In this episode, I dive into one of the toughest aspects of running a membership business: spotting the signs that someone is about to leave your membership.

I discuss the clear and subtle warning signals you need to watch for and share practical strategies you can use to proactively re-engage at-risk members before it’s too late.

From leveraging technology to understanding behavioral patterns and key milestones, I aim to give you actionable steps to strengthen your retention strategy and keep your community thriving.

• What are the warning signs that indicate a member might be at risk of cancelling their membership?
• How can you use technology and data to identify members who are becoming disengaged?
• What are the common “off ramps” or critical moments when cancellations are most likely to occur—and how can you address them?
• Which proactive steps can you take to re-engage at-risk members and boost your overall retention rates?

Key Quotes & Takeaways:

"If someone has come and said, I think I might need to go, the worst thing you can do is ignore it or dismiss it, or treat it with hostility. Even if their specific issue can't be fixed overnight. Just taking the time to listen, to respond quickly and with care can be the difference between them leaving or deciding to stick around a little longer."

"Technology can help you to flag these things. Some software and plugins will have reporting features that will show you when someone last logged in. Some learning management systems will actually show you how long since someone completed at a lesson. You can use tools like WP Fusion, which is fantastic in enabling you to not only add tags to members that haven't logged in for a while, but also let you add a tag when someone completes a lesson or views a piece of content."

"But if you can reach out with something personal and supportive that can make the difference. Remind them that you're there. Remind them that you have resources, you have tools, you are a support service that you can help them out."

"Retention in memberships is not just about reacting when someone hits the cancellation button. Often when someone's hitting cancel, it's already too late. Retention is all about being proactive, having your eyes open, having your finger on the pulse, knowing what to look for and taking small but meaningful steps to re engage those members before it's too late."

We really appreciate you choosing to listen to us and for supporting the podcast.

We would be eternally grateful if you would consider taking a minute or two to leave an honest review and rating for the show. They're extremely helpful when it comes to reaching our audience and we read each and every one personally!

Finally, don't forget to subscribe to the podcast to make sure that you never miss an episode.

In this episode, I give you a transparent, behind-the-scenes look at a major strategic shift at Membership Academy: why I decided to discontinue our lowest-priced membership tier.

I dive deep into the challenges, member feedback, and business data that informed this big decision.

I share the lessons learned, the impact on our community and sales, and why simplifying our offerings makes more sense for both our members and our business as we move forward.

If you're considering multiple membership tiers, or are curious about evolving your pricing strategy, this episode unpacks it all.

• What prompted the initial move to a two-tier membership strategy at Membership Academy, and what were those tiers?
• What unexpected challenges and downsides did introducing a lower-priced tier create for both the business and members?
• How did having multiple tiers affect member retention, sales performance, and customer experience over time?
• Why did I ultimately decide to revert to a single-tier membership, and how was this transition communicated to existing members?

Key Quotes & Takeaways:

"They join on the lesser membership tier so they don't get all the great things that will ensure that they are as successful as they can be. And then they look at their membership and say, oh, well, I haven't had the success I wanted, so why would I upgrade?"

"As the membership industry, and indeed the online education industry, changes and evolves, with the proliferation of AI, with the shift away from search engines to answer engines that are powered by AI, as all these new challenges face us coming into the next five, ten years and beyond, then memberships are going to need an entirely different level, an entirely different kind of support."

"But what it's done is it's created that clarity, it's removed that friction, it's taking confusion out of the joining process because a confused mind doesn't buy."

"Making that pivot, making that change has been a big decision, but a one that I'm extremely confident is the right one for where we want to take the academy going forward."

We really appreciate you choosing to listen to us and for supporting the podcast.

We would be eternally grateful if you would consider taking a minute or two to leave an honest review and rating for the show. They're extremely helpful when it comes to reaching our audience and we read each and every one personally!

Finally, don't forget to subscribe to the podcast to make sure that you never miss an episode.

In this episode, I dive into three crucial things I want every membership owner to know about AI.

Drawing on insights from a recent Membership Academy roundtable, I break down some common misconceptions about how AI tools like ChatGPT actually work, the real impact they’re having on memberships, and how to adapt your approach to make the most of these changes.

Whether you’re excited about AI or feeling a bit overwhelmed by the hype, I’ll help you put things in perspective and understand where the real opportunities (and challenges) lie for membership businesses.

• What is the true business model behind popular AI tools like ChatGPT, and why does it matter for membership owners?
• How should membership owners critically approach the use of AI-generated content, given the current landscape of online information?
• What unique advantages do human-driven elements add to memberships in an age of AI-produced educational content?
• How are search engines shifting toward "answer engines," and what does that mean for content marketing and discoverability for memberships?

