Why OpenAI's Instant Checkout quietly disappeared

Hi y’all,

I hosted a dinner party at my apartment in Paris this weekend and it was magnificent. I also realized last week that AI has given me back about 3–4 hours of my day so that I can focus on the things I really love doing, like writing this newsletter and hosting dinners for my friends. With this extra time back, we’ve got some important projects I want to round out at Praize, but soon maybe I’ll be writing on here more frequently.

Here’s the thing I keep coming back to this week, though. I’m someone who uses AI tools every day. I let Claude research for me, I use AI to write email drafts, I trust it with hours of thought work. But when ChatGPT asks me to hand over my credit card information and make a purchase on my behalf, ehhh I don’t feel all too confident. Not in that I don’t think it would succeed at the task, more that I don’t trust AI with my payment info because I’m not used to shopping like this. And I don’t think I’m unusual.

You already know the AI discovery shift is real — we’ve covered the traffic numbers, the dark revenue problem, and the infrastructure being wired underneath you. Today I want to talk about the fact that technology is ready for AI to shop on your behalf, and consumers are not ready to let it (yet), and this trust gap is going to define the next phase of commerce.

Let’s start with the most telling signal of the quarter.