens after this? And then just a few days later, the FTC announced another action involving Humboldt Merchant Services. That one included $12 million and restrictions around processing for certain higher-risk merchants. And again, the FTC's allegations centered on what the processor knew, what warning signs existed, and what happens after merchants were already in.

Jason: Which is why we've now been able to publish multiple things in a row basically saying, Hey, merchant monitoring matters after approval. And more importantly, if you're a payments company, you can't turn a blind eye in the high-risk space just because it's lucrative.

Kitty: I don't know why we don't get more party invites, Jason.

Chris: I guess it depends on the party, Kitty.

Kitty: A payments

Jason: Hey.

Kitty: compliance party is still not a party, Chris.

Jason: I disagree.

Chris: That's fair.

Jason: I know a lot of people that would love to show up to that party. Great stories would have been told, skeletons would be dug up. It would be fun. Maybe maybe we should host one.

Kitty: Maybe we should. We'll talk about that. But this is what makes payments so strange right now. At the exact same time we're talking about very traditional questions like merchant screening and monitoring, the industry's also trying to figure out what happens when AI agents start shopping and paying on behalf of people.

Jason: Which is super fun.

Kitty: Of course that's the fun part to you.

Jason: You know I love robots, Kitty. Everything today is becoming more and more AI enabled. In fact, I think in ten years we're gonna have a really dumb society because people can't do anything without AI. But that's a personal opinion. I think one of the big challenges with agentic commerce and AI today and the fact that we are pushing that technology so fast is you're dividing the population into two segments. You're dividing the population into people who really trust AI and want to fully get behind it. And then you're dividing the population into the lawyers like Chris, who distrust it. I'm kidding, Chris. I'm just making a generalization because lawyers don't trust anything. But when you boil these numbers down, a recent Visa research study on agentic commerce indicated that only 23 percent of U.S. consumers that were surveyed actually trust generative AI or agentic commerce to handle payment transactions on their behalf.

Kitty: Which means the technology conversation is moving faster than the trust conversation.

Chris: Yeah, that's right, Kitty. And once you let an agent make decisions, you immediately get all the boring questions that turn out not to be so boring. The authorization questions, the consent, the liability, the disputes, disclosures and responsibility.

Jason: And that's where this gets really interesting. We've spent years building payments technologies, checkout flows, mobile applications for a human being being the one to do the purchasing and the button clicking. Now we're talking about letting software decide what to buy, when to buy it, potentially complete the transaction on its own, that leaves a lot of questions.

Kitty: So on Monday we're asking whether a processor monitored a merchant closely enough, and on Tuesday we're asking whether a robot should be allowed to buy my new couch.

Jason: Exactly. Like I said, daily podcast.

Kitty: Still not gonna happen, Jason. Now, there is one thing I do want to say pretty directly, because as CentsChat grows, we want more ISVs and software companies to understand what being featured can actually do for them. And I don't mean come on the podcast and give us a 30-minute product demo. That's not what we want. And honestly, that's usually not very interesting for the audience either.

Jason: We will let you get to brag about the cool things you do, but we found that the best episodes are when a company knows something because they've actually been in the trenches, had to solve something themselves.

Kitty: Exactly. Maybe you moved into embedded payments and discovered the operating model was more complicated than the integration part, or maybe you expanded into a new market, maybe onboarding broke at scale, maybe reconciliation became a mess, maybe card-present changed your product, or your customers force you to rethink how you handle payments entirely.

Chris: You had to decide where your responsibility stopped and your partner's responsibility started and learned that the contract and the real operating model weren't quite the same.

Jason: Those are the stories that make companies an interesting thing. If everybody in your category has a website that says you're seamless, innovative, blah, blah, blah, built for the modern business, that doesn't tell anyone who you actually are.

Kitty: That's where I think being featured on CentsChat can be really valuable. You get to demonstrate expertise instead of just advertising features Because if you're competing in a crowded software category, everybody can say they're easy to use. Everybody can say they have great support and everybody can put embedded payments on the website. What's harder to copy is a point of view that came from actually building and operating the

Jason: Exactly. And if you can explain why you made a particular architecture decision, what broke when you scaled, what you learned from a particular partner transition, or why the obvious implementation turned out to be not the right one, that tells me a lot more about the company than the feature checklist does.

Chris: It also signals maturity. Being able to talk intelligently about the trade-offs doesn't make a company look weak. Usually it does just the opposite. It tells the people you've actually thought through where the risk is and what responsibility comes with the product.

Kitty: And for the people listening who are thinking, well, we don't have some giant traumatic payments disaster to talk about. Good. Please don't create one for us. I don't want that. The story doesn't have to be a crisis. It can be a decision, a lesson, a weird customer requirement, a growth problem, or something you had to redesign because your business changed. We want to hear about it.

