The CX 006: MRR (Monthly Recurring Relationships) with Rosie Sherry

The CX 006: MRR (Monthly Recurring Relationships) with Rosie Sherry

Jillian Benbow: Investing in relationships has nothing to do with revenue, but it also has everything to do with revenue and like many things in community work that might be somewhat confusing because hey, at the end of the day, community is messy. Fortunately, there are things we can do to make it as succinct as possible, which is why we’re excited to talk to Rosie Sherry of Rosie Land, who will share some of her many great insights based on her own experiences on today's episode of The Community Experience.

Tony Bacigalupo: Hey, Hey everybody, Tony Bacigalupo here and I've got my cohost Jillian as well.

Jillian: Hello.

Tony: And we are going to be speaking with Rosie Sherry today. She works with a company called Orbit, which helps you get a better handle on what's going on with your members. Get some good data on what to do with them. She's just been an amazing community leader, writing and talking about community online through her newsletter and through her Twitter account, which is kind of where I first came to know about her. She also spent a couple of years as the community leader at Indie Hackers, which for those of us who know the Pat Flynn Smart Passive Income side of the world, Indie Hackers is just a really great free online community for folks who are building their businesses. She's just had her hands in a lot of different, great community activities. And we're going to learn today a little bit about first of all, her efforts to gracefully exit some of her past efforts and a little bit about how the company she works for uses data to get a better handle on the communities that they work with.

And then also just the power of really focusing on the relationships. And we'll get to know a favorite phrase is that I've learned from Rosie, which is monthly recurring relationships, our new favorite KPI. Jillian, what do you think about the episode we've got coming ahead? What are you looking forward to sharing with folks?

Jillian: I think the new take on MRR as a metric is pretty fascinating, but yeah, it's always great to talk to somebody who's been in community for a long time, like myself, and to really just see where their journey took them because it's still so wild and free as an industry, as a career path, and so it's just fascinating to see how people built upon their own.

Tony: Rosie's got such a chill approach to things, too. We'll talk more about that kind of on the other side of it, but I'm just so excited. Definitely check out Rosie's tweets while you're listening or after you're done with the episode. Go ahead and have a look at her account. She's @RosieSherry and enjoy this conversation while you do that with Rosie Sherry on the community experience. All right. Rosie Sherry. So great to have you on the program. Thanks for taking the time to join us today.

Jillian: Yeah. Welcome to the show.

Rosie Sherry: Thanks for having me.

Tony: Where in the world are you right now, Rosie?

Rosie: I'm in Brighton in the UK.

Tony: You're in Brighton. So it's a little bit later in the evening there. Thank you again for joining. Rosie, I came to know you through Indie Hackers. You've been a community leader, very visible, very prominent online for a little while now. Where did you kind of start becoming a community builder and how did you end up kind of here sitting with us today?

Rosie: I'll try to be brief, as brief as necessary. I've been living in Brighton, I guess, for around 20 years now. I started out my career in tech as a software tester in Brighton. And as part of the kind of living in Brighton and kind of being a tester, I participated, I guess, in the local community, the local tech community, this is kind of going back to late 2005-ish probably. And there were lots of, kind of like meetups happening, a local conference. And I was like, "Oh, this is cool." I was hanging out. And then I decided to kind of start my own meetup. I guess that was my first step into community building. I didn't really see it as community building at the time. I ran a meetup for a couple of years, it was a girl geek dinner meet up. And it was just a lot of fun. And every month we did it like a monthly thing, we'd just like gather around, have dinner, have a speaker. And I just met lots of great people and it filled up like every month. It was always overbooked.

And that was just such a kind of confidence boost for me, I guess. Never having done that, I'm really quite kind of introverted and would never get up in front of people at the front of the room, but here I was gathering people. I was like, "Whoa, this is fun." And then I guess that led on to other things. And I kind of learned about Seth Godin. I started learning about communities and I was like, "Oh, this looks really fun. I want to do this more than I want to do testing. How can I do more community building and less testing?" Two things kind of happened at the same time. One, I started an online community for software testers because I felt like testers needed that and there wasn't really much out there. And also around the same time leading on from the meetups I ended, I kind of co-founded a coworking space as well. So I did those both kind of at the same time. And as you know, Tony, that was, I guess, fairly early on in the coworking era.

