The Biggest Challenges of Building a Membership Website

Discover the biggest challenges of building a membership website—from retention to payment issues—and how to solve them before you launch.

Building a membership website can promise stability and community, but it also comes with significant hurdles. In this video, we dive deep into the biggest challenges you might face, from content management to member retention. Whether you’re just starting out or looking to improve an existing site, our insights will help you navigate these complexities. Don’t miss out — watch now to uncover essential strategies for a successful membership.

#1 – Churn is the real business, not signups

Most founders obsess over acquisition, but a membership lives or dies on retention. A 5% monthly churn rate means you replace your entire member base every 20 months just to stay flat.

#2 – The content treadmill never stops

Unlike a course you build once, a membership demands fresh value every single month. Founders routinely underestimate the ongoing production load and burn out around month six.

#3 – Community requires a host, not just a forum

An empty discussion board actively signals failure. Early-stage communities need daily seeding, prompting, and moderation from a real person until critical mass makes them self-sustaining.

#4 – Tech stack complexity compounds fast

Membership plugin, payment gateway, email automation, LMS, community tool, and access control all need to talk to each other. Each integration is a point of failure that costs support hours.

#5 – Onboarding decides the first 90 days

Members who don’t get a win in week one cancel by month three. A vague “welcome, explore everything” dashboard is one of the biggest silent killers of recurring revenue.

#6 – Pricing sets the ceiling on everything

Price too low and you attract high-maintenance members while starving your budget for content and support. Price is a positioning decision, not a math problem — and it’s painful to change later.

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Jetpack: LifterLMS

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The Show’s Main Transcript

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[00:00:17.040] – Jonathan Denwood

Welcome back, folks, to the Membership Machine Show. This is episode 182. In this episode, we’re going to be talking about the biggest challenges of building a membership website. It’s a great thing to do. I think it’s totally possible, but there are some challenges, and there are some things that, if you know at the early stage, I think you’re going to get— it’s going to be really helpful for you. Can hardly talk today. So it should be a great show. I’ve got my co-host; he’s got a bad foot, a leg. He’s looking at amputation. No, no, he’s not looking at that. But appreciate him still coming on the show. Got Kurt. Kurt, would you like to introduce yourself to the listeners and viewers?

[00:01:08.790] –

Yeah, sure thing. My name is Kurt von Ahnen. I own an agency called Mañana No Más, and we do some really great work with the good folks over at WP-Tonic as well.

[00:01:18.440] – Jonathan Denwood

Yep. And, um, love you to join us with your questions live. We try and do this show around 2 PM Pacific Standard or around 4 PM Central Time, um, every Thursday. Um, so if you can join us with your questions, we’re more than eager to answer them. Best way to join us. We push it on LinkedIn and YouTube. So subscribe to the channel, and you’ll be notified when we’re coming up. So where do you think we should start with this, Kurt?

[00:02:01.950] – Kurt von Ahnen

I think we should start with a cautionary statement for people that are just, you know, new to us or haven’t really listened to our messaging before. And that is, you know, as we talk about memberships and the Membership Machine Show, it is an active choice.

[00:02:16.070] – Speaker 4

It’s—

[00:02:16.310] – Kurt von Ahnen

I don’t really believe in this passive income, build it and never worry about it again. So I think a lot of what we’ll talk about today, for some people that have— may have- heard about the easy button or, you know, uh, the magic of funnels or something, um, it takes work. And so I think knowing that we’re going to talk about how to do the work and, and how to find success by doing the work, I think that’s like the primary message, diving in.

