Category Archives: AI

Artificial intelligence, large language models, and how they’re changing everything.

Two interesting AI updates this week: It’s nice to read Andrej Karpathy’s review of Tesla’s FSD v13, as someone who was involved with creating their first self-driving efforts. I’ve only experienced v12, so very excited to try out the latest generations soon. Ubiquitous self-driving will reshape cities and save countless lives.

On the heels of announcing a $40B investment in Texas, Google has launched Gemini 3. It’s still funny how every organization ships its org chart with the naming and accessibility of the various models it releases, but, more broadly, it is so exciting to see so much intellectual capital focused on this area, with the frontier labs leapfrogging each other every few months. Every model has a feel, and with Gemini 3 you start to feel the breadth of Google’s long investment in the space show up in interesting ways. Yet it can still be beaten in coding by an upstart like Anthropic with a fraction of Alphabet’s resources.

What a time to be alive. Witnessing multiple excellent organizations ship the best work of their career rapidly is invigorating and inspiring; the competition drives better results, and the diffusion of new approaches is rapid. The consumer surplus that we all benefit from is just beginning to be felt; we’re maybe 1 or 2% impacted in the economy so far.

Conversation with John Borthwick

I’m often on the other side, but it’s such a delight to be an interviewer, I really enjoy it and put a lot of work into coming up with questions and shaping a conversation I think will draw out something novel from the person. Besides the Distributed Podcast, I’ve had a chance at events to interview great minds such as Steve Jurvetson, Patrick Collison, Dries Buytaert, and now John Borthwick.

We discussed his early investments in Airbnb and Tumblr, what made the NYC tech scene so special back then, and how it has evolved since. We also touched on the recent mayoral race, where Betaworks fits into the city’s tech ecosystem, and delved into one of my favorite topics: the comparison between open-source and proprietary models in AI.

On November 5th at our Noho office the legendary John Borthwick (investor in Twitter, Tumblr, Buzzfeed, Digg, Venmo…) and I will have a conversation on the future of the Open Web and human-centered AI. Please join us!

WooCommerce 10.3 is out, just in time for Black Friday / Cyber Monday, with some nice improvements to the checkout experience, tracking cost of goods sold, and a new beta MCP server, “This new feature enables AI assistants like Claude, Cursor, VS Code, or any other MCP-compatible client to interact directly with WooCommerce stores through a standardized protocol, opening up new possibilities for AI-assisted store management and development workflows.” You can also help out in testing WordPress 6.9, which comes out on December 2nd.

If I’m slow on anything right now, I apologize. I’ve got some flu/Covid thing, so I’m operating at reduced capacity.

Probably the most interesting thing on the internet today is Andrej Karpathy’s nanochat, “a minimal, from scratch, full-stack training/inference pipeline of a simple ChatGPT clone in a single, dependency-minimal codebase.” 8,000 lines of beautiful code, as Simon Willison notes. If you want to understand how LLMs work, study this. Andrej is a code poet.

In hacking news, Wired has an amazing article on intercepting geostationary satellite signals.

On Friday, we turned on something cool: every WordPress.com site now supports MCP. Right now this is read-only access to your site, because the S in MCP stands for Security, but you can already start to do some cool stuff with it.

Jeremy Kranz and Sentinel

AI, Automattic, Friends, Open Source, Tech

I’d like to introduce you to Jeremy Kranz. With his career as an investor at Intel Capital, then GIC, which is the sovereign wealth fund of Singapore rumored to manage over $700B, to now running his own fund Sentinel Global, he has had a front-row seat to investments in industry changing companies such as ByteDance (which became TikTok), Alibaba, Uber, DoorDash, Zoom, DJI (which changed the drone industry and argubly modern warfare), and many more I’m probably not even aware of.

When I first met Jeremy in 2014, I was amazed that a late-stage financial investor could understand Open Source so well, and he immediately grokked what Automattic was doing in a way that I think has little parallel in the world. (Today, it reminds me of Joseph Jacks at OSS Capital.) Deven Perekh of Insight Partners led Automattic’s 1.16B valuation Series C round, making us one of only forty “unicorns” (private companies valued over a billion dollars) at the time, and one of the reasons they beat out others as the lead of the round was that GIC/Jeremy was a LP of Insight so they could directly co-invest. GIC is so intensely private I couldn’t even mention them in the announcement at the time even though they were the catalyst for the round. Since then, Jeremy has become a close friend and advisor, and he even took me to my first Grateful Dead concert.

Eleven years later, this is his first podcast! Jeremy shares incredible alpha around China, AI and its adoption in the enterprise, how asset allocation is evolving, and at the end, a beautiful tie together of the Grateful Dead and Open Source.