I wasn't quite there first, but it's like, there's not a lot going on. That was so much fun as well. I have such good memories from those days. I did the coworking space for a couple of years. It didn't work out due to business relationships, which is fine. So I just walked away from it. It felt like the right thing to do is just walk away from a kind of stressful situation, but like Ministry of Testing, which was the testing community that I founded, that I kept that going. And that had kind of slowly built up over two or three years and then come year three, I decided to kind of turn it into a business, kind of bootstrapped or indie business as I would refer to it now, and managed to turn it into a profitable business over the course of a few years. Yeah.

We hit kind of like 1.5 million in revenue at its peak just before COVID and entirely bootstrapped founded by myself and over the years kind of, I brought my husband on board to help me do some tech for it, build up a platform as it kind of grew. Yeah. I stepped back from that about two and a half years ago, mostly because I kind of lost interest in the testing world and I didn't feel like it was the right thing for me to lead a community when I wasn't truly passionate about testing anymore. And then I spent a couple of years at Indie Hackers leading their community before coming on board to Orbit.

Tony: I always have much love for my fellow former coworking space owners, as there's just a gathering energy to some of us, especially the early folks. And want to point out, you mentioned being an introvert and I feel like we're tracking this theory that introverts actually make for terrific community leaders in certain contexts. So we might dig into that some more, but I would love to touch on one of the last things you just talked about, which is this idea of kind of leadership transition and how you go about doing that. It sounds like, stop me if I'm wrong, but you said that you realized that you really love being a community leader, working in community, but that also you, you kind of wanted to step back from running the Ministry of Testing. Have you felt burnt out at all or do you still feel that incredible kind of sense of exhilaration of being a community leader or does it kind of ebb and flow?

Rosie: I think it probably ebbs and flows. I've spoken before to quite a few people about handing over the community so to speak. And a lot of people are really surprised that I've actually managed to do it because it's tough. And I tried a few times to hand it over and I think that the hardest part for me is when, for people who start businesses and it's making money, from the outside, everything looks great. But from the inside, if you don't want to do it anymore, you kind of feel trapped. When you want to do the best for the community, like for me, it was a really great community that I had started. The vibe was great. I had changed people's lives, and I had made friends. I didn't want to sell it because I knew that if I sold it, then yes, I'd probably get a bunch of money, but it would probably die.

And I knew that in my heart. But then at the same time, it's like, okay, but how do I transition it over to someone else? And how do I find someone who I trust enough and how do I do that in a way that I feel comfortable? And that was tough because literally the transition process was two years.

Tony: Oh my goodness.

Rosie: I guess the beginning of it was, I started working with Richard. We were building trust. He wasn't necessarily coming on board to take over at that point. It was more like a, let's see if we can work together and we like working together. And then as that built up, I guess, maybe after a year or so, I was like, "Okay, I think you should take it over. Let's try to make this work." And then it was a whole other year, at least, probably a bit more, of actually teaching him everything that I knew about the community so that he could take over. I felt trapped throughout that whole period. It was probably more like three years, to be honest. I really wanted to leave, but I felt like I couldn't leave and I had this obligation to keep it going and keep positive around everything despite just wanting to move on to something else.

Tony: How did you find the right person? And you clearly spent the time you needed to spend to ensure that you had the right person, but how did it initially come about that this effort was going to be put in between the two of you?

Rosie: I had tried a couple of times to work with people collaboratively and it kind of failed. The intentions were wrong and people just were doing it more for the money than the actual community. With Richard it was, he was a community member at heart and he loved testing. We held conferences, for example, he had his first speaking gig at my conference. The first time he got up on stage was at Ministry of Testing. And he kind of grew up there over, I guess, two or three years. He was disillusioned with testing when he started. And as he discovered the testing community, he kind of got reinspired. He kind of felt the connection with the testing world. And we kind of joked as we were working together, it's like one of the first things we did together is he helped me run a conference in his hometown. He used to joke about taking over the testing world is, “if we don't do something together, I'm just going to have to run you over” kind of thing.

At the end of the day, it must have came down to us working together. So it was first he helped me run a conference. So we collaborated on that and I showed him how I ran a conference. And then after that, he just started taking on more and more responsibility and it was kind of proving his worth. And he was coming to me with ideas or coming to me with solutions and just looking to take more and more off my plate. And that's really how it developed over the first year is that trust building. He was able and capable to do it. And I guess he really had the right motivations behind it all, which is probably the hardest thing to find with people.