[00:02:41.360] – Speaker 4

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[00:04:00.280] – Jonathan Denwood

Yeah, so let’s go straight in and I’ve got my number 1, um, on my list is Churn is the real business, not signups. Well, I partly believe that, um, if you’re starting, um, your membership, um, journey, you know, you’ve got to get people signed up. You’ve got to get your first batch of students. That should be your You should get your website. I believe in WordPress. I believe in using WordPress with LifterLMS. Um, I think there’s other choices that are great, but I think for flexibility, for future-proofing, for controlling your intellectual property, having as much control over your business. Um, I think these are really important things and I think you get all this with WordPress and with LifterLMS. So, um, get that out the way and your job is to get the course, the first course set up. Um, get everything looking half decent, get a landing page with your offer, but then it’s really getting that first batch of students. That’s what your focus and getting your first 12 20 students is, you should be your total focus. That’s all. Yeah. And getting that first batch in and learning from them. But after that, I think what’s on this list as number 1, churn, is important because if you got over that first stage in your, in your first 50 to 100 students and You are in this kind of, this 299, 250, 299 space.

[00:05:56.840] – Jonathan Denwood

A lot of people really wanna ramp up the marketing, but they, what they’re not noticing is they’re getting a lot of churn. So they’ve got what is I call a leaky bucket. They’re pouring the water in, they’re putting a lot of effort to get new students, new members, new subscribers. But the bucket’s got holes in it and the water’s pouring out. What do you reckon, Kurt?

[00:06:21.690] – Kurt von Ahnen

The, the bucket with the holes in it is— it’s a great analogy, but it’s so correct. It’s, um, I can remember back when podcasting first started coming out, Jonathan, and people would say, oh, I’m gonna, you know, I’m gonna have a subscription podcast. You know, if I had 1,000 people that listened and they each gave me a dollar month, I’d make a, you know, I’d make $100,000. And they would do this crazy math thing in their head. And then of course, they’d launch a podcast and make nothing. A very similar thing happens with, you know, whether it’s online learning courses that you’re trying to sell or memberships. If you don’t have a, you know, it’s a WIFM, right? What’s in it for me, right? What’s in it for me? If you don’t fulfill that question to your users, like what’s in it for them, Um, if there’s no value that comes, like an ongoing value, that hole in the bucket thing just is, is present and you’ll continuously lose people. And if you listen to any kind of like real sales training, selling real estate, cars, um, you know, giant, you know, corporate sales, they’ll tell you over and over again that you will make more money selling to your existing client base than you will chasing new clients.

[00:07:36.970] – Kurt von Ahnen

And so if we take that same ideology and we apply it towards what we’re doing in membership and learning, then it makes sense that we need to really cater to the people we already have in our tribe more so than just necessarily trying to grow the tribe. Because if we don’t concentrate on who we have, we’re gonna continue to lose them at a high churn rate.

[00:07:57.480] – Jonathan Denwood

Yeah, you know, we do enough of show, me and Kirk, it’s— a much bigger show in audience. I’ve been doing it for almost 9 years. I can’t believe that. Um, and we had a really great guest on who’s a true SEO content, um, producer. It’s worked for a number of very large companies. Lias Loughreen with us. He’s just a great guy, does swear a bit. Uh, um, but, um, we had a great show and SEO and getting People, new students, the landscape has dramatically changed over the last couple years and it’s taken me a while to accept it and I blamed myself probably too much, but I just got to accept that landscape has changed and you’ve got to accept that. But there are opportunities using video, going on Facebook groups, engaging with people, go using short-form video. It’s really possible to attract. You’ve got, in my opinion, it’s gotta be a niche subject or it’s gotta be a, if it’s a subject where people have to get training every year, that’s a great business model ’cause you’ve got a captive audience that has to get receive training. But if you, if you’re not in one of those, you, in my opinion, you’ve got to be in a niche.

[00:09:33.180] – Jonathan Denwood

Um, that niche can be really part of a, of a very broad subject like health, but if it’s just general health, yeah, yeah, unless you’re a big personality, ain’t gonna work out. Um, on to the next one. Content treadmill never stops.

[00:09:51.730] – Kurt von Ahnen

No.

[00:09:53.010] – Jonathan Denwood

Well, it doesn’t because you, if you want the business to grow, you’re gonna be after, which is linked to what I’ve just said. You’ve gotta be producing video content for social media, driving them to your website. Blogs are still gonna be important, but they’re gonna be more important for large language models like ChatGPT or Perplexity or, or, or any of the leading large learning models. You’re gonna get less traffic, but the good news is that if you’re, if you attract, if, if you are in a niche and you’re doing this work and they’re finding you through these large language models, they, that traffic should be much more focused to actually buying something from you. It should, if you’re doing the job right, that traffic, which is less than a few years ago if you were using blogging on, but it should be ready to buy much more than a couple years ago. Would you agree with that, Kurt?

