
Show Notes
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What has to change before AI agents can buy and sell on our behalf? Nate talks with Emily Sands, Head of AI and Data at Stripe, about the trust infrastructure behind agent commerce—and the new problems that appear when software becomes a customer.
They explore token theft and free-trial abuse, why agents challenge sales-led distribution, how Stripe is adapting its tools for agents, and the unsettled economics of AI pricing. The conversation moves from a practical question—would you trust AI to buy your couch?—to the infrastructure needed for those decisions to become routine. Topics include:
Why stealing tokens can matter more than stealing money The tradeoff between protecting free trials and preserving product-led growth What agents need to discover and use developer tools Trust, identity, and payment rails for agent commerce Relentless procurement agents and the pricing questions they create
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For deeper playbooks and analysis: https://natesnewsletter.substack.com/