Tony: That's true. But it did sound like you put a fair bit of work into identifying the qualities of the person that you would want to find for that role. And I think somebody having an enduring passion for the subject matter certainly makes a huge difference. And by the way, shouts for such a great niche. What a fabulous, specific niche.

Rosie: Yeah. I mean, lots of people when they first hear my story, they're like, "What? A community for testers, how is that even possible?" And yet a profitable community for testers, which is probably even harder. It's just hard to make communities work financially.

Tony: So as we kind of trace out to kind of where you are today, can you tell us a little bit about your work with Orbit and just kind of how your experience up to this point informs how you work with other community leaders and how you do that work?

Rosie: So, after Ministry of Testing, I went to Indie Hackers. At that point, I kind of knew, or I decided that I wanted to focus in on community as like a specialism and people in the testing world knew me. Everyone knew me in the testing world, but when I went to Indie Hackers, no one really knew me. Me being at Indie Hackers was also a bit of a test for myself, whether I could maintain the interest in community building, whether I could help build another community. Whilst I was in Indie Hackers, I started writing about community building. I did that, or I'm doing that, Rosie.land. That kind of started initially like as a newsletter and then a paid newsletter and now more of kind of a community around community building. I guess, when I started that, I was like, in my head, I had spent 10 years building up Ministry of Testing. I had my own experiences and my ways of doing things, and I guess my successes.

And I just felt like when I started exploring the community, well, no one was really talking about lots of experiences that I had gone through or the ways I was trying to do things. To me, it was just shouting out that there's something here. For me, it was like, community is everything. There's such a lack of information on it. And I guess for me, it was like, "This is what I want to do. Can I somehow build up this reputation for it? I really want to write about stuff. I really want to talk about this stuff and how can I do that?" So that became my focus with Rosie.land. As part of that, I started the, as I mentioned, a paid newsletter and that was my way of forcing myself to write. So it wasn't so much about the money. I had started a free newsletter from Substack. I tried for months to kind of write about community and I just never shipped anything. And I was shipping a weekly curated newsletter, which was a bunch of links, but I wasn't actually writing any of my thoughts.

One week, I was like, "Right. I've had enough. I'm just going to switch on the paid features of Substack and I'm going to start charging and I'm going to commit to writing something every week." And that was about a year ago actually, that I started that. And I've never written so much in my life so that's cool, stressful at times, definitely stressful. That led on to other things. My current boss subscribed to that newsletter and he invited me onto his podcast and we got chatting. We had a good chat. After I kind of accepted the job, I looked at my Substack stats and he was one of my best subscribers. He had read every post and stuff like that. So that was kind of funny.

I love Orbit, the team at Orbit and the way they're trying to think about community and it's kind of taken a new perspective and it's more data-driven, more kind of distributed and kind of more thinking in a way of how can we understand communities better so that we can use that data to build up better communities rather than I guess the more traditional sense is how can we get people to our platform and build community there. It's more like, how can we understand where people are and where they're having the conversations and work with them based on that. So I find that super, super interesting. Yeah, they've got the Orbit model, which is a framework around community building as well as a way to think about community.

Tony: I feel like having a framework is so valuable in a space. You said that there's just so much that needs to be discussed that isn't being put out there. And it's funny because I feel like maybe because of the bias of my own experience, that there's a lot of talk of community going on. For something like a framework for building a community, that could be hard to find. There's not a lot of great roadmaps for doing it sustainably and for doing it well in terms of really building meaningful relationships. That's great. Can you tell us a little bit about what that framework is, just kind of generally how that structured? Not to give away too much of the trade secret, but we'd just love to get kind of a sense of the philosophy behind it.

Rosie: The main framework is open source and freely available. It's called the Orbit model. I guess the way I think about it is that there's paths for community members. And often when we think of community, we say, we don't really go into the depth of understanding who our users are and where they're at. So the Orbit model has these different levels, level four, level three, level two, level one, and level four is the outer ring, the observers, and then each level — I should have this printed on my wall so I remember each level properly, but as you go to the inner ring, is that from observers, they can become participants and then in the center, they're more like your kind of advocates, the people who are shouting your brand, participating and speaking. So it kind of creates this kind of way to see how your members can get pulled in.

