Erik Torenberg is joined by a16z General Partner Alex Rampell and Affirm Co-Founder and CEO Max Levchin for a conversation on 25 years of fintech, from the early days of digital payments to the origins of Affirm and the next generation of agentic commerce. Max and Alex revisit what surprised them most about how payments evolved, why the card interface has been so difficult to displace, and why even the smallest corners of payments can become enormous markets. They also trace the early idea maze behind Affirm, from "pay with your identity" and the pajama problem to the realization that installment financing could dramatically increase merchant conversion. The conversation also gets into real versus "fake" 0% financing, what people misunderstand about Affirm today, why negative customer acquisition cost can be such a powerful business model advantage, and why Max is more bullish on agentic payments than on agents choosing what people buy. Timestamps: 00:00 - Intro 01:01 - Meet Max & Alex: 25 Years of Thinking About Fintech 01:33 - What's Surprised Them: Apple Pay, Google Pay & Changing Consumer Behavior 03:36 - Max on the 60-Year-Old Rules Still Running Payments 10:00 - What Idea Should Exist But Doesn't Yet? 12:36 - Did Crypto Feel Like the Realization of a Dream, or Orthogonal? 17:15 - The Origin of Affirm: Solving the Pajama Problem 20:01 - Pay With Your Identity: Social Credit & the General Store Model 27:00 - The Allen & Company 1-800-Flowers Demo 30:57 - The 40 Years in the Desert & Finding Product Market Fit 33:00 - Beautylish, Mattresses & the 30% Conversion Breakthrough 42:15 - What People Miss About Affirm Today: From Satisfying Demand to Creating It 48:58 - The PayPal Mafia: Why So Many Founders Came Out of It 52:44 - Agentic Payments vs Agentic Shopping: The Real Innovation Ahead Resources: Follow Max Levchin on X: https://x.com/mlevchin Follow Alex Rampell on X: https://x.com/arampell Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Show on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Show on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see http://a16z.com/disclosures.