[00:00:19] Nathan Wrigley: Welcome to the Jukebox Podcast from WP Tavern. My name is Nathan Wrigley.

Jukebox is a podcast which is dedicated to all things WordPress. The people, the events, the plugins, the blocks, the themes, and in this case WordPress sustainability, community engagement and release strategies.

If you'd like to subscribe to the podcast, you can do that by searching for WP Tavern in your podcast player of choice. Or by going to wptavern.com/feed/podcast, and you can copy that URL into most podcast players.

If you have a topic that you'd like us to feature on the podcast, I'm keen to hear from you and hopefully get you, or your idea, featured on the show. Head to wptavern.com/contact/jukebox, and use the form there.

So on the podcast today, we have Jonathan Desrosiers. Jonathan has been involved with WordPress for almost two decades, both as a user and a contributor. He's a principal software engineer at Bluehost, where his role sees him sponsored to work on WordPress through the Five for the Future program. Over the years, he's become a Core committer, and has spent many hours thinking about how to enhance the contributor experience, and make it easier for people to get involved in the project.

In this episode we discuss how WordPress releases might become more impactful by synchronizing them with flagship community events like WordCamps and State of the Word. A recent experiment of combining a major release with a live event spark some excitement, and Jonathan shares insights on the logistics behind such synchronized moments, the challenges posed by international holidays, and regional scheduling, and the broader vision for connecting releases with community gatherings.

We also get into the challenging landscape of the WordPress community, how it's recovering from the effects of COVID, the struggle to rebuild local Meetups, and efforts like mentorship and educational initiatives to bring in new contributors, particularly from younger generations.

Jonathan reflects on the importance of making release moments engaging and fun, akin to the anticipation of a new TV series or software launch, and the role of AI and open source in empowering a new wave of builders.

If you're interested in how release cycles, community events, and contributor onboarding are involved in WordPress, or what the future might hold for the platform and its community, this episode is for you.

If you're interested in finding out more, you can find all of the links in the show notes by heading to wptavern.com/podcast, where you'll find all the other episodes as well.

And so without further delay, I bring you Jonathan Desrosiers.

I am joined on the podcast by Jonathan Desrosiers. Hello.

[00:03:06] Jonathan Desrosiers: Hi, how are you?

[00:03:07] Nathan Wrigley: Yeah, good. Jonathan's joining me again. Most recently, I think we were at WordCamp somewhere. I can't exactly remember where, but I was chatting with him and Joe Dolson if memory serves. And a very different conversation to be had today because Jonathan has been mulling over how we can make releases impactful, and also how we can bind those to community events, particularly flagship WordPress events like WordCamps, things like that.

Before we begin that conversation, Jonathan, I wonder, it's a bit of a banal question, but people like to have the context of who you are. So would you mind just, very quick potted bio. Just tell us who you are and what you do in the WordPress space.

[00:03:44] Jonathan Desrosiers: Sure. So my name is Jonathan Desrosiers. I am a principal software engineer at Bluehost and I am sponsored there, the majority of my time is sponsored to contribute back to the WordPress project through the Five for the Future program. And so I've been there, probably since 2018, I think. And I've been a Core committer for almost eight years now.

I've been involved as an accredited contributor for 13 years now. And so I've been involved with WordPress for over a decade in many ways, contributing, but also as a user for almost, geez, almost two decades now I think. And so, I just had that realisation, it's been a really long time. It's been almost 20 years that I've been at least using WordPress in some way.

But week to week I do a lot of thinking about contributor experience, how we can automate things, or how we can make our processes more clear so that more people can participate. And just generally making sure that everybody has what they need to be successful. And whether that's mentorship, or they have blockers they need, certain people to come together and discuss, and get a consensus or understanding, you know, how the sausage is made in some way.

[00:04:56] Nathan Wrigley: I think it's fair to say that you are very much connected to the WordPress project. I think it's the fulcrum of your working life, and you are working at a very high level as well. So Core committer, things like that.

Now, in the recent past, it was probably, I want to say December in the year 2025, we had a kind of strange event happened. Not strange in the sense of weird, but strange in the sense of different, unusual. A release of WordPress came out and it coincided with an actual event. Now, in this case, it was State of the Word. So there was a bunch of people, and I believe they were gathered in New York. I could be wrong about that, but I think it was in.

[00:05:33] Jonathan Desrosiers: It was in San Francisco.

[00:05:35] Nathan Wrigley: San Francisco. Okay, there we go. Thank you for the correction. It was in San Francisco and the idea was that the release of WordPress would go out and it would be bound to this event. And there was this almost, how can we describe it? It was almost like television, basically. It was being filmed and streamed live all over the place. And there was this feeling of a big red button. There was a lot of people gathered around and they all sort of leaned in and pushed a big red button, and the release of WordPress came out.

Now, I don't know if the button actually did anything or if it was really sort of smoke and mirrors. I like the idea that the button actually did signal the release, but I don't know if that's the case. But the point was, there was a little bit of theater put into it. There was this idea that, okay, we've got this live event which lots of people will be watching. We've got a release which we need to do, which lots of people will be looking forward to. Why don't we sort of combine the two things?

And so it was a bit of PR really. And it also felt a bit like sort of marketing, and I'm going to use gimmick in the real sense of the word. So not like gimmick as in something pointless, but gimmick as in something different, unique. Something to draw your attention and grab you in. And I think the idea has been proposed that in the year 2026, the flagship events, the flagship WordCamps, so I'll list them in order in which they're happening.

So we've got WordCamp Asia, and then we've WordCamp Europe, and then we've got WordCamp US. The three releases of WordPress during 2026 will happen in tandem with those events. Now, why? Why would we want to do this?

[00:07:12] Jonathan Desrosiers: Yeah, so I don't think it was intentional, but the schedule just happened to coincide. You know, we were working on 6.9 and we realised, oh, the release date is the same as State of the Word. And so, I can't remember who originally had the idea, but it was mentioned that it would be really neat to just be able to publish it live at the event and celebrate that.

I guess the main reason behind it is just that, the more I'm involved in open source, the more I realise that the code and the license and all those things are important, but the most important thing underneath any open source project is the community that's involved with it. And what better way to celebrate our achievements and our accomplishments when we get together in different ways.

And so, typically that's in Slack or social media, right? We celebrate a release and we share the posts and say what we're excited about. But we also get together at different events and we do the same thing, right? We talk about what we're excited about, what we're working on, what's coming, or what we think should change in certain ways. Why not just do that at the same time and create even a more ultimate celebration, right? Another community moment where people have another opportunity to feel involved in something greater than them.

[00:08:25] Nathan Wrigley: Do you have any notion that this is going to be carried forward? I mean, I know that there was obviously a bit of serendipity in how it happened. The coincidence of timing and things like that. But do you have every confidence that this will happen, that Asia will get a release, Europe will get a release, and the US will get a release. In the year 2026, do you think that's going to actually occur?

[00:08:46] Jonathan Desrosiers: We will see. So as the proposed schedule is for this calendar year, right? There's three releases. Unfortunately, it's tough because the people planning WordCamps don't plan around our software's release cadence, right? They plan around budget, regional holidays, travel factors, weather, cost of venues and availability.

