Payments at Square, Etsy, and the Agentic Era, with Drew Edmond, Partner at Glenbrook Partners

Drew Edmond has spent 15 years inside payment operations, first at Square from its scrappy hardware days through IPO, then at Etsy running payments across a marketplace with sellers in 230+ countries. Today he advises merchants at Glenbrook Partners and hosts the Payments on Fire podcast.In this episode, Reggie Young sits down with Drew to trace how payments actually work from the operator's seat. They cover what changes when a payment goes card not present, the data and testing work most merchants skip, why global expansion demands a plan for every country rather than every region, and whether agentic commerce is real yet. Drew's answer on that last one is more measured than the hype, and more useful.Fintech Layer Cake is powered by Lithic, financial infrastructure that helps teams build better card and payments products for consumers and businesses.Chapters:00:00 – Cold open: why card not present changes everything00:35 – Meet Drew Edmond: Square, Etsy, and Glenbrook02:53 – Inside early Square: free readers and a new class of merchant04:40 – The chain of trust that holds payments together07:13 – Living in constant negotiation with banks and networks10:43 – Trusting "the Twitter guy" with your money11:46 – Square vs. Etsy: the three jobs every platform shares12:38 – What e-commerce and going global really change14:51 – Why there's no such thing as a "Europe strategy"18:53 – The optimization lever most merchants underinvest in21:44 – How fraud quietly tanks your approval rates25:32 – Why the optimal amount of fraud isn't zero26:44 – The hidden complexity of subscription payments33:13 – The "miasma of payments" and 900-page network rulebooks35:38 – The CVV era of agentic payments41:03 – Why discovery is harder than the payment itself44:57 – Who controls the agent layer wins payment selectionNothing in this podcast should be construed as legal or financial advice.Subscribe for new episodes every other Wednesday. If you enjoy the show, leave a review on Apple Podcasts or Spotify to help more people in fintech find it.