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CloudFest USA Q&A With Jonathan Wold

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This week’s insider convo is with Jonathan Wold, cofounder of Guildenberg, a 3.5 year old company helping WordPress companies improve their offerings and improve the WordPress community. Beyond his time at Guildenberg, Jonathan has been in the WordPress space for 20 years and, according to his website he “still feels like a kid most days.” 

In our back-and-forth, you can hear from Jonathan on what he feels are the most pressing topics in the WordPress space, why he’s excited about CloudFest USA’s move to Miami and how the biography he’s currently reading makes him think about the future of technology!

Briefly introduce yourself to any of our readers who may not know you yet!

I’m a 20 year veteran of the WordPress ecosystem and still having fun with WordPress and on the Open Web. I started out as a developer, doing some of the earliest WordPress integrations with other systems, and grew from there into “enterprise WordPress,” working on big agency projects, where I focused for about half a decade. For the past 5+ years, I’ve been focused on the WordPress ecosystem as a whole. For anyone curious to learn more about me personally, I’ve just updated my homepage, which you can check out at jonathanwold.com.

You’ve worked in the industry for more than a decade, but 3.5 years ago you decided to cofound your own consultancy. What gap did you see in the industry that needed to be filled and how has your mission at Guildenberg changed over the last 3.5 years?

I love the WordPress ecosystem’s decentralized nature. It creates unlimited opportunities for hosting providers, product companies, and service providers to solve problems for customers and it’s a huge ecosystem. With all the benefits of being decentralized, though, there’s also tradeoffs. We started Guildenberg to focus on growing the WordPress ecosystem as a whole and mitigating those tradeoffs for the businesses in our space.

While our mission hasn’t changed, we’ve become a lot more hands-on in the past year, rolling up our sleeves and getting involved in implementation. A good example is the work that Tammie Lister, one of our co-founders, has been doing to put her knowledge contributing to WordPress Core to work to offer guidance and support to products that are building in the space and then actually helping them with implementation.

We released our mainstage agenda for CloudFest USA, but I want to know what topic or topics are front of mind for you in the second half of 2025?

The main topic that comes to mind for me at the moment is working past the hype of AI to solving real-world problems. I’m seeing more substance and promise, yet there’s still a lot of hype (and associated fear) around AI. I’m looking forward to seeing how that’s tackled at CloudFest USA.

You’ve attended CloudFest USA for a number of years, so you’re an expert. What are you most looking forward to about CloudFest USA 2025 and its new home in Miami?

I’m excited to see CloudFest grow! While the Austin venue had its charms, Miami is even more accessible for international audiences and you have space to accommodate a bigger crowd. I’m looking forward to seeing familiar faces and meeting new people.

If you could program your own fireside chat with one person currently working in the industry, who would it be and why?

I’d probably have a sit down with [CEO of CloudFest in Germany] Christian Jaeger to ask about his skincare routine and his secrets to staying young and stress free.

If Christian wasn’t available, I’d love to be surprised with someone I haven’t met yet who works in a product role at a hosting provider and see how they’re thinking about making WordPress a better experience for their customers.

If you could program your own fireside chat with any person, dead or alive, who isn’t currently in the industry, who would it be and why?

I’d love to sit down with Ron Chernow, one of my favorite authors, and get his perspective on the current state of technology and the web through the lens of the subjects he’s covered. His latest book covers the life of the American author Mark Twain. I’m halfway through it now and have found interesting parallels (and lessons to draw) for our industry.

P.S. From Christian

Ah, the skincare secrets are confidential—protected by GDPR and ancient Bavarian law. But I’ll happily share the secret to staying stress-free: host a tech event with 15,000 industry friends every year—it’s practically a wellness retreat!

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