Transcript [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