Building Profitable Communities with Rosie Sherry

Reading Time: 33 minutes

Today, I am talking to Rosie Sherry, proprietor of Rosieland and community empowerment expert.

One thing that I’ve always found fascinating about Rosie is that she’s a big believer in Unschooling, the kind of homeschooling that isn’t based on a set curriculum but on a guided form of letting your children follow their interests. Coming from Germany, where they’ll take away your kids if you remove them from school, this is incredibly interesting to me. So that’s what I opened my interview with. Rosie has a really down-to-earth approach to preparing her kids for adulthood, which involves some of her five kids teaching the others. She also regularly shuttles them to the library, where they can pick out whatever they want to learn about next.

This is incredibly kind and empowering, allowing her kids to learn at their own pace with minimal external interference — yet still receiving instruction and guidance from within their peer group. One thing that stood out to me is how Rosie understands the value of a community, of any size

Now, let’s dive right into the conversation — I unfortunately hit the record button a bit late. We start mid-converation. Here’s Rosie, starting off the conversation by talking about why her kids didn’t enjoy regular school, and how that impacted how she educates them.

Topics

00:00:00 Introduction
00:01:48 Unschooling
00:06:47 Avoiding stress & disharmony
00:11:47 Dealing with negativity in communities
00:16:34 Why you don’t want ads in your community.
00:20:14 Why you can’t just start with “community”
00:27:27 The audio medium and its impact
00:33:19 Pointless community tools
00:40:58 The IndieHackers community
00:45:27 Trust your own vision
00:51:31 Community and family

Arvid Kahl  0:00  

Hello everyone and welcome to The Bootstrapped Founder Podcast. Today, I’m talking to Rosie Sherry, proprietor of Rosieland and community empowerment expert. Now, I messed this one up a little. Rosie and I were talking for 10 minutes already when I noticed that I had forgot to hit the record button. 

Well, since I’m all about building in public, this means sharing the mistakes that we make as well. And this is a pretty big one. So oops, sorry about that. Let me summarize this for you. So you can imagine this 10 minute conversation. One thing that I’ve always found fascinating about Rosie is that she’s a big believer in unschooling, the kind of homeschooling that isn’t based on a set curriculum like regular school, but on a guided form of letting your children follow their interests.

Coming from Germany, where they will take away your kids if you remove them from school for a couple of days, this is incredibly interesting to me. So that’s what I opened my interview with. Rosie has a really down to earth approach to preparing her kids for adulthood, which involves some of her five kids teaching the others in the subject that they’re interested in. And she also regularly shuttles them to the library where they can pick up whatever they want to learn about next. 

This is incredibly kind, and empowering, allowing her kids to learn at their own pace with minimal external interference, and yet still receiving instruction and guidance from within their peer group. So kind of points at something because one thing that stood out to me is how Rosie has understood the value of community of any size. We will talk about this a lot in the part of the conversation that I actually did record. Now let’s dive right into the conversation. Because that’s the best we can do at this point. Here’s Rosie talking about why her kids didn’t enjoy regular school, and how that impacted how she educates them.

Rosie Sherry  1:48  

My eldest was at school, he wasn’t enjoying it. He was complaining about like kids being too loud when it was supposed to be like quiet reading time. And then we went to like a teacher meeting. And we got to see their work, their workbooks. And like, he was obviously bored because he had been doodling like in the pages. Say, “Oh, cool. That’s like a great drawing.” And then like, there was this big fat red mark from the teacher saying, you know, like, basically like turning him off for doodling, “you shouldn’t be doing this” and then wrote on “lacks concentrations.” 

And that was kind of like the turning point for me. We’re like, “Do we really wanna do this?” This is the reality of what school is. And basically, shortly after that, we asked him and said, “Do you wanna stop going to school?” He was just like, “Yes, completely 100%. Yes.” 

So we took him out first, and then I don’t know. Like, three months later, we took all this now, try not to do it all at once, kind of trying to test the waters, see how we feel. And the rest is history. But like my three younger ones haven’t really been to school. Though, they’ll trade the private walled off, like part time. It lasted a term. Like, “No, we don’t wanna do this. This is not fun.” Alright, come here.

Arvid Kahl  3:16  

That’s interesting, because I know several people who went to a Waldorf schools and they found enjoyment, even though there was structure. It was a different kind of structure, that they were more compatible with than regular school. But they were in regular school before. So they had something to compare it to, think that might make a lot of difference too, right?

Rosie Sherry  3:34  

Yeah, I think so. I think that they just used to like, probably just not spending any time on things that they don’t like to do. 

