The Jukebox Podcast at WP Tavern recently sat down with Elliott Richmond to talk about two decades working with WordPress, his approach to educational content, and an unlikely pizza business built on WordPress tooling.

A self-taught developer, Elliott has been using WordPress since the b2 days more than 20 years ago. He moved from early web projects for bands and agencies into freelance development and experimented with other CMSs before committing to WordPress. Over the years he has contributed code snippets, tutorials, and community resources, and today combines development, teaching, and entrepreneurship.

During the COVID lockdowns, Elliott and his wife launched a local pizza delivery service as a community project. What started as a temporary effort turned into a regular weekend business that now employs staff and is offered as a replicated model to licensees. WordPress powers the whole operation. The stack uses WordPress with WooCommerce and Jetpack plus custom plugins to handle ordering, time slots, delivery radius checks by postcode, and other operational needs.

From that hands-on experience Elliott built Pizza Pilot, a plugin aimed at local food operations. Pizza Pilot provides configurable slot-based ordering, time-based availability, postcode and radius delivery restrictions, and a pro tier of features for licensees. The plugin is flexible enough for many local retail and food models that require scheduled fulfillment and restricted delivery zones.

Elliott also collaborates with Automattic and wordpress.com. Automattic reached out after seeing his videos, leading to an arrangement where he creates videos about wordpress.com features and workflows through 2026. The collaboration gives him early access to features and flexible briefs; he retains creative freedom and can publish on his own YouTube channel while aligning some material with wordpress.com priorities. The relationship is practical: Automattic offers support and access, and Elliott delivers approachable, useful tutorials for users.

His content strategy is focused on education: explaining features, demonstrating how to use them in real workflows, and breaking down technical topics such as templating and developer tools into approachable lessons. He produces both long-form tutorials and short-form spin-offs to reach different audiences and sees creators as filling documentation and learning gaps during a fast-changing period for WordPress, including major releases and AI integration.

Community feedback, especially from YouTube comments, is a key part of how he refines topics and improves explanations. Elliott treats critique as data for iteration rather than as a discouragement.

His production process starts with a brain dump using voice-to-text, followed by AI-assisted polishing to shape a loose script. He records with an iPhone, uses simple lighting and modest studio gear from his music background, and edits in DaVinci Resolve. He balances screen demos and code walkthroughs with visual aids and motion graphics to demystify concepts, and he highlights developer-focused tools like Xdebug when relevant.

Elliott is clear that partnered content does not limit his authenticity. Briefs provide target audiences and themes, but he keeps creative control and prioritizes useful, honest content over promotional spin.

A recurring theme in the conversation is WordPress as glue for diverse businesses. From local gardeners invoicing through WordPress to a pizza operation managing orders and deliveries, the platform can tie together payments, fulfillment, and customer workflows without building a custom system from scratch.

You can find Elliott’s WordPress videos on his channel elliottrichmondwp and his blog at elliottrichmond.co.uk (double L, double T). He plans content into at least the end of 2026 while continuing to develop Pizza Pilot and grow the pizza business.

The episode highlights how deep technical knowledge, community engagement, and a hands-on attitude can create new directions: producing educational content to clarify evolving WordPress features, and turning WordPress skills into a real-world business.

This episode of the Jukebox Podcast (WP Tavern) features Elliott Richmond, a veteran WordPress developer and educator who’s worked with web platforms since the b2 days. Elliott’s career spans freelancing, CMS work, community contributions (including a 2013 advent calendar of code snippets), and a surprising small-business venture: a neighborhood pizza operation powered by WordPress.

Early history and community
Elliott taught himself web development after leaving a design agency that didn’t focus on web work. He experimented with Joomla and Drupal before settling on b2/WordPress. Early involvement in meetups and community projects shaped his approach: he likes solving tricky problems with WordPress and giving back through teaching and shared resources.

A pizza business built on WordPress
During the COVID lockdown Elliott and his wife launched a local pizza delivery business to fill a gap when many restaurants were closed. What began as a temporary project grew into a staffed micro-business with licensees using the same operating model. WordPress is central to the operation: the site uses WooCommerce, Jetpack, and a custom plugin Elliot developed called Pizza Pilot (a freemium plugin with a Pro version bundled for licensees).

Pizza Pilot highlights
– Slot-based ordering with configurable time windows
– Radius-based delivery restrictions driven by postcodes
– Easy switching between delivery and collection modes
The plugin is aimed at bakeries, pop-ups, and other local food businesses that need precise pickup/delivery control and geo-restricted service areas. Elliott has been contacted by people internationally asking to adapt it for different food types and markets.

Collaboration with Automattic and wordpress.com
Automattic reached out through Michelle Frechette and Stacey Carlson to commission videos explaining wordpress.com features and workflows. That initial contact led to an ongoing arrangement: Elliott creates sponsored content aligned with wordpress.com priorities, while retaining editorial control. He also connected with Brit Solata and Jamie Marsland (head of the wordpress.com YouTube channel). Jamie’s “speed challenge” series influenced Elliott’s approach to simplifying complex topics for wider audiences.

Content goals and formats
Elliott produces both long-form educational videos and short-form clips for social platforms. His goals are practical and educational: explain new features, demonstrate how to use them, and show how to implement solutions—especially during a time of rapid WordPress change (major releases, AI tools, evolving developer workflows). Automattic provides briefs and target-audience guidance occasionally, but Elliott remains free to choose topics and critique features openly. He values the community feedback loop—comments help shape future videos and can improve products.

Topics he plans to cover
– How wordpress.com relates to self-hosted WordPress and Studio app workflows
– Developer tooling and features (for example, enabling Xdebug in local environments)
– Making complex concepts accessible (templating, patterns, template parts, AI) using graphics and analogies
– Real-world demos and workflows drawn from his pizza business and other use cases

How he makes content
Elliott’s process adapts per video but follows a pattern:
– Capture raw ideas quickly using voice-to-text
– Use AI to polish those drafts to about 60–70% of a working script
– Script loosely with flashcard-style prompts instead of strict teleprompter recitals
– Record iteratively and refine in editing, using audience feedback to guide future content
He values scripting for clarity while allowing improvisation on camera. Editing is a creative stage he enjoys—comparing it to composing music.

Gear and software
Elliott intentionally keeps his setup accessible: an iPhone as the main camera, DIY diffused lighting, home studio monitors for audio, and DaVinci Resolve for editing and motion graphics (using the paid license for extras but relying largely on the capable free version). His point: teaching clarity and good audio matter more than expensive equipment.

Community, feedback, and motivation
YouTube comments act as a rapid feedback loop—ideas, corrections, and feature requests often come from the community and inform both content and product changes. Elliott enjoys teaching because explaining concepts often reveals better solutions or fresh insights for his own projects.

Business model and future plans
The pizza operation is a license-based model (not a franchise): licensees buy the business model and receive the Pro plugin and support. Elliott is packaging and refining the plugin to let him continue developing while scaling the pizza side. His work with Automattic continues through the year with flexibility to produce independent content as well. Expect videos on wordpress.com features, developer tooling, AI topics, and occasional pizza-related demos that tie back to WordPress workflows (for example, ordering integrations or a dough calculator).

Where to find Elliott
– YouTube: elliottrichmondwp
– Website: elliottrichmond.co.uk (double L, double T)

This episode underscores how WordPress can power unexpected ventures—from community education to local food businesses—and how a mix of long-term experience, product thinking, and accessible content creation can benefit developers, site owners, and creators.