Within WordPress

In this episode of Within WordPress, I sit down with Rodolfo Melogli to talk about his path from growing Business Bloomer into one of the best-known WooCommerce resources to now launching Checkout Summit, a dedicated in-person WooCommerce conference in Palermo, Sicily, on April 23–24, 2026



After years without a WooCommerce-focused event since WooConf 2017, Checkout Summit feels like a big moment. Rodolfo explains why now is the right time, how AI has changed content-led growth, and why he is betting on something far more human: personal brand, real relationships, and community.



We dig into the thinking behind the event, from its intentionally small size of just 150 attendees to the 12 carefully selected WooCommerce talks, practical breakout sessions, and all-inclusive format designed to keep people together and conversations flowing. The goal is simple: less conference chaos, more meaningful connections, better conversations, and real business outcomes.



If you care about WooCommerce, events, community, and where growth is heading next, this episode is for you. There are still some tickets left at checkoutsummit.com.



00:00 Podcast Welcome Guest
00:54 WooCommerce Origins 2011
01:42 Choosing Ecommerce Platforms
02:50 From Rome To Ireland
04:05 Life In Sicily Food Heat
06:12 Roman Identity Accents
07:37 International Clients Only
11:14 Italy Business Reality
14:57 WooCommerce Fork Story
15:55 Why WooCommerce Clicked
18:24 Blog Snippets Take Off
20:08 AI Changes Content Game
22:50 Viral Tech Fix Post
24:07 Why Sicily Summit
25:28 WooCommerce Events Gap
27:05 Small Conference Vibe
32:35 Building In Public
36:39 Unique Event Format
43:00 Tickets And Timing
45:01 Speaker Selection Strategy
49:21 Wrap Up And Links

Chapters

(00:00:00) - WooCommerce Guru
(00:02:49) - Wonders of the World
(00:06:11) - Do Italians Have A Roman Accent?
(00:07:37) - Is it time to start doing business locally in Sicily?
(00:13:43) - WooCommerce vs. Woocommerce: How Did You Choose
(00:20:39) - How to Make a Living on WordPress for 12 Years
(00:23:52) - WooCommerce: Bringing Human Connections back
(00:33:15) - Posting on Medium
(00:35:23) - Ideas for a Word Camp
(00:36:11) - What's the Conference's PRIDE?
(00:43:13) - Tickets still available for the Summer Games
(00:45:01) - WooCommerce Conference

In this episode of Within WordPress, I talk with Jason “JK” Konen of WP Engine about Newsroom, a WordPress-based publishing platform built for large editorial teams.

We explore what makes high-volume newsrooms different from typical blogs, where WordPress workflows start to break down at scale, and how Newsroom aims to solve those problems. JK explains how the platform gives different team members, from editors to SEO specialists to media teams, the tools they need without forcing everyone into the same interface.

We also talk about collaboration, publishing guardrails, and the role of checklists in helping teams meet editorial and accessibility requirements before anything goes live. That includes practical AI-assisted features, such as helping generate alt text, with a focus on supporting workflows rather than replacing journalism.

JK shares how Newsroom grew out of work with UK agency Big Bite in late 2023, and why WP Engine sees it as a way to help publishers move away from patched-together processes and toward a more structured, scalable editorial workflow.

