What’s REALLY going on with those “ads” in ChatGPT | E2220
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What’s REALLY going on with those “ads” in ChatGPT | E2220

E2220 • Dec 8, 2025 • 62 mins

A screenshot showing a “Target Ad” in ChatGPT results went viral… over the weekend, but the OpenAI chatbot has NOT actually opened the advertising floodgates just yet. As ChatGPT staffers were quick to explain on social media, this was actually an invitation for a user to integrate their Target account into ChatGPT, for an easier agentic browsing and shopping experience. But it does prompt Jason and Alex to ask some intriguing questions… Is OpenAI just waiting for Google or someone else to launch AI ads first, and face the inevitable flood of backlash they’ll presumably receive? Is there someone at OpenAI already thinking DEEPLY about how these in-feed ads should work? And what does this mean for their wager on when ChatGPT is going to actually get ads? Is that already decided?

Key Points

  • OpenAI's partnership with Target led to confusion over ads in ChatGPT, highlighting the need for clear communication and strategic planning in ad placements.
  • The competitive landscape for generative AI is rapidly evolving, with OpenAI's market share being challenged by new entrants like Gemini, emphasizing the importance of innovation and differentiation.
  • The Warner Brothers Discovery acquisition saga underscores the complexities and strategic maneuvers in high-stakes corporate mergers, with antitrust considerations and competitive dynamics at play.
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