Q: If you had the opportunity to redo your membership site, what would you do differently?

From time to time, folks reach out to me with questions about how to build a successful membership site. Recently, I was asked, “If you had the opportunity to redo your membership site, what would you do differently?”

From time to time, folks reach out to me with questions about building a successful membership site. While I certainly don’t consider myself an expert, I’m more than happy to share some of the lessons I’ve learned the hard way while building WP101.com, my community for WordPress beginners. Here’s an example of one of those questions…

Q: If you had the opportunity to redo your membership site, what would you do differently?

For the most part, WP101 has been a “work in progress,” continually evolving since its launch in 2008. As a result, there are many things that I’ve learned the hard way… things I would have done differently if I were to launch the same site today.
1. Choose a robust membership plugin that will grow with your site.
I made the mistake of using a popular membership plugin that made use of obfuscated code, making it impossible to customize as my site matured. The same plugin also did not include support for one of the most popular payment gateways (Stripe), which created additional problems down the road (see below).
Eventually, I abandoned this plugin for a proprietary system that I customized heavily for WP101 — another route I strongly recommend you avoid.
If I were to build a new site like WP101 today, I would choose the excellent LifterLMS. It’s by far the best WordPress plugin for building an online learning site. You can sell courses, create quizzes, track student progress, and much more.
But what I love most about LifterLMS is the ability to create “engagements” — touch points with your students as they progress through a course. You send a personalized email when a student completes a particular lesson, for example. Or award them a badge or certificate of achievement when they complete an entire course. These engagements help restore the human element to online learning, something that is conspicuously absent from most online learning sites today.
Update: We recently migrated WP101.com to LifterLMS! You can read the blog announcement including all the details on how our move went!
But don’t stop with this single recommendation. There are dozens of membership plugins available to you today. My friend and mentor, Chris Lema, has created a beautiful infographic that will help you choose the best membership plugin for your needs, and has written a number of articles comparing WordPress membership plugins.
2. Choose a payment gateway that won’t lock you into your current membership plugin.
While PayPal is certainly the most popular payment gateway worldwide, carefully consider other options before committing to them. In addition to countless nightmarish stories of frozen accounts and suddenly disappearing funds, their support is among the worst in the business, driving many to the brink of insanity.
NOTE: My personal story, along with some technical jargon follows.
TL;DR: Avoid PayPal. Choose a membership plugin that supports Stripe, one of the most reputable and flexible payment gateways out there today.
Initially, I chose PayPal’s Website Payments Pro plan, which integrated nicely with my original membership plugin. What I didn’t realize at the time was that this choice would come back to haunt me down the road.
You see, whenever a recurring subscription is created in PayPal, there’s an important piece of data, called an IPN (Instant Payment Notification) URL, that is saved along with the subscriber’s payment details. Every time a subscription payment is processed, PayPal ‘pings’ the IPN associated with that subscription to let your membership plugin know that the payment was successful, and the subscriber’s account is still active.
The final step in this ‘handshake’ is that your membership plugin must confirm receipt of the IPN details. If PayPal does not receive this automatic confirmation of a successful Instant Payment Notification, they conclude that your account must be fraudulent… and subsequently revoke your ability to process future web payments. Yikes.
Each and every membership plugin creates their own IPN URL, which means if you should ever choose to migrate your site to a new membership plugin, all your existing subscriptions will contain an invalid IPN URL, which means future recurring payments will fail, putting you at risk of having your PayPal account shut down.
You cannot change IPN addresses for existing recurring subscriptions, which means you’ll have to cancel every one of your existing subscriptions, then politely ask all your subscribers to sign up again… a step that will absolutely cost you a number of subscribers, resulting in a loss of recurring revenue.
When I migrated away from our original membership plugin, I chose a 3rd party payment gateway (Spreedly) that specialized in recurring subscription payments. This service handled all the payment details on their own site, eliminating the need for secure sign up forms and SSL certificates on my own site, which I thought was a bonus.
Fast forward to today. We’re stuck again.
Spreedly has been sold to Pin Payments, giving me reason to believe the future of the entire gateway is uncertain. But now that all our members’ payment data is stored on their servers, I have no options for migrating to another membership platform. This particular gateway is far too small to be supported by any of the major membership plugins, so I’m stuck either continuing to use my hacked-together, proprietary membership solution together with this current payment gateway, or migrating to a new membership plugin, which could result in losing most — if not all — of our existing recurring revenue.
Moral of the story? Choose a reputable and flexible payment gateway that will enable you to change membership plugins down the road, should you so choose. If I were building WP101 today, I would use Stripe as my payment gateway, because of their stellar reputation, which is second to none, along with their powerful API and developer tools.
3. Start building your email list from day one!
Because our original membership plugin included the ability to email members directly from within the plugin’s own options panel, I didn’t feel we needed a 3rd party email newsletter service. I was wrong.
Now that we’ve changed membership plugins, I no longer have the ability to email our 15,000 members. My only option is to manually import 15,000 email addresses into a service like MailChimp, requiring every recipient to double opt-in once again, a hassle that will likely result in a significantly reduced audience.
Numerous studies have demonstrated the benefits of emailing your audience on a regular basis. It’s probably the best way to ensure you stay “top of mind” with your members, make yourself available for two-way conversations, and let them know about new products and services that will benefit them.
But beyond the ability to communicate with your current members, inviting new people to subscribe to your email newsletter list before joining your site is a great way to let them sample some of your content and get a sense of who you are. Folks will be more likely to join your membership site if you’ve already offered something of value up front.
MailChimp is a popular email newsletter service that lets you create multiple lists or categories of subscribers, enabling you to send strategic, focused emails to specific groups within your audience (see ‘segmentation’ below).
Then, use a plugin like OptinMonster to include an unobtrusive subscription form on your site that will enable folks to sign up for your email newsletter.
Finally, consider creating a series of pre-written emails that will be “dripped” automatically at pre-determined intervals, incrementally introducing yourself to new subscribers, while also providing valuable tips and insights up front that will add credibility to you and your offering.
4. Get to know your audience. Focus on segmentation from day one.
I’ve only recently begun to focus on this, but I wish I had understood the importance of this practice from day one, because now I have questions about how to better serve our members, and I realize that I can’t say with confidence who our members are.
How many of them are primarily bloggers? What percentage of loud members are wanting to learn how to build an e-commerce site? How many are professionals using WordPress to build a business site, versus amateurs who just enjoy writing blog posts in their spare time?
As you can see, these questions are critical in determining the type of content we create next, how we continue to serve our members in the best way possible, and even what we choose to charge for a membership to our site.
So, what is segmentationIn short, it’s getting to know your audience so you can speak to each member in the way that best connects with and serves them.
Practically, it means dividing your audience into groups based on geography, behavior, events or occasions, or other similarities that allow you to connect with them in the best way possible.
Look, nobody enjoys being mass-marketed.

