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.