Reflections of a 3-Year WooCommerce Managed Hosting Journey

BobWP:
And we’re back. Do the woo number 32. I’m Bob WP, and yes, Brad survived Thanksgiving and hello. He’s like the most popular co-host in the world and he’s my favorite one. Of course right now. He’s my only one, but I hope so. He is my favorite one. So how’s it going, Brad?

Brad:
It’s going good. I did survive the holidays. How about you? Good enough. Turkey?

BobWP:
No Turkey. I don’t eat meat, so it is easy to survive it for me so I don’t overeat quite as much.

Brad:
Yeah, it’s always a fun time, right? Family. Lots of food. And we desserts, treats get to, I mean, officially kick off the holiday season. I kick it off with Halloween, but I know Thanksgiving’s also a big fun holiday, so it’s always good to see the family.

BobWP:
Yeah, yeah, definitely. So did you put your tree up?

Brad:
I bought a tree and it’s up, but there’s nothing on it, so it’s just like a pine tree in my living room, which is really depressing looking, so I definitely need to get some stuff on it.

BobWP:
Okay, well get on that right after the show. I think that’s their next step. Will do. Well we have a special guest actually, I saw our guest talking on Twitter about a recent anniversary he had where he’s currently working. Mr. Chris Lima. How are you doing, Chris?

Chris:
Good to see you guys. I’m good.

BobWP:
Chris has been not on the show yet and that’s amazing. So I felt that with that three year anniversary at LiquidWeb, that this was a great time to, oh, we can take a trip back through the last 36 months, month by month or something. I dunno. We’ll see how detailed we get here. But for those that don’t know what you do, Chris, I’m sure there’s maybe a handful out there or something listening. Can you give us a little bit of your background and then we’ll chat into your three years?

Chris:
Sure. So I started working on e-commerce stores in 19 97, 98, after several years of working on the internet already. I think we launched our first e-commerce store in 97, and it was a ridiculous amount of money and a ton of people. And we spent nine months because authorized.net, which was the payment gateway at the time, it had an API that you could call, but it had no ui, literally nothing. So in order to build an e-commerce store, especially if you were going to actually authorize a payment and then wait until you ship something to actually take the funds, you had to build all that ui, right? If you wanted to reverse the charge, you had to build the ui. So building this kind of store today, you could build it in about five minutes, but back then it was three people, hundreds of thousands of dollars and six to nine months of work.
And from then to now, I’ve spent a whole bunch of time building predominantly SaaS companies, mostly focused in the enterprise space about, I don’t know, in 2005, I started working with WordPress and by 2010 got involved in the WordPress community, started working eight years ago with WooCommerce and working with products and companies in the WordPress space and in the WooCommerce space. My goal or my interest after leaving an agency was to think about how do we make WooCommerce more accessible, more available to more people. Part of that dynamic is WooCommerce would fall over on the higher ends. Brad and the folks that do serious work with WooCommerce over at Web Dev know you get to this point where things start shaking and rattling and you go, we’re going to have to do something about this. And we had done that when I worked at an agency called Crowd Favorite.
So we had done that work with a very large store and a couple more. And in the midst of that discovered, in order for WooCommerce to be more acceptable by people who are starting, they have to know that there are larger stores that actually are working too, or else you’re just going to say, forget it, I’ll go somewhere else. So how do you play that game on both ends, right? How do you build out the larger stores and the infrastructure for larger stores and at the same time make it super easy for smaller stores? And that’s when LiquidWeb came over and they started asking for some advice, and I was in between things, spent a lot of time in hot tubs and smoking cigars, and they said, would you join us to help us build a managed WordPress product? And I was like, no, that’s boring, right?
There’s 10 other companies that are doing that. I said, it’s interesting because there are a couple problems that people haven’t really solved yet, but unless you want to build a managed WooCommerce offering, I’m not interested. And they said, what is a managed WooCommerce offering? I said, oh, here, given this writeup that I’d written up already. And I said, this is what I’ve been thinking about doing on my own, but I’d be willing to do it with you. I don’t care how we do it, I just think this is some of what needs to happen. And it was taking all that SaaS background and bringing it to WooCommerce. So when you think about a SaaS, yes, there are tiers, you can buy different tiers of product, but fundamentally what happens is you pay to get access to the product. Sometimes you even get a free trial to experience the product, you pay to get the product, and then you have it.
If you think about any SaaS that’s delivering value, you don’t sign up for Basecamp. And then after you sign up for Basecamp, they’re like, oh wait, you want to do math? You got to buy a math add-on. Wait, you want to send out an RFP? Or you want to track a time, you need to add a time, add-on whatever it is. You just buy Basecamp. And then it comes with everything you need to do the work that you want to do. And a lot of SaaS products are like that, and sometimes they have features in another plan and you have to move up the plan. That’s a packaging game and strategy. But we didn’t have anything like that in the WooCommerce space. So every single person who started with Woo would experience this dynamic of, first I have to buy a hosting plan, which asks me questions about what resources I need, which I don’t really understand.
So how would I know? And then I get it, and then I get WooCommerce, but then I have to go figure out today, even today years later, the most average dynamic that happens across all the hosts is you buy a managed WordPress plan, which gives you WordPress stuff. You add WooCommerce, maybe storefront and an SL cert, and they go, see, we host WooCommerce. And you go, right, but what about the rest? And that’s why we see SaaS companies like BigCommerce and Shopify doing well because they are stepping into and filling in the gaps of that e-commerce space. So I joined LiquidWeb three years ago now to do that, and we’ve had the product in the market now for two years. We’re getting ready to make some adjustments to it in January, so you’ll get even more coolness. But it’s been a long and crazy and fun three years to be working with them to build out this kind of offering.