Key Quotes & Takeaways:

"I don't think there's going to be a continuous trend upwards of the amount of poor quality AI generated content that's out there. I think we are at a tipping point now."

"We can't rely on the fact that we know that our content is better than someone can get from AI, because your audience don't know that. And someone can get a step by step action plan of how to solve a problem from an AI tool faster than they can log into your membership or log into your courses. And they aren't discerning or informed enough to know the difference in quality. So we need to give something more than just education."

"Citing your website is not equal to your website appearing page one in Google. So a lot of marketers I'm seeing are equating the two and they're kind of telling people, hey, content marketing is still as powerful as it's ever been. But now it's just a case of making sure that you cater towards the AI tools, that you cater towards these so that they'll reference you. But the context really matters. Because someone's getting a full answer from an AI tool, they're not as likely to actually click through to the website. Like click through rate on AI answers are not a fraction of what they were for search engine listings."

We really appreciate you choosing to listen to us and for supporting the podcast.

We would be eternally grateful if you would consider taking a minute or two to leave an honest review and rating for the show. They're extremely helpful when it comes to reaching our audience and we read each and every one personally!

Finally, don't forget to subscribe to the podcast to make sure that you never miss an episode.

In this episode, I dive into the five best investments I’ve made for my membership business—investments that made a significant impact and helped the business to grow sustainably.

I reflect on where I chose to put my time, money, and attention, and why those decisions moved the needle more than anything else.

You’ll hear candid insights drawn from my own experiences, including both the mindset behind these choices and the practical benefits they brought.

If you’re looking for guidance on where to best invest for maximum results in your own membership business, this episode is for you!

What types of investments have delivered the biggest positive impact on my membership business’s growth and sustainability?

Why is attending live, in-person events so valuable for online business owners, and what unique benefits do they offer?

How can joining other memberships, upgrading audio/video equipment, and hiring specialized support each play a critical role in membership business success?

What’s the value of masterminds and high-level group programs for established membership business owners looking to hit the next level?

Key Quotes & Takeaways:

"Not only does that help me know that I'm doing my job in helping as many membership owners as I can the right way, but it helps us to reach much wider and make more of an impact across the membership industry."

"Some of the best returns that I've ever had in an investment for my business has been getting in those rooms, getting on those zoom calls with people of a certain level, at a certain point on their trajectory, with similar ambitions, similar mindset and ethos, working towards common goals, that has just been such a difference maker."

"I cannot understate the value of being in a collective that is focused, that is aligned in terms of their ambition, in terms of the kind of challenges you're facing, the kind of experiences you're having, that is so, so valuable and critical."

"Seriously, we are all online business owners and we can often forget the power of meeting up with people offline, but live events are where it's at. Make sure you go there. There's so many ways in which you can leverage them for your business."

We really appreciate you choosing to listen to us and for supporting the podcast.

We would be eternally grateful if you would consider taking a minute or two to leave an honest review and rating for the show. They're extremely helpful when it comes to reaching our audience and we read each and every one personally!

Finally, don't forget to subscribe to the podcast to make sure that you never miss an episode.

In this episode, I come clean about a big lie I’ve been telling for years: that there’s no secret formula to membership business success.

I reveal that, while there’s no easy button or magic tactic, there actually are two “magic bullets” behind thriving membership sites—but they’re not as flashy as you might hope.

Join me as I break down what these real secrets are, why they matter more than any marketing trick, and how you can use them to drive growth and retention in your own membership.

Get ready for a candid chat about data, feedback, and building a business that lasts.

• What is the true “secret formula” for membership success that most people overlook?
• Why aren’t flashy marketing tactics or miracle tools actually the answer to growing a membership?
• How can you harness the power of data and member feedback to make smarter decisions and fuel your membership’s growth?
• What practical steps should you take to collect, analyze, and act on data and feedback in your membership business?

Key Quotes & Takeaways:

"The fundamental truth is that your membership success will be so heavily fueled on data and feedback data. In terms of what are members using when you have your membership up and running? What are members using? What features are they engaged with? What features are they not engaged with?"

"People very rarely travel in a straight line from discovering you to joining your membership. And so if you're just looking at the data without the feedback to back it up, you're not getting the full picture."

"That feedback, someone who is interested enough in what you do to get on your email list, but not taking that next step. We want to know why they're not joining, not so we can pitch them, but so we can use that to refine our strategy, to refine our value proposition, to look at our offer and make sure it's actually aligned."

"How can you possibly create a membership that solves your audience's problems if you're not getting feedback from that very audience on what their problems are?"

We really appreciate you choosing to listen to us and for supporting the podcast.

We would be eternally grateful if you would consider taking a minute or two to leave an honest review and rating for the show. They're extremely helpful when it comes to reaching our audience and we read each and every one personally!

Finally, don't forget to subscribe to the podcast to make sure that you never miss an episode.

