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.

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 cards, how Amex is selectively stepping deeper into fintech partnerships, and why HELOC-backed credit products reached an unexpected inflection point. He also shares what surprised him most this year, the underwriting innovations reshaping access to credit, and why consumer obsession with rewards has gone fully mainstream. The conversation moves through the history of program management waves, the rise of cloud-native processors, and the real economics behind modern card programs. Finally, Matthew looks ahead to 2026 with predictions around stablecoin settlement, hyper-personalized rewards, and the next big opportunity in gig-worker credit.

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 185 countries.

Sarah breaks down the Genius Act—its real scope, biggest misconceptions, and what it means for payment stablecoins. Sarah also offers a behind-the-scenes look at Circle’s IPO journey, what shifts when a company goes public, and how Circle built Arc, an institutional-grade blockchain platform. Packed with insights on compliance, innovation, and digital finance governance, this episode is a must-listen for fintech operators, lawyers, and anyone shaping the future of financial infrastructure.

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 are falling short. He also explores how AI will reshape compliance roles, the importance of training over tooling, and why regulation might never catch up.

Finally, Jas explains why he’s bullish on crypto and stablecoins—and how traditional banks are quietly following fintechs’ lead. For anyone building, leading, or scaling in fintech compliance, this episode delivers clear-eyed perspective and practical takeaways.