And so, you know, it's not reasonable for the Core team and the people working on releases to say you have to have an event in a certain month, right? And so this year, some people may not have noticed, but WordCamp Asia is in April this year, which it's been in February so far in the previous editions. And WordCamp Europe is in June, which it's traditionally usually in.

And so that's not a big enough gap to have another major release. And so the proposed schedule is saying, let's release during WordCamp Asia, let's release during WordCamp US, and then we'll release again at the end of the year around State of the Word. We don't have a date for State of the Word yet, but it's around where we think it might be.

And likewise, creating a schedule for releases is incredibly hard because if we don't release in the first week of April, for example, then I believe the whole month of April has major religious holidays scattered throughout it in different areas of the world. And if we released in March, that was way too soon because we started the alpha phase of 7.0, that starts when the previous release is branched, like it's separated from the primary branch in the code base, and that happened in like November.

But there's US Thanksgiving, there's Hanukkah, there's Christmas, there's New Year's, right? A lot of people in the community take the majority of December off, and so that's like a washed month, right? And so we would've had essentially four weeks until the feature complete point of the release. So that was too soon. And so it's just as hard to plan the release schedule in a way that doesn't negatively impact everybody as best as possible as it is to plan these major events.

And so I can't say that it will be a guarantee going forward. We're trying it out this year to see how it goes and what we can learn from it. We felt that the State of the Word was successful and it was exciting. It was unique in its own ways. And so we want to try, continue trying this this year and see how it goes.

[00:11:06] Nathan Wrigley: Gosh, the piece that you just said there about the religious holidays and what have you, that really opens up a really interesting discussion. Because it is quite likely, I imagine, that the listenership to this podcast probably never gave that any thought, that this kind of international calendar, be it a religious calendar or maybe just a vacation calendar in certain parts of the globe would really impact when the release can happen.

Because there are people who are committing to the project, and they tend to be in certain jurisdictions. And so if there are people who are on, I don't know, a week long holiday, nationally, in a specific jurisdiction, and they typically are a large part of the team that are committing in various different respects, that's important, but probably something that many people would not have thought about.

Now, in terms of these releases then, is the idea, well, I'll backpedal a little bit. It occurred to me that quite a lot of the people who may be involved in releases are the very kind of people who would find themselves also at some of these flagship events. Now, obviously it's not going to be 100%, maybe it's 25% of the people who are release leads and part of the teams that are committing here, there, and everywhere.

I was worried that there'd be people on airplanes, people trying to land and orientate themselves in the country that they've landed in in the same period of time when they would've been heads down, in their office, in their study, figuring out the bits that might be broken with the upcoming release. Is that a thing? Is that part of the jigsaw puzzle of this?

[00:12:32] Jonathan Desrosiers: It definitely is, yeah. With any release, there's no time of the day where everyone on the planet is available to work on something, right? And so another part of this is that, in a way it forces us to have a major release in different geographic areas so that everywhere on the globe there's a WordPress release that they may be able to participate in, right?

And so, likewise with travel, right? So when we assemble a release squad, we have to think, okay, it's based in, for example, this one was planned to be released at WordCamp Asia in India. So we want to make sure we have a mix of people that are in different areas of the world. And not just so that there's always people around to respond to things throughout the entire cycle, but we also want to have people that are present and not present at the event that are participating. And maybe the wifi is completely unusable or maybe something happens, right? So it's good to have people that are there and not.

And that was part of the announcement too, is that we tried to underscore the point that it would be great if everybody could go to WordCamp Asia, but traveling is not a requirement to participate in the release at all. And that's a good thing, because it's good to have people in multiple areas, multiple time zones.

With WordCamp Asia, once contributor day ends, it's the beginning of the US daytime, right? And so those contributors can sign off and there's people around to help carry that torch and continue on if there's any follow-up issues or anything that needs to be investigated.

And so, yeah, that's also a consideration is how, I guess we can call it global coverage, right? Like, how can we ensure we have global coverage so that there are people with the right skill sets, and right availability, and right knowledge, to be able to take on certain tasks or responsibilities or perform investigations, whatever may need to be done as part of that release process.

[00:14:26] Nathan Wrigley: I, like you, am really in the weeds of the WordPress project. I obsess about it in a way that's probably not all that healthy. I'm very well aware of when the next release is coming up. I'm usually fairly aware of what is going to be in that release. But I imagine most people using WordPress, it's probably a bit of a surprise. You know, they open up WordPress one day and either it has updated. If it's a point release, probably it's a more manual thing, if it's a major release, I should say, but if it's a more minor release, maybe things have updated in the background during the course of the night and what have you.

But I'm thinking of TV series now. So when a successful TV series has a new season, there's all this fanfare and buildup and you know it's coming. You see the commercials, you see the adverts. And the moment that TV series comes around, you are excited, you're ready to go. And I remember back in the day, this is going back a long time, when Firefox would make a release, they sort of did this thing like, I don't know, every 18 months or something like that. Not like now where it's every couple of hours it seems, that browsers update themselves.

But when it went to, I don't know, 3.6 or something like that, there was this big fanfare, this big moment. Everybody took stock and what have you. And are you trying to encourage a bit of that? Are you trying to create a bit of razzmatazz and drama and intrigue and awareness and all of that around the release, and make it feel like an important thing, which with the best will in the world, it kind of has not been more recently? Most people, it just updates. There's no fanfare whatsoever. But we can leverage it to make it important, significant, fun, interesting.

[00:16:04] Jonathan Desrosiers: Yes and no, right? Like, we want to celebrate the community and the work we're doing now. I actually would love it if we could get to a point where we're releasing every, I don't know, every week or every month even, right? Not have to wait every three or four months. There's some value in having that penultimate moment, right? Of, we've worked for three months on this. But there's also aspects of the world where we expect things faster and more instant and waiting for the patch that you submit in January to be released in April is not really, like maybe you lose interest in contributing in that time, right? So there's many different things like that.

Some things that you mentioned really resonated with me as far as awareness of what's coming or like what's been done. In a way, the fact that users are not so aware of what's being added or what their site has updated to, it's a sign of the success of auto updates and how seamless those are.

Because for a little while I've been considering, when you update WordPress manually, you're redirected into the about page in the dashboard, right? And every release, there's a new about page that's designed, it works hand in hand with, we call them the micro sites, which is like a wordpress.org's landing page that showcases the release. And it just explains all the features that have been added.

But you only see that if you either go to the about page manually or you manually click update when you're in the dashboard. And a site might have many administrators that only the person that actually updates will see it. And so I've been thinking about ways that we can make users more aware that their site is updated. Or maybe that's not the important part, but maybe it's just the important part to make them aware of the new features that are available to them, right?

Maybe we put some type of a widget on the dashboard where we link off to a Learn WordPress page that teaches you about how to use the Notes feature that got added. The other thing too is you mentioned about the TV shows advertise when they're coming up, right? Maybe we need to do a better job of advertising what's coming up and encouraging people to opt in early and test.

And in a way a more rapid release cycle leads to that because many of the browsers have different feature flags and they build features out in different branches, and you can actually opt into testing a specific feature and that would get turned on, but maybe not all the other things that they're working on until it's ready.

And so maybe we need different ways for people to get involved testing, or trying things out earlier to understand what's coming, but also to give us valuable feedback, how it works on their site, what breaks, what it doesn't interact with. All of that is very valuable feedback, and we should always be striving to get more testers and more awareness around what's coming because it creates new feedback loops that are valuable for different reasons.

