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.