Drew Edmond has spent 15 years inside payment operations, first at Square from its scrappy hardware days through IPO, then at Etsy running payments across a marketplace with sellers in 230+ countries. Today he advises merchants at Glenbrook Partners and hosts the Payments on Fire podcast.

In this episode, Reggie Young sits down with Drew to trace how payments actually work from the operator's seat. They cover what changes when a payment goes card not present, the data and testing work most merchants skip, why global expansion demands a plan for every country rather than every region, and whether agentic commerce is real yet. Drew's answer on that last one is more measured than the hype, and more useful.

Fintech Layer Cake is powered by Lithic, financial infrastructure that helps teams build better card and payments products for consumers and businesses.

Chapters:

00:00 – Cold open: why card not present changes everything

00:35 – Meet Drew Edmond: Square, Etsy, and Glenbrook

02:53 – Inside early Square: free readers and a new class of merchant

04:40 – The chain of trust that holds payments together

07:13 – Living in constant negotiation with banks and networks

10:43 – Trusting "the Twitter guy" with your money

11:46 – Square vs. Etsy: the three jobs every platform shares

12:38 – What e-commerce and going global really change

14:51 – Why there's no such thing as a "Europe strategy"

18:53 – The optimization lever most merchants underinvest in

21:44 – How fraud quietly tanks your approval rates

25:32 – Why the optimal amount of fraud isn't zero

26:44 – The hidden complexity of subscription payments

33:13 – The "miasma of payments" and 900-page network rulebooks

35:38 – The CVV era of agentic payments

41:03 – Why discovery is harder than the payment itself

44:57 – Who controls the agent layer wins payment selection

Nothing in this podcast should be construed as legal or financial advice.

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What if millions of Americans had already proven they could handle a mortgage payment — and the system simply refused to count it?

Reggie sits down with Suhas Reddy, Head of Product at Pathward Bank, to unpack what it really means to build product inside the most regulated corners of financial services. Suhas was among the early product leaders at Fannie Mae, driving the Lighthouse Project that later transformed one of the world's largest secondary mortgage institutions into a customer-centric, digital-first product organisation. He now leads product at Pathward as SVP of Product Management across the Nasdaq-listed sponsor bank's B2B products — payments, issuing, lending, acquiring, and commercial finance — developing the products that enable fintechs and brands to reach customers at scale.

The conversation covers the 10-year product build that became an overnight pandemic success story, why Suhas treats risk and compliance as design constraints rather than roadblocks, and the title insurance battle he fought — and lost — years before it became national policy. They get into the philosophy of “Legos, not unicorns” as a framework for building scalable fintech infrastructure, and the human-centric conviction that turned rental payment history into a mortgage underwriting signal — unlocking homeownership for borrowers the system had previously ignored. 

Suhas continues to build infrastructure that expands financial access for underserved communities through Pathward's product platform.

What if every dormant account in your fintech is a ticking compliance clock — and you didn't know the timer started three years ago?

Host Reggie Young sits down with Allen Osgood, CEO and co-founder of Eisen, the company modernising escheatment — the process by which dormant accounts and abandoned funds get transferred to state governments. It's an obscure corner of financial compliance that touches every bank, fintech, brokerage, and increasingly every crypto platform. More than one in seven Americans has money sitting in state hands because of it, with over $80 billion held by state governments at any given time.

Allen and Reggie cover what escheatment actually is and why it matters, the wild story of a retiree who planned his retirement around an Amazon investment — only to find the state of Delaware had liquidated it. They dig into why crypto is about to smash headfirst into dormancy periods nobody planned for, why the 'deal with it later' mindset is a trap that hits three years faster than founders expect, and how proactive compliance can flip a cost centre into a retention engine.

What if the decision that kills your lending business is one you made six months ago — and you just don’t know it yet?

Host Reggie Young sits down with Scott Bass, Managing Director at Ensemblex, the fintech lending and credit consultancy. Scott brings a rare combination of perspectives: he helped build Capital One’s data-driven credit operation before it was a household name and was one of the first two Americans hired to launch Monzo’s US business.

Scott and Reggie cover what Capital One actually got right that most people miss, the lessons Monzo taught about building products that feel nothing like a bank, and the most predictable mistakes fintech founders make when building credit products. They dig into the six-month lag problem in lending, why being “light on the fin in fintech” is a slow-burning liability, and why Scott believes credit cards remain the most complex — and therefore most defensible — financial product a fintech can build. 

The payments industry spent years turning tokenization into a business tool for lock-in. So what does it mean that the same technology might now hold the key to making agentic payments actually work?