[00:18:58] Nathan Wrigley: Yeah, it's kind of interesting, and what I'm about to say, I am sure that a significant proportion of the listeners to this podcast will say, no, Nathan, we don't want this. But here's a proposal then. Here's an idea. And again, I'm going to hark back to the TV series.

The TV series, typically when they've started advertising between other television programs, that TV series has been made, the footage has been shot, the graphics have been done. It's basically ready to roll. And then they parcel all that up and then they release little snippets of what's coming so that you can prepare yourself and get excited.

I kind of wondered if something like that in the dashboard, akin to the about us page, but in the run up to the release. So all the graphics have been made. We know basically what's going to drop in this release. Now it may get tweaked here and there at the edges, but we know what's coming. I've always thought that would be a really nice idea.

I would love to see that. And I realise a proportion of people would think, no, we really don't want that. But I think that's a perfect opportunity to get people drawn into, oh, this is coming. Collaborative editing, that's about to happen is it? Gosh, that's really interesting.

And then this call to action could be dropped in, but we need some testing around the edges of it. We've got the bare bones of it, but we need some more eyeballs on it and what have you. So that proactive demonstration of what's going to happen rather than the reactive, your site has been updated, here's what there is, which is already there. This is more of a here's what's coming, get excited, get involved, yada yada.

[00:20:29] Jonathan Desrosiers: In some ways the feature branch model that I described lends to that, right? Because then it's not, here comes this feature and then, oh, actually we left it out of this release, right? It's its own thing that's being worked on. And then when it's released, it's released, and it's here. But it doesn't make it any less, any worse off than other things that are shipping in the release, right? Because it's its own thing, and it's its own, it has its own criteria to be ready, in a state that we're comfortable with shipping it and supporting it forever because of backwards compatibility.

And so yeah, I think that what you're describing is essentially what I was describing, a little bit more detail. And there's of course a lot of nuance there around how often do we do that? We have a lot of parts of the release process that need to be automated before we can even consider that. The different parts of the block editor are, many of it is managed as packages, NPM packages. And so a lot of those are so interconnected, it's a little difficult to release just one feature because they're all being updated at the same time.

And so like there's some architectural things to think about around that. Like, how do we compartmentalize things better to be able to do that? Make sure we don't accidentally include something that's not ready but when we intended to include a certain feature. There's a lot to unpack there and I don't know that we'll ever get there just because of the sheer size of the project and how, backwards compatibility, how long we've been around.

But I think that training users that auto updates are important to have enabled that are quality, you know, not shipping things that break people's sites as much as possible, even though it's unavoidable because of how flexible WordPress is.

After 6.9 came out, I was looking into some of the data because I had this gut feeling that 6.9 was being updated to, slower than other releases. And so for a little while I was looking at that. And after about a month, I was like, okay, this is just a hunch. Let me go and actually look at the data around this.

And so what I noticed was actually the opposite. When I looked at, I created 5% thresholds for the percentage of total WordPress sites. And when I looked at the data, I realised that for the last 10 releases, let's see here. So every major version of the last six to eight releases has passed 35% of all WordPress sites in two days or less. And also every one of these columns as far as percentages is increasing.

And so WordPress 6.9 reached the 50% threshold of all WordPress sites in 10 days, and that's four days faster than 6.8, which was the next fastest. And currently we're approaching 65% threshold of all WordPress sites. And only six other releases have done that so far. All of them are the most recent ones, except for 4.9, which we all know had a waiting period for Gutenberg. And the only release the past 70% was 6.8.

And so I'm interested to see how this trend continues because it's showing an acceleration of adoption for each new major version of WordPress. They're getting installed faster, by more people. It's a sign that we're shipping stable software. People are more confident. People are opting into auto updates for major versions. And in general, it's just a quality sign that we're doing something right here. And so how can we lean into that more?

[00:23:52] Nathan Wrigley: Okay, let's pivot a little bit. Let's sort of bind community, we did touch on this a minute ago, but let's spend a little bit of time binding the community to these kind of things because right at the start you mentioned that really the community is the underpinnings of your interest in the WordPress space. The code is obviously tremendously important, but without the community there is no code basically.

And so we've got these events. We're trying to create interest around the WordCamps and the releases at the same time. But just looking back over the last period of time, let's go for year, two years, something like that. I don't know what your spidey sense is telling you, but my spidey sense is telling me that that community portion, it's sort of slowly but surely, it feels like it's withering away slightly.

I'm not really picking up on like this angry mob of people who are stamping their feet and shouting, I don't want anything to do with the WordPress community and then disappearing. I mean maybe there's a few of those, probably, somewhere. But I don't get a sense of that. I just get this sense of sort of, somebody's pulled the plug out of a bathtub and it's slowly sort of draining away.

Attendance down at WordCamps. Meetups struggling to sort of get the numbers that they had several years ago. And so it would feel like at the moment, you would have to be watching the news fairly closely, especially right now. So at the beginning of February, 2026 is when we're recording this. There does seem to be a push from the senior leadership to make WordPress Meetups and things like that, a much more central part.

And then there's this whole broad spectrum of educational initiatives as well going on. So we've got WP Campus Connect, we've got the Credits Program and a whole smorgasbord of other things which is happening.

So there's no question there, really, what I'm just trying to do is give you the opportunity to bind the two things, the WordPress community and the software, and really just talk about whether you've noticed the same thing as me, where there's this slow, withering of the community. And maybe this is a part of just sort of getting it all back together, making events like this a bit more fun and interesting.

[00:26:02] Jonathan Desrosiers: Yeah. I think there's a few things there to call out. The first observation I've had over the last year is there's a palpable excitement to build with WordPress again. I'm noticing there's a renewed enthusiasm. People, they want to move on from certain things, and they want to get back to building experiences and tools and things on the WordPress platform.

But there's also, I think we're dealing with some, in some ways, a long tail COVID effect, right? There was obviously, you know, a lack of in-person events for a while, and during that time a lot of the people who were keeping Meetups alive and WordCamps alive, they moved on, or burnt out, and chose not to return after. And so there was a break in that pipeline of, usually there's a lead doing that and there's other people learning under them, and then they move up and take over. And that was totally disrupted and I think that we're still trying to rebuild that.

I think that it manifests differently in different areas too. So for example, the APAC WordCamp community is very strong and they have lots of WordCamps. But in the United States, there was one WordCamp that wasn't WordCamp US last year, I think, Montclair. And I lead the Boston WordPress Meetup and so finding speakers is difficult. Getting people to come out is difficult as well. And I think those are partially just larger societal shifts where it's harder to get people to come out to certain things. And we just have different preferences as far as how we consume information or learn.

But I'm still not sure why the difference in the geographical areas, and I think it may have to do more with, APAC is a more emerging market when it comes to WordPress, right? Like their community, especially in certain areas has been growing and is much newer than it is in the US. And so I think that they're growing their communities for the first time in many ways, right? But in the US it's the second or third or fourth time that we're growing those communities or revitalising those communities. And the form that that needs to take, I think is a little different. And I'm not clear on what the holdup is there.