Craft vs Slop

AI

In an age where AI can generate an infinite amount of stuff, what matters? Some of the most interesting writing I’ve read on this comes from Will Manidis, who makes it biblical and says that Craft is the Antidote to Slop:

From Genesis, man enters not a paradise without labor but a world of intentional creation. The LORD God places man in the Garden of Eden “to dress it and to keep it” (Genesis 2:15) establishing labor not as punishment but as sacred vocation. This original calling invites us to co-create the Kingdom, tending and developing the world with intention and care. Our fundamental purpose is not consumption but participation in the ongoing work of creation.

The serpent’s temptation represents the first shortcut in human history.”Ye shall be as gods” (Genesis 3:5) was not an invitation to deeper engagement with creation, but a way to get out of the work required to tend to it. The consequence wasn’t the introduction of work itself, but its corruption into burdensome toil: “In the sweat of thy face shalt thou eat bread” (Genesis 3:19). Humanity’s first sin was, in part, choosing the easy shortcut over the meaningful process – preferring effortless gain to the demanding but fulfilling work of tending the garden.

You can read the rest as screenshots on X or on his Substack, but I hope he gets a real website soon. This also makes me think you should watch the We Are As Gods documentary on Stewart Brand, supported by the amazing folks at Stripe Press.

Saturday Shares

AI, Automattic, Interview, Open Source

A few links for you:

Fun fact: this post has the ID of “150,000” in my wp_posts table.

Telex Remixes

AI, Automattic, Books, Design, Tech, WordPress

Telex has launched a new design and a gallery of some interesting examples. It’s really cool to see what people are starting to do with Telex, it really gets back at the fun of hacking and coding at the beginning, when a computer does something for you that makes you gasp.

My colleague Eduardo Villuendas has been making some cool music with it.

This really gets to my vision for Gutenberg to be a builder that anyone can use to create an incredible website, like legos anyone can assemble anything they imagine on the web. This is why I said Gutenberg is bigger than WordPress.

Hat tip to the Gutenberg Times. As I said in 2022, you need to learn AI deeply, there is so much fun stuff happening. Berkan Cesur even likes it on Reddit.

Nick Diego writes how Telex Turns Everyone into a WordPress Block developer.

MCP Everywhere

AI, Automattic, WordPress

MCP stands for Model Context Protocol. (The joke is the S in MCP stands for security, but that’s another post.) They say to think of it like “like a USB-C port for AI applications” because it allows interoperability between AI chatbots and other tools. Here’s some of the MCP stuff happening across the Automattic solar system:

When nerds start connecting things, interesting stuff happens; that’s been my entire career, so while none of these have made it into a critical daily workflow for me, I’m curious to see what people come up with.

Weekend YouTubes

AI, Interview, Politics, WordPress

One of my favorite YouTubers is Charles Cornell (WordPress-powered!), who creates great videos that break down the music theory of various things you’ve heard, such as this adorable one featuring SNES soundtracks or The Legend of Zelda: Breath of the Wild. I first came across him reacting to Jacob Collier in 2020. Once I got super-into Severance, his breakdown of the spooky music is great. It’s also interesting to see that the YouTube community is going through its own version of fair use and copyright, trademark, etc., enforcement, which he discusses here.

Sam Altman is always interesting to follow, and it’s interesting to contrast this great interview he did with David Perell on writing with this very direct and awkward one with Tucker Carlson. I have immense respect for anyone who enters the arena and engages directly with journalists or critics, rather than hiding behind PR agents or lawyers. Given the current blood feud, it’s fun to go back eight years and see Sam Altman interview Elon Musk, long before any of the AI stuff blew up they were both terribly prescient.

Ray Dalio is always a gem and he went on Diary of a CEO. Theo Browne has a good take on what it means to vibe code. Kishan Bagaria discusses how Beeper is going to reach 100 million users. The story of how Atlassian took a non-traditional enterprise path with Jay Simons is great. Not a YouTube, but don’t miss Bret Taylor on The Verge. Check out Adam D’Angelo at South Park Commons.

And finally, I’ll say that YouTube Premium, which turns off all the ads, is probably one of the highest value subscriptions you can have. Many of these are essentially like podcasts, and from a product perspective, I think we need to figure out how to sync and allow seamless movement between watching, listening, or reading transcripts in Pocket Casts (Automattic’s open-source podcasting app). We support video podcasts, but there’s no good way yet to have a Whispersync-like experience between video, audio, and a transcript.

