Do the Woo Co-Host Jonathan Wold from WooCommerce Unplugged

Do the Woo - A Podcast for WooCommerce Builders
Do the Woo - A Podcast for WooCommerce Builders
Do the Woo Co-Host Jonathan Wold from WooCommerce Unplugged

This is the last of the series where I ask my co-hosts to put on the guest hat. Today I chat with Jonathan Wold, who came on the show at the beginning of this year. As with my other co-hosts, Jonathan brings an amazing background to our show with his experiences in WordPress, WooCommerce and the bigger eCommerce ecosystem.

A Chat with Jonathan

In episode 74, I chat with Jonathan about:

  • How he does the Woo (seriously)
  • How his journey to both WordPress and WooCommerce were heavily influenced by the bigger eCommerce ecosystem
  • Commerce and its natural flow into and within WordPress
  • Learning from the guests the distinct differences between the WordPress and WooCommerce community even with overlaps
  • The users who are entering the WordPress space through WooCommerce
  • How publishing has a natural commerce component to it
  • Why shows with Matt Mullenweg, Nate Steward and Matt Gerri stood out for him
  • His professional and personal experience with habits, habit design and excecution.

Connect with Jonathan

Jonathan’s Top Episode Picks

Thanks to our community sponsor


The Conversation

Bob: Hey everybody, BobWP here, and we are back with, Do The Woo. You're probably getting tired of me because I've been the opening host for three shows in a row. The reason being is I've forced my co-hosts into being guests, so they don't get to open the show, they get to be hammered with questions that I have, and it's all good. I'm looking forward to that.

Before we get into our third and final of that series, let me just quickly thank, our community sponsor. We'll be adding a new community sponsor come mid-October, and we hope we have many more join us and Woo in this journey.

Just wanted to throw something out about WooCommerce. I don't know as a developer you've ever gone into the community chat, on their core channel in Slack. It's the last Thursday of every month at 1800 UTC. I've been actually just lurking there and watching it. It's fun because they talk about the updates coming in blocks and different stuff each month.

You're able to go in there and ask some questions. That's why I think it's just not good to hear about it or think about it. And you sure can go in and read the conversation afterwards, but the fact that if you're there at that time, you get to be part of it. You get to ask some questions to some of the brains behind Woo, rather than just letting those questions muddle in your mind and get unanswered. If you want to check that out, again last Thursday of every month, 1800 UTC.

Well, last but not least, or do you say, "You always save the best for last." There's several ways we can approach this one. Jonathan Wold, who you know as a co-host, is here today as a guest. Jonathan, welcome to the show, as a guest.

Jonathan: Thank you, Bob. It's great to be here as a guest.

How Jonathan really does the Woo

Bob: Well, as you know we start every show with our famous question. I found this particular series of episodes has made this question very fun to ask. Obviously, each one of you Do The Woo in a different way, but you obviously Do The Woo, but I always say, how do you Do The Woo aside from Do The Woo?

Jonathan: Well, I get the privilege of working in WooCommerce on a daily basis. I lead community initiatives for WooCommerce, and that touches a lot of different things where most of my time tends to be spent working with our meet-ups around the world, with our global community spaces, like our Facebook group, Reddit, Slack, et cetera, and then supporting initiatives that are happening throughout the community. I'm fairly involved in events, right now not so much, but looking to the future. Also involved in producing WooCommerce Live and anything that I can do to help support the community that's already there and then help it grow.

Bob: Excellent. All the hosts ahead of you, all two of them I should say, had quite a history with the WordPress, and then how they got into WooCommerce, and I know you fall right into that slot as well. There has probably been a lot of twists and turns. Maybe you can kind of take us back in time and tell us a little bit how you got into WordPress, and then fast forward or slip through those years to the point of your first experience with WooCommerce.

The history is a long and winding road

Jonathan: I got into WordPress, I'm going to probably butcher the time, but I think around 15 years ago, something in that. I'd been interested in the web for a bit, I'd been building on the web in different ways and shapes like HTML and experimenting with a few things.

