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.