Category: Life

I’ll Be Framing My AI Check

This is a fake check!

I’ve always loved writing, and took to this form – the “thinking out loud” version of blogging – more than 20 years ago. I started Searchblog after I sold my first book, which focused on the impact of search on business and culture.  I decided I’d chronicle my reporting and build my voice by posting as often as I could, and the experience proved to be a watershed moment in my career. I built an audience that numbered in the hundreds of thousands, noticed scores of others doing the same, then launched a new company (Federated Media) based on insights from the experience.

The early 2000s marked the apex of what is now called “the open web,” and today two stories may as well be considered obituaries for the era.  The first, by Kate Conger at the NYT, lays out the mechanism for the open web’s demise: “Google Is Building an A.I. Fence Around the Internet It Once Championed.” The second brings news of a $1.5 billion settlement in a massive copyright infringement lawsuit targeting the AI industry. As an author, I’m a party to that suit – and at some point in the next year, a check from Anthropic will wend its way through the mail to me. A coda, of sorts, for an era already passed.

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Remembering Om Malik

Om Malik.

It seems almost quaint now, but there was once a version of the Internet ruled by influencers that were honest, high integrity folks who genuinely cared about the impact of their words.

Perhaps the most thoughtful of these was Om Malik, who passed away last week at the age of 59. Om was a colleague and a contemporary, and his site GigaOm was one of the earliest and most important partners at Federated Media, an early “record label” for bloggers that I launched in 2005.

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Quitting A Digital Habit

Amongst friends and family, I’m known as something of a digital curmudgeon. I’m usually the one person in group chats who does not use an iPhone, a habit I gave up in 2012 when I sensed that Apple was enclosing the entire mobile space. I stopped visiting Facebook and Instagram a decade ago, and I left Twitter in 2022, the year Musk took over. I refuse to employ AI chatbots as therapists, friends, or any kind of replacement for human engagement. I turned off all notifications on my phone – even for calls – 15 years ago.

Given my early bona fides in all things digital, I take a bit of pride in my heterodoxy, though in practice it creates friction, both for me and my friends and colleagues. Silencing notifications forced me into a new habit of checking my phone proactively, which one could argue has its own downsides. My Google phone breaks group chats, my absence from Meta’s products means I miss updates from friends and family, my aversion to AI therapy could mean I’m out of touch with how technology is changing society (though my adult children do keep me somewhat in the know on this count).

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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 Island Underground Radio Station

WVVY in Martha’s Vineyard – photo Robyn Twomey

This is a bit of a departure, but I figured I’d let you all know about a piece I wrote that was just published in our local paper. It covers a quirky underground radio station I stumbled across some years back. You can find the online piece here, and below is an excerpt:

Every Islander knows the drill: stuck in a line of traffic, slowly navigating one of the inescapable left-turn-fueled bottlenecks that bedevil our Island. Bored and possibly annoyed, we turn to our radios, hoping for a distraction to help pass the time.

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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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Magic and Mayhem (Predictions 2026, #3)

Magic maker

Do you remember the last time you felt the magic? When you encountered something truly novel, something that was both surprising and at the same time deeply familiar, because you had imagined such a thing, but until that very moment, believed it impossible?

I’ve had only a handful of such moments in my long relationship with digital technology. The first was in 1981, when I programmed a game of tic-tac-toe on an underpowered IBM PC. I compiled the crude lines of code I’d been assigned to write, issued the command “RUN” at the C: prompt, and damned if the thing didn’t actually work.

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The Standard, Part 1 – The End and The Beginning

A good place as any to lose your company.

Note: Third in a series. First post, second post.

The Oak Grove cemetery in Tisbury, Massachusetts encompasses roughly ten acres of rolling woodlands and narrow dirt roads. Its 1,800 or so headstones date back two centuries, making Oak Grove a relative newcomer as New England graveyards go. I’ve been visiting this sacred, spectral spot on the island of Martha’s Vineyard for nearly five decades. Half my family is buried there. 

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Get Wired: The Launch (1992-93)

The launch issue of Wired.

(continuation of a previous post)

If you ever have a hit on your hands, my advice is to take notes. Living in the whirlwind of blinding success is a little like experiencing your own wedding – everyone tells you to enjoy it, to remember every detail. But decades later, all you can recall is leaving the reception, relieved that everyone seemed to have a good time. 

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One Fateful Phone Call: How I Ended Up At Wired

The Iron Door, California’s Oldest Saloon. (It had a pay phone in the back).

Living at the cutting edge of technology in the early ’90s required either a magical token forged of copper and silver, or the capacity to memorize a ridiculously long string of numbers. Either the token or the code would connect you to a vast telecommunications network driven by immense computers housed in bunker-like buildings scattered around the world.

Labor Day 1992. I squeezed into a pay phone behind the oldest bar in California, The Iron Door, pride of Groveland, California – the “gateway to Yosemite.” I never could remember my access code, but I did have a token – also known as a quarter – which I slipped into the pay phone, then dialed my voicemail, a state of the art service that cost me an extra five bucks a month. Back then everybody used voicemail, it was an asynchronous lifeline to the rest of the world.

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