Brad:
Yeah, I mean, it’s definitely a cool platform, and I’m definitely one of those people where, just like both of you, I’m sure when people know you work on the internet, you build websites, they’re like, oh, I’m going to ask you every question I have. So a lot of friends and family are like, Hey, I want to a store sell a couple products. Maybe they do something in their spare time. Should I use WordPress? And I’m like, no, no, it’s not as easy as people make it out, especially on the e-commerce side. And I think it validate, it goes right back to your point of all the dots aren’t connected. You can sure, you can go install WordPress, install WooCommerce, and then there’s this massive configuration game and then figuring out all the various add-ons you may or may not need. What version of PayPal do I need when there’s like 10 of them?

Chris:
We had a client just this last weekend, right? It is Black Friday, cyber Monday, all the crazy. And their site goes down, I mean just boom, and then 30 seconds later pops right back up and then goes for now and then comes. And so our team is looking at our support, guys are looking at it. I think it was actually on Thanksgiving. And so I get a text, I happen to know the merchant, and he sends me a text going, Hey, your support guys say I should just move up to the next plant. And of course I’m like, yeah, of course. That’s what everybody does. They just go, just get more resources. I’m like, that doesn’t, hold on. Tell me about your throughput. I’m like, that doesn’t make sense. So I said, give me a second. So excuse the family, go to the computer, pull up the stuff quickly, do a scan on what he has running. We have the ability to look at what’s happening here, and he’s not using the right PayPal, he’s using a different PayPal. He swears to God, this is the official PayPal extension and it’s not. It’s the wrong one. And that particular code base is creating timeouts and problems and whatever. The site was never going down, believe

Brad:
It.

Chris:
It was just this one payment gateway and the payment gateway was getting locked up and then holding everything and then starting again. And so it made it look like it goes down and goes up. Well, the website was still live, and I just said, do me a favor, go here, download this, install this, and configure this here, and then turn it on. And then the rest of the weekend he was fine and making all sorts of money. How is he supposed to know which is the official plugin and which one isn’t? The kind of stuff that we go, we got to get in there and solve a lot of that and make that easy for people so that they don’t have that drop.

Brad:
And I love it because now I have a place to send people. Obviously I’m a big open source proponent. I love WordPress, I love WooCommerce, I love everything about it. So to tell people to go use things like Shopify never felt right, even though for me it was the right recommendation because I didn’t want to be the one supporting how many family members e-commerce sites. But now it’s having something like the manage WooCommerce space and that basically liquid web is created. There is a place we can send people and have the confidence that hey, even at the small level, you can kind of kick the tires on your idea for minimal investment. You have some real pros behind you to help you out and see if it’s a viable business, see if it’s something that can grow and blossom if it’s something you actually enjoy doing versus investing. Well, certainly not 97 amount of hours, but a lot of hours to actually build your own store on your own. So it’s come a long way, and that’s just in, like you said, a couple

Chris:
Years.

Brad:
It’s amazing. So very cool. I’m curious because another question I have, obviously you said you had a plan, this and stuff. You have experience working this for a couple decades now. So going into this, I’m sure you had a lot of expectations about some of the challenges and stuff you’d be up against. I’m wondering to flip that around a little bit, what are some things that maybe were unexpected that you came up against that you hadn’t really thought about or didn’t realize maybe there was a problem that needed to be solved until you started really digging into what you were building, really working with store owners and clients? Anything unexpected that comes to light that you want to talk about?

