Brian Casel: [00:00:00] Hey, it's Open Threads. It's my podcast. I'm Brian Casel. Welcome to it. So, uh, today on the show, I've got my buddy, Chris Lema joining and, uh, you know, Chris has been, uh, through kind of a, a whirlwind of different roles over decades in the web and software industry and WordPress space. And now here in 2022, he has transitioned out of WordPress.

So this was kind of a wide ranging conversation where we just talked about the state of WordPress today and what led him to transition out of it. We look at the landscape of different CMS tools out there, but also, you know, Chris's approach to kind of crafting a career. I really liked the part where he talked about building his own optionality coming from a background in blogging and then coaching and kind of, uh, you know, just creating opportunities for himself.

So really good conversation, always a lot of [00:01:00] wisdom to be shared. So, yeah, this has a lot to offer here. for now. Let's go talk to Chris. Enjoy.

Chris Lema. What's up, buddy? I'm good. How are you doing? Doing good. Yeah. Good to connect with you again. You know, I feel like every time we connect, it's usually like asynchronous or like a Twitter DM, but it's good to actually hop on a call. That's right. Yeah. You know, It's been a while since we really caught up and from what I see from afar, what I caught on in your various news feeds is that you changed positions.

I mean, I've always known you as like, really connected to the WordPress world and, you know, working in the, in the WordPress world and a bunch of different roles. And you're still well connected in that whole world, but yeah. Why don't you tell us like, where are you at now? When did it change and what's 2022 look like for Chris?

Chris Lema: Yeah. So I, [00:02:00] I stepped out into a role. If you go back long enough, right. If you go back, I would guess something like eight or nine years ago, I had a full time job outside of the WordPress ecosystem while I was writing a daily blog about WordPress in the WordPress ecosystem. Right. So. I had this outside job and then my weekends, my evenings, I would write blog posts about WordPress.

I would help WordPress companies and I would fly out to WordCamps and speak as part of the community. But I had a full time job. And when I took the first full time WordPress job,

Brian Casel: that was like the first time, you know, I am probably many people started learning, you know, following your stuff was your early days of the blog.

I didn't know that you were like not working in WordPress at that right.

Chris Lema: When I took my first full time job in WordPress as the CTO and chief strategist at a digital agency called crowd favorite that focused on enterprise WordPress, the people in the company. [00:03:00] We're like CTO, like, isn't that the guy that writes blog posts and goes on stage and tell stories?

Like, shouldn't he be our marketing officer? Why is he our technology officer? And what does he know? And you know, the CEO is like, he's been doing his day job for decades. Right. And they're, and they're like, no, I didn't know anything about that. I just knew he told stories on stage about WordPress. I stepped into that role and made WordPress.

My full time job, which killed the blog, right? Because when you spend all day time at WordPress, the last thing you want to do at night is say, and I'd be like, how about I write another WordPress blog? Right? So the blog really kind of took this little pause for a few years while I was working with crowd favorite.

Then I took a year off and then when I joined liquid web, it was to build WordPress and WooCommerce offerings. And I did that five and a half years, the last year, mostly buying, uh, WordPress products and tucking them in. And all of that was fine. But at the core of who I am, all of [00:04:00] that felt a little less fulfilling than I wanted it to be.

Right. And I'm one of those people as a coach, I will tell people that the single most important thing that you need to learn how to do is make money. You have to figure out, you know, if you have nothing. If you know how to make money, craft an ebook, build an online course, create a membership site, sell a report, provide some coaching, do some consulting.

Like if you know how to make money, then you're never locked. Into the situation that you're in. And contrary to Apple's belief that bravery is taking a headphone port away. My belief of bravery, right? My, my definition is the ability to leave something that is safe and step into something that is unknown.

Brian Casel: I think it's so interesting, like your transitions that I want to talk about your recent one in 2022, but even just going back to those early days, [00:05:00] you were CTO at some other shop, like non WordPress, some other software. And you actively started blogging and becoming well known in the WordPress space.

And it was almost like building the bridge for you to go cross over into the WordPress space. What was that, like 2008, 2009, around then?