00:00 Welcome and Guest Intro
01:06 Jason’s Tech Journey
03:28 What Is Newsroom
06:32 Why Build This Suite
09:58 Who It’s For
11:45 Agency Pain and Foundation
14:36 Role Based Interfaces
22:37 Workflow Guardrails
25:50 AI Assist Not Replace
29:19 What’s Next With AI
32:17 AI and Content Data
37:58 Daily Topic Suggestions
42:01 Experiment Fast Mindset
42:31 Beyond Generative AI
43:07 AI Imagery Feels Off
45:26 Visual Aids With Napkin
46:37 AI Wild West Phase
49:28 Rethinking Publishing Strategy
50:54 Newsroom Feature Highlights
52:57 Collaboration Mode Philosophy
56:11 How To Get A Demo
59:18 Meet Jason Conan
01:01:40 What Newsroom Solves
01:08:41 Building For Enterprise Teams
15:32 Role Based Interfaces
18:09 SEO As Separate Job
21:38 Workflow Guardrails
01:20:59 SEO Checklist Wins
01:23:03 Accessibility Before Publish
01:24:01 Building With AI
01:28:13 Agentic Search Future
01:30:38 Data Driven Suggestions
01:36:09 Daily Topic Briefings
01:41:46 Practical AI Uses
01:48:20 Newsroom Feature Highlights
01:51:42 Collaboration When Needed
01:54:23 Get a Demo
01:55:04 Closing Thoughts

Chapters

(00:00:00) - Within WordPress
(00:00:55) - Meet WP Engine's Product Manager Jason Conan
(00:03:31) - Newsroom: A Collection of Things for Publishers
(00:10:12) - Looking for large-scale content teams in WordPress
(00:15:32) - How to Manage a Newsroom with SEO, Editing and News
(00:17:57) - How to Collaborate in a Content Production Organization
(00:25:50) - In the Elevator With AI in Newsroom
(00:29:19) - What would be the proudest thing you've built in there?
(00:37:59) - Grok: Now's the Time to Innovate
(00:44:47) - Canva's AI-powered Images
(00:50:08) - Top Five Features of WP Newsroom
(00:55:32) - How WPEngine can help your newsroom

In this episode of Within WordPress, we sit down with Carole (CloudFest) and Mark Weisbord (CEO of Greyd) to explain what is changing at CloudFest this year, and why it matters for agencies and WordPress businesses.

The headline is the launch of the WordPress Business and Agency Summit on the Monday before the main CloudFest event. We position it as a connector between the CloudFest Hackathon and the main CloudFest conference, and as a deliberate step toward giving agencies and WordPress businesses a more relevant, more pragmatic, more commercially useful program than the traditional “WordPress Day” format.

We unpack the difference between WordCamps and CloudFest. WordCamps remain community-first, volunteer-driven, and primarily focused on education and connection inside the WordPress community. CloudFest is a for-profit, cloud and hosting industry conference with a very different scale, structure, and mission, and it can build a dedicated business-focused layer around WordPress without trying to turn WordCamps into something they were never designed to be.

This year’s Summit expands the former WP Day into a full-day, two-track program, adds an exhibition area, and targets roughly 800 attendees in a more intimate setting inside a much larger 10,000+ person event. From Mark’s perspective, if we want growth and new partnerships, we need to attract agencies outside the WordPress community, and we need content that connects to direct business impact. That means talks about sales, pricing, go-to-market, agency operations, maintenance revenue, and what it really takes to move from agency work into becoming a product company.

We also talk about the CloudFest Hackathon as a uniquely valuable environment for multi-day collaboration and deeper conversations that rarely happen at faster-paced conferences. Carole connects that to a broader goal: cross-CMS collaboration and strengthening the open web, so we do not end up with a future where a handful of platforms dictate where and how people can publish.

We close with practical attendance advice, a reality check that the Hackathon is already fully booked, and the key dates for the Summit and the main CloudFest event.