Chris:
So I’ll get in trouble for talking about all the things that were unexpected because I joined a hosting company and then

Brad:
It was all perfect. I’ll tell you what,

Chris:
I joined a hosting company, and then we got into this one part where I went, Hey, and to be clear, for anyone listening, this is a story that happened within the first two weeks of my employment and has not been a problem since.

Brad:
Disclaimer,

Chris:
Just in case my boss listens to this podcast, but we were two weeks into launching our managed WordPress platform, and one of our good friends, you all know Sean Hesketh had his personal site moved over and he brought it over and it was awesome. And then two, three weeks in his site went down and it was down for several hours. And his text to me was, Hey, do you guys know that the site’s down? What have you? Right? And I went, no. So I logged into our Slack where we have a channel that is called critical events. And so if a site is down or whatever, it’s amazing how many things can go wrong in a hosting company when you’re on the inside that you just don’t know when you’re on the outside, like network cards fail, power strips fail, server racks fail upgrades, os upgrades fail, the vendor, that’s the uplink, right? Your network coming in that fails, and yet you have all these redundancies. So most time you see it pop up and you’re like, oh, is that affecting something? And you’re like, no, no, no, we got it and they handle it. But I go into that channel and there’s nothing there. It’s silent.
And I’m like, what is happening? How come we don’t have people scrambling? We have a site down and how many sites are down? How do we know? And it turned out nobody had flipped the little switch on monitoring for this product. So you’re two, three weeks in, whoops. And you’re like, we’re a hosting company. You monitor all the things, right? And you get surprised where you’re like, well, did you send a note asking them to turn it on? Or we were doing malware scanning, and I’m like, okay, when we catch malware scanning, this was like in the fourth week when we catch malware scan, do we send it to someone for remediation? They go, yeah. I go, okay, where does it go? Oh, it goes to that Slack channel. And you go into the Slack channel and you’re like, this is cool. It’s all right here. It’s highlighting. You’re like, who monitors the Slack channel? Crickets. Crickets. And you’re like, what? Right? So a things we learned, a lot of the things that I wasn’t expecting was just low level being inside a host
And workflow, just making sure that everything crosses over. So that was the early days where you’re like, I didn’t realize that we had to do these things to make these things happen. I just thought it was all automatic. But more to your point, when we started working with stores, I’ll be honest, I thought a million dollar WooCommerce store was an anomaly. I thought a store that made a million dollars in a year was just not a normal thing. We have tens, twenties, double digits into the, I would guess probably into the thirties or forties of stores that do from 5 million to 40 million a year in revenue on, wow,

Brad:
That’s awesome.

Chris:
I can’t even tell you the count on 1 million, right? That’s just not big enough for us to catch it. And you go, what? I thought the million dollar store was this anomaly is this strange thing. And then you’re like, oh, no, no, no. We have tons of stores doing this, which is great news, right? Incredibly surprising and still really great. And then you get into it and realize, okay, it is a function of what’s your price point? How many things are people buying? What’s your average cart value? How often do you have customers come back? Is it recurring? All these things that you get into to realize how do we help these stores? Because it’s very different taking a, I make a hundred dollars a week and trying to get them to a thousand dollars a week. That’s a lot of work. Whereas I make $11,000 a week and then you go, okay, how do I get you to 20,000 a week?
And you go, oh, that’s not as hard. We got a lot of stuff already going. You got a lot of traffic coming in, you got a lot of sales going on. How do we do little order bumps? How do we do post-purchase sales? How do we do little tweaks to help your revenue grow up is easier when you have that flow. If you’re unknown and you’re not getting traffic in, man, it’s harder work. I thought we were going to have to spend time on the early front, and we ended up having to spend time helping grow good stores that were doing well. I thought we were going to spend a lot of time with store owners. It turns out we spent a lot of time with store builders. So both of those pivots were things that I had predicted the opposite way. The benefit is, of course, I hold any idea. I have pretty loosely in my hand. Maybe this will work. Let’s try this. So you do a lot of experimentation, and so we were able to pivot pretty quickly to get ourselves to a different place, to be able to serve the people that we’re coming around and saying, I want to do this.

BobWP:
Yeah, I was just going to say is that I was going to ask you, in those three years, has there been some pivotal moment that really you had the epiphany that was like, whoa, we had, maybe it’s more of you’re at a point where you’re thinking, okay, we’re really starting to nail this. We’re really starting to figure this out. Was there any moment besides that realizing that this is the size of stores that’s on here, we need to start taking care of these people.