Chris Lema: Yeah, it's a desire to continually create opportunities, right? So years and years ago, a long, long time ago, I wrote a patent. The patent I wrote on was with one of the top five decision scientists on the planet, Dr.

Ralph Keeney, and Ralph was the chair of decision science at Duke, which is the decision science school. He had been the professor of decision science at USC, another well known school. This guy is the god of decisions. And he's written several books on decision value based frameworks and all the stuff.

And his point, right, which I internalized and learned was most people are really, really bad at decision making. [00:06:00] And the reason they're bad at decision making is because they let other people put them in decision moments, right? They let other people craft. Do you want, and we've all been in this situation.

Someone comes up to us and goes, do you want a, or do you want B? Choose, and he's like, that's a horrible way to make decisions. Right. And even when we create our own decision problem, we normally are like, Oh, we're going to on vacation. Do you want to go back up to the mountains? Or do you want to go to the beach place?

And you're like, well, how come a African safari wasn't one of the options, right? Like, so he would push you, right. To learn how to craft your own decision moment. And create a lot of alternatives. So as I was looking at the world of type pad and blogger and WordPress, I mean, we're talking about a long time ago.

I was a VP of engineering for a software company. I had been the CTO of another software for that, that we had [00:07:00] sold. And another one before that, that we had sold and I having, I was on my fourth startup and I realized I had some ability to coach others and I started coaching these companies. But this was so early on these companies didn't have websites.

So one of the functions when you're talking about what's your go to market message, what's your branding, what's your value proposition, how do you pitch, what's the narrative that you sell your product? They didn't have a place to put those words. So even as I was helping them craft the words, I'd be like, okay, we need to put up a little five page website and just someone's going to, you say, oh, I'm so and so from I'm Brian from ZipMessage.

What's the next thing they're going to do? They're going to look up ZipMessage. So we need a five pager. And so I started playing with a bunch of these tools and found WordPress is the easiest one to build a five page website. And for me to craft the content or the messaging and put it in there, but then let them edit it and use it, which meant you need to see a message that doesn't require you to be a technologist.

Right. And that's how I found [00:08:00] WordPress and started leaning into that space.

Brian Casel: WordPress has always been kind of interesting because it's like the popularity of WordPress, just. Skyrocketed so fast. And I think that the business side of WordPress was always a few steps behind the rest of the SaaS and software industry has been evolving, but like WordPress was always a few steps behind in terms of like business, you know, approach to building startups, like very tied into the open source community.

I mean, it's, it's gotten a lot more sophisticated now, but like. The sheer volume of users flooding into WordPress sort of helped it survive.

Chris Lema: When I stepped in to speak the first time I went to speak at a WordCamp, which maybe 2012, somewhere around there, 2011 or 2012, I went to apply and I looked at every talk of every WordCamp the year before.

Right. And there was one talk and we're talking like, you know, 10, 12 cities. [00:09:00] Each city had two tracks. Each of the two tracks had 10 talks in it. So 20 times 12, I mean, you're talking about hundreds of talks and there was only one business talk, right? One business topic, how to sell your freelance services or whatever.

Right. And I went, okay, well. There's no marketing, there's no messaging, there's no framing, there's no pricing. There's no, I'm like, I can talk about all these topics for days. Right. And so I took this corner. It wasn't a congested corner. There was no one else talking about it. I go, well, this is very easy, but I created then, as you mentioned, right.

I created that bridge that said, There are going to be opportunities here. I'll build that. And in the same way, over the course of years, right? The recruiting to crowd favorite was because the CEO said, I want you to come help me, I just, as an advisor, I'd helped him buy a couple of companies. Now he's like, I want you to help me integrate those companies.

I knew how to do that. When I left that and took some time off, the folks at liquid web were like, Hey, you [00:10:00] understand SaaS, you understand products, you understand WordPress. We want to build a WordPress. Solution for our hosting company. And so by creating the right opportunities and having connected, I didn't know who liquid web was.

They talked to two or three other people who all said, here's the guy you want to go talk to. You know, part of the decision game is creating enough avenues and opening up enough lanes so that when you decide this is a bravery moment and I'm going to step away and I'm, I'm kind of done doing what I've been doing.