But I do know that a big factor of that is to get new people involved with WordPress and interested in WordPress, and that's why some of the priorities that Mary Hubbard published, and one of them in particular is education and awareness and all of those different things that work together in the form of the WP Credits program, mentorship programs. There's been the contributor mentorship programs that happen every few quarters in WordPress over the last few years.

And we've seen some really great contributors who were mentored in that program, and then the next time the program happened, they mentored, and then they became a team lead, and then they served on release squads. And so we've seen some really great contributed journeys through those paths.

[00:28:53] Nathan Wrigley: I'll just sort of run through with you the kind of things that I've noticed in my part of the world. So I think COVID is an enormous part of it. It upended so many ordinary things in life. So, as an example, you know, people obviously, they ceased going out, and then that pattern of not going out became habituated. People didn't go out because that's not what you do.

And in the UK we have this institution called the pub, which I'm sure you've heard of. And it used to be that prior to COVID, the pub was the real centerpiece of many communities. You know, towns, suburbs, what have you. Everybody would coalesce around the pub and that was very important. Since the pandemic, a lot of those institutions, they don't really function in that way anymore. You know, there isn't the throughput, there isn't the footfall and so they go out of business.

And the same, I presume is true in the WordPress space. You know, we're trying to encourage people to get up, leave their home, spend money on transportation. Obviously there's the time cost, the sunk cost of time and what have you as well. It's difficult, but it makes me more sanguine that it's not just like, it's not just a WordPress thing, you know, it's the whole of society.

But like you said, I get the feeling that the WordPress community has begun to address it. And the way it's being addressed is through these educational initiatives. Trying to get a throughput of younger talent. So get them at the school age, get them at the university age, and then hopefully they will have an interest. They'll get a flavor of what it means to be involved in these Meetups and things like that and hopefully take those on.

It's a laudable goal. I hope that it has the capacity to transfer. You know, so in a decade's time we can look back and say, look what happened. This young blood emerged. I think it's yet to be seen. I think certainly in the area, the locale where I am, the United Kingdom, we don't see evidence of that yet. Maybe in the US that would also mirror.

But from everything that I've learned and the people that I've talked to for this podcast and events in Asia and places like that, that seems to be a really different picture. There seems to be a real thirst for solutions like WordPress. Because there's a direct kind of career path there. You know, you can pick up a free piece of open source software, crack open a laptop and get going and start to sell your services far and wide. And so again, there's no question there, just observations that I hope these initiatives bear fruit. But it'll be interesting to see. Only time will tell.

[00:31:16] Jonathan Desrosiers: I think at the root of what we're dealing with is that people are motivated by what they see as valuable, right? If they're not going out to events, so they're not engaging with the community, they don't recognise or feel that it's valuable to them in some way. And so we're having to reprove why communities are valuable, why open source is valuable, why you should care.

And then the other aspect of it is, you know, overall project sustainability. We can't just keep getting older. We need to have a balance of new, younger people that get involved as well.

And so one way to lean into getting younger is obviously, like you said, to approach people at schooling age, right? Or university, and teach them about open source. Show them how to contribute, how to be a part of a community, and why it's valuable. But we have to be really careful because we need to be prepared to, I've written in the past that we need to be prepared to activate these contributors, right?

So it's one thing to make them aware of this, but it's another thing to make sure they're properly supported and we give them pathways to grow. We give them clear criteria to be successful, clear projects to work on, so they understand what they're doing and what they're trying to accomplish.

And I think that this is one thing that is also a benefit of having the releases coincide with these major events because new people are getting together already, so why not use that opportunity?

One of the goals that every table lead and every organiser of a Contributor Day has is to ensure as many contributors see, realise their work over the finish line. And so on the Core team that's a patch that someone tests gets committed, or a patch someone writes gets committed to WordPress, right? How can we make that more valuable, where it's not just ending when they leave Contributor Day?

And so I've been thinking about all the different logistics and helping to coordinate with the WordCamp Asia team and the 7.0 release team to make sure we're prepared for that final day. And one of the things I've been thinking about is the release process itself. One of the best, lowest friction ways to get involved with WordPress in the actual release process. And you don't need any experience contributing to really take part in it. And that's when we get to a point where we say, okay, here's the zip file of what we think we're going to ship, go test it.

And so people will take it, and they install it on their server and they say which version of PHP they're using, and how they installed it and what they did and, you know, it worked. And the majority of that though is just looking for problems. And when problems don't come up, we just don't do anything with all the information that people are dropping, right? And there might be 50 people at a major release. We call them parties, but at the release parties that are dropping information. And again, if there's no red flags, that information just largely goes away.

But, how can we rethink that and make that effort more meaningful, and also create a pathway for them to continue contributing in some way past that moment? And having everybody in person is a great way to have pilot programs for different approaches, because there can be someone that briefs a set of contributors on what we're going to try this time, here's what we want to do, give us feedback on how you felt it went. Everybody that's involved in the squad and doing the release can say, oh yeah, that actually was really helpful and better than what we do before.

And these newer individuals that are learning also have fresh perspective. And so having them participate in these, I guess I'll call them experiments of such, but just these processes and things that we are considering, it helps get that fresh opinion and perspective on why things are working and why things aren't and helps us just improve.

[00:35:04] Nathan Wrigley: I've got three children and they're all of a certain age now, they're certainly no longer small. You know, they're basically adults. And it's really fascinating looking at the kind of things that engage them. I think they've just grown up in a different era. The diet of the kind of things that excite them is very different to the kind of things that excited somebody of my generation, just because, you know, they've had the whole world in their pocket ever since they were born.

And having that dialogue with the next generation, and trying to figure out what it is that they want and that they desire. And even things like open source. So when, I was already an adult before the internet began to be put into everybody's homes, and people started to own personal computers and things like that. And so I was ready to receive that message of open source right at the start. And it became really obvious to me, oh, that's a really clever way of making software.

But now of course we've got this landscape of closed platforms. Everything's free at the point of use, but everything's not free in any way, shape, or form. You can think of the siloed platforms that I'm talking about. My children have been raised with those and so just even making the argument about open source is hard enough.

So I think what I'm really advocating for is, obviously we've got to shepherd these people in, but at the same time, I think we have to be willing to let go of a lot of the things that we think the project is. We think the Meetup should contain. We think the WordCamp should maintain. Because at the end of the day, we're competing for eyeballs and if we don't make it, I'm going to use the word exciting, if we don't make it exciting, they're just not going to show up.

And I feel that's a piece of the next five, six years, trying to figure out what excites these people. Because unless we do excite them, I fear the Meetups are going to be empty and there'll be a certain throughput from the WordPress initiatives, Campus Connect and what have you. But we need to make these things exciting, interesting, innovative, fun. But I don't have an answer to that.

[00:36:59] Jonathan Desrosiers: Yeah, you touched on something interesting that I've been thinking about quite a bit. I gave a talk last year about how to implement AI into open source communities while maintaining what makes them great in the first place, which is the human element, right? The community aspects of it.

And so I've been thinking a lot about just AI and how it's affecting us. And there's a few things that I'm really excited about with AI and those are empowerment and learning. And so you can have an AI model that digests massive amounts of information and summarises it in the specific way that you learn best, right?

And likewise, I'm noticing that people feel more empowered to try things themselves because they have more of an ability to distill a lot of information down into something that's digestible, right?