“You want to go where everybody knows your name,
and they’re always glad you came.
You wanna be where you can see,
our troubles are all the same.”

You can’t afford to treat every person the same way, or communicate with every individual using the same, one-size-fits-all approach. No, you need to communicate with each person in the way that best connects with them, lets them know you understand their specific frustrations and needs, and that you can help them.
No matter how small your audience may be at first, you need to begin focusing on segmentation. Do you know who your whales, dolphins, and minnows are? Not all customers are created equal, and you need to know who you best serve from day one.
Read more from Chris Lema about segmentation.
5. Avoid the temptation to offer cheap or lifetime memberships.
When I launched WP101, I had no idea it would become as popular as it has. Because I thought too small, I initially offered a lifetime membership for just $19.
It was a “no-brainer” price point, which enabled us to build some early traction, but resulted in a tremendous loss of revenue over the years… revenue that would have enabled us to grow much quicker, and better serve our members today.
I knew nothing about the LTV (lifetime value) of a customer, so I didn’t fully realize that a one-time payment of $19 from a member would not enable me to continue creating new content or providing support for that member years down the road. Rather, those initial members eventually become a “drain” on your resources, and wind up costing you more money to support.
It’s a bit of a Ponzi scheme because you quickly become reliant on the income of new members to cover the cost of creating content and supporting your original customers, who are no longer paying you. And it never ends; you’re only able to stay afloat if you have a constant stream of new members, and you’re only as financially stable as your last month.
Today, we offer recurring subscriptions, which enables us to build on a constantly-growing base of revenue so that we can eventually afford to bring on new staff and other resources that will better serve our members for years to come.
Hey, I’m still learning, but hopefully some of these tips will help you avoid some of the pitfalls that I’ve encountered along the way! If so, these hard-learned lessons will all be worthwhile.
Got questions? Suggestions? Post them in the comments below. I look forward to the continued dialog!


