Shows
CrosswordNew AI TeamLuke 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.2025-05-2915 min
CrosswordA Year AfterLuke 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?2025-05-2315 min
CrosswordBad MannersLuke 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.2025-05-1615 min
CrosswordBack from BreakWe’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.2025-05-0915 minCrosswordCloudFestThis 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.2025-03-2815 minCrosswordSabotage?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?2025-03-1315 minCrosswordCrossword CenturyJonathan 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.2025-03-1115 minCrosswordWordCamp Asia, Sponsorships, and Hard YakkaLuke 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.2025-02-2815 minCrosswordPolitics, Sentiment, and AlternativesIn 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.2025-02-2115 minCrosswordThe Rise of the RepositoryIn 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.2025-02-1715 minCrosswordInvasion or Innovation?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?2025-02-1114 minCrosswordWordPress TherapyJonathan 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.2025-02-0415 minCrosswordFoundationsFrom 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.2025-01-2415 minCrosswordHedging BetsLuke 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.2025-01-2015 minCrosswordBreaking ToysAutomatic 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.2025-01-1515 minCrosswordBack to Business?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?2025-01-1015 minCrosswordThe Price of CriticismLuke 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?2024-11-2215 minCrosswordCentralization, Governance, and CommercializationWhat 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?2024-11-1415 minCrosswordDe-escalationIs 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.2024-11-0115 minCrosswordIdentity CrisisMatt 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?2024-10-2515 minCrosswordThresholdLuke 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.2024-10-2315 minCrosswordStagesMatt 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.2024-10-1515 minCrosswordProblematticEven 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.2024-10-1115 minCrosswordDepartureJosepha Haden Chomphosy, a leading voice in the WordPress project, has stepped down. Lukesees 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?2024-10-0815 minCrosswordTithe & TaxesWP 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.2024-10-0415 minCrosswordFalloutLuke 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?2024-10-0115 minCrosswordScorched EarthExistential 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.2024-09-2715 minCrosswordExistential ThreatIs 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.2024-09-2615 minCrosswordWordCamp Asia 2024In 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.2024-03-2515 min
CrosswordThe new role of themesIn 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.2023-10-1115 min
CrosswordRepository ConsiderationsIn 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.2023-09-2615 min
CrosswordMullenmuskIn this episode Jonathan and Luke discuss the latest round of #WPDrama after WordPress.com cloned the WordPress.org plugin repository.2023-09-1915 min
CrosswordIntrusive AdsIn this episode Luke and Jonathan disagree on who is to blame for intrusive ads inside of the WordPress admin Dashboard. They also cover some of the best practices and motivations of plugin developers, plus how to stop annoying the users.2023-09-1315 min
CrosswordWordPress SecurityIn this episode Luke and Jonathan explore the complex world of WordPress plugin security and what really happens when a vulnerability is identified. The system could be better, but how do we fix it?2023-09-0515 min
CrosswordGood PluginsIn this episode Joshua Wold fills in for Jonathan, discusses plugins, the value of good design in the onboarding process and what makes a strong product founder. Luke tries to bait him with comments about developer supremacy, but Joshua never took the bait.2023-08-2315 min
CrosswordBest EventsIn this episode Luke and Jonathan discuss their early WordCamp experiences and which is the best of the major WordCamps. They also discuss the latest news about the upcoming WordPress admin interface.2023-08-1515 min
CrosswordOpen Source BusinessIn this episode Luke and Jonathan share their vision for what open source business practices could look like. Jonathan even disagrees with Luke on wage transparency for no apparent reason. 2023-08-0815 min
CrosswordWordPress 6.3Luke and Jonathan talk about the highlights of WordPress 6.3, the steady transformation from blogging platform to operating system and the need for a contributor focused event in similar fashion to Apple's WWDC.2023-08-0215 min
CrosswordWelcome BackLuke and Jonathan break into the new season talking about WordPress hosting, conflicts of interest, the importance of onboarding and the products that do it well (Luke also seems to have no idea what season we are recording).2023-07-2515 min
CrosswordFinaleIn the season final Luke and Jonathan discuss their future as professional e-sports athletes before returning to reality and talking about what happens when your product's functionality comes to the WordPress core.
8 down: while( have_posts() )2023-05-2015 min
CrosswordWordCamp EvolutionIn this episode Luke and Jonathan talk about WordCamps, how they are evolving and how they can foster the development of the WordPress community into the next generation. They also talk about the WordPress/Furry connection and Luke's hidden musical talent.
