Are you frustrated with how the internet works?
Me too. Today I’m going to think out loud about why.
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Leave a comment on The Web We Want Vs. The Web We Have
The Web We Want Vs. The Web We Have
Category: Joints After Midnight & Rants
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.
Read MoreProduct, Platform, Interface, Medium, Language: What Is AI?
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.
Read MoreI’m Sorry, LinkedIn!
Earlier this week, as a major storm took aim at the little island where I live, I saw a story in which Sam Altman, CEO of OpenAI, defended his company’s energy use by comparing it to how much energy humans use to do similar tasks.
“…it also takes a lot of energy to train a human,” he argued, when asked about AI’s insatiable – and destructive – appetite for energy. “It takes like 20 years of life and all of the food you eat during that time before you get smart. And not only that, it took the very widespread evolution of the 100 billion people that have ever lived and learned not to get eaten by predators and learned how to figure out science and whatever, to produce you.”
Read MoreDo You Trust The Conjurer? (Predictions 2026, #1)
The modern English verb ‘to conjure’ is derived from the Latin conjurare, meaning ‘band together by an oath, conspire.’ Its roots con (‘with’) and jur (‘legal right or authority, law’) echo with questions central to our present day struggle with technology: Who do we trust to determine authority? Why do we believe in them?
Conjuring also evokes magic, sorcery, and wonder, essential elements of the tech industry mythos. My earliest pieces on the impact of generative AI leaned on the metaphor of magical “genies” doing our bidding in a relationship bound by loyalty and trust. Do those genies work for us, or are they the product of conjurers beyond our control? Do they demand faith, or instill it?
Read MoreBattle Lines Are Drawn (Predictions 2026, #2)
I concluded my post “Magic and Mayhem” with a bit of a tease about the impact of AI on our society:
There will be lots of magic this year. But there will also be plenty of carnage as previously unbreachable moats start to crumble, not only in business, but also in society at large. For more on that, stay tuned for prediction #2.
Read MoreIs 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.
Read MoreThe Planet Is Warming, But Our Speech Has Chilled
More than a decade ago I was working on a book about the impact of data on society. I was obsessed with a maddening and seemingly impossible idea: What if we could track every single piece of data that mattered in the world, and from that data, gain unimaginable insights that would shake us into an entirely new age – the equivalent of moving from Medieval times to the Renaissance?
Of course, I was struggling with this thesis well before AI became mainstream. I knew that the compute and algorithms needed to turn my musings into reality were on the horizon, but I simply could not find a way to realize the concepts I sensed were playing out all around me. I felt like Captain Ahab, madly chasing a spectral leviathan of data. I spent days staring out at the ocean from a rented cottage on the beach, imagining every molecule of water as information dancing across sentient processors. It was about this time that I made an uneasy peace with my ambitions to be the next Gleick or McPhee. Rather than submit to the insanity of the matrix, I abandoned the project, and it has haunted me ever since.
Read MoreTech And Society’s Faustian Bargain
Capture.
I led my predictions for 2025 with the dog-bites-man observation that technology has eclipsed finance as the most powerful industry in the world. More than six months into the year, I’d like to emend my conclusion. Tech hasn’t eclipsed finance. It has captured it.
Finance has always leveraged technology – at Wired in the early 1990s, we were fond of saying that technology’s twin engines of innovation were money and sex – but the most interesting story was always money. Care to understand the future of internet infrastructure? Bone up on how hedge funds optimize network latency. Want to peer into the future of online consumer services back when the Web was a glint in Marc Andreessen’s eye? Start with online banking.
Read MoreIf You Trust AI, You’re Asleep. (At Least You’re Not “Woke”)
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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