Membership Site Challenges, Engagement and Retention: How to Earn Online Income (This is Better Than Drip Content)

As usual, most people are hung up because they're focusing on the wrong things and asking the wrong questions when trying to get their membership sites online and making money.

A big focus problem: stressing out about retention (keeping payment members in your site) when you should "set it and forget it" and focus all your energies on getting new people in the door.

Look, you don't need to drip out videos in tiny pieces, run a call center, or offer trials or discounts to get people to rejoin. Here's what you'll use to get people to join your sites, take action, and complete that course you offer:

  • Auto-subscribe everyone who buys into your membership site into an email autoresponder sublist with a follow-up email sequence
  • Match up your follow-up sequence to either your drip content, or just schedule your emails at a REASONABLE PACE for someone to not just consume the content, but take action
  • Important: don't send JUST ONE email per post... send at least 2-3 emails almost HOUNDING people over time to watch this video, make sure you watch this video, did you watch this video (this is the big one)

Just set those three things up and forget all about it. That alone will double your membership site retention whether it's monthly forever, a fixed term payment plan or even a single payment site – yes, I still follow-up with single payment buyers to make sure they take action.

Now, a reactivation page. Create a folder in your site called "invite" – such as, "" – this is the folder where you will store your reactivation pages.

Let's say Ray Edwards is a member of Webinar Crusher, and it's a 5 month program ($497 upfront or 5 payments of $99.95 spaced 31 days apart). He makes three payments and then cancels.

Don't jump to conclusions! The number 1 reason people cancel from our membership sites is due to credit card expiration... the average credit card only lasts 3 years and some even expire after 1 year! (Plus, for a long time, PayPal had a bug where, if someone updates with credit card information, it would CANCEL all recurring subscriptions!)

Ray has made three payments, and has two left, so we create a new payment button for two payments of $99.95 spaced 31 days apart, name the file "REdwards.html" (short for Ray Edwards). Add this as the headline, "Webinar Crusher: Reactivation Button." Add this as the subheadline: "For Ray Edwards Only!"

For the sub-sub-headline: "This Link Will Be Removed On (Deadline 7 Days From Now, i.e. January 1, 2015)." Add this as the text, "After clicking the reactivation payment button below, do NOT re-register. Instead, check out and then click the -- Existing members, login here – link." Then the button re-activate.

That's it! Adding that button, and nothing else, gets 50% of our drop-outs to sign back up into our membership sites. No bribe or incentive to rejoin, no discount or trial, no special video or gift... just the button to sign up and pay off the remaining payments and that's it!

Now, can I share my BEST strategy for taking membership retention through the roof? Hint: this is the same technique we've used in sites like Membership Cube where we had an 89% success rate (in an industry where even 10 or 20 percent is good) and the average person in our class setup three membership websites.

It's called: membership site challenges. It happens in three parts...

  • Part #1: You explain and show your module in a 60-90 minute video session
  • Part #2: Tell them at the end of that session (video in a blog post) to fill in the challenge or assignment (but don't call it "homework") – a very quick task, for example, create a 3-minute video and publish it online
  • Part #3: Ask four questions to get people to micro-commit to performing that task, including a deadline – they post a comment answering the four questions
  • Part #4: They go out and do the small assignment they were supposed to do, then come back and post "I AM DONE!" as a comment.

For example, let's say that Webinar Crusher is a 4-module course (it is). In the first module, we show you how to plan and promote a 20-minute webinar to a live audience. It's one thing to talk about it, another thing to show it, yet another thing for US to do it, but then we want YOU to do it too!

At the end of that video (it's a live paid webinar session but we record it) we send you over to that challenge within the membership site. It's just a blog post that says something like this...

Answer the following questions:

  1. What is the title of your webinar?
  2. What product will you review?
  3. Where will you post your recording?
  4. What time and date will your 20-minute webinar be?

When you are finished, come back and type "I AM DONE" in the comments.

Here's the formula for "challenge" posts...

