Category: Media/Tech Business Models

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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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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Magic and Mayhem (Predictions 2026, #3)

Magic maker

Do you remember the last time you felt the magic? When you encountered something truly novel, something that was both surprising and at the same time deeply familiar, because you had imagined such a thing, but until that very moment, believed it impossible?

I’ve had only a handful of such moments in my long relationship with digital technology. The first was in 1981, when I programmed a game of tic-tac-toe on an underpowered IBM PC. I compiled the crude lines of code I’d been assigned to write, issued the command “RUN” at the C: prompt, and damned if the thing didn’t actually work.

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AI Can’t Cost This Much (Predictions 2026, #8)

That’s some Big Iron you got there, Mister!

Some of you gave disagreed with my last prediction, that Anthropic would file for an IPO, stating, accurately, that OpenAI has a far more pressing need for fresh capital, given its commitments to various partnerships totaling  more than $1.4 trillion and counting. That’s a good point, but I don’t think OpenAI will ever really spend that money, and my next prediction explains why: I think the costs involved with delivering AI will come down significantly in 2026.

I’m not either an economist nor a supply chain expert, so what I’m about to write is informed more by historical rhyming than quantitative analysis. But when I see eye-watering numbers about the cost of data centers, compute, and chips, I start to wonder if innovation has been factored into the calculations. When trillions of dollars are projected to be spent, trillions that would require trillions more in revenue (and profit) to justify, a lot of butterflies start to flap their wings.

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Anthropic Goes Public (Predictions 2026 #9)

According to the Financial Times (and pretty much everyone else), 2026 has the potential to be the biggest IPO year in history. SpaceX, OpenAI, and Anthropic all could go public this year; the proceeds from those three combined “would outstrip the total haul from about 200 US IPOs in 2025.”

Were any one of the three companies to successfully complete a public offering this year, they’d not only make thousands of lawyers, investors, bankers, and employees very rich, they’d also be setting a record: Each company is already privately valued at well above the benchmark for the largest public offering in history, which was Alibaba’s 2014 debut at $170 billion.

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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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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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Algorithms and Capitalism: Cleaning Up The Waze Parade

Where are we all going?!

Do you feel it? A simmering discontent with the state of capitalism in American life? I certainly do. My kids engage with social media only if they have to – never because they wish to. They believe their feeds are  manipulated by corporate interests, and they are distrustful of anyone who believes otherwise. My wife is convinced that anything she buys online – particularly the bigger ticket items like flights or hotels – is priced based on what algorithms calculate she can afford to pay – not what might be fair or offered to others. Parents in my friend group are terrified that their kids are using ChatGPT as a confidante and therapist whose motivations are unfathomable. The stock market keeps pushing ever upwards, but my colleagues are increasingly convinced a crash is around the corner.

Something just feels….off. The complex socio-economic system that we’re all a part of seems rigged. And we feel powerless to do anything about it.

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OpenAI: Code Red? More Like Code Green!

 

After writing about how OpenAI might just be the AOL of the post AI Internet, I couldn’t resist commenting on The Information’s scoop this morning about OpenAI hitting the big red panic button. It’s now a Valley ritual to call an official emergency whenever you’ve made massive management mistakes that almost kill your company. Remember Sundar’s code red back when ChatGPT launched? Seems Sam Altman is now returning the favor. He’s worried Google’s Gemini is about to lap ChatGPT, and has told his staff to drop everything and focus entirely on improving OpenAI’s core product.

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