Arvid Kahl

Yeah

Rosie Sherry

And some people will say, “Oh, well, you should force him to do stuff they don’t like.” I’m like, “Nah, I don’t.”

Arvid Kahl  3:46  

Yeah, that sounds a lot like it happened to me, so it has to happen to you kind of thinking, right? This kinda forward, pushing forward this tradition of indoctrination. Yeah, that is my experience. That’s where I come from, right? In East Germany, in particular, there was a pretty hierarchical, very top down school system. And nobody was allowed to question it. Nobody did question because it was also politically entwined. So that was that whole level too. I remember it exceeded the basic initial couple years of schooling too. It went all the way into academia. 

My grandmother, she lived her professional life throughout the existence of the East German socialist state. And even when you studied, like, the highly intellectual topics beyond politics, like Economics or Sciences, all these things. And she was an economist. You had to always look at it in the context of the Marxist Leninist political perspective. Like that was part of that system. And she was not too much into that. She just wanted to do Economics. Like I’m grateful for that, not having this kind of political stuff in my family because I was born in 85, so I only got like four years of that whole thing. But she always told me that if you didn’t comply with that, you had no career. 

And I feel school is, if you don’t comply with the disciplinary structure, you don’t have success later on with your grade point averages and all this kind of things. And what I wonder about unschooling is like, how does it match up with these kinds of market expectations of grades of these accolades, or these compatibility charts, which are kind of these great sheets? That’s how I see them. How do you deal with the fact that, when you have kids in the system or not in the system that want to join the larger market later? How do you prepare them for that?

Rosie Sherry  5:55  

None of our kids are in the market, yet. So I don’t quite have experience getting there. But like, I have no qualifications, right? I’ve been on my own since I was 18. And I made my way. My kids have it off better than I did, you know. They have luxuries I wish I had, you know. They have the safety of a home and they’re not gonna get kicked out. 

Arvid Kahl  6:22  

It sounds very much like the Indie Hacker spirit, right? That’s kind of what it is like, we’ll figure it out. If there’s a challenge, we’ll meet it along the way. Yet, it’s interesting. 

Rosie Sherry  6:31  

It’s smart, that’s really smart, right? Since like, I want them to focus on what they wanted. But at the same time, they’re not scared of working. But one of them wants to get a job at some point soon. And I think he will, like, not right now. So it’s like, you know “good.” I think my philosophy is basically, if it causes stress, and disharmony to like, push my kids towards doing something, then I kind of back off and just like give it space and let things kind of see what razors are, pretty relaxed.

Arvid Kahl  7:06  

That is a very interesting segue into what I also wanna talk to you about, which is community building. Because that sounds like a paradigm. That sounds like if it’s harmful, if it’s stressful, then it shouldn’t be done. Do you also translate that into how you approach building and maintaining communities?

Rosie Sherry  7:23  

Yeah, probably. It’s all interrelated. Indie Hacker, unschooling, it’s all the same thing. I think, you know, the foundations of it is that you wanna be surrounded by good people. You wanna do good things. You want to tap into people’s talents. You wanna support them. You wanna find problems to solutions. This whole like, yeah, it’s all one big same thing pile of philosophy of life, I guess.

Arvid Kahl  7:50  

It’s an empowerment move, right? Like, I think building a business is empowering people to do something better. Like teaching children is empowering them to do things on their own. And running a community is empowering people to find other people who wanna hang out with each other and help each other, like exchange information. I love that. What a positive and open and friendly approach to just doing things with and for other people. I really enjoy that. And with that, I do have to ask you, because, you know, you run Rosieland, which sounds like the most magical wonderful place. I would like to know more about it because that’s just you know, it’s just such a nice and friendly and person centric space. So, what is that and why is it? What is it for?

Rosie Sherry  8:41  

Oh, and sake and where do I start? Rosieland is, it was just meant to be a blog and a newsletter. So when I stepped back from Ministry of Testing, I was looking to focus more on community and part of that was like, “Oh, I had this opportunity to lead the community Indie Hackers of the Arctic that and like, you know, teach me how other communities are run, there’ll be good learning experience. And I basically are surrounded by Indie Hackers, which are kind of like my people, I guess. 

But I was like, I want to write about community but I had never had the chance to actually specifically like write about community blogging. I had my head down with Ministry of Testing, like doing stuff rather than writing or creating. And I prefer the term Rosieland for years. This is like just something that I’ve used, what my husband has used, you know. When my husband like looks at me, is that I’m off, like focused on something. I don’t reply, he’d say, “Oh, she’s off in Rosieland.” So, that’s basically, I’m off in my head. And I was thinking, I was trying to think of a name to call my website, my blog domain. But then he ended up coming to me and said, “Rosie, you know that rosie.land is the domain, you should grab it.” 