In this episode, I take you behind the scenes as I share how we’ve pivoted and refined Membership Academy in response to major industry shifts and the evolution of our member community.

I talk about why we decided to make our flagship Membership Roadmap course completely free, the thought process behind streamlining our membership tiers, and the exciting new resources and live programs we’re launching to help members scale, grow, and sustain their membership businesses over the long term.

This episode is packed with insights on adapting your own memberships to a more mature and competitive market, and offers a special incentive for our loyal podcast listeners.

• Why did we choose to make the Membership Roadmap, our signature course, available for free, and how does that reflect changes in the membership business landscape?
• How has the focus and structure of the Membership Academy evolved to better support members beyond the initial launch phase?
• What new features, live support, and advanced resources are now included in the Academy to help members with growth, scaling, and long-term sustainability?
• Why did we simplify from a two-tier to a single-tier membership model, and what does that mean for the kind of members we’re best equipped to help?

Key Quotes & Takeaways:

"We want to help people get started the right way, and if that means we have to teach them how to do it for free, then that's what we're going to do. Because I'd much rather we give away the right course than people spend money on the wrong course."

"But then we're going even further, we're scaling your business and then we're looking at that big, long term future high end stuff that you're going to be facing at that point in that journey when you get to your five year anniversary, ten year anniversary. So we really are moving the bar and we are going to be delivering this new material absolutely live over the next few months and beyond that, actually we are running Level Up Live."

"Membership Academy now is putting you on its shoulders and speeding ahead through the marathon of running a membership, growing it, scaling it, evolving it through all these new features and support."

We really appreciate you choosing to listen to us and for supporting the podcast.

We would be eternally grateful if you would consider taking a minute or two to leave an honest review and rating for the show. They're extremely helpful when it comes to reaching our audience and we read each and every one personally!

Finally, don't forget to subscribe to the podcast to make sure that you never miss an episode.

In this episode, I dive into the essential topic of delegating key tasks to a membership community manager.

I walk you through the specific responsibilities that have made the biggest impact for us, and why freeing up your time is so crucial as your membership grows.

I also share helpful advice for anyone considering hiring their first community manager, plus tips on how to get started if you’re unsure what tasks to pass on.

If you’re looking to take your member experience—and your own sanity—to the next level, this episode is for you!

• What key tasks should you delegate to a community manager in a membership business?
• How does a community manager enhance the experience for new and existing members?
• What role can a community manager play in keeping engagement high and answering member questions?
• What’s the best way to start when hiring a community manager, and how do you tailor the role to your membership’s specific needs?

Key Quotes & Takeaways:

"You can't be the rock star and the roadie. Your time, your attention is best spent on the things that only you can do. Things that are centered around really harnessing your expertise and turning it into content, turning it into coaching, turning it into opportunities to give your community access to you. That's going to take up enough of your time. And that's just the stuff where you're working in the business."

"(The role of a community manager) is much more about being almost a concierge of sorts, about suggesting that other people join the conversation, about pointing them to other resources or even tagging myself, you know, if it's something that we know that I need to chime in on them going in there and tagging me to kind of bump it up my priority list."

"If you know that you want to level up things with your member onboarding, but you just don't have the capacity for it, then these are some key things that your community manager could bring to the table."

We really appreciate you choosing to listen to us and for supporting the podcast.

We would be eternally grateful if you would consider taking a minute or two to leave an honest review and rating for the show. They're extremely helpful when it comes to reaching our audience and we read each and every one personally!

Finally, don't forget to subscribe to the podcast to make sure that you never miss an episode.

In this episode, I dive into the exciting world where gaming and memberships collide.

Joined by gamification expert Kimba Cooper-Martin, we explore what gamification really means for online memberships and how you can use playful techniques to build stronger engagement, improve onboarding, and enhance member retention.

We bust myths around gamification being just for fun topics or certain ages, get practical about challenges and best practices, and discuss the real psychology behind why gamification actually works.

Whether your membership feels “serious” or already has a streak of fun, you’ll discover strategies to motivate and delight your community.

• What exactly is gamification, and how is it different from simply adding points, badges, or competitions?
• Why does gamification motivate people, and how do you accommodate different personality types within your membership when designing gamified experiences?
• How can you apply gamification techniques to onboarding, engagement, and retention—but avoid the common pitfalls and keep things ethical and inclusive?
• Is gamification suitable for every type of membership, including so-called “boring” or highly professional fields, and how can you experiment safely without overwhelming your members?

Key Quotes & Takeaways:

"It's everywhere. So we've all played games, we've played conkers, cricket, tiddlywinks, you know, board games, video games, any kind of game you can imagine. And within those games are tools and techniques that are used to encourage you to keep playing, even when you're bored or you're frustrated because you want to get to that next level or you want to beat your opponent."