Chris:
There are definitely some things that still surprise me, and I know Brad, in the work you guys do that you probably have already experienced this, right? It’s amazing to me the basics, the basic blocking and tackling when we talk about email lifecycle emails that customers haven’t done or that they’re not always inclined to do. And so literally, I met with these clients and I would go, okay, so tell me what you’re doing on the email front. You’re doing good amount of volume sales, whatever. Oh, we do abandoned cart. I’m like, right. Abandoned cart is a good email to send out. People put stuff in their cart and then they don’t follow up following up with them. Right? That’s good. What else are you doing? What do you mean? What else are you doing with email? Nothing. So when you have a sale, oh yeah. We sometimes send out an email when you have a price change, when you have a first time purchase or you’re following up with a request for a review basics, and they’re like, no, we don’t do any of that. I think my default, and it may have been just because of the customers I was working with and the kind of projects I was working on, that was always one of the first things we did was, let’s get your email game on point. Most customers are terrified of that blank screen. Is that Lisa behind you?

Brad:
That is a special gust. Lisa Wilson. Oh, hey. Hey. You got to talking to the mic though.

BobWP:
I can’t hear them. They’re in your headphones.

Brad:
You can hear ’em.

BobWP:
Oh, they’re there. Hey guys.

Chris:
Lisa, don’t mean to interrupt or anything. We’re supposed to be going up cheese stakes.

BobWP:
Oh, okay. I see what’s going. Speaking of buying commerce,

Chris:
That’s critical. That’s important. You can’t delay that. What we discovered was clients would look at that blank screen of, I don’t know what to put in this email and freeze up and then not do it. Right? And so a lot of times we come alongside to say, Hey, here’s some tips. Here’s some strategies, here’s some articles. Here’s some companies that can help you. Here’s some tools, but really you’re leaving money on the table when you’re not automating some of these processes. And that was surprising, right? I just thought, oh, no, no. When we first put Jilt out as a partner, and we rolled it out, we thought everybody in the brother’s going to turn on every feature. Why wouldn’t you? And then they didn’t. And you’re like, what is happening here? And so you’d start getting into the education to help and start figuring out and realizing, I’m just scared of writing the wrong thing, and you’re like, writing something is better than nothing. Let’s help you get over that hurdle.

Brad:
I think a big keyword to that is automation. I think a lot of people assume it’s a very manual process, and they need to manually send out every single email that goes out to their customers or lurkers when there’s a lot of amazing systems that can automate the majority of those emails that are going out. So it’s kind of a set it and sure analyze it and make tweaks and stuff, but by and large set it and it does its thing.

Chris:
Yeah, that’s exactly

BobWP:
Right. What I want to know is all the time you’ve been involved with the web, was there any time prior to this that you thought, boy, one of these days I want to go work for a host?

Chris:
No. So years ago I worked at a company called Crowd Favorite, and Alex King was the, so Kareem Maki owned Velo Media. They bought Crowd favorite, crowd Favorite had been run by a guy named Alex King. And Alex and Kareem came to me. We sat down, it was at a press NOx, it was probably one in the morning, and we’re sitting in a hotel lobby and they said, we want you to run a hosting company, but we want you to, let’s go partner with someone to give us the infrastructure, and we want you to run this thing, but just do it for Enterprise. Just focus on the really high end. This is before Page Lee was doing something like that and really with a focus towards account management. And I didn’t know whether to laugh or cry.
I’m not a hosting guy. There’s so much I don’t know. And Alex goes, there’s always things we don’t know. Are you telling me? And he starts listing off the CEOs of many hosting companies. We all know, are you saying they all know the same things that you’re saying? You don’t know. Like, wow, Kubernetes coming out. We don’t know this, and what about this? And you’re scaling this? And he’s like, you think they all know that? Yeah, you’re right. They probably don’t, but that’s my bar. If I’m going to step in, I need to know something.
So I just backed away. I was like, Nope, just call me a scaredy wimp, but I can’t pull that off. So then years later, I joined a hosting company and I’m in the middle of having conversations about Kubernetes. The first time I heard Kubernetes, I couldn’t even spell it. You know how you try and Google something and you can’t spell it close enough so that Google even knows what the heck you’re talking about? That was me and Kubernetes four or five, four years ago. And I was like, I don’t know. I don’t know what this is, but oh, containers do I know what containers are? And then you start getting into automation and resizing and all this stuff, and you’re like, whoa, there’s a world of this that I, and I don’t have to know this. I’m trying to do product above this. And yet, so much of product definition is tied to infrastructure. And are you using containers? Are you using VPS? Are you using OpenStack? And what features come with it and what don’t? I never imagined I’d be working at Host, but this is where we could build that product that I wanted to build the fastest and easiest way. So we said, okay, let’s do it.