“Oh my God, that’s like, so perfect.” So I grabbed it. And that was, I guess the start of it. But I started late with the kind of curated newsletter. And then slowly, each, I guess three months, I would like level up a bit and say, “Right, I can do that. I’ve got my flow for that. Now I’m gonna like, turn it into page newsletter, and then started my day job.” And I kept that going, but not as well as I should have. 

But over time, is that I still ship like article, new article every week and a weekly newsletter. So two things a week. Basically, for the past, I don’t know two and a half years. And I’ve never done that before. I’ve taken some breaks, but like not many, like Christmas. And I took a break in August. But basically consistently writing like I’ve never seen before. So now, it’s more of a community now. So now I’ve like, busy since I left my last job. I kind of, I restarted it all from scratch, and scrapped everything and just like rebuilt everything in ghost. And I’ve been told that and finally, it’s like, you know, think, what’s the right word? It’s going well, at the moment, I think. I feel very, very happy, like, what was with where I am at the moment.

Arvid Kahl  11:47  

I’m glad to hear it. And I think like it’s one of these things where you, when you write about the thing you do, and the thing you do then attracts more people into this group that want to learn about the thing you do, and you write about it for them. It’s just this nice, self fulfilling kind of loop, right? It’s self feeding loop, the feedback you get from within the community makes the content for the community better. And vice versa. I really like to hear about it. 

And I love when you share things for like from the community, how the community is doing. You also have a really nice Twitter presence, sharing your knowledge for free on Twitter, which then attracts more people into this mind space, even of sharing knowledge and building community. I love that is, you say, it’s a newsletter/blog/community that you’re doing all of these together? I guess the independence is in there as well or is that a distinct project? How do you see that? And what is it, maybe for those who are listening?

Rosie Sherry  12:41  

The Independent is fit that’s indie and independent, like, you know, not, I guess, to the indie founders out there, the Indie Hackers. I guess that’s for me, like, partly, I feel like I have a lot to give in that world as well. And it’s not part of rosewood and it’s just something separate. So I have a little slack community. And I recently started substep cord, so I could write there as well. And I kind of decided recently that like Fridays are my independent days where I’ll kind of like thrash out a post every week. Every I think that gives me like a nice break from Rosieland just to like, do something different, almost any shape assessment work on a different project, different kind of energy, I guess.

Arvid Kahl  13:32  

Yeah, that’s one of the things I was thinking about in mentally preparing for a conversation today was that any community that I’ve ever been part of, particularly when I had to manage it, and most of these were World of Warcraft guild, so let’s, you know, keep that event like in the background here. I at some point grew tired of the, you know, the politics, the bickering, and all these little things that can happen in communities. And you like pulling yourself out of it for a day a week and doing something else that probably is already enough to kind of reestablish this baseline of enjoyment of the actual community. But how do you deal with these things? These kinds of any community has negative things, that things that shouldn’t happen or things you have to police and how do you do that within your own communities?

Rosie Sherry  14:17  

Honestly, I don’t want that at all. I think there’s this natural assumption that you have to deal with that kind of stuff but the community I have is that I mean, I wrote something about this as like a career it is not necessarily a free for all for anyone to post do what they like setting up a culture while in advance and living that culture executing on it. Influences who shows up. You know, even though like I’m quite active on social and people know me and all that kind of stuff. I don’t really do a lot for put for growth for my communities. I don’t reach out a lot. I don’t say, you know, try to pull people in when they’re not ready to call in. I kind of just have this philosophy is like, whoever’s gonna show up, that’s who needs to be here and they’ll fight, they’ll find me when we’re here. 

And I think there’s a natural consequence that just attracts the right kind of people who don’t misbehave. I love them. That’s so nice. And it’s also just like cutting down pretty quickly on certain things that I don’t like. And one of them is self promotion. So my community exists in many different places. So I have a Twitter community, for example. 

And I make it very clear that no self promotion, someone posts anything that’s even remotely close to that I can move it in as quickly as I can. And not a lot. Not enough communities do that. I don’t think it’s like, they’re not designed to, I guess, look, I’m a bit and pitch and done it. But I’m like, I want to get stuff done. I want to change the industry. And so to get there, I feel like we need to focus on good conversations that actually help people and create some kind of impact.

Arvid Kahl  16:16  

Yeah, that sounds to me like most people misunderstand why communities exist when they go for this heavy self promotion stuff. And that’s kind of why Reddit has developed such a strong anti advertising policy. Most subreddits get banned immediately, if you even just post a link, doesn’t matter where it is, like doesn’t matter where it links to us. As soon as you pull people out of the community to go somewhere else. You’re an enemy of the community, in a sense, and I even though I often feel this is a bit too much, because you know, the internet is supposed to have content that is linked. 

