How to Find the Right Tools for Creators (and Why an Open Platform is Better) with Jack Kitterhing
S1 #261

How to Find the Right Tools for Creators (and Why an Open Platform is Better) with Jack Kitterhing

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[00:01:00]

Joe Casabona: Jack Kitterhing has been in the WordPress space for a while. You can say he deeply subscribes to the ethos that owning your own platform is one of the most important things a creator can do. That a SaaS like Teachable won’t be there for you like your own platform, something like WordPress and LearnDash.

We have a good discussion about the merits of both. And try as hard as I can, I can’t get Jack to admit that maybe a SaaS is better in some cases. But we cover questions like, is it really easy or is it really easier to set up a course on Teachable? What are the benefits of owning your own platform? We get into all of that and more on this episode of How I Built It.

This episode of How I Built It, by the way, which is brought to you by NitroPack, Tailor Brands, and Nexcess, you can find all the show notes and learn more about them over at howibuilt.it/261. But for now, let’s get into the intro and then the interview.

[00:02:10]

Joe Casabona: Hey everybody, and welcome to How I Built It, the podcast that helps small business owners create engaging content that drives sales. Each week I talk about how you can build good content faster to increase revenue, and establish yourself as an authority. I’m your host Joe Casabona. Now let’s get to it.

Real quick, before we get started, I want to tell you about a free weekly newsletter I’m doing called Creator Toolkits. I want you to become a more efficient creator. It’s the whole purpose and mission of this show. I want you to be able to free up more time to create, to get more sales, and to make more money. And you’ll be able to do that with these free weekly tips delivered to your inbox every Wednesday morning at 7 a.m. with the Creator Toolkits newsletter.

As a thank you for signing up, you will get a free content planner that I use personally with YouTube and podcasting. That is built-in Airtable. You’ll get that completely for free if you head over to howibuilt.it/airtable. Become a more efficient creator with free weekly tips delivered directly to your inbox every Wednesday morning at 7 a.m. eastern over at howibuilt.it/airtable.

[00:03:31]

Joe Casabona: Hey everybody, I’m excited to be here with Jack Kitterhing. He is the product manager of LearnDash, which is my favorite learning management system. They are part of the Liquid Web family. And full disclosure, Nexcess is a sponsor for this entire season. That has no influence over anything I say about any of their other products or who I have on as a guest. I thought Jack would be a really good guest for this topic, which is evaluating tools, especially for creators. You’ve heard enough from me. Let’s bring in Jack. Jack, how are you today?

Jack Kitterhing: I’m good. Thanks, Joe. How are you?

Joe Casabona: I’m doing very well. Thank you. I’m excited. I’m a big fan of LearnDash. I have been for a long time. I met Justin Fairman and he was on this podcast way back on like Episode 32 or something like that. That’s over 200 episodes ago because this is Episode 261. And he imparted some great advice, but I’ve known him since 2016.

I’ve been using LearnDash that long. So when I heard that LearnDash was joining the Liquid Web family, I was excited because everything you guys are doing over there is great. And then I found out that my good friend and two-time guest on the podcast, Chris Lema, was taking over as the general manager over there. So I was even more excited.

I’ve also been following you on Twitter for a while, I think probably because Justin was retweeting you, and you’re too kind of doing interesting things. One of those things was acquiring old dot org plugins and reviving them and working on them. So I’m excited to have this conversation. But before we do, why don’t you tell us a little bit about who you are and what you do?

Jack Kitterhing: Yeah, sure. Obviously, you guys know my name. Thanks for the introduction, Joe. By day I’m a product manager at LearnDash. I started off with WordPress when I was about 12 years old. The very first website I built was for retro gaming. So if you’re into snares and retro Mario Kart, and you want to run over banana, I’m the guy.

Joe Casabona: Awesome.

Jack Kitterhing: I’ve worked in variety of WordPress companies and roles. I’ve been everything from a support manager, QA, QA engineer, developer, product manager, I’ve done marketing and product, I’ve worked across WPMU DEV, which had I think, at the time, and still maybe does like one of the largest plugin catalogs in the WordPress space most probably. I worked at MailPoet prior to the acquisition by Automattic. I left about a year before that.

Joe Casabona: Nice.

Jack Kitterhing: And yeah, I originally come from southeast London. So if you get a weird accent that’s because I’m not American.

Joe Casabona: That’s right. They get a weird accent every week on this show because my New York accent comes out sometimes. Awesome. Well, yeah.

So it sounds like you’ve been around the block doing kind of every role in the WordPress space. Now, you mentioned that you are also a developer. Was this like when you were 12 you started developing? Is that still part of your day to day? Does it help you inform how you guide the product?

Jack Kitterhing: I started actually developing when I was about 10. I first picked up HTML and then I slowly progressed to JavaScript, PHP. I don’t particularly use it in my day to day now, but it definitely helps inform. As product manager. I can speak to the developers like I can speak to the marketing people. So I can understand when a developer is explaining scope to me and we’re trying to go over like, is this actually doable? And I understand how technical it is as opposed to just trying to force them do something that timeframe is impossible.

Joe Casabona: Yeah, which is a really important skill to have that very few people have. I’ve been told I have the same skill. I have a master’s in software engineering and I know that I was never as good a coder as will say the developer is to people in my program. But my thesis advisor said, “Yeah, but you have people skills, which is really important.” I don’t think I would trade-off. I’m really glad to be kind of that good development skills, good people skills balance. Because I don’t think we see that in a lot of people.

