This Week in Fintech's Podcast

An agentic future of commerce is coming faster than merchants think—and PayPal wants to make sure small businesses don’t get left behind. In this live Money20/20 2025 episode of This Week in Fintech, hosts Nik Milanović and Jillian Williams sit down with PayPal’s Michelle Gill, EVP and General Manager of Small Business Financial Services, for a deep dive into how AI agents will transform shopping, loyalty, and merchant discovery.They talk about the next phase shift in commerce: a world where over 40% of shopping journeys may start in chat surfaces, and agents—not humans—do the heavy lifting on search, comparison, and even checkout. Michelle explains why this upends traditional ideas about websites, SEO, and brand, and why “discoverability” and rich product descriptions become the new battleground for merchants of all sizes.The trio dig into big questions shaping this new landscape:- How will small businesses compete when shopping begins in agent interfaces instead of on their storefronts? - What new infrastructure and open protocols are needed so merchants can “integrate once and propagate everywhere” across AI surfaces? - Where does loyalty live when consumers no longer visit your website—but still expect rewards, points, and personalized offers to “just work” in their wallet? - How far are consumers willing to let agents spend on their behalf, and what new trust markers will replace today’s checkout experiences?Michelle also offers a small-business lens on AI: where it can save time first (customer service, email, hiring), where it could power new B2B flows like inventory and reordering, and why AI might both compress margins and lower barriers to becoming a proprietor. She argues that the real opportunity is in turning wasted browsing time into higher-value, more delightful discovery and post-purchase experiences.Stay to the end for a rapid-fire round on Michelle’s recent favorite book, her current AI toolkit, and what she thinks the payments and e-commerce landscape could look like a decade from now. If you care about the future of agentic commerce, small business resilience, or how PayPal is positioning itself for the next era of the internet, this is an episode you won’t want to miss.

We sit down with Nubank co-founder Cristina Junqueira for a candid look at how frustration with fee-first banking led to a product people loved, and how that vision scaled across Brazil. We explore hard-won lessons on leadership, communication, regulation, and why AI plus open finance will reshape money.• leaving an incumbent bank to build customer-first products• forming the founding team and starting with nothing• operating through credit cycles, fraud pressure and regulation• leadership growth, emotional intelligence and storytelling• selling the vision internally and externally• customer impact from fair credit and savings features• Brazil’s policy tailwinds with PIX and open finance• AI as a financial co-pilot and US expansion plans

In this conversation, Nik Milanović discusses the evolving landscape of stablecoins and digital payments with Dan Mottice and Matt Marcus from Modern Treasury. They delve into the recent acquisition of Beam by Modern Treasury, the implications for the payments industry, and the potential of stablecoins to enhance financial operations. The discussion highlights the importance of regulatory clarity, the future of payment systems in the U.S., and the innovative capabilities that stablecoins can bring to money movement.

In today’s episode, Ryan Zauk sits down with Bret Taylor, Co-Founder & CEO of Sierra and Chairman of the Board at OpenAI. Bret’s career is the stuff of valley legend…he is the former Co-CEO of Salesforce, former CTO of Facebook, and has been credited with building products like Google Maps and Facebook's 'Like' button. There may not be anyone closer to AI, spanning the app layer all the way down to its core foundation.In this episode, Bret and Ryan explore several topics including how Sierra has transformed customer service, the agentic era and its consequences for software, why we ‘might’ be in an AI bubble, how Sierra differentiates to win customers like Ramp, Rocket, and Brex, where AI moats will accrue, the 3 AI megatrends he’s leaning into, and much more.Key Takeaways“Every company’s AI agent will be as important as their mobile app or their website.” Bret sees a future where AI agents replace apps and websites as the first point of contact for customers. Agents will handle workflows end to end (fraud reports, mortgage refis, account changes) across all channels, languages, and modalities.CS agents are showing immediate ROI on both the top and bottom line…For example, Rocket’s customers who engage with a Sierra agent are 3x as likely to complete a transaction vs. traditional service. At Ramp, their self-service resolution rate with Sierra’s agents is >90%. Healthcare giant Cigna is replatforming its IVR with Sierra…using AI will help businesses rethink their operating model.Outcome pricing raises the stakes for software, morphing them into true business partners. Outcome pricing will create accountability, transparency, and measurable ROI in an era of vague productivity claims.The Future of AI is 3 things. 1) Multimodal - seamless voice experience. 2) Personalized - knowing your context, preferences, and intent. 3) Proactive - solving a problem before it arises or before the customer knows it has occurred. It’s an AI bubble, but a healthy one. The fundraising hype is alarming, but the underlying transformation is real. Similar to 1999, many firms will fail, but some will become generational winners. If you bought pets.com you lost your money. If you bought Amazon, you made history.

In this episode, Nik Milanović hosts Natalie Wexler from Adyen and Jamey Kennedy from Jackrabbit Technologies to discuss the untapped opportunities in embedded finance, particularly for small and medium-sized businesses. They explore how SaaS platforms can leverage embedded finance to enhance customer experiences, the importance of capital products, and the evolving landscape of funding for small businesses. The conversation also touches on the future of payments, including the potential of AI and stablecoins.