And so I feel that the tension between those two areas of closed and open is growing. Because when I was growing up, computers were just starting to be less than the size of a car, right? People were starting to have them in their house. But they were still at a point where, the computer went bad, you took it apart and fixed it. You didn't trade it in for a new one, right?

And so I feel like my generation, there was a level of, we had the tools, but we had to go out and build the things we needed ourselves in some ways, and experiment. And then there's been the generations between that and now where they pretty much had everything that they needed.

But AI is changing what we need, or what we want, and what ways we want it. And so now there's a new found need to build again in some ways. And in some ways it's kind of a circle, right? Because it's, the AI is making it easier to build, but it's also making you more aware you have to build. It's kind of like building against itself in certain ways.

But I'm finding that there's more of a willingness to do things on your own, try to tackle something you would typically need to hire a professional to do in the past. You know in many ways we need to lean into that because then that gets people excited. Oh, WordPress, I could use WordPress to build this, or I could use just the WordPress for just the database part of it and the REST API and have some type of application on it because it scales well and it caches or whatever it may be.

But I feel like people are starting to scoff at the walled gardens a little bit more, and I'm seeing that there's a resurgence in things like RSS. I'm seeing new RSS readers are popping up. People are leaning towards the Fediverse. People are blogging more, having their own website instead of just their business on Facebook, right? Because that can get taken away.

We saw with Twitter how they just chose to close their platform. And embeds no longer work in WordPress because they shut down oEmbeds. And I feel like it changes every month, but there's times where you have to log in to see a post, or you can't see a post, or you can see one post and then you can't see any more that's shared externally. Yeah, so it gives you more control.

[00:40:02] Nathan Wrigley: Yeah, I think that's really interesting. And I also noticed that swing. Obviously, I don't have any broader data. I can only point to the things in my life, the little intuitions that I'm gaining. But I see the same thing. I see an interest in AI, so we'll just put that to one side for a moment. But in terms of the closed platforms, I do see that the people that I know who are significantly younger than me, they have intuitions around that, and they've kind of figured out for themselves that this is not great. It seems to be a vehicle to serve me ads, and I wonder what the incentive is for the stuff that I'm seeing, and maybe it's kind of pushing me off in one direction politically and all of that.

And yeah, this resurgence of RSS, of the blog. I know it's hard to talk about, but it's almost like we're doing some sort of archaeology in the internet space. We've gone back to something older. We kind of dug up the relics from the past and we found that they're still usable. They're still there.

It'll be so interesting. But I think if it was just the RSS and it was just the open nature of things, I think that's going to be a hard sell. But throw AI into the mix, this capacity for somebody with very little relationship with writing code who can get something credible out. Now, it may not be robust, it may have security problems here and there. The accessibility may be something that needs to be addressed and what have you. But who can argue with the excitement of it.

You know, you tell a computer to make a colourful website that's got rainbows and pictures of cats, and sure enough, two minutes later you have a website with rainbows and pictures of cats. And that wasn't possible until just a couple of years ago. And so I think we've got the tools. I think there's things that we can deploy. AI seems to be the primary one at the moment. Let's hope that that continues to be sustainable.

But that's interesting. That gives me some hope. And the way that you've encapsulated it, open source combined with things like AI. Trying to get Meetups back. Trying to combine it with educational initiatives. Trying to combine it with WordCamps and releases.

[00:41:52] Jonathan Desrosiers: You mentioned something that's important there in that it's very easy for someone to get something built that they need specifically, right? And I think that's where we're at right now where AI is, like I said, is empowering, but more on a personal level. Once you need to scale those things, that's when it gets difficult.

And it's a rollercoaster of, oh my God, there's going to be no software. And then, oh, look at all this crappy software that AI built. We are always going to have a job. And then it's like up and down all throughout time as new tools get released. And it definitely matches what I'm seeing is like the personal empowerment level, they could take that and run with it and build this really massive thing, or they could just build something that they just want, that does specifically what they want, that they haven't found out there that it accomplishes.

And I think that another aspect of that is I'm noticing that a lot of people that you may not have thought would try things in the physical world on their own are more likely to do so as well. So maybe changing their faucet, or doing a landscaping project or something. I feel like we've had YouTube tutorials, right, has been a big thing for maybe a decade, right? But I feel like AI has unlocked a new level of empowerment where people feel more confident to try things because of the knowledge that's available to them in different ways.

[00:43:09] Nathan Wrigley: The year 2026 is going to be punctuated by WordCamps. It's going to be punctuated by WordPress releases. Hopefully we will start to see the needle move on educational initiatives, and maybe some younger people joining in with the community.

That has been a fascinating chat, Jonathan. I really appreciate that, getting your insight into what I think we both hope is going to happen in the WordPress project. That it will still be relevant in 10 years time, and that there'll be children who are now, not old enough to be using computers, in a decade, they'll be coming on podcasts like this, and hosting podcasts like this, and being involved in the community that we love so very much.

Where can we find you, Jonathan? If people want to talk to you and have a bit of a natter, where's the best place to locate you?

[00:43:48] Jonathan Desrosiers: My website is just jonathandesrosiers.com. I'm desrosej pretty much everywhere on the internet. I try to keep it consistent and easy. And you can also, of course, find me in the wordpress.org Slack.

[00:44:01] Nathan Wrigley: I will link to all of those in the show notes. So if you go to the wptavern.com website, search for the episode with Jonathan Desrosiers, you'll be able to find all of the links probably at the bottom underneath the transcript and the preamble. Go and have a look down there and hopefully we'll be speaking soon. I'll probably see you in Mumbai in a few weeks time. Take care, Jonathan.

[00:44:21] Jonathan Desrosiers: Thank you. Look forward to it, and hopefully I see your listeners there as well.

[00:00:19] Nathan Wrigley: Welcome to the Jukebox podcast from WP Tavern. My name is Nathan Wrigley.

Jukebox is a podcast which is dedicated to all things WordPress. The people, the events, the plugins, the blocks, the themes, and in this case, redefining WordPress product growth in a crowded ecosystem.

If you'd like to subscribe to the podcast, you can do that by searching for WP Tavern in your podcast player of choice, or by going to wptavern.com/feed/podcast, and you can copy that URL into most podcast players.

If you have a topic that you'd like us to feature on the podcast, I'm keen to hear from you and hopefully get you, or your idea, featured on the show. Head to wptavern.com/contact/jukebox, and use the form there.

So on the podcast today we have Matt Cromwell. Matt has been an influential figure in the WordPress ecosystem for many years. He co-founded GiveWP, led its growth, and continued his journey as part of the StellarWP leadership after it was acquired.

Recently, Matt has shifted gears, launching something new. It's called Roots and Fruit, and is an agency dedicated to helping WordPress product businesses thrive. In recent years, WordPress has gone through a period of flux. There's been shifting stats about WordPress's market share, tightening budgets, and increasing competition from both within and outside the.org plugin repo. Despite these changes, Matt remains optimistic about the opportunities for product makers, especially as WordPress evolves alongside emerging technologies like AI.

Matt starts off by sharing his background, his experience with GiveWP, and the unique perspective he gained navigating growth, crisis, and the challenges facing plugin developers. We then talk about how the WordPress product space has matured. Why building a plugin, or theme, and hoping users will simply discover it is no longer enough, and how focusing on the customer journey, branding, and marketing is more crucial than ever.

