Someplace, in an alternate timeline, our beloved WordPress editor never received its most controversial update. In a parallel universe Gutenberg never happened, and the WordPress editor is still "Word in a box". In this episode, Jonathan and Luke consider what life would be like for the poor souls who live there.

What happens to the WordPress community without in-person WordCamps? Jonathan and Luke reflect on their virtual event experiences to-date, and imagine what that experience might look like a year from now.

In a frazzled restart to the show, Luke and Jonathan lament the complexities of podcasting setups, discuss the state of virtual WordCamps and meetups, then discuss the WordPress 5.6 release.

Peter Saint-Andre works on Strategic Partnerships at Mozilla. He shares his perspective on WordPress and what "Open Web" means. We talk about creativity and accessibility, risks and opportunities for both WordPress and the Open Web, the importance of democratizing commerce, and the role of community. Also, Peter shares a personal story about Matt.

We discuss the acquisition of Restrict Content Pro by iThemes, the ecosystems being built by WP Engine, GoDaddy, and Liquid Web, and our sense that no one is doing it well - yet.

WordPress is our go-to tool for building new sites, in part because it doesn't restrict creative expression. Even if that means we can publish horrid designs. In this episode, we discuss the idea of an ugly web, and whether the future of WordPress will make the web more self-same, or even uglier?

Marieke van de Rakt, CEO of Yoast joins the discussion. We talk about Yoast, advertising mistakes, growing a plugin business, and the opportunity for a WordPress "App Store".

We talk about the recent controversy over the WordPress app in iOS. Luke expresses his frustration about Automattic's ownership of the app and we discuss the challenges of contributing to funded "Open Source" projects.

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Ryan Singer, Head of Strategy at Basecamp, joins us to talk about his book, Shape Up. Luke loves the book. Jonathan, apparently, has a "problem" with it. Ryan shares his perspective on WordPress and we discuss how the concept of shaping could work for the WordPress project.