
Crossword
Perspectives on WordPress and the Open Web.
Latest episodes

7 snips
Jul 16, 2025 • 15min
Mad Kings
The hosts dive into DHH's provocative remarks about Matt, unpacking feelings of gaslighting and inclusivity in decision-making. They reflect on evolving leadership dynamics within the open-source community, emphasizing the challenges of accountability. Luke shares insights from his work on the Plugins Team, shedding light on their vital role in managing the plugin directory. Finally, they discuss the complexities of plugin review processes, balancing AI efficiency with human oversight to ensure quality and security in software updates.

5 snips
Jul 10, 2025 • 1h 26min
Perspectives with John Gruber
John Gruber, a renowned Apple journalist and the creator of Markdown, joins a deep discussion on the evolution of digital publishing. They explore the contrast between open and closed platforms, sharing insights on the impact of Markdown on writing. John reflects on WordPress's missed opportunities and its enduring appeal. The conversation also navigates the challenges independent creators face, the nostalgic evolution of Internet use, and the future of publishing in a subscription-based world.

12 snips
Jul 3, 2025 • 15min
The Formula
Dive into a captivating discussion about Matt Mullenweg's interview style, complete with playful critiques and spot-on role-playing. Explore the nuances of his responses regarding commercialization in open source and its impact on the WordPress community. Delve into the challenges of ticket sales for WordCamp and the complexities of speaker approvals, shedding light on participation dynamics. Plus, consider the evolving landscape of leadership and governance that could shape the future of WordPress. Get ready for a thought-provoking ride!

12 snips
Jul 2, 2025 • 52min
Perspectives with Lesley Sim
Lesley Sim, a creator in the WordPress ecosystem behind products like Newsletter Glue and EventKoi, shares her entrepreneurial journey. She discusses the challenges of launching Newsletter Glue during the COVID-19 pandemic and the strategic decisions involved in developing EventKoi as an ecosystem plugin. The conversation dives into design philosophies, marketing approaches for different audiences, and the importance of community engagement. Plus, there's a fun tangent into how ultimate frisbee influences clarity in her decision-making.

10 snips
Jun 25, 2025 • 15min
Five for the Future
Dive into the debate over the Five for the Future initiative, where one hosts optimism clashes with another’s skepticism about its real motives. Discover how counting contributions can sometimes lead to disconnection, and the necessity of inclusivity in open source projects. They're also sharing insights on the surprising value of AI-generated content, and how meaningful contributions can significantly bolster careers and business growth. The need for effective recognition in community work is highlighted too, reminding us all of the power of collaboration.

9 snips
Jun 25, 2025 • 58min
Perspectives with Zach Stepek
Zach Stepek and guests explore the fascinating world of WooCommerce, examining its evolution and the challenges it faces in the e-commerce space. They discuss the tension between open-source ideals and monetization, along with WordPress's future. Insights on performance issues, plugin selection, and user experiences shed light on navigating WooCommerce's complexities. The chat even touches on personal anecdotes from music photography and a humorous branding origin story. The mix of technical details and personal stories keeps the conversation lively and engaging.

Jun 17, 2025 • 15min
Sense of Community
The hosts share their heartfelt experiences from WordCamp Brisbane, celebrating community connections among WordPress enthusiasts. They discuss the balance of legacy and innovation, illustrating how new perspectives enrich gatherings. The conversation shifts to Automattic’s acquisition of Clay, hinting at the evolving tech landscape. Finally, they touch on Gravatar's shifting role in online identity, reflecting on its significance for users across platforms.

12 snips
Jun 16, 2025 • 15min
It’s only FAIR
The hosts kick off with a joyful birthday celebration and reflections on key tech events. They dive into the FAIR project, discussing its role in decentralizing WordPress management. An intriguing secret initiative is examined, weighing the benefits of talent against transparency issues. The importance of domain choice, particularly .org, is highlighted, alongside industry leader insights on ownership. Lastly, they address the complexities of managing shared resources in WordPress, tackling challenges like plugin submissions and communication within the community.

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.