  • The first is usually the NAME of some kind, as in, what's the name of the video you'll create or the product you'll create.
  • The second question is some sort of minor detail, such as the product you're reviewing or how long the video you're about to record will be
  • The third question is a proof element, usually where your completed task will end up online
  • The fourth and final question (don't ask more than four) is the exact time and date you'll finish and be completely done and online

This works WAY WAY better than a quiz or a "pay as you go" course.

You post this, you COMMAND people to fill in the challenge, right there in the video and during your live training, you fill this challenge in yourself.

Have a membership site, and run these challenges, build in some complementary software, systems, tools, and templates... email on a sequence several times per week when there are new posts and challenges... and now you don't have to worry about drip content or all these "crazy tricks" to hide from your buyers or fool them into paying you money.

Is this something you are ALREADY using, or WILL be using in your membership site?

Filed in: Archive 1: 2012-2016Membership SitesSocial Marketing

Comments (39)

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  1. Howard says:

    Robert you are correct about the challenges. They have helped me to actually apply the info you teach.

  2. Trevor Baret says:

    Robert – great information as usual.

    In a couple of your membership courses, your challenges have been the very thing which have kept me interested and moving forward.

    The fact that I am being challenged is the first thing – never back away from a challenge

    The fact that your challenges are so well planned and give actual guidance to what to do next is the next very important thing – as the member goes through the challenges, they are shown how to get from start to finish in clear steps, and in a much shorter time that they might otherwise have thought possible.

    You guys have really got the system sorted out…


  3. Cmarten says:

    These challenge posts seem to play into this new method of retention that seems all the rage these days: gamification. You make it more interactive and more fun for the subscribers, they’re more likely to stick around and keep making you money.

    I’m at the beginning of my membership site plans, and your information about retention is definitely helpful. Thanks!

  4. Marcia says:

    Very interesting content – as always. Of course you should keep posting to the blog.

    You are one of the few marketers I stay subscribed to.

    Thanks for all the effort you put into helping others.

  5. Hi Robert. Great insights and perspectives. i particularly like the following:

    Here’s the formula for “challenge” posts…

    The first is usually the NAME of some kind, as in, what’s the name of the video you’ll create or the product you’ll create.
    The second question is some sort of minor detail, such as the product you’re reviewing or how long the video you’re about to record will be
    The third question is a proof element, usually where your completed task will end up online
    The fourth and final question (don’t ask more than four) is the exact time and date you’ll finish and be completely done and online.

    I am looking forward to the creation of several membership sites; it starts with the next one after our Product University event in Salt Lake in June!

  6. Donna says:

    Hi Robert,

    Excellent post as usual, love your solution to Paypal’s awful glitch that has caused many problems over the years with credit card expirations! Argh! Your solution is very simple and solves the problem. 🙂

    Also like your retention solutions. The only thing I disagree with is the bombardment emails asking people to go do this or go watch that… only personally, I find them annoying, but apparently for the majority it works well for you.

    Thanks again for the value you add to your blog posts, makes me keep coming back to learn.

    Have a great day!

  7. Robert Plank says:

    About the so-called daily bombardment of emails…

    1. I want to make extra sure people check out the things they paid for, they need lots of reminders.

    2. If Warren Buffett “bombarded” me every day with a tip on how to make $5000 in 5 minutes he can bombard away.

    3. Let’s be honest, the average person is on hundreds of lists. They’re already getting overloaded every day, our job is to be heard amongst all the noise.

  8. Robin says:

    Robert, a great blog post. Thanks for sharing what I consider really pertinent information about retaining memebers in a membership site. Thanks.

  9. Lynn says:

    Like Marcia, you are one of the IMers I stay subscribed to (and have for quite a few years now). Thanks for the info on how to “walk them through” the tasks with a challenge, and especially how to set up a renew without hassle (theirs or mine) page. You and Lance could proudly wear “I am loved” buttons 😉

  10. Kate says:

    Hi Robert,

    This was really a new strategy for me. I think it’s really good for a “how to do…” membership site. Maybe not so for a PLR membership site, but certainly worth trying. I love the expired credit card tip too. Great way to recover. Thanks, Kater

  11. Excellent post, as usual. I’ve been guilty of lurking, but have always valued your posts.

  12. Will Horton says:

    Great post and usefull I will have my new site up this week and will add membership site to it, or maybe I will create a new separate site for each membership.
    Will Horton

  13. Hi Robert,

    There’s some interesting content in this post. I think I’m a fair way away from building a membership site yet, but when I do I shall certainly be taking on board your points here.