Matt is now positioning himself as a mentor and guide for solo founders and product teams, helping them prioritize growth efforts, refine their product experience, and avoid the scattered approach that many developers fall into. He brings practical insights from years of hand-on experience, and explains why a successful WordPress product business relies on process, diligence, and wise prioritization, not just code and hope.

If you are building digital products in WordPress, and want to learn how to make them stand out in a crowded, competitive ecosystem, this episode is for you.

If you're interested in finding out more, you can find all of the links in the show notes by heading to wptavern.com/podcast, where you'll find all the other episodes as well.

And so without further delay, I bring you Matt Cromwell.

I am joined on the podcast by Matt Cromwell. Hello, Matt.

[00:03:22] Matt Cromwell: Hi. Happy to be here.

[00:03:24] Nathan Wrigley: Matt and I have chatted many times. In fact, we were having a nice chat just before we realised that the time was going to get away from us. So we've diverted and pressed record. We were getting into AI, but we're going to park that because that's a whole different episode. Well, maybe not. Maybe there'll be bits of that leaking into this episode.

[00:03:39] Matt Cromwell: It'll come up.

[00:03:39] Nathan Wrigley: I'm sure it will. But as I say, Matt's been on the podcast before. He has had a significant sort of reshaping of his career in the recent past. And so we're going to talk a little bit about what the new direction is, and where he's going to be focusing his efforts in the near to long term.

But Matt, just before we begin, do you want to tell us a little bit about you and what you've been doing in the WordPress space these many years?

[00:04:01] Matt Cromwell: Absolutely. Thanks so much. I'm Matt Cromwell. I am was, it's hard to figure out how to introduce myself anymore. I was co-founder of GiveWP and sold that product in 2021 to Liquid Web and stayed on and came on the leadership team of what became StellarWP, and took all the things I learned from Give and got to apply them across lots of products, in an excellent learning journey.

Recently exited back this last fall, 2025, and went on a journey of discovering in what I want to do, and found that I could not prime myself away from the keyboard enough and decided that now's the time I get to invest my time and efforts and energy in the WordPress product ecosystem like I always have. So I built a new agency called Roots & Fruit, which I have basically said is your fractional chief growth officer agency. I just launched a couple weeks ago and it's going well. So that's what I'm doing. That's how I say it.

[00:05:02] Nathan Wrigley: Yeah, I love the domain, by the way. The minute I saw that, I think I got where you were going without even having read a word. Roots & Fruit sort of says it all, doesn't it? It's the growth to the actual harvesting at the end. And so we will get into that.

Can I just ask you though, we'll begin this way because we've had several years now of flux in the WordPress ecosystem. You have charted the growth of many products in the WordPress space. You've been involved in them personally, and you've seen the journeys of other founders and what have you.

Do you have the same level of optimism that the Matt Cromwell, let's say from the year 2020, when everything was going gangbusters, that 35% went to 38%, went to 40%, and on it went. Do you have the same level of optimism? Do you think there still is fruit to be harvested in the WordPress space in 2026?

[00:05:59] Matt Cromwell: Absolutely I do. There's a lot of caveats in there, I have to say. Being at GiveWP, we had a unique perspective when it came to things like a pandemic. It was like an internal thing where we were afraid of becoming ambulance chasers, okay? Because, especially in the US, when a crisis would come, suddenly our sales would go through the roof. And it's because when bad things happen, people need to do fundraising. And the worst thing we wanted to do was start capitalising on trauma or things like that.

And so when COVID came along, we were like, woah, this is going to be significant. And it was. It was a very significant thing. But we had been through the motions, so we knew that it was going to have a downside on the tail end of it, sales-wise. And I think a lot of folks understood that conceptually as well. But we had experienced it a lot.

But what a lot of folks found out on the tail side of COVID was that the downside was worse than it was pre COVID. A lot of folks felt that, even GiveWP to some extent and several of the Stellar products were like, oh, we've leveled out, we've come down off of the COVID high, and actually it feels a little bit worse than it was before. Budgets got tight in terms of businesses and agencies, nonprofits, things like that. There's lots of circumstances to those things. But over the last year or so, a lot of product companies have started to see things start to slowly climb again.

But in the WordPress space, I think it's important that everybody also look at our ecosystem in the bigger ecosystem of just the web. On the web there are small to medium to large companies launching all the time with huge amounts of success. Just a couple years ago, nobody knew what Lovable was. Now it's a billion dollar company. Things like that do happen and they happen regularly. That to me means there is still lots of appetite for the kinds of solutions that we are trying to bring to the world through the web. And we can be part of that solution.

Now, the conversation you and I had a little bit before was more about like, what about WordPress and the threat or the opportunity of AI? I do think the way in which WordPress Core has been tackling AI and trying to bring tooling into WordPress Core is making sure that WordPress itself as a platform has not only a future, but it has a lucrative future. I think the way that they're going about it is really smart and really intelligent, and it is going to actually build the platform in a way that makes AI understand how to build with WordPress better than anything else out there.

WordPress is the most, one of the most documented, open source projects in the world, and it's been open source this whole time, and AI loves that kind of stuff. So it just has been able to scrape the WordPress database, the WordPress code, all the WordPress documentation over years and years and years. AI now knows WordPress really, really, really well. So I think there's lots of opportunity.

[00:09:07] Nathan Wrigley: Yeah, no, it's really great because you covered a lot of ground there. I should say, dear listener, at this point, maybe go and have a look at Matt's domain. I mentioned it, but I'll just read it into the record. So it's Roots with an S. Roots and fruit singular, .com, rootsandfruit.com. So go and check that out. Maybe pause the podcast if you're at a screen and.

[00:09:28] Matt Cromwell: Singular and plural.

[00:09:29] Nathan Wrigley: Both. Yeah, you've managed to get all the goodness in there. Go and pause the podcast and have a little poke around and you'll get some intuition as to what Matt is doing over there.

I'm going to sort of sidestep a little bit though, because I want to frame this question slightly differently, and that is to, I'll frame it like this. I, as a consumer of WordPress things, I've spent the last 15 or so years pottering around, having a problem, then going to Google and discovering that there's typically a WordPress plugin or theme or what have you, for that. And then I go to their website and perhaps there's two or three websites that I might be juggling and thinking which one is superior for the needs that I have. And then I purchase something, you know, I go and I buy a premium version of something or maybe download the free version to give it a test.

But the point is, I have this really abstracted concept of what it is. I'm buying a commodity. So I buy the finished thing and it comes as a zip file, and I typically don't interact with a human being. And that's the interesting bit that I want to get into to begin with, is the human behind all of this, which was you for many years.

And so can we just explore that a little bit? What is the stuff that somebody like you, when you were with GiveWP, but maybe now the clients that you are going to be servicing, what is their day involved with? What do these people do? What are the anxieties they have? What is the stuff that makes up a plugin or theme developer's life and business?

[00:10:55] Matt Cromwell: Generally speaking, product folks are nerds, love to be behind the screen. And they like this kind of industry, specifically because they don't have to be the person dealing with the customer as much. That distance that goes between the screen basically, is something that gives them a sense of safety, where they get to focus on the work that they love and they enjoy, without having to deal with the noise of the people.

The exception to that are all the folks that are highly motivated to help with technical support. And I love those people. Those are my people. My focus as a founder was more on the customer support and marketing side of things, so I enjoyed being more of the face of things for our brands over the years.