[00:11:12.220] – Kurt von Ahnen

I do, but I want to phrase things in a way that maybe resonates with, with some of the audience that maybe wouldn’t be focused on like SEO or how Google feels this month. Like, if you think about the— when we talk about the content treadmill that never stops, think about a YouTube channel that you probably visit that has tons of videos. Like, for instance, I’ve got like 1,300 videos in a YouTube YouTube channel, uh, out of those 1,300 videos, how many of which ones get seen this week? Well, more than likely the ones I put out this week or last week. Nobody cares about the videos I put out 5 or 6 years ago except for me when I’m showing them off to friends. Um, it’s the same when people come to your product. So like when you go— like when you go to watch a series on TV, you go to watch Landman, for example, Um, not many people are— that have seen Landman before are going to sign up and rewatch season 1. They’re going to want to go to the latest season, the latest episode. And it’s the same with your product.

[00:12:15.940] – Kurt von Ahnen

Your product needs to consistently have new content to keep current people and new people attracted to coming to your site, which is your product.

[00:12:25.390] – Jonathan Denwood

Yeah, yeah, I see where you’re coming from. I think you You know, it depends on the subject. I think looking at YouTube channel, I think what I, the mistake I’ve made, and I think Kirk would say in all fairness he’s made it, and I think is I, I have given a lot of very confusing messages to YouTube. Um, I think choosing one subject, one niche, and staying in line and just having your channel about that subject, that niche, will give you the biggest chance to get some traffic. It depends what, what your niche is. You’re not going to get hundreds of thousands of people signing up. You could do, depending on the niche and how you come across. But, um, not going off subject, finding your niche. Finding your voice and sticking with it is crucial. And I think it’s the same with the other video social platforms like Instagram, TikTok, LinkedIn. Depends if you’re selling to consumer or to business. It’s finding a niche and keeping on subject really. Onto the next thing. Community requires a host. Not just a forum. What would you say about this one, Kurt?

[00:13:58.070] – Kurt von Ahnen

I don’t think this could be more clear because I have helped so many people launch, you know, community and course sites. Again, I go back to that build it and they will come and, and that passive income idea. It’s an active sport. And if you’re not active in your sport, you’re not going to find success. People sense that. I used to say it was like, you know, back in the ’80s I would go to dance clubs, believe it or not, and, um, you could always tell when you went to a club that sucked. Like, you’d get there, nobody’s dancing, the music sounds all right, but no one’s really— there’s no energy in the place. Like, a dead website can feel like that. Like, the club might have been great, might have been a great club, but if you went at the wrong time before everybody showed up and started dancing and it just didn’t look like fun you left. And that’s what your users will do if they get to your website and you’re not participating, you’re not moderating, you’re not liking, sharing, following, you know, patting people on the back, giving out affirmations. If you’re not interacting within your own product, you know, at that level, it’s very difficult to expect the users to interact at that level.

[00:15:09.380] – Kurt von Ahnen

And then it kind of dies on the vine.

[00:15:11.870] – Jonathan Denwood

Yeah, I think Building community, building community with a Facebook group initially, but I think WordPress has some great community products. I think one of the best is Fluent Community. There’s some SaaS products out there, but I think Fluent Community is just fantastic. And I don’t like Skool, I’ve made it clear. I don’t like the founders, I don’t like the messaging. I don’t like the baggage that comes with it, but they’ve been highly successful. But I think with WordPress Fluent Community and with LifterLMS, you’ve got tremendously powerful platform. But I think, um, you don’t have to build a community initially. I think starting off with a course is the best way to start, but after you’ve got your initial course out and you might use that as a lead magnet, a low-price paid lead magnet, and you build your next course. That’s when you might look at actually adding community because it will help with churn. It will help with stickiness if it’s run the right way. Um, you, it will mean that members will stay around longer. Until the next course comes out, the whole thing becomes much more valuable to people. Would you agree with what I’ve just outlined?

