Best Jonathan Wold Podcasts (2025)

1
Mad Kings 15:00

Play Pause

6d ago15:00

15:00

Jonathan and Luke discuss DHH’s recent comments about Matt and their own experiences with gaslighting. They also re-explore their consternation with Matt’s “inclusivity” in his decision making. Luke talks about his work on the recently renamed Plugins Team and Jonathan expresses his discomfort with the lack of clear commercial incentives.…

1
Perspectives with John Gruber 1:26:27

12d ago1:26:27

1:26:27

John Gruber's Dithering podcast with Ben Thompson was the original inspiration for Crossword's 15-minute format. Five years later, John joins Luke and Jonathan for a wide-ranging conversation covering open versus closed platforms, the history and impact of Markdown, and a missed opportunity in WordPress. Luke goes on about the good old days, Jonath…

1
The Formula 15:00

19d ago15:00

15:00

Luke and Jonathan talk through Nilay Patel’s recent interview with Matt on Decoder. Luke shares the “formula” he observed in Matt’s responses and Jonathan pushes back on Luke’s assumptions about the “we” in community. They discuss a premium plugin directory, low ticket sales for WordCamp US, and Jonathan attempts a cricket reference.…

1
Perspectives with Lesley Sim 51:37

20d ago51:37

51:37

Jonathan and Luke catch up with Lesley Sim to explore her experience creating products in the WordPress ecosystem, starting with Newsletter Glue, and now EventKoi. They discuss her and Ahmed's approach to building EventKoi as an ecosystem plugin and their thinking about early decisions. Luke reflects on what he found inspiring about their approach …

1
Five for the Future 15:00

27d ago15:00

15:00

Jonathan and Luke discuss Five for the Future in context of a recent chat at WordCamp Europe. Luke shares a refreshingly optimistic take on what the program is and Jonathan shares a surprisingly cynical take on behind-the-scenes motivations. They discuss contribution incentives and the ways that counting to 5% (or any target) can backfire.…

1
Perspectives with Zach Stepek 58:00

27d ago58:00

58:00

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, da…

1
Sense of Community 15:00

1M ago15:00

15:00

Luke waxes poetic about WordCamp Brisbane and Jonathan ruminates on the value of continuity in the WordPress community. They discuss Automattic’s recent acquisition of Clay and then Luke puts Jonathan on the spot with the WPCC.By Jonathan Wold & Luke Carbis

1
It’s only FAIR 15:00

1M ago15:00

15:00

Federated and Independent – that’s the plan. After a brief catchup on Apple news, Jonathan and Luke discuss the FAIR initiative, its implications for the plugin directory, and how hosts might contribute to its success.By Jonathan Wold & Luke Carbis

1
That Tracks 15:00

2M ago15:00

15:00

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 …

1
Perspectives with Weston Ruter 1:01:47

2M ago1:01:47

1:01:47

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, culminat…

1
New AI Team 15:00

2M ago15:00

15:00

Luke doesn’t think there’s much to talk about regarding the new AI team, but Jonathan thinks otherwise. They discuss the team, the potential impact, and Luke’s theory about the actual value of AI in WordPress. They also talk about trust, safety, and emojis.By Jonathan Wold & Luke Carbis

1
A Year After 15:00

2M ago15:00

15:00

Luke and Jonathan explore Open Web idealism through the lens of their WordCamp experiences. Luke shares his reservations about Basel and they talk through their hopes (and concerns) for WordCamp US. Also, is WordCamp Brisbane really the best WordCamp?By Jonathan Wold & Luke Carbis

1
Bad Manners 15:00

2M ago15:00

15:00

Luke expresses his frustration for AI generated email replies to human reviews of AI generated plugins. We talk through the last episode’s description evolution—first with AI, now without—and unpack what happens in a world where appreciation seems to be going extinct, right alongside Luke’s sanity.By Jonathan Wold & Luke Carbis