    I especially like the ‘challenge’ approach. It’s one thing to present information and training to people, but to give them a task to complete helps them to approach things with a whole different mindset. I think this is a good approach for a membership site because it helps the student to have a structure and a specific goal to attain which can help them have a sense of accomplishment and a drive to move on to the next task.


  14. Eileen says:

    This is amazing advice. Step-by-step! Awesome! Keep up the excellent posts!

  15. Gary B says:

    Very timely I’m just getting started with an organic gardening/landscape site. Some of the site will be open to a free membership but the part that gives them the step by step approach will be a paid section of the site. This info will save me a lot of trial and error research. Thank you so much

  16. Nancy says:

    Hmmmm. As I was reading this, I had it in mind how to put all the content into the autoresponder for lessons, and then just have something like a monthly Q&A call.

    But now, you’ve given me more ideas about how to set it up.

    And now I’m wondering how much to offer for free up front and how much to put inside the paid membership. There is a LOT of general info I can give on the topic I’m working on, but the real “juice” is going into the paid lessons.

    My question to you: Do you have a formula for where to draw the line between paid and free info? I know you have step-by-step outlines for almost everything so it would make sense that you’d have one for this too. Thought I’d ask and find out!

    Thank you so much for your consistent high quality content Robert!

  17. Pete Bass says:

    This was a very a very good post. Thanks for the great insights. Now if I just had some kind of an idea of what I could do a membership site about.

  18. These posts are something that I actually look forward to. It is not a chore to go through my mail when I get to read a post like the one I just read. I have ideas and as Gru sometimes says “light bulb” then most of the time when I check through the posts I find an explanation of the idea. “Amazing”. I sometimes fall behind in my plans but I just visit the site/s for the assorted programs and I am regenerated. Off to the races as you might say.

  19. Dale Powell says:

    I definitely have gone through some ups and downs about how I want to price my Membership site. While my content is important to people who want to maintain their computers, I feel some people will quickly get bored of the type of info I’m promoting, and won’t stick with it. We’ll see soon because I’m very close to launching it. Anyway, I decided to go with an annual fixed term price which should be more than enough time to learn the info, but I also thought I would include an option for a lifetime membership for a slightly higher one-time price.

    It’s great to hear everybody’s though process in these comments as well as Robert’s training so I don’t get overwhelmed.

  20. Thoroughly enjoyed reading this post and will be referring to the tips you’ve shared, Robert. I’m currently working on what I’d like my membership site to look like as a 3-tier membership, and these suggestions will be very helpful.

    Thank you.

  21. Karl Dallas says:

    I find your postings fascinating but not relevant to my work as a writer moving into ebook publishing.
    I have been trying to adapt your ideas to my work eg offer specimen chapter to people who sign up, conduct survey on what subjects people are interested in etc.
    Also – I’m not unique in this but it is common to most writers – I’m more or less penniless until one of my literary projects pays off.
    What can you offer people like me?

  22. Laurie Mills says:

    That’s a scary email title, lol.
    Where would we get the correct information that we need if you stop your blog posts?
    The next question should be, what are you going to do with your spare time?
    Answer; Create more useful items that we all need, maybe.

    You have so much insight into Internet Marketing and required procedures that you pass on freely to us, we would probably get lost in the wilderness again.

    This is tongue in cheek, behave or I will tell your Mother, lol.
    Regards, Laurie.

    P.S. Another excellent post, the PayPal hint is a bottler, and I must say I have been caught out myself by forgetting to update my own account.

