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

This Week in Startups

Jason Calacanis

Technology

4.4 • 1.3K Ratings

🗓️ 9 December 2025

⏱️ 62 minutes

🔗️ Recording | iTunes | RSS

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Summary

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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 http://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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Thank you to our partners:

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Transcript

Click on a timestamp to play from that location

0:00.0	Oh, let me guess. Let me guess. Hit me. I have some concepts here because that ad is for Target.
0:06.7	It's a generic ad. The copy up there was for some sort of technical memory. It went by pretty
0:13.1	quick, but some memory technology, hardware, looked like discussion it was having with ChatGPT.
0:17.5	So it's not a targeted ad. It's an ad for Target. Kind of. Keep going.
0:21.7	Okay. It says shop at Target. So here's what I think happened. I think this person downloaded a
0:26.3	Chrome extension or some other third-party app that was inserting ads covertly or sneakily
0:35.3	and that they wound up conflating that with Open AI doing it.
0:41.1	And that's why it looks so weird.
0:42.3	Now, that wouldn't look weird if you were looking at a, I don't know, the drudge report
0:46.6	and your start target ad, you'd be like, fine.
0:48.3	It doesn't make any sense.
0:49.1	If it was an ad from Open AI, their idea is to look at the memory and what you've searched for over and over and over again, and it would be hyper-targeted.
1:01.6	This weekend startups is brought to you by Interpret. Interpret turns feedback noise into customer intelligence so your team knows exactly what to fix and build next.
1:09.7	Head to Interpret.com forward slash twist to book a demo and see it in action.
1:14.4	Squarespace.
1:15.3	Turn your idea into a beautiful website.
1:17.4	Go to www.
1:18.4	Squarespace.com forward slash twist for a free trial.
1:22.0	When you're ready to launch, use offer code twist to save 10% off your first purchase of a website or domain.
1:27.4	And superhuman. Get AI that works where you work. Unlock your superhuman potential at superhuman.com
1:32.7	forward slash podcast. All right, everybody, welcome back to this week in Starvis. Welcome
1:38.7	back to Twist. I'm Jason Calacanus. He's Alex Wilhelm, and there is a, I guess, some big news out of
	...

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