Category: essays

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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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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Google Encloses The Web

Last month Google announced the most significant change to its search product since its launch in 1998. Its iconic search box, which I’ve long compared to a command line for the Internet, has been redesigned to incorporate multi-modal chatbot capabilities. In essence, Google is no longer going to send you off to the best possible destination for your query. Now it’s built to capture your input and convert it into answers (and actions) all in one place – on Google.com.

Google’s announcement was expected – the company had to compete with the new paradigm of “answer engines” from OpenAI and Anthropic. But when the shoe did drop, my inbox filled with trepidation. Google has been the beating heart of the Internet’s circulatory system. Now that it’s evolved into a self-contained walled garden, how will the open web survive?

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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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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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Tech 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. 

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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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Who Owns Your AI Identity? (Hint: Not You)

As generative AI reaches a fever pitch of investment, product releases, and hype, most of us have ignored a profound flaw as we march relentlessly toward The Next Big Thing. Our most dominant AI products and services (those from OpenAI, Google, and Microsoft, for example) are deployed in the cloud via a “client-server” architecture – “a computing model where resources, such as applications, data, and services, are provided by a central server, and clients request access to these resources from the server.”

Now, what’s wrong with that? Technically, nothing.  A client-server approach isn’t controversial; in fact, it’s an efficient and productive approach for a company offering data-processing products and services.  The client – that’s be you and your device – provides input (a prompt, for example) which is relayed to the server. The server takes that input, processes it, and delivers an output back to the client.

Non-controversial, right? Well, sure, if the “server” in question is a neutral platform that’s only in the business of processing your data so you can use the services it offers. Banks, for example, use neutral client-server architectures to provide online financial services, as do most health care providers. The data you share with them isn’t used for anything other than the provision of services.

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Should AI Write Our Fiction?

I’m going to try to write something difficult. I don’t know if I’m going to pull it off, but that’s kind of the point. This is how writers improve: We tackle something we’re not sure we can do. Along the way, I am committing a minor sin in the world of writing – I am writing about writing.

But wait, don’t bail, here’s a topical tidbit to keep you engaged: I’m also going to write about AI, and who doesn’t want to hear more about that?! My prompt, as it were, is “Audience of One,” a post by Mario Gabriele, who writes the interesting and hyperbolic newsletter The Generalist. Gabriele’s optimistic prose focuses on venture, startups, tech, and tech culture. I find his work thought provoking and sometimes infuriating. “Audience of One” falls into the latter category.

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The Tragedy of Generative AI 

Yes, I have no patience for perfecting image prompts using AI.

Listen up, tech oligarchs; lend an ear, simpering brohanions. We’re doing this generative AI thing all wrong, and if you continue down your current path, your house of cards will fall, leaving all of us wanting, but most importantly, leaving you out of power. And given that you value power over all else, it strikes me it might be in your own self interest to consider an alternate path. 

Here’s the problem: you’ve managed to convince nearly all of us that sometime real soon, generative AI will deliver us powerful services that will automate nearly every difficult and/or deadly boring task we currently have to perform. From booking complex yet perfectly priced itineraries to delivering personalized health diagnoses that vastly outperform even the most cogent physician, your AI agents have us starstruck, bedazzled, and breath-baited.* 

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