Progressive Beveling

California tried to protect students’ data. Tech companies found loopholes

A legislative battle is under way over gaps that allow companies to collect and sell students’ personal information.

For every aspect of a student’s life, there’s a tech company trying to digitize it. Inside the classroom, online tools proctor exams, create flashcards and submit assignments. Outside, technology coordinates school sports, helps bus drivers find the right route and maintains students’ health records.

California has a number of laws aimed at protecting children’s data privacy, but those laws have exceptions that allow many tech companies to continue packaging and selling students’ personal information.

This year, Assemblymember Dawn Addis, a San Luis Obispo Democrat, is carrying a high-profile state bill that would add new protections for students. She says it’s important, especially as the Trump admin is trying to collect data about California residents’ immigration status, gender identity, and their use of certain public benefits.

Historically, California has been a leader in data privacy. In 2014, California passed a landmark student privacy law that prohibited technology companies from selling students’ data, targeting students in advertising, or disclosing their personal information. Then in 2018, the state passed another unprecedented bill that required all companies give California users certain privacy rights, such as a chance to opt out of data collection and delete some of their information.

But as technology evolved and proliferated, privacy laws repeatedly fell short in protecting California’s students — at the same time that the federal government has tried to collect increasing amounts of personal information, Addis said.

Her bill would restrict how AI companies use student data and create new data protections for college students. Some of Sacramento’s most powerful players are paying close attention to the measure, including the California Labor Federation, which supports the bill, and the California Chamber of Commerce, which opposes it. Combined, these two groups spent nearly $8 million on campaign donations to state legislators or other political activities in 2024, according to the CalMatters Digital Democracy database. TechNet, a trade association that represents many of the most powerful tech companies, also opposes the bill.

The proposal, Assembly Bill 1159, would close certain loopholes in the state’s 2014 education privacy law, but experts say it may not be enough to prevent companies from selling students’ data.

A privacy expert struggles to keep her information private

Jen King is a privacy and data policy fellow at Stanford’s institute for AI, where she studies the tricks that companies use to gather users’ data and prevent them from opting out, sometimes known as “dark patterns.” In her personal life, she’s vigilant about avoiding online data tracking and maintains a landline in her Bay Area home to avoid giving out her cell phone number.

King doesn’t want her children’s information available online or for any company to sell, though sometimes it happens before she can stop it.

In the fall, King got an email about a platform called TeamSnap, which her 12-year-old son’s cross country coaches were using to manage the team’s roster. The company wanted her information, including her name, date of birth, gender, email address, and phone number. Once she logged in to the platform, she could see some of her son’s information, such as his name, email, and date of birth, were already listed. Photos and personal information from all of her son’s teammates were also available for her to see.

“I was super irritated,” she said. “You don’t need my birth date — I’m a freaking parent.” She acknowledged some personal information could be useful for a coach but said that other questions seem designed to help the platform sell information to data brokers and ultimately, to advertisers.

Her 17-year-old son’s data is also on TeamSnap, she later learned, because his robotics team uses it. This month, when King tried to show The Markup and CalMatters her TeamSnap account, a pop-up appeared, asking her if the company could track her activity across other apps and websites.

Federal law requires companies to get parental consent before knowingly collecting or selling data from children 12 and under, but once a child turns 13, their data is generally treated much like an adult’s information, especially when that child is interacting with tech platforms outside of school. TeamSnap’s privacy policy says it doesn’t knowingly collect personal information about users under 13 “without express parental consent,” though it says in some cases a team or organization may provide information on behalf of the child.

The policy also says that TeamSnap has “not sold the personal information of any consumer for monetary consideration” in the last 12 months, but that its “use of cookies and other tracking technologies may be considered a sale of personal information under the CCPA (California privacy law).” Information sold to advertisers and marketers included users’ names, contact information, purchase history and geolocation, the policy says.

California privacy law specifically requires certain large for-profit companies to get consent to collect data from anyone under 16. Often, consent happens when a user first opens a website and a pop-up appears, asking if the website can sell your data or track your cookies.

If a teacher, coach, or other authority figure tells a student that they have to use a website or an app, then the student cannot realistically opt out, King said. They may be too young to understand how to opt out, she added. “Most 15-, 16-year-olds don’t have any idea what this is about.”

Even older college students may have little agency in the technology they use, especially if it’s required for class or residential life. At Stanford, for example, King said her undergraduate students are often required to create Facebook accounts for student groups.

The same is true for parents. King said she reluctantly gave TeamSnap her personal information, including her name, email, date of birth, and the landline number for her home, because it was the only way to get updates about her son’s team.

How companies get around California’s education privacy laws

In 2014, California became the first state in the country to regulate education technology companies directly, but being first comes with its drawbacks. “We didn’t have examples of what best practice was,” said Amelia Vance, the president of the Public Interest Privacy Center, a nonprofit organization. The law only applies to products that “primarily” serve K-12 schools and that are designed and marketed for students.

Many tech companies argue that their products aren’t primarily intended for students or at least that they were not designed or marketed that way. The language-learning app DuoLingo, for example, has a version for schools, but the app is also popular for adults. Apps or technologies serving extracurricular programs or sports teams can claim they weren’t designed and marketed for the classroom, or that their use isn’t mandatory, said Vance. “You have this sort of black hole where there haven’t been protections.”

Addis’ bill expands the number of education technology companies that fall under the state’s student privacy laws, but the language is murky when it comes to apps or online services used outside of class.

In the case of TeamSnap, Addis’ communications director Alexis Garcia-Arrazola said the company would “most likely” fall under the scope of the bill if its technology is marketed to schools, if schools direct students to use it, and if the sports team is sponsored by the school.

Public records show that Piedmont Unified School District in Alameda County, Tamalpais Union High School District in Marin County, and Santa Monica Malibu Unified School District all purchased versions of TeamSnap, but only the Santa Monica Malibu district responded to questions about any privacy restriction imposed on the company. Brandyi Phillips, the chief communications officer for the Santa Monica Malibu schools, said the district has an annual subscription with TeamSnap, which is only available to sports staff and parents. She said there’s an agreement with the company “to protect District information and to prevent unauthorized access” but did not clarify if that agreement prevents the district from selling students’ information.

Berkeley Unified School District, where King’s children attend school, did not respond to questions about any contracts, purchase orders or agreements with TeamSnap.

Locally, school districts and colleges have the power to negotiate the privacy terms of any contract they make with a technology company, but many websites and apps offer free versions that a teacher or coach might recommend without getting formal approval from their district.

Last year, the California State University system signed a nearly $17 million contract with Open AI, the company that operates ChatGPT, including an agreement that the company will not train its models on student data. Advocates for Addis’ bill say the same privacy restrictions should apply to any AI company with access to California student data, regardless of whether the company has an agreement with the student’s school district or college.

Are privacy laws getting stricter or looser?

Addis’ bill comes as privacy laws in California and across the country are in flux. In 2020, California voters approved a proposition to create a new state agency to enforce data privacy rules and regulate the businesses that collect data. Advocates for the proposition contributed over $6.7 million to the campaign, compared to just over $50,000 contributed by the opposition, according to state data. The state agency that the proposition formed, now known as CalPrivacy, released new rules this year, restricting the use of automated decision-making technology, such as the use of AI to make admissions or hiring decisions. Those rules were originally stricter but businesses, lawmakers and Gov. Gavin Newsom pressured the CalPrivacy board to water them down.

In Washington D.C., Congress is considering changing federal law to limit how companies interact with children under 17. Separately, Congress is considering a bill that would require social media companies to prevent and mitigate children’s sexual exploitation, bullying, and self-harm. California Attorney General Rob Bonta is concerned that one version of the social media bill contains language that could erode existing protections in California law.

Bonta’s office is responsible for enforcing many of the state’s existing privacy laws. In November, he said the state worked with Connecticut and New York to reach $5.1 million in settlements against Illuminate, an education technology company that uses data to track and evaluate students’ progress, such as their testing scores and developmental milestones. The company had a data breach, exposing “sensitive information” from over 434,000 California students, the state attorney general’s office said in a statement.

It was the first time California successfully went after a company for violating the state’s landmark 2014 education privacy law.

To increase enforcement, Addis’ bill contains a new provision — the right for students and parents to sue tech companies in certain cases for privacy violations. Business and technology groups have opposed the bill, arguing that the new regulations and the right to sue would stifle investment in AI-powered learning tools.

King said that giving consumers the right to sue is often the only way to increase enforcement. Otherwise, the onus is on individual consumers to find concerning practices and try to opt out.

Despite being an expert in data privacy, King said that she struggled at first to figure out how to delete her TeamSnap account, only later to discover that she needed to send an email to the company. She laughed at the irony, since it’s these kinds of dark patterns in user design that fuel part of her research.

In academia, the strategy of trapping customers is sometimes called the “roach motel,” she explained, a reference to a popular television ad from the late 1970s for a cockroach trap.

“You can check in,” she said, “but you can never check out.”

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#205 – Matt Cromwell on Redefining WordPress Product Growth in a Crowded Ecosystem

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 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.

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’ 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 prioritise growth efforts, refine their product experience, and avoid the scattered approach that many developers fall into. He brings practical insights from years of hands-on experience, and explains why a successful WordPress product business relies on process, diligence, and wise prioritisation, not just code and hope.

If you’re 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.