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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Options Destroyed

Descisions ahead road sign in warning yellow with blue background, – Illustration

Running a startup means making hundreds of decisions a week – some of them simple – which brand of coffee to stock in the kitchen – and some of them impossibly complicated – should I replace my founding CTO? When parsing through them, I always consider a piece of advice a long-time colleague once gave me:

“There’s no value in an option destroyed.”

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The Island Underground Radio Station

WVVY in Martha’s Vineyard – photo Robyn Twomey

This is a bit of a departure, but I figured I’d let you all know about a piece I wrote that was just published in our local paper. It covers a quirky underground radio station I stumbled across some years back. You can find the online piece here, and below is an excerpt:

Every Islander knows the drill: stuck in a line of traffic, slowly navigating one of the inescapable left-turn-fueled bottlenecks that bedevil our Island. Bored and possibly annoyed, we turn to our radios, hoping for a distraction to help pass the time.

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The Web We Want Vs. The Web We Have

The Warrant for the Town of Oak Bluffs, MA.

Are you frustrated with how the internet works?

Me too. Today I’m going to think out loud about why.

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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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The Withline

 

The Withline

I spend a lot of time engaged in the craft of writing – I’ve penned more than 1.5 million words on Searchblog alone. Writing anchors nearly all my projects, from teaching at universities to my board and investing work, not to mention the hundreds of pieces I’ve either authored or edited at places like P&G Signal and DOC. I write a few pages nearly every day in longhand journal (I’ve filled nearly 30 of them over the past four decades), and I recently embarked on a long-form writing project that may (or may not) produce another book over the coming months.

So writing matters to me, and I’ll admit I’m uncomfortable with how generative AI is changing my chosen field. I recoil from the idea of AI-written articles, blog posts, or academic assignments. And I support the various efforts by authors, journalism institutions, and creative groups who are pushing back against what feels like wholesale theft of our work to train LLMs.

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Product, Platform, Interface, Medium, Language: What Is AI?

Thanks, Marshall.

What is AI?

I’ve been struggling with this rather basic question for several years now, so today I figured I’d write out loud about it, and see if anything coherent surfaces.

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Rebel, King, and Tyrant: Apple at 50

Wired, 1997: We were genuinely worried the company would go out of business.

Apple turns 50 years old tomorrow. I’ve been using its products for 48 of those years.

48 years. Over those five decades, my relationship with Apple has shifted as dramatically as its market cap. And not, I am afraid, in a good way.

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We Dream of Genies, But Will Big Tech Let Us Use Them?

Last night I dreamt I was merging onto a rushing freeway. My on-ramp was far too short, a concrete embankment hemmed me in to the right. Faceless, speeding vehicles filled the lanes; integrating with them would require icy determination and perfectly executed timing. Missing the merge would bring certain death. The dream began after the point of no return – I was already accelerating into the flow, braking was not an option.

Do, or die.

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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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