PODCAST · technology
Crossword
by Jonathan Wold & Luke Carbis
Perspectives on WordPress and the Open Web.
Episodes
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Benefit of the Doubt
Luke and Jonathan discuss WordCamp US, the recent leadership change at Automattic, and the implications to the WordPress project. Jonathan works through his naivety and mixes metaphors. Luke makes a swing and a miss on a cricket reference.
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Perspectives with Josepha Haden Chomphosy
Josepha joins Jonathan and Luke to discuss ecosystem thinking, municipal government, influence versus control, potholes, bathrooms, data centers, and AI in WordPress. Josepha shares her perspective on the three things everyone in WordPress wants and her hope for its future. Jonathan asks the easy...
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Bad Poetry
Jonathan and Luke discuss how plugin submissions have changed and recent activity on Trac. Luke opines on mass memory loss and draws a line in the sand. Jonathan learns a new word.
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Perspectives with Mike McAlister
Mike McAlister joins Luke and Jonathan to discuss space, astrophotography, design, naming a good product, transitional phases, nuclear energy, and themes. Mike shares his perspective on product creativity, the crossroads we're at in WordPress, and why he's betting everything on Ollie. Luke…
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Useful
Luke and Jonathan discuss the recent Code for the People documentary, WordCamps, and growth in the WordPress community. Jonathan accepts a challenge for WordCamp US and Luke reflects on values.
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Perspectives with Sé Reed
Sé Reed joins Jonathan and Luke to discuss WordPress contribution, community, dictatorship, leadership, accountability, optimism, exploitation, and what happens next. Sé shares her perspective and the impact that the past few years have had on her experience as a contributor. Jonathan has an "ah...
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Relic of the Past
Jonathan and Luke discuss AI usage in the plugin review queue and the impact of increased submission volume. Luke offers an existential question, Jonathan crosses the line, and Luke asks listeners for input on his idea.
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Perspectives with Amy Kamala
Amy Kamala joins Luke and Jonathan to discuss art, poetry, biology, and how decisions get made in the WordPress project. Amy shares her perspective on the human element in automation, Luke expresses his love for contributors over contributions, and Jonathan offers insight into why he and Luke are...
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Fun & Games
Luke and Jonathan discuss the upcoming WordCamp Europe and their mixed feelings about Matt’s latest appeal. Jonathan expresses a dichotomy he’s trying to work through and Luke expresses his disappointment in Jonathan’s latest work.
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Radical Speed Month
Luke has a change of heart about Matt’s renewed involvement and Jonathan gushes over Desktop Mode. They discuss the Presence API and the new WordPress.org Janitors channel. Jonathan makes a basketball reference that goes over Luke’s head.
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Bridges
Jonathan and Luke are back and kickoff the season with an uncomprehensive recap of recent events. Luke offers his thoughts on Matt’s reemergence into the project and Jonathan offers his take on where the opportunity is for WordPress in the new world of AI.
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Bonus: WordCamp Asia
Luke goes solo to WordCamp Asia and records a bonus episode of Crossword. He narrates his contributor day experience, monologues delightfully through day one and two, and, sadly, avoids all cricket references. A special thanks to Kinsta for sponsoring this episode.
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Finale
Luke and Jonathan bring season 10 to a close. Jonathan attempts to reflect on the Crossword decalogy and Luke isn't having it. They end up talking about AI instead which, of course, was much more interesting.
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Perspectives with Miriam Schwab
Miriam Schwab joins Luke and Jonathan to discuss the Elementor ecosystem, what other product companies can learn from its growth, and how Elementor thinks about its relationship with the wider WordPress project. Luke asks a question about dependency, Jonathan geeks out about ecosystem thinking…
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Newsroom
Jonathan and Luke talk through the upcoming end of the Crossword season. They discuss WP Engine’s new offering and offer their speculations. Luke brings up the new Agent Skills project and steps up onto his soapbox.
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Perspectives with Jonathan Desrosiers
Jonathan and Luke have a chat with Jonathan Desrosiers, WordPress Core Committer and Principle Software Engineer at Bluehost. They discuss a recent episode of Crossword and a preview of Desrosiers's now published blog post. Wold asks for clarity on do-acracy vs meritocracy and the three discuss…
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Big Picture Goals
Luke and Jonathan discuss plugin piracy then segue into the WordPress project’s goals for 2026. Luke has mixed feelings about the AI emphasis and Jonathan resurrects the idea of WordPress as an operating system, to Luke’s chagrin.