Jack Kitterhing: Yeah, no, I don’t think we do. I think we see that there’s a lot of people that either have one or the other. And sometimes you speak to a developer, especially more senior ones in some companies, and they feel like you don’t understand what they’re saying. It can be a very difficult relationship, especially to kind of have them to trust you in taking that product forward because they want to know you know what you’re talking about.

And even if you know it from the customer side, if you don’t know from the technical side, you really need that middle person that can collaborate between you. So it really helps sort of streamline the process.

Joe Casabona: Yeah, absolutely. And trust is a really important facet of that, of course. But it is tough when even like developer to developer, you know, when I worked in higher ed and we brought in consultants, there was always that kind of sniffing around. “Oh, do you really know more than me?” Like you’re getting paid more than me but…” So yeah, it’s forming that relationship and kind of being able to speak each other’s language is really important.

Now you, you are the product manager for LearnDash. We had a little bit of history in the beginning. And LearnDash is an LMS plugin that sits on top of WordPress. This show helps creators and small business owners leverage tech and create more consistently. And I think one of the toughest decisions or one of the toughest aspects of being a creator is what platform do I publish on? Where do I put my work?

Because on the one hand, you want to be able to own as much as your platform as possible. But on the other hand, you want to spend your time creating. You don’t want to spend your time managing your website. So I think kind of trying to figure out how to strike that balance is really important.

So I know in the pre-interview we talked about how you’ve used Teachable and Podia and of course, some of the other WordPress LMSes. Oh, what’s your kind of general philosophy on finding the right tool?

Jack Kitterhing: I think it’s an interesting point. Because obviously WordPress brings with it a lot of facets where, you know, you need to update plugins, you get that security notice right, you get the scary email that says, “Oh, this plugin needs a major update,” and then you’re like, “Oh, I’ve been hacked or what’s going on?”

Ultimately, I think it comes down to your kind of skill level, but also your comfort level. Do you have someone in your arsenal or can you find a company that can manage it for you? So I think WordPress-managed SaaSes are a great way of being able to actually go ahead and use WordPress whatever you want to use it for.

Because traditionally, WordPress is always cheaper than a SaaS base route. But a SaaS stuff is always more expensive. So if you’re a small business owner, you’re just getting started out, the SaaS stuff may save you some time, which can be valuable obviously because everyone values their time.

But if you haven’t actually got the dollar investment to make, especially if you’re not coming from an American based country, you’re not coming from one of these countries or has a high economic output and maybe you’re looking at the cost and being like, “That monthly cost for Teachable is perhaps like a quarter of your salary in your country,” and then you’re like, “Yeah, that’s just too high a cost. So what do I do?” Many managed WordPress hosts are incredibly cheap by the way now, right?

Joe Casabona: Yeah.

Jack Kitterhing: When I first brought like WP Engine multiple years ago, I paid like $300 a month and got like not a lot for. Now, they’re just getting cheaper and cheaper and cheaper. You’ve got all the great players in there. Obviously, you’ve got Nexcess with their managed host, [inaudible 00:12:11] Liquid Web. I’ve used Kinsta extensively as well in the past.

There’s so many that are so cheap and they take care of everything for you. They take care of the security, they take care of the PHP site. They take care of all of the tech stuff. They got their automatic updates, their automatic backups. If stuff goes wrong, it’s super straightforward to get it resolved with them.

I think really that’s where my philosophy would be is can you afford it? Obviously, if you want the ultimate ease of use genuinely, a SaaS is easier because you’ve not got a configure plugins. You haven’t got a [inaudible 00:12:47] I think I need this.

But what you lose with a SaaS is also you lose the flexibility, right? If you go to Teachable and they haven’t got a feature you want, you can’t go to Upwork and post for a developer to code a feature for you because they can’t hook into Teachable system. But if you install LearnDash and you see, “Oh, I want this cool feature that LearnDash doesn’t have,” it’s an open-source platform.

You can go and find… there’s plenty of top-tier LearnDash developers. We’ve got a Facebook group with over 20,000 people, there’s some great developers in there. There’s some great guys and gals that do these extra plugins for LearnDash, these add-ons. I think the last count, you know, there’s like 85 add-ons for LearnDash.

Joe Casabona: Wow.

Jack Kitterhing: There’s multiple talented teams that can build world-class solutions. And you don’t get that with a SaaS.

Joe Casabona: That’s exactly right. I mean, I’ve coded a couple of my own little menial utility plugins for LearnDash. None I think are ready for primetime. But they did something specific that I wanted. I think at one point I was using like ACF for the video URLs so that I could more suitably place them in the template where I wanted.

And then when 3.0 rolled out, the templates got a lot better and then I thought, “Well, I should really convert all the ACF URLs to proper LearnDash video URLs. And I wrote a little plugin to do that. So yeah, absolutely, you do have the flexibility.

I like to put it in terms of do you want to rent or do you want to own? Like renting an apartment means that you probably can’t paint the walls or change the kitchen countertops or whatever. But it also means that if your heater breaks, you’re not on the hook for fixing it. Whereas when you own a house-

Jack Kitterhing: Exactly.

Joe Casabona: We put in a new shower stall and a whole bunch of other things in our home, but our HVAC broke and we had to pay around nine grand or whatever to get it replaced. So you need to determine kind of, like you said, what Jack said, what your comfort level is. Do you need that flexibility? That’s kind of self-hosted versus hosted. Do you have a favorite SaaS solution? I’m basically going to ask you to pick your favorite competitor. But is there one…

Jack Kitterhing: Joe. He’s trying to get me fired, people.

Joe Casabona: Well, I think we both know Chris. I think Chris will probably yell at me first. What I like to tell people when they’re first starting out, especially if there’s a free tier for some of these SaaSes is proof of concept it on the SaaS. Right?