11 across: Pre-designed layout2023-05-1315 min
CrosswordReminiscingAs WordPress turns 20 Jonathan and Luke reminisce about how WordPress has grown. They also explore the rapid leaps forward we are now experiencing due to AI. If you listen closely, you will also hear Luke get embarrassed by the name of one of his earliest companies.
6 Down: Twenty Twenty-Two was inspired by…2023-05-0415 minCrosswordOpportunities & Ecommerce In today's episode of cynic versus fanboy, (uh, I mean Crossword ) Luke and Jonathan discuss the gap between WooCommerce and Shopify plus the opportunities in the ecosystem.
**10 Across**: Open this on GitHub2023-04-2715 min
CrosswordGuildenbergLuke and Jonathan talk about Guildenberg, why Luke doesn't love the name, WordCamp Asia, and the downside of hosts buying WordPress plugins.
5 Down: Translation, but shorter.2023-04-2115 min
CrosswordEnd of YearLuke and Jonathan talk about cricket, look back at WordPress in 2022, touch on ClassicPress, and look ahead to 2023.
9 Across: Stringify JSON2022-12-2915 min
CrosswordState of the WordLuke and Jonathan talk about remote work, then jump into State of the Word, sharing highlights, exploring Luke's reawakening interest in WordPress, and finding something to disagree on in the end.
3 Down: 5.92022-12-2214 min
CrosswordCharmingLuke and Jonathan discuss a particular update in WordPress 6.1, why we'd like to see more hosting providers, and the voice of WordPress.
7 Across: WCEU22 was in…2022-11-1115 minCrosswordWordPress vs. SvelteKitLuke and Jonathan discuss rebuilding a WordPress web-app as a standalone SaaS using the FKIT stack.
2 Down: A built-in post type
More on FKIT: https://www.youtube.com/watch?v=rFP7rUYtOOg2022-08-0414 minCrosswordFree RidersLuke and Jonathan talk about hosts, free riders, and plugin monetization, then take a sharp turn into murder mysteries in WordPress.
4 Across: Days since the last…
Links:
https://jonathanwold.com/hosts-and-the-free-rider-problem/2022-07-2815 minCrosswordDigital GardeningJonathan and Luke discuss how the “reverse chronological order” orientation of WordPress affected the web, and a “Digital Gardening" metaphor that might help fix it.
1 Down: Home of GiveWP, LearnDash, and RCP
Links:
https://maggieappleton.com/garden-history2022-07-2114 min
CrosswordYesterwebLuke and Jonathan open Season 5 debating nostalgia, discussing the 5 minute install, and announcing an acquisition.
1 Across: Serverless compute
Links:
https://yesterweb.org/2022-07-2115 min
CrosswordClarityIn the last episode of Season 4, Luke and Jonathan discuss Clarity and what a better future might look for ads in the WordPress admin.2022-02-1815 min
CrosswordHappy New YearLuke and Jonathan wax lyrical about broken pipes, skiing, the current state of the WordPress community, and the WordPress 2022 release cycle.2022-02-0215 min
CrosswordState of the Word 2021Luke reflects on the 2021 State of the Word, while Jonathan holidays on a Mexican beach.2021-12-1515 min
CrosswordThe MetaverseLuke and Jonathan talk about the Facebook, the Metaverse, WordPress, and the Open Web. Luke begins to change his mind about Zuckerberg and Facebook.2021-11-0414 min
CrosswordMulti-User EditingForget multi-site, we want multi-user! Luke and Jonathan look beyond the (unfailingly distant) full site editing horizon, toward a day when we can edit a post, nay, design an entire WordPress site collaboratively, contiguously, and concurrently.2021-10-2115 min
CrosswordPerspectives with Aaron GustafsonAaron Gustafson is a Principal Program Manager on the Microsoft Edge team, focused on their work on Progressive Web Apps and developer UX. He's also a spec editor at the W3C and Editor-in-chief of A List Apart. Aaron joins Luke and Jonathan to talk about the Open Web and share his perspective (and some guidance) with the WordPress community.2021-10-1554 min
CrosswordProposals, Pods, and Post TypesJonathan attempts a no-code FSE site build, and Luke is skeptical about FSE landing this year.2021-09-1014 min
CrosswordEarly DaysLuke starts off with a surprise. Then we talk about Andrea Middleton, WordPress acquisitions, and whether we're still in the early days of WordPress.2021-09-0215 min
CrosswordUglyLuke and Jonathan talk about themes, an ugly web, and Gutenberg / Classic Editor reviews.2021-08-2614 min
CrosswordMore AcquisitionsWe're back, baby! Luke and Jonathan discuss the recent Yoast acquisition, and compare it with ACF's new home.2021-08-1715 min
