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.

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 getting licensed, and how fintechs can think strategically about when it makes sense to pursue one.

From agent-of-payee exemptions to the risks of operating without proper licenses, Evan offers a practical primer for founders navigating regulatory quicksand. He also shares trends in state-level adoption of the Money Transmission Modernization Act (MTMA), rising anti-money laundering scrutiny, and myths about “FBO” and “BOBA” accounts. Whether you’re building a payments product, exploring embedded finance, or just trying to future-proof your business, this conversation is packed with insights you won’t want to miss.

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 incompatible frameworks, moving fast while preserving reliability, innovating while managing legacy systems.

He also dives into the hype and reality of large language models (LLMs). Will explains why today’s “AI engineers” may simply be tomorrow’s product engineers, why prompt-crafting is more artisanal than strategic, and how agentic tools could redefine workflows. From the shifting expectations of tech executives over three decades to what really drives innovation inside scaling companies, this conversation is equal parts practical and forward-looking. For anyone navigating fintech engineering or curious about the future of AI in product development, Will offers a grounded perspective on what matters most.

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 of embedded finance, fintech’s shift from “hot or not” to “essential,” and how solving cash flow timing mismatches could unlock massive opportunities for the 33 million small businesses in the U.S. and beyond.

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, they discuss the challenges of scaling AI in high-stakes industries, the balance between automation and human oversight, and what it takes to turn raw data into trusted decisions.

Whether you’re in fintech, HR tech, or just curious about the future of verification, this conversation delivers practical insights you can use today.

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 customer engagement.

From manual tagging nightmares to building classification models across 1.2 billion transactions, this conversation is a practical deep-dive into what “decision-ready” data really means.