Jack Kitterhing: Right.

Joe Casabona: And then move it to LearnDash. And yeah, there’s going to be some headache moving it, but if you’re just starting out, you might not really know what you need until you need it. So I guess what that, you know, Teachable is the big dog I think as far as a SaaS goes. Podia I guess it’s been around for a while that I’ve just recently heard of.

Jack Kitterhing: I suppose it’s been around a while. I guess they just come into it with their own… They’re very community-driven. Like community way of learning and thus becoming more and more popular with cohorts and everything. So they’re pretty big on that.

You know, long back prior to joining LearnDash, I used Teachable. I like Teachable. I got nothing against Teachable. It’s a solid platform if you’re getting started out. I guess if I had to pick one, I would pick them. If Chris listens to this, Chris, I’m sorry. Don’t fire me.

I think one of the biggest problems, like you pointed out, was that when you want to move platform, it can be a pain to move a platform. It’s not a straightforward thing. The content does come over one for one and it can be a manual process. It’s not necessarily an automatic process. And quite often someone says, “Well write a script.” And you’re like, “Yeah, but to write a script it’s going to take me x amount of hours.” And by that point, I could literally just copy and paste the content.

Joe Casabona: Do I script it or do I just do it?

Jack Kitterhing: Right. Yeah. Do I spend days writing the script and then breaks? Obviously, I think at that point you’ve got to consider like, is it a one-time use? If you’ve got an interest in selling that script to someone else, then quite often it’s easier to get someone to copy and paste content for you. If you’ve got a new assistant, they got a perfect job. Move the content.

Joe Casabona: That’s my VA, God bless her, she is in charge of a lot of that stuff. But yeah, I think you’re absolutely right. Now, I will say, I’ve heard that Teachable is probably good. I heard that Teachable is terrible for memberships and subscriptions, though, which is in my opinion the best features that LearnDash has rolled out in like the last year is that membership. And now subscriptions support.

I’m using WooCommerce subscriptions. So I think I’m stuck on that because I don’t want to migrate all of my customers over because that’s like a big pain. But thanks to LearnDash’s membership feature, I was able to drop the $200 a year WooCommerce membership plugin I was using. And now that plugin got acquired and I don’t have to worry about offending my friends, I think, who made it. I mean, that feature alone saved me a bunch of money and it was super easy to implement. And then I had less dependency for the same functionality.

Jack Kitterhing: And that’s what we’re trying to do. We’re trying to make LearnDash straightforward and simple for like a small business owner, someone that wants a great course, an expert. But we’re not missing out the other people. We’re not missing out high rate, we’re not missing out the person that’s trying to create corporate training, things like that.

But if you’re a subject matter expert, you don’t want to install LearnDash then need WooCommerce subscriptions, WooCommerce memberships. Any of that expensive plugins they’re also incredibly complex to set up. You see people will try and figure out in the Facebook groups like, “Oh, what buttons do I need to press? What tools do I need on? How many billing cycles is this?

So if you can just get LearnDash install it, you can be like, “Oh, this is great. I don’t need to do anything else.” Obviously, maybe I shouldn’t reveal it, but that’s part of LearnDash 4.0. So the upcoming LearnDash 4.0, nice onboarding wizard get people started quicker.

Joe Casabona: Awesome.

Jack Kitterhing: It’s always about getting them in the door and helping them create their course. Because that’s where people get stuck. So many people buy a course plugin, they sign up to a SaaS and they never even launch their course because they’re just too confused by how to actually create the course. So you need to take care of that set up for them, and then just let them create the content because that’s what they are. They’re experts in what they do. And that’s what they want to teach.

Joe Casabona: Absolutely. I love that. I’ll just say a couple of other things here. It sounds like my boot camp videos are getting less and less relevant as time goes on, which is… I should say that those videos have landed me a couple of coaching clients. People reached out and they were like, “Hey, you’re the guy who does the LearnDash videos, right?” Can I hire you?” I’m like, “Yeah.”

But that’s really great to hear. And then another aspect is you mentioned it earlier, managed hosting, managed WordPress hosting. Again, I’ll throw in that full disclosure that Nexcess is a sponsor, but their StoreBuilder and WP quick site are two tools that I reckon. I mean, this is high speculation. So I won’t speculate. But those tools make it really easy to bring parody to WordPress versus other SaaS, where you just sign up for an account and now you have a membership site with Restrict Content Pro or you have a WooCommerce site with StoreBuilder. So I can definitely see more WordPress products going that route. I think as we record this Elementor just launched its own hosting-

Jack Kitterhing: They just launched Elementor Cloud. I think you see people trying to remove friction in the WordPress space because WordPress has always been a friction heavy kind of marketplace. They say, the famous five-minute install. It’s a famous five-minute install, but you got to go and register domain, points on DNS, find the host, upload the files, connect to FTP. What’s FTP? Someone doesn’t know that.

Joe Casabona: The database. I installed WordPress from scratch recently and it all came flooding back to me. I’m like, I actually have to go in and make a database. It’s a five-minute install when the hosting company is on board. And they’re like, Oh, we’ll make the database automatically or whatever. But yeah, like a five-minute install with all those caveats you just mentioned.

Jack Kitterhing: Yeah, exactly. It’s not a five-minute install. Depending on your technical capabilities it is from five minutes to five hours.

Joe Casabona: Right.

Jack Kitterhing: And a lot of head-banging. And I think that’s where companies are trying to go is almost removing the WordPress layer. So you’re keeping the flexibility of WordPress, but you’re not keeping kind of the stuff that makes it hard for people to get started. You’re seeing more and more plugins with wizards.