[00:16:45.280] – Kurt von Ahnen

I do. I do.

[00:16:46.810] – Speaker 1

I—

[00:16:47.510] – Kurt von Ahnen

there’s so much value in this. I really hope that people are kind of paying attention to the messages, like in between the lines, because I think if I’m just going to be blunt, Jonathan, we could talk about this for hours and we’ve given ourselves a, you know, a succinct amount of time to really discuss it. There’s a lot of in-between the lines.

[00:17:07.250] – Speaker 1

It—

[00:17:07.980] – Kurt von Ahnen

when I say it’s an active sport and then Jonathan expounds on that, I just, I can’t express enough with enough enthusiasm that it really takes a lot. So I’m really big on like teamwork, and I’m sure that this, this will come up in our conversation as we go, but if you’re not the social person, like you’re the tech person, be tech, but have someone on your team that is social. Have someone like don’t be afraid to split up the work.

[00:17:34.320] – Speaker 1

It—

[00:17:34.800] – Kurt von Ahnen

this doesn’t have to be a one-person sport. Like, you can have a team, and, um, I really advise that whenever possible. I, I have a new project our agency’s launched a couple weeks ago. We did another relaunch this week with an email blast, and they’ve got like an advisory committee on this deal that, that is— everyone’s like working within their strength, and you can really tell that this project has life compared to some other projects I’ve helped launch where it’s just one person trying to figure it out as they go. And that’s, that’s a very difficult road to hoe.

[00:18:07.470] – Jonathan Denwood

That’s fantastic. Well, I think it’s a good place for us to have our mid-break. I hope we’ve given you some insights about what you should be concentrating on. We’ve got a ton of experience in this area. We will be back In a few moments, folks.

[00:18:25.290] – Speaker 4

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[00:19:01.100] – Speaker 1

This podcast episode is brought to you by LifterLMS, the leading learning management system solution for WordPress. If you or your client are creating any kind of online course training-based membership website, or any type of e-learning project, LifterLMS is the most secure, stable, well-supported solution on the market. Go to lifterlms.com and save 20% at checkout with coupon code PODCAST20. That’s PODCAST20. Enjoy the rest of your show.

[00:19:40.220] – Jonathan Denwood

I’m coming back, folks. Well, we are coming back. Um, wanna point out, I do a great free newsletter. It’s normally about one of the subjects we, we’ve discussed in the podcast, but I add extra value with extra content that I’ve found and I write, I set it all up myself. It’s totally free. Love for you to sign up for it. Go over to wp-tonic.com/newsletter, wp-tonic. Wp-tonic.com/newsletter. Normally publish the newsletter every Tuesday, Tuesday or Wednesday. And like I say, I set it up all myself. So let’s go straight into it. The next point, tech stack complexity compounds fast. Yeah, people get a bit fixated, especially with WordPress, because I think I think it attracts people that do understand they want maximum control. They want maximum control over their intellectual property, and they’ve learned, or instinctively, they want the, the much, the most control possible. But then they tend to get a bit fixated about the tech stack. Um, you just want a strong tech stack that can expand with your business, basically, that you won’t find that you get to a certain size, you’ve got to jump ship, because totally doable, but it’s not something that you probably want to do.

[00:21:25.460] – Jonathan Denwood

So it’s best to find something that you can expand with Um, and with a lot of other systems, um, they’re very good at hiding the restriction points, as I call them, the problem points. You really got to do a really deep dive to compare one with the other to work out where the restriction points are, as I call it. With WordPress, you don’t have a restriction point because there’s always— it doesn’t exist. It’s, it’s totally expandable. So what’s your thoughts about this, Curt?