That you let some people know and options appear

Brian Casel: And it's almost like, um, you know, the, how like companies these days are building like media brands and building audience. Like, that's really defensible way to have customers coming to you. It's hard to replicate that. You've sort of done that on, on a personal brand level, right?

Where like companies like liquid web are bringing you into. You know, because you're, you're so well connected and you knew all the background running [00:11:00] product. So, I mean, back to the original thing, like here we are in the middle of 2022. You're not working at WordPress today. What are you doing?

Chris Lema: Three months ago, it was a crazy two weeks, I guess it was about four months ago.

Cause I've now been working for three months in the new company, but about four months ago, I got to a point where I decided I'm kind of done. I'm burnt out and we're all burnt out, right? COVID and staying at home a lot and all these things had created burnout. But I was feeling. More burnt out than that.

And you can tell when you start getting impatient and the other person's barely said anything, you're like, I'm so mad already. And you're like, wow, we're three minutes into this conversation. And so you realize it's about me. It's not about anybody else. It's about me. I'm burnout. I'm tired. And it just so happened that a company reached out and said, would you consider joining in that particular case?

It was as their chief marketing officer, right? So using all the brand and narrative and storytelling and all that stuff, would you take that part of you and join us? And it was outside the WordPress space, right? It was a, a company [00:12:00] that is also another CMS. Called Duda and they were looking for stuff and I had helped a private equity firm in Israel do the due diligence on Duda six months before that, and written up the paper that said, here's my take on Duda.

The founders had read it and went, this guy knows Duda better than most of our employees, like, uh, and he knows the whole space, right? All the competitive nature of everything. And he's telling a story or crafting a story about stuff that's interesting. So they approached and said, would you consider. This position.

And it was the first moment, right? First of all, I was like, yes, I'll consider it because I'm burnt out. I'm tired. It's time to think about other things. But the second notion of it was this would mean moving out of the WordPress space. And, uh, I had to give that a thought because on the one hand companies that had hired me before that, part of what they were paying for was the connection to the network, right?

When you're asked by someone like liquid web [00:13:00] to buy companies, it's because they tried already to reach out to these founders of these startup companies and they get no response. And then I would DM them on Twitter and be like, Hey, you got a few minutes for a talk and they're like, sure. Yeah. Let's get on a call.

And some of my partners at the whoever, like. They didn't reply to us. I'm like, well, okay, but I know them so we can chat. Right. So when you leave that space, you're leaving some value on the table, right? If you go to go do another job and you're not going to leverage this network, it's, you're cutting off some of the value.

But it was the first time I started thinking about it. So I started thinking about that. And in the midst of that, I had a coaching client that was completely outside the WordPress space. And I just mentioned to them, Hey, I may be leaving my job at Liquiweb. And it was a job at Liquiweb, but I was also the GM of LearnDash.

So I may be leaving both of these gigs. And they, they went into hyperdrive,

Brian Casel: acquired LearnDash. And so then you became the,

Chris Lema: yeah, I came in the guy on LearnDash. They went into hyperdrive. They had an [00:14:00] emergency board meeting the next morning. And by that afternoon, they had an offer. Well, the original guys were two weeks into interviews.

These guys were like. If you're thinking about moving on and you're open, Cherith is the name of the company and, uh, Cherith said, we want you over here, right? If you'll do it, right? That option was, was so. Interesting and inviting that I call the duty guys back up and said, Hey, take my hat out of the ring.

I know you have at least one other candidate go with them. I'm going to go with these guys. This is exciting to me.

So I joined a company called Cherith analytics that no one's ever heard of, at least not in any of our spaces, but frankly, in almost any space, no one's ever heard of them. They're a group of, uh, AI researchers along with linguistics AI, which is a field that I'd never heard of along with some security experts.

In the overall space of what's called faith tech, which is technology used for mission oriented organizations. Some of what they do is some pretty quiet and on purpose, right? Uh, [00:15:00] product work of taking content behind China's firewall, the great firewall. And making it available even in the midst of all the work that China does to slow down the Internet other than for local servers and to monitor.