Jason: And preferably before the disaster, right? With CentsChat you have a team

Kitty: Yeah.

Jason: of industry experts who've been doing the payments thing for a long time. So if you're facing a challenge that you're not quite sure how to solve, come talk to us. We'd love to share what we know with you as well.

Kitty: Yes, CentsChat doesn't require a fire. We just like hearing what you learned and when you notice the smoke. The podcast gives people the conversation. We can build the editorial story around what you learned. We promote the episode socially, and now we're adding the full video side through YouTube. So one good conversation can become a much bigger piece of brand credibility than just one podcast.

Chris: Yeah, and from my perspective, credibility comes through a lot better when you're willing to talk about the hard part. Nobody believes every implementation was perfect and every decision was obvious.

Jason: And these are the exact kinds of things we would talk about at that awesome compliance party we were talking about earlier, Kitty. imagine the stories that people would share behind closed doors. Those are the stories we wanna have on CentsChat, right? Tell us where the diagram lied, tell us what didn't work the way you expected it to work.

Kitty: Absolutely, but I do expect an open bar.

Jason: If you can get Chris to approve it, I vote yes.

Chris: Let's get the waivers out.

Kitty: But that's the whole idea. If you're an ISV, a marketplace, a vertical SaaS company, a PayFac, or you're building something interesting around payments. We want to hear the real story. What did you learn that somebody else building this should know before they learn it the expensive way? So going forward, that's what I want more of. More founders who are willing to talk about the point where the original plan actually met reality, more operators who can explain what happens behind the scenes, more technical conversations that Jason can translate for me when he gets too excited. More risk and compliance conversations that don't sound like somebody reading a policy manual. More stories from ISVs that are actually building payments into the product and discovering what ownership really means once money starts moving.

Chris: And more conversations where we can separate what the rule says, what the contract says, and what everybody is actually doing. Those aren't always the same thing.

Kitty: I also want to keep bringing in companies from outside the little payments bubble when the story is good. Sometimes the most useful perspective comes from the software company that didn't set out to become a payments expert. They were trying to solve a customer problem and then payments became strategic, whether they wanted it to or not.

Jason: And those are some of my favorite conversations to have, because you get the before and after. At first, payments is a vendor integration, the volume grows, customer expectations change, economics start to matter, and suddenly a software company who never intended to be in payments says, Hey, we can do this better ourselves. And now it's infrastructure.

Chris: And that's usually a point where the agreements, control structure, and operating responsibilities need to catch up with what the business has become.

Kitty: So that's the kind of story we're looking for. Not necessarily the biggest company or the loudest company, the company that has something real to teach.

Jason: Plus more AI, agentic commerce, payments infrastructure, data, all the other things Kitty definitely wants to discuss every single morning on a five-minute daily podcast and over our awesome lunch conversations.

Kitty: I'm gonna mute your microphone and stop inviting you on.

Jason: That seems very anti-growth.

Kitty: Cynthia, if you're listening, this is the problem I'm dealing with. Do you understand?

Jason: Ha ha

Kitty: But really, we're excited about where CentsChat is going. We're going to keep the podcast practical. We're going to keep talking to people who are actually doing the work. We're going to keep pulling apart the stuff in payments that sounds simple until you actually have to operate it that way. And now you'll be able to watch the full episodes on YouTube, which is a very exciting next step for CentsChat, or a terrible mistake that will force all of us to have to improve our lighting

Chris: Or perhaps both.

Jason: I think it's mostly exciting.

Kitty: And if you're building something interesting in payments or software, you've got a story that other operators can actually learn from, we'd love to hear it. The best CentsChat episodes aren't pitches. They're the stories where somebody can say, here's what we thought was gonna happen, here's what actually happened, and here's what we would do differently if we knew everything now.

Jason: Because if there's one thing we've learned doing this, it's that the sentence, this should be simple, is usually the beginning of an episode.

Kitty: And usually the beginning of the problem.

Chris: Which is good for the podcast.

Kitty: Very good for the podcast. Maybe less good for whoever's living through it. Huge thank you again to Cynthia Sassi for helping us think bigger about

Jason: Go Cynthia.

Kitty: helping us think bigger about CentsChat and where we're going next. Go check out CynthiaSassi.com and Steve, we hope Hawaii is terrible.

Jason: We don't really mean that, but come home soon, buddy. We miss ya.

Kitty: We absolutely don't mean that. We're just very jealous.

Chris: Very jealous.

Kitty: That's it for this week's CentsChat. We'll see you next time and apparently soon you'll actually see us too.