Crossword

Perspectives with Tammie Lister

23 Dec 2025

Contributed by Lukas

Tammie Lister joins Luke and Jonathan to discuss vibe coding, product thinking, and breaking free from a designer typecast into a reputation for produ...

Geeking Out

18 Dec 2025

Contributed by Lukas

Luke and Jonathan start talking immediately after the previous episode and decide to record again. Luke geeks out about the Notes feature, his experim...

Six Dot Nine

17 Dec 2025

Contributed by Lukas

Luke and Jonathan talk through the WordPress 6.9 update and their highlights. Jonathan attempts to make a point about comparing WordPress updates to o...

State of the Word

05 Dec 2025

Contributed by Lukas

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...

More FAIR

04 Dec 2025

Contributed by Lukas

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 t...

Attribution

24 Oct 2025

Contributed by Lukas

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...

Epiphany

17 Oct 2025

Contributed by Lukas

Luke and Jonathan discuss WooCommerce and the opportunities (and challenges) for newcomers like FluentCart. Luke shares the four things he thinks an e...

Dodgy Themes

26 Sep 2025

Contributed by Lukas

FAIR 1.0 has been released! Jonathan and Luke discuss the implications of the project, modifying the WordPress admin’s “featured plugins”, and t...

Perspectives with Matt Mullenweg

26 Sep 2025

Contributed by Lukas

Jonathan and Luke speak with Matt. Yep, that Matt. They talk about jazz, blogging, photography, and the infuriating, heartbreaking, grey-hair-making d...

Yorker

19 Sep 2025

Contributed by Lukas

Jonathan and Luke discuss their nervousness going in to their recording with Matt Mullenweg. They share the preparation process, the questions they wr...

Teleportation

15 Sep 2025

Contributed by Lukas

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 discus...

Finale

08 Aug 2025

Contributed by Lukas

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...

Perspectives with Mary Hubbard

07 Aug 2025

Contributed by Lukas

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 ...

Perspectives with Sam Sidler

31 Jul 2025

Contributed by Lukas

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...

Options, Not Decisions

24 Jul 2025

Contributed by Lukas

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 o...

Mad Kings

16 Jul 2025

Contributed by Lukas

Jonathan and Luke discuss DHH’s recent comments about Matt and their own experiences with gaslighting. They also re-explore their consternation with...

Perspectives with John Gruber

10 Jul 2025

Contributed by Lukas

John Gruber's Dithering podcast with Ben Thompson was the original inspiration for Crossword's 15-minute format. Five years later, John joins Luke a...

The Formula

03 Jul 2025

Contributed by Lukas

Luke and Jonathan talk through Nilay Patel’s recent interview with Matt on Decoder. Luke shares the “formula” he observed in Matt’s responses ...

Perspectives with Lesley Sim

02 Jul 2025

Contributed by Lukas

Jonathan and Luke catch up with Lesley Sim to explore her experience creating products in the WordPress ecosystem, starting with Newsletter Glue, and ...

Five for the Future

25 Jun 2025

Contributed by Lukas

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 p...

Perspectives with Zach Stepek

25 Jun 2025

Contributed by Lukas

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 betw...

Sense of Community

17 Jun 2025

Contributed by Lukas

Luke waxes poetic about WordCamp Brisbane and Jonathan ruminates on the value of continuity in the WordPress community. They discuss Automattic’s re...

It’s only FAIR

16 Jun 2025

Contributed by Lukas

Federated and Independent – that’s the plan. After a brief catchup on Apple news, Jonathan and Luke discuss the FAIR initiative, its implications ...

That Tracks

05 Jun 2025

Contributed by Lukas

Luke and Jonathan discuss Samuel Sidler’s recent coverage of BlackRock’s devaluation of their Automattic investment. Luke gripes about AI art styl...

Perspectives with Weston Ruter

04 Jun 2025

Contributed by Lukas

Luke and Jonathan catch up with a long-time friend and former colleague Weston Ruter to reminisce about their agency days before talking through Westo...

New AI Team

29 May 2025

Contributed by Lukas

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 impac...

