derek smart-gordon

grep: dev lead. building ai things at automattic.[]

20265 posts

  • may  7 Say Hello to Dolly essays

    Every so often someone at work says “what if we built…” and then we build it. That’s how we ended up with Dolly, an AI assistant for WordPress.com…

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  • apr 24 Context fundamentals notes

    Earlier this year I gave the same sixty-minute talk enough times to notice that the useful part always started right as the clock ran out. So I made…

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  • apr 15 Switcheroo: a tiny hosts-file editor for macOS tools

    For years I used Gas Mask to manage my hosts files. It worked for me. It is also, at this point, abandoned and increasingly cranky on Apple Silicon. So…

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  • mar 12 Your assistant essays

    Not “the assistant.” Your assistant. Every AI assistant bolted onto a product is the same anonymous thing. A chat box in a sidebar, no name, no memory of…

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  • feb 28 Authority to act essays

    We spent the last 20 years making it easier for people to build websites. I think the next stretch is about websites that build themselves, and then keep…

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20253 posts

  • aug  4 Since the April launch notes

    I wrote up the summer’s improvements to the WordPress.com AI website builder on the WordPress.com blog: What’s new with our AI website builder. Since the April launch: better…

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  • jun 11 The free one was better notes

    People with existing paid WordPress.com sites are asking support to move their plan onto the site they built during the AI builder’s free trial. Five or more of…

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  • apr  9 Big Sky notes

    Big Sky is public today, as the WordPress.com AI website builder. Describe the site you want, watch it build, then change things by asking in the chat or…

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20241 post

  • nov 11 Soft launch notes

    Big Sky, the AI site builder we’ve been working on for most of the year, went live for real WordPress.com customers today. No announcement, it’s a soft launch.…

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20222 posts

  • oct 23 When Safeguards Fail: Optimize for recovery essays

    Meet Kevin. She (yes, Kevin, a story for another day) loves spending time on our third-floor balcony. While I trust her inherent cat skills, my wife is less…

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  • jul 10 Shipit of Theseus essays

    When all the code has been rewritten, is it still the same product? Refactors. If you’ve worked in the same codebase for long enough you will have experienced…

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20191 post

  • nov 12 Get WordPress.org plugin info api tools

    I keep losing this link. Maybe I won’t need to Google it every time if I actually write it down. http://api.wordpress.org/plugins/info/1.0/jetpack.json So, for example, get a nice list…

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20161 post