  23. Hey Robert,

    Those are some great tips and I’ve been watching them at work in your sites. Interesting too that one of the questions I ask as I’m beginning to promote some of my own membership sites is what can I do or add to give more value and also be heard above the noise? There is a ton of competition for our short little spans of attention out there these days. Thanks for sharing I know many of your tips have already made a big difference for me and my business.

  24. Pat says:

    I found that one of the best parts of your programs are the Challenges sections. It seems to be key for engagement and retention.

  25. TMerksi says:

    Interesting to read your recommendation to send out 3 emails for every lesson you have in your course, or part of the project. This doesn’t annoy people? I’m always afraid that they’ll think I’m spamming them with “hey remember me” mails and unsubscribe.

  26. Funny thing about the “bombardment with email.”

    When I like the marketer who is “bombarding” me with good information, tips, reminders, whatever, I don’t feel bombarded or annoyed at all.

    It’s only the marketers I don’t like who send me a lot of emails that bother me. And if I really get nothing from their emails, I simply unsubscribe.

    So I agree with your philosophy that it’s better to risk sending too many emails then let people forget who you are by sending too few.

    Including challenges in your courses is a great idea. It has helped me sell my latest course and it is a big reason that I buy yours.

  27. hakim says:

    I really loved your post, Robert.

    It is indeed very challenging to manage a membership website, specially if you have a very big site.

    But with prope tactics, you can successfully run a membership site.

  28. baka says:

    I loved those “challenge” questions you have posted, I would love to use those questions if I open a membership website.

    I have joined various membership websites before, and many times I had to cancel my memberships due to various reasons.

    All I can say is, you have mentioned some very good tips in order to retain members.

  29. radioguy999 says:

    Very good article, as usual you are giving us some very good information.

    I may open a membership website in around 2 years and I have learned so much from this article. I now know what tactics I need to use, in order to retain members for my umcoming membership website.

  30. milkman says:

    This article is very easy to understand, thanks Robert.

    I did not know many members cancel their memberships because of credit card expirations. This is definitely something new for me.

    Membership retention can be a very challenging thing, there is no doubt.

  31. vusi says:

    A membership website owner’s income heavily depends on membership retentions.

    Once you get a member, you have to retain the member to turn him/her into a loyal member.

    I loved your article, Robert. It has taught me a thing or two.

  32. Excellent way of describing, and good paragraph
    to get information on the topic of my presentation subject matter,
    which i am going to present in institution of higher education.

  33. Smitty says:

    Wow. I really like your idea about that quasi-interactive membership challenge. What a great way to engage the people buying into your membership site. And I would think it would keep them active a lot longer since you’re straight up directing them to take action. Nice.

  34. Chris says:

    Never knew the top reason for membership cancellation was credit card issues. I figured people would make the conscious decision to actually cancel and didn’t want to be bothered anymore. I think it must be a good idea to try to engage them again with special offers to get back into the membership. Some people may just get busy and forget about it. Can’t have that!

  35. Larry K. says:

    So, you could drip the content about once per month or so, but send out emails every week about the content? Is that the kind of pace you recommend? I’m just starting out here, and your site is invaluable to learning how to actually make money with membership sites. Thanks.

  36. Debbie says:

    Super, super info! I never thought of including challenge questions in my email campaigns. I’ve always heard it’s better to give your subscribers something actionable to do regularly… and inviting them to give feedback is really keeping them in the loop. They love that.

  37. Mike Cowles says:

    Hey Robert,

    Love your content. This is great timing since I’m putting out a video traffic course and set it up to be a 4 part workshop, I think this model will be ideal for my readers.

    Your podcast is one of the best online. I love that it’s packed with action steps and legit answers for problems we all face online…

    Keep up the great work!
    Mike. <

  38. Getting your members on a sublist is absolutely crucial. I’ll definitely keep these tips in mind when I start building out my membership sites. Make it a great day!

  39. Great advice I joined Membership Cube friday and have my site up and running its going to be a Great way to build on my list. I still think that marketing is all about Know like and Trust. I am going to Awaken the folks in My Autoresponder

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