WordPress forums mark the beginning of a great relationship

Then, I had a client who wanted a blog. I'd heard about WordPress at that point, did some looking around, and found the forum actually on I decided to use it and implemented it. Had a really key experience, though, early on. I got stuck on something and I posted a question to the forum. It was my first one there, and since we keep the archives it's still attached to my username, you can go back and find it. I asked for help and Matt Mullenweg jumped in, quite a few other folks jumped in, and kind helped straighten me out, pointing me in the right direction.

It really made a big impression on me like and this was back in WordPress 1.5, I think. These folks were willing to take time out and answer my questions. At the end of it, I just got this little spark of an idea that I should write about this and create a tutorial to document my experience. I did so, and I shared it afterwards and didn't think much about it.

Around a year or so later, I started to have people reach out to me who had found the tutorials that I'd written and said like, "Hey, could we pay you to do this for us?" Which, I had never considered up to that point. Then it started, it just kept coming. That ended up kicking off my career in WordPress, which was driven more from demand than anything else.

I started to have several people a week reach out, eventually got to a point where it was like several a day and say, "Hey, can you help us integrate WordPress into our existing site?" The rest is history on the WordPress side of things. I followed that lead all the way that it went. I worked on hundreds of projects as a freelancer, I got to touch a huge range. There's very few industries that I haven't touched in some way, shape or form through WordPress because they were all making that transition to the web and they wanted WordPress at the center of it. I got to learn a lot and then spent time in a big agency working on WordPress in the enterprise. Then, that eventually led to the privilege and the opportunity to work here at Automatic on Woo specifically.

eCommerce leading to WooCommerce

Let me back up though. That's where the WordPress journey started. The eCommerce journey, eCommerce and entrepreneurship have always been an interest of mine from a young age. I started out baking banana breads and selling them door to door with my younger brother and learned a lot about business and commerce and margins and shipping and fulfillment and all these little things just through some of our personal experiences.

It started to get serious about 12 or so years ago when my brother and I joined two other young men and we co-founded a company that was an eCommerce startup, where we were building our own software, that was an eCommerce platform. We had our own drop shipping project that was doing fairly well. Then, we were creating eCommerce software to be used by others.

At the same time, this was happening, we were using WordPress to pay the bills and doing software development work and that eCommerce startup ended up transitioning into something focused on paywalls in the media space. I learned a lot from that experience.

It was around that same time, I think Woo was coming out. I remember that and had experience with a few other plugins, like WPeCommerce before, I think, was the one I used before Woo. My formal experience was within that startup context of building a platform, basically, proprietary that ended up becoming something that does quite well to this day. I'm no longer involved in it, but learned a lot from that experience. Then, just through that line of doing WordPress service projects, eCommerce would consistently come up in multiple shapes and forms.

I would do a project that had a Gravity Forms based eCommerce application in it, or eventually started to do more with Woo, did projects on WPeCommerce, did some Shopify projects early on that integrated with WordPress. Through the service lens of my experience, I got to touch eCommerce in a lot of different ways and shapes and forms beyond the startup experience. I realized when I joined Woo that yeah, eCommerce has been a pretty consistent thread throughout the arc of my professional experience in multiple way shapes and forms.

Bob:I find it maybe amazing having talked to all three co-hosts. I know myself I've caught bits and pieces of the backgrounds and things you've been involved with just through our discussions with other builders on the show. I'm always just amazed. I'm like "My God, I've got three veterans on this show." The vast experience that all three of you have is incredible.

It ties into what I've told the other two co-hosts on the last two podcasts is I feel like I was extremely lucky getting the three of you as co-hosts because you each bring in a different perspective. You're each working in a different space right now. I mean, it's the WooCommerce space, but you're also bringing in such interesting history into that conversation. Sometimes, when I hear the background of all three of you, I think, "Oh, okay. I can see where during many conversations I've been involved with with you, where something comes from that you talk about."

You have a lot of meat in that background that nobody knew about and you're bringing it to the table. It's been an honor for me just to have you three on, because it's, yeah. It's just, sometimes, and I've said this before and I'll say it again. Sometimes I love to just sit back and let one of you run away with the guests. There's just a clicking going on. There's something, maybe magical ..

Jonathan: That's a great word.

