A mere six months ago, OpenAI announced what it billed as an unprecedented shift in how consumers buy products online. Instant Checkout would let users research and purchase products entirely within the chatbot - no redirects, no switching apps. Turns out, it's much harder than OpenAI expected.

Only a dozen merchants went live, users are happy to research in ChatGPT but unwilling to buy through it and the operational complexity of e-commerce, pricing accuracy, inventory, tax collection, proved a significant barrier.

OpenAI has now pivoted, moving purchases into third-party apps rather than native chat. Whether that's a strategic evolution or a face-saving retreat depends on your stance.

Amazon's $15bn investment, announced the same week, is hard to ignore. The world's biggest e-commerce company had already blocked ChatGPT from surfacing its products. It's reasonable to assume that kind of money came with some expectations around not building a competing storefront.

For brands that moved early, this pivot is frustrating. Brands that invested in rebuilding product feeds to OpenAI's specific requirements, restructuring data pipelines, and aligning internal teams around a commerce channel that has now fundamentally changed shape.

In AI search, where visibility increasingly depends on how well your product data is structured and surfaced to LLMs, that infrastructure work still has value, but the goalposts have shifted. The brands best placed to navigate this are those treating AI search optimisation as a long-term strategy, not a single-platform bet.

While Dario Amodei has been trading blows with the DoD and OpenAI, Anthropic has been racking up the numbers. Commercially, his company is thriving. Revenue has doubled in two months, growing at nearly twice the rate of rival OpenAI.

The Information published this chart, and the numbers speak for themselves. In January 2025, OpenAI was generating roughly 13 times more revenue than Anthropic.

By March 2026, that gap has narrowed to $25bn vs $19bn - with Anthropic's line going near-vertical from October 2025 onwards. If current trajectories hold, Anthropic could close the gap entirely within six to nine months.

With both companies eyeing IPOs in the next 12-18 months, and neither turning cash flow positive until 2028 (Anthropic) or 2030 (OpenAI), this is a rivalry that will continue for years. Add in a deeply personal and very public feud between their respective CEOs, and it's shaping up to be one of the most watched tech battles in decades.

Claude is pulling in more than a million new sign-ups every day, according to Anthropic's own CPO. In the AI search landscape, that matters, ChatGPT is no longer the default, and users are increasingly splitting their attention across Claude, Gemini and others as the market fragments further.

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