Scripting News podcast

<p><i>Notes prepared by Claude.ai.</i></p><p>Dave opened with an aha moment he'd been chasing for years. Long before ChatGPT, he wanted to load all his blog writing into a machine and have it grind through everything to produce a table of contents — the kind you'd find in the back of a book — surfacing the items with eighty references pointing at them and the recurring themes running through his timeline. He pointed to the browser wars of the 90s as an example, a period he wrote about heavily and, because his posts were read everywhere then, actually influenced. The dream was to load it all into an AI, read the index, and ask how a given idea developed over time.</p><p>What struck me is that his solution turns out to be almost embarrassingly simple, and it only took four years. Because Dave writes everything in OPML — and always has, all the way back to the beginning, sitting in public in the scripting news repo on GitHub — you teach the AI to read OPML, drop everything into one file, and tell it to read the whole thing. His key insight is that you have to tell it more than once: the model doesn't actually ingest everything on the first pass, and it doesn't mind being nagged. You coerce the whole corpus into the model, then start asking questions and have it build the index.</p><p>He framed this as the familiar pattern of suddenly understanding one level of the stack while having no clue what's below it — and being at peace with that, because the lower levels are someone else's job. From there he reflected on how societies keep growing more complex out of the same basic human material, and how it never quite occurred to him that he's one of the people who build that stuff. Fifty-plus years of programming, never stopping, even running a company with a day job and a night job where the night job was the software. What he gets off on, he said, is creating new interactions that work for people — the same impulse he sees in Ted Nelson, Engelbart, Ritchie, and Berners-Lee, who just made things instead of agonizing over whether they should.</p><p>He closed on two notes. First, a caution against fear: this is version 0.51, not even 1.0, and if the first airplane anyone ever saw were a 747 they'd be terrified — these things arrive gradually for a reason. And second, the thing humans do badly: we push forward and create amazing things, but we never clean up after ourselves. We're hoarders, and what we hoard is CO2.</p><p><i>Notes prepared by Claude.ai. It makes mistakes, but it's a good summary, more or less reflects what I said.</i></p>

<p><i>Notes prepared by Claude.ai. It makes mistakes, like where it was recorded, but gets the story remarkably well. </i></p><p>A solo Dave Winer podcast, recorded over breakfast in a parking lot in Kingston, NY.</p><p>The episode starts with something Dave read from Dries Buytaert, the founder of Drupal, arguing that open source developers have to care for ecosystems, not just their own source code. It landed, because Dave's spent the last couple of years getting close to WordPress and wrestling with a basic question: what is WordPress? Not a company with a single strategy the way Microsoft was in the 90s, where nothing shipped unless it fit the plan. WordPress is many entities at once, and Dave's sense is that the people inside it don't fully see the larger web they live in — which is a missed opportunity, because the web desperately needs building.</p><p>From there he gets to the thing that's been gnawing at him: nobody in tech expects breakthroughs anymore. He's a product maker, and what he really makes is opportunities — solutions to problems most people can't even parse, because they're not expecting anything new. He traces this back through his whole career. Outliners, which everyone misremembers as a chore. MORE in 1986, an easy hit because everyone already understood presentations. And a great story about licensing news photos from AP and Agence France-Presse for a Ken Burns–style screensaver of current events — and nobody believing he'd actually gotten the rights. Same disbelief, he notes, that surrounded his New York Times RSS feed, the real catalyst for RSS taking off. He invokes the ice-nine image from Cat's Cradle: once the Times was on board, the rest had to follow.</p><p>The emotional core is envy. Listening to Spielberg on The Rewatchables, Dave was struck by how filmmakers share ideas, talent, and each other's projects — and asked why he's never gotten to make his contribution where he's most able, bootstrapping ecosystems, without having to build and run a whole company to earn the seat.</p><p>He closes with the pitch: WordLand is the MacWrite of the writer's web — a reference design meant to show developers what a writing tool on this platform looks like, deliberately not trying to be the everything-app that would scare developers off. Underneath it sits wpIdentity, an API that talks to WordPress but isn't bound to it. Get one more implementation and you're on the road to a web standard. The takeaway: open source isn't enough. You have to protect open formats and protocols, use only web protocols, and make every part replaceable — and if you want anyone to believe that, you'd better have already replaced them yourself.</p><p><i>Notes prepared by Claude.ai</i></p>