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Perspectives with Jeff Paul
Luke and Jonathan catch up with Jeff Paul, VP of Open Source Solutions at Fueled and an active contributor to the WordPress project for the past decade. They discuss Jeff's contribution journey, their shared agency experiences, and thoughts on the upcoming 7.0 release. Luke introduces the concept...
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New Year
Luke kicks off Crossword with a surprise and Jonathan rolls with it. They discuss fresh WordPress drama, the plugin review team’s use (or non-use) of AI, and Luke shares his take on AI in WordPress plugins.
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Perspectives with Rae Morey
Luke and Jonathan enjoy a conversation with Rae Morey, publisher of The Repository. Rae shares her origin story and they discuss the top stories of 2025. Luke expresses his optimism for 2026 and Jonathan asks Rae about the sustainability of The Repository itself. Oh, and AI, of course.
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Perspectives with Tammie Lister
Tammie Lister joins Luke and Jonathan to discuss vibe coding, product thinking, and breaking free from a designer typecast into a reputation for product engineering. They also discuss the importance and relevance of WordPress, themes, and cricket.
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Bonus: Geeking Out
Luke and Jonathan start talking immediately after the previous episode and decide to record again. Luke geeks out about the Notes feature, his experiments with it, and subsequent contribution attempt. Jonathan enjoys the show.
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Six Dot Nine
Luke and Jonathan talk through the WordPress 6.9 update and their highlights. Jonathan attempts to make a point about comparing WordPress updates to other ecosystems and Luke isn’t having it.
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State of the Word
Jonathan and Luke discuss Matt’s keynote and the reversal in their expectations going into the event. They share their surprise at a particular data point and Luke offers a few highlights from his recent experience at Enqueue in Sydney.
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More FAIR
Luke and Jonathan are back from an unplanned break and pick up with Luke’s growing interest in the FAIR project. Jonathan asks questions about how things work and expresses his present, yet softening cynicism. They also talk about the Internet Archive’s new project with Automattic.
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Attribution
Jonathan and Luke discuss the copying of plugins and the history of doing so in the WordPress ecosystem. Jonathan realizes what’s been bothering him about it all and Luke points out the difference between stated and practiced values. They also start to talk AI browsers.
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Epiphany
Luke and Jonathan discuss WooCommerce and the opportunities (and challenges) for newcomers like FluentCart. Luke shares the four things he thinks an ecommerce product needs and Jonathan enjoys Luke’s unexpected breakthrough.
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Dodgy Themes
FAIR 1.0 has been released! Jonathan and Luke discuss the implications of the project, modifying the WordPress admin’s “featured plugins”, and the impact of a federated ecosystem. Luke thinks Jonathan failed the challenge.
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Perspectives with Matt Mullenweg
Jonathan and Luke speak with Matt. Yep, that Matt. They talk about jazz, blogging, photography, and the infuriating, heartbreaking, grey-hair-making drama that’s engulfed the WordPress community over the last year.
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Yorker
Jonathan and Luke discuss their nervousness going in to their recording with Matt Mullenweg. They share the preparation process, the questions they wrestled with, the approach they decided to take, and how the experience went.
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Teleportation
Luke and Jonathan are back for Season 10 of Crossword. They open with a recap of WordCamp US and Matt’s “State of the Word” address. They discuss their approach to guests for the upcoming season, introduce this season’s sponsors, and look ahead to the upcoming WordPress 6.9 release. Shownotes:...
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Finale
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.
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Perspectives with Mary Hubbard
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...
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Perspectives with Sam Sidler
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…
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Options, Not Decisions
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…
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Mad Kings
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…
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Perspectives with John Gruber
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...
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The Formula
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...
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Perspectives with Lesley Sim
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...
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Five for the Future
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...
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Perspectives with Zach Stepek
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...
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Sense of Community
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.
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It’s only FAIR
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.
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That Tracks
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...
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Perspectives with Weston Ruter
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...
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New AI Team
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.
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A Year After
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?
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Bad Manners
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.
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Back from Break
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.
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CloudFest
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.
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ABOUT THIS SHOW
Perspectives on WordPress and the Open Web.
HOSTED BY
Jonathan Wold & Luke Carbis
CATEGORIES
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Frequently Asked Questions
How many episodes does Crossword have?
Crossword currently has 151 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.
What is Crossword about?
Perspectives on WordPress and the Open Web.
How often does Crossword release new episodes?
Crossword publishes regularly with 151 episodes available. Check the episode list for the typical release schedule.
Where can I listen to Crossword?
You can listen to Crossword on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.
Who hosts Crossword?
Crossword is created and hosted by Jonathan Wold & Luke Carbis.
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