I don’t like the term necessarily of a wizard because I always think of a wizard as kind of like, well, do you think I’m stupid? Do I need this wizard? I’ll serve myself. It’s not that. It’s more like a quick start. Kind of like using StoreBuilder.

Obviously, I do work at Liquid Web, to go with Joe’s disclosure. StoreBuilder has that great thing where it removes that layer of friction between WordPress and WooCommerce. A lot of people sign up to StoreBuilder and they’re not signing up because it’s like hosted WooCommerce or it’s not hosted WooCommerce. They sign up because it’s a way to get an eCommerce site quickly on WordPress with flexibility. It’s not about it being powered by WooCommerce. It’s not anything to do with WooCommerce. They just want an eCommerce store on WordPress without the struggle.

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Joe Casabona: You know, to call back to kind of me asking you to pick your favorite SaaS, your favorite kind of competitor, I think soon it’s really not going to be a comparison, right? Because you look at like LearnDash, I think that part is getting a lot easier. And that’s kind of what I base my whole membership on over at Creator Crew. It’s like, “How to have your own platform.” And I don’t exactly say it that way. Because nobody’s like Googling like how to have my own platform, but how to leverage the right tools.

And unless you’re paying Teachable like hundreds of dollars a month, they’re taking the credit card fee, and then a little extra, right? I think it’s like 10% for the lowest plan. That’s a big chunk of change.

Jack Kitterhing: It’s huge. That’s why people stopped selling on eBay, right, because of the eBay fees. You got to consider. People want to take the million dollars in sales, and then they lose like 100k of that. You know, they pay all the taxes on top, they pay their staff and you’re like, “Oh, shit, I’ve lost half my money. Where did my money actually go?”

That’s also what you get with something like LearnDash or a WordPress plugin is you get the fact that the sales are yours. You make that sale, you pay Stripe their 2.9% or 2.4%, wherever they take and then the rest is in your pocket. That allows you as well to build a better site. You can build a better business, you’ve got more money to hire people. Like if you take a lot of money and you’re paying a company 10% to kind of handle your sales for you, imagine if you can invest that 10% into your business as opposed to paying it out to a SaaS.

Joe Casabona: Right. Right. Yeah, exactly. There could be benefits, right? If Teachable had like a featured course every week and you knew that your course would get featured, and that that would boost sales like 500%, maybe that 10% is worth it, right? But they’re too big at this point to do that. Just like Udemy is… I mean Udemy is like highway robbery in my opinion. But that’s maybe for another time.

Jack Kitterhing: That’s a whole two-hour conversation.

Joe Casabona: I know. I have strong opinions. Gosh, I spoke to… Oh, man, it’s really going to escape me. I spoke about on a previous episode, though, so I’ll link it in the show notes, which you can find over at howibuilt.it/261.

So that’s kind of WordPress versus SaaS. I feel like we’ve heavily guided the listeners towards going the WordPress route. There’s also a lot of competitors in the WordPress space. Tell me if I’m wrong. I would suspect that Lifter is your biggest competitor. Is that accurate?

Jack Kitterhing: Yeah. So Lifter LMS is up there. And then Tutor LMS kind of started gaining more popularity. I would say I think actually if you look on wordpress.org, Tutor LMS has more active installs than Lifter now at this point.

Joe Casabona: Interesting. And both of those have a freemium model, right, where you get some, some functionality for free?

Jack Kitterhing: Exactly. So both of them have a freemium model, which does drive people to kind of try them first. They also have that model where you know.. I can’t speak much of Tutor LMS’s pricing right now. But yeah, lifter LMS, for instance, if you want everything and you want advanced quizzes like what LearnDash has, it’s almost like $1,200 a year. And then LearnDash is like $159. And there’s so much in LearnDash for the price. I know I work there, but even if I didn’t work, there is incredible value for what you get.

Joe Casabona: I will vouch for that. I think maybe the biggest pricing model difference between Lifter… Lifter is the one I’m most familiar with outside of LearnDash, is that lifter kind of offers kind of not ala carte pricing, but it’s like there are different packages. I feel like LearnDash is the more ala carte, where you get the core functionality for a very low price. And then maybe you need to buy a couple of add-ons to do this and that.

Jack Kitterhing: Right. I mean, we include LearnDash develop add-ons in the price. So you get the 15 LearnDash develop add-ons. We release new ones consistently. Like last year we released Achievements and Integrity. So Integrity helps protect your courses and your content.

I think there are kind of these add-ons that maybe some people want. So for instance, you want to create a Udemy style site, there’s a great plugin for that for LearnDash. You can create a Udemy style site with LearnDash. And there’s so many ways you can do WooCommerce as well if you wanted to or multi-vendor marketplace.

But I would say like, if you’re a core course creator that really LearnDash does include most of the functionality you need. There’s very few instances where you’re a subject matter expert and you’ll be like, “Oh, now I need to spend another $500 on some other add-ons.”

Joe Casabona: I agree wholeheartedly with that. I use LearnDash Core and their included add-ons. And then like I said, I’m only using WooCommerce subscriptions because when I started using LearnDash six years ago at this point, it was not a subscription thing. But I mean today memberships and subscription I think in its purest form it’s really… I can’t say enough nice things about that feature specifically. I just love it.

And then there’s the Stripe add-on, which I think is… Did I read in the Facebook group that’s getting built into… you won’t need an add-on for that soon?

Jack Kitterhing: Right. Yeah. So we’re actually getting Stripe Connect into LearnDash Core. So Stripe Connect is so much easy way to get started with Stripes. You know, just hit that “connect” button, login or create Stripe account yourself and ready to go. So you know, no more faffing about with keys and webhooks and certain stuff in Stripe.

