Tag: ai

Your Conversations With AI Are Now On Sale

OpenAI’s early Ads Manager interface, as posted on Search Engine Roundtable.

Data-driven performance advertising built the modern internet, warts and all. Data has become the most valuable resource in our economy, and the world’s most profitable companies have all organized around enclosing, extracting, processing, refining, and exploiting this new asset class.

Yesterday, OpenAI released its first performance advertising product. Marketers can now purchase “cost per click” advertising on ChatGPT, which means they can compare how money spent on OpenAI measures up to similar platforms like Google, Meta/Instagram, Apple, and Amazon, among many, many others. And if OpenAI’s offerings fail to compete, the company will have no choice but to modify its products to drive better performance.

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First Person Singularities, Epistemic Supply Chains, and Load Bearing Euphemisms: An Interview with Claude.ai

Big dreams.

I woke this morning to news that OpenAI plans on growing its advertising business from zero to more than $100 billion in the next four years. If that sounds utterly bonkers to you, well, you’re not alone.

For OpenAI to accomplish such a monumental task, it would have to leverage the database of intentions in ways that would make the assumptions inherent to today’s internet advertising landscape seem quaintly non-intrusive.

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First Look at OpenAI Ads

Well, they’re here. Just a quick note for now (lots more to say later, but a board meeting in SF means that’ll be later) – OpenAI is rolling out ads to its free and “Go” paid tier. The ads look…harmless enough, just a sponsored link unit with small graphics at the bottom of the chat. Pretty much the exact launch playbook we saw from Google 25 years ago, and Facebook in 2012. A rudimentary prototype of what will become, over the next few years, an increasingly sophisticated monetization platform that, let’s face it, will probably make Instagram look tame.

OpenAI also rolled out some pledges: “We decide which ad to show by matching ads submitted by advertisers with the topic of your conversation, your past chats, and past interactions with ads. For example, if you’re researching recipes, you may see ads for meal kits or grocery delivery. If there are multiple advertisers, we’ll select the one that is most relevant to your chat to show you first….Advertisers do not have access to your chats, chat history, memories, or personal details. Advertisers only receive aggregate information about how their ads perform such as number of views or clicks.”

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Claude Says Non to Ads

Yesterday I wrote a short post on the impact that advertising would have on generative AI, a topic I’ve been thinking and writing about for the past three years. Seems the folks at Anthropic have been thinking about it too, and this morning they gave their thoughts full voice.

“Claude is a space to think,” the company announced in a blog post that promised to never let advertising creep into its core consumer product. “The history of ad-supported products suggests that advertising incentives, once introduced, tend to expand over time as they become integrated into revenue targets and product development, blurring boundaries that were once more clear-cut. We’ve chosen not to introduce these dynamics into Claude.”

This is exactly the point I was making in yesterday’s post – “Advertising Built Generative AI. Now Comes the Remodel.” And while Anthropic’s written post is both thoughtful and measured, the company also launched a four-pack of ads illustrating its point – ads that they will be running during the SuperBowl this weekend. Yep, the SuperBowl.

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Advertising Built Generative AI. Now Comes the Remodel.

Don’t worry, Don’s going to take it from here.

Last night my wife looked up from her phone, disgusted. “All I’m getting is Jeffrey Epstein and Peter Attia!” she said. “Why do they think I’m interested in this?!”

As the family’s resident interpreter of digital entrails, I felt responsible to hazard an answer, but given the prurient nature of the Epstein story, I sensed my thoughts might not be well received. So I backed into it a bit: “Have you clicked on any Epstein-related links recently?” I asked. She had, she rejoined, wary of the implicit judgement hovering over my question. “But that doesn’t mean I want my entire feed to be about it!”

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How Search Drove Generative AI – A Passage from “The Search”

It’s been fun to go back to Berkeley, where I first taught Journalism more than 20 years ago. I’m leading a seminar on how technology impacts journalism, with a particular focus on AI. The class asks students to read a bit of history – it’s hard to understand where we are if we don’t know how we got here. Search is a big part of that history, so I included a chapter of my first book – The Search – as a reading assignment.

As I prepared for class last week, I dug through my archives and unearthed The Search’s original manuscript. In the first chapter, “The Database of Intentions,” I opine on how search might lead to the development of AI that passes the Turing Test. Written 22 years ago, the passage anticipates the rise of generative AI. I start by drawing a distinction between data that is on our personal machines and data held in the cloud by large technology companies like Google. Then I think out loud a bit about where that all data might take us. Even though the writing is two decades old, it prompts some interesting questions about the moment in which we find ourselves.

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AI and Ads: Here We Go!

Google launched as a free public beta in the Fall of 1998. It was a revelation – a 10X improvement on Internet navigation and research. But from its launch forward, Google’s founders were hounded with questions as to how their company planned on actually making money. John Doerr, one of Google’s earliest backers, famously answered that question by citing Google’s extraordinary growth: With all that traffic, he said, we’ll figure it out.

Google’s founders were famously suspicious of advertising – in their white paper explaining Google’s PageRank technology, Larry Page and Sergey Brin argued that advertising-funded search engines would be “inherently biased towards the advertisers and away from the needs of consumers.”

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Predictions 2026: The Full List

Nostradamus, so predictable.

It took me two weeks, 6000 words and nine posts, but I can finally round up my predictions for 2026 in one place. Here’s the complete list in one handy, blissfully shortened post. Thanks for reading, and once (and for good), I wish you a happy, healthy New Year.

#10 – The Feed Declines (Predictions 2026, #10)

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Do You Trust The Conjurer? (Predictions 2026, #1)

Cecco de Caravaggio The Conjurer (The Musician) c. 1600-1620

The modern English verb ‘to conjure’ is derived from the Latin conjurare, meaning ‘band together by an oath, conspire.’ Its roots con (‘with’) and jur (‘legal right or authority, law’) echo with questions central to our present day struggle with technology: Who do we trust to determine authority? Why do we believe in them?

Conjuring also evokes magic, sorcery, and wonder, essential elements of the tech industry mythos. My earliest pieces on the impact of generative AI leaned on the metaphor of magical “genies” doing our bidding in a relationship bound by loyalty and trust. Do those genies work for us, or are they the product of conjurers beyond our control? Do they demand faith, or instill it?

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Battle Lines Are Drawn (Predictions 2026, #2)

The 1960s ain’t got nothing on today.

I concluded my post “Magic and Mayhem” with a bit of a tease about the impact of AI on our society:

There will be lots of magic this year. But there will also be plenty of carnage as previously unbreachable moats start to crumble, not only in business, but also in society at large. For more on that, stay tuned for prediction #2. 

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