BobWP:
So you mentioned a bit ago, or probably at the beginning in 2020, a lot of cool stuff coming, and I don’t expect you to divulge your secrets and stuff, but are you kind of feeling at the same time, okay, you’re three years into this, and

Brad:
I said, tell us your secrets, Chris.

BobWP:
Yeah, yeah. Really, really tell all spill it out. But are you just at the tip of the iceberg here? I know you said there’s a lot of exciting stuff and you’re really looking forward to the future on this.

Chris:
So I don’t know a lot of hosts that do free trials, it’s just not a thing we do. And I spent a long time talking with exec team and our board because there’s a financial dynamic to that, right? Whenever you’re like, I’m going to allocate resources of infrastructure that have cost and I’m going to run it for a period of time without charging anyone anything. Also, it turns out that technically to do something like that, when all your systems are billing systems that say, first I create an account, then I collect money, then I provision hardware, and you’re like, well, I want to do it the other way. I want to provision hardware without an account and then create an account and then collect money. And they’re like, yeah, that’s not how it works. I’m like, that’s how I need it to work. We’re playing, we’re getting ready to roll out stuff like that.
We’re getting ready to roll out some new Gutenberg related, not just some template builders, some easy ways to deploy some new UI for people so that you don’t start with a blank page that’s WooCommerce friendly and Gutenberg friendly and allows you to pick from some of these things. So in your onboarding, you don’t end up free trialing and having a blank, nothing, which is really interesting. Onboarding itself is really interesting stuff. And then for the longest time, our WooCommerce plans have been one site only, and we’re going to open up the doors a little bit to let you run multiple stores in a single plan. All of which I think is, we’re doing a couple other things, which I can’t talk about, but those things I can hint at because we’ll see them early in the first quarter. It’s just like you’re at the beginning of what looks like a WooCommerce SaaS, right? And it’s been a long, I mean, it’s an incredible amount of work and a lot of people involved to really make some of these things happen and I can’t wait for it.

BobWP:
Cool. Well, Brad, I am wondering, I had a couple other things here, an article, but I am wondering if you’re hungry for those cheese steaks. I’m thinking about that. I see somebody nodding back there. I think maybe we’ll pass on the extra things just because I don’t want there to be violence happening in your office there and cheese stake demands. But I am glad we got Chris on to at least get a little bit of the history of the three years and what’s going on. I did want to add that. Woo, 3.9 is in beta right now. It’s coming out in early January. And if you go, I’ll have a link in the show notes, but if you go there and you do sign up for the beta testing, they have a small kind of survey registration form, you’ll be rewarded with a $200 woocommerce.com coupon. So that is definitely worth making sure your site doesn’t blow up, making sure other people’s sites don’t blow up. And then also getting a little reward. So that’s good to know. And it actually doesn’t say that on there, but I found it out another way and I asked if I could share that on the show. And they said, please do.

Brad:
That’s one way to get beta testers good incentive.

BobWP:
Yep, exactly. And then next two weeks from today, we will be having our special show with what’s happening in 2020. A lot of stuff going on with this podcast and looking forward to that. But so Chris, where can people connect with you before we head out here?

Chris:
You can find me@chrislema.com. You can find me at Chris lema on Twitter. You can find me on the Liquor Web website. And we just bought a company called Nexus where we’re moving a lot of stuff over there. So you can find me probably over there shortly. Nexus is NX css.net, so it’s spelled a little different than when we’re talking about e-commerce and merchant and taxing Nexus. But you can also find me on Facebook, on YouTube, on LinkedIn. YouTube and LinkedIn I think are Mr. Chrisma. So I’m around all sorts of places. It’s hard not to find me online. If you search for my name, I create enough content that someone will find me somewhere.

BobWP:
Yeah, cool. And I don’t think I need to ask what everybody has planned because it’s holidays. I know what everybody has planned, and nobody wants to really think beyond the end of December right now and just enjoy the next month. So we’ll leave it at that. How’s that sound, Brad?

Brad:
Perfect.

BobWP:
Perfect. Alright, go get that cheese steak and thanks everyone for joining us. See you. Well, that’s a wrap for today. Thanks for listening and make sure and join us again for some Do the Woo.