A Year After

23 May 2025

Contributed by Lukas

Luke and Jonathan explore Open Web idealism through the lens of their WordCamp experiences. Luke shares his reservations about Basel and they talk thr...

Bad Manners

15 May 2025

Contributed by Lukas

Luke expresses his frustration for AI generated email replies to human reviews of AI generated plugins. We talk through the last episode’s descripti...

Back from Break

08 May 2025

Contributed by Lukas

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...

CloudFest

28 Mar 2025

Contributed by Lukas

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...

Sabotage?

13 Mar 2025

Contributed by Lukas

Matt Mullenweg’s latest actions have Jonathan confused. They discuss Matt’s proposals to slow down releases, his ominous warnings about the future...

Crossword Century

11 Mar 2025

Contributed by Lukas

Jonathan and Luke celebrate the 100th episode of Crossword! Join them as they reminisce about the past five years, revisit some of their favorite mom...

WordCamp Asia, Sponsorships, and Hard Yakka

28 Feb 2025

Contributed by Lukas

Luke and Jonathan discuss the latest news from WordCamp Asia, particularly the absence of any significant controversy at the event. They also talk abo...

Politics, Sentiment, and Alternatives

21 Feb 2025

Contributed by Lukas

In this episode Luke and Jonathan talk about the intersection of politics and WordPress including the recent dismantling of 18F. They also discuss t...

The Rise of the Repository

17 Feb 2025

Contributed by Lukas

In the wake of the current uncertainty in the WordPress community, the repository has become a valuable source of objective reporting that is not foun...

Invasion or Innovation?

11 Feb 2025

Contributed by Lukas

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...

WordPress Therapy

04 Feb 2025

Contributed by Lukas

Jonathan seeks WordPress therapy from Luke, grappling with a growing sense of unease about the state of the project. They discuss the challenges of na...

Foundations

24 Jan 2025

Contributed by Lukas

From Post Status's non-profit transformation to the emergence of the WPCC, the foundations of the WordPress ecosystem are shifting. Maybe. Jonathan an...

Hedging Bets

20 Jan 2025

Contributed by Lukas

Luke asks Jonathan if he has started investing time in other platforms and technologies in light of recent events. Jonathan shares his evolving perspe...

Breaking Toys

15 Jan 2025

Contributed by Lukas

Automatic is reducing its contributions to WordPress core, and Luke suspects it's a strategic move by Matt to exert control. Jonathan explores alterna...

Back to Business?

10 Jan 2025

Contributed by Lukas

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 Word...

The Price of Criticism

22 Nov 2024

Contributed by Lukas

Luke expresses fear of being "canceled" from the WordPress community for criticizing Matt Mullenweg. Jonathan questions the likelihood of such retribu...

Centralization, Governance, and Commercialization

14 Nov 2024

Contributed by Lukas

What does a healthy future look like for WordPress? Luke shares three key takeaways from a WordCamp Sydney hallway track: the importance of centraliz...

De-escalation

31 Oct 2024

Contributed by Lukas

Is the WordPress drama finally winding down? Jonathan senses a de-escalation, but Luke points out there are still some unsettling loose ends. They di...

Identity Crisis

24 Oct 2024

Contributed by Lukas

Matt Mullenweg's actions have sparked an identity crisis within the WordPress community. Luke and Jonathan grapple with the realization that their se...

Threshold

23 Oct 2024

Contributed by Lukas

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 ...

Stages

15 Oct 2024

Contributed by Lukas

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 Jon...

Problemattic

11 Oct 2024

Contributed by Lukas

Even the most optimistic members of the WordPress community are feeling down. In this episode of Crossword, Jonathan and Luke grapple with the emotio...

Departure

08 Oct 2024

Contributed by Lukas

Josepha Haden Chomphosy, a leading voice in the WordPress project, has stepped down. Lukesees this as a canary in the coal mine, but Jonathan remains ...

Tithe & Taxes

04 Oct 2024

Contributed by Lukas

WP Engine mirrored the WordPress.org repository, sparking a conversation about centralization and control. In this episode, Luke and Jonathan d...

Fallout

01 Oct 2024

Contributed by Lukas

Luke and Jonathan discuss the far-reaching consequences of Matt Mullenweg's actions against WordPress Engine. From individual developers to large age...

