Fintech Layer Cake

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...

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 la...

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...

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 fi...

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 agenti...

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 en...

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,...

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, an...

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 ri...

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....

Why are crypto credit cards exploding — and what does the Coinbase x Amex partnership signal about where the card ecosystem is heading next? In this episode, host Reggie Young sits down with Matthew Goldman, founder of Totavi and one of the most respected card experts in fintech, for their annual “State of the Cards Union.” Matthew breaks down why 2025 became a breakout year for crypto-linked card...

In this episode of Fintech Layer Cake, host Reggie Young sits down with Sarah Wilson, General Counsel at Circle, to explore how Circle is shaping the global legal and regulatory frontier for stablecoins and digital assets. She shares her path from big law to fintech, why stablecoins represent the perfect intersection of finance, technology, and regulation, and how Circle manages compliance across...

In this episode of FinTech Layer Cake, host Reggie Young welcomes back Jas Randhawa, Founder and Managing Partner at Strategy Brix, for a candid look at how fintechs are really using AI in compliance.  Drawing insights from a new survey of nearly 100 fintech companies, Jas shares what’s hype versus reality, why most teams are still in the ‘talking’ phase, and where budgets and talent investments a...

In this episode of FinTech Layer Cake, host Reggie Young speaks with Evan Minsberg, Partner at Morrison Foerster, about the nuanced world of money transmission licenses (MTLs). Evan explains what MTLs are, why fintechs need them, and the trade-offs between pursuing a license, partnering with a bank, or using alternative models. He also unpacks the hidden costs, both in dollars and time, behind get...

What does it take to run engineering at the heart of modern fintech? In this episode of Fintech Layer Cake, Imprint CTO Will Larson unpacks lessons from leading engineering teams at Stripe, Carta, Calm, Uber, and more. Will shares how fintech engineering differs from SaaS, the tradeoffs executives face when joining new companies, and why the art of leadership lies in balancing seemingly incompatib...

In this episode of FinTech Layer Cake, Reggie Young sits down with Ariel Blum, Founder of Receive, to unpack the challenges of small business cash flow and why “earned revenue access” could transform how SMBs operate.  Ariel shares his journey from watching his parents struggle with delayed payments, to working at Amex, Green Dot, and Melio, to ultimately founding Receive. They explore the future...

In this episode of Fintech Layer Cake, host Reggie Young sits down with Will Lawrence, Co-Founder and CEO of Greenlite AI, to explore how AI is transforming background checks and employment verification. Will shares how his team is building a platform that makes identity verification faster, smarter, and more reliable, from parsing unstructured data to detecting fraud in real time. Along the way,...

In this episode of Fintech Layer Cake, host Reggie Young sits down with Lee Easton, founder and president of iDENTIFY, to unpack one of fintech’s least understood layers: bank transaction data. Lee breaks down why raw bank data is so unreliable out of the box, and what it actually takes to clean, enrich, and classify it so that it's usable for real-time fraud detection, underwriting, and cust...

In this episode of Fintech Layer Cake, Reggie Young sits down with Max Eber, Co-Founder of Taktile, to explore how modern fintechs are rethinking risk infrastructure. Max shares insights from building a flexible decision engine used by leading lenders and fintechs around the world. They dive into what it really takes to customize underwriting, how Taktile is approaching AI and LLMs in production,...

In this episode of Fintech Layer Cake, host Reggie Young speaks with Maik Wehmeyer, co-founder and CEO of Taktile, an AI-powered risk decisioning platform redefining how fintechs, banks, and even telcos approach mission-critical decisions. Maik shares the multi-year journey from MLOps tooling to a hyper-flexible decisioning platform, and how Taktile now powers over 150 institutions. They discuss t...

In this episode of Fintech Layer Cake, host Reggie Young speaks with Matt Brown, early-stage investor at Matrix Partners and former product leader at Afterpay. Matt dives into the evolving landscape of vertical SaaS, why embedded fintech still has massive untapped potential, and how PE and VC are converging to create new opportunities. He also shares lessons from founding Bonsai, including counter...

In this episode of FinTech Layer Cake, host Reggie Young speaks with Michele Alt, Co-Founder of Klaros Group, about new opportunities in fintech bank charters. They unpack the recent SmartBiz approval, what it signals for the industry, and the realities of the charter process—from regulatory hurdles to risk management. Michele also shares why now might be the best time in years to act—and why ILC...

In this episode of FinTech Layer Cake, host Reggie Young welcomes back Simon Taylor—fintech thought leader, writer of Fintech Brainfood, and Head of Strategy & Content at Sardine. They explore the rapidly emerging world of agentic payments and what Visa’s new tokenization framework means for AI-driven commerce. Simon also unpacks real-world use cases, from “vibe shopping” to automated business...

In this episode of FinTech Layer Cake, Reggie and Ali are joined by Braulio Lam, Senior Director of Engineering at EQ Bank, to unpack the essential ingredients of selecting and integrating a card processor.  With experience across multiple processors and fintech startups, Braulio breaks down what to look for in API documentation, how to assess a processor’s operational and customer support readine...

In this episode of FinTech Layer Cake, host Reggie Young speaks with Cato Pastoll (Co-founder & CEO) and Nik Nampalli (Head of Strategic Projects) of Loop—Canada’s #1 business banking platform. Loop offers multi-currency credit cards, global payment tools, and financial services that save SMBs thousands each year. Cato and Nik break down how Loop evolved into a fintech solution for Canadian bu...