But the allure there is both being able to have that separation from the noise of the public, but also having a little bit of the security of what might be called mildly passive income. And that's the big difference between folks who are running an agency and folks who love to run product. Agencies are service oriented folks. They have to be with the customer and the client all the time. You are paying for hours. You're being paid for the time that you put in, in many ways. With agency service work, there's ways to get away from just purely time-based charging, but by and large.

In the product space, you're not being paid for the time you put in. You're being paid for the product, and for the outcomes that the customer experiences. And that's what you bought Nathan, when you went and bought a utility or a tool or whatnot. You weren't looking to hire a person, you were looking for a specific outcome on your website, and you felt that that one product could provide you that outcome. And once you had that outcome, you're happy.

And that's exactly why product shops are, in my mind, have to be customer oriented first because all of the success, all of the success of the product, of the marketing, of the business, all starts with whether or not the customer is happy.

[00:13:05] Nathan Wrigley: Yeah. We have this expression in the English language which is, a rising tide carries all boats. And essentially what it means is, when there's this sort of groundswell of growth, everything touching it grows. And I think we had that in all sorts of ways recently, over the last decade or so.

The mobile phone app ecosystem, that just was taking off and all the developers over there were doing incredibly well. Same with the WordPress space. Just year on year growth. And so there was this notion, which you reference on your website quite a lot, of build it and they will come. And that phrase essentially is, okay, I am one of those people. You said, nerds.

I'm going to build a product, and I have a complete expectation that I am part of that rising tide. I'm one of the boats. I'll build this thing, I'll mention it a few times on social media, and this thing that I've spent hours and hours doing will take off and I will be able to have some kind of passive income from it.

Now, I don't know when you started saying that those days were gone, but you are definitely saying those days are gone. Why are those days gone? What happened? What changed to make it so that the rising tide carries all boats analogy, possibly no longer fits?

[00:14:17] Matt Cromwell: It depends on the context. I mean, it fits in several different ways. But when it comes to product in the WordPress space nowadays, we used to depend so much on the wordpress.org plugin, or theme, directory as a primary outlet for discoverability. I want people to find that I exist and that I am a solution for their problems, and this is where you find me.

The plugin directory in particular, when we launched GiveWP, I think there were 30,000 plugins at the time, or approaching 30,000. And now there's over 60, and they are growing every day more or less. They grow and they shrink. They get rid of plugins too, actually. But that does increase the amount of surface area where you have to break through in order to be found. If you try to be an AI alt text generator right now, good luck. There are three dozen of those that got shipped yesterday. It's crazy.

But even more so than just the noise and the volume on the plugin directory, it's also that the consumers that are building their websites, they are not thinking about WordPress as much anymore. They're building with WordPress, but they kind of don't care that it's WordPress. They're just building a website. They have specific outcomes and they know that there are lots of products out there that can serve their needs, and they don't care if it's a SaaS, or a platform, or a plugin, or a theme. They don't care. They're just going to look for that outcome and they're going to plug it into their website in one form or another, if that solution is pluggable.

And that space, the SaaS space in particular, has gotten a lot more crowded and a lot more competitive for being applied directly to the WordPress customer. So we're not just competing WordPress to WordPress, we're competing WordPress to the rest of the whole world.

[00:16:18] Nathan Wrigley: Yeah, that's interesting. So my analogy, when I said a rising tide carries all boats, what I'm imagining 10 years ago is that there was a really nice looking harbor with a few little boats. And the tide came up and these little boats just bobbed along and they all rose up. Whereas now it feels like the harbor is just chockablock. There's boats cheek by jowl with other boats. They're slamming into each other. And instead of it being a gentle rise, it's stormy, clouds. The sea is choppy all over the place, and everything is sort of bumping into each other.

In other words, it's saturated. If you are going to be doing the alt text plugin for AI, well, there were six that came out this morning. There's going to be nine more by the time we close the doors this evening. Whatever it is that you are doing in the WordPress space, chances are somebody's already done it. They may already have an existing audience. They may already have paid subscribers.

So this all sounds very bleak. It sounds like we've got no way out of this. But your endeavor, what you want to turn your attention to in the years to come, is to persuade people that's not the case. So what is the rainbow? What is the shining light on the horizon? How would a plugin developer, a theme developer, somebody in the WordPress space, how do they cut through all of this and get noticed?

[00:17:28] Matt Cromwell: Yeah. A lot of things have changed over the years, but I would say the majority of things, when it comes to digital products, have not changed. And that's really the brass tacks of what it takes to be a winning product on the web in general. SaaS companies have known this for a really long time because they didn't have the obvious distribution channel of wordpress.org that we have.

So they knew if they were going to ship a product, they're going to have to market it a ton. In the SaaS space, there's very, very, very few just handy developers who are like, hey, I just built this cool thing, I'll just put it out there. And then all of a sudden it just goes off like crazy. It doesn't work that way, and they know it. And so they partner up with marketers.

And in the WordPress space, for way too long, we got lazy because we had the .org distribution channel. And we assumed that we could build it and people would come. And that's not like one hundred percent wrong. The directory is still a good tool, and it's still helpful, and I love the freemium model for products in general. But the thing that WordPress product folks in particular have to learn is to learn how to be a product business, not a code business.

And that's even more significant now that everyone is learning that code was never the product, because now nobody is building with code anymore. The humans do not build the code anymore. The machines build the code. And you'll find lots of marketers or CX folks who are building their own apps now as well because they're savvy enough to use the tools to be able to generate the code that they need and that they want.

[00:19:11] Nathan Wrigley: Can I just pause for a second there Matt, is that all right? Just because there's a couple of things that you said, and clearly for you it's common knowledge. You know, you've been in and out of this all the whole time. You painted a strong definition there between a product and code. What's the boundary between those two things? I mean, I think I can encapsulate, I just want to be clear that the audience know. What's the difference between product and code businesses, if you know what I mean?

[00:19:33] Matt Cromwell: Let's go back to when you said, I'm building my website and I have a problem that needs to be solved, and I see this plugin and it solves my problem. And I installed it, or I bought it and I installed it and it worked. That process that you went through, all of those things that you said, you never once said, I inspected the code to figure out if it was good enough or not. You never once said that. All of the things that convinced you to use that product had nothing to do with the code at all.

You went to the website and there was marketing involved that told you that we know what your problem is, and we know how to solve it. And there was a checkout experience that was calm and soothing enough and giving you enough confidence that they're not just stealing your money. Then you installed the product and there was a user experience involved that made you feel like it's actually going to solve your problem, and then it did actually solve your problem. All of those things cannot happen without code, but that is what a product does. And that's a product experience, is the whole entire customer journey that happens from discovery, to purchase, to adoption is what a product is actually made of.

[00:20:43] Nathan Wrigley: So I'm going to infer from that then that from the year 2026 and onwards, what you are saying is that the focus now needs to be on the product. More than ever, the product and the way that you market the product and the way that you pitch the product, and all of the things that wrap around the sales process and the discovery process of the product. That's where a significant amount of the effort needs to go once the code is in place. Have I parsed that correctly?