I do understand that most people have a semi nefarious purpose in posting something they want people’s attention, people are trying to grab people’s attention out of these communities. So for like purpose driven communities or goal driven communities, I very much understand that you don’t want ads, you don’t want self promotion in there. That’s an interesting point. And what I heard was setting up a culture beforehand. And that feels hard. You know, because how you set up a culture without people already living the culture is Am I just misunderstanding this? Or is that a little secret that you’re using. How does it work?

Rosie Sherry  17:27  

I think it just starts with, yeah, I start with just being me and like, choosing to create the things that I want to see in the world. Rousselot and it’s like, obviously the sake, it wasn’t meant, meant to be creative. But like, some people look at the term that the name Rosieland. And they say, oh, no, that that name is like too personal to you. Then, like, I put out a tweet a few weeks back saying, you know, asking what businesses out there had the founders name and say there’s all these businesses that have its founders name. And I’ll say it right, that’s like zero excuse is a Rosie lander is roselands here to change community as arrogant as some people might think that is because it’s also my name. This whatever.

Arvid Kahl  18:20  

So weird to me too, because he’s such a humble person, right? It’s like it’s the exact opposite of what the megalomania kind of personality you would think. And yeah, if you have Walmart and you can go there and buy things that are not designed by Sam Walton right, then you can go to Rosa Linda learned about community, that’s fine. I very much agree. And I think it’s actually quite nice that you have something also it’s kind of a play on words, right? Like Rosie as an adjective. So it’s not really a selfish kind of connotation. I really like it. I love the name. And I love the visuals that you have with a to the little rainbow in the clouds. That’s why I said it’s a magical place. Like Rosie land is a magical place. 

Even in my mind, you have created something that I’m not even part of right like I know off Rosie, and but I’m not a not a part of your community and part of the Twitter community, not if you’re, you’re more encapsulated one, but I still know what it is. And I have a really, really good feeling about it. When I think about it. I think it did a great job with that. And one thing that really stands out to me with Rosina and in particular is that you didn’t start it as a community, but it grew into one. This is something that I’ve heard a couple times in the past. I think I talked to Danny of a seller recently and his small bets community also came out of him actually wanting to just do a cohort course. He didn’t want to grow community at all. He didn’t set out to build one. 

But the people in his course, they just naturally bonded and they wanted a place to keep communicating with each other and through the cohorts that little place grew into a more elaborate construct which turned into a community. So seeing that, that the best and apparently also the most have authentic communities come together in an almost an after the fact manner? Can you intentionally build a community? Or is that always something that comes from someplace else? What is your opinion on that?

Rosie Sherry  20:14  

And like rebel ministers testing, I started with a forum. So say I went kind of straight into community kind of, but the forum had a purpose as well, we were there to like, talk about stuff, you know, like, explore things. So, I think, yes, you can just start with community. But I think ultimately, most of the time, it doesn’t work. 

And because there’s all sorts of factors that you need to actually have a successful Variante. One of them is just like, brand recognition or trust, people need to have trust in you. Another one is just like, knowing that you’re tapping into a real problem. And that doesn’t necessarily come with Community First, it comes with, like exploration of ideas. So in most cases, like community is kind of like a byproduct of what you’re creating. 

And then people naturally gather around it. Much like kind of like a library, right? So it’s like, you can have, you know, libraries can form communities around them, or they can community spaces of people gather there. But they go there for the books, they don’t go there necessarily to like, you know, form community. And just like, that’s what ends up happening, because the library is the library has to come first. Usually, not always. I think there’s always situations that can break those rules. But the more I tried to think about creating, which is basically like, my goal at the moment is like, I don’t say, I just want to like figure out better ways to build crazy because like, people still don’t know. And I just think like, you gotta have like a real problem to solve. 

Arvid Kahl  22:01  

Awesome right? Good idea. Yeah. Usually,

Rosie Sherry  22:04  

otherwise, what’s the point? And so are these people like they start community, and they invite people into, like, empty spaces, they have no goal, they don’t know why they’re there. You know, what’s the point of showing up with people wishing so much time in, in trying to set things up? Basically, back to front. And that’s, like, kind of my goal is like, Well, how do we stop people doing that? And realizing, actually, community is really hard. And often, it’s a stupid thing to do. But you know, so people see it as a quick win, win win. It’s not it’s, it’s the long is this a very, very long game.

