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

Luke and Jonathan recap Season 9 of Crossword, preview Season 10, and share their thoughts on what they’re looking forward to over the next 6 months of WordPress. No cricket is discussed, but a recurring pun does make an appearance.

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.