Crossword

Perspectives with Zach Stepek

Crossword

Show Notes

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 team. They debate the current state of WordPress, dark patterns, and what the future might hold for WooCommerce. Oh, and an attempt is made at a cricket reference.

More from Crossword

Oct 23, 2026

Nate Stewart joins Luke and Jonathan to discuss chickens, gambling, commercialized addiction, skill atrophy, taste, GeoCities, and how Automattic, WP Engine, and the WordPress community might work together in a way that would make everyone happy. Nate share his perspective on an unsuccessful retirement and advocates for more organizational diversity in the AI ecosystem. Nate also checks off his bingo card while Jonathan and Luke realize, again, that they're getting old.

Oct 21, 2026

Luke and Jonathan discuss the value Apple places on accessibility in comparison to WordPress and the mission of the WordPress project. Luke attempts to steelman Matt's position on the accessibility team and Jonathan takes a contrarian position.

Sep 10, 2026

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.

Aug 5, 2026

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 question thirty minutes in and pulls the thread one more time. Luke complains about kids on e-bikes and appreciates a stretched metaphor.

Jul 31, 2026

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.

See all episodes →