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.”
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.
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.
After writing about how OpenAI might just be the AOL of the post AI Internet, I couldn’t resist commenting on The Information’sscoop 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.
Back in the day when I was covering Google on a daily basis, I’d have spent hours poring over yesterday’s news that the judge in Google’s landmark antitrust case essentially blinked. But twenty-odd years of experience leaves me with very little to say about how Google’s first anti-trust case has been resolved, other than this: It’s a nothing burger, with a side of same-as-it-ever-was.
Over the course of nearly four years since the government brought its case, a lot has changed:
The United States has veered away from liberal democracy toward illiberal autocracy, and the current administration is no longer interested in grand antitrust remedies that serve the public. Today, everything is seen through the lens of whether a given action or decision furthers the President’s power. Preserving the status quo gives him leverage over powerful actors – he can continue to threaten and bully, ensuring fealty and tribute. In this administration, as in Moscow, Pyongyang and Beijing, no one is allowed to have more power than the Dear Leader.
As I laid out in my predictions nine months ago, the tech industry is now the most powerful force in politics outside the President, and its two most muscular companies – Apple and Google – did not want their duopoly upended. We’ll likely never know what soft-power backroom deals were cut to avoid what nearly every legal scholar felt was justified action by the government, but to think those dynamics didn’t impact this decision is to ignore the reality of my first point above.
OpenAI’s existence became a convenient foil. The emergence of generative AI has given Google (and the judge in this case) the ability to argue that the DOJ was fighting yesterday’s war. Sure, Google might have been a search monopolist, but look – OpenAI is proof that the market is always smarter than government regulators! Never mind the fact that search literally built the foundation for generative AI, or that generative AI is the natural evolution of search – a product that Google will continue to dominate now that government remedies have been rendered toothless.
Google – and its $20 billion partner Apple – are likely doing cartwheels today. Wall Street certainly is.
I’ve written a lot about AI lately, and I’ll admit, most of it is critical. Plenty of you have asked me why I’m so down on the sector. The crux of it is this: I think we’re approaching AI without considering history’s lessons, and because of that we’re failing to ask the questions that will matter as the technology becomes inextricably embedded in our culture.
Perhaps the most important question is metaphorical – what’s the best metaphor for how we interact with AI? We’ve got plenty of examples to chose from. Will our interactions with AI end up being like the PC – a personal device that we own and control? Or will it instead end up like social media or search (or worse, television) – a centralized service that is owned and controlled by large corporations?
Today brought so many stories worth “notes and observations” that I thought I’d try something new – a flash newsletter of sorts, with commentary on stories that pushed my eyebrows up a bit more than usual. Each of these items is worth a full-fledged long-form piece, but it’s Friday, so let’s be brief:
Do You Trust OpenAI? Over the past two years I’ve been warning that when it comes to long promised “user agents” that work on our behalf, AI companies would inevitably adopt the big tech playbook of providing centralized services that they control, ensuring that consumers are dependent on their platforms and by extension, locked into their services. This architecture is anathema to true innovation in a modern data economy, but inevitable given the capital constraints of current AI models. Well, this morning brought news of OpenAI’s “Agent,” which purports to “take over” our computers and take action on our behalf. As I’ve asked, over and over, is this the way we want the future to unfold? Who exactly do we think OpenAI’s agent really works for? Hint: It’s not us, anymore than Facebook, Amazon, or Google ended up working for us.
(This piece is cross-posted from Signal360, where it first appeared)
OK, Google, What’s The Business Model?
“How did you go bankrupt?” Bill asked.
“Two ways,” Mike said. “Gradually and then suddenly.” -Ernest Hemingway, The Sun Also Rises
If you work in marketing, Hemingway’s famous passage about bankruptcy will likely resonate. The launch of ChatGPT in 2022 prompted dire predictions that search’s role as a reliable driver of traffic and sales was coming to a close. For the past three years, however, those predictions seemed overwrought. Despite a slight dip in January, which proved temporary, Google has maintained a steady grip on 90 percent of search activity, and continues to direct a firehose of leads and commerce across the web.
But rather suddenly — in the past two months, in fact — it seems everything has changed. Google announced and immediately shipped “AI Mode,” its answer to OpenAI’s ChatGPT. The company had already implemented “AI Overviews” in 2024, essentially an evolution to its “One Box” feature that provides AI summaries for queries above Google’s familiar list of blue links. According to one study, those summaries are already responsible for a nearly 35 percent decline in outbound clicks — the lifeblood of traditional search engine marketing.
Google knows the question is no longer if AI is replacing search, but rather how quickly. Industry analyst Mary Meeker has an answer: AI adoption, she asserts, represents the fastest change in consumer behavior in the history of digital technology.
With AI Mode, Google has decided to push all in. The company understands that consumers are finding AI chatbots a superior search experience. One recent study found that “more than a quarter of Americans (27%) now use AI chatbots like ChatGPT instead of traditional search engines.” And consulting giant Bain found that “about 80 percent of consumers now rely on “zero-click” results in at least 40 percent of their searches.”