"Give people an option to opt out if you're going to run competitive things, if you're going to run challenges, you know, some people run like a five day challenge or a 30 day challenge or whatever in their memberships. If you're going to do that kind of thing, absolutely fine. Give people the option to opt in or opt out so they don't have to take part."

"If your membership is doing the same thing it's done for the last five years and you haven't made any changes, then people's minds, even if they want to engage, even if they find the thing really useful, even if it's what they want more than anything, it will naturally disengage because there's other things that are new and challenging and a bigger threat."

"How can you incorporate the senses to change the way that people interact with your membership, which obviously with online memberships sometimes that can be difficult, but you can add in little things here and there to change people's association with stuff."

We really appreciate you choosing to listen to us and for supporting the podcast.

We would be eternally grateful if you would consider taking a minute or two to leave an honest review and rating for the show. They're extremely helpful when it comes to reaching our audience and we read each and every one personally!

Finally, don't forget to subscribe to the podcast to make sure that you never miss an episode.

In this special anniversary episode, I take a deep dive into what the future might hold for the membership industry over the next decade.

Drawing from my experience and industry insights, I explore how foundational principles will persist even as we face seismic changes driven by technology, consumer expectations, and a rapidly evolving online landscape.

I address the challenges and opportunities that come with AI, the need for community-centric memberships, and how to futureproof your business in the face of increased competition and commoditization of content.

If you want to stay ahead in the membership world, this episode is packed with the big-picture thinking you'll need.

• What key industry shifts are redefining the membership landscape as we look ahead to the next ten years?
• How will artificial intelligence impact the creation, delivery, and perceived value of membership content?
• What are the foundational principles that will remain essential for long-term membership success?
• Why is building community, personal connections, and trust more critical than ever for thriving memberships in the future?

Key Quotes & Takeaways:

"Knowledge and content can no longer be your selling point. You should not be aiming to be the Netflix of your industry. If you're trying to be the Netflix of yoga, the Netflix of marketing, the Netflix of drumming, you, your business will die within the next decade because content is becoming so, so over commoditized, it's becoming so accessible and there is so much slop, there is so much to wade through and your audience isn't always going to know the difference in quality and it's not always going to be able to care."

"If you can find ways to shorten the path between problem and solution, to remove friction and deliver real tangible results, you're going to be more likely to succeed over the next decade."

"Whereas I think quite often we've always jealously guarded our audience, like we don't want our audience to hear from anyone else who has too much expertise or might, might take their dollars away from us or anything like that. I think people are really, really going to tap into the power of collaboration even more than they ever have."

We really appreciate you choosing to listen to us and for supporting the podcast.

We would be eternally grateful if you would consider taking a minute or two to leave an honest review and rating for the show. They're extremely helpful when it comes to reaching our audience and we read each and every one personally!

Finally, don't forget to subscribe to the podcast to make sure that you never miss an episode.

In this special 10th anniversary episode, I take you behind the scenes for a candid look back at the past year in Membership Academy.

I reflect on our biggest wins, tough decisions, reasons for change, and the evolution of our offerings as we hit a major milestone—ten years of helping membership site owners grow and thrive.

Plus, I dive into the launch of some exciting new features, share the realities of juggling conferences with running an Academy, and reveal what’s coming next.

This is a raw, honest year-in-review that pulls back the curtain on both our successes and the obstacles we’ve overcome.

• What were the major highlights, challenges, and changes within Membership Academy over the past year?
• Why did I decide to make the Membership Roadmap course completely free, and what does this mean for the future of the Academy?
• How did we bring back popular features like live masterclasses and member-only podcasts, and what impact have they had on our community?
• What’s on the horizon for Membership Academy and the wider membership community in the next decade?

Key Quotes & Takeaways:

"A lot of people when they say that they're going to do this, what they really mean is they're going to show off how fantastically well they're doing and then sell you the secret formula to emulating their success. But that's not really what I'm about. I'm more about showing you the realities, ugly sides and all."

"The challenge of somebody who is five years in is different from someone who's five months in. The scope of what membership owners need support with and need help with once they've launched is much broader and much wider."

"We didn't just want to release the version of the Roadmap that we had, we've re recorded the entire thing for 2025. So it's, it's all fresh, it's all bang up to date with the latest strategies. It incorporates, you know, the various advantages and challenges that AI is brought into the mix. And so it's the most up to date, cutting edge, practical, tactical, useful and all the other superlatives. The complete course for launching a new membership. And it's completely free."

We really appreciate you choosing to listen to us and for supporting the podcast.

We would be eternally grateful if you would consider taking a minute or two to leave an honest review and rating for the show. They're extremely helpful when it comes to reaching our audience and we read each and every one personally!

Finally, don't forget to subscribe to the podcast to make sure that you never miss an episode.