I’m not even finished with my predictions this year, and already one of them is coming true. In The Year Tech Gets Even Bigger (Predictions 2026, #7), I wrote:
Google in particular will be building a Death Star of AI distribution featuring all the same players from its days of search monopoly: Apple, Samsung, and other Android partners.
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Ten years ago a new and promising technology burst into our homes – the smart speaker. Like many tech-forward families, our household went all in. We got two Alexa speakers and two Google Homes, plugged them in, and they became fixtures in our kitchen and bedrooms for years.
Problem is, we kind of hate them now. At first they were cool – it was novel to talk to a device and have it actually work, at least for simple tasks like “what’s the weather today” or “play Vampire Weekend.” But we quickly grew disaffected with our new purchases, because more often than not, they failed when presented with even moderately complicated queries like “what time is the Giants game tonight” or “what’s on my grocery list.” In short, the first generation of smart home speakers were limited by a rigid approach to “intelligence” that didn’t scale. Only one sad, bedraggled Google Home remains in service in our kitchen, serving as a glorified clock radio (that’s it in the picture above). And it’s not doing Google any favors in the branding department, because whenever we ask it anything even slightly complicated, it fails, earning a string of expletives in the process*.
Read MoreFor the past many years one prediction has proven reliably accurate: There will be no significant Federal regulation of the technology industry. At times this stalwart prognostication has been tested by major anti-trust actions – but each has proven ultimately toothless. This year, for example, we’ll learn what the DOJ managed to accomplish in its second case against Google – and it’s still possible a judge will rule that the search and AI giant must divest itself of its adtech infrastructure. But I don’t think so. And even if that ruling does come to pass, Google knows it can simply appeal, dragging out any eventual impact until it wins a war of attrition with an increasingly feckless and uninterested DOJ.
Besides, arguing about the past is playing yesterday’s game, and in 2026, the game has reverted to an even older playbook. For the past five or so years, tech giants have had to play defense when it comes to M&A and sweetheart partnerships – Meta was being sued over its acquisitions of Instagram and WhatsApp, Google over its consolidation of adtech and its domination of search distribution through deals with Apple and Samsung, among others. But in 2026, the governors are coming off.
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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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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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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:
Google – and its $20 billion partner Apple – are likely doing cartwheels today. Wall Street certainly is.
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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.
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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.
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Bill Gross has been here before.
Back when the Internet was young, when the dot-com wave broke across the monied shoals of Wall Street opportunism, Gross built a world-changing company, took it public, then sold it for billions.
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There’s this throwaway conceit in the current season of Black Mirror that keeps tugging at me, and it’s Friday, so I thought I’d think out loud about it.
In Episode 1, “Common People,” the protagonist, a school teacher, is lecturing her young pupils about pollination. She casually explains how robotic bees have taken over for their organic ancestors, buzzing from flower to flower and, one presumes, keeping the world’s agricultural ecosystem from crashing. The exchange is meant to contextualize the episode as happening sometime in the near future – most of us know that the bee population is crashing, and the concept of autonomous insect drones doesn’t feel that far off. It’s also an elegant reference consistent with one of tech’s most fundamental beliefs – don’t worry, kids, technology can and will save us from ourselves!
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