10 Lessons Behind Sunsetting Our Membership

Most people would have a fire sale; not us.

Most people would have a fire sale as they sunset an offer.

We’re doing it differently, of course. I love getting uncomfortably truthful about the behind-the-scenes of running a global brand that serves founders like you. We’re blazing in our lessons to light your torch as you revolutionize your own industry with your own creative ideas.

Take our lessons; may they help you along the way. 

Lesson One: The story of The Cheetah Coalition Membership and why we’re closing her down (and not having a fire sale)⁠

A sale of goods or assets at a very low price, typically when the seller is facing bankruptcy.⁠ When I see someone sunsetting an offer and having a fire sale I unconsciously think about the line above – “facing bankruptcy”. By no means true for every company or organization that’s ever had a fire sale, but after a decade+ in marketing, sales, and leadership… it’s what I think of.⁠


Fire selling our freaking lessons from running a profitable membership that went from a 33% churn rate to a 0% churn rate (for two years) while members were actively moving into new offers with us (26% of them, in fact). ⁠


The big reason she’s being let go: we no longer serve early stage entrepreneurs without a prerequisite list that’s hefty so we can be of best service to them. ⁠

⁠We support clients that have seen success, are interested in re-evaluating, repositioning, and renegotiating their value in the marketplace. It’s our sweetest sweet spot and what has made up more than half of the clients we’ve signed in the last four years. Five years if you include my time freelancing. ⁠

⁠Lesson Two: Retention retention retention (monthly recurring revenue meets churn handshakes with the next most important part of memberships)⁠

⁠Our longest standing member was a member for 2 years or 733 days. She continued to purchase from our suite and became a 5x buyer. 

We didn’t have to seek another founder to support… She walked through every one of our offers and is currently interested in our next offers (a mini-mind and consulting). She’s a literal PEACH and we love and adore her (our whole team is actually semi-obsessed with her). 

The mini-mind would be for 9 months and consulting would be for 12 months. Again, another founder we’re able to support for the long-haul instead of starting anew with a new relationship. 

Our lowest standing member was for 3 months. 

We’ve only ever had one subscriber (this member being mentioned!) that walked through The Cheetah Coalition doors and ONLY stayed for 3 months. Most of our members had a range of 6-20 months. 

Because we made a customer journey that was tailored for her through public and private offerings. Knowing how to do this is your ease-filled, customized, bespoke way to serve your clientele with such ease that it feels like you custom-craft for every client (but really you custom-craft for each buyer type and buyer persona, keeping the similarities similar and the bespoke pieces bespoke). 

Lesson Three: Customer Journey & Helping Members Move

There’s such a desire for passive income that business owners can forget that the majority of recurring revenue comes from trust in ONE offer and the ladder to many other offers.


This membership gave us the opportunity and runway to see how to support and serve in various ways, building pathways for the different styles of clients in the group to move from one offer to the next.

Some members became 2-5x buyers.

Some members spent $200 in the membership and then moved into spending $10k for consulting.

Some members invested $10k in consulting and then sent referrals to spend $10k for their consulting support.

We could have a virtual retreat about customer journey and customer journey alone, but we focused on a value-ladder approach for clients to be able to jump from one rung to another. The clients that spent $200 in the membership and then moved to consulting? They signed up and learned what they needed, but they were in their 3-6th years of business… private consulting made more sense to develop a deeper strategy based on their years of experience.


We love a cutey percentage: 26% = clients that converted to new offers: 

Though this is great and higher than brand new leads from an industry standard perspective… it still wasn’t as high as I wanted it to be even after refinement, regular market research, etc. 

Could we continue on and definitely improve this? Yes. 

Is it a puzzle-piece that fits with our current market fit, our desired vision, and ideal clientele style that we want to grow in our suite? Nope. 

Releasing with ease and joy and gratitude for what was and no longer is. 

But why did we have such high retention and high conversion to new offers? Research, refinement, rapport, and respect.

Research: I talked to our members privately, asked questions in the group to re-evaluate what they loved and didn’t (by their words), we watched their actions via our email list (were they opening emails, what were they clicking on, we listened to what were they mentioning to us in the group and on social, we watched their social content change and shift and evaluated their state of mind/perceptions/psychology based on what we could see.  

Refinement: I reviewed the membership every quarter to re-evaluate what was used, what wasn’t, and deepened our focus on what was used.

Rapport: We built relationships that were real, deep, and developed. We noted life details about all of them: are they married, do they have children, when’s their birthday, what are they launching, what are they excited about, what are they struggling with… the list goes on and on. We got to know our members intentionally and stayed updated on them. 

Respect: We respected their experience, we sought to be as connective and supportive as possible, we honored the container and looked for ways to support them in deeper ways beyond the membership and respected when they were happy where they were. We respected their businesses, their visions, their dreams, their goals, and constantly hyped them the eff up because we believe in them.

Low ticket does not equal a low experience. Many have been burned in the online space and we actively work within that known fact consciously to support in ways that go above and beyond.  