1
Back from Break 15:00

2M ago15:00

15:00

We’re back with a new season, new website (not on WordPress?!), and two new sponsors. We catch up on news from over the break, including WordPress 6.8, Gravatar, and the Jubilee. Jonathan feels some nerves and Luke complains about AI.By Jonathan Wold & Luke Carbis

1
CloudFest 15:00

4M ago15:00

15:00

This season finale is the first episode of Crossword to be recorded in person. Jonathan and Luke are recording from CloudFest in Germany. They discuss the highlights of the conference itself, including how Luke jumped up on stage unannounced, meeting Mary Hubbard, and what is coming next.By Jonathan Wold & Luke Carbis

1
Sabotage? 15:00

4M ago15:00

15:00

Matt Mullenweg’s latest actions have Jonathan confused. They discuss Matt’s proposals to slow down releases, his ominous warnings about the future of WordPress, and the unsettling disconnect between his words and actions. Is this a calculated tactic, or a sign of deeper trouble?By Jonathan Wold & Luke Carbis

1
Crossword Century 15:00

4M ago15:00

15:00

Jonathan and Luke celebrate the 100th episode of Crossword! Join them as they reminisce about the past five years, revisit some of their favorite moments and biggest disagreements, and reflect on how much has changed in the WordPress world – and in their own lives.By Jonathan Wold & Luke Carbis

1
WordCamp Asia, Sponsorships, and Hard Yakka 15:00

5M ago15:00

15:00

Luke and Jonathan discuss the latest news from WordCamp Asia, particularly the absence of any significant controversy at the event. They also talk about the importance of community contributions, the need for clear guidelines for sponsorships and explain what hard yakka means for anyone not from Australia.…

1
Politics, Sentiment, and Alternatives 15:00

5M ago15:00

15:00

In this episode Luke and Jonathan talk about the intersection of politics and WordPress including the recent dismantling of 18F. They also discuss the WordPress Sentiment Analysis Report and the WordPress alternatives that they have been dabbling with.By Jonathan Wold & Luke Carbis

1
The Rise of the Repository 15:00

5M ago15:00

15:00

In the wake of the current uncertainty in the WordPress community, the repository has become a valuable source of objective reporting that is not found elsewhere. Jonathan and Luke discuss the importance of independent journalism, the challenges of covering a complex and emotionally charged conflict, and the vital role the repository plays in holdi…

1
Invasion or Innovation? 14:59

5M ago14:59

14:59

The WordPress plugin repository is seeing an influx of AI-generated plugins, and Luke is on the front lines. He and Jonathan discuss the challenges of reviewing AI-generated code, and the potential implications for the future of the plugin repo. Is this a threat to the ecosystem, or a sign of exciting new possibilities?…

1
WordPress Therapy 15:00

6M ago15:00

15:00

Jonathan seeks WordPress therapy from Luke, grappling with a growing sense of unease about the state of the project. They discuss the challenges of navigating a rapidly changing landscape, the importance of finding opportunities amidst the chaos, and the need for honest conversations about the future of WordPress.…

1
Foundations 15:00

6M ago15:00

15:00

From Post Status's non-profit transformation to the emergence of the WPCC, the foundations of the WordPress ecosystem are shifting. Maybe. Jonathan and Luke discuss the potential for positive change, or further fragmentation.By Jonathan Wold & Luke Carbis

1
Hedging Bets 15:00

6M ago15:00

15:00

Luke asks Jonathan if he has started investing time in other platforms and technologies in light of recent events. Jonathan shares his evolving perspective on WordPress and the open web. They also grapple with quantifying the real-world impact of this series of events.By Jonathan Wold & Luke Carbis

1
Breaking Toys 15:00

6M ago15:00

15:00

Automatic is reducing its contributions to WordPress core, and Luke suspects it's a strategic move by Matt to exert control. Jonathan explores alternative interpretations, but both agree that this action carries significant risks for the future of the project.By Jonathan Wold & Luke Carbis