[00:21:11] Matt Cromwell: Yeah, I might even go at it from the perspective of the customer because you only understand the product when you look at that whole thing through the lens of the customer. If you think about everything from, oh, I can build that, I just need to pipe these APIs and do this kind of thing, and then you get the outcome, it's like, well that's not really what the customer's ever going to experience.

They're going to experience a website first. They're going to try to have trust first. Look at the whole thing through the customer lens and then you'll start to understand your product. I mean, you'll understand your brand in the first place. A lot of WordPress folks don't think about brand particularly well either. They just name it like Advanced Custom Fields. Now, I love that product. It's a great, but it's one of those things where like, let's just name it what it is. Okay, I guess.

[00:22:04] Nathan Wrigley: So this is really interesting. So presumably then, if product is the way forward, it feels like you have now kind of invented a new career angle for yourself where you are going to hopefully kind of helicopter yourself in, or be helicoptered in, to businesses who maybe have got this product bit missing. You know, there are bits of that they, I don't know, maybe they feel that they're weak on that, or that past endeavors haven't really worked out. Or maybe they're at the first step of that journey and they just want to try and figure out what direction they should point themselves in to have some success.

So that's kind of interesting. That's the role that you are going to be taking on in the future. And I can see you nodding. Dear listener, he's nodding away, so that's good. But, do you have like a one size fits all template here, or is the endeavor very much to be, okay, I'm going to go in, have a long listen, figure out how you differ from the other people that are on my roster? There's not really a question in there, but I'm kind of asking you how you are going to position yourself for the different clients that you're no doubt going to be taking on.

[00:23:06] Matt Cromwell: Yeah, yeah, Well, one thing I'll caveat a little bit is I'm trying to position myself towards two related audiences. The primary one, for the fractional CGO, is the teams. Product shops that are a team of people. A small team, medium sized team. They've built something, it's successful, they are paying employees, but they're looking for that next level up, in order to start growing into what they hope to be, more sustainable growth in the long term.

The other one is what I call the solo lab, where I am trying to position more towards solo individual founders who are by themselves and maybe just got their product out the door and are trying to grow from the ground up. That's more of like a coaching environment and it's a group environment and things like that. But both of them are, it's not that there's a, I don't believe really in playbooks. I don't believe in silver bullets. I believe in process and diligence.

And that's what I am trying to bring in both of those circumstances is I help the solo folks understand the type of activities that they have to force themselves to do. The solo folks typically are very dev oriented. They know how to build more things. And if you ask them to write a blog post, they're like, okay, I'll do that tomorrow and tomorrow never comes. You know, helping them to focus on the work that they have to do to grow their product.

While the teams, it's more generally about, they have founders who have done all the things. They have been the dev, they have been the HR lead, they have been the marketer, they have been the support guru. They've done all of it, and they're just tired. And they need the growth but there's just a missing gap. They need somebody to kind of put on the hat of, you are going to be responsible for finding growth in this team, so that that founder can focus more on other parts, the things that energise them more.

[00:24:59] Nathan Wrigley: I'm curious as to whether or not, when you were doing the busy work of being at GiveWP and then StellarWP, whether you drew the intuitions that you are now going to be helping people with. Whether you were aware of this in your head, or it was just the busy work that you were doing. You know, day in, day out, you do this task and over the decade or more that you were doing it, you just kind of perfected it. And, okay, when this thing arises, I do this thing. And when this thing arises, I do this thing.

Now I expect you're in that curious position where you are having to lift yourself away from the whole process, stare back at it, and sort of examine how you would do it with a third party. Again, there's no real question there, but I'm curious as to how different that is for you being the outsider, but relying on the insider knowledge that you must have acquired over time.

[00:25:49] Matt Cromwell: Yeah. I think that's one of the reasons why I felt a certain amount of confidence in moving in this direction is because I'm helping people that are in the position I was in years ago. I've been there and I have done that, and I have absolutely failed. And I don't have a perfect record or a perfect playbook, but I know what it's like, and I have done the hard work to see successes.

I think what also makes my experience a little bit unique is that I had the experience of GiveWP and I honestly, going into being acquired and working at Liquid Web, I had that whole feeling of like, what if I'm a one hit wonder? What if I like did a great job with Give, but I try to apply this anywhere else and it just is like, well you got lucky with Give, that doesn't work anywhere else? And it turns out that most of the things that I learned can be applied to other products with success as well. It does give me a fair amount of confidence that I do believe I can be helpful with these other shops.

[00:26:50] Nathan Wrigley: You're not sort of saying there's a formula, you know, that kind of snake oil mentality. But there are wise things to do and less wise things to do. Let's just put it that way. And by repeating the wise things over and over again, you give yourself kind of a fighting.

[00:27:05] Matt Cromwell: Yeah, and there's a process and there's also the ability to form smart priorities. That's, I think, a lot of what I'm trying to help provide is being able to help founders learn how to say no to a lot of things. Because sometimes, especially when it comes to anything that's growth oriented or marketing oriented, we see a million opportunities. And so then we start dabbling in all the things because we don't know what else to do.

We're like, oh, there's like, I can go and jump into Reddit and find a whole bunch of leads, or I can like spend a bunch of time on LinkedIn, or I could write a whole bunch of really good emails, or I can maybe do a paid ad campaign. And then we start doing just like a million small things. But that doesn't lead to growth, you know? So the ability to prioritise around growing rather than noise and activity.

[00:27:57] Nathan Wrigley: I think it's just really nice to be able to put down the scatter gun. You know, that thing that you're firing tiny pellets in a million different directions. But you put the scatter gun down because somebody says, put the gun down because that's not effective, and here's why it's not effective, and here's some things that you could do to try which might be more effective.

There's just something nice in listening to the words of wisdom coming out of somebody else's mouth who's obviously been there, done that. It's kind of hard to put that into words, but just knowing that somebody's got your back, and that somebody's been through that before. And the million, gazillion little things that you are trying without a great deal of success are things that you can put away and listen to your advice.

I feel that you've hit a real vein of, well, let's go fruit. You've got that in the title of your business. And the reason I say that, and I've said this in this podcast a few times before, it really does feel like there are an awful lot of people who have done the code side of things in our ecosystem. They are, as you've described, you know, you used the word nerd or something like that. They have built this thing with very little thought for the business side of it because WordPress, for many people, has been like this sort of hobby thing, this passive income thing, this side gig kind of thing. But they don't know how to do it. And I get email, no doubt you get email, and certainly will be getting email, about this kind of thing. And so I feel that there is a real undercurrent of people who hopefully will tap into your service. Let's hope so anyway.

[00:29:29] Matt Cromwell: Yeah, let's hope so. So far, so good. I've already secured a couple folks.

[00:29:33] Nathan Wrigley: In which case, we're sort of around the half an hour mark, which is exactly perfect. So I will just point the people to the domain once more. It is rootsandfruit.com. Go check that out. Where would we find you, apart from the contact us form, which no doubt exists on that website? Where might we find you elsewhere online, Matt?

[00:29:52] Matt Cromwell: I have been on LinkedIn a lot. So look for Matt Cromwell on LinkedIn. You can also look for Roots & Fruit on LinkedIn. That's kind of where I prefer, but I'm also on the nefarious x.com as learnwithmattc.

[00:30:06] Nathan Wrigley: Well, good luck with the new adventure, Matt. I really hope it works out well and, yeah, speak to you soon.

[00:30:12] Matt Cromwell: Thanks.