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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Anthropic Says the Quiet Part Out Loud.

This essay from Anthropic CEO Dario Amodei is… a lot to parse. But this passage alone makes me take it seriously:

“It is somewhat awkward to say this as the CEO of an AI company, but I think the next tier of risk is actually AI companies themselves…the governance of AI companies deserves a lot of scrutiny.”

So much to say about this. But read the essay. Then we’ll talk.

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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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What I’ve Learned: On Health

The holidays bring us all a moment to reflect. If you’re like nearly everyone I’ve spoken to these past few weeks, 2025 offered a lot of grist for contemplation. I usually write my predictions for next year around this time, but today I’d rather think out loud about something a bit more personal.

2025 was the year I turned 60 years of age. I hesitated before writing that sentence, because … well, like everyone I know who’s made it this far, I’ve become obsessed with understanding what it means to face the inevitable social, physical, and emotional impact of “getting older.” It’s probably one of the driving reasons for investing a considerable portion of the past two years of my life into DOC, a new company focused on the science of longevity medicine.

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Grading My 2025 Predictions

Nostradamus, so predictable.

All year long I monitor my annual predictions, taking note when events either make me a fool or a sage. 2025 marked perhaps the most unpredictable and frustrating year of them all – and that’s not nothing, given I started prognosticating in 2003. But then again, I did expect an odd one – from my 2025 post: “This isn’t going to be a normal year. 2025 will be strange, frenetic, and full of surprises.”

I titled my post “Tech Takes the Power Position.” While I didn’t make that sentiment one of my specifically numbered predictions, it did provide the context for how I was thinking about the year ahead. “We’re not accustomed to the tech industry having this much raw power. The finance industry? Sure…But this year, for the first time ever, Big Tech has leap-frogged finance in the pantheon of political influence…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.”  …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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Two Approaches to Saving The Web. Only One Works.

Image Gareth Glaser https://www.linkedin.com/pulse/appeal-open-internet-gareth-glaser-kwnbe/

The open web – free content written by actual humans about things actual humans care about – has been in decline for more than a decade. I’ve had a front row seat throughout – first at Federated Media, which was built 20 years ago to support independent publishers, then on the Board of Sovrn, which continued Federated’s work on the programmatic/data side of the publishing business. I’ve also taught and practiced journalism for the past few decades, and started and advised countless ventures that depend on traditional media revenue streams.

In short, I know it ain’t pretty out there for advertising-supported publishing. Social media dug the grave, and now the nail gun of generative AI seems to be merrily fastening the lid over the open web’s pine box coffin.

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Is OpenAI Today’s Netscape? Or Is It AOL?

As is his want, last week Fred Wilson wrote a provocative post I’ve been thinking about for the past few days. Titled “Netscape and Microsoft Redux?“, Fred notes the parallels between the browser wars of the late 1990s and the present-day battle for dominance in the consumer AI market. And he asks a prescient question: What new, world-defining product might we be missing by focusing on AI chatbots?

In the early days of the Web, everyone thought the most important new product to emerge from the Internet was the browser. Netscape, a startup with just a few months of operating history, defined the market for those browsers in 1994, then dominated it for several years thereafter. But by the late 1990s, the lumbering incumbent Microsoft had stolen Netscape’s lead by leveraging distribution and pricing advantages inherent to its massive Windows monopoly.

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Target Has an OpenAI App. Is That Good News?

Hey there, it’s been a minute. I got in a nice posting rhythm earlier in the year, but preparations for DOC (which was amazing, but exhausting) and life in general got in the way for most of the late Summer / early Fall. That’s starting to change, thank goodness.

If you’re a regular reader you know I’ve been somewhat obsessed with how AI will impact society and business – kind of like I was obsessed with how Search would impact society and business over the past two decades. An item about Target and OpenAI caught my attention this morning, news that, in more normal times, I’d have already written about in detail. Here’s the TLDR:

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Will AI Replace Doctors?

DOC 2025 Debaters: Reid Hoffman, Eric Verdin, Anitha Kannan, and Mike Krieger

At the inaugural DOC gathering last year, famed Valley VC Vinod Khosla made a bold prediction: AI will soon make medical care “essential free,” while at the same time enabling human doctors to scale their knowledge and caregiving five to ten fold. Bill Gates has made similar claims – and gone even further, saying that AI will “replace many doctors” with 10 years.

As we all contemplate a future of “AI everywhere,” perhaps no question is more polarizing than this: Will AI make human work obsolete? And if so, what happens to all of us? It’s the defining question of Mustafa Suleyman’s 2023 book “The Coming Wave,” in which Suleyman, the CEO of Microsoft AI, argues that AI will have “hugely destabilizing” impact on the workforce. “Godfather of AI” Geoffrey Hinton strikes a darker tone, warning “What’s actually going to happen is rich people are going to use AI to replace workers. It’s going to create massive unemployment and a huge rise in profits. It will make a few people much richer and most people poorer.”

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