00:00 – Cold open: editing workflow and “wave” marker for cuts
00:01 – Welcome and setup: two guests, and why this episode is different
00:02 – Carole: WordPress community background and CloudFest involvement
00:03 – What CloudFest is: scale, audience, and Europa-Park as the venue
00:04 – “Everything is different this year”: why we are doing this episode
00:05 – The new WordPress Business and Agency Summit: where it fits in the week
00:06 – Mark Weisbord (Greyd): the missing business layer in WordPress events
00:07 – From “WP Day” to a bigger Summit: what changes operationally
00:08 – Two tracks, full day, and a dedicated exhibition area
00:09 – Why this format matters: connecting agencies, partners, and real-world solutions
00:11 – WordCamps vs CloudFest: why they serve different purposes
00:12 – Sponsor reality: ROI pressure, leads, and reaching agencies outside the bubble
00:13 – Content shift: business impact over general tech presentations
00:14 – WordCamps still matter, but they are not the vehicle for everything
00:16 – Biggest change: bring in agencies outside WordPress, plus an entertainment factor
00:18 – CloudFest vibe: opening party, Lords of the Uptime, and the venue experience
00:23 – Practical advice: stay multiple nights for Summit welcome + opening party
00:25 – Hackathon value: multi-day conversations and real collaboration time
00:28 – Hackathon evolution: cross-CMS collaboration and protecting the open web
00:33 – Why agencies benefit: broader ecosystem exposure than a WordCamp context
00:36 – What the Summit covers: sales, pricing, playbooks, productizing, maintenance
00:40 – How Summit pillars extend into t...

Chapters

(00:00:00) - Within WordPress: A Special Episode
(00:01:22) - A Word about Cloud Fest
(00:04:25) - Building the Business Side of WordCamp
(00:10:08) - Cloudfest: The Business of WordCamp
(00:17:22) - Entertainment at Cloud Fest 2018
(00:24:22) - Bill Gates at the Hackathon
(00:34:38) - Wonders of the Web: Business and Topics
(00:38:10) - Cloudfest 2020: A day for agencies?
(00:41:10) - Wonders of the Web: Education and Business
(00:44:31) - WordCamp Europe: A 10,000-Person Event
(00:47:33) - Cloud Fest 2018: The Hackathon
(00:50:29) - Cloudflare

Welcome to 'Within WordPress,' where we dive deep with special guest Jono Alderson. Join us as Jono shares his fascinating journey from a bedroom web developer to a leading figure in the WordPress community.



He talks about the early days of technical SEO, the frustrations with homegrown CMS, and why WordPress became his tool of choice. We discuss the current landscape of the web, the rise of JavaScript frameworks, and the role AI can play in optimizing websites.



Jono also gives insights into his work with Yoast, the challenges of implementing good web standards, and why he believes sites built with JavaScript alone often fall short.



Tune in for an engaging conversation full of insights and practical advice for WordPress developers and enthusiasts.

In this episode, we dive into the world of WordPress with Elliott Richmond, a seasoned web developer who has been crafting websites for over 20 years. Elliot discusses his journey, from becoming a developer to running his software company with his wife, Rachel.

We also explore his passion for teaching WordPress through YouTube and how he balances it with his unique side hustle: running a pizza delivery business.

Learn how Elliot marries his coding skills with entrepreneurship and community engagement, offering a comprehensive view of his multifaceted career.

00:00 Introduction and Guest Welcome
00:38 Elliot's Background and Experience
02:52 YouTube and Teaching WordPress
05:17 Balancing Creativity and Technical Skills
13:50 AI in Development and Content Creation
27:14 The Impact of Technology on Social Interactions
28:16 Balancing Work and Personal Life
28:43 The Evolution of a Software Business
31:10 Challenges and Benefits of Full Site Editing
40:18 The Pizza Business Journey
43:46 Mediterranean Influences and Culinary Passion
48:12 Licensing and Expanding the Pizza Business
53:28 Conclusion and Future Plans

Chapters

(00:00:00) - Within WordPress: Elliot Richmond's Story
(00:02:53) - Teaching WordPress on YouTube
(00:07:03) - Mr. Beast on His Videos
(00:12:50) - The Challenges of Building a Computer
(00:13:08) - How Do You Explain Yourself in a Video?
(00:21:26) - Side Project: Playing with AI in WordPress
(00:28:15) - Married professionals: The types of jobs that they do
(00:31:11) - Full-Site Editing in WordPress
(00:40:18) - How I Went From Being a Website Creator to a Pizza Baker
(00:47:11) - "It's not for me"
(00:48:15) - How to start a pizza business with a side hustle
(00:49:37) - Pizza Business