Joe Casabona: I wish you told me that because I just put a YouTube video out on how to do the whole thing. That’s really good. Because Stripe has changed considerably over probably the last two years, right? Year or so.

Jack Kitterhing: Yeah. Stripe changes considerably. I love Stripe, especially as a developer, they have fantastic documentation. But they’re always updating their endpoints, their webhooks, and everything you need to do. Sometimes I hit LearnDash with the Stripe add-on, we would release an update and then we’d be like, “You have to go into your Stripe dashboard and have to edit this setting and this setting for it to actually work. And that’s very confusing for people. They were like, “Why do I have to do that? Stripe work forever.” So Stripe Connect is great. It’s well taken care of.

Joe Casabona: Awesome. Awesome. I guess what I’m really digging at here… Because I don’t want you to just say, you know, keep talking about your competitors and all that. But there are different needs and different feature sets. I guess, what do you recommend for the creator as they’re evaluating all of these options?

Jack Kitterhing: So I think what you need to do is you need to really step back and think about your learners. You need to create the persona of who is actually going to be taking your course. It’s no good just coming at it and throwing some content on a website and thinking people are going to come to it and take your course, because they’re never going to do that. There needs to be targeted…

I know, Chris is a big fan of microsegments. You need to segment your users on what they’re looking for. That will really inform your decision of a platform. Because once you define the segments, you know what features you need. Then once you know what features you need, you can go ahead and do a comparison across them all.

I would say that you should always pay attention to comparison pages on anything like a SaaS, or a WordPress plugin because they’re very creative. Like you see on some of these places, and you’re like, “That’s not really accurate but okay.” I think do your own research and find trusted experts and find YouTube reviews and real users.

Once you have the segments, you can go and be like, well, you know, products you need like Zoom integration. So then you go and you look at every platform has Zoom integration. And then you work out the cost. Is it in core? Do you need to pay extra money for a third party? How well support is it? How integrated is it?

And you can work out then the cost of what you need. Because a lot of people make the mistake, they jump into a course platform. And then they find out after they’ve created their course, “I need these 10 features.”

And then if you’re in a SaaS like Teachable, most probably you got to move because you can’t do it if they don’t have the feature. If you’re on a WordPress plugin, you either find out that you need to pay thousands of dollars to a developer to build it, or you need to go and spend $1,000 on third party add-ons. That’s really important that you figure out what segments you’re targeting so you know what features you need.

Joe Casabona: I think that’s a really good point. I’ve talked about this a lot. Because my approach is always you always came with the hubris of using WordPress since like 2004. So I’m like, “I probably know what I’m doing.” But when I first launched my online learning site, it was using Paid Memberships Pro and WooCommerce, and Sensei.

And then I started using LearnDash, and I thought, “Well, if I’m using WooCommerce anyway, why would I use Paid Memberships Pro besides the fact that I know the Colemans and I live like an hour away from them?” But it wasn’t really the right tool for the job. And then LearnDash has changed and includes a lot more.

Then I went and did the same thing for the How I Built It membership site where I built a whole new membership site. And I’m like, “Why didn’t I just put this in my other site that supports memberships?” That’s a cautionary tale. I was just kind of like, shoot, first ask questions and let’s see if I could do this. But like you said, the important thing to do is make a list of your most important features.

Jack Kitterhing: I think you made a good point as well. Because when you got a membership plugin, you got an eCommerce plugin and then you’ve got platform planning. And so platform planning is something like LearnDash, something like that. And each plugin has a registration process, each plugin needs WordPress login, WordPress registration.

I see it all the time, people get so confused in different Facebook groups. They’re like, “I’ve got these five plugins, and they all had a registration differently. And I’ve got like six registration pages. Where do people go to login in them?”

That’s one of the reasons we added subscriptions and memberships to LearnDash is to create that streamline process. And if you just got one plugin, it’s one process. That’s really important, especially if you’re not a developer-type person. You don’t want that confusion. Because yeah, when you get all these plugins together and they’re like, “Well, where do I go to login? I’ve got four login page.”

Joe Casabona: And emails too, right? This is another thing. I had someone sign up for my newly minted membership and I had the LearnDash notifications on except I had it so that when you purchased a product, WooCommerce would automatically register you for all 10 courses. And then I had a generic email them whenever they register for a course.

Now my users are getting the receipt, the account information, and then 10 emails for each individual course that they’ve registered for. I’ve since turned that off. Now I think LearnDash also lets you send an email after the first lesson or maybe it’s a Zapier trigger. I set up something a lot better where they basically get an email explaining everything. And then at some point, in the course, they’ll get an email that says, like, “Hey, good job. Do you have any questions or whatever?”

Jack Kitterhing: I think that’s a great point is that QA your product before you launch it, right? You know, you start a new website—I’ve been in QA for a while—always go through the steps as an end-user. Completely take a step back. And even better if you’ve got a friend that you trust. Give your friend the site link and like, “Does this make sense to what you receive?”

Because it’s so easy when you’re the one building it to kind of get lost in it and be like, “Yeah, this makes total sense.” Then someone else steps in with a fresh pair of eyes and they’re like, “This makes no sense at all. It’s the most confusing thing in the world.” And that will really help you as a creator to kind of figure out the processes that you want to put in place. Because if you get like 50 emails when someone signs up and then they’re like, “What’s going on?” Sends it right into spam. You kind of hurt your email sending reputation before you start.

Joe Casabona: Yeah, yeah. Ramli John has a really good book. The name is escaping me. I’ll link it in the show notes, though. It’s all about like the user onboarding experience. And this is what inspired me to test the whole process myself. Because again, it’s easy… I’m a developer. I’ve been using WordPress for a long time, so I assume that things will work the way they’re supposed to. But you shouldn’t ever do that, especially if you’re bringing a bunch of tools together.