Reggie Young sits down with Basis Theory’s Co-founder and CEO, Colin Luce, and CTO, James Armstead — the team behind the programmable token vault platform that has quietly become central to the agentic payments conversation. Colin and James break down what tokenization really is, how it was co-opted as a competitive moat, and why they believe it's the foundational layer that agentic commerce needs to get right.

They get into the reality of agentic payments today — what's hype, what's actually transacting, and why human-in-the-loop is a feature, not a bug. The conversation covers the technical choke points legacy infrastructure wasn't designed to handle, the intent and fraud problem nobody has solved yet, why the industry is over-complicating protocol selection, and what a smarter approach to tokenization could unlock. 

Plus: Colin's bold prediction on the fate of PANs, James on why the early winners will just accept the volume, and the pair on why a misspelled email might be the highest compliment you can give someone in 2026.

If AI is about to transform tax filing, why do 55% of Americans still trust a human to do it for them?

In this episode, host Reggie Young sits down with Gavin Nachbar, founder of Column Tax and Chief Product Officer at Aiwyn, to unpack what it really takes to build in one of fintech’s most complex and overlooked spaces: tax filing.

Gavin shares how Column Tax built the first modern embedded tax engine in the US, what AI is about to change for the 55% who still rely on a human preparer, and why he’s genuinely bullish — not worried — about the road ahead. They also dig into his lessons on entering a regulated space as an outsider, the unique challenges of a seasonal product, and the hard-won takeaways from going through an acquisition.

Will stablecoins replace cards — or is that narrative missing how payments actually work?

In this episode, Reggie Young sits down with Simon Taylor, founder of Fintech Brainfood and Head of Market Development at Tempo, to unpack one of the most debated topics in fintech: agentic commerce. Simon challenges the idea that stablecoins will displace card networks, explaining why cards don’t move money, how stablecoins actually fit into the stack, and why virtual cards may be the first real payment primitive for AI agents. 

The conversation explores machine-native payments, the rise of agents as customers, and Tempo’s Machine Payments Protocol — a new attempt to rebuild payments infrastructure for the internet era. Simon also shares where adoption will come from, why most narratives get the timing wrong, and what the next battleground in fintech will be.

What actually breaks when a fintech expands to the U.S. — product, licensing, hiring, or assumptions?

In this episode, host Reggie Young sits down with Andy Kampf, Partner at Klaros Group and former Klarna US legal lead, to unpack the real framework behind cross-border fintech expansion. Andy breaks down the four pillars every foreign fintech must get right — product, bank partnerships, hiring, and budget — and the hidden pitfalls that derail U.S. launches. From misconceptions about European e-money licenses to choosing the wrong bank partner, Andy shares practical insights drawn from advising global fintechs entering the U.S. The conversation also dives into cultural underwriting differences, lessons from Klarna’s speed-first model, and what Europe’s proposed “28th regime” could mean for startup migration and capital flow. A must-listen for fintech leaders thinking seriously about international expansion.

What happens when you try to build AI-driven fintech products on top of messy, incomplete, or unreliable data?

In this episode of Fintech Layer Cake, host Reggie Young sits down with Kyle Mack, CEO of Middesk, to unpack why data—not AI—is the real bottleneck holding fintech innovation back. Kyle explains how KYB has evolved far beyond a compliance checkbox, why poor data foundations can amplify risk instead of reducing it, and what it actually takes to support real-time, automated decisioning for business onboarding. The conversation dives into agentic workflows, performance constraints, first-party data strategies, and why trust and explainability still matter in a regulated world. Kyle also reframes business verification as revenue infrastructure, not just risk management, and shares why identity should be thought of as a “rail” connecting businesses, banks, and governments. 

In this episode of FinTech Layer Cake, Reggie Young sits down with Gokul Dhingra, Co-Founder and CEO of Narrative, to unpack how AI is reshaping compliance, oversight, and growth in the fintech ecosystem. Narrative is tackling one of the industry’s biggest pain points—the rising cost of compliance and risk management—by turning oversight into a source of efficiency and even competitive advantage.

Gokul shares how banks and fintechs can align around shared objectives, why complaints data is an overlooked goldmine for growth, and how Narrative uses AI to reduce operational thrash while keeping humans in the loop. The conversation digs into the misconceptions about AI “hallucinations,” the subtle ways bias shows up in both humans and algorithms, and why empathy is the ultimate differentiator in building trust with customers and regulators alike.

If you’ve wondered what it takes to scale innovation in a highly regulated environment without sacrificing trust—or how AI can be deployed responsibly in financial services—this episode offers a roadmap from someone building it in real time.