Arvid Kahl  22:42  

That reminds me a lot of the audience building movement, like everybody wants to have an audience. And I mean, I teach people how to do it. So I’m kind of part of it. I gotta say, right. It’s like, I’m also am building an audience because I have something that I want to share with people and I need people to share it with for it to be shareable. i It’s kind of, it’s just a self fulfilling prophecy as well. But obviously, you can overdo it in terms of I just want an audience no matter why no matter who no matter what. And you see a lot of people going just for sheer numbers, and inviting people into empty, pointless communities. 

And what I’ve what I’ve found over the last, I guess, year and a half, that’s been an incredible resurgence of community building tools that make it much easier to build communities to invite people to have them exchange information, but very little has changed in terms of why, you know, like, you can do it easier. But the underlying reason why you build a community that hasn’t changed, right? So with this resurgence of tools, and you’ve been part of both using new tools to build community, and you’ve been working for companies building these tools, what is your perspective on this? This incredible community centric tool resurgence that we have been experiencing?

Rosie Sherry  24:00  

I wrote a post that just does like what is a community tool? What is it? Community tool is anything that allows you to communicate or publish something to people. So like a blog is a community tool. It’s a way to communicate an email list, Google Doc, Mirabaud, a forum, a chat space, they’re all on different levels of communication. Yeah, people get stuck in what is the community like they say, “Oh, it’s a chat space like this calling slack or it’s a forum. You have to have one or the other. You can’t have both.” I’m just like, “You can have all of them if you want. If that’s what works for you.” I have a habit, Twitter space, Twitter community, have a forum. I have a blog stroke newsletter. I have a slack. Not everyone’s engaged in all of them, like it works at different levels. I think a lot of community tools have been built by people, actually don’t know a lot of that community. 

And my current vibe at the moment is that they all focus too much on conversation, the slack discord, before rooms. They all like, let’s talk and let’s talk and let’s talk and then it just like soon becomes this overwhelming mess, which is why people end up dropping out so quickly. They can’t keep up. The conversations aren’t actually that useful. So what’s more useful is yes, conversations are important. They’re a big part of building community. But the problem is, all those tools have that sort of like, you need to balance it out with other things you need to like help people progress. You need to publish stuff. You need to level people up. You need to create courses together, not just the founder of the community. 

But like work with your members to help publish stuff. Yeah, you want to help people find jobs, or consulting, gigs, all these like, you know, different levels that members need to achieve, and that are really important to them. And so if they need to find a job, and they know that your community is a place to find a job, well, that course will help them get to the next level or being certified will help them get to there, then they’re going to come back, right? But they’re not going to come back for the conversations because they don’t have time to talk when they have to go find a job. 

And so it’s the tool that basically TDLR is tools to focus on conversations, and not actually about elevating people and helping people longer per that I often look at tools, like original communities. Like a great example, even though it might have like a love-hate thing for it is like dribble is like dribble as like, people showcase it their work, right? And that that benefits them. If they build a reputation, they can find work opportunities through that it can, you know, do all sorts of things. But dribble offers a lot more than that now, but it’s like at the fundamental aspect of dribble. It is a community but there’s not a lot of conversations. It’s only a very small part of it, Jen and all the other conversations happen around like artwork. 

Arvid Kahl  27:26  

Yeah, they’re almost visual conversations. And when I look at the sites like dribble, or what forest used to be, or whatever the other kind of visual art board style comm. Platforms, what I see is that over time, styles change and themes change. And people pick up the influence of one person, the ideas of one and express it in their own artwork. The conversation is just happening in a completely different medium. 

And it’s not supposed to be text, it doesn’t have to be like a forum thread, or people like voicing their comments, their opinion in the comments like that doesn’t need to happen, right? For the platform to succeed. I love that idea that there’s way too strong focus on conversation, and maybe too little focus on actually solving the issue that people come to the community for, or at least providing a way for the knowledge to get to that goal to be shared within the community. I think clubhouse and even Twitter spaces are a great example of this. They are the least searchable, and the least indexable that the least permanent kind of thing that people spend a lot of time and effort on. 

And I myself have been on many of these things, talking to people, sharing, and whatever I know. So I talked for like half an hour, maybe 40 people listen to that. And then it’s kind of gone. That may be a link but who’s gonna listen to this for half an hour to maybe find some information. It’s just super transient kind of medium, which is very much not building this wealth of knowledge in the community. So what do you think about audio? Being on the podcast? What do you think about the audio medium as a means to transfer in from little audio?