So I think kind of bringing it back around, list out the most important features for your learners. Do that ideal customer avatar. Who’s coming to you? Is it like a mom with three kids who’s trying to learn because she got the glorious simultaneous naptime of all three kids? Which by the way, my wife and I achieved that over the weekend. Or is it somebody who has to learn for part of their job? They’re going to have different experiences. You figure out the right tool and then test and work through it yourself and see what the onboarding experience is like.

Jack Kitterhing: Exactly. Onboarding is so important to the process. That’s where you gain. You literally can turn someone out on onboarding. Onboarding is so bad, and then they’re just like, “I’m not going to use this.” That’s a refund request or they just churn. Obviously churn is important for everyone. But if you’re a small business, you don’t want to be churning customers before they start.

Joe Casabona: That’s exactly right. I tweeted this like back in August, and then somebody just responded to it like yesterday. But I thought it was baffling to me that in WooCommerce you can’t customize the “thank you” page without a… I think it was a $50 or $99 add-on.

They’re like, “Well, WooCommerce model is it’s free and then they make money on the extras.” And I’m like, “Yeah, but my point is that shouldn’t be an extra.” I feel like the “thank you” page is a core part of the purchase experience, especially if you’re going to sell digital products or login information.

I think another Liquid Web product, Cadence… one of cadences products, allows you to do that customization. They have like the WooCommerce emails customization too. This is all a lot to think about but it’s all important… I guess this is kind of a tangent. But the more-

Jack Kitterhing: That’s a good point because I think a lot of people in WordPress feel like they’re nickel and dimed. Like if you’re new to WordPress and you kind of get that thing where you see it’s free, it’s cheap. You know, you see these famous like GoDaddy $5 hosting, Bluehost super cheap hosting and all these super cheap deals.

But then you actually get into and you kind of feel nickel and dimed because you go and buy a premium plugin and you get to that point where you think, “Well, now I’ve spent like, $1,000. I need to spend another $3,000. Now I need to spend $2,000 or a consultant to actually put it all together for me.”

It’s quite easily dung where you spend too much, but it wasn’t planned out. If you’re a small business owner, you’re a creator, always plan out what you’re trying to build, because then you know what you’re getting into before you start. Too many people just dive into picking out a host, installing WordPress, and they chuck tons of stuff on it. It’s like a kid in a candy store. They put every candy in the bag and we’re trying to figure out later. And that’s kind of like, you know, you end up with a stomachache.

Joe Casabona: Yeah, exactly. I think it’s important to have a good guide here to understand what you’re doing. Because this can sound overwhelming. This sound overwhelming to anybody who’s like, well, I just want to start an online course. And this is why kind of laying out those requirements is important and picking the right tool from the outset is important. So kind of like we’ve talked about, right?

My issues stem from trying to do too many things and like an add-on goal to not have to write any of my own custom code. So I just threw a bunch of things together. If I had done it right, I would have probably in the beginning just used LearnDash as payment gateways instead of WooCommerce, maybe with a different subscription plugin or a different membership recurring payment plugin at the time.

I want to stress that any of these tools, SaaS, or self-hosted can be overwhelming and you could choose the wrong one no matter what. So putting some thought into the beginning and finding good resources is important. I think the big benefit of going the self-hosted route like Jack mentioned earlier is if you do need something custom, it’s a lot easier on the self-hosted platform. So blending that ease of use with customization is like the sweet spot for a lot of creators.

Jack Kitterhing: Yeah, definitely. Because I think as well, in the SaaS world, you see people kind of sign up because they think it’s easier. But SaaS products can be so overwhelming too. Go and spin up any SaaS product today and see how many options they got. There’s so many options and it is kind of an option overload because everything’s built-in.

So that’s where WordPress is nice as well because WordPress is more modular. If you don’t necessarily need it, you don’t have to have it. No one’s forcing you to install 50 plugins. And no one says, Go and install 50 plugins. I see people and they install 100 plugins, and they’re like, “Do I need all this?” And it’s like, well, you’ve got five security plugins and six byte caching plugins. No, you definitely don’t need all those.

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Joe Casabona: To bring you back to LearnDash, I think you have right now one of the better onboarding or getting started experiences because you have the boot camp with videos embedded. Right?

Jack Kitterhing: Right.

Joe Casabona: Beautifully narrated by someone.

Jack Kitterhing: Perfectly done.

Joe Casabona: Yeah. I just wondered, were you done? Great videos. I think that is super helpful. I think that obviously there’s great value in that video learning aspect. I don’t know if Teachable has it but I do know that there are… I just set up like SparkLoop for an email referral and they have a pretty good onboarding process. But I would love to see that come down to like fewer steps.

Jack Kitterhing: Right. And I think that’s where we’re trying to go with LearnDash onboarding wizard. What we’re also trying to do is make sure that it’s powerful while still being simple. Like at the end of the onboarding wizard, we show you like… We’ve created 50 steps automatically. We’ve configured this, this and this option for you based on what you told us, but then it’s there. So if you have an issue that, you know, maybe you want to change a sentence before you finish it.

And then you obviously follow Chris on Twitter, you see my Twitter, so you may have seen me mention the new video creation tool. So the new course creation tool will basically allow you to drop a playlist URL into the tool and we will build your course for you. All you literally need is one URL, every video is pulled in, the description is passed, everything’s in there. And that’s going to be such a powerful way to get started in LearnDash. If you’re that small creator and you’ve got videos, one link, click one button, and you’re away and ready to go.

