Who's got two thumbs and an ad running in ChatGPT?

This guy!

It doesn't matter that, by some estimates, OpenAI will miss its ChatGPT ad target by 90%. 

You know why?

Because you're reading a missive from one of ChatGPT's newest advertisers. And it's a game changer.

By game changer, I mean it's a self-service ad platform. Where you enter a headline and description with a limited character count. And include a link to your website. And set bids for how much you'll pay for a click. And a daily budget. And tap into other familiar campaign planning tools.

But other than that, the game has totally changed!

Why?

Because of all the intent data!

It’s data that may or may not be used when targeting the ads. I have no idea how they're being targeted.

In the platform, I could add optional "context hints" defined as, "The conversations, topics, or keywords where your products or services may be relevant; these hints guide matching but aren’t exact-match targeting rules." 

So I guess that's like a keyword broad match?

But still, you know what's the changed game here?

It's AI!

These ads are running in ChatGPT!

I set my bid for a $4 CPC, which it said was going to give me "strong delivery" — the highest mark. Weirdly, it went from "may not deliver" (the lowest score, with an ominous red font) at $2.99 to "strong delivery" (green font!) at $3.00. Nothing I did could trigger the medium rating at yellow.

While I did generate a few dozen clicks at $3.50 a pop with my extremely modest minimum daily budget of $25, it noted "low bid" during my campaign, even though its own bid advice made me sound like I was splurging. There are kinks in the machine.

Do I know exactly what these clicks did for me? Not quite. I rushed to get this campaign out the door and didn't have a great landing page, so I linked to a showcase of my vibe-coding projects. This page isn't designed to sell anything, so this isn't the most robust test of the ad platform.

But, I did get to run my first ads in an LLM. And I could do it myself, with a pittance of an ad budget and no training or onboarding. Someone who’s never run online ads before might be a little confused, but anyone who’s spent even $100 on Google, Meta, or Amazon ads will figure it out instantly.

It wasn't perfectly smooth, as I made some mistakes when signing up. I have an LLC that's different from the main brand I use now, so there was a mismatch when I tried to submit my Employer Identification Number (EIN) for verification. There’s an appeals process, but it was easier to start over with a new account.

OpenAI is setting this up to be a serious contender, and it's not whether it will succeed but to what extent its success will reach the astronomical expectations. 

There's a design principle known as MAYA: "most advanced, yet acceptable." Humans like that sweet spot between familiarity and novelty, reliability and innovation. If we find something too boring, we tune out. If it's too weird, we get the ick.

ChatGPT's ad platform is perfect MAYA. Running ads amidst AI chats at scale covers the "advanced." Making it look like an AdWords clone covers "acceptable." It might be one of the most MAYA ad industry offerings ever. 

Will it matter for OpenAI? It's too soon to tell if the economics work out.

Will it matter for advertisers? It's too soon to tell if the data works out. There are lots of reasons in theory why OpenAI’s data should supercharge ads and make them more effective. But, as my colleague Ari Paparo described in his book Yield, an ad model theory and a $3 OMNY swipe will get you on the subway. 

Should you try it? Absolutely, if you run ads at all, or you've been tempted to do so. Maybe, if you have the right product or service for this format, it'll work well. Your ads will almost definitely work better than mine did if you’re more intentional with what you’re advertising.

When you try it, expect more of the second “A” in MAYA rather than the first one. OpenAI didn't reinvent advertising. And that's one reason it might actually work.

— David Berkowitz, Chief Community Officer, Marketecture Media

Who: Retail CMOs, E-commerce Leads, Performance Marketers, Digital Strategists

What: Arts and crafts retailer Michaels revealed performance data from its new Google Gemini-powered shopping assistant. The conversational tool, which helps customers discover project supplies and follow step-by-step project guides, generates double the conversion rate compared to standard keyword site search.

Why it matters: Generative search interfaces on e-commerce sites are proving they can guide consumer purchase intent much more effectively than basic keyword search boxes.

(Modern Retail)

Who: Brand Strategists, Creative Directors, Agencies, Consumer Brand Managers

What: As generative AI makes content easier to produce, more brands are differentiating through cultural relevance instead of sheer creative volume. Recent examples emphasize music, art, and community participation over AI-generated novelty.

Why it matters: If AI makes average creative cheaper, distinctive brand positioning becomes even more valuable.

(Axios)

Who: Programmatic Buyers, Media Directors, Agency Executives, Performance Marketers

What: Predictive AI firm Dstillery partnered with media agency Canvas Worldwide to deploy autonomous AI agents on live programmatic ad campaigns. The agentic system continuously monitors real-time audience performance, automatically suggesting bid adjustments and audience refinements during campaign flights.

Why it matters: Campaign management is moving from scheduled manual optimization checks to continuous autonomous tuning, forcing media buyers to focus on setting strict guardrails rather than pulling weekly reports.

(The Agile Brand Guide)

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