Bob: Yeah. It's magical. I just think, "Man, I don't even need to say anything here for a while because the co-host and whoever I have on are having a conversation and I can watch it grow and expand”

The big arc of eCommerce experience

Jonathan: What I found interesting too is this WordPress thread, like WordPress at its heart to me is about empowering creativity on the open web. I've had the privilege of seeing that in so many ways and shapes and forms over the years. As I look back on it, commerce is a pretty natural follow through. It's a natural aspect of if you're creating value on the web, at some point there's often an opportunity for a value exchange where you're providing something that someone can then buy. Yes, I've had the privilege of direct experience with Woo over the years, but the bigger arc of my experience in eCommerce is just that broader commerce experience with WordPress generally.

Because a lot of what I've had the privilege of doing with WordPress over the years has either been for small business or large business or NGOs that have had some commerce component to it, whether it's subscriptions, whether it's donations, whether it's selling products, or oftentimes, through integrations with other systems like Shopify or native things like Woo or WPeCommerce. But that's something that I've realized more recently like, "Oh yeah. This is a pretty consistent thread over the years, apart from my direct startup experience in the space."

That's something I really like about WordPress broadly is when you take this more general focus on empowering creativity that tends to lead, I don't know, there's a pretty close association with commerce in my experience. That's been really cool to see that sort of naturally happen over time. I think it was inevitable that you would see WordPress become this center for commerce. Woo happens to be the thing where most of that takes place these days. If it wasn't Woo, I think it would be something else.

Bob: Right.

In that huge span of history, it's been a shorter segment as far as it being a co-host on the podcast. You came on at the first of the year when the podcast went to weekly, I brought on both you and Mendel. Brad had been in place for a while. I've asked them both this same question.

Is there some element or a piece of all these conversations you've had, or that you've been involved with up until now that really stands out and gives you a better reflection of who Woo builders are. Maybe something you've heard over and over and over again?

WordPress and WooCommerce communities, overlapping but different

Jonathan: First, I've really enjoyed all of the interviews that we've done and the ones I've listened to that I haven't been involved in. I love hearing different perspectives. I love hearing different people's stories and how they think about things. If I zoom all the way out, I think it's been a bit of an education for me. Over the arc of my past year, because I'm now coming up on a year of working in Woo and I know WordPress quite well at this point. I've been a part of the community for a long time. It's been interesting to see the ways that WooCommerce and its community is different than WordPress and its community. There's so much that's similar, but there's some differences. I think it's because of that sort of centeredness around commerce and the value exchange there.

I had noticed myself being somewhat on guard when I first got started to talk about money and to talk about commerce topics with folks in the WooCommerce community. Because in WordPress it's open source, it's free, and sometimes there is a shyness about making money. In general, we struggle with commercialization in WordPress, like how do plug in authors, how do builders make money in this ecosystem? With Woo, I'm still trying to understand this, but there's a difference there. I think in general with merchants, for instance, there's a comfort with paying for things because they're making money. There's not this expectation that everything should be free, not that there is in WordPress, but there is a difference there.

Over this past year of listening to guests and just hearing different stories and looking at things, it's been a great opportunity for me to see this eCommerce industry represented by Woo and WordPress as, they have a lot of overlap, but there are some differences between them.

This year and the guests that we've brought on and listening to and just gaining perspective has helped me get a little bit more definition. Because I started out from this like WordPress centered, appropriately. The base of this kind of open source where everything gravitates towards free, whether it should or not. Whereas in commerce, merchants and builders don't have that same base expectation, at least in my overall experience.

Entering the WordPress ecosystem through WooCommerce

I'm still parsing that, but at the heart of it, there is a difference and this is evidenced well by people who come into Woo who don't know WordPress, which I think is awesome. It's one of the things that I get to see more of, people who are coming into the WooCommerce ecosystem. They come to love WordPress, but they're coming from a commerce first perspective. They care about different things like the work with merchants in this industry tends to be more focused on marketing and how to run an eCommerce business of which the technical is only a smaller piece. I like to approach life with a pretty open go with the flow and see where it leads perspective. That's something I wasn't expecting. I saw this more as a subsystem of WordPress where it really is like an adjacent system that just has a lot of overlap, but it's unique.

Bob: That's interesting, because I haven't really thought it through in my head. That's something that has been apparent in my podcasts over the last 4 plus year. Yeah. How many people that are actually creating these WooCommerce sites for clients and the people that are building products for WooCommerce, how valuable that would be for them to recognize that.

