A year is a long time in a membership. Long enough for members to forget their renewal date, let their card expire, or get hit with a charge a few days before payday.

In this episode from the vault, I walk through exactly how I handle annual renewals in Membership Academy so members are never caught off guard. I share the email sequence that kicks in 11 months after someone joins, why I tell members how to cancel, and why keeping renewing members on their original price is one of the strongest retention levers you have.

I also share how one membership switched to manual renewals, offered a renewal-only lifetime deal, and saw its renewal rate go up.

If you offer annual or six-monthly plans and want fewer failed payments and more members choosing to stay, this episode is for you.

• Understand why longer billing cycles lead to failed payments, disputes and surprised members
• See the final-month email sequence I use in the Academy, starting 11 months after someone joins
• Learn why pointing members to the cancel button actually protects your business
• Discover how recapping past value and signposting future value creates a “pain of disconnect”
• Find out how a renewal-only lifetime offer increased renewals and lifetime value for one membership

Want the exact setup I use to stop annual renewals from failing? Grab the free Renewal Safety Net at membershipgeeks.com/497. It includes the final-month email sequence, a failed payment fix table and a setup checklist.

And if you’d like a wider view of where the gaps in your membership business actually are, our free Membership Healthcheck is built for exactly that.

Key Quotes & Takeaways:

“We’d far rather somebody who doesn’t actually want to renew take that action and cancel their account than have them get billed again and then complain to us, or dispute the payment, or kick up a fuss.”

“That signposting of future value creates a bit of pain of disconnect. It means they need to make a decision to not get this stuff that’s coming up.”

“Showing that people continue to get the rate that they first signed up for is huge for retention.”

“When that renewal payment goes through automatically, the decision stays a passive one. You don’t need to do anything if you want to stay.”

You might also find useful:

• Should I Charge Monthly Or Annually For My Membership Site?
• 4 Essential Email Automations Every Membership Website Needs
• How to Identify Your Member Drop-Off Points
• Tips For Dealing With A Downturn In Your Membership

Thank You For Listening

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.

As fantastic as your membership may be, not everyone sees joining as a no-brainer. Some people sit on the fence for weeks, almost ready to sign up but held back by something they never quite tell you.

In this episode, I'm heading back into the Membership Geeks vault to break down the five most common objections people have to joining your membership, and what you can do to overcome each one.

I also share the one question you should be asking your audience right now to find out which objection is really costing you sales.

• Why dropping your price is the wrong response to "it's too expensive," and what to do instead
• How to reassure people who are wary of recurring subscriptions
• The social proof and risk reversal tactics that prove your membership delivers
• Simple ways to make people feel safe entering their card details
• How a "who this is for (and who it isn't for)" section helps people decide whether the timing and fit are right

Want to find out exactly which objection is keeping people on the fence? Grab the free Fence-Sitter Planner at membershipgeeks.com/496. It includes the email to send your non-joiners, a bank of questions to ask, and a tracker that matches each objection to the right fix.

And if you'd like a wider view of where the gaps in your membership business actually are, our free Membership Healthcheck is built for exactly that.

Key Quotes & Takeaways:

"So social proof is your strongest weapon against this objection. You want to be getting testimonials, ideally video testimonials."

"The less conditional your money-back guarantee is, the more someone will actually value it as a valid form of risk reversal."

"People are usually too scared of putting anything out there that might turn away members, but you don't actually want to attract people who aren't the right fit."

"It's one of the most valuable questions you can ask. Why have you not joined the membership yet?"

You might also find useful:

• Overcoming 5 Common Objections to Joining Your Membership
• Are You Using Risk Reversal To Increase Membership Sales?
• Essential Features of a Successful Membership Sales Page
• Should I Offer a Trial for My Membership Website?

Thank You For Listening

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.

At some point in every membership's journey, you'll have to decide whether to raise your price. That's a good thing! It means your membership has grown more valuable since you launched.

But there's a right way and a wrong way to do it, and this week I'm on my soapbox about the very, very wrong way. My video host took my annual renewal from about $900 to $4,500, with less than one months notice and a single email that was easy to miss...

If it isn't obvious to spot, I break down exactly what they got wrong, why I only raise prices for new members, and what you can take from it for your own membership.

If you're thinking about a price increase, please make sure you never handle it like this.

• Why considering raising your price is a healthy sign for your member
• How an upcoming price increase becomes one of the most profitable promotions you can run
• Why legacy pricing is a silent retention tool that gives members more reasons to stay
• What Vimeo got wrong, and the communication, clarity, and fairness lessons you can apply
• Where the line sits between a smart save offer at cancellation and rubbing it in

Want a clear plan for doing it the right way? Grab the free Member-Centric Guide to Raising Your Prices.