Hi Shawn,
Your website wp101.com is great and our company has recommended it to our newbie wordPress clients .
I can’t agree with you more about stripe payment gateway as it’s necessary for increasing the conversion rate (btw, wishlist member does support stripe now)
I wanted to share with you, our online store that develop many plugins for Wishlist Member
We have some very unique plugins and I’m sure that every one that uses Wishlist Member to mange his membership site can benefit from them.
The Wishlist Member dedicated plugins category is located on:
Hope you will find these plugins helpful for you as well
~Bob Tolbert

Hi Shawn,
Great post. I very much appreciate the honesty. I find myself exactly where you were when you started – figuring out how to set up a membership site with the right combination of seemingly endless plug-ins, gateways, payment processors etc.
My reason to create a member subscription site and/or e-course segment of the site is to sell my knowledge, much like all of us I guess. My background is actually in product development. I invented a kitchen gadget and appeared on Dragons’ Den / Sharks Tank, didn’t make a deal and then still moved forward by securing an investor on the other side of the world. I naively thought that once I had the product produced, people would beat my door down wanting to buy it. The problem was two-fold:
1) I had to figure out how to get the product in front of people at a return of investment that financially made sense. I quickly learned that paying for advertising on Facebook, Google etc., didn’t make sense because the product only retailed for $10-$15. Paying 10% of that price for someone to click to my site (if I was lucky), coupled with a 1-3% conversion quickly taught me that I was spending more money on advertising than I was making on sales.
2) Much like you describe when you talked about selling a lifetime membership. My product is made from high quality stainless steel and is guaranteed forever. It’s not a consumable. That means that I must constantly find new customers. Not an easy task. I’ve just started blogging to bring attention to the product but as we all know, that is no way to instantly bring customers to any site. Then of course, they still have to buy the product so I have to deal with the endless variables that may be keeping them from converting (price, color, layout etc)
Back to my point – my journey has been full of successes and failures and has taught me concepts such as conceptualization, CAD, prototyping, intellectual property, mold production, manufacturing, graphic design, web design, package design, bar coding, importing, custom, scripting/shooting/editing and the list goes on and on and on. I’m hoping that there are other people that would be willing to pay for this knowledge in exchange for shaving years off of their project and tens of thousands of dollars. This now brings me to the most important issue you raised – segmentation. Particularly, are my readers/students going to be minnows, dolphins or whales?
You have given me lots to think about and I appreciate the time and information you put into this post.
Sasha Srdic

Hey Shawn,
Congrats on the migration to LifterLMS! So awesome!
How did you workaround the issue in problem two. Not sure how long ago this was written, but were you able to overcome the Paypal payment gateway problem. I would love to move to LifterLMS, but I’m not sure how to overcome the fact that I have all of these recurring payment subscriptions in Paypal. Alas, if I could go back in time I would choose another payment gateway. But, I have to believe there is some way to work around this. Everything is figureoutable, right?!
Would love to hear how you solved this without losing your current recurring revenue.
Thanks in advance.