And then based on that, it's like, right. When you know that people are at these different levels, you treat them differently or you do different things with them. People who are on the outer ring, the observers, you're going to send them different messages or reach out to them in different ways than you would with your kind of main advocates. So like as a visual kind of representation, people find that really useful to think about. And then the software is kind of built with that in mind. It can get data on people who are at these different levels and the more they participate within your community and connect with your community, the levels basically kind of change based on various calculations that I don't really understand. So yeah. I mean, there's the idea behind that and then there's also this idea of gravity. But within communities, quite often people, I think, talk about like sales and marketing, but instead of using that kind of language, we use like, gravity is how can you pull people in?

How can you do things, create value, so that people are naturally, because they're excited or because they love what you do is not because of the sales and marketing messages. It's because you're doing things that are of value.

Tony: So Rosie, in terms of who uses this model and who Orbit works with, who do you work with? Who does Orbit apply this model for?

Rosie: So they're a relatively new startup. I'm not sure about names that I should or shouldn't mention. So it varies, big companies, small companies, indie creators use it to track their Twitter community, for example, all the way up to a larger software companies that are using it to track the bigger communities. And I guess being a new company or a new startup, there's lots of work to do, but there's probably, I think, at the latest count, I don't really keep track of it, but it was like 4,000, 5,000 people have signed up to use it and trying it out. The interesting part of it is it pulls in a lot of data, so it's really flexible in how you use it. And I guess part of the challenge or part of my job is helping people figure out how to use it to build better communities. And that's super interesting, but also a really broad thing for me to think about and try to tackle as community builder.

Jillian: Yeah. I'm looking at it. I signed up while we were talking and it seems like I'm almost overwhelmed with possibilities and correct me if I'm wrong, it's kind of like what I would call deep metrics. It really gets into a lot of the kind of analytical side of what's going on in the community. And then you can use that information and data to inform what to do. Is there any really common data sets or trends you're noticing in the communities you're working with?

Rosie: Definitely people using it to understand better the community analytics. It's really great for things like it creates a profile page of every user, so if someone participates through Twitter and Slack, then it creates a profile page for that. So you can start to track how they've come into the community. And I guess, if you're building a business, is that when they convert? How long does it take them to convert? For me, it's really interesting. I'm actually working, for example, with Ministry of Testing on figuring out, trying to help them figure out how to use it. And we've been diving into some of their use cases and just to see how community members sign up, how they engage and then how they convert as customers is so interesting to see. Because at the moment, there's no way for people to know that. It's like, yes, you know you've got Twitter followers. You know you've got people on Slack or Discord, but you can't hook that information up easily.

Jillian: It's almost like a deeper level into the psychology of it that, like you're saying, we've never really been able to see before. So yeah, I'm sure y'all are going to be publishing all sorts of just really powerful findings from this that will help inform other businesses on how to convert and engage.

Rosie: One of the things I've been doing is, or trying to encourage people to do, is instead of doing surveys, that is quite a typical thing for the companies to do or communities to do is, instead of doing that, is they ask them questions, whether it's on Twitter, on Discord or Slack. And when you're asking questions and people respond, then that pulls the answers into Orbit and it starts to build up a better picture of who your people are so that when you do go to have conversations with them at a later stage, there's that information there so that you can almost use that to hold a better conversation. And tactics like that I think are kind of super interesting. It's like, how can we really get to know our members really well? How can we learn to ask good questions that matter so that we can later then use that information for everyone's advantage and kind of in the most positive way as well?

Jillian: And that's interesting. So you're saying instead of just putting out a survey where people answer and you're not necessarily tracking who said what, which time kind of thing, you're able to collect that into their profile within Orbit. And so you could look and be like, "Oh, look, Tony, here's his answers the last three months and check it out." Are you also able to kind of collate different things? Like if this, then that, like who thinks this, this and this, but also isn't commenting. Can you deep dive on that level to sort people and just kind of see what's going on?

Rosie: Potentially. I've not gone that far yet.
Jillian: So say there's people building community that maybe aren't using Orbit yet, although I'm sure they're enticed with this, with this conversation, but are there some kind of basic best practices you've found based on your own experience in general as a community builder, but also with the data behind it, whether it's through Orbit or through anything?