Not that they don't recognize it, because some of them essentially are creating products that are built to do exactly what those people want to do and that's sell. Some of them are probably coming from long WordPress paths as well, and to be able to not separate them out, but to understand, yeah, I'm dealing with a whole different audience here. There are some, sure there's some like-minded things between WordPress and WooCommerce obviously, but there's a lot of unique pieces as well.

Publishing and commerce

Jonathan: I think what I found helpful is to take the two missions, if you look at the missions for a moment. WordPress is about democratizing publishing, making creating on the web accessible for anyone. Woo is democratizing commerce, making commerce accessible. It's all about the money, WooCommerce, right? I mean, it doesn't have to be literal money exchange, but it is this commerce exchange of value. There's a clear similarity between the two because publishing can often have a commerce component to it.

Anyway, yeah, it's very complimentary, but they are distinct missions and distinct ways of thinking about things. That's been great for me. I knew that intellectually going in to this because I started out with, all right, this is the mission and this is what we're going to do and everything I'm doing in community is in service of this mission. Over this year of getting to know guests and talking to more builders and doing research and interviews, et cetera, I've been able to move from intellectual to really taking it to heart, like, okay, wow, there are a lot of adjacency, a lot of compliments here, but some clear differences between the two ecosystems.

Bob: It puts a bit of added pressure because when you think okay, I'm a WordPress developer, I'm creating static sites, professional service brochures sites, I'm creating a blog for somebody, maybe it's even a news site. Something that is really content based.

Now, when it comes to the builders on the other side of things, the eCommerce side, they're building people's livelihoods. The other sites can also be a persons livelihood because it branches out a bit more. If you're an attorney, yeah, your livelihood is in the court and everywhere else and doing all this stuff and you can talk about it, but with commerce your livelihood is online, selling, people buying, making conversions. There's that added pressure, a bit, to the agencies, to the product builders, to make sure this works seamlessly and people have expectations and I've got to deliver those expectations on my end.

Jonathan: Take a simple example like a forms plugin, right? There's a lot of great ones out there. Gravity Forms, Ninja Forms, et cetera. I personally know multiple operations running like multi-million dollar setups on Gravity Forms as a basis. Right? I doubt that that's what they saw when they first said, "Let's build a forms plugin." This is the same with Woo. There are some major operations running out of Woo that was probably quite far from mind. This is what can happen in open source. As a builder, you can build a simple plugin and then you get an email one day about how it's being used in this massive setup. They ask a basic question. You're like, "Oh, well I never intended it to be used at that scale." Yeah, it's very interesting.

Bob: It is.

Hey everyone, as we get closer to the launch of the next iteration of Do the Woo, I would like take take a moment to thank our sponsor As a builder, did you know that are are dozens of WooCommerce meetups globally? These are the perfect opportunities to drop in occasionally and listen to store merchants and beginners share their stories and challenges. It also is a great resource for the clients that you have that are new to WooCommerce. All meetups can be found at And now back to the show.

Now, you had said that overall, you just love hearing all the guests and the guests you've interviewed. I feel the same way. The other two co-hosts felt the same way. I did ask them to pull out maybe one or two particular episodes, and it could just be one as well that just something stuck out, you know? It wasn't that it was better than all the others, but there was something that hit you a little bit more in the old thought process or later on you contemplated on it a bit more.

The guests and episodes that stood out and why

Jonathan: First, they're all my favorite. There are a few that stand out.

I really enjoyed the interview with Matt Mullenweg, and being able to just hear some of his perspective on things. It was also on my birthday, which was kind of awesome. Yeah. That was great. I enjoyed that for a number of reasons.

I really enjoyed the interview we did with Nate Stewart from Big Commerce, just hearing a different perspective, such a great example. I think they've done some great work to think about making commerce more accessible over the years. They've transitioned to more of this like open SaaS thing and they've really embraced WordPress. Hearing his perspective, I really enjoyed. I think sometimes people are a little too myopic or they're like, they just think about one platform. It's like, well, what can we actually learn from what other people are doing and how they work together?

