I’m Alan Chapell. Over the past 20+ years, I’ve been outside privacy counsel to hundreds of digital media companies. I write a monthly syndicated report called The Chapell Regulatory Insider, and I’m also a regulatory analyst for The Monopoly Report.
The latest Monopoly Report podcast! This week, I welcome privacy legend and former Executive Director of the Electronic Frontier Foundation (EFF) Cindy Cohn. We discuss Cindy’s new book, “Privacy’s Defender,” and cover off on a bunch of relevant issues impacting the ads space.
Evolving the Strategy on the Go…
Back in April 2026, I took a look at OpenAI’s January 2026 ad principles and expressed some skepticism regarding the company’s advertising ambitions. I noted that for OpenAI to get to $2 billion per quarter in ad revenue, it would would need to effectively beat the pace of all the other tech giants – and that the company would ultimately be under tremendous pressure to move away from its stated ad principles sooner rather than later.
What’s more, OpenAI had set itself a target of $100 billion in advertising revenue by 2030 — a figure that comes off as difficult to believe and probably deserves more scrutiny than it is currently receiving.
And then just a few weeks ago, in a Financial Times piece, a senior OpenAI official indicated that “chat is dead” – which, if true, means that a good chunk of OpenAI’s ad revenue would need to come from non-chat surfaces.
Just to recap, we’ve got three huge (potentially contradictory) forces in play:
OpenAI desperately needs ad revenue: This is particularly true given that (a) OpenAI appears to be heading into a token price war with Anthropic that will artificially provide revenue headwinds for a period of time, and (b) OpenAI continues to burn cash at an alarming rate.
Pivot from chat(?): OpenAI appears to be moving away from chat, which seems to be OpenAI’s most obvious ad surface. Such a move would almost certainly have revenue implications and beg the question: What are the most likely alternatives?
Ad principles: While I’ve been under no illusions that OpenAI would remain true to its ad principles over the long term, I did think the company would at least make it into 2027 before revamping and/or openly violating them. And remember: OpenAI is still competing for market share as its users are not locked into the service. That makes it more difficult for OpenAI to act in ways that might be viewed as being against the interests of its customers.
Where Else Might the Ad Dollars Flow?
If OpenAI even partially migrates from a conversational surface to an agentic one, the ad opportunity moves in four directions:
Agentic commerce — influencing which vendor or product your personal agent selects
Partner super-app ecosystem — where OpenAI acts as a “super app” and offers sponsored placement among Canva, Booking.com, and other partner apps
Agent-to-agent signaling — ads tuned to influence other agents, not humans
Residual chat — traditional sponsored answers for users who never leave the chat surface (i.e., it’s hard to believe that OpenAI moves completely away from chat).
In my view (also noted by ads legend BOK), the most lucrative option is probably agentic commerce, as that offers influence over a purchase at the precise moment of intent.
Do OpenAI’s Ad Principles Survive?
Just as a reminder, OpenAI’s advertising principles included statements such as: ads don't influence answers, answers stay "separate and clearly labeled," conversations stay private, users keep control. Those principles were written for chat. It’s not clear how they map to the other surfaces. For example:
Agentic commerce breaks the "answer independence" principle by collapsing the ad into the decision. Can they simply provide a labeled box beneath the answer when the selection itself is what's monetized?
The super-app ecosystem strains a different principle: one of "long-term value." A “sponsored partner” marker survives "separate and clearly labeled," but the moment placement is sold rather than earned, OpenAI is optimizing the ranking for revenue. That's the conflict Google's Quality Score was built to address over 20 years ago. Any move that puts the legitimacy of rankings in question creates potential regulatory issues and could result in OpenAI losing trust.
Agent-to-agent signaling doesn't strain OpenAI’s ad principles so much as it potentially renders them inapplicable. Every promise Simo made addresses a human — "the answers ChatGPT gives you," "your conversations," "you control." There's no human in the loop when one agent influences another.
Residual chat honors the OpenAI ad principles today. If you want to take the position that OpenAI has a cohesive plan, perhaps that’s where OpenAI plants its flag — and clarifies that the ad principles were only designed for the chat surface. The agent surfaces both the option that's best for you and a sponsored alternative and lets you choose. That approach works best inside high-price, brand-driven verticals like travel, but only if you're willing to hand OpenAI your Delta frequent-flyer number. I’m less confident that this approach works for commoditized, low-margin categories.
Building Trust?
OpenAI published a trust framework calibrated to a surface the company has said is all but dead. Recall the Big Tech playbook I've described before: Promise X, walk back X gradually, hope everyone is locked in before they notice. Google took 25 years to travel from "don't be evil" to "do what's best for Google." OpenAI, carrying a reported net loss of $38.5 billion, doesn't have 25 years.
In my view, OpenAI’s ad principles get quietly re-scoped over the remainder of 2026. OpenAI won't announce that ads now influence agent recommendations. It'll simply define agentic commerce as something other than "an answer.” OpenAI appears to be betting that nobody notices this shift.
I think that’s a fairly safe bet.
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And That’s a Wrap.
The Marketecture team is back stateside, with our sanity and luggage (mostly) intact. After enduring a record-breaking heatwave, we’re embracing the luxury of air conditioning while keeping the content captured at Cannes just as hot.
Because advertising’s grande fête is really just the starting line for where the industry is headed next, we’ll be releasing footage captured on and off the Croisette throughout the summer.
Expect candid, thoughtful conversations designed to inspire and inform how you’re thinking about, planning for, and investing across CTV, AI, Commerce Media, Creators, and more as advertising continues to evolve into its future form.
From the French Riviera to your social feeds, we’re bringing you Cannes coverage that goes well beyond the Croisette – and the headlines.
Marketecture Live Early Bird Pricing Ends 7/14!
Blink and you’ll miss it. That’s true of summer but it’s especially true for Marketecture Live: Chicago early bird pricing.
This fall, we’re taking Marketecture Live to the heart of ad land: Chicago. The windy city serves as an industry epicenter for some of the biggest shifts happening across brands, agencies, media, and tech.
If you’ve been wanting to attend Marketecture Live but find NYC to be out of range, meet us in Chicago on September 23. Don’t miss your chance to lock in your seat and the lowest price of the season today.