CrosswordTavern BuffetLuke and Jonathan catch up after an unplanned hiatus and jump right into enjoying the WP Tavern buffet.2021-05-0614 min
CrosswordThe WordPress GuyKicking off with Season 4, Jonathan and Luke chat about the new Wix ad campaign. Then, they disagree about the future of comments in WordPress.2021-04-1315 min
CrosswordPerspectives with Andrea MiddletonAndrea Middleton is a Community Organizer for the WordPress project. She shares how she first got involved with WordPress and how she ended up working with Community. We cover WordCamps, Meetups, COVID-19, and what it all might mean for the future of WordPress and the WordPress Community.2021-02-0555 min
CrosswordSinging a Different TuneWe wrap up Season #3 with some poignant reflections, then jump into our favorite topic for the moment: Full Site Editing. Luke changes his mind and Jonathan is looking forward to Season #4.2021-02-0414 min
CrosswordFull Site Editing?Jonathan and Luke discuss the recently published timeline for Full Site Editing, and compare it to the rollout of Gutenberg. Also in this episode: GameStonk and Clubhouse.2021-01-2715 min
CrosswordAn American WebRecent events have called into question our Open Web idealism. Should we have an outlet valve for some of the worst of the web? How should the Web be legislated and policed? Should it be possible to access illegal content? And importantly… what role does Open Source have in all of this?2021-01-1515 min
CrosswordMotivationsWe discuss WordPress.com and their recent announcement of a "website building service." Luke thinks it's a bad idea and questions Automattic's intentions. Jonathan tries to take his Automattic hat off and share his perspective.2021-01-0714 min
CrosswordPerspectives with Kent ByeKent is a philosopher, oral historian, experiential journalist, and the host of the Voices of VR podcast. He joins Luke and Jonathan to chat about WordPress and what the web might look like 10 years from now, reimagining the 2D browser window as a 3D canvas.
You can find Kent Bye on:
VoicesOfVR.com
Twitter
Patreon
2020-12-221h 01
CrosswordThemes AgainIt seems we just can't get away from talking about Full Site Editing. In this episode, Luke and Jonathan announce the first Crossword livestream, as well as theme quirks in Twenty Twenty One and the Customizer.2020-12-1715 min
CrosswordWordPress in SpaceLive coverage of the WordPress 5.6 launch! Luke and Jonathan discuss their willingness to press that Update button, then shift track to explore what it might be like to apply the constraints of time and space to the Web.2020-12-0815 min
CrosswordThemes in Twenty TwentyWe talk about weather and wine, then jump into themes. Why is it still so hard to choose a theme? What are we using for our own projects now? What might themes look like in a year?2020-12-0214 min
CrosswordPerspectives with Francesca MaranoFrancesca leads the WordPress Core Team at Yoast, and is serving as an advisor for the all women / non-binary all-star team behind WordPress 5.6. Francesca shares her WordPress journey thus far, especially in the realm of contributing to core, and we dive into topics such as open-source organizational structures, selfish vs. selfless contributions, gatekeeping or siloing in the project, and her vision for a unified WordPress Admin.2020-11-301h 01
CrosswordJam SessionWe talk about our recent experiences with the Plugin Review Team and postulate about the next 10 years of WordPress and the web.2020-11-2415 min
CrosswordFull Site EditingWe discuss the current state of full site editing and our uncertainty about what happens next. We bring up headless, brainless, and the opportunity for more vertically focused businesses built on WordPress.2020-11-1814 min
CrosswordWhat if Gutenberg never happened?Someplace, in an alternate timeline, our beloved WordPress editor never received its most controversial update. In a parallel universe Gutenberg never happened, and the WordPress editor is still "Word in a box". In this episode, Jonathan and Luke consider what life would be like for the poor souls who live there.2020-11-1015 min
CrosswordVirtually VirtualWhat happens to the WordPress community without in-person WordCamps? Jonathan and Luke reflect on their virtual event experiences to-date, and imagine what that experience might look like a year from now.2020-11-0614 min
CrosswordWarm UpIn a frazzled restart to the show, Luke and Jonathan lament the complexities of podcasting setups, discuss the state of virtual WordCamps and meetups, then discuss the WordPress 5.6 release.2020-10-2814 min