Google knows it’s taking a risk by moving quickly, but no matter what, it must keep its grip on the information-gathering habits of its billions of consumers. That leaves a major question unanswered: If search as we knew it is going away, what will replace search marketing as we knew it? What will supplant the time-honored practices of “SEO” and “SEM”?
If you’ve been exploring this question, you are most likely overwhelmed by a slew of firms, from early stage startups to massive agencies and consulting firms, all claiming an intuitive and familiar answer: “SEO, but for answer engines.”
Some call it “GEO,” short for “generative engine optimization,” and others have dubbed their solution “AEO,” for answer engine optimization. Regardless of nomenclature, the goal is the same: a set of best practices that position a product, service or brand to succeed in the brave new world of AI chatbots.
Chatbots “have been a huge wake up call,” says Pete Blackshaw, CEO of BrandRank.ai, a startup that helps brands adapt to what it calls the “answer economy.” “The trillion-dollar brand marketing industry is being severely disrupted by AI search, and marketers don’t know how to measure it, where to start, or how to win.”
It’s still early, but what’s already clear is that “winning” in AI search means playing a very different game. AI chatbots are the ultimate black boxes – even the companies that run them have no idea how the technology chooses its answers. That means marketers accustomed to precise dashboards of SEM and SEO-driven results must go back to basics. Blackshaw advises his clients to focus on understanding the content ecosystem that informs answer engines’ inputs. The often neglected brand website, for example, “is a fueling station for an AI chatbot,” he says.
Along with similar offerings from companies like Anvil and Profound, BrandRank offers dashboards to help clients understand how their brands are performing inside various answer engines like Perplexity, Claude, ChatGPT, and Google. Once you understand where you stand, you can get to work building out content strategies that might improve your brand’s performance overall.
If that sounds squishy, that’s because in an age of chatbots, it’s harder for brands to hide behind paid marketing. Answer engines scour a massive corpus of data to source their answers, and seem to favor community forums like Reddit or authoritative sites like Wikipedia — neither of which are particularly easy for marketers to influence.
“You can’t control how or when you’re going to be mentioned” in AI answer results, observes Bill Gross, the fabled inventor of paid search, now CEO of ProRata.ai. “There’s no statistics, no reporting.” Gross believes he has a solution: ProRata has developed a platform that builds AI-generated ad units that are contextual to the content of a particular chat. In short, Gross is building AdSense for AI – an approach that allows marketers to buy their way into the AI conversation. But it’s still early days — ProRata has yet to sign a major client like Claude or Perplexity.
In the end, what matters most will be how Google adapts its world-beating advertising services to the emerging experiences of AI chat. For now, Google is treating the various “surfaces” of its AI products as just another channel for its massive AdWords and AdSense businesses. But sometime soon, the company will be compelled to roll out AI-specific advertising units that are purpose built for AI conversations.
What might that look like? On that question, Google has so far remained mute. “Everyone thinks we know the answer to that question,” one source inside Google told me. “We might know more than many,” my source continued, but when it comes to what an AI version of AdWords might look like, an admission: “We don’t have a clue.”
Regardless of whether or not Google has a plan to pivot its $350 billion advertising business toward AI, the fact remains that hundreds of millions of consumers – in particular younger generations – now deploy AI-powered chatbots like OpenAI’s ChatGPT and Anthropic’s Claude to do everything from work-related research to more traditional search behaviors like comparing product reviews or finding new restaurants to visit. Oh, and on the horizon? AI agents that do the searching and possibly even the purchasing on behalf of consumers.
Given the pace and complexity of change, seasoned experts in search advise brand managers to move to a wartime footing. The rise of AI is likely to be “more impactful than the introduction of the Web in the mid 1990s,” said GoFundMe CEO Tim Cadogan, an industry veteran who ran search at Overture and Yahoo, then helmed OpenX during the rise of programmatic advertising. To win the day, marketers must be “extremely observant and agile,” he continued. “I don’t think any of us know what is going to happen. Whatever happens will happen very quickly. We have to be prepared to throw out the old ways of doing things.”
Cloudflare founders Matthew Prince and Michelle Zatlyn from a 2015 SXSW presentation (image)
There are precious few companies in the tech world that are willing to stick their necks out and “do the right thing,” and even fewer who both operate at Internet scale and enjoy Wall Street’s unabashed fandom.
In fact, I can only think of one: Cloudflare. And today, the $65 billion public company* announced a new policy that has the potential to tilt the balance of the Internet back toward the little guys. Starting this morning, Cloudflare will automatically block AI crawlers from copying the content of every website the company protects. And it’s doing it for free.
Back in the day when I was covering Google on a daily basis, I’d have spent hours poring over yesterday’s news that the judge in Google’s landmark antitrust case 