Rosie Sherry  29:07  

I love cluttered spaces. I hate that Twitter spaces is very temporary. It’s like, you know, show up, be putting all this effort and then it’s gone. And it’s like, well, what do you have to show for it? It’s like nothing. I can’t bear, it drives me absolutely nuts.

Arvid Kahl  29:25  

Yeah, it’s the opposite of a blog, right?

Rosie Sherry  29:28  

Yeah, and then the other side and say podcast and inside. I was podcasting was easy. I wish like you could almost say just show up like on a Twitter space and then turn it into podcast. I think you can kind of do that with like anchor FM or even Spotify a green room, which is kind of like Twitter spaces, but then you can automatically send the podcast over all the conversation of anchor FM. So I think there are ways but like, it still feels like it’s too much and It’ll be great like, you know, like this conversation if I could just like record something like this and hit publish, because to be honest, I was editing and stuff was. That’s what stops me from podcasting.

Arvid Kahl  30:12  

It was just thinking, yeah, editing and actually hitting records to start a conversation. These are hard things, you know.

Rosie Sherry  30:18  

Really hard

Arvid Kahl  30:19  

That doesn’t work all the time. Yeah, it’s that’s always kind of this technical hurdle that you have to jump over right to get some kind of content. And I get that people expect a certain level of quality. So you might want to have a nice microphone and a sound insulated room and you know, all these things to then produce what you didn’t actually say what you want to say, which doesn’t have to do anything with the quality of technology, right, you could probably talk into a microphone while running through a city. And it would still be interesting. I was, again, Daniel Vassallo, I was talking to him. And he was explaining to me how he did his Twitter course, and why he started making a course because he was not interested in doing any of this. 

But then, for some reason, he downloaded a little course on some E-commerce stuff by a woman who just literally had her iPhone out, tucked into the iPhone while she went into a shop and bought something to then resell on an E-commerce platform, like just filming herself, like shaky walking into a place. And that was her course, the whole thing. And it was interesting. It was insightful. It communicated exactly what you needed to know, to be able to do this, there was no production value in this, there was no fancy equipment, was just somebody self viewing themselves, while doing the thing that mattered.

And I find if we could step back from all this technology stuff, and I’m kind of also, it’s also a problem for me, because, you know, I have a little studio. I have the lights here and all these things. But in the end, I could just sit in whatever room and talk to you right now. And it would still be the same conversation, right? We put too much of our emphasis on tools, be it for content production, or for community building, and too little on what we actually want to communicate and why the things should exist.

Rosie Sherry  32:07  

A good community to all be one that facilitates all of this kind of stuff easily. And not. Yeah, yeah. Yeah. It’s just too hard for community builders to deal with creating a podcast is so much. It’s a hurdle, right? And so if we had tools that made it quicker and easier to have these conversations and outputs in a useful way, that to me is where community tools should be thinking, not repurposing what the web already has, which has been a long history of courses and forums in chat spaces, which is basically what community toolbar at the moment.

And they’re very, like creator led, which means they’re very focused on this one person at the top, who profits all the money, rather than trying to think about strategies of how can we create opportunities for, how can we have other community members contributing to this course or collaborating on stuff or submit an article. There’s nothing out there at the moment that facilitates that easily.

Arvid Kahl  33:15  

So we need one more tool? Is that what you’re saying? Yeah, it feels like we have all these little tools that by themselves do the thing we want, right? We have newsletters, so we can distribute our knowledge to a group of people who have opted in. We have podcasts for people who want to listen to something while they walk their dog. And we have all these other tools for communication for conversation for knowledge, persistence, like we have notion shared databases, Google Docs, where people link things and put information. And I honestly, the feedback Panda, the SAS that I built with my partner, Danielle, that happened because we saw people sharing information in a shared Google Doc, or it was like Google Sheet, or something that they were already collaboratively in their community exchanging information. 

And we built a business on top of that, because we saw that there was something happening, right? The community was working with each other. Now, they just needed somebody to actually funnel it into something that is not just a Google Doc, but something that works better and integrates with whatever they need it. So that’s where our business came from, from a tool that a community built for their own purpose. And not that it’s crazy to think that everybody is building community tools, when the community can actually deal with Google Docs and get done what they need to get done, right? It’s just seems like people are building the wrong tools, if that’s what people still use.

Rosie Sherry  34:33  

That’s frustrating, right?

Arvid Kahl  34:35  

It will, yeah, I feel. We look for these different tools. And I think also as founders, we built yet another community tool, because we know it’s hard to build a community. It’s hard not just to build one, building is to me, it always sounds like creating it or making it happen but to maintain it to consistently engage with the people in that community. 

