

Crossword
Jonathan Wold & Luke Carbis
Perspectives on WordPress and the Open Web.
Episodes
Mentioned books

Jun 5, 2025 • 15min
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 Jonathan shares his usual offering of optimism for what might come about at WordCamp Europe.

Jun 4, 2025 • 1h 2min
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 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.

May 29, 2025 • 15min
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.

9 snips
May 23, 2025 • 15min
A Year After
The hosts delve into the ideals of the Open Web, sharing personal insights from their WordCamp experiences. Luke expresses his concerns about Basel while discussing hopes for WordCamp US, including its organizational challenges post-Automattic. They explore cultural perspectives, particularly the differences between American and European views on safety within communities. Anticipation builds for WordCamp US as they discuss accessibility, in-person connections, and their wish for humor in the keynote speeches.

May 15, 2025 • 15min
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.

8 snips
May 8, 2025 • 15min
Back from Break
The hosts unveil a new season and website beyond WordPress. They reflect on the challenges of introducing sponsors while maintaining transparency and integrity. Exciting updates about WordPress 6.8 take center stage, showcasing its focus on usability and community engagement. The conversation turns to Jubilee, emphasizing reconciliation and the potential for renewal. Lastly, they delve into the complexities of AI in plugin development, raising questions about quality and user experience. Tune in for lively discussions filled with insights!

7 snips
Mar 28, 2025 • 15min
CloudFest
The hosts bring energy from CloudFest, recounting Luke's unexpected stage dive into the spotlight. They dive into the shifting leadership dynamics in the WordPress community, focusing on inclusivity and personal stories that reveal deeper challenges. Their experiences at the conference highlight invaluable networking opportunities and a fresh perspective on industry dynamics. With memorable moments and insights, the discussion leaves listeners eager for what's next.

5 snips
Mar 13, 2025 • 15min
Sabotage?
The discussion kicks off with a light-hearted take on cricket before delving into serious concerns about a prominent figure’s recent actions. Delays in software releases and their strategic reasoning are examined, along with the impact of WP Engine on community dynamics. Tensions rise due to impending legal issues, complicating project integrity. The blend of gratitude for past contributions and anxiety over potential self-sabotage paints a complex picture of leadership and trust within the WordPress ecosystem.

Mar 11, 2025 • 15min
Crossword Century
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.

9 snips
Feb 28, 2025 • 15min
WordCamp Asia, Sponsorships, and Hard Yakka
The conversation kicks off with impressions from WordCamp Asia, notably the event’s surprising lack of drama. The hosts dive into the importance of community contributions and the evolving nature of sponsorship, stressing that companies should engage meaningfully rather than merely providing funds. They introduce the Australian phrase 'hard yakka,' signifying hard work, while discussing innovative web solutions for tradespeople. The chat also touches on a class action lawsuit that’s stirring up sentiments in the WordPress community, hinting at bigger industry shifts.


