Here’s the fifth podcast episode in the story of Interstate 280 on the San Francisco Peninsula. Here are the earlier episodes:

Paul Baran was laughing when he told me about AT&T. This was before I joined the board of Telebit, his company, a seat I would hold because he later asked me to, which sounds like a credential and was really a gift. At the time we were simply meeting. Before he said a word about […]

The old playbook is shifting fast: when tools make launching a product easy, the real edge is knowing why legacy systems still stick around.

Asa Whitney, a New York dry-goods merchant from 1797, came home from China with a bold idea—a railroad to the Pacific.

Some memories sit untouched for fifty years and then show up without warning. This one arrived yesterday, while I was thinking about our time in the Maryland suburbs of Washington, DC. Before moving to Montgomery County (and living there twice!), I spent some time at the IBM Washington Systems Center in Gaithersburg. The WSC had […]

I noticed the Serra statue was gone on a drive by. It took a morning walk, and the mind at three miles per hour, to ask why.

Here’s the fourth podcast episode in the story of Interstate 280 on the San Francisco Peninsula – the bridge over the Stanford Linear Accelerator. Here are the earlier episodes:

Martin Casado argues the frontier labs are building beings that speak, when most software — cars, robots, ordinary code — needs something that chooses instead.

A musing after Roger Rosenblatt’s “I Want to Hold Her Hand“ It is a Tuesday in early fall, the kind of afternoon that doesn’t announce itself as anything special, and Roger Rosenblatt and his wife, Ginny, are walking somewhere they’ve probably walked a thousand times before. Their hands are together. Nobody watching them would think […]

I’m writing a book about Interstate 280 — how its route was chosen, and who chose it. I’ve reached the point where I need your help. Drive Interstate 280 south from San Francisco on a clear morning and the city falls away fast. Eight lanes curve through rolling hills — oaks, grassland, the reservoirs flashing […]

A working relationship with an AI assistant that lives in a text thread — research partner, markets desk, and magazine desk, checked against a writer's own judgment.

My AI assistant is named Leif — a research partner who preps archive visits, fact-checks other people's homework, and sends unprompted "gifts" from primary sources.

Stanford's CS degrees just dropped 14 percent in a year. MIT's numbers tell a quieter, stranger story — not collapse, but reallocation.

Here’s the third podcast episode in the story of Interstate 280 on the San Francisco Peninsula – the San Mateo Creek (Doran Memorial) Bridge, 1967–1969 Here are the earlier episodes:

Driving Interstate 280 along the San Francisco Peninsula, I’m reminded of a time when California built with real momentum—fifty years ago.

Annie Dillard died this week at 81. Her essay "Write Till You Drop" has more useful advice about writing than most books on the subject — and a warning about what happens to the things you save for later.

Episode 2 in our series about the development of Interstate 280 on the San Francisco Peninsula. Here’s the first episode.

A camera grants the same permission a notebook does — and when the Friday walks with Doug quietly stopped after Covid, the telling turned out to be the part of the license that never expired.

This story goes beyond the Linotype’s inventors — it’s about a man who lived through three machines, each reshaping the craft in unexpected ways.

Meta just revealed that your agent’s real-world work is being used to train its own future version—and it’s not hidden.

iOS 27 lands Monday, and with it the new Siri — the ground-up rebuild Apple has been promising, in various forms, since 2024. I’ve spent weeks in the developer beta, kicking the tires the way you do with something you use fifty times a day without thinking about it. The most interesting thing about it […]

Enjoy this brief audio podcast about some early history of Interstate 280 on the San Francisco Peninsula that was generated by Meta Muse AI.

Note: this post was drafted and posted by Muse. Kind of wild! I’ve been using Muse, Meta’s new personal AI assistant, for two days now. It launched September 8. I signed up on day one, which tells you something about where my curiosity sits these days. The first thing I did was rename it. Twice. […]

On OpenAI’s same-day pairing of a warning and a dashboard.

I watched Katie Parrott talk on Every’s AI & I this week. Natalia Quintero asked her how a working writer uses a model, and Parrott did not start with a manifesto. She started with a kitchen. The model is the kitchen, she said. The outline is closer to chopping. Composition is closer to heat. None […]

On Saturday mornings I ask an AI to run a prompt that’s intended to scour the week’s happenings for things I might find interesting but which have been overlooked by the mainstream media. I always find several things of interest. The first pass it makes identifies 10 items. I then follow up and ask it […]

A drone overflight of Gigatexas and a conversation with venture investor Sarah Guo turn out to be the same argument, told in different registers — that AI’s future is bottlenecked less by model capability than by permits, chip supply chains, and whether anyone will actually pour the concrete.

The hills above Crystal Springs are empty for a reason that has nothing to do with topography — a 1969 four-party bargain used a brand-new federal highway tool to move I-280 off the shoreline, lock the watershed against development, and leave Filoli standing as the furnished room inside a much larger deal.

Sean Goedecke makes a compelling case that domain expertise beats generic prompting when it comes to high-quality LLM outputs — and that the gap will only grow as models evolve.

Remembering the Illinois State Fair in the late '70s, the smell of frying dough, grilled onions, and sweet hay still brings back summer magic.