It's a surveillance economy, right? The entire gamut of your phones, your websites, your web traffic. All of it is monitored by the state government. So how do you build proxy servers to mitigate some of this and to speed some things up? And there's a lot of technology in it and there's a lot of, uh, interesting new tech, but they were looking for someone to help them productize, think about product strategy, turn some things from research into actual practical products.

It's interesting. And you go, okay, yeah, I can do that. But it has nothing to do with WordPress at all.

Brian Casel: Yeah, no, it's like, it's like so different. And it sounds like, is it like aimed at like large organizations? Like very enterprise sort of tools or are they going?

Chris Lema: It's both, right? Like it's one of the products that we have already out in [00:16:00] market is.

The most read Bible app for iPhone or Android on the globe because they have 10 million Chinese people reading it every day. The problem is, is that that app to download that app, you have to keep moving where the download link is. Every few hours, because the government's trying to shut it down. So, I mean, it's a, it's a whole different problem than other kinds of problems.

But that was exciting, right? They give you an opportunity to do a job and they go, Chris, there's a whole bunch of challenges and you go, Oh, I like challenges.

Brian Casel: Let's go do it. Yeah. I mean, I, I could see how, like, when you're at a point where you're, you're feeling kind of burnt out, you've been doing this thing for multiple years and, you know, and it's like a totally fresh problems that an opportunity just kind of lands on, on your lap.

Chris Lema: And it's, uh, it's a crazy thing in the last 3, in the last 3 months, I'm involved in buying a company. Which I've done 40 times already, I'm involved in [00:17:00] investing in a company, which I've done 30 times already. I'm involved in starting a new startup, which I've done 7 times already. And I'm launching a product, which I've done probably 100 plus times already, right?

I literally don't have to prep. To walk into any meeting, I walk in the meeting and I'm like, Oh, I have a framework for that. I have a strategy for that. I've done that before. Here's the questions I would ask. These are the lawyers I would use. This is how we do it. I would do this tranche and then do this flip and then do this convertible note and then do the benefit of having done a whole lot of work for a lot of years.

You know, if you get the opportunity to work in a job where you're like. I've never worked harder, but I've also never, it's never been easier because it's leveraging all the things that I've done before.

Brian Casel: A lot of business fundamentals just don't really change no matter which space you're in. You know, you can, you can apply what happened on that deal over here.

Very cool. Very cool. So, I mean, at least in the last several years, I feel like Cabo Press might be like my only like remaining connection somewhat to like the WordPress [00:18:00] world and some, you know, friends who work in WordPress. But like, I, I still feel very disconnected to like. What's going on in and around WordPress.

I'm curious to know your take. Cause I, one thing that I just noticed from afar, I think it's hard to not notice this is like for so many years there, WordPress was like the no brainer. Why are you even considering any other CMS, right? Like, yeah, like Squarespace was out there for a while as well. But like Webflow flow just seems like a giant.

And then there's other ones coming up that are starting to like chip away at WordPress, maybe more than chip away. I mean, what do you think about that? I'm still like, just kind of hard code, like static sites, you know, but like, what's the landscape looking like now? Is it actually getting more fragmented than it was?

Chris Lema: Yeah. So five years ago, six years ago, The one that nobody knew about was a GoDaddy's website tonight, and you were buying a domain name from GoDaddy. And then they would say, Hey, do you want a website tonight? [00:19:00] Because you can just click this thing and we'll give you a website.

Brian Casel: That thing is probably powering like so many.

Chris Lema: It powered more websites than Wix, Weebly, and Squarespace combined. And nobody put it on a list, right? Nobody had it on the list. Maybe, you know, Matt Mullenweg, maybe WordPress had it on the list, but those of us that are talking about new CMSs and drag and drop and whatever. Nobody had this go daddy product on the list.

That's kind of what, you know, you realize for go daddy and for WordPress is we've never been good at marketing, right? Marketing just wasn't, they didn't have for the longest time, the WordPress project and automatic, which are two separate dynamics, but still had no marketing staff, right? And so if you're not marketing, and by the way, if you're go daddy and you have a website tonight, you don't market, it's just a post purchase upsell.