<p><i>Notes prepared by Claude.ai.</i></p><p>In this episode, Dave returns to a theme he's been circling for years: the social web's central failure isn't a lack of features, it's the locked doors. Platforms like Twitter, Facebook, Spotify, and Amazon build genuinely useful tools, but they're designed to capture users and prevent the combining of one tool with another to make something new. This is the oldest fight in software—the tension between the "programming priesthood" who believe they have all the answers, and the tool makers and users who want new ideas to flow in around the programmers rather than be limited by what those programmers happened to imagine.</p><p>He recalls the early web arguments with Microsoft, when the freedom was exhilarating: "I want to ride up front with you. I don't want to get locked in the trunk." The danger, as always, is the moment a venture-backed company spots an open thing and races to turn it into a jail. Dave is blunt about the current pretenders—Bluesky, in particular—who claim to be revolutionary and open but control their users every bit as much as the platforms that came before, offering essentially the same impoverished toolset Twitter shipped back in 2006.</p><p>The hopeful turn is AI. Dave is doing his work now in Claude Code, and he sees something important happening: the people building these systems inside Anthropic, OpenAI, and elsewhere are building on open formats and protocols. There's a genuine web sensibility in there, in contrast to the stale playbook of Silicon Valley VC. He cites a piece that stuck with him—the observation that all the great new functions being built for the AI world are built for the machines, not for the people. That's what he wants to change. There's a moment here to unlock things that were locked and never should have been.</p><p>His proof that open technology can survive the attempts to own it is podcasting. The VC industry was certain it would control podcasting; it invested on that assumption, and it simply didn't work. Twenty-plus years on, you can still listen on whatever player you want, with nobody dictating what you can and can't do. Dave thinks the reason is that choice was built into the medium from the very first instant it existed—and once that happens, anybody can make one of these things and nobody can stop it. That was the original mission of the web, the euphoria he was writing about on his blog through the late 1990s.</p><p>He closes with the broader pattern: every genuine sea change has come from a sudden, dramatic boost in the power of individual developers, and that's exactly what's happening now. The personal computer made the machine yours to do whatever you wanted with. Networking and the web did it again. AI is the next one. The decisions about what gets built on are being made now, and his message to anyone working inside these companies is the one he's been repeating for years, to which people always replied that he was Don Quixote—right, but nobody would ever actually do it: get on board with the web. Stop throttling it, stop removing features, stop trying to own it. Let people figure out what they want to do.</p><p><i>As before I asked Claude.ai to do the show notes, from its point of view. As always if you really want to know what I said you have to listen. DW</i></p>

<p><i>As before I asked Claude.ai to do the show notes, from its point of view. I added links. As always if you really want to know what I said you have to listen. :-)</i></p><p>Dave Winer left a voicemail for his longtime friend <a href="https://feedland.com/?feedurl=https%3A%2F%2Fnakedjen.com%2Ffeed%2F">NakedJen</a> making the case that now is the moment to start playing with AI tools, particularly Claude. He <a href="http://scripting.com/2026/03/27/200053.html">describes</a> a creative breakthrough he's been experiencing — not because AI has suddenly gained new capabilities, but because his own thinking has evolved to the point where he can see what's possible and act on it.</p><p>He walks through a recent experiment: starting with a <a href="https://imgs.scripting.com/2026/03/27/imageFromGoogle.png?nodialog">screenshot</a> of a chat interface, he had ChatGPT mock up a version with his words, then brought that to Claude and asked for a working HTML front end. Minutes later, he had a <a href="https://rss.network/demo.html">running app</a> in his browser. The project is rss.network, a chat program built around RSS — territory Dave knows well, having previously built a similar tool around JSON called json.chat.</p><p>His pitch to NakedJen is personal and direct. He believes she has exactly the right combination of intelligence, humor, and systems thinking to thrive with this kind of work. His practical advice: start a session by narrating who you are and what you're about, then at the end ask Claude to produce a handoff.md file summarizing everything a new thread would need to pick up where you left off. Drag that file in next time. Iterate.</p><p>The voicemail weaves in a reflection on Jerry Garcia and Bob Weir — Dave drawing a parallel between the Grateful Dead's leaderless creative dynamic and his own way of working. He closes with characteristic optimism: there's still runway, still room to make something real before the billionaires figure out how to capture it all.</p><p><i>Notes prepared by Claude.ai.</i></p><p>PS: Apologies to <a href="https://en.wikipedia.org/wiki/Keith_Teare">Keith Teare</a> for not remembering his last name. It doesn't mean anything other than my brain freezes on memory sometimes, a result of age, not sentiment. :-)</p>

<p><i>As before I asked Claude.ai to do a synopsis, from its point of view. I added a link to Brent's post and a postscript. As always if you really want to know what I said you have to listen. :-)</i></p><p>Dave opens by riffing on a <a href="https://micro.inessential.com/2026/03/13/code-is-a-liquid-now.html">post</a> by Brent Simmons, who described feeling, for the first time in his career, that he has his app completely under control — no chaos in the source code. Dave almost believes it's possible, but notes the catch: you can only get there on the fourth or fifth implementation of a given piece of software. The more complex the app, the harder that is to achieve.</p><p>He reflects on the tension between experimentation and stability. You can't try out new ideas on a mature codebase without actually building them out fully — there's no halfway. Like driving a car, you can't get a real feel for a feature if you leave out the steering wheel. So you build the whole thing, knowing you might throw it away.</p><p>Dave admits he's not in that place with anything he's working on now. The one exception, by design, was Frontier — built to be extended by users, which gave it a different kind of coherence.</p><p>From there he shares a vivid memory: demoing an early outliner at the West Coast Computer Fair, probably 1979, with Ted Nelson standing right next to him. Nelson watched the demo and said, simply, "That's virtuality." Dave unpacks what he meant: the suspension of disbelief. When software is truly good, you forget you're using it. Your fingers work at the base of your spine, your ideas appear on screen, and your full conscious attention is on the work itself — not the tool.</p><p>He extends the analogy to skiing: your first run you're thinking about mechanics and fear; by the third run, you're just going down the hill being yourself. That's the same feeling. Bike riding gets there faster with less overhead, which Dave notes is, honestly, a better deal.</p><p>He closes by thanking Brent for the thought, and wonders if AI tools might make that state of software mastery more broadly achievable.</p><p><i>Notes prepared by Claude.ai</i></p><p>PS: This is Dave. I never got around to explaining what was awful about reading Ted Nelson's book. It was awful because I thought I had had <i>original</i> ideas, but someone got there before me, Doug Engelbart, and Nelson wrote up Engelbart's ideas in great agonizing detail in Dream Machines. </p>