06-reference

stratechery openai amazon ads walmart apple pay

2026-09-15·reference·source: Stratechery·by Ben Thompson
stratecheryopenaiadvertisingamazonchatgpt-adsagentic-commercewalmartapple-pay

"OpenAI Ads, Amazon Ads in ChatGPT, Walmart to Accept Apple Pay" — Ben Thompson

Why this is in the vault

First hard evidence that ChatGPT is a scaling, non-hypothetical ad channel — OpenAI's ad business hit $1B annualized run-rate and Amazon just became a live advertiser inside it — which is a direct input to whether/when RDCO's own paid-ads channel mix should expand beyond its current Meta/Google/LinkedIn/X footprint.

Mapping against Ray Data Co

The concrete anchor: /paid-ads (~/.claude/skills/paid-ads/SKILL.md) currently scopes Squarely to Meta + Google Shopping + Pinterest and MAC/Sanity Check to LinkedIn + X + Google Search — ChatGPT is not on either channel list, and as of the skill's last update (2026-04-25) no RDCO paid campaigns are live anywhere yet. This issue is the strongest signal yet that the gap is closing: OpenAI's ad business went from a February launch to $1B ARR and 40+ country self-serve rollout in ~200 days, and Amazon — which has aggressively blocked AI platforms from its storefront via robots.txt — chose to become a ChatGPT advertiser rather than keep fighting the channel. Thompson's read is that Amazon flipped the problem: instead of accepting OpenAI's affiliate-marketing pitch, Amazon runs its own campaigns and lets ChatGPT control placement, preserving Amazon's logistics-trust moat while buying back the ad inventory chatbot-mediated shopping was cutting it out of. That's the same agentic-commerce shape as the merchant-owned-checkout thesis in [[2026-05-03-sytaylor-ucp-merchant-owned-agentic-checkout]] — merchants retaining control of the transaction while ceding placement/discovery to the agent layer. For Squarely specifically, which already runs its own Amazon storefront funnel ([[2026-05-13-website-amazon-funnel-audit]]), this is a preview of a channel that may eventually be worth testing directly, not just via Amazon's own presence. It also reinforces RDCO's L5 read ([[project_l5_north_star_strategic_direction]]) that agent surfaces are becoming real monetization and distribution layers, not just capability demos — OpenAI's 1B weekly active users converting into ad inventory is the B2C mirror of the agent-commerce infrastructure RDCO is building on the B2B/internal side (Channels agent, approval-gated purchases).

The Walmart/Apple Pay item is weaker and mostly illustrative: Thompson's point is that Walmart could resist Apple Pay (existing demand, easy to preserve status quo by already accepting cards) but Amazon can't resist ChatGPT the same way (new demand, and that demand's fallback habit is just searching Amazon.com directly) — a useful "which status quo actually has leverage" heuristic, but not a distinct RDCO data point on its own.

Issue contents

OpenAI Ads

OpenAI's ChatGPT ad business (launched to U.S. Go/free-tier users in February) hit $1B annualized revenue run-rate around 200 days in, per CNBC, and is now self-serve in 40+ countries including a fresh India/EMEA/North Africa rollout. Thompson notes Anthropic made OpenAI's ad launch the target of its first Super Bowl ad, and that he himself had argued OpenAI should have launched ads years earlier. His verdict: ads are a genuine three-way win (free/cheaper product for users, revenue growth without price hikes for the platform, high-intent placement for advertisers) at OpenAI's 1B-weekly-active-user scale.

Amazon Ads in ChatGPT

Amazon announced select U.S. brands can now run ads inside ChatGPT, per CNBC — Amazon was already the top retail advertiser on the platform (Apr–Aug, Sensor Tower data) before this formal partnership. Amazon manages campaigns/targeting; OpenAI's system controls ad placement — a thinner integration than Amazon's Meta ad-targeting link. Thompson frames this as Amazon solving its own chatbot problem: it has aggressively blocked ChatGPT/Claude/Gemini from indexing its storefront (robots.txt) while investing in its own AI shopping tools, and CEO Andy Jassy signaled this move on the Q1 earnings call. By selling advertisers "the right to be the Amazon link in ChatGPT results" instead of letting OpenAI do affiliate marketing on Amazon's inventory, Amazon keeps control of the transaction and its logistics-driven trust advantage.

Walmart to Accept Apple Pay

Walmart and Sam's Club are finally rolling out tap-to-pay (including Apple Pay) starting late August, ending a decade-plus resistance that included Walmart's push for the ill-fated CurrentC consortium and its own Walmart Pay. Thompson's framing: Walmart fought existing card-based demand and lost; the CurrentC/Walmart Pay saga is the negative case study against his original pro-Apple-Pay stance from 2014.

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