And now that I have you here as somebody who’s doing this on a four days out of five in the week basis, how do you stick with that? Because I quickly find not that I’m bored with it, but I’m overwhelmed or I’m saturated with the things that happen in the community. And I need to, you know, take a day off. I need to get some space and then come back. How do you personally feel invigorated to go back and engage with the people in your communities?

Rosie Sherry  35:26  

A lot, I think a lot of it is that, especially for like royalty land, there’s so much work. And I can see like, and I know, you know, this too, and apply this as well. But like, the deeper you go, the more rabbit hole we find, and the more you’re like, “Holy shit, why aren’t people talking about this? Or thinking about this? Why are we even building like communities without like doing community discovery? Why is no one even using the term community discovery? Why? What is like, Oh, my God, it’s just like that, and that excites me, I guess. I’ll tell you the fact that I think like communities and everything sounds like, you know, finding opportunities as asked education as an answer to a better world. 

Literally, if we were all better connected and understood each other and had good safe spaces to exist in, I think the world would be so much better off. And then there’s also the ideas like, the SaaS market, I think is very saturated. People struggle to get any kind of stuff off the ground. I think there’s a niche for community in every pot, everywhere that a SAS exists. There’s a need for like an independent community to support that kind of nishal that industry. 

But, you know, at the same time, I think a lot of them should be custom built. And there’s not enough custom built communities out there. Ivan and has a whole big other thing it happens is custom built and administrivia testing is majority custom built to serve the needs of its members. Dribble has custom built, you know, like if people want to take community seriously, custom build, well, obviously, that’s hard. But like, Indie Hackers did some interesting things exploring different ways like product directory, for example, members having their own newsletters, I think that’s super cool. Since I just think there’s a lot of opportunities, still to explore better ways to

Arvid Kahl  37:42  

get you have a pretty long history with the Indie Hackers community to one thing that really interests me is how you got into this. Because, you know, like, we all come to into indie hacking from very different different spaces. But you came to indie hacking, and then you manage your community. How did that happen?

Rosie Sherry  38:01  

Yeah, I mean, like, I was in Indie Hackers, basically from 2007. That’s when I started in industry testing. And then I stood back, because I kind of got bored and testing is like an industry and I wanted to focus on community. So I stood back in 2019. And I still own it. But I don’t run a day to day, which is pretty amazing. 

Arvid Kahl  38:25  

Yeah. That’s perfect. That’s what we all want right on it, but don’t operate it perfect.

Rosie Sherry  38:31  

It’s a very nice place to be. And as long as it’s probably profitable for as well, but yeah, which is good. Thank God. But yeah, so I stepped back from Ministry of testing. And it was really hard to step back. I kept finding excuses to go back in and I’ll just help out a little bit, or the team would that, you know, ask me for my help. And I kind of decided that I need to find something else to do otherwise, this is gonna keep happening. I need another job. Like I need another project. 

And I was part of the Indie Hackers community. I had done one of the early interviews that text based interviews, had posted on Reddit as well and made caught on very happy about that. He got like, you know, drove a bunch of traffic and stuff. Yeah, around that time, I checked into the Hackers and I saw that Courtland was looking for some Twitter help or social media. I think it was Twitter. And I was like, “Oh, I could do that.” And he was sure. I thought you’re busy doing something else. And as you have, you know, I’m stepping back and do something else and I’d love to help. 

But basically that conversation ended up turning into like a community role. You should it shouldn’t Twitter you should also help me lead the community. Outside. Yeah, I’m not too bad. Yes, it’s interesting, I guess, because he reacted in a way. So obviously, I was overqualified for the job. But for me, it was like, “Oh, Indie Hackers. It seems like a great community. I’d love to learn. So I went in there with like, the complete what’s the right word just was my eyes open and, you know, willing to take in and try to understand say, “Well, what makes this community tick?”

 And also, for me, it’s like a confidence in music. I’ve done the history of testing for over 10 years. Do I really have it in me to help and I look at am I good enough? Or was it was a one trick pony kind of thing. You know, it’s like those kind of self doubt things also existed within me. So for me, it was there’s a great confidence booster and great, great way for me tattoos. Yeah, no.

Arvid Kahl  40:58  

That’s self doubt stuff. Like I think like impostor syndrome, and whatever you may want to call it, every founder kind of has to deal with this. But I think like female founders, in particular, have are constantly being product and, you know, get double the attention, get asked questions that men don’t get asked, right? So is that something that you struggled with in that community? And in particular, or is that? What did you do run into different kinds of scrutiny? With this?