Rosie: I guess at this stage, because I don't want to stick my foot in it, but things are still really early and the product is developing, but I think at this stage, a lot of it, a lot of my thinking is about how much data can you gather about your members and not necessarily just in an automated way, but it's like, how can we create better pictures around to who your people are so that you can then, when the time is right, you can then take action easily or more efficiently?
So, as an example, it's like if you run an event, that's one bit of data that you can start tracking is that this person attended this event. And over time you might be able to see trends like, "Well, this person has attended 10 events. Oh, this is like someone coming into Orbit one," but then you can also do other things, like one thing that I do is put myself out there and I just have community conversations with people.

And every time I have a community conversation, I kind of take notes and I add it to Orbit so that, whether it's me or someone else from the team, that they'll see that history there. Some of the data's kind of automated. Some of it's manual. So, and what's the goal of really what I'm trying to do is understand who our people are so that we can serve them better. You can't rely on your brain to do that. So how can we mix and match kind of good human tactics alongside, I guess, more automated options? So let's say the more data you collect, the easier it will be to reach out to these people. So say if the people have attended five events and you want to reach out to only people who have attended five events or more, then it becomes really easy to kind of export that data and email them all, and you can start to segment people pretty easily. I guess, as a mindset, it's like really trying to dig down into that and seeing value in maintaining data on people.

Jillian: What kind of questions are you asking, just out of curiosity? What are some common questions you would send out to the community?

Rosie: Oh, I did this at Indie Hackers a lot, but never fed into Orbit. At Indie Hackers, I ran the Twitter account for a year or so. I used to ask all sorts of questions from what you building to where are you in the world right now? What are your biggest challenges? I would quite often, discussions and forum posts on Indie Hackers, I would post them onto Twitter as well.

Tony: You use the phrase monthly recurring relationships online. You want to tell us a bit about kind of the provocation behind that?

Rosie: It was through like Arvid Kahl. He tweeted something about monthly MRR and like friendship or something like that. It just came to me. It's like, it's this monthly recurring relationships. Instead of the revenue, it's relationships, and then like, yeah, I added that as a comment. And then I was like, "Oh, this is interesting." So I wrote another tweet saying, on its own a few days later, it's like, "MRR is monthly recurring relationships." And then like, I took it a bit further thinking, "All right. If monthly recurring relationships was a community metric, what would it look like?" I haven't developed specific thoughts about that yet. These are the types of questions I put out there to get ideas and feedback from the community. But monthly recurring relationships, I think, is kind of potentially a super interesting metric that we could create.

Jillian: Oh, that's the most genius metric I've ever heard of because that is community right there.

Rosie: That's what we should be doing as community builders, is keeping in contact with people every month and how can you do that? And how can you measure that? Should we even measure it? Or how can you use software, Orbit, or whatever you want to use, to keep in touch with people and keep those going every month? Not necessarily just email blasting people, but genuine conversations. How can you scale that? How can you do it in a human way?

Jillian: I know. Well, yeah. Even just thinking about just each different community, it might be — it's so individual. Our community is on a dedicated platform that's private and so would it be some sort of engagement metric there and what is the threshold? Is it someone who in versus comments versus makes a unique post? Yeah. So many things versus, like you're saying, if it's a more in-public community, like on Twitter, is it a like, is it a response or retweet or all of the above, but I think you're onto something that I'm totally now, just my brains in like a spin of like, Ooh.

Rosie: And you can give value to different activities as well. And Orbit kind of caters towards that. So someone speaking at an event that has a higher points mark than a like on a tweet, for example.

Jillian: Totally. Both you and I are like, "Whoo."

Rosie: Just to add to that, as I think this kind of stuff is important to me as a way to rethink what communities are and how we can build communities. So that really a lot of the reason I'm here now, not here on this podcast, but here doing community stuff is I want to explore how to build better communities. And the more I think about it and the more I write, the more I tweet, these new things kind of come up and I think that's pretty exciting. I think there's a lot of work that everybody could do to contribute to building better communities.

Jillian: Absolutely. I think there's something so valuable about being curious and staying curious. So even though you've successfully built community before, you have that under your belt, you're not just leaning on that. You're still thinking about things and being analytical and trying to figure out even better ways. And I think the more of us that do that and talk about it, the better for all of us, because then we can learn from each other, get these awesome acronyms that mean something even cooler than what we used to know it as, and keep on building.

Tony: I want to ask you, Rosie, your perspective on the role of questions. You had said that the questions you ask may be more important than the commentary you make. And I noticed that you pretty regularly post provocative open-ended questions about how do you know when there is a community or how do you maintain energy as a community leader? And I feel like creating the space for people to answer those questions gives us a way to get to know each other better and get to know ourselves better, explore this topic, but it's got to be super valuable to you as well. Have you found that to be super valuable?