Lesson Four: What I did and didn’t love about running a business membership for female founders from 2021-2024


Intimacy, loved the clients that walked through the door, connecting weekly with the members, hosting a community where women could be vulnerable about what’s working and what’s not working while learning tactics and strategies to stay ahead of the curve while embracing a timeless experience in their businesses. 

I loved hosting powerhouse female founders as speakers, loved marketing what we were talking about, AND loved structuring the membership (it’s so different from other memberships on the market… we made sure of that).

I loved leveraging my lived experience to advise other founders with their memberships to make their memberships work faster, better, and simpler than ours, loved the connections it made, loved the vibe and branding, and loved innovating often and serving well.


The constancy of creativity (new themes, new topics, new shiny everything) — I quickly learned to reimagine content, and have certain days of accountability posts that were safety triggers of reused info (shoutout to positive focus Fridays).

The constant feeling of “should I relaunch this or let it be healthily evergreen” (we went evergreen pretty quickly because relaunching this program invited in a lot of early stage entrepreneurs when the rest of the suite spoke to mid, advanced, and established brands (3-20+ years in the game).

The weekly work that was intimate but not intimate enough for my liking (within consulting we touch base with clients often in email, ClickUp, and Voxer — I learned to detach from the membership and allow for our team to touch base with members daily while I communicated every few days within the group or day-of if there was a strategy Q that the team couldn’t answer, but it still didn’t feel like “enough” for my desired level of intimacy with our clientele.

Though so sexy with it’s monthly recurring revenue, receipt bumps through price bumps, lifetime value, and growth clients (moving from one part of their customer journey to the next), I felt like I’d rather host courses, detach from the client’s learning experience and stop in after purchase, mid-way, almost finished, and the finish line of the course to better understand where I could serve.

Lesson Five: Why we’re NOT having a fire sale as we let go of The Cheetah Coalition Membership…


There’s a line in The Artist’s Way about how creatives don’t mourn their losses. 

Their creative works that didn’t pan out the way they had hoped and dreamed as they were actively creating. I feel like our membership DID pan out in the way I hoped and even more so. 

But I’ve not seen a creative funeral online without a fire sale. 

I’m not interested in retrieving more cash, eyes, or interest on this offer; I’m interested in showing you how to release an offer that no longer matches with the long term vision, has had many iterations of refinement and still feels like a stranger in the sanctuary of creativity that TCC has created…

…and we do have a distant cousin that’s sophisticated and savvy… coming in to take her place. 

Welcome to the non-fire-sale-creative-funeral-meets-new-birth. We’re still working on this line; she’s a mouthful. 

Lesson Six: Learning to master the art of facilitation and having the right speakers in the room

The art of facilitation is a major equivalent to your perceived value in the marketplace. 

I know 2024 is the year of not caring how you’re perceived as a person, but how you’re perceived as an educator does define retention, trust, referrals, and connection. 

  1. Slow down when you speak; speaking fast and furious shows a lack of confidence
  2. Breathe; breathless speech shows that you’re worried, cautious, and in a state of fight or flight
  3. Deepen; deepening over widening will allow for profound support to be received from a group even if you’re not working 1:1 


We’ve had the honor of having nearly 40+ speakers in the Coalition that range from energetics to strategic support to help female founders re-evaluate their lives and businesses with ease. We were into lifestyle design from the beginning because my past experiences with burnout helped me see the true meaning of having a life that is valued before intermingling it with work. 

We’ve hosted 40+ hot seat coaching calls in the last few years alongside our several part framework, treasure chest of resources and implementation files, and we’ve been in the membership every week with 1-3 team members since its genesis to connect with the members. 

Memberships = work 

It’s not a set it and forget it offer. It requires love, devotion, dedication, responsibility, and true enjoyment of the process. 

Lesson Seven: Marketing and why we rarely marketed the membership

As a marketer of 10+ years, why oh why did I choose to not market the membership often? 

I noticed a few things after our first three launches:

The membership was made for early stage entrepreneurs.

We’d have a plethora of connections, engagement, and sales conversations with early stage entrepreneurs for the membership, but there’d be a lot of interest in our agency, coaching, and consulting, too. They weren’t ready for those areas and the next offer in the ladder we had for early stage entrepreneurs was a 90 minute intensive with 2 weeks of implementation support. And I was repeating myself a lot in those intensives. 

I started categorizing what those folks in those intensives needed and began to infuse the membership with that content in our hot seat coaching calls. Giving me a way to organically sell into the membership (behind-the-scenes) when folks were interested in our agency, coaching, and consulting but weren’t quite ready yet in their business timeline. 

The majority of our offerings started out being for messy middle entrepreneurs with some success that wanted to double-down. 

It’s refined again and again to what we do now: re-evaluating, repositioning, and renegotiating your true value in the marketplace. 

Lesson Eight: What I wish I would have done from the beginning


I watched our free resource click throughs like a hawk and organically connected with anyone that didn’t convert from the funnel that leads to the membership. I did the work most won’t talk about: personally invited folks into the offering from our email list when the funnel didn’t convert them and if it was yes, no, or maybe… I did the work from there to gain their trust and brand loyalty through relationship, rapport, and respect of their state in the customer journey. 


