Category: Joints After Midnight & Rants

Where’s My AI Shareware?!

Back in the day.

Have you noticed all the folks bragging about the cool new tools they’ve hacked up using AI? In the last month or so, I’ve read newsletters from half a dozen or so people detailing vibe-coded apps that help them do research, organize their life, or even build entire websites. And it’s not just media types who are building things. As I wrote about earlier, my son built a custom CRM system for his company over one weekend. That kind of capability is impressive. It feels like something new and big is underway.

Which got me thinking. If we’re all hacking up these cool tools, how come we can’t share them with each other? Why are we all consigned to re-invent the wheel each time we want to build, say, a “Searchblog Query Engine“?

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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 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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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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I’m Sorry, LinkedIn!

I’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.”

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Do You Trust The Conjurer? (Predictions 2026, #1)

Cecco de Caravaggio The Conjurer (The Musician) c. 1600-1620

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?

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Battle Lines Are Drawn (Predictions 2026, #2)

The 1960s ain’t got nothing on today.

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. 

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Is 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.

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The Planet Is Warming, But Our Speech Has Chilled

Image from the AlphaEarth launch.

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.

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