[00:22:06.890] – Kurt von Ahnen

Well, like yourself, I’m a fan of WordPress because of the flexibility, the ability to customize and the scalability of it. So there’s so many reasons why I’m in the WordPress court, right? Why I’m like that. But what I wanted to pound home on in this topic was, you know, you had mentioned the tech stack complexity compounds fast. And this might be a little contrarian because I’m, you know, I’m a developer, not a developer, I’m an agency in the space. I am a complete advocate for out of the box. Like I’m all about, let’s just keep this thing simple. Let’s limit the tools. You want to have courses? Let’s use this tool. You want to have a community? Let’s consider integrating this tool. You want to have a CRM? Let’s consider doing this. But when people are like, well, I want to integrate this with this, with that, with the other, and have this automation happen, and I want to use these other tools, it’s like, slow down, because you don’t— you haven’t built something that requires that yet. And it’s the, the, the simpler you can keep this thing as you build it and as you launch it and as you initially begin to grow it, the happier you’re gonna be.

[00:23:18.050] – Kurt von Ahnen

Because as we explained in the first couple of points, you’re already gonna have to be, you know, making content and communicating with people and doing— there’s energy for that. The last thing you wanna do is build something so complex that you’re constantly chasing updates or glitches or automations that don’t work. If you don’t need those things, just hold off on them until you do. If you’re in WordPress, you can always add those features as you go. You don’t have to rebuild the whole thing because you want to add a feature. You can just add the feature later.

[00:23:49.690] – Jonathan Denwood

Yeah, totally right. Onto the next one. Onboarding decides the first 90 days. Nothing more could be more truthful. A lot of people, you know, the first course, it’s totally understandable, but it’s the onboarding experience is important. What’s your thoughts about this, Kurt?

[00:24:11.310] – Kurt von Ahnen

My point about onboarding is whatever you thought was onboarding, you probably didn’t think it enough. Um, that’s, that’s what I’m thinking. Um, I can give you a real-life example. Um, I just did a project in higher education. The people that are coming to this product are incredibly intelligent. We have a CRM tool and, and some email automations that help onboard people, or what we think is onboarding. So congratulations, set your password. Here’s how you get to your course. Take a look at this tutorial video. Boom. And yet we’re still getting like support requests, emails saying they didn’t receive something or they didn’t get something or they weren’t aware how to reset their password. And what we have to remember, you know, working in the space, whether, whether you’re an agency or you’re, you know, a client that’s working with an agency or you’re someone that is a DIY, built your own website, you already know more about the platform and how it works than one of your customers, students, or, you know, tribe could possibly know. And so we make a lot of assumptions about how easy it would be to use the website as an end user.

[00:25:23.320] – Kurt von Ahnen

But unfortunately, what we interpret as being ease of use doesn’t translate to a lot of users. So in this one instance with this Higher Learning thing, I had to make a recollection that they might be really intelligent people and they might be a higher learning audience, but they might not have, might not have an e-learning experience that they can associate with. And so they don’t really understand the process of signing up for an account and a password and getting access to their course. And as simple as that sounds to me and Jonathan having a conversation, it’s different for them. So we have to elevate the onboarding to fill the gaps for the user not what we interpret as the gaps for the user, which are two different things.

[00:26:06.930] – Jonathan Denwood

Yeah, totally agree. The last one, the most difficult: pricing sets the ceiling on everything. I wouldn’t, I wouldn’t get hung up about this with your first course, your first course. And if you, if you’ve been with us and you’ve been listening to some of these shows, And I want to point out, we love to hear from you. Um, we, we love you to join us with your questions, and we will answer them during the show. So if you can join us at 5 PM Eastern Time, 4 PM Central, or 2 PM Pacific, um, like I say, it’s best to go to the WP-Tonic YouTube channel and subscribe Subscribe and you’ll be notified and join us with your questions, or just if you’re on Facebook or LinkedIn, we push it there as well. But we love you to join us with your questions. But pricing, I wouldn’t get hung up with it for your initial course, but after that, it really is important. What’s, what’s your views about this, Kurt?

[00:27:21.780] – Kurt von Ahnen

I hear what you say when you say it’s not as important on the first course, but then we have to remember that some people might only have a one-and-done project, like one course project.