Like, Hey, you bought a domain, you know? So it's a carry on product. When I went to go build the WordPress. Offering a liquid web, I'm sitting there talking to one of [00:20:00] the execs at GoDaddy, who's a buddy of mine. And I said, well, I finally, I got us to 2 million in, in ARR. He's like, that's awesome. I go, yeah, I know that's nothing compared to what you do at GoDaddy, but remember that at GoDaddy, you can just do a one click upsell to buying a domain.

I'm starting from nothing, like they didn't know that we existed. I'm competing against 10 other hosts that already do manage WordPress. And now I'm sliding in to take a corner. So, you know, in those days, Wix, Weebly, Squarespace, and they combined barely made us, you know, a low single digit percentage difference in the, in the world.

Right. So WordPress. WordPress was growing and also WordPress was not looking at, okay, who's the competitor at 1%, right? Like that's just not interesting.

Brian Casel: It's so interesting to me how, like, it's such a great case study in just understanding what your true competition is, right? Cause like every WordPress plugin startup is looking at, well, who's my competition?

Oh, it's the other WordPress plugin that does sort of the same thing as it was mine. It's [00:21:00] like, no, there's a whole ocean of other customers who don't even know what WordPress is. Let alone Wix or Weebly or whoever, you know, whoever it is, you know? Yeah.

Chris Lema: So then Webflow who had been out for a little bit, you know, kind of grew itself into a contender along with several others, right.

And there is a little more fragmentation. The problem is that at the same time that those were all growing up and we see them a lot in the U S. In the parts of the world that are growing rapidly in terms of website adoption. So Bangladesh, India, Pakistan, et cetera, those places were picking up WordPress for a hundred rupees, right?

1. 99 a month in hosting. And so we went from like 32%, 33 percent to 43 percent in a very small span, right? It grew. But when it grew, it wasn't growing in the U S right. So you hear these words like, Oh, there were 33 and 35 and [00:22:00] 38 and 43 percent of the internet and you're like, yeah, but in a part of the world that pays a hundred rupees a month, not in the world where we pay 20, 50, a hundred dollars a month.

Right? Like, let's just, let's just make sure we're clear on, you know, where it's growing. And so, because of that adoption. Even when Webflow was growing, it's going to be a very hard and small percentage growth such that you don't feel like you need to worry about it. Right. And this is when we talk about crossing the chasm, right.

And you talk about the old school marketing literature that tells you how to market software. When you look at crossing the chasm, when you look at Clayton Christensen, right, who wrote about the upmarket climb, right. And less for less, and this ability to say, Hey, when laptops. Are like, you know, worried about multiple GPUs and CPUs, and we're getting the M one and the M two chip.

Right. And so you're saying there, [00:23:00] nobody looks at a Chromebook as a competitor, right? But the Chromebook is a competitor. It's a less for less solution and many, many pieces of hardware, right? Laptops specifically. Are used for email and maybe a spreadsheet and you can do that with a Chromebook. And then just as the Chromebook does the upmarket climb and starts moving up and we finally get Samsung releases a thousand dollar Chromebook when it used to be a 200 device.

The iPad comes in and does less for less, right? And says, Oh, I think you can do everything on an iPad. So. There is this constant dynamic where the, you know, the folks that are building a product like the M2, you know, Apple MacBook air are looking at a Chromebook and saying, that's not a competitor. And the Chromebook is looking at an iPad and saying, that's not a competitor, but there's a moment in time where things shift.

And all of a sudden the audience says that that went over the line. I don't need to buy that for what I do. I'm fine with a Chromebook or for what I do, I'm fine with the, with the tablet. [00:24:00]

Brian Casel: Again, like it sort of like comes back to this whole thing. It's like competitors or just products in a market might seem so prominent when they're still so invisible to so many, like, like even like Webflow right now seems like it's, it's really catching on because like almost every other software business I know they're, they're tending to choose Webflow instead of WordPress.

Like they did a few years ago when they need to get their marketing site, CMS up and running, like most people are reaching for Webflow, but that's just the people that I see. And that's right set us based SaaS software, not us based, but like, you know, SaaS software people, which is such a tiny market, you know, like most of the world is just catching up to WordPress now.

And now it's coming up behind it. Right. That's right.