Crossword

Luke has a change of heart about Matt’s renewed involvement and Jonathan gushes over Desktop Mode. They discuss the Presence API and the new WordPress.org Janitors channel. Jonathan makes a basketball reference that goes over Luke’s head.

Jonathan and Luke are back and kickoff the season with an uncomprehensive recap of recent events. Luke offers his thoughts on Matt’s reemergence into the project and Jonathan offers his take on where the opportunity is for WordPress in the new world of AI.

Luke goes solo to WordCamp Asia and records a bonus episode of Crossword. He narrates his contributor day experience, monologues delightfully through day one and two, and, sadly, avoids all cricket references. A special thanks to Kinsta for sponsoring this episode.

Luke and Jonathan bring season 10 to a close. Jonathan attempts to reflect on the Crossword decalogy and Luke isn't having it. They end up talking about AI instead which, of course, was much more interesting.

Miriam Schwab joins Luke and Jonathan to discuss the Elementor ecosystem, what other product companies can learn from its growth, and how Elementor thinks about its relationship with the wider WordPress project. Luke asks a question about dependency, Jonathan geeks out about ecosystem thinking, and Miriam welcomes ideas from listeners.

Jonathan and Luke talk through the upcoming end of the Crossword season. They discuss WP Engine’s new offering and offer their speculations. Luke brings up the new Agent Skills project and steps up onto his soapbox.

Jonathan and Luke have a chat with Jonathan Desrosiers, WordPress Core Committer and Principle Software Engineer at Bluehost. They discuss a recent episode of Crossword and a preview of Desrosiers's now published blog post. Wold asks for clarity on do-acracy vs meritocracy and the three discuss the importance of both active and passive contributions. Desrosiers offers his guidance for new contributors.

Luke and Jonathan discuss plugin piracy then segue into the WordPress project’s goals for 2026. Luke has mixed feelings about the AI emphasis and Jonathan resurrects the idea of WordPress as an operating system, to Luke’s chagrin.

Luke and Jonathan catch up with Jeff Paul, VP of Open Source Solutions at Fueled and an active contributor to the WordPress project for the past decade. They discuss Jeff's contribution journey, their shared agency experiences, and thoughts on the upcoming 7.0 release. Luke introduces the concept of cool and dodgy versions of WordPress and Jeff shares guidance for newcomers to contribution.

Luke kicks off Crossword with a surprise and Jonathan rolls with it. They discuss fresh WordPress drama, the plugin review team’s use (or non-use) of AI, and Luke shares his take on AI in WordPress plugins.

Luke and Jonathan enjoy a conversation with Rae Morey, publisher of The Repository. Rae shares her origin story and they discuss the top stories of 2025. Luke expresses his optimism for 2026 and Jonathan asks Rae about the sustainability of The Repository itself. Oh, and AI, of course.

Tammie Lister joins Luke and Jonathan to discuss vibe coding, product thinking, and breaking free from a designer typecast into a reputation for product engineering. They also discuss the importance and relevance of WordPress, themes, and cricket.

Luke and Jonathan start talking immediately after the previous episode and decide to record again. Luke geeks out about the Notes feature, his experiments with it, and subsequent contribution attempt. Jonathan enjoys the show.

Luke and Jonathan talk through the WordPress 6.9 update and their highlights. Jonathan attempts to make a point about comparing WordPress updates to other ecosystems and Luke isn’t having it.

Jonathan and Luke discuss Matt’s keynote and the reversal in their expectations going into the event. They share their surprise at a particular data point and Luke offers a few highlights from his recent experience at Enqueue in Sydney.

Luke and Jonathan are back from an unplanned break and pick up with Luke’s growing interest in the FAIR project. Jonathan asks questions about how things work and expresses his present, yet softening cynicism. They also talk about the Internet Archive’s new project with Automattic.

Jonathan and Luke discuss the copying of plugins and the history of doing so in the WordPress ecosystem. Jonathan realizes what’s been bothering him about it all and Luke points out the difference between stated and practiced values. They also start to talk AI browsers.

Luke and Jonathan discuss WooCommerce and the opportunities (and challenges) for newcomers like FluentCart. Luke shares the four things he thinks an ecommerce product needs and Jonathan enjoys Luke’s unexpected breakthrough.

FAIR 1.0 has been released! Jonathan and Luke discuss the implications of the project, modifying the WordPress admin’s “featured plugins”, and the impact of a federated ecosystem. Luke thinks Jonathan failed the challenge.