Rosie Sherry   41:31  

I know, I ended Hackers. I worried that was going to be personally but actually, it was really positive. The world was over. And because obviously, like Indie Hackers is 90% men as well. And part of me is that, “Am I ready to deal with men that day in, day out?” posing a shocker. It’s like, you know, if I was gonna get attacked, or you know, like, have condescending comments, you know, talking to me, but actually, I got none of that, which is, you know, great. 

And a credit to Indie Hackers as well. Obviously, it’s not perfect. I don’t think any community is. But yeah, like, in that community, in particular, is a big community and I was on the front page, a lot of the time just posting stuff and stuff. That was great. Great for me.

Arvid Kahl  42:30  

That’s kind of at the time when I heard first about you and your work. And you just being present there immediately. Get in my perspective gives you the all of the reputation like it to me, “Oh, well, this person knows what she’s doing. Like, she’s wrangling this community. She’s awesome.” That’s kind of how I felt, right? Because in the hackerspace, is wildly diverse in many ways, not necessarily by gender. 

But you know, in other ways where people come from. They come from all different kinds of places, all different kinds of work. I mean, there’s probably still a lot of like, white male software engineers, who then build stuff. But you know, like, there are a lot more people beyond that. So seeing you dealing with this and not taking shit, and just doing your thing, I really liked that. It was very, very enjoyable. And ever since then, I’ve been following you and your endeavors. And you stepped and then at some point, you stopped with the Indie Hacker community management. What happened after that, like what was your path through the community worlds beyond that?

Rosie Sherry   43:33  

Yeah, I feel like I kind of hit a wall, was indeed hackers with what I could get. And so I thought it was a good time to step back and focus in Roseville. And then I got distracted by a job offer. As like, you know, it was a peak community craze, I think, looking back at the time, all these companies raising money. And I don’t want to take a job.

Arvid Kahl  44:05  

I remember talking to you, I think we were chatting, right?

Rosie Sherry   44:11  

Back, give it a shot. And I kind of like believed in what they were doing and stuff like that. And like the idea of innovation and community it seemed interested in the idea of leading seemed interesting. So yeah, I think lastly, it’s

Arvid Kahl  44:31  

just this is the Indie Hacker Kool Aid once you drink it, you have a problem. Yeah, it’s kind of Yeah, that’s kind of what I wanted to know. Like being in kind of a self determined community leader versus being a salaried employee. What was the difference there? Was it about agency or about like vision? What was limiting you if you can talk about it? Of course.

Rosie Sherry   44:54  

Yeah. So I kind of rage quit and I think a lot of it is about agency. And obviously, I don’t say too much. But when you’re into hockey, you just like want to march forward and you want to have, for me is like, creating change and kind of being part of the business as a whole. But in the end, I don’t feel like, I didn’t feel like I could have the impact that I wanted to create. And I felt like it was going in certain directions that I didn’t believe in. 

And I think for me, it’s like, points, I don’t believe in something I go massively to stick with it. I want to say yeah, and just like, wouldn’t start at the money. They hire massively. And it was just like, I think also employee number eight or nine. I felt like it grew massively, but the product hadn’t necessarily changed, like, went from 9 to 50 people, but nothing had actually changed. And yeah, it’s just like, I didn’t, yeah, I struggled a bit with that. 

But there was also conflict with Rosieland and OB. So that was doing a lot of community stuff that I was really supposed to be doing for Rosieland, and I ended up doing that for Orban. And that created a constant conflict, which they were aware of, and we talked about openly. But I think in the end, I was like, I can’t create an authentic community around the tool that has biases. So I have to choose. And that I didn’t feel like they were invested in me. But just hard.

Arvid Kahl  46:49  

Yeah, I bet. I mean, there’s always an opportunity, right? You probably see that there is something like somewhere in the future that could really make a huge difference with these startups. The vision, the mission, you know? Well, it’s a testament to your integrity, as a community builder that you stepped away from something you didn’t believe in. 

I think that in a world where everybody’s trying to look out only for themselves and only, you know, jump at it any benefit they see saying no to a sizable opportunity. And going back to what you actually want, that’s just you and I like that. It’s really nice. It’s just nice to see that you walk the walk, right? I feel that is something why I trust your advice, why I trust your knowledge that you share, and why I think you have a lot of things to say to community builders about how to actually be a genuine and authentic center and or facilitator of community. So very, very interesting. So, at this point, you’re completely focused on your own projects. Is that right?

Rosie Sherry   47:55  

Yeah. Mostly, Rosieland. Slowly, independence, as well. Part of it, I think is like, kind of building a portfolio of communities is what I’m, I’ve got free at the moment. So that’s ministry testing, Rosieland independent. And, but mostly roseola. And that’s like my main focus, I realized I can. I have to focus on that, and I want to focus on