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.

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 rants about Google. Then we talk about the recent history between WordPress and Google and what we both think about their involvement in the WordPress project.

We discuss some proposed changes to the WooCommerce Dashboard design, the trend for WordPress plugins to embrace their own design language (separate to the WP Admin), and the idea of creating a Design System for WordPress.

Season #2 premier - episodes now 15 minutes long! We jump straight into a discussion of WWDC, Hey.com, and the WordPress plugin directory.

We discuss Season #1 and explore the wide range of topics we're interested in covering in Season #2.

We discuss COVID-19 (and how Luke was wrong), the opportunity for virtual events, the recent introduction of full screen editing on by default in WordPress 5.4, and gradients in Gutenberg.

Jonathan Bossenger joins us to discuss the WP Notify project and better ways of introducing new features in WordPress.

We discuss the cancellation of WordCamp Asia and then, to happier matters, the first "Future of Themes" meeting, including what an easier-to-use WordPress means for the builder ecosystem.

We discuss the idea of "Democratizing Commerce" and what it actually means. Also, we're looking forward to WordCamp Asia.

We discuss the upcoming Block Directory for WordPress and the guidelines regarding premium and "freemium" submissions.

We discuss the "WP Notify" proposal and the impact of notifications through the lens of WordPress as an Operating System.

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 discuss ecosystems and marketplaces in WordPress, looking back on 2019 and ahead to 2020. Where are the opportunities? What might it mean for the Open Web?

We discuss Gutenberg and the future of WordPress themes with Rich Tabor.

A review of the WordPress Core projects scheduled for 2019 and a discussion of what's to come in 2020.

"Black Friday" offers a chance to discuss ads in WordPress and what improving the experience might look like.

Our Pilot episode, covering the WordPress 5.3 "Kirk" release.

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 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 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.

Crossword returns for Season 8. Jonathan and Luke catch up after the holiday break, review the news, and decide not to talk about cricket. Is the WordPress community finally getting back to business, or are there more surprises in store?

Luke expresses fear of being "canceled" from the WordPress community for criticizing Matt Mullenweg. Jonathan questions the likelihood of such retribution, but Luke points to the banning of Ryan McCue and others as evidence of Matt's willingness to silence dissent. Is there a price to pay for speaking truth  to power in the WordPress world?

What does a healthy future look like for WordPress? Luke shares three key takeaways from a WordCamp Sydney hallway track: the importance of centralization, the need for better governance, and the potential benefits of commercializing WordPress.org. Do Jonathan and the wider community agree?

Is the WordPress drama finally winding down? Jonathan senses a de-escalation, but Luke points out there are still some unsettling loose ends. They discuss new data on WordPress growth, the departure of more plugins from WordPress.org, and the lingering questions about the future of the project.

Matt Mullenweg's actions have sparked an identity crisis within the WordPress community. Luke and Jonathan grapple with the realization that their sense of belonging and purpose is intertwined with a project that might be slipping away. Can they find a way to reconcile their personal investments with the unsettling reality of WordPress today?

Luke has reached a point of acceptance about the future of WordPress, but that doesn't mean he's giving up. Join the conversation as he and Jonathan explore the different paths forward, from Matt Mullenweg's potential departure to the emergence of a more unified and empowered community.

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.

Matt Mullenweg’s actions over the past few weeks raises a fundamental question: What does success look like for an open-source project? Luke and Jonathan discuss the weekends’ events, ask more questions than they answer, and work through the stages of grief.

Even the most optimistic members of the WordPress community are feeling down. In this episode of Crossword, Jonathan and Luke grapple with the emotional weight of Matt Mullenweg's actions, including a bizarre new login requirement on WordPress.org, and question whether a "war" is truly the best path forward.

Josepha Haden Chomphosy, a leading voice in the WordPress project, has stepped down. Luke
sees this as a canary in the coal mine, but Jonathan remains optimistic that there are better times ahead. Can Matt turn it around or is this the beginning of a mass exodus?

WP Engine mirrored the WordPress.org repository, sparking a conversation about centralization and control. In this episode, Luke and Jonathan discuss the technicalities of mirroring, the potential for fragmentation, and whether Matt Mullenweg's invitation for others to "step up" is sincere.

Luke and Jonathan discuss the far-reaching consequences of Matt Mullenweg's actions against WordPress Engine. From individual developers to large agencies, they examine how this conflict impacts the livelihoods of those deeply embedded in the WordPress ecosystem. Is this the kind of leadership WordPress needs going forward?

Existential wasn't hyperbole. In this episode, Luke and Jonathan react to the breaking news of WordPress.org cutting off access to WP Engine servers, effectively crippling over a million websites. They unpack the potential motivations and ramifications of this unprecedented move by Matt Mullenweg.

Is WordPress facing an existential threat? In the premier of Season 7, Luke and Jonathan discuss Matt Mullenweg and WP Engine. They explore the implications of Matt’s recent actions, whether or not the benefit of the doubt applies, and the ramifications to the broader community.

In this episode Jonathan and Luke reflect on their experience at WordCamp Asia, explore Luke's vision for the Plugin Review Team and how to improve developer relations in the WordPress community.

In this episode, Luke and Jonathan discuss the role of WordPress themes in 2023, how block themes and the Full Site Editor have changed the landscape and where the line between themes and plug-ins should be. They also reflect on their current projects.

In this episode Luke and Jonathan talk about the ramifications of cloning the WordPress Plugin repository onto WordPress.com. How to do it in a way that keeps plugin developers onside, and as a bonus, Jonathan read the whole Terms of Service so you don't have to.

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.