Technology

Stripe’s 2025 annual letter lays out five levels of agentic commerce, and what makes the framework stick is that each level isn’t defined by what the AI starts doing. It’s defined by what the human stops doing. Level 1: Eliminating web forms. You still research and decide. The agent just handles the typing, the checkout fields, the payment details. It’s a clerk, not a buyer. Level 2: Descriptive search. You stop searching for specific products and start describing situations. “I need back-to-school supplies for a third grader in Chicago, nothing too itchy or tight, he likes KPop and tennis.” The system reasons across weather, materials, sizes, taste, reviews, and delivery timelines. ...

The Observation I didn’t build structured data systems because I predicted WebMCP or the agentic web. I built them because “touch it once, make it findable by any system” is just good practice. “Computers do the mundane, humans critically think” is just a sound division of labor. These are principles, not predictions. But those principles, arrived at independently, produced exactly the infrastructure the agentic web needs. A straight line runs from a thought card I wrote in August 2025 to a platform that’s accidentally ready for a protocol Google announced six months later. ...

Last August, I had a conversation with a colleague that stuck with me. We were talking about whether auctions actually find true market value. My argument was simple: how can it be true market value when maybe 5-10% of potential buyers ever see our marketing? We’re calling it market value based on whoever happened to show up. I wrote about it at the time. My answer was to build communities, find your own lake, pursue smarter marketing instead of more marketing. I believed it. I still do. But six months later, I think I was thinking too small. ...

Every time you drive past a license plate reader, walk by a Ring camera, or carry your phone into a room, you’re producing exhaust. Not the kind you choose to share. Not a social media post or an email or a photo you uploaded. This is the byproduct of simply existing in 2026. A friend called it “digital exhaust,” and the metaphor is almost too good. Car exhaust isn’t a decision. It’s a consequence of going somewhere. You don’t think about the fumes trailing behind you. You’re focused on the road ahead. ...