CrosswordPerspectives with Peter Saint-AndrePeter Saint-Andre works on Strategic Partnerships at Mozilla. He shares his perspective on WordPress and what "Open Web" means. We talk about creativity and accessibility, risks and opportunities for both WordPress and the Open Web, the importance of democratizing commerce, and the role of community. Also, Peter shares a personal story about Matt.2020-09-1039 min
CrosswordAcquisitions and EcosystemsWe discuss the acquisition of Restrict Content Pro by iThemes, the ecosystems being built by WP Engine, GoDaddy, and Liquid Web, and our sense that no one is doing it well - yet.2020-09-0714 min
CrosswordBlank CanvasWordPress is our go-to tool for building new sites, in part because it doesn't restrict creative expression. Even if that means we can publish horrid designs. In this episode, we discuss the idea of an ugly web, and whether the future of WordPress will make the web more self-same, or even uglier?2020-09-0115 min
CrosswordPerspectives with Marieke van de RaktMarieke van de Rakt, CEO of Yoast joins the discussion. We talk about Yoast, advertising mistakes, growing a plugin business, and the opportunity for a WordPress "App Store".2020-08-2843 min
CrosswordWordPress™We talk about the recent controversy over the WordPress app in iOS. Luke expresses his frustration about Automattic's ownership of the app and we discuss the challenges of contributing to funded "Open Source" projects.2020-08-2414 min
CrosswordEnforcing Directory “Guidelines”episo2020-08-1715 min
CrosswordPerspectives with Ryan SingerRyan Singer, Head of Strategy at Basecamp, joins us to talk about his book, Shape Up. Luke loves the book. Jonathan, apparently, has a "problem" with it. Ryan shares his perspective on WordPress and we discuss how the concept of shaping could work for the WordPress project.2020-08-1343 min
CrosswordP2 2We discuss our conversation with an upcoming guest, premiering later this week. Then we jump into the release of P2, which we're both excited about, and Luke laments its currently non-public code base.2020-08-1015 min
CrosswordGut PunchMatt Mullenweg's review of the new Unsplash WordPress plugin has made waves. Who doesn't love a little #WPDrama? We skip the licensing issue and instead discuss whether a one-star plugin review is the right way for a leader, and maybe a competitor, to express their concern.2020-08-0314 min
CrosswordHousekeeping
From time to time, we might address a little bit of Crossword meta. A quick update from us on getting in touch and the fifteen minute limit.
2020-07-2803 min
CrosswordAdvertising in the Block Directory
We discuss retargeted advertising, whether or not it should exist, and the implications of the current directory guidelines on innovation in the Block Directory.
2020-07-2814 min
CrosswordHamilton’s Open WebEPZ2020-07-2114 min
CrosswordKids, Jetpack, and WeChat
What's the equivalent of TikTok in the WordPress world? We discuss WordPress as the go-to publishing tool for creativity, and compare Jetpack's sordid privacy record with Chinese social media.
2020-07-1314 min
CrosswordGoogle and WordPress
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.
2020-07-0715 min
CrosswordA Design System for WordPress
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.
2020-06-3015 min
CrosswordWWDC and the Plugin Repository
Season #2 premier - episodes now 15 minutes long! We jump straight into a discussion of WWDC, Hey.com, and the WordPress plugin directory.
2020-06-2415 min
Crossword
Season Finale
We discuss Season #1 and explore the wide range of topics we're interested in covering in Season #2.
2020-03-3127 min
Crossword
COVID-19, Virtual Events, and Gradients
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.
2020-03-1234 min
CrosswordWP Notify
Jonathan Bossenger joins us to discuss the WP Notify project and better ways of introducing new features in WordPress.
2020-03-1137 min
CrosswordWordCamp Asia and ThemesWe 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.2020-02-1331 min
CrosswordDemocratizing CommerceWe discuss the idea of "Democratizing Commerce" and what it actually means. Also, we're looking forward to WordCamp Asia.2020-02-0617 min
CrosswordThe Block DirectoryWe discuss the upcoming Block Directory for WordPress and the guidelines regarding premium and "freemium" submissions.2020-01-1615 min