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AI Business & IndustryStratechery (Ben Thompson)Published: Sep 15, 2026, 19:01 JST

ChatGPT ads working; Walmart yields to Apple Pay

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ChatGPT ads working; Walmart yields to Apple Pay

3 Key Points

  1. What happened

    Stratechery reports ChatGPT ads are working and solve Amazon's biggest problem with chatbots, and that Walmart finally gave in to Apple Pay.

  2. Why it matters

    The finding suggests advertising inside ChatGPT is functioning as a business, and Amazon's chatbot challenge is eased by it, while Walmart's move signals that fighting the status quo is hard.

  3. What to watch

    The outcome hinges on whether these dynamics hold as Amazon's chatbot efforts advance and whether Walmart's Apple Pay acceptance spreads, per Stratechery's framing.

WHO IT HITSRetailers weighing whether to adopt Apple Pay, and companies building or monetizing chatbots, have a concrete data point in Walmart's reversal and ChatGPT's ad performance as described by Stratechery.

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Context & Analysis

Stratechery's update pairs two moves that look unrelated but share a theme: resistance to an established model eventually gives way. On chatbots, the outlet's claim is that ChatGPT ads are working, and that this solves Amazon's biggest problem with chatbots — a notable conclusion given Amazon's own chatbot efforts. On payments, Walmart's long resistance to Apple Pay ends, with Stratechery framing the reversal as the result of the difficulty of fighting the status quo.

Taken together, the two items suggest that the ad-supported chatbot model and broad acceptance of dominant payment methods are being validated by practice, not just theory, according to Stratechery's reading.

FAQ
What does Stratechery say about ChatGPT ads?
Stratechery states that ChatGPT ads are working and that they solve Amazon's biggest problem with chatbots.
What changed at Walmart?
Walmart finally gave in to Apple Pay, according to Stratechery, because fighting the status quo is hard.
Stratechery (Ben Thompson)Read Original Article
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