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Today’s show:

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?

These answers and more are coming your way on today’s action-packed TWiST… PLUS the latest on the Warner Bros Discovery-Netflix deal, PR guru Lulu Cheng Meservey’s new venture fund, and why Jason and Lon are obsessing about Apple TV’s “Pluribius.”

Timestamps:

(01:59) They put Target ads in ChatGPT? Or was it just an integration? Is there a difference?

(5:24) Is someone at OpenAI really thinking deeply about how in-feed ads should work?

(07:36) Is OpenAI just waiting for Google to start running ads to post their own? Jason has suspicions…

(10:01) Why Jason thinks startup people have so much trouble communicating with normies

(10:32) Superhuman - Get AI that works where you work. Unlock your Superhuman potential at https://superhuman.com/PODCAST

(13:22) The insane competition now facing down OpenAI and Sam Altman

(18:40) Why Jason will no longer use data from SaaS companies looking for a marketing win

(19:52) Does this mean ChatGPT TECHNICALLY has ads? Does Alex win the bet?! What does Polymarket think?

(20:36) Squarespace - Use offer code TWIST to save 10% off your first purchase of a website or domain at https://squarespace.com/twist

(25:17) Why Jason is already tired of the Netflix-Paramount-WBD story

(30:06) Enterpret - Enterpret turns feedback noise into Customer Intelligence, so your team knows exactly what to fix and build next. Head to http://Enterpret.com/twist to book a demo and see it in action.

(34:03) President Jason’s new proposal: A 60-day “pre-approval” antitrust window

(47:29) Why Jason’s not interested in news commentary… just the facts.

(51:40) Jason and Lon take a few moments to praise “Pluribus”

(54:45) PR guru Lulu Cheng Meservey is starting a venture firm… here’s why she wants to start a “movement”

(58:05) Why PR people hate but also respect Jason

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

This Week in Startups