Category: Top Posts

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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How Long Will Your Claw Be Open?

Try me, then you’ll buy me.

It’s “phase two” of the AI boom, and the claws are out.

Back at the tail end of 2024, I wrote these words: “2025 will not be the year AI agents take off.  As the bloom came off the Generative AI rose in 2024, everyone started talking about AI agents as the Next Big Thing. Google, Apple, OpenAI, Microsoft, Meta, Amazon – all of them (and about a million startups) are trying to build user agents for both enterprise and consumer use cases. I’m a huge fan of the concept, but for now, it remains just that. Reasoning agents that book your travel, negotiate your insurance bills, or manage your calendar simply will not work if they are beholden to the same business models currently driving Big Tech.”

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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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The Feed Declines (Predictions 2026, #10)

Evolve, or die?

At the dawn of digital, when cell phones were new and culture dominated by cable television, most of my friends and family considered me an ‘early adopter.’ I was usually the first of my crew to engage with any new digital device or service – the Mac, email, the web, search, wifi, even nascent social sites like Friendster, Orkut, and LinkedIn. I was one of the very first people on Instagram, back when it was just a photo site. I was the guy friends and family called when they had a computer problem, and later, when their smart phone acted up. It wasn’t that I was particularly adept at coding or solving IT problems. I was just the guy who everyone knew had spent the most time in the digital world. You know, the Wired guy.

For nearly three decades, I stayed current with all things digital. But about ten years ago, I started pulling back. At first it was more of a vibe – I didn’t like how the digital world was starting to feel. Insistent, needy, demanding. I’d worked for most of my life inside digital spaces, but before the web went world wide, digital was more of a solo act. You, the “user,” were in charge. You decided which applications to pay attention to, which documents to read or write, which sites to visit. That was starting to change, and it didn’t feel right.

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Get Wired: The Launch (1992-93)

The launch issue of Wired.

(continuation of a previous post)

If you ever have a hit on your hands, my advice is to take notes. Living in the whirlwind of blinding success is a little like experiencing your own wedding – everyone tells you to enjoy it, to remember every detail. But decades later, all you can recall is leaving the reception, relieved that everyone seemed to have a good time. 

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How Google Can Win the Future

[Second in a series, first post here]

This past week, Wall Street caught up with the rest of us and realized that Google has lost its monopoly grip on search. The trigger wasn’t Google losing an anti-trust case – that happened last summer. Nor was it the first ten days of Google’s ongoing search remedies trial. Instead, it was a statement just two days ago by an Apple executive, Eddie Cue, which led to an almost instantaneous panic amongst investors.

Cue told the court that consumers’ preference for using AI agents had led to a decline in search traffic inside Apple’s Safari browser (Google pays Apple more than $20 billion a year to secure that traffic – a major focal point of the government’s case).

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Predictions 2025: Tech Takes the Power Position

Look, I’m not much of an AI image-generation prompt writer.

This isn’t going to be a normal year.

2025 will be strange, frenetic, and full of surprises, particularly for those of us who watch tech closely. We’re not accustomed to the tech industry having this much raw power. The finance industry? Sure. For decades, we watched leaders from Goldman rotate through every administration’s cabinet and economic team, and we got used to it. But this year, for the first time ever, Big Tech has leap-frogged finance in the pantheon of political influence. And while the finance bros have a reliable and predictable ideology – capital is king – the subset of Big Tech bros who’ve bought their way into the Oval are evangelists for an untested and downright strange brand of magical thinking best summed up as “techno optimism.” The sophomoric claptrap underpinning Andreessen and Musk’s approach to politics may not be representative of the tech industry overall, but for better or for worse, 2025 is going to be the year when the loudest voices in the room are all adherents of the Great Man Theory, and they all happen to have direct access to the Oval Office.

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The Tragedy of Generative AI 

Yes, I have no patience for perfecting image prompts using AI.

Listen up, tech oligarchs; lend an ear, simpering brohanions. We’re doing this generative AI thing all wrong, and if you continue down your current path, your house of cards will fall, leaving all of us wanting, but most importantly, leaving you out of power. And given that you value power over all else, it strikes me it might be in your own self interest to consider an alternate path. 

Here’s the problem: you’ve managed to convince nearly all of us that sometime real soon, generative AI will deliver us powerful services that will automate nearly every difficult and/or deadly boring task we currently have to perform. From booking complex yet perfectly priced itineraries to delivering personalized health diagnoses that vastly outperform even the most cogent physician, your AI agents have us starstruck, bedazzled, and breath-baited.* 

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Vint Cerf: Maybe We Need an Internet Driver’s License

Vint Cerf is one of the most recognizable figures in the pantheon of Internet stardom – and as he enters his ninth decade of a remarkable life, one of its most accomplished. I had the honor of interviewing Dr. Cerf last month as part of the “Rebooting Democracy in the Age of AI” lecture series hosted by the Burnes Center for Social Change at Northeastern University. The conversation also served as the kick-off to my own Burnes Center lecture series, “The Internet We Deserve” where I’ll talk with notable business, policy, technology and academic leaders central to the creation of the Internet as we know it today (last week I spoke with Larry Lessig). 

Universally recognized as one of “the fathers of the Internet,” Cerf’s many awards include the National Medal of Technology, the Turing Award, the Presidential Medal of Freedom, the Marconi Prize, and membership in the National Academy of Engineering. Dr. Cerf received his PhD from UCLA, where he worked in the famous lab that built the first nodes of what later became known as the Internet. He has worked at IBM, DARPA, MCI, JPL, and is now Chief Internet Evangelist at Google. Cerf has chaired, formed, and participated in countless working groups, governing bodies, and scientific, technological, and academic organizations. 

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