Hi Jen,
Thanks for dropping by, and for your question.
The short answer is that I didn’t tackle that problem. I did speak with several developers and it can be done.
The process essentially involves creating a custom script that “spoofs” the PayPal IPN confirmation address on your site. The script simply echoes back a confirmation to PayPal that the payment was received. The same script also reports to the new system that the subscriber has renewed and is active.
The problem is that the subscriber is still technically on the old subscription, and will be indefinitely until/unless they cancel that subscription.
An alternative is to email all your subscribers and invite them to re-subscribe on your new system. That’s less than ideal, and you can imagine that most people won’t bother with the hassle.
SO… I opted to skip it altogether. We migrated all our current subscribers into the new system and grandfathered them into a complimentary Lifetime Membership.
At the same time, we changed our pricing model — offering courses in addition to the membership option.As a result, our monthly revenue only dropped about $500, and I anticipate we’ll quickly be even again.
That’s actually less than it would have cost me to pay to fix the problem using the above workaround.
In the end, I feel it was a better investment to give my members something of value that they weren’t expecting — or, as Michael Hyatt calls it, “creating a WOW experience.” That will translate into customer loyalty, and even more referrals.
In other words, I chose to take the monetary hit by re-investing it into my members, rather than paying roughly the same amount to a developer for a script that would have preserved our current MRR.
It was the right decision for us, but probably wouldn’t work for sites with even more members, or sites where the majority of revenue is from monthly recurring subscriptions.
One way or the other, it can be done. 🙂
Hope this helps!

Thanks for the detail in this post. One year after launch, these items just become so obvious it’s hard to believe they were initially overlooked.
IMO, the most obvious / un-obvious point in this that people will consistently underestimate is this :
4. Get to know your audience. Focus on segmentation from day one.
Technically, anybody can release a membership site, etc, etc – but what keeps the audience paying year after year? Relevant content and engagement!!!!!

Thanks for the article, Shawn. Did you consider LearnDash when choosing LifterLMS? I’m choosing between the two and wondered what made you go with LifterLMS. Thanks!

Hi Todd,
My good friend and business coach, Chris Lema, and I spent more than a year carefully reviewing and evaluating dozens of membership plugins (including LearnDash) that might serve WP101.
LifterLMS was the only plugin that included everything we needed in one plugin, without having to rely on 3rd-party integrations like BadgeOS to provide certificates and badges upon course completion, or outside mail services like MailChimp to provide simple email triggers as students proceed through a course.
It’s certainly not without its issues, but their support team has been stellar. And they release updates every week or so, so they’re continually updating the plugin.
Chris has written a comparison post of the top LMS plugins for WordPress:
Together, we decided that LifterLMS was best for WP101’s specific needs. Ultimately, it will come down to the features you need to support your specific audience.

Hi Shawn,
Your post says, “Today, we offer recurring subscriptions, which enables us to build on a constantly-growing base of revenue.” But when I visit: https://www.wp101.com/membership/ I see three “one-time” purchase options, but no recurring subscriptions.
I’m curious if I’m on the wrong page, if I’m missing something, or if you have gone back to a “one-time” sales model versus monthly fees, and if so, why?
Stacy Lynne

Thanks for your question, Stacy.
The short answer is that we have recently returned to a one-time payment model. Let’s chalk this one up to “never stop learning.” Here’s what I’ve discovered…
While all the points above are still perfectly valid — and I recommend you avoid lifetime memberships if at all possible — in the particular case of online education where the content is fairly basic, offering a lifetime membership can actually boost signups.
In the year since I published this article, we discovered that the majority of our students did not want to renew their membership. And why would they? Once you’ve watched our “WordPress 101” videos and learned the basics of WordPress, why would you continue paying a recurring annual fee to return and watch the same videos (albeit updated versions)?
When it comes to basic video tutorials, we found that offering a one-time purchase for lifetime access that enables you to return and watch the videos at any time actually boosted conversions.
Now, this is definitely not the case with membership sites, where you are continually offering new content on a monthly basis. That’s when you want to charge a recurring fee for continued access to member-only content.
You can also charge much more for advanced courses and content that you can’t find elsewhere.
But, if you’re only offering basic training content, and it costs you almost nothing for someone to return and watch the videos again, you might consider offering lifetime access for a one-time purchase. In that particular case, it can actually become a strong selling point.
Today, we offer three different plans: Basics (WordPress fundamentals only), Premium (all of our current courses), and Ultimate (all of our current — and future courses).
Rather than differentiating plans by time: Monthly/Annual/Lifetime, we’re differentiating by the amount of content: Basics/Current Library/Future Content
Hope this helps explain what we’re learning. We continue to learn as we go!