Joe Casabona: That’s really amazing, right? And I suspect you probably know this better than me but do you find that most of your creators are using unlisted YouTube videos for their courses?

Jack Kitterhing: Yeah. We see a lot of unlisted YouTube videos. And then we also see a lot of Vimeo. So you know, the tool will support multiple video players and most probably, in the end, just support any video file format. But give us a Dropbox link with some Mp4s and it, we’ll pull them in. We pull anything in. It’s a video, we can pull it in.

I remember when Chris asked me for this. He was like, “Can we do this?” And I’m like, “Yeah, I’m pretty sure we can do this. I don’t see any problem. I’m reasonably comfortable with doing this.” And I go to… Obviously, since the acquisition of Liquid Web is like hire more developers. We got a lot more development pals than we had.

And I go to one of our new developers, he’s been a friend of mine for a while and he was like, “Yeah, I can do this.” I was like, “Can you do it in two days? I really want to look at a prototype.” And he was like, that’s kind of quick.” I’m like, “I know, you can do it.” So on one of the Fridays, he just sends me this link and he’s like, “Yeah, try this out here.” I’m like, Perfect.” It’s just so amazing to see what he’s created so far.” I dropped a YouTube playlist URL, then I had a course with like 12 steps built-in like 60 seconds.

Joe Casabona: Gosh, that is amazing because I use Vimeo Pro, and that is by far the most time-consuming part. I mean, putting the course together, obviously. But when it comes to launching the course, that is by far the most time-consuming part is your course builder in LearnDash is already really good. You can kind of create everything there in one screen and then kind of click through to each one. But, man, just uploading a playlist. This is I think one of the great reasons why you should go with tools like LearnDash. Right?

Jack Kitterhing: Right.

Joe Casabona: Because of the flexibility, the ability to move fast, right? You want to serve the most amount of customers possible. But if you do have these kind of little niche needs, they can also be served probably more likely there than with Teachable or whatever.

Jack Kitterhing: Right. Exactly. And it’s kind of like appealing to everyone as well. I think a lot of people do create video courses now. I mean, personally, I’m like a writing person. I’m like a written down person. Every course I do is written down. And everyone’s like, “Why aren’t you doing video?” I’m like, “Well, as you can tell, I don’t have a good mic. I don’t have a good setup for doing video. I live in southeast London. There’s a lot of background noise quite often. It’s not really optimal to try and do video courses. So I write it down. But I love the fact that people will be able to get started so quickly.

Like so many people come to us at LearnDash and they want video. And to just be able to dive into that and have that as part of the wizard where it’s so easy to set up and do. Sometimes there’s questions like, you know, how do I create a lesson? What was the lesson in LearnDash? It’s like you don’t even have to worry about that because we do it for you. We’re assuming your video is a lesson. Add a price to it because the setup wizard you got Stripe Connect. You will be selling your course in, I don’t know, how fast your internet connection is. If your internet connection is pretty decent, you could be selling the course in five minutes.

Joe Casabona: The famous five-minute install, right?

Jack Kitterhing: Right, the famous five-minute install the LearnDash style.

Joe Casabona: Gosh, that’s so great. I love that. I think we’ve given the listeners some good takeaways. I think probably the most important thing to think about is your needs and how you can be best served. You want to look at cost and flexibility, understanding that your needs are going to grow too.

Jack Kitterhing: That’s a great point. Scalability, right?

Joe Casabona: Yeah.

Jack Kitterhing: Scalability with a SaaS versus a self-hosted solution. Like if you’ve got a WordPress site and you get a million hits, you know, you’re on Oprah, and then you’re like, “Oh, crap, what do I do?” Well, most managed WordPress hosts will serve that for you. They’ve got the capability to serve that content. They’ll figure out the billing with you later.

But if you’re on a SaaS, and then they’re like, “No, sorry, you hit limit. You need to upgrade your plan.” And it’s like, “Oh, I just lost, you know, $500,000 in sales because I need to upgrade my plan.” Whereas the WordPress hosting will just do that.

I think you can see even… I can’t remember the company now, but there was like a big brand on Shopify. They have problems with scalability because Shopify is fantastic and they got some of the best engineers in the world. But what you got to keep in mind is you’re always really on shared hosting with a SaaS. You’re always on shared hosting. You’re always sharing it with someone else.

A noisy neighbor like that in your in real-life can annoy you on the server. And you get that person that gets a ton of traffic or they get something happen to them. And that’s where owning your own platform really comes into its own on WordPress. You’ve got that flexibility to move it wherever. If you scare sudden spike, spin up a new server, route some traffic somewhere else, you can’t do that on a site. You can’t magically make headway on a SaaS like that.

Joe Casabona: Right. Right. And I mean even using YouTube or Vimeo, you have your videos there. And like granted you probably have the raw files. From what I understand, Teachable does the video hosting too, right?

Jack Kitterhing: Right, exactly.

Joe Casabona: What if I just want to share a video? What if I want to move services? Now I have to download and re-upload all those videos again?

I guess this is maybe the thesis that I’ll set when I do the intro for this episode. As a creator, it’s important to be flexible, right? If you just want to sell one course, and you know it’s just going to be one course, maybe Teachable is good for you. But if you want to build a business where you’re creating content where you’re building a community and working with students, I think you probably want a little bit more than just the ability to give access to videos by a single payment. Right?

Jack Kitterhing: Right. I think also it’s important as a business to own your own data. That’s what you get with WordPress. A WordPress site, even if the plugin itself doesn’t provide you a way to export, you’ve got WordPress’ exporters. There’s plugins that can export. You’ve got direct access to your database. You know, just download your database. You have all your data there. You own your data. You can do anything with it you want. You don’t always get that with SaaS.