The true and real information here: we always meant to. It’s a regret. LOL. There’s no excuse or delicate reason why we didn’t. If you’re going to start a membership, take the time to prep this before you even roll it out. There’s a bajillion reasons why, but a main one that I know is sexy for almost anyone to read: it’s authoritative and shows that you trust in your product so much that you’d pay others to help the movement be spread clearly and widely. 

Marketing the internal pieces of the membership more publicly (but still glad I didn’t at the same time)

We shared the speakers, we shared details of what we’d talk about within the group, we’d share screenshots, but if I did it again I’d double down. This offering would have had to be different for us to publicly communicate about it often (since it’s for early stage entrepreneurs and the rest of our suite isn’t), but if this was a place for some to re-evaluate their brand without me in the room… I’d market it completely differently than we did with a focus on the two aforementioned pieces above. 

Lesson Nine: How I’m looking at this offer to best take what matters, leave what doesn’t, and feel satisfied for what it added to our creative legacy and satisfied as I sunset it.


How did this offering help our clients? Review social proof, market research (customer satisfaction surveys or C-SATS), and review progress (spreadsheets and information we’ve collected about clients in the membership, their growth, their successes, what they need more of to help their journey).   

How could it have helped clients more effectively? Script out what was lacking in the offering (there’s always room for improvement; seek to review your works like an academic or a scientist and detach personal affection to the offering just for the moment!) Review the above in question 1 to then take market research and lack of progress into account. Was it the offer? Was it the marketing that communicated to the clientele? More specifically, were there values and psychographics unconsidered in the marketing process, welcoming in ill-fit clientele? With a self-paced membership, grit, gusto, gumption, self-responsibility, and self-accountability are required even with the coach’s accountability, processes to support growth, ease of material review, regular reminders of content and access, etc. Remember it’s going to be nuanced and your research isn’t perfect; equivalent responses on both sides of the table (the offer/facilitation and the clientele) is necessary.

What were the biggest changes seen from clients being in this offer? Double-down on celebration after you review how it could have been better. Your brain acknowledges negativity more than positivity (we’re born this way as Gaga would say) – work to bring in 5 positive thoughts for every negative. Stretch your brain with some brain retraining as you prepare to take what matters and leave what doesn’t. 

Lesson Ten: Sunsetting this offer gives us an opportunity to serve the clientele that’s all up in our DMs, on our email list, and lurking BTS. 


After years of serving hundreds of founders around the globe through our programs, private consulting, and retired agency… our sweetest sweet spot is helping female founders like you re-evaluate, reposition, and renegotiate your true value in the marketplace.

Equipped with intimate community, knowledge, and bespoke support for your life and business, you’ll gain peace and joy in your life and business legacy, creativity throughout your business growth, and the reputation of being an ease-filled & trustworthy brand. 

We’re here to provide you with the mentorship, tools, & resources you need to go from just being just another business owner to being an unrivaled brand in the marketplace.


Raise your voice through thought leadership, raise your rates, raise your worth, and raise the bar as you bring unparalleled growth into your life and brand portfolio. 

We love guiding mission-driven laidback luxe brands that love the heart-data & the hard data – something that really only happens after a few years in the game of entrepreneurship. Data becomes the pillow to sleep your head on at night, knowing that you have everything at your fingertips to curve your creativity around.


Team Cheetah has been actively re-evaluating the brand since January of 2023… it’s taken a year and some to get to this point of being prepared to unveil…

  • Our repositioned brand (visuals, messaging, our brand guidelines are focused on the clientele we’ve been actively working with)
  • How we’ve restructured our BTS (team, offerings, what we bring to the table by infusing digital and in-person in fresh ways) and the way we work best with clients & our team’s energetic cycles 
  • Re-evaluated how much I’m in the brand (I’m Ash, the founder, and last year after my brother-in-law’s death I recognized how much more I wanted to get out of the day-to-day of running a business and we were already in the process of removing me from as much as possible but 2023 was our double-down year)
  • Raised rates (we help clients give colossal results in life and business – it’s an investment to work with us and always has been, but our pricing strategy has shifted in the last 365 days, starting early in 2023).


Ashleigh Henry has been in marketing, sales, and leadership positions for the last decade and it was exhilarating for Ashleigh to climb the retail, corporate, higher education, and start-up ladder holding positions such as Marketing Strategist, Copywriter, Social Media Strategist, Manager, Editor, Co-Editor…until it wasn’t. Alongside her degree, Ashleigh decided to bring all of her experience into the freelancing world until it became clear that she didn’t just want to pay the bills – she wanted to create a company that was foundationally built on cheetah print, legacy-minded marketing, and sexy sales structures that could stand the test of trend and time. The Cheetah Company, founded by Ashleigh, does this for female entrepreneurs through their education, coaching, and consulting services. Learn more about Ashleigh here.

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