Starting a membership site can be a daunting task. However, I was able to chat with Jess Massey all about her membership, how to conquer the overwhelm, and the best platform to build a membership site. We will find out where she came from when it comes to the TPT world and the teacher world and how to build a membership site that will grow with your audience. 

Jess Massey is a grad school dropout turned planner designer, podcast host, and founder of the community-centered productivity brand, Hustle Sanely®. Hustle Sanely® planners and courses use the 5 Keys to Hustling Sanely to teach busy women how to pursue their goals without feeling burnt out, overwhelmed, or sacrificing their mental health and relationships. Jess is passionate about helping women manage their time and energy well so they can kiss their overwhelming to-do lists goodbye and live peacefully productive lives. 

Even though Jess is not necessarily in the “teacher space” these days, I think it's so important for teachers to see the possibilities that are out there.  So let's take everyone back to the good old days or not, and talk about what life used to look like for Jess Massey.

Although Jess got her start in the teacher space, she was never a teacher.  She was in grad school for speech-language pathology, and it was her goal to do that in the education space.  She did have a job as an SLPA while she was in grad school at a K through 12 private school working pretty much as the SLP because the actual SLP was on maternity leave and it ended up being like an extended leave.  And we all know, when you're in grad school funds are kind of low.  You’ve got to make stuff work.  So even though she didn't have money to buy resources for her students and the SLP who was there before was brand new to that school so there were no resources for Jess to pick through.  She knew she needed to get scrappy.  

She had been seeing the TPT thing on Instagram. So she made a choice to start creating resources for her students, sharing them on Instagram.  And then her audience began asking if she could put them up on Teachers Pay Teachers.  And that's how she got started in the TPT world. 

How To Increase Membership Numbers 

And then September, 2018, she created her first digital planner because she needed something to help her stay organized with grad school and working at the school and just being a human being.  Then people started to ask her to upload that as well.  At first she was reluctant because she didn't really think that it would help other people since it wasn't for her students. It was designed specifically for her. So she decided to try it out and put it up on Etsy and on TPT and it took off. At this point she felt that it was unexpected, but she decided to roll with it.  And people just kept coming and asking for help to create a schedule. That's kind of how starting a membership site came to be. Based on her ability to naturally teach people how to set goals and achieve them without getting burnt out or overwhelmed.  

That's kind of how it all panned out.  It wasn’t a straight path to building a membership, instead, it has been a whirlwind of a journey. She dropped out of grad school in January of 2019 and decided to just go for it. I love that she shares about being a dropout.  Because even though that idea has such a negative connotation she has made the most of her gifts and talents. As teachers we are told in order to make 5,000 extra dollars a year, you gotta go back to school and get your master's degree and your specialist degree.  And while I don't regret my extra degrees, they never made me a significant amount. And they weren't what I was passionate about.  And so I want to teach people to follow what makes them happy.  And if that is getting your master's degree in English, go for it.  But if you're stuck in this vicious cycle of working hard for something you are not very passionate about, find comfort in Jess’s story.

I remember when I first got sucked into the Jess Massey vortex and I think some people looking in could say, it's temporary.  Like the Instagram world is really hot right now.  And maybe Jess has a lot of followers and she's doing all these things but will it really last? What I see is so big and beyond that. She has had massive success with not only her digital planners but also starting a membership site.  

Her community, the Hustle Sanely® Squad is what they call themselves.  They're her people.  And while she may not have the largest community on the internet, or the hugest following, everything she does is to serve them.  She has created this community-centered productivity company.  

She has created a community where she is all about slow, sustainable growth.  She knows that many people feel they have made it when content goes viral.  It is all the rage to wake up to 20,000 new followers. And If that happened she would figure it out and roll with it.  But she actually loves her small community.  She loves it because she can pour into them.  She can have real meaningful conversations with them. She knows the women in her online community, she knows their names, and what they're going through.  And I think it's just such a beautiful thing.  

So in the beginning she was trying to find a way that could bring them all together because she was learning so much from them as individuals. And that’s when she realized they have something that they can teach one another, and it was her job to bring everyone together. And in the online business world, she kept seeing memberships popping up all over the place. And that’s when she began to ask herself, “How can I make this work for me?” 