Jonathan and Luke speak with Matt. Yep, that Matt. They talk about jazz, blogging, photography, and the infuriating, heartbreaking, grey-hair-making drama that’s engulfed the WordPress community over the last year.

Jonathan and Luke discuss their nervousness going in to their recording with Matt Mullenweg. They share the preparation process, the questions they wrestled with, the approach they decided to take, and how the experience went.

Luke and Jonathan are back for Season 10 of Crossword. They open with a recap of WordCamp US and Matt’s “State of the Word” address. They discuss their approach to guests for the upcoming season, introduce this season’s sponsors, and look ahead to the upcoming WordPress 6.9 release. Shownotes: https://ma.tt/2025/09/wordpresser/ https://www.geoffreylitt.com/2025/09/10/ai-as-teleportation.html

Mary Hubbard is the Executive Director of the WordPress Project and brings a rich background in ecommerce and social media to her self-described work as a product-focused “connector”. Mary joins Luke and Jonathan to discuss the open versus closed web, what the WordPress ecosystem can learn from platforms like TikTok, and the importance of digital literacy in a world of AI. Mary helps Luke make a new connection, Jonathan geeks out about the Art of Gathering, and birds join in from the Australian coast.

Sam Sidler's writing on delta.blog has been a topic of discussion on this season of Crossword. Sam joined Luke and Jonathan to discuss a wide range of topics, from governance and the benevolent dictator model to Five for the Future and the FAIR project, and finally landing on Sam's predictions for the future of WordPress. Multiple puns are worked in, Jonathan and Luke argue about altruism, and Sam reminds everyone that he's not a lawyer.

Luke and Jonathan discuss recent coverage of Crossword and how Luke’s words sound in print. They also discuss the Secure Hosting Alliance and riff on an idea for a new hosting company. Luke expresses his frustration with the complexity of WordPress today and Jonathan wonders if the upcoming 6.9 and 7.0 releases might bring new hope.

Jonathan and Luke discuss DHH’s recent comments about Matt and their own experiences with gaslighting. They also re-explore their consternation with Matt’s “inclusivity” in his decision making. Luke talks about his work on the recently renamed Plugins Team and Jonathan expresses his discomfort with the lack of clear commercial incentives.

John Gruber's Dithering podcast with Ben Thompson was the original inspiration for Crossword's 15-minute format. Five years later, John joins Luke and Jonathan for a wide-ranging conversation covering open versus closed platforms, the history and impact of Markdown, and a missed opportunity in WordPress. Luke goes on about the good old days, Jonathan starts thinking about a rival platform, and John makes a prediction for the ten-year follow-up episode.

Luke and Jonathan talk through Nilay Patel’s recent interview with Matt on Decoder. Luke shares the “formula” he observed in Matt’s responses and Jonathan pushes back on Luke’s assumptions about the “we” in community. They discuss a premium plugin directory, low ticket sales for WordCamp US, and Jonathan attempts a cricket reference.

Jonathan and Luke catch up with Lesley Sim to explore her experience creating products in the WordPress ecosystem, starting with Newsletter Glue, and now EventKoi. They discuss her and Ahmed's approach to building EventKoi as an ecosystem plugin and their thinking about early decisions. Luke reflects on what he found inspiring about their approach to design and Jonathan asks questions about their plans for growing the EventKoi ecosystem. Ultimate Frisbee is also discussed.

Jonathan and Luke discuss Five for the Future in context of a recent chat at WordCamp Europe. Luke shares a refreshingly optimistic take on what the program is and Jonathan shares a surprisingly cynical take on behind-the-scenes motivations. They discuss contribution incentives and the ways that counting to 5% (or any target) can backfire.

Zach Stepek welcomes Luke and Jonathan as guests to do a deep dive into the world of Woo. They discuss the history of WooCommerce and the tension between open-source ideals and monetization. Zach shares highlights from his new role at BigScoots and his perspective from contributing to the hosting team. They debate the current state of WordPress, dark patterns, and what the future might hold for WooCommerce. Oh, and an attempt is made at a cricket reference.

Luke waxes poetic about WordCamp Brisbane and Jonathan ruminates on the value of continuity in the WordPress community. They discuss Automattic’s recent acquisition of Clay and then Luke puts Jonathan on the spot with the WPCC.