1
Back to Business? 15:00

6M ago15:00

15:00

Crossword returns for Season 8. Jonathan and Luke catch up after the holiday break, review the news, and decide not to talk about cricket. Is the WordPress community finally getting back to business, or are there more surprises in store?By Jonathan Wold & Luke Carbis

1
The Price of Criticism 15:00

8M ago15:00

15:00

Luke expresses fear of being "canceled" from the WordPress community for criticizing Matt Mullenweg. Jonathan questions the likelihood of such retribution, but Luke points to the banning of Ryan McCue and others as evidence of Matt's willingness to silence dissent. Is there a price to pay for speaking truth to power in the WordPress world?…

1
Centralization, Governance, and Commercialization 15:00

8M ago15:00

15:00

What does a healthy future look like for WordPress? Luke shares three key takeaways from a WordCamp Sydney hallway track: the importance of centralization, the need for better governance, and the potential benefits of commercializing WordPress.org. Do Jonathan and the wider community agree?By Jonathan Wold & Luke Carbis

1
De-escalation 15:00

9M ago15:00

15:00

Is the WordPress drama finally winding down? Jonathan senses a de-escalation, but Luke points out there are still some unsettling loose ends. They discuss new data on WordPress growth, the departure of more plugins from WordPress.org, and the lingering questions about the future of the project.By Jonathan Wold & Luke Carbis

1
Identity Crisis 15:00

9M ago15:00

15:00

Matt Mullenweg's actions have sparked an identity crisis within the WordPress community. Luke and Jonathan grapple with the realization that their sense of belonging and purpose is intertwined with a project that might be slipping away. Can they find a way to reconcile their personal investments with the unsettling reality of WordPress today?…

1
Threshold 15:00

9M ago15:00

15:00

Luke has reached a point of acceptance about the future of WordPress, but that doesn't mean he's giving up. Join the conversation as he and Jonathan explore the different paths forward, from Matt Mullenweg's potential departure to the emergence of a more unified and empowered community.By Jonathan Wold & Luke Carbis

1
Stages 15:00

9M ago15:00

15:00

Matt Mullenweg’s actions over the past few weeks raises a fundamental question: What does success look like for an open-source project? Luke and Jonathan discuss the weekends’ events, ask more questions than they answer, and work through the stages of grief.By Jonathan Wold & Luke Carbis

1
Problemattic 15:00

9M ago15:00

15:00

Even the most optimistic members of the WordPress community are feeling down. In this episode of Crossword, Jonathan and Luke grapple with the emotional weight of Matt Mullenweg's actions, including a bizarre new login requirement on WordPress.org, and question whether a "war" is truly the best path forward.…

1
Departure 15:00

10M ago15:00

15:00

Josepha Haden Chomphosy, a leading voice in the WordPress project, has stepped down. Luke sees this as a canary in the coal mine, but Jonathan remains optimistic that there are better times ahead. Can Matt turn it around or is this the beginning of a mass exodus?By Jonathan Wold & Luke Carbis

1
Tithe & Taxes 15:00

10M ago15:00

15:00

WP Engine mirrored the WordPress.org repository, sparking a conversation about centralization and control. In this episode, Luke and Jonathan discuss the technicalities of mirroring, the potential for fragmentation, and whether Matt Mullenweg's invitation for others to "step up" is sincere.By Jonathan Wold & Luke Carbis

1
Fallout 15:00

10M ago15:00

15:00

Luke and Jonathan discuss the far-reaching consequences of Matt Mullenweg's actions against WordPress Engine. From individual developers to large agencies, they examine how this conflict impacts the livelihoods of those deeply embedded in the WordPress ecosystem. Is this the kind of leadership WordPress needs going forward?…

1
Scorched Earth 15:00

10M ago15:00

15:00

Existential wasn't hyperbole. In this episode, Luke and Jonathan react to the breaking news of WordPress.org cutting off access to WP Engine servers, effectively crippling over a million websites. They unpack the potential motivations and ramifications of this unprecedented move by Matt Mullenweg.By Jonathan Wold & Luke Carbis