Scorched Earth

27 Sep 2024

Contributed by Lukas

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,...

Existential Threat

26 Sep 2024

Contributed by Lukas

Is WordPress facing an existential threat? In the premier of Season 7, Luke and Jonathan discuss Matt Mullenweg and WP Engine. They explore the implic...

WordCamp Asia 2024

25 Mar 2024

Contributed by Lukas

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 de...

The new role of themes

11 Oct 2023

Contributed by Lukas

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 ...

Repository Considerations

26 Sep 2023

Contributed by Lukas

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 th...

Mullenmusk

19 Sep 2023

Contributed by Lukas

In this episode Jonathan and Luke discuss the latest round of #WPDrama after WordPress.com cloned the WordPress.org plugin repository.

Intrusive Ads

12 Sep 2023

Contributed by Lukas

In 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 b...

WordPress Security

05 Sep 2023

Contributed by Lukas

In this episode Luke and Jonathan explore the complex world of WordPress plugin security and what really happens when a vulnerability is identified. T...

Good Plugins

23 Aug 2023

Contributed by Lukas

In this episode Joshua Wold fills in for Jonathan, discusses plugins, the value of good design in the onboarding process and what makes a strong produ...

Best Events

15 Aug 2023

Contributed by Lukas

In this episode Luke and Jonathan discuss their early WordCamp experiences and which is the best of the major WordCamps. They also discuss the latest ...

Open Source Business

08 Aug 2023

Contributed by Lukas

In this episode Luke and Jonathan share their vision for what open source business practices could look like. Jonathan even disagrees with Luke on wag...

WordPress 6.3

02 Aug 2023

Contributed by Lukas

Luke and Jonathan talk about the highlights of WordPress 6.3, the steady transformation from blogging platform to operating system and the need for a ...

Welcome Back

24 Jul 2023

Contributed by Lukas

Luke and Jonathan break into the new season talking about WordPress hosting, conflicts of interest, the importance of onboarding and the products that...

Finale

20 May 2023

Contributed by Lukas

In the season final Luke and Jonathan discuss their future as professional e-sports athletes before returning to reality and talking about what happen...

WordCamp Evolution

13 May 2023

Contributed by Lukas

In this episode Luke and Jonathan talk about WordCamps, how they are evolving and how they can foster the development of the WordPress community into ...

Reminiscing

04 May 2023

Contributed by Lukas

As WordPress turns 20 Jonathan and Luke reminisce about how WordPress has grown. They also explore the rapid leaps forward we are now experiencing due...

Opportunities & Ecommerce

27 Apr 2023

Contributed by Lukas

In today's episode of cynic versus fanboy, (uh, I mean Crossword ) Luke and Jonathan discuss the gap between WooCommerce and Shopify plus the opportun...

Guildenberg

21 Apr 2023

Contributed by Lukas

Luke and Jonathan talk about Guildenberg, why Luke doesn't love the name, WordCamp Asia, and the downside of hosts buying WordPress plugins.  5 Down:...

End of Year

29 Dec 2022

Contributed by Lukas

Luke and Jonathan talk about cricket, look back at WordPress in 2022, touch on ClassicPress, and look ahead to 2023. 9 Across: Stringify JSON

State of the Word

22 Dec 2022

Contributed by Lukas

Luke and Jonathan talk about remote work, then jump into State of the Word, sharing highlights, exploring Luke's reawakening interest in WordPress, an...

Charming

11 Nov 2022

Contributed by Lukas

Luke 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: W...

WordPress vs. SvelteKit

03 Aug 2022

Contributed by Lukas

Luke 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:/...

Free Riders

28 Jul 2022

Contributed by Lukas

Luke and Jonathan talk about hosts, free riders, and plugin monetization, then take a sharp turn into murder mysteries in WordPress. 4 Across: Days si...

Digital Gardening

21 Jul 2022

Contributed by Lukas

Jonathan and Luke discuss how the “reverse chronological order” orientation of WordPress affected the web, and a “Digital Gardening" metaphor th...