And if you'd like tailored advice and support on where the gaps in your membership business actually are, join Membership Academy here.

Key Quotes & Takeaways:

"That price increase promotion is phenomenally successful. It's always one of the most profitable, the most successful types of promotions that I see other members in the academy running."

"Because if they do, they obviously lose that legacy pricing. So it becomes really good for member retention."

"When we're doing price increases, communication, clarity, fairness is absolutely paramount."

"Putting existing subscriber prices up should be the absolute last resort. It's unfair. It's difficult to do."

You might also find useful:

• The Hidden Costs of Legacy Pricing (And What to Do About It)
• Should You Increase the Price Existing Members are Paying?
• 11 Signs That it's Time to Increase the Price of Your Membership
• How to Deal With Member Cancellations

Thank You For Listening

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.

I always talk about the fact that memberships are an evolution. They're constantly changing. The membership you launch won't look the same in six months, twelve months, or five years, and most of the time those changes are small and slow.

But every now and then the change is more substantial, sometimes an entirely different topic you end up switching to. So how do you pivot in a significant way without alienating your existing members?

In this Ask Mike episode, I revisit a question from one of our live member Q&A calls to break down exactly that. If you're weighing a real change to what your membership is about, this episode is for you.

• How do you tell whether a change is a genuine pivot or an entirely different membership in disguise?
• What's the honesty test to run before you announce anything?
• When should you run two memberships side by side instead of forcing a switch?
• What do you do with the members a partial realignment leaves behind?
• Why does timing matter as much as the message itself?

If you need your membership questions answered, head over to Membership Academy to join our next live Q&A!

Key Quotes & Takeaways:

"Deep down, if you're really honest and blunt with yourself, is this just not what people signed up for?"

"If this was a brand new membership, would you actually market to these same people? Or is this an absolute departure from what they've joined for?"

"The rest of it is just communication. It really is communication."

"You can't just have them keep paying you for a thing that you're just going to switch out for something else."

You might also find useful:

• I Need To Pivot My Online Membership. Help!
• Why Membership Site Owners Need to Embrace Change
• Inside Look: Pivoting the Membership Academy
• 4 Huge Ways Membership Academy is Changing

Thank You For Listening

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'm sharing the second half of my closing keynote from Retain Live 2025, where I break down the four essential components of a scalable strategy for your membership business.

Most membership owners think scaling means working harder: more content, more posts, more bells and whistles. That's not it. So many of us don't have a clear answer for what we're actually building toward, and without that clarity, we end up chasing tactics instead of building real leverage.

I'm walking through the three revenue routes you need to balance, how to stop being the bottleneck in your own business, why there's no secret formula (but there are two things that come close), and why the memberships that actually break through are the ones willing to make a genuinely big bet.

• The three revenue routes that actually grow a membership business, and why chasing new members alone won't cut it
• How to build strategic leverage so your business doesn't depend entirely on you
• The two "magic bullets" that actually drive growth (and why they're not what you think)
• How to design a controlled experiment instead of guessing what will work
• Why making a big bet on yourself might be the move that changes your trajectory

Want a way to actually test your next idea instead of just hoping it works? Grab the free Experiment Design Worksheet, it walks you through turning any idea into a proper hypothesis, controlled test, and decision, using the exact framework from this episode.

Key Quotes & Takeaways:

"Memberships are a retention game. They're not an acquisition game, but ultimately more members does make it more likely you'll make more money."

"The third, and the most overlooked revenue route, and the most powerful, is increasing your member lifetime value."

"Data tells you what people do. Feedback tells you what people think. The truth lies somewhere in between."

"What got you here will not get you there."

You might also find useful:

• Why Member Lifetime Value Is More Important Than Churn Rate
• How To Level-Up by Creating a Membership Ecosystem
• 6 Areas to Focus on When Scaling Your Membership Business
• You Need To Prioritize These 8 Things in Order to Grow Your Membership

Thank You For Listening

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.

Back in 2025, we ran our second ever live conference, Retain Live, and my closing keynote there was called Scalable Strategy. It's all about the things that take a membership beyond just a marketing or retention strategy into a genuine long-term plan.

This episode is part one of that talk. It tackles a question most membership owners have never actually sat down and answered: what are you building, and why?

We get zoomed into launch goals, then revenue goals, then member count goals, and the bigger picture rarely gets a look in. If you've hit a growth plateau, or you just have that nagging feeling you're working hard without working towards anything in particular, this episode is for you.

• Why the tactics that got your membership to where it is now will eventually stop working
• What's really behind most membership growth plateaus (it's rarely what you think)
• Why fear of change is the thing quietly keeping you stuck
• How to figure out whether you're building an empire or a lifestyle business, and why that distinction matters
• The four exits every membership owner will eventually face, whether or not you ever plan to sell

Want a guided way to actually work through your own end goal? Grab the free Define Your End Goal Planner, walking you through where you sit on the empire-to-lifestyle spectrum, what "done" looks like for you, and which of the four exits you're working towards.