1
Existential Threat 15:00

10M ago15:00

15:00

Is WordPress facing an existential threat? In the premier of Season 7, Luke and Jonathan discuss Matt Mullenweg and WP Engine. They explore the implications of Matt’s recent actions, whether or not the benefit of the doubt applies, and the ramifications to the broader community.By Jonathan Wold & Luke Carbis

1
WordCamp Asia 2024 15:00

1+ y ago15:00

15:00

In this episode Jonathan and Luke reflect on their experience at WordCamp Asia, explore Luke's vision for the Plugin Review Team and how to improve developer relations in the WordPress community.By Jonathan Wold & Luke Carbis

1
The new role of themes 15:00

2y ago15:00

15:00

In this episode, Luke and Jonathan discuss the role of WordPress themes in 2023, how block themes and the Full Site Editor have changed the landscape and where the line between themes and plug-ins should be. They also reflect on their current projects.By Jonathan Wold & Luke Carbis

1
Repository Considerations 15:00

2y ago15:00

15:00

In this episode Luke and Jonathan talk about the ramifications of cloning the WordPress Plugin repository onto WordPress.com. How to do it in a way that keeps plugin developers onside, and as a bonus, Jonathan read the whole Terms of Service so you don't have to.By Jonathan Wold & Luke Carbis

1
Mullenmusk 15:00

2y ago15:00

15:00

In this episode Jonathan and Luke discuss the latest round of #WPDrama after WordPress.com cloned the WordPress.org plugin repository.By Jonathan Wold & Luke Carbis

1
Intrusive Ads 15:00

2y ago15:00

15:00

In this episode Luke and Jonathan disagree on who is to blame for intrusive ads inside of the WordPress admin Dashboard. They also cover some of the best practices and motivations of plugin developers, plus how to stop annoying the users.By Jonathan Wold & Luke Carbis

1
WordPress Security 15:00

2y ago15:00

15:00

In this episode Luke and Jonathan explore the complex world of WordPress plugin security and what really happens when a vulnerability is identified. The system could be better, but how do we fix it?By Jonathan Wold & Luke Carbis

1
Good Plugins 15:00

2y ago15:00

15:00

In this episode Joshua Wold fills in for Jonathan, discusses plugins, the value of good design in the onboarding process and what makes a strong product founder. Luke tries to bait him with comments about developer supremacy, but Joshua never took the bait.By Jonathan Wold & Luke Carbis

1
Best Events 15:00

2y ago15:00

15:00

In this episode Luke and Jonathan discuss their early WordCamp experiences and which is the best of the major WordCamps. They also discuss the latest news about the upcoming WordPress admin interface.By Jonathan Wold & Luke Carbis

1
Open Source Business 15:00

2y ago15:00

15:00

In this episode Luke and Jonathan share their vision for what open source business practices could look like. Jonathan even disagrees with Luke on wage transparency for no apparent reason.By Jonathan Wold & Luke Carbis

1
WordPress 6.3 15:00

2y ago15:00

15:00

Luke and Jonathan talk about the highlights of WordPress 6.3, the steady transformation from blogging platform to operating system and the need for a contributor focused event in similar fashion to Apple's WWDC.By Jonathan Wold & Luke Carbis

1
Welcome Back 15:00

2y ago15:00

15:00

Luke and Jonathan break into the new season talking about WordPress hosting, conflicts of interest, the importance of onboarding and the products that do it well (Luke also seems to have no idea what season we are recording).By Jonathan Wold & Luke Carbis

1
Finale 15:00

2y ago15:00

15:00

In the season final Luke and Jonathan discuss their future as professional e-sports athletes before returning to reality and talking about what happens when your product's functionality comes to the WordPress core. 8 down: while( have_posts() )By Jonathan Wold & Luke Carbis