She was worried she didn't have anything that could become part of a membership.  That was the first little limiting belief that popped up.  She would say to herself, “I make planners, how does that become a monthly membership.”  That’s when she had to sit down and get real with herself and say, “I really want to bring people together, and a membership is the smartest way to do that.”  

So she started a podcast in 2019 and explained her story all over the place because honestly, it has been all over the place.  People may see what you are doing online, and feel like you may have followed this really pretty timeline.  But behind the scenes, Jess is an octopus.  She is reaching in a hundred different directions, content is pouring out of her like a fire hose and not in a negative way just a lot of different directions.  There's just so much opportunity online and so many different ways you can go.  

But starting a membership site is where she found her calling and it all fell into place.  Her membership is still in its infancy, she actually launched the membership in February of this year.  So while she is still getting her bearings about juggling all the parts, she feels it is the most life-giving thing in her business because it brings people together.  It gives people who don't have a platform or don't even want a platform, a space to speak and share and teach other people.  And even though this isn’t what she envisioned when she started she can not imagine her business model without a membership now because they are her people. 

I think it's important to note that while I skipped ahead to Jess’s story of 2020 when she began to build her membership site, she actually started with teaching. Backing up to 2019, she started with a course that taught others how to create any type of digital product that they wanted to create. But oftentimes as educators, we feel that we aren't fulfilled unless we branch out into the membership space, myself included.  I launched my first course in November 2018. And I did that for almost two years before I started my own membership site.  What Jess and I both realized was that our people needed more.

When She Decided to Build a Membership like Netflix

Jess decided to build the membership site as a group coaching program. It's a five-week program where she links arms with her people.  She runs it three times a year and walks the journey with them.  But she realized five weeks went by so quickly and they were chomping at the bit for more.  Her audience started letting her know they wanted to keep going, keep learning, keep growing.  And she wanted to keep connecting with like-minded women.  And even though she felt alive during those five-week periods because she was connecting with her people, they wanted to keep connecting with each other all year long. And starting a membership site just made the most sense because it gave them what they wanted.  

And in return, she is now filled up all year long. Because as a course creator and as a product creator, it's kind of lonely when you're in course creation mode or product creation mode because you're not in the trenches with your people. So the membership gave her an opportunity to link arms with her community all year long.  

It's a beautiful stepping stone to bringing the customer down a journey. They find her through digital planners, they can purchase the course.  She can coach them.  And then the transition is an easy opportunity to keep her people connecting all year long.

Jess describes her customer journey as a staircase. Where her audience can find her through Pinterest, Etsy, or even Teachers Pay Teachers. They buy the cute planner and go on their way. But she has really taken the customer journey to a new level. She offers a single page inside her downloads that offers productivity tips in the form of her podcast. Then the Podcast explains the membership benefits to them. And they are able to commit to her program from month to month. The membership then gives them the opportunity to keep learning and growing. And then since Jess continues showing up, providing value inside the membership site the people want to stay because they want to keep learning from her.  

Build a Membership Site To Connect With Your People

The way Jess runs her membership for teachers is with a topic every single month and her members get a workbook and she does a coaching call with all of them, like a group coaching call.  They work through the workbook. And then throughout the month, they are chatting in the Facebook group.  They do Zoom calls so that they’re face to face, a more casual Q and A, very similar to what we do inside the CEO Teacher® School. The members inside both Jess’s community and the CEO Teacher® School are so connected that they don't want to go anywhere. It is such a beautiful space that they are all cultivating together. 

If you have what we like to call a sticky factor inside of your membership, people are less likely to leave.  I think Stu McLaren talks about sticky factors inside of a membership. So let's just kind of get nerdy about membership talk for a second. It's really a great marriage between teaching and helping and serving people. 

Which is best? A Patreon or Kajabi Membership Site?

In the beginning, Jess’s audience kept telling her to create her membership on Patreon. It's kind of like a creator's platform.  A less intense version of Kajabi.  And it's just a place basically where you can grow a community.  So Jess started there with literally no plan.  She knew everyone in her audience wanted Patreon.  So she decided to build a Patreon site.  She originally went live once a month and did a Q and A, where she charged $10 a month.  But she started feeling like she wasn't offering enough value.  So she shut it down because she didn’t have a game plan.  