A few interesting reads or listens:

Maker Taker

AI, Design, Open Source

My sister Charleen sent me this meme with the note “Someone needs to draw you in there with your arm up 🤣🤣🤣” It’s a nice ode to the Dries essay on Maker/Taker problems.

Well, thanks to the magic of AI, I asked the Nano Banana AI Studio to “make it so on the bottom one person raises their hand,” and it didn’t work at first. So, I tried a few other variations, and then, voilà!

Technology is amazing. And now we have a counter to the meme. Be that one hand that raises.

Although this is a joke, I’m going to give humanity a high-five because, compared to when I started in technology, which was more the Microsoft Halloween memo era, to where we are today, I’m so impressed that so many makers, creators, designers, engineers, and leaders have adopted the moral framework of open source being part of their calling. Businesses, too! I used to get laughed out of the room or had spears thrown at the security of open source, but that is no longer a blocker, and the conversation has really elevated. It doesn’t feel like one person raising their hand anymore; it’s grown into a truly special movement, a lens through which you can view almost anything.

Open source is the best way we have to set the foundation for future generations to build upon, ensuring the light cone of humanity’s technological expansion becomes something that belongs to all of us, not just a few.

There are many levels to the excellent Scott Alexander satire of God, Iblis (Islamic word for devil), and Dwarkesh Patel, one of the best new podcasters of this era.

There are people who have gone their whole lives without realizing that Twinkle Twinkle Little Star, Baa Baa Black Sheep, and the ABC Song are all the same tune […]

If they’re used to stories about surgeons getting completed with the string “man”, then that’s the direction their thoughts will always go… Also, how come God can’t make humans speak normally? Everything they say is full of these um dashes!

Which leads to a hat tip to Brian Gardner on the incredible McSweeney’s Em dash responding to the the AI allegations.

So next time you read something and think, “AI wrote this—it has a lot of em dashes,” ask yourself: Is it AI? Or is it just a poet trying to give you vertigo in four lines or fewer?

Summer WordPress Update

AI, Automattic, Open Source, Review, Video, WordCamp, WordPress

I’m still buzzing from an incredible WordCamp US this week, from contributor day to the closing party the vibes were right and it was amazing to connect with fellow travelers in the journey towards creating a more free and open source internet.

Before our open town hall Q&A I was able to make some fun announcements:

  • Traffic to WordPress.org is up, and we’ve brought the plugin queue from months to basically a few days.
  • Previewed Block Comments and the upcoming Command Palette feature in 6.9.
  • Shared some fun AI experiments, including Felix’s AI chatbot demo, Automattic’s new Telex block creator, and more.
  • Got to announce details for the next two flagships:
    • WordCamp Asia 2026: Mumbai, India, from April 9th to 11th.
    • WordCamp Europe 2026: Kraków, Poland. June 4th to 6th 2026.
    • WordCamp US 2026: Phoenix, Arizona, from August 16th to 19th. 😅

Give it a watch!

Think Different

AI, Open Source, Tech, WordCamp, WordPress

Pretty heads down at WordCamp US, which has had amazing energy and talks so far. I wanted to take a moment to note two things, first being a great essay from Dave Winer asking people to Think Different about WordPress.

I’ve done this before — asked people to think differently about things, like public writing, with blogging. In the 90s I was running around the Vallley trying to explain to everyone that blogging was going to change everything, all I got was blank stares from people who said “we don’t do that.” They of course eventually did do it. But at first the ideas seemed foreign, unreasonable.

And in light of the news of Typepad shutting down, note that WordPress has a Typepad importer. A big advantage of putting your content into an open source platform like WordPress with an active community, vs just static pages or something custom, is that you’re getting constant upgrades “for free” as we maintain and iterate on the software, enabling new APIs or things like allowing your AI to talk to your site.

WordPress is built by a community of people deeply passionate about backwards and forward compatibility, radical openness so it’s easy to get things in and out of it, and relentless iteration building for the long term. Despite literally billions of dollars spent trying to kill or crush WordPress, and frequent proclamations of its death, we keep trucking along and doing our darndest to make the web a bit more open and free every day. It’s a life mission of many people, including myself.

The Future of WordPress and AI at WCUS

AI, Automattic, Open Source, Tech, WordCamp, WordPress

The presentations for WordCamp US are just a few days away! We have some really exciting keynotes including Danny Sullivan from Google, John Maeda from Microsoft AI, and Adam Gazzaley (one of the top neuroscientists in the world) from UCSF. I think being in the room and able to meet the speakers and ask questions is even more valuable this year, as things are changing so quickly. If you know anyone in or near Portland, Oregon have them get a ticket! Here are all the other AI-related talks: