#### Introduction

Jesse Friedman: Welcome to Impressive Hosting, where we uncover the core tenets of great WordPress hosting. I am your host, Jesse Friedman. Before we dive in, remember to check out impressivehost.net. It’s where you can comment on episodes, ask follow-up questions, and submit questions for upcoming guests. You also find all our links to follow, like, and subscribe wherever you listen.

With me today is Jamie Marsland, the head of WordPress YouTube and a fellow employee here at Automattic. Thank you so much, Jamie, for joining. I wanted to have you on because I feel like you’re doing so much work to educate the public on how to use WordPress and how to be successful with WordPress, and I wanted to see what we think hosts should be doing around that. And so that’s what we’ll be diving into today. But in the meantime, tell us a little bit about yourself.

Jamie Marsland: Well, hello. Thank you for having me on. I’m Jamie, as you said. I’m head of WordPress YouTube, working at Automattic now. Prior to that, I ran my own business which is a company called Poodle Press, where we did—I started that business doing WordPress training. That’s my kind of core background. So actually over the past, I guess 12 years, I’ve trained over 5,000 people face to face in rooms on WordPress.

So I deeply understand beginners in WordPress and the travails they have using WordPress and the joy they have and how life-changing it can be for them. It’s in my DNA because I’ve sat in rooms with people and trained thousands and thousands of people. And then I also developed a plugin business throughout that process as well. And prior to that, I ran a publishing business, so not my business, but I ran a publishing business online, but also print. And prior to that I ran a marketing services business. And prior to that, I was involved in a publishing business. We’re going back to quite some time, so I’m steeped in publishing. I’m passionate about publishing on both sides of it, both actually running a publishing company, but also kind of providing services to publishing companies as well. And so WordPress is in a perfect sweet spot for me. That was a bit of a roundabout, but hopefully it gives you an idea of some of the stuff I’ve been up to.

Jesse Friedman: Yeah. That’s quite amazing. So your history with publishing, how long has that been WordPress related?

Jamie Marsland: So yeah, pretty much. I’m gonna say, so at my last business I first found WordPress ’cause I was running a publishing business. And we were using a .NET platform called Ektron, which you probably haven’t heard of, but it was a CMS and we’re going back 15 years here at least, probably 15, 16, 17 years. And that was at the low end of the CMS market, but we were still paying I think $5,000 per site, per year just to use the software. And I had a very good but quite expensive development team working for me, developing, basically building out the core CMS, and we were doing online publishing systems, things like business directories and things like that, which we were monetizing. But it was taking a long time to build that stuff out.

And then I discovered WordPress, kind of in my garage one weekend, and then I discovered kind of plugins in one weekend, and I discovered that I could build very quickly kind of what we were building that was taking months to do in Ektron—don’t even know if Ektron is still going—but I could do it in like a few days, whereas my very expensive, but very good development team was taking an awful long time to build basically the same thing. And so I got really kind of tuned into WordPress and fell in love with it very quickly and started to bring that into certain pockets of the business where we started using it against certain friction, I guess what you would say in the business because they were very purist .NET and whereas WordPress kind of was PHP and they looked down at PHP for all sorts of reasons.

So went through that journey, discovered WordPress, brought it into that business. And then when I vacated that business, I kind of thought, well, there’s an opportunity here. WordPress wasn’t just emerging, but I could see kind of where it was going. They gave me a lot of money to basically go on garden leave. So I had a period of time to think about what I wanted to do next, and I started looking around the market and there were folks out there running WordPress in a day courses, aimed at corporates, and they were charging, I think about 595 pounds per person per day. And I had the sense that there was this emerging DIY market hitting WordPress. So I literally took out a Google ad—

Jesse Friedman: Roughly what year was this?

Jamie Marsland: Well, I’m gonna say it was 16 years ago, something like that. It was a long time ago. I took out a Google ad and literally, I still remember the moment I was driving down the motorway with my wife to go and visit her mother and checked the phone and literally got an order in for my first person on a training course, I charged like, I think 99 pounds per person. And from that point on, I was just booking out classes and I was traveling all around the UK hiring out meeting rooms and even pubs. I did them in pubs. I was trying to get as cheap rooms as possible so I could get like 15, 20 people in a room. And then I developed this WordPress in a day course, which I ran for years and years.

That’s how the business started. Literally one Google Ad, one order, the most exciting order of my life. Having been in corporate life where you do big deals and, you know, 40,000 pounds selling systems into companies. Whereas this was 99 pounds and it was still the most exciting order I’ve ever had ’cause it kind of told me there’s a market and there’s money in the hills. And then I was off to the races then it was just about scaling it, and that’s kind of what I did.

Jesse Friedman: That’s amazing. That’s a marathon starting with that first step. That’s great. I remember those days with .NET. I actually had a client, or rather a company I worked for that was using a .NET closed source CMS. And I remember the days of having to convince people to switch to WordPress and open source. And there was this weird paradox where, of course, money was top of mind for them. They wanted to save money. They didn’t want to—every time you shared a budget with them, they always wanted it to come down a bit. But then, you know, when you shared an open source project like WordPress, all of a sudden it’s free. That was questionable. That was a little scary to them. And there was a paradoxical thing there where you had to kind of like convince them that free is okay. And I think the question they always came back with was like, well, who’s supporting it? Who’s running it? Who’s building it? Like how do we get new features and how do we know it’s gonna be around in 10, 15, 20 years?

#### How has WordPress education and adoption changed over time?

And I don’t think we have that conversation as much anymore. Maybe in new verticals or different industries, maybe in the government or something like that. But I don’t tend to have to explain WordPress or open source to folks as much.

Jamie Marsland: No, it’s definitely shifted into different areas as well. But yeah, that friction’s kind of gone as far as I can see. And it’s kind of well established in the enterprise market now, and government supports open source as well, so it’s like you don’t have to educate the market so much.

Jesse Friedman: That’s true. And so you said that you’ve taught thousands of students and this was in person. What was the actual like location? Was this a college, was it a studio? Was it a library?

Jamie Marsland: I would literally do them around the UK, so I did them in Scotland, Wales, London was obviously a big market and I would just try and get the best deal for the—’cause the price point was very low, so I was charging like, you know, sub hundred pounds per person trying to get like 15 people. So you’ve got the—the key to the business was trying to get the meeting room cost as low as possible. So I spent an awful lot of time just training around London going into, I mean I ended up going into pubs and saying, look, have you got a nice meeting room? A lot of these old, lovely London pubs had nice meeting rooms with good wifi.

So, yeah, I would get trains at like, you know, five o’clock in the morning, traipse off with my projector in a rucksack, laptop in rucksack, praying that the wifi was gonna work that day. Have all sorts of backups in place. I had these little MiFis I remember now that I used to take around just in case it didn’t, and I ran—I set up each person’s site on a multisite, I think back then. So yeah, it was a cool business and a real privilege too. For a lot of people, this was really life changing because these websites were—they weren’t just, you know, blogging about their cats. These were running businesses and enabling them to really change lives.

Jesse Friedman: So these were people who were trying to build a website for their own business, their own needs, not like educating someone on how to become a freelancer and build websites repeatedly.

Jamie Marsland: We did have a mix here, but I would say probably, actually a few interesting things, and this is all anecdotal, but I would say it’s probably 80% DIY is 20% agencies. I also had some people that came on the course that really looked at my business and loved the idea, so then they went off and actually set up their own WordPress training businesses, which was kind of interesting to see. And I had this one guy, he actually, he came on the course and then he kind of launched this website and he literally just verbatim copied my entire sales page to the point he was too lazy to even put his own phone number on there. So he actually just copied my phone number. So I was getting these calls from people saying, I want to come—I’m gonna make up his name—I want to come on Jeff’s WordPress course. I was like, well, you’ve called—you called me. That’s how lazy he was.

Yeah. But I would say it was 80% DIYers people setting up their own sites. And the rest was kind of agencies that are looking to move to WordPress. The other interesting thing that happened was when I started, it was probably demographically, I would say, 95% men coming on the course. By the time I’d kind of stopped ’em now since I joined Automattic, that had kind of flipped, which was really interesting.

Jesse Friedman: Oh wow. That’s great. So it wasn’t even just a minor, like a small majority, it was a significant majority of women joining the classes to learn.

Jamie Marsland: Absolutely, it completely flipped and, um, I don’t wanna be too reductive, but they were definitely the better learners as well. They were definitely more open to listening to advice, whereas I’m being too reductive now, but sometimes men come to those situations with preconceived ideas of how it should work. So yeah, we saw that shift as well.

Jesse Friedman: That’s a funny thing because I taught at two universities for almost eight years, and I had probably hundreds if not thousands of students. And I taught a variety of classes from JavaScript to Flash to WordPress. And you know, so one of the things that I think is really quite amazing is when you run into a former student at like a WordCamp or something, and they run up and give you a hug and tell you they have this whole career that’s come of it. But when I started teaching back in 2005, 2006, I would definitely say that the vast majority of students were male. Now when I stopped teaching in 2014, 15, it was not a flip, but I would definitely say that there was a lot more women taking classes and focusing their energy in that area. And I think that overall computer science started shifting in that direction.

And it’s, you know, maybe now I’m a father of a 17-year-old daughter, not for one second did I ever think that she couldn’t get into computer science or never wanted to not steer her in that direction, if that was a passion of hers. It’s funny to think that just 20 years ago, even less than that, we were still trying to shift that mentality that women should not only be moving into this field but are more than welcome to be doing it. It wasn’t top of mind, I don’t think as much back then, even the University recruiters I think would tend to lean towards male students and promote computer science classes to them over female students.

Jamie Marsland: I think the job market probably was driving some of that change as well. In the UK in particular where I think a lot of the websites that folks were setting up were like side hustles. And so this was a way to kind of supplement family income. That’s, again, it’s very anecdotal. But I read this amazing stat the other day. There was something like in the UK something like 50% of people are looking to start or have a side hustle. So the side hustle market’s really enormous and can be like selling clothes through things like Vinted and things like that, but it’s also setting up your own businesses. And I think that’s going—I mean, we might come onto this, but I think that’s a huge—we’re gonna see an explosion of that stuff, especially around the AI and the opportunities that’s gonna give many, many people. Now I think we’re gonna see that even multiply more. But we’ll see.

Jesse Friedman: Yeah, I hope so. And I hope that it moves away from enabling of large conglomerates. Like I remember when drop shipping became a side hustle that everybody was getting into because you could leverage things from Amazon and other tools to help make some money, but at the end of the day, you’re just kinda giving a large corporation like Amazon a leg up. You know, I love the idea of side hustles becoming more prevalent and people being able to explore their passions and make money off of that, whether that’s selling clothes or art or whatever it might be. And WordPress is definitely gonna continue to empower people there.

So nowadays you’re teaching in a different format. You’re not teaching people physically face to face, maybe not as much. You probably still go to WordCamps and other things like that. Do you still see the same kind of focus in terms of the demographic of students? Like, are they still people building for themselves, trying to get something launched so that they can get back to work on their business or whatever their passion is?

#### What are some best practices for WordPress education?

Jamie Marsland: Yeah, I guess the bit I missed out of the intro is over the last three years, three and a half years, I started a YouTube channel actually before I joined Automattic. And that’s now about 178,000 subscribers. So it’s grown—that’s been really successful and that whole journey has been incredible but I think obviously the teaching for 15 years has really made that kind of—I know the pain points that people have. So when I approach a video, I kind of, in my DNA, I know how to hopefully teach it in a way that’s succinct and useful.

At some point with YouTube that was generating more revenue than my business, which was like, that’s weird. And when you get to my age and people say, what do you do? And you say, well, I’m a YouTuber. That’s weird. But you’ve grown to accept that. And the other interesting thing that’s happened is now I still get lots of—I mean, I paused my sponsorship since joining, so I don’t do any new sponsorships. But I would say 99.9% of all sponsorship offers ’cause I still get quite a few every day coming in are AI companies, which is, you know, there’s obviously a lot of cash going into AI at the moment. But I’ve seen that switch as well. I haven’t answered your question at all.

So yeah, creating content on YouTube is very different to teaching in person, but you still get the same thrill when you get a lot of engagement. So some of the videos get an awful lot of engagement and you know, the beauty is I still got comments from a video I made two years ago where someone was saying thank you, that’s amazing. I wish I’d seen this. And it’s changed everything for me. So you still got the same thrill. It’s slightly different. I actually ran a training course face-to-face in Barcelona a few weeks ago at the Off Conference, and it just reminded me of the incredible—doing them in person is just such an incredible feeling when you get that instant reaction. So I wanna do more of those going forward.

Jesse Friedman: Yeah. That’s fantastic. So these students are finding the YouTube channel, they’re probably finding it through YouTube search, Google search, other things. What about the way in which people are introduced to WordPress? Do they kind of find WordPress and then your channel and your videos like in parallel or are hosting companies actually pushing people to look at YouTube and other channels to help educate their customers?

Jamie Marsland: I think they are finding—it’s quite interesting. I mean, the way that the YouTube algorithm works, clearly you get some people through search, but the way kind of the algorithm works is, and obviously most of my content is WordPress oriented, but it’s starting to broaden out into more sort of AI and more sort of design type stuff as well. I think your question points at the role of hosting companies and what they can do in terms of pushing people and helping with WordPress as a YouTube creator.

One of the challenges of a YouTube creator is WordPress hosting or hosting companies have a lot of the money. They are the source of revenue, so they want to do content for you, but actually creating content around hosting is very difficult and I’d be interested in your view on this—it’s like a black box for many people. It’s just this thing that happens somewhere, which we have no real idea of what it is. So as a content creator, when a hosting company wants to give me lots of money, which lots of them did or do, actually creating content that’s gonna be interesting for people is a real challenge because hosting is a very nebulous thing to try and get your head around as the market of my videos where people might wanna watch my videos, if that makes sense.

Jesse Friedman: Yeah, no, it definitely does. It’s something that we keep exploring on this podcast over and over again is what is the way in which we’re framing hosting. You know, years ago you used to—you go to WordPress.org, you download the latest version of WordPress. You’d have to upload it to some server somewhere, which meant you had to acquire hosting. And that was the process in which you would build a website. Now we’ve closed the gap, we’ve created the five minute install, and now we’ve gone even beyond that, where hosting companies just sell a WordPress instance on a box somewhere.

And I think that as we move away from—and we get a larger distance between the old ways of doing things and this newer way of doing things. And now I think we’re gonna see even like a faster acceleration with AI. I think people are getting away from the idea of even thinking about hosting. And this is something that I actually wanted to ask you is that, you know, when you think about this audience, this core group of individuals who have some other passion, something else that comes up on this podcast a lot too is that, you know, you’re running a business, you’re running a blog. You’re doing a side hustle. The actual work of building a website is probably not your passion. It’s a means to an end. You’re trying to get something up and operational so that you can sell something, distribute something, teach somebody something, and so you are trying to acquire these skills just in order to get something live.

And so anytime that we can close the gap and make decisions for customers and help to speed things up, it tends to help them move in a more positive direction, helps things go faster. And so you eliminate a lot of these steps around hosting. You don’t have to make decisions around, you know, how many CPUs you need or how much storage you need, or whatever. You’re just selling WordPress. And so then in that case, like, you know, if you’re thinking about the way in which you’re communicating or teaching individuals to choose hosting, maybe it becomes less about choosing hosting, and it’s more about—you know, if you have a base set of standards for hosting a certain amount of reliability, uptime, speed, security, then what does it become after that?

#### How should hosting companies evolve to better serve WordPress users?

It’s the tools that they provide on top of it, it’s the add-ons and the bundles that they include in it. It’s the support that they provide to the customer, and that becomes much more focused on a holistic system to help you be successful online and less about the actual box that you’re hosting your website on. So, you know, I think shifting towards helping people to be successful and hosting just happens to play a part in that, is probably gonna make a lot more sense in the future.

Jamie Marsland: Yeah, I mean my DNA, I’m a big advocate for the DIYers and the people that wanna self build their website. So when I go to a pricing page on a typical hosting company, I’m amazed how complex it is and, you know, for somebody that I’ve taught, they don’t want to know any of that stuff really. They almost don’t wanna know any of it. And the big issues they generally have are like linking a domain name to their website, setting up email with their domain names is a horror show for a lot of people that’s very painful. So there’s all these points of friction that have historically been in the system, whereas actually for the end users, as you said they just want it to work.

And I think we’re starting to see that happen with things like the WordPress.com AI builder, there’s no hosting conversation—your first experience is actually building the website, and then the hosting just happens transparently and invisibly in the background. So actually the application layer becomes the thing that they experience. And the hosting is just a thing that we take for granted. It’s commodified and it should just work. So I’ll be interested in your viewpoint on how you then differentiate as a hosting company if this is where we’re heading.

Jesse Friedman: Yeah, well, I mean, I think that you have to look at the greater industry trends, right? So you look at Shopify or Squarespace, Wix, these closed—they’re not walled gardens, but they’re siloed functionality where everything is just built in. What that means is that they’re able to provide an experience for a customer that does not require you to make endless choices about the minutia of how to build the framework that lives underneath the website that you’re trying to build.

And so when you think about a person considering WordPress, they’ve probably been told, Hey, you have all this extensibility, you have all this freedom. You can do anything you want. It can grow from a blog into a store and you don’t have to rebuild it. And that can be very exciting and fun. But then all of a sudden, like, okay, so where do I go to get WordPress? Well, WordPress.org doesn’t solve the hosting problem for you. You can’t launch at WordPress.org. It has recommendations, but then all of a sudden, those recommendations can become daunting, right? You have to choose a host. You have to choose between thousands of plugins, thousands of themes, and these decisions can become, you know, as you said, daunting. They can become a major struggle for end customers.

So what we need to think about, and that’s why, you know, I’m very excited for that WordPress.com AI builder because it kind of exemplifies that idea of decisions, not options. Help us to understand what it is that you’re trying to build. Let us make some decisions for you, and then we can kind of figure out all the pieces underneath of it. And I think it would be wise for hosting companies to start to think about obfuscating behind the scenes stuff and just make intelligent, intuitive recommendations as time goes on for the most part. If you’re just getting started and you’re running a mom and pop shop or a retail store, even a brick and mortar, right? Like, and it’s kind of a brochure website, CPU power and resources and vertical scaling and all these other tools that might come bundled with your hosting, it’s not gonna be super important to you. And so you don’t need to describe that to them.

So what you could do is you could just get them started building a website sooner, kind of hide that layer, then when it becomes a problem, if they’re starting to run into resource limitations or they’re getting so much traffic, these are good problems to have and good problems to explain to a customer, right? And I think that’s something that becomes super important. When you’re communicating to end customers, is that the contextual relevance of the message that you’re giving to them, because there is so much information being thrown at them all the time, especially within WordPress. One of the things that WordPress really needs to improve is the way in which we have a kind of funnel communication from plugins and themes and hosts and everything into a singular path so that the customer can consume it in a way that makes sense.

But with all of that information being thrown at them, if you can eliminate the questions that you have early on that are not super relevant to you building a website and getting live. And think about it later and say, Hey, you know, over the last six months, you’ve grown from 2,000 visitors a month to 200,000 visitors a month. It’s time for you to think about performance and scaling and all those other things. Here are some options that make sense to you. And then you can really start to align yourself with the success of your customer, which is another common theme that we see in this podcast around the responsibility that a host has to their customers is to make sure that they’re not just selling something and kind of leaving it to them to figure out that you’re actually aligning the success of the host and their business with the success of that customer.

Because we need to move away from hosting companies being just a pure acquisition business, just trying to bring people in, because what we’ve seen is that you bring people in. When they churn from a hosting company because they had a poor WordPress experience, in their minds, they’re not thinking, I’ll go try it with another host. They’re thinking, I’m gonna go to Shopify, I’m gonna go to Squarespace or something like that. And that’s to the detriment of the overall ecosystem.

Jamie Marsland: I’ve been playing with a few AI tools recently, well a lot, like Lovable and Bolt. And actually I was just using Lovable for just a test and actually you build a site with that, you can add a custom domain, but you have no idea where it’s hosted. I mean, literally, and there’s no idea where you would get support for that hosting or if anything goes wrong, you’ve got no real support. You’re just left hanging. But it’s a very, very seamless experience. From the end user point of view, there’s no technical complexity.

#### Why is WordPress hosting so complex today?

Question back. I’m gonna ask you another question, sorry. I think, why do you think hosting is—’cause in my, if we’ve been really, really reductive around the kind of market we’ve got DIYers, then we’ve got agencies and they’re both incredibly important to the WordPress ecosystem. Why do you think hosting is so, I think that’s probably most, almost every hosting company you go to, it’s so complicated in terms of the language and the way it’s sold. Why do you think we’ve got to this? Why do you think we’ve got to this point where a huge market is not interested in that? Why are we where we’re at?

Jesse Friedman: It is a really great question and I’m not sure that there’s a singular simple answer that you can just point to, but my personal feeling goes from two pieces of our history. I mentioned before how WordPress required you to download the software itself and then go and find hosting somewhere else. The open source nature of WordPress and the fact that it allows for you to install that software anywhere and you can do it locally or you can do it on a server. You can buy your own server, you can AWS it, you can, whatever—that freedom then adds a layer of complexity, right? The same thing with the level of extensions that we have, the number of plugins that we have for WordPress, the freedom to install anything you want on WordPress also means that you have the complexity of increased security threats and outdated software and a lack of support and other things that you have to traverse.

And so one of the issues that we need to solve for, I think, with WordPress is that we need to identify that that is our history. It is not necessarily our future. And then the second part of this is that I think hosting companies are, and it’s a shame, but we are not great at segmenting customers yet. A lot of times, you know, it’s marketing driven. We think about the web as this place where people wanna make a lightning fast decision. You have to get them in the door. And we get very focused on acquisition and turning a viewer into a customer. But what would actually be really helpful is for us to do a little bit more discovery about the customer, to understand their level of expertise, what it is that they’re hoping to achieve.

Because if you’re running an agency and you know that your business relies on the reliability that your customers feel from the hosting company, you’re going to check out the specs, you’re going to look for—like, for example, like with WP Cloud, one of the things that we offer is automated real time failover. It’s a way in which we mirror a site onto another server. So if there was any kind of catastrophic failure, we reroute traffic in real time so that you never experience any downtime. To an agency or developer or a systems engineer, that type of technology is super important and very relevant. You want to educate them on that, but to an end customer who is a DIYer who’s just trying to get something live, the way in which you explain that is very differently. And you just talk about uptime, you talk about reliability at a much higher level, and you kind of abstract it and you say like, you know, your site just isn’t gonna go down. Your business can rely on this hosting company.

I think if we got to a place where we were doing a better job of segmenting those customers, we could explain things in very different ways and then have a better conversation, kind of personalized one-on-one conversation with these end customers. And when you get to a place where your DIYer is less interested in the technological underpinnings of what makes up a host, you can really drive them towards just building a site and getting things live. Whereas with an agency or a developer, you’re gonna get them into a panel. You’re gonna get them into a dashboard where you’re gonna help them understand the tools and the workflows they can build and things. It takes ’em down, you know, even though it’s built on the same technology, it takes ’em down a very different route. And so I think as an industry, hosting companies just need to get a lot better at doing that.

Jamie Marsland: Yeah, you’ve kind of triggered a lot of questions in my head. Is that right? If I ask questions? So one of the questions I had was—

#### Conclusion

Jesse Friedman: Uh, I want to hear those questions, but unfortunately, we’re at the 30 minute mark. You can’t believe how fast these conversations go, right. So if it’s all right with you, I think we’ll take a break and we’ll come back for a second episode and continue this conversation. I love what we’re doing here though. You’re interviewing me, which is rare on this podcast. But I love it. All right, well, thank you Jamie, and we’ll be back with a second episode shortly.