Then I really enjoyed what we do with Matt Gerri He's a great example of a builder in my mind that has a lot of value to contribute that can easily go under the radar. Yeah, like I've known Matt for a long time and seen what he's done over the years. It's pretty remarkable to me. You can have these like small, easy to miss, little operations doing some really great things. Whether it's plugin work, whether it's service work, product work. I love discovering those when we get to bring people onto the show or hear about a builder that's doing some really interesting thing off in their little corner of the world that's providing a lot of value that you just wouldn't otherwise know about. Those are the ones that jump to mind.

Bob: Yeah. Cool. Well, I cheated because now when I get asked that question or if I ever get asked, I can just say my favorite ones were with my co-hosts, because they talked about some of my favorite ones. I've got this all strategically planned to make my life easier.

Okay, to round this out, and this has been a fun one because I think nobody can predict what the answers will be or what they'll come up with. I want you to tell something both personal, not too personal, but something personal and something professional that maybe the majority of people out there that are listening don't know about you.

Jonathan: Man. There's a lot of things, Bob.

Bob: I know there is.

Jonathan: There's a lot of things.

Bob: Well, you can meld a couple together.

Both personally and professionally experimenting with habits, habit design and execution

Jonathan: I think, if anyone knows me for a bit, they'll have some context, but a lot of people don't know to the extent to which I experiment with habits and habit design and execution. Today is day a thousand something in a row of doing pushups every day and taking a cold shower every day. I'm now tracking 39 different habits and I'm always experimenting with different things. I have a lot of different projects that I work on on the side and I've incorporated it, so it's like a mix of personal and professional, right? I, as an individual, am really good at jumping in and starting things, like putting a bunch of energy into something. And so you'll see me do this and I'll start this over here and I'll start this. Habits are the key to keeping the momentum going over a long period of time.

As an individual, I have my strengths, I'm good at jumping in and improvising and just sort of getting something up and running. When I decide that something's important, then I'll design a habit around it to keep it going. I'm working on learning Spanish. I spend five minutes a day every day doing a little bit of Spanish. I'm a musician. I like writing music. I do illustration work as well. I'll do a little bit of that every day. Yeah. There's a wide range of things. I feel like at this stage, in my career and my life, it's a good feeling to feel like I'm just getting started.

There are definitely the days where it's like, "Wow, okay, that's a lot, there's a lot going on there." But I'm careful to keep the scope small. Most of the things I'm doing are things that I can keep going with just five minutes a day. Then I'll have those moments where I'll have a burst and put a bunch of time into something and take it further along. Yeah, that's something I think a lot of people don't know to the extent to which I'm constantly experimenting and trying different things. What's great is that I do find things that stick and then I keep it up and then see that momentum over time.

Bob: Yeah. From that, I can tell that from our conversations that even though I may not have known that about you, it makes sense. It's like, ding, ding, ding, ding. Okay. I get it now.

Jonathan: I love things, like I keep a harmonica in my pocket almost all the time. I like to be writing music or working on music. I take long walks oftentimes when the weather's nice or even when it's not. I sometimes wonder what the neighbors think of this guy that walks around all the time and then I'll whip out the harmonica and play while I'm thinking about something. Always trying new things. I also like cooking and I enjoyed the cliche of making bread at home during lockdown.

Bob: Yeah. Oh yeah. A lot of people took that up. We were trying to keep up on bread supplies. I mean, just because we having been making homemade bread long before the lockup, "Okay, well suddenly everybody's buying it. Oh no, we're out of flour. We can't get flour."

Jonathan: Can't buy yeast anywhere.

Bob: Yeah. Yeast was an interesting one. We bought this jar so we have it. I don't know how long it will last. We'll see how that goes.

Jonathan: That's awesome.

Bob: Well, this has been cool. Lets first have you share where people can connect with you.

Connect with Jonathan

Jonathan: You can go to That's my little WordPress on the web that I've been keeping up and running for over a decade now. Always to some degree of construction, but a lot of my writing is there. I'm respectably active on Twitter, @SirJonathan. If you're interested in some of my photography work, I've got an Instagram profile that I quite enjoy. I think that's the extent of it. is my home on the web and where I keep everything else connected.

Bob: Very cool. Well, I thought before we close out here, if listeners are not new and they've been listening for a while, they know that we're kicking out the next iteration of Do The Woo next week.