And if you'd like a wider view of where the gaps in your membership business actually are, our free Membership Healthcheck is built for exactly that.

Key Quotes & Takeaways:

"What got you here will not get you there. If you want to get to that next level, it's going to call for a different approach."

"The audience stops growing and eventually the well runs dry, because every sale you get from an audience that isn't growing is increasing the ratio of non-buyers and never-buyers on your list."

"You're not less of an entrepreneur if you just want to create an amazing lifestyle. You just need to be asking yourself this question, finding clarity around where this ends."

"It's not one huge cataclysmic exit event. For memberships, it's more like four exits."

You might also find useful:

• Setting Goals For Your Membership Business: A Practical Process
• Why Your Membership Signups Have Slowed Down
• How to Handle Shutting Down Your Membership Website
• The 3 Pillars of Exponential Membership Growth

Thank You For Listening

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.

This episode isn't about your membership. It's about you, the person running it.

You could have the best content, the smartest retention strategy, and the tightest community in the industry, and none of it matters if the person at the helm is stretched too thin, winging it, or quietly burning out.

I've spent years watching who lasts in this industry and who burns brightly for a year or two and then disappears. It always comes down to the same five things, and none of them require any kind of special talent.

This is for you if you've ever wondered whether you're working on the right things, or you're starting to feel that first flicker of dread before a live call.

• Why knowing a handful of key numbers beats "flying blind" or drowning in data you never act on
• How vague goals like "grow the membership" quietly guarantee they never happen
• The difference between busywork and the work that actually moves your membership forward
• The specific mindset gremlins (perfectionism, imposter syndrome, comparisonitis) that derail even experienced owners
• The early warning signs of burnout, and why ignoring them puts your entire membership at risk

Want a guided way to catch your own burnout warning signs before they take you out? Grab the free Banishing Burnout Workbook. It walks you through spotting your personal early indicators, auditing where your week actually goes, and setting two boundaries you can start this month.

And if you'd like a wider view of where the gaps in your membership business actually are, our free Membership Healthcheck is built for exactly that.

Key Quotes & Takeaways:

"When you don't know your numbers, every decision becomes guesswork."

"Nobody wins if you lose."

"A burnt-out founder can't run a membership, and a membership without its founder will quickly fall apart."

"They know that self-care, that looking after yourself, isn't a luxury. It's a strategy."

You might also find useful:

• Avoiding Burnout When Running A Membership Site
• 9 Non-Negotiable Traits of Thriving Membership Owners
• Time Management I Use to be a Productive Membership Owner
• KPI's Every Membership Site Owner Should Be Measuring

Thank You For Listening

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.

Every month inside Membership Academy, I run a live Q&A where members bring me their toughest questions. One that keeps coming back around is this: should you onboard trial members differently to your regular paying members?

Most people either run one blanket onboarding sequence for everyone, or assume trial members need something completely different. Neither is quite right. The answer comes down to a concept I call the off-ramp, and once you understand how your trial length lines up (or doesn't) with your natural off-ramps, the right approach becomes obvious.

• Should your trial onboarding be the same as your regular onboarding, or different?
• What is an "off-ramp," and why does it decide how you should structure your trial sequence?
• How does a 2-week trial change your approach compared to a 1-month trial?
• How do you detect (and nudge) trial members who haven't actually used their trial?
• What's the case for letting trial members skip the trial altogether?

Want a simple way to check your own trial onboarding against this? Grab the free Trial Onboarding Timing Map at membershipgeeks.com/490. It maps out exactly what should change based on your trial length, plus ready-to-adapt nudge and upgrade prompts.

And if you want a wider view of where the gaps in your membership strategy actually are, our free Membership Healthcheck will show you in about two minutes.

Key Quotes & Takeaways:

"There are some natural off-ramps within the member journey where people are more prone, more likely, more at risk of leaving your membership."

"If someone signed up for a trial, there's less impetus for them to actually use what they've signed up for than if they'd paid for it."

"Assuming your membership is as awesome as it should be, all you need to do is you get people using the membership, you get them getting results, you get them consuming your content, then that's going to make it far more likely they'll stay than if they've not used it."

"When somebody joins on a trial basis, they are not entering with the same expectations, with the same commitment level, with the same intent and purpose to someone who would be joining as a regular member. They are not the same, and therefore your onboarding should reflect that."

You might also find useful:

• Advanced Tips and Tactics for Offering a Membership Trial
• Should Membership Trial Periods be Free or Paid?
• 5 Things to Include in Your Member Onboarding Sequence
• Why you need a solid member onboarding process

Thank You For Listening

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.