[00:27:30.260] – Jonathan Denwood

Yeah, so then it is important.

[00:27:32.380] – Kurt von Ahnen

So then it is important, right? So, so like there’s— because we have a launch strategy that we discuss on the Membership Machine Show that’s like, come out with a small course, don’t make War and Peace, right? Come up with something small and then, you know, up your game.

[00:27:45.910] – Jonathan Denwood

Right?

[00:27:46.470] – Kurt von Ahnen

Improve things, up your game. And so we talk about the stair-step method to building success and selling higher-cost packages. But I will share with you: pricing absolutely is everything.

[00:27:59.700] – Jonathan Denwood

Yeah.

[00:28:00.100] – Kurt von Ahnen

Um, the project I’ve been talking about this whole show, we, we just last night took the pricing from $495 a course to $795 a course. And that sounds crazy because it’s a new launch. But the feedback we’ve gotten already—because it’s very important to get feedback from your users—that feedback said the price was too low, and we’re associated with colleges, and colleges aren’t giving away training, so we have to charge a fee commensurate with higher education. So that made sense. Uh, I launched a project called the Power Sport Academy years ago, and when I first launched it, I thought —well, and I did the math as we talked about earlier in the show—if I got 200 dealers to sign up and I sold for this much. And I thought I could sell this training for $1,500. And so I offered it for $1,500, and nobody bought. Only about a year later, after getting feedback from potential users, did I find out they all thought it was too cheap. They would never write a check for training that cheap in that industry. It had to be at least $10,000 or $12,000.

[00:29:00.710] – Kurt von Ahnen

So we raised the price to $12,000 and started selling enrollments. It sounds crazy, like I was willing to do it for $1,500, but I had to sell it for $12,000 before people saw value in it. So we have to remember —and this could—we could do a whole show on pricing —but there’s a thing called price anchoring, discounting, and value sales. And, um, if you were to listen to Grant Cardone, for example, he likes the— he likes the phrase 10x. So your pricing should be: will someone get a 10x a 10x value back from paying for your course? So if you sold your course for $100, would they be able to take that training and make $1,000 with it? If so, $100 is justified.

[00:29:42.230] – Jonathan Denwood

Yeah, we probably do. It’s a good subject. We probably do that next week then, shall we? Pricing. Final thoughts. Let’s wrap it up. We kept it to about half an hour, but I think we covered a lot of territory. I’ve tried to up the show notes a bit as well. What are your final thoughts on what we’ve covered? I think we’ve covered some good stuff today.

[00:30:09.910] – Kurt von Ahnen

My final thought is you must have gotten me excited today, Jonathan, because I think I’ve talked more today than I usually do. I like this topic. This is a really good topic to get people to, because people are passionate about what they want to share. We have to make that recognition: no matter how crazy the topic might sound to one person or another, for the person who has the idea, they’re passionate about whatever it is they want to share. And from our experience, we know there are certain pathways to success. And it’s, it’s, it’s exciting if you can put somebody with passion and energy and ability into a position with the tools required to find success, and you help them find that success; that’s just super exciting. And for people that think, well, they saw some famous guy say that courses were dead or some famous guy said memberships are dead, or, you know, don’t listen to that hype because this stuff goes in cycles. I just saw a thing last month that said the pathway to success was publishing your own book. And that blew my mind because that was the big thing 4 years ago.

[00:31:18.790] – Kurt von Ahnen

So just remember, all of these things come around in circles. And if this is what you’re driven to do, there is a pathway to success. You just need to architect it. And someone like Jonathan or myself or listening to the show is a great first step in putting that plan together.

[00:31:35.860] – Jonathan Denwood

Yeah. So we’re going to wrap it up now, folks. Like I say, join us next week. If you’ve got any questions, we’d love you to join us live and ask those questions during the show, and we will answer them. Either during the show or at the end. And we’ll see you next week, folks. Thanks a lot. Bye.

[00:31:54.770] – Speaker 1

Thanks for listening to the Membership Machine Show. Subscribe so you don’t miss future episodes, and leave a rating to support the show. Until next time.

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