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.

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.