Her misconception was that starting a membership site needed to be more complicated. But once she made a plan she realized that as a productivity coach overcomplicating the content wouldn’t make people stick around. So now there are some guaranteed things her people get each month. They get a monthly downloadable bundle, a workbook where they can take notes during the monthly coaching call. And a planning page that has all of the membership dates, and phone backgrounds. She creates this content quarterly and then is able to repurpose the content each month. 

She also has a vault on her Kajabi membership site where she can sell the coaching videos and the workbooks from the membership for $20. So if somebody signs up for the membership and thinks they really liked what she had talked about two months ago, they can go back and purchase that bundle.  Or if they just want a single bundle rather than the whole community they can go buy that bundle. So as you are creating content for your membership, work smarter, not harder.  

Put in a few intentional hours to create really good content for your membership. Jess uses her membership to create content for her podcast.  And then she creates Instagram content from her coaching calls.  And most importantly she has repurposed it and resells it in the vault.

I feel like that's a huge secret that nobody talks about.

I create the heart and soul of the program each month. The one piece of content that everything we do in our CEO Teacher® business stems from. Our podcast episode is where we start at the top of the pyramid. I create the podcast content every week. I put in the work there and then luckily we have people now on our team that help create show notes, blog posts, and Instagram posts. We create Facebook posts using that original Podcast content. We get our topic for the membership for the month.  So it's this beautiful thing that is seamless. And it's easy once everyone's on the same page. Your membership can be seamless and it can be easy.  

Creating A Membership Site for Your Perfect Crowd

Jess tells her members all the time they are her long game.  Since she is half service-based half product-based she spends time creating products and pouring energy into her community. She spends some time deciding what the king content is for the membership.  So for the whole year, she plans out 12 topics. And then builds podcast episodes off of that topic. From there she plans her Instagram, email, resources, you know, all the things.  

She currently has over 200 members and she has hardly promoted the Kajabi membership site at this point because she’s not ready for that big influx of members YET! She is focused more on the product side of things right now. There's no cap to the membership and your workload does not change, plus as the community bonds, it gets stronger.  She has decided to be open and transparent with members of the group.  She knows she shows up to do the coaching call once a month but she feels that her members really run the community.  They're in the group every single day, creating conversation, sharing podcast recommendations, talking about how they're using their Hustle Sanley® planners and how they are setting up for the following weeks. They're in there creating the content for her.  And then based on things that she is seeing going on in the community, she elaborates on that on the podcast.  Her community is giving her content ideas. She recently gave her people a sneak peek at the 2022 planner that's coming out and they felt so seen, so special. She reminds them that the community is theirs, and they are giving back in the form of content ideas. 

And you know I am a big picture person and want to set goals for years from now. So when I asked Jess about her 5 and ten-year goals she really came through. Her goal by the end of this year is to have 300 members in the BFF membership, which is 100% possible.  And then next year she wants to double that because that's where she’s going to be putting all of her energy.  Jess puts it in perspective when she says, “don’t be so quick to reach over the top of the people in your path, or kind of look past them, trying to gather more people”.  

Let's Recap How to Start a Membership Site…

So to recap: Jess shares the four things that she believes are essential to running a teacher membership or starting a membership site. 

• Start small: Don’t overcomplicate the content and find ways to repurpose what you are creating each month.
• Take time choosing your platform: Make sure it will fit your needs, take payments, a place that is a solid platform on the back end.
• Decide on the meat of your membership: Where will you put your energy each month to make it amazing for your audience?
• Do something FUN once per month for your members: Create a community where there is room for everyone on the playground and they all feel connected.
  

If you are wondering about starting a membership site, and need more inspiration, check out these articles:

13 Membership Site Examples

Building Your Own Website to House Your Membership

How to Build Educational Membership Students Will Love

How to Create a Profitable Membership Site

And since I know everyone's going to fall in love with Jess, you can find her on Instagram since that is where she hangs out most. Everything else lives at www.jessicamassey.com ~the podcast, the blog, all of her planners, everything lives there.  But her favorite place is Instagram stories and her membership Facebook group, of course.