Yesterweb

21 Jul 2022

Contributed by Lukas

Luke and Jonathan open Season 5 debating nostalgia, discussing the 5 minute install, and announcing an acquisition. 1 Across: Serverless compute Link...

Clarity

18 Feb 2022

Contributed by Lukas

In the last episode of Season 4, Luke and Jonathan discuss Clarity and what a better future might look for ads in the WordPress admin.

Happy New Year

02 Feb 2022

Contributed by Lukas

Luke and Jonathan wax lyrical about broken pipes, skiing, the current state of the WordPress community, and the WordPress 2022 release cycle.

State of the Word 2021

15 Dec 2021

Contributed by Lukas

Luke reflects on the 2021 State of the Word, while Jonathan holidays on a Mexican beach.

The Metaverse

04 Nov 2021

Contributed by Lukas

Luke and Jonathan talk about the Facebook, the Metaverse, WordPress, and the Open Web. Luke begins to change his mind about Zuckerberg and Facebook.

Multi-User Editing

21 Oct 2021

Contributed by Lukas

Forget multi-site, we want multi-user! Luke and Jonathan look beyond the (unfailingly distant) full site editing horizon, toward a day when we can edi...

Perspectives with Aaron Gustafson

15 Oct 2021

Contributed by Lukas

Aaron 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...

Proposals, Pods, and Post Types

10 Sep 2021

Contributed by Lukas

Jonathan attempts a no-code FSE site build, and Luke is skeptical about FSE landing this year.

Early Days

02 Sep 2021

Contributed by Lukas

Luke starts off with a surprise. Then we talk about Andrea Middleton, WordPress acquisitions, and whether we're still in the early days of WordPress.

Ugly

26 Aug 2021

Contributed by Lukas

Luke and Jonathan talk about themes, an ugly web, and Gutenberg / Classic Editor reviews.

More Acquisitions

17 Aug 2021

Contributed by Lukas

We're back, baby! Luke and Jonathan discuss the recent Yoast acquisition, and compare it with ACF's new home.

Tavern Buffet

06 May 2021

Contributed by Lukas

Luke and Jonathan catch up after an unplanned hiatus and jump right into enjoying the WP Tavern buffet.

The WordPress Guy

13 Apr 2021

Contributed by Lukas

Kicking off with Season 4, Jonathan and Luke chat about the new Wix ad campaign. Then, they disagree about the future of comments in WordPress.

Perspectives with Andrea Middleton

05 Feb 2021

Contributed by Lukas

Andrea Middleton is a Community Organizer for the WordPress project. She shares how she first got involved with WordPress and how she ended up working...

Singing a Different Tune

04 Feb 2021

Contributed by Lukas

We 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 Jo...

Full Site Editing?

27 Jan 2021

Contributed by Lukas

Jonathan and Luke discuss the recently published timeline for Full Site Editing, and compare it to the rollout of Gutenberg. Also in this episode: Gam...

An American Web

15 Jan 2021

Contributed by Lukas

Recent 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 ...

Motivations

07 Jan 2021

Contributed by Lukas

We discuss WordPress.com and their recent announcement of a "website building service." Luke thinks it's a bad idea and questions Automattic's intenti...

Perspectives with Kent Bye

22 Dec 2020

Contributed by Lukas

Kent is a philosopher, oral historian, experiential journalist, and the host of the Voices of VR podcast. He joins Luke and Jonathan to chat about Wor...

Themes Again

17 Dec 2020

Contributed by Lukas

It 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 w...

WordPress in Space

08 Dec 2020

Contributed by Lukas

Live coverage of the WordPress 5.6 launch! Luke and Jonathan discuss their willingness to press that Update button, then shift track to explore what i...

Themes in Twenty Twenty

02 Dec 2020

Contributed by Lukas

We 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 mig...

Perspectives with Francesca Marano

30 Nov 2020

Contributed by Lukas

Francesca 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. Fran...

Jam Session

24 Nov 2020

Contributed by Lukas

We talk about our recent experiences with the Plugin Review Team and postulate about the next 10 years of WordPress and the web.

Full Site Editing

18 Nov 2020

Contributed by Lukas

We discuss the current state of full site editing and our uncertainty about what happens next. We bring up headless, brainless, and the opportunity fo...