Category: Joints After Midnight & Rants

Inadvertent Time Travel

Uh oh.

A week ago I knocked my phone – a Google Pixel 8 Pro – off the table and watched helplessly as it bounced awkwardly onto the stone floor of our favorite restaurant. After retrieving it I noticed a splotch of dead pixels in the top right corner. This was a new phenomenon – I was expecting a cracked screen. But the display sported what looked like a deep bruise. Over the next few days, the black spot spread slowly toward the phone’s front facing camera. By midweek, the Pixel’s light sensor was enthusiastically involved, and my phone was rendered unusable.

I live on an island, so a quick repair or replacement is not an option. That’s why I keep my old phones in stock – it can take up to three weeks for a FedEx or UPS shipment to find its way to my home. I ordered up a replacement online (I settled on the Pixel 10, as the new 11 is on backorder for more than a month), fired up an old Pixel 6, and popped in my SIM.

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The Essential Question: Can We Control AI?

(260717) — SHANGHAI, July 17, 2026 (Xinhua) — Chinese President Xi Jinping delivers a keynote speech at the opening ceremony of the 2026 World AI Conference and High-Level Meeting on Global AI Governance in Shanghai, east China, July 17, 2026. (Xinhua/Shen Hong) (Photo by Shen Hong / Xinhua via AFP)

August is often dismissed as a lost month in the business world – nothing gets done because everyone is on vacation. But where I live, August is the apex of the year. A heady mix of artists, financiers, philanthropists, business leaders and politicians converge on our little island for the month. The ensuing deluge of lecture series, film screenings, impromptu house concerts, and remarkable dinner conversations can be overwhelming. Four weeks into the month, those of us who live here are a bit strung out, ready for the tide of intellectual and cultural offerings to recede. Fall becomes a time to repair.

As might be expected, one topic dominated the conversations I’ve had at countless dinners, soirees, and fundraisers this summer. Yes, it’s “AI,” but that was true last summer, and even the summer of 2024. This year, however, the discussions turned from wonder and anticipation to something…darker. A central question came up over and over again: Is this technology – and the leadership behind it – fundamentally out of our control?

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What’s Next?

Artwork Rick Griffin

I’ve been trying to connect with a journalist who reached out a few days ago. He’s working on a story from way back in my career – the early days of Wired, circa 1995. It’s taken a few attempts to find a time. Despite the fact I’m no longer running a company full time, my days are still packed with meetings and obligations and new priorities. It probably doesn’t help that I keep my phone silenced, so I miss serendipitous calls, a favorite tactic of good journalists. But between various board meetings, community work, time blocked for writing, client and advisory work, investment reviews, exercise, and friends and family, squeezing in a 15-minute call feels just as hard now as it did when I had an EA, a Chief of Staff, and two full-time jobs*.

Is it strange that while I’m not “working” nearly as much as I used to, I still feel just as busy? Is that a good thing, or a problem?

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Who Stole My Alpha?

Have you seen Alex Karp’s rant on CNBC? I fielded this question about a dozen times over the past week. If you’ve not yet watched, it’s well worth your time. In a conspiratorial diatribe against the evils of monopoly-crazed frontier labs, the founder of defense-tech giant Palantir asserts that OpenAI, Anthropic, and Google are ruining our economy by “stealing our alpha” (more on that in a second). And because he’s a founding member of the Valley’s newly emboldened MAGA elite, Karp manages to toss in a few unhinged political dog whistles, implicating both UC Berkeley and “wealth taxes” as complicit in the downfall of civilization as we know it.

Despite obviously talking his own book – Palantir sells an application layer that sits above frontier models and ensures clients will not have their “alpha” stolen – Karp makes a point that has resonated deeply across not only tech, but the entire economy. “He’s not wrong…” is how several of the emails I’ve received have begun. “He’s got a point,” they continue, “even if he is kind of toxic.”

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Have We Lost The Plot?

Detail from Wired’s photo-Illustration: Jobanny Cabrera

“Our lives have become dematerialized.”

That phrase – from author Ian Bogost in a short piece in Wired – struck at the center of something I’ve been trying to verbalize for years. Bogost argues that technologies of convenience and efficiency have destroyed our connection to the physical world. His primary example is the automobile – first the automatic transmission replaced our physical connection to the road, then the EV made gears obsolete. Now driving itself is retreating into a digital interface – Waymo, Uber, and Tesla are seeing to that.

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Is AI Inherently Anti-Social?

 

Are you feeling lucky, or lonely?

All aboard ha ha ha ha ha ha ha
AI, AI, AI, AI, AI, AI, AI!

– Crazy Train, Ozzy Osborne (with slight modifications)

***

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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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