I mean, technically, obviously you own the copyright to the course you upload, to what you create. But we’ve seen it before with SaaS in the past. Not necessarily in the LMS world, but other SaaSes where, you know, they lock down the person’s account because of whatever reason. You know, some old tweet gets resurface and that person gets canceled and then they cancel the account.

If you’ve got a WordPress site, you own it. It’s very rare for a host to cancel an account, basically is what I’m saying. I’ve never seen or had any customer in like 12 years say, “Oh, my host canceled my account because of this.” It’s always because of a SaaS.

Because what you get with SaaS is like… And this does happen in the LMS world. So you have a textbook back in high school in a class. Someone wrote that textbook like 20 years ago and then they file a copyright claim on the person because they use a small piece of that text in their course to make a point. There were quotes. But on some of these platforms, they will take your website down, they’ll take your costs down as they’re investigating.

And then you’ve got no other income stream. Like if that’s your income streams to pay your mortgage and your course gets taken down while they investigate for weeks, what do you do? But if you’re on WordPress, you’ve got the content. You’ve got the full access to everything. That’s why I think as a creator it’s super important to have your own access to your own content.

Joe Casabona: I guess that’s right. You’re taking on a little bit more risk, but you presumably understand the… I guess you’re not even taking on more risk, you’re taking on the same amount of risk. But now you have this middle entity that doesn’t want to take on the same liability that maybe you understand. Maybe that’s a way to put it.

Jack Kitterhing: I guess you could mitigate the risks. Because what the problem is, is obviously you get someone send in a copyright claim to a SaaS and they don’t want to be sued for $400 million from someone with a book. So they just take down your account. That’s the quickest way to resolve. They don’t want to go to you and say, “Oh, have you got permission for this? Can you prove the permission?” It’s too long-winded.

Whereas if you own it and you get that request, and you’re like, “Yeah, I didn’t actually get permission,” you can just delete off the website. Apologize, lay off the website, the content is removed, won’t do it again, sorry.” It’s probably not going to go any further. But you still got your content. Whereas SaaS, they never get to that point, because their lawyers internally are too worried about being sued to give you that opportunity.

Joe Casabona: And similarly, if somebody wants to sue Teachable for $400 million, they could probably get some fraction of that. If they’re suing me for $400 million, they’re not getting that. I don’t have that.

Jack Kitterhing: Right. Exactly. That’s the thing as well. I think some of these companies are more willing to go after a larger brand. Because they know like if they take Joe to court, they’re not going to get $400 million from you. But if they take Teachable to court, they can get some.

Joe Casabona: They’re going to get $500,000 from my insurance policy and then my premium is going to go up like 10 bucks a month or something like that. That’s what they’ll get from me. That’s a really good point. I think I really liked this episode because I don’t feel like we started at a very clear spot and then we ended in a really good spot. So thank you, listeners, for coming on this journey with us.

Before I ask Jack about his trade secret, I do want to say that we’ll talk briefly in Build Something More about cohort-based courses mostly but where online learning is going and where Jack sees LearnDash in that bigger picture. By the way, sign up over at howibuilt.it/261 if you want to become a member to hear that conversation. But Jack, I do need to ask you my favorite question, which is, do you have any trades secrets for us.

Jack Kitterhing: Oh, do I have any trade secrets? I guess my main trade secret is that I don’t. I guess the main trade secret is being in the game a long time and working in a lot of places. That’s my trade secret. Wearer of many hats. Learn as much as you can.

Joe Casabona: I like that. I like that. Put in the work, learn from people. That’s not a secret. That’s just something I think that people want to try to shortcut. Right?

Jack Kitterhing: Yeah. Put in the time and learn it. There’s so many great people. Especially if you’re getting started in the WordPress or creative space, there’s great communities out there that push people along and help out. And without the communities, you don’t grow right. I mean, the first website I built was frickin’ terrible. Absolute crap.

Joe Casabona: Blue background, gold text. That was my first website.

Jack Kitterhing: It’d be a marquee just rolling along the top.

Joe Casabona: We made websites at similar times. Awesome. Well, Jack, this has been a great conversation. If people want to learn more about you, where can they find you?

Jack Kitterhing: You can find me over on Twitter @codemonkey_jack. And you can also find me at Jak.dev, which is my sparsely used blog, though I do post every few weeks.

Joe Casabona: Jack.dev. Wow, nice work getting that.

Jack Kitterhing: That is jak.dev. Someone already stole my URL.

Joe Casabona: I feel that. I feel that. There’s somebody owns casabona.com and owned it like well before me. But the site was dormant for like 10 years. And like, every so often, I’d be like, “So can I buy this now?” And they’re like, “Nah.” And it’s back now and I was really bummed that I can’t have casabona.com.

Jack Kitterhing: I feel that.

Joe Casabona: Awesome. Well, I will link to all of that in the show notes over at howibuilt.it/261. Thanks so much to NitroPack and Nexcess for sponsoring this episode of How I Built It. If you want to hear Jack and I talk more about where online learning is going and where LearnDash sees itself, you can become a member of the Creator Crew. You’ll also get ad-free, extended episodes of all of the interviews that I do here on How I Built It. You can do that for as little as 50 bucks a year over at joincreatorcrew.com or again at the show notes page on howibuilt.it/261.

But that’s it for this episode. Thanks so much for listening. And Jack, thanks so much for your time. I really appreciate it.

Jack Kitterhing: Thanks a lot, Joe. I appreciate it too. It’s great being in.

Joe Casabona: To everybody out there listening, until next time, get out there and build something.