Federated and Independent – that’s the plan. After a brief catchup on Apple news, Jonathan and Luke discuss the FAIR initiative, its implications for the plugin directory, and how hosts might contribute to its success.

Luke and Jonathan discuss Samuel Sidler’s recent coverage of BlackRock’s devaluation of their Automattic investment. Luke gripes about AI art styles, zones out once as Jonathan talks about financial incentives, and attempts a joke about Trac. They wrap up by discussing Five for the Future and Jonathan shares his usual offering of optimism for what might come about at WordCamp Europe.

Luke and Jonathan catch up with a long-time friend and former colleague Weston Ruter to reminisce about their agency days before talking through Weston's ten-year tenure as a Core Committer and the legacy of his work on the Customizer. From there, they cover the early days of the WordPress Core Performance Team and Weston's time at Google, culminating in his contributions to the Optimization Detective project. They also discuss AI—how could they not? Weston’s development practices come up too, along with their mostly shared optimism about the future of the Open Web.

Luke doesn’t think there’s much to talk about regarding the new AI team, but Jonathan thinks otherwise. They discuss the team, the potential impact, and Luke’s theory about the actual value of AI in WordPress. They also talk about trust, safety, and emojis.

Luke and Jonathan explore Open Web idealism through the lens of their WordCamp experiences. Luke shares his reservations about Basel and they talk through their hopes (and concerns) for WordCamp US. Also, is WordCamp Brisbane really the best WordCamp?

Luke expresses his frustration for AI generated email replies to human reviews of AI generated plugins. We talk through the last episode’s description evolution—first with AI, now without—and unpack what happens in a world where appreciation seems to be going extinct, right alongside Luke’s sanity.

We’re back with a new season, new website (not on WordPress?!), and two new sponsors. We catch up on news from over the break, including WordPress 6.8, Gravatar, and the Jubilee. Jonathan feels some nerves and Luke complains about AI.

This season finale is the first episode of Crossword to be recorded in person. Jonathan and Luke are recording from CloudFest in Germany. They discuss the highlights of the conference itself, including how Luke jumped up on stage unannounced, meeting Mary Hubbard, and what is coming next.

Matt Mullenweg’s latest actions have Jonathan confused. They discuss Matt’s proposals to slow down releases, his ominous warnings about the future of WordPress, and the unsettling disconnect between his words and actions. Is this a calculated tactic, or a sign of deeper trouble?

Jonathan and Luke celebrate the 100th episode of Crossword! Join them as they reminisce about the past five years, revisit some of their favorite moments and biggest disagreements, and reflect on how much has changed in the WordPress world – and in their own lives.

Luke and Jonathan discuss the latest news from WordCamp Asia, particularly the absence of any significant controversy at the event. They also talk about the importance of community contributions, the need for clear guidelines for sponsorships and explain what hard yakka means for anyone not from Australia.

In this episode Luke and Jonathan talk about the intersection of politics and WordPress including the recent dismantling of 18F. They also discuss the WordPress Sentiment Analysis Report and the WordPress alternatives that they have been dabbling with.

In the wake of the current uncertainty in the WordPress community, the repository has become a valuable source of objective reporting that is not found elsewhere. Jonathan and Luke discuss the importance of independent journalism, the challenges of covering a complex and emotionally charged conflict, and the vital role the repository plays in holding powerful figures accountable.

The WordPress plugin repository is seeing an influx of AI-generated plugins, and Luke is on the front lines. He and Jonathan discuss the challenges of reviewing AI-generated code, and the potential implications for the future of the plugin repo. Is this a threat to the ecosystem, or a sign of exciting new possibilities?

Jonathan seeks WordPress therapy from Luke, grappling with a growing sense of unease about the state of the project. They discuss the challenges of navigating a rapidly changing landscape, the importance of finding opportunities amidst the chaos, and the need for honest conversations about the future of WordPress.

From Post Status's non-profit transformation to the emergence of the WPCC, the foundations of the WordPress ecosystem are shifting. Maybe. Jonathan and Luke discuss the potential for positive change, or further fragmentation.

Luke asks Jonathan if he has started investing time in other platforms and technologies in light of recent events. Jonathan shares his evolving perspective on WordPress and the open web. They also grapple with quantifying the real-world impact of this series of events.

Automatic is reducing its contributions to WordPress core, and Luke suspects it's a strategic move by Matt to exert control. Jonathan explores alternative interpretations, but both agree that this action carries significant risks for the future of the project.