Jonathan: Yeah.

Bob: Official launch is October 6th. First of all, I just want to say that and let everybody know that Jonathan was very instrumental in this iteration as far as feedback and thoughts. This has been quite a new adventure for me and I'm hoping a lot of people are going to find this very useful.

Just to throw out a couple of things, we will be adding a second podcast, actually, an extension of this podcast. It's going to be in the same feed, but twice a month on Tuesdays. We will be doing something called Woo Perspectives, which will be sort of a panel, but not formally. I'll be bringing in three individuals and we'll just be talking about some Woo things I bring up.

I'm just going to let them run with it. It really is about conversation and letting people share their own perspectives and insights rather than just hearing always how something is built. We can hear what they think about something going on in the space or something with eCommerce. I think it's going to be fun because I'm simply going to be a moderator and the co-hosts, I'm sure, may just pop in every once in a while as well. We'll be starting out the first one, hopefully with all three of the co-hosts. We'll see how that goes by the time that happens later in October.

Yeah, it's going to be fun and it's going to be kind of open to a lot of individuals that just have a lot of experience in the space, whether you know them or you don't know them, they're going to be instrumental in the WooCommerce growth. I think just hearing what they have to say is pretty cool. It's going to be fun. I am looking forward to that piece of it. There's a ton of other things. Anything that we've talked about that stands out that you want to share with anyone?

Jonathan: I think the big thing for me that I think is worth calling out is that in my work in community at WooCommerce, we're really focused on the merchants and helping merchants get connected. I love the work that you're doing and Do The Woo has been, as a podcast and as a community, focused on that builder space. I think it's really important and there's a lot of opportunity to, like you're already saying, to share insight and perspective to help folks connect.

You've been doing that in a lot of ways over the years. I'm excited to just see more of that happening. eCommerce is growing quickly. The WooCommerce ecosystem is growing and more and more people are wanting to get in to build things, to provide service and value to merchants and getting into it. You've been building a great resource for them to be able to do that.

I'm just excited about it in general. It was great to see you switched to a weekly and just you've had consistent great content over this, it's almost been a year now. I'm excited for the next iteration. I love the little a change log you got going on. This is 5.0?

Bob: Yeah. I'm going to have to update it real soon here.

Jonathan: Yeah. I'm just generally excited about it. This is a great community. For me, as I'm working on helping serve and connect more of the merchants, I have a lot of confidence in knowing that the builder community is, is alive and well and growing and the work that you're doing and Brad and Mendel, it's fantastic. I'm excited to see what happens next.

Bob: Cool. Excellent. Thank you.

Just to let everybody know, I've been pushing out on since Monday, this last Monday, or actually before that in the week before, a post every day that talks a little bit about different pieces of the new site and what you can expect to find. Check that out. It concludes on next Monday with a post called Community and Connections Without the Noise.

I'll just give a little teaser to that. This resulted in a lot of the people I talked to about what I was doing with this site, one of the first things they would ask me is, "Oh, are you starting a forum? Are you doing a Facebook group? Are you doing a big Slack channel with all these channels in there for people to come and talk?" I'd say "No." And they'd say, "Okay, community connection. Tell me more."

This was something that I've thought through how you can take a perspective of that and grow a community and connections more on a personal level rather than just a bunch of noise. That's not that that noise is not good. There's a lot of places for it. People need that and get in and talk with each other and be in those crowds sharing ideas and stuff. I'm just taking a different approach to it. Look for that next Monday. In fact, I've already been asked by one or two people that maybe that might make for a nice discussion in a webinar or something, just because it is taking a little bit of a different perspective on the whole idea of building community. I'm looking forward to that.

Well, Jonathan, thank you so much. This has been fun having you as a guest instead of, well, I shouldn't say instead of. It's not been any more or any less fun than having you as a co-host, but it's just great to hear more of your story. I want to thank again, don't forget about that community chat I told you every last Thursday of the month on the Woo Slack core channel at 1800 UTC. Good stuff, get in there and you can learn some stuff and you can ask some questions. Jonathan, again, thank you.

Jonathan: Thank you, Bob.

Bob: Everybody have a good weekend. We will be back with the new Do The Woo next week. Take care.