Rosie: Yeah. I keep meaning to collect all my questions that I've ever asked and dump it into something special. So that's on my to do list that I need to find the time to do. I think questions are super valuable. I like to say they give the people the opportunity to participate and that's one reason behind it. Another reason is really believing in people that other people have their own world views and their own experiences. And they can come in with super valuable responses that we can all learn from. Another way is connecting. It's a way to connect people. I'm pretty convinced that the questions that I put out, people have connected over them and definitely made friends because of that. And I guess there's a couple of other points. One, I think questions can be hugely educational tools within themselves.

They don't necessarily need answers, but just the mere act of asking the question makes people think about the answer and come up with their own response that's — even if it's just in their own head, they come up with their own kind of response that is relevant to them. And then it comes back to also, I guess the idea of sometimes we think other people hold the answers. And I like to show people that, actually, I don't know the answers. And I think too many people like to kind of come across as experts or gurus and almost forcefully lead people down the wrong path. And I just feel like if you're a leading a space and you're open to asking these questions and appreciating the responses as well, it shows people that we're all here learning and we can all kind of figure stuff out together.

Jillian: That is so true. Collaboration will always produce better efforts than individual thinking, but I really want to just circle back and touch on something you said that just like sparks joy in my soul, which is the importance of seeing different perspectives, especially — we're so fortunate with technology to have this global community that not too long ago wasn't possible. And so we're able to get so many different people's life experiences and belief systems in one room, and if we're willing to just be open and meet people where they are, we can learn so much from each other. And also just something we talk about a lot on our team with our community is just about meeting people where they are, but also being open to different perspectives and learning from that. It's just huge. So I'm glad you brought that up.

Tony: All right. I think we're up to that time. Jillian, do you want to lead us through the — I keep calling it the lightning round, but that's not what we call it.

Jillian: Well, we can call it the lightning round. The hot seat?

Tony: The hot seat.

Jillian: I think we call it both.

Tony: The hot seat lightning round of doom.

Jillian: The hot seat lightning round with Poppy in the background barking.

Rosie: You could call it the Rosie round.

Jillian: The Rosie round.

Rosie: For this edition.

Jillian: All right. The Rosie round has commenced. Rosie, when you were a kid, what did you want to be when you grew up?

Rosie: I had no idea. Absolutely zero idea.

Tony: Love it.

Jillian: Never know like, Ooh, that's fair. I like that you lived in the moment. You just enjoyed your childhood. How do you define community?

Rosie: I try not to, but if I have to, I would say it's about people coming together over something they have in common, common interests, I guess.

Jillian: It's such a hard question for community builders. Isn't it? It's like, how do you not define it?

Tony: I think the answer “I try not to” is a really good answer.

Jillian: Probably the best answer. Yeah. Okay. Rosie, what is something that is on your bucket list for your life that you have done?

Rosie: That I have done. I unschool my kids.

Jillian: What is unschool? Tell us a little bit of more about what that is.

Rosie: I don't send them to school and we, me and my husband, raise them together and we juggle everything together and there's no curriculum, but we kind of work with each child to figure out what they need. I've got five kids.

Jillian: Wow. That sounds like a lot, just, well, five in general, I have one and I can't even imagine, but then yeah, with the unschooling you must have wonderful relationships.

Rosie: Yes. It's not perfect. I've got one son who's on the spectrum as well. So obviously it brings its challenges. I may have others on the spectrum as well as we've been through my oldest now. But yeah, I mean, I wouldn't change it for the world and yeah, they're the aged between three and 17 at the moment. But yeah, my two oldest went to school for a while. My three youngest haven't and there's definitely an extra bit of innocence on my three youngest ones.

Jillian: That's sweet. All right. And then what is something on your bucket list that you have not yet done, but you hope to in your lifetime?

Rosie: Probably take time off, a long bit of time off. I've not done that properly. I left home when I was 18 and I've just been on the go since, so I'm 42 now. So I should just take some time off.

Jillian: What is a book that you just are currently just really loving or just one of your all time favorites?

Rosie: Good question. I'm reading Rob Fitzpatrick's book. I honestly haven't read a lot of books recently because life, but I'm keen to write a book on community building and I like Rob Fitzpatrick's work, his was it writing useful books? That's probably not the exact title, but I like his way of thinking. And I'll probably write a book based on his advice soon.

Jillian: Oh, well, keep us posted on that because that's obviously up our alley.

Rosie: I guess that's on my bucket list is writing a book.

Jillian: Yeah. I like that. You could almost combine those, like do it like a sabbatical, just casually write a book while you're on it. Maybe then it's not really a holiday. Okay. So you mentioned before you live in Brighton in the UK. If you could live anywhere else in the world, where would that be?

Rosie: I wouldn't move. We tried moving once and we came back and I think when you move away, you realize what you have. We're very happy here. We've been in Brighton mostly apart from the time we went away for 18 months for over 20 years. And when you have kids is actually gets really complicated to move and like the friendships they have. So we're in the process of renovating our house right now and the house will be amazing. So it's like, I can't.

Jillian: You're set.

Rosie: Yeah, we're set. This is our house. We're going to stay here forever.

Jillian: What was the thing when you moved that you missed most about Brighton? What pulled you back the most?

Rosie: Brighton's a youngish kind of city. It's kind of like, I guess, trendy. I don't feel so trendy anymore when I been here 20 years. I definitely don't go to the town center as much anymore, but I guess part of it is being by the sea and having those sea views. And I go running along the seafront.

Jillian: That sounds lovely. Most of my point of reference for Brighton is Jane Austen novels. So I'd love to someday actually see it for sure. It just makes me think of sea bathing. Okay. And final question. How do you want to be remembered?

Rosie: Oh, good question. Oh. I want to be remembered as someone who who's done the right thing, who always tries to do the right thing. And I think that goes through everything I do is I never do anything for the money, though I know money is important, especially as a founder, not so much founder now, more employee, but I still. Even as an employee, I'm not even doing it for the job or I'm doing it because I want to do it and I'm always trying to do the right thing. So I hope that people notice that.

Jillian: I love that answer. I hope people are inspired by that to do the same.

Rosie: Thank you.

Jillian: All right. You passed the Rosie round. You did it. With flying colors. Rosie, where should people find you? It sounds like Twitter, for sure.

Rosie: Yeah, definitely Twitter, @RosieSherry on Twitter, Rosie.land for my writing stuff, and Orbit.love is where I work at the moment.

Jillian: Excellent. Well, it has been such a pleasure. Tony, any parting thoughts?

Tony: No, I'm just so glad to have you along, Rosie, excited to continue following your amazing story, being inspired by your provocative sharings and questions on Twitter and keep up the amazing work.

Rosie: Thank you.

Tony: Rosie Sherry, everybody.

Rosie: So great.

Tony: She's great. And such a pleasure to just hang with. I feel like my own blood pressure went down, just sitting here, hanging out, chatting with her, which I think is such a great attribute for a community leader.

Jillian: Yeah. She has a super chill vibe, which I appreciate because you can just talk, although, for people listening, we're on video and we talk and her eyes definitely lit right up when we got into interrelationships and approaching how you approach like managing monthly relationships and whatnot. There was some magic happening. It was great. But yeah, there was so much there. She's had such a journey.

Tony: Yeah. One of the first things we started on, which is kind of weird, because it's about endings is the exit strategy, which can be such an elusive thing for a community leader.

Jillian: Honestly, I don't know if I've heard that strategy before. And I think it goes a lot into how much she cared about the community she built, even though she was feeling burnt out and didn't really necessarily want to manage it anymore and put all that love into it. The fact that she really thought about it and then identified somebody who was so active and then really curated that relationship and handed it off in such a slow roll, but in a way that it maintained itself beautifully across that transfer of power, I guess, for lack of a better term.

Tony: Yeah. It's healthy to have that in mind, regardless, is to be thinking about who's in that position where they could be helping lead things, regardless of if you ever have any intention of having somebody else take over and run the show because you may not know where things are going to go.

Jillian: Yeah, I think there's just really something to say about planning for an exit, so even if it's not, if it's something you're mulling over and also just in general to have standard operating procedures, what to do in situations, just documenting how you run a community is super valuable, even if you don't plan on leaving, but also super valuable if you do plan on handing it off and stepping down. Communities, I think, don't love change, don't love big changes. They get used to things the way they are. So anything you can do to make the changes less obvious to the people in your community the better.

Tony: Rosie used the word trapped multiple times and anybody who's run a community for long enough can probably resonate with that feeling. And the truth is there's a number of ways that a person exits leadership of a community and a good number of those ways involve the community not being around anymore. That could be okay in certain contexts, but the point is if you make the decision to kind of undertake the journey of being a community leader, it's important as early as possible to just have that in your mind to be thinking about what's kind of the graceful way that I can eventually be stepping away from leadership and how can I be laying the foundation for new leadership to be emerging, which doesn't guarantee that it will emerge. I've tried to find that succession leadership in communities I've run and I failed at it at times. So it's not always a guarantee, but certainly keeping your eyes open for it can help give you some better options down the line.

And part of that is, in my mind, what the Orbit model tries to get a handle on, which is these — I'm calling them concentric circles — concentric circles of participation in a community, recognizing that there are some people who are going to be on the periphery, who might subscribe to your newsletter or follow you on social media, but they might be very quiet. And then there are people who are maybe going to be more participatory, showing up at your event programming, engaging with you, maybe they're a customer. And then there are the people who are kind of the super members. And by the way, this isn't the Orbit model. This is just my kind of take on the idea that there are these different levels. So for the proper Orbit model, go check it out on their site. But the idea that understanding what the different gradations are of the levels of participation in your community and then making it easy for people to kind of fit into those categories.

So if you know that people are at these different levels, you can design different kinds of experiences for each of those levels, make sure that you've got a good community experience at each of those levels. And you want to try to make it as easy and smooth as possible for people to transition between those levels both further in and further out.

Jillian: Yeah, there's so many different types of community members and it's certainly a value to spend some time people in the outer rings of the circle, if you will, trying to get them more engaged and more invested in your community, and you can't really do that until you identify where they are. So being able to do that, whether it's with a tool like Orbit's or your own, looking at your own metrics and engagement data, looking at that, as you try things with different people in those outer circles, it will help inform what works.

Tony: I also want to bring up, as a takeaway, the language of monthly recurring relationships and just that little nudge of thinking in terms of not just monthly recurring revenue, but maybe that delicious form of currency that just can't quite be measured in dollars, but is so indelible and so powerful.

Jillian: It is, though. I think it's so important. Obviously revenue is the bottom line. It's going to play a role. And even what Rosie was saying at the end in the Rosie round about it's not about money, it's about doing what you love. I think it's all similar, like, yeah, money's a part of it, but. And if you're cultivating your monthly recurring relationships, you're ultimately improving your revenue as well.

Tony: Yeah. Anybody who is building relationships, especially ones that are, I guess, recurring ones, ones that grow over time, is going to be in a great position to build a thriving business. That's a big part of, I think, the hypothesis behind why we talk about community from a business perspective and a lot of what we do, because good community is good business.

Jillian: Honestly though, even outside of business, I think just like human relationships, it kind of got me thinking like, even just friendships, if you want to say, like, I want to commit to talking and whatever that means be it text or actual phone call or in person, investing in your personal relationships. So, you know what? I haven't talked to my friend Lindsay in a while, even though we live near each other, just COVID and whatnot, I'm going to see if she wants to get together for some hot tea maybe later this week, maybe an Earl Grey, maybe a chai.

Tony: Lindsay can't wait to hear from you, Jillian.

Jillian: But it's like, whoa, I haven't been investing in that relationship lately. We've both been busy, but I'm going to take a minute. I think it's a lovely analogy.

Tony: All right, y'all. Thanks for joining. Keep doing everything you could do to make the world a more belongful place in your neighborhood, in yourself and the people you know. Keep gathering, keep doing good things to make people less lonely and keep being awesome.

Jillian: Yeah. This has been The Community Experience. We'll see you next Tuesday.

Tony: Bye. This has been The Community Experience. For more information on this episode, including links and show notes, head to SmartPassiveIncome.com/listen. To find more about Rosie Sherry, you can head over to Rosie.land, R-O-S-I-E dot L-A-N-D. And you can find her on Twitter with her wonderful provocations Twitter.com/rosiesherry, S-H-E-R-R-Y. And Orbit can be found at Orbit.love.

Jillian: Your hosts are me, Jillian Benbow, and Tony Bacigalupo. The Community Experience is a production of SPI Media.

Tony: Our executive producer is Matt Gartland. Our series producers are David Grabowski and senior producer Sarah Jane Hess. Editing and sound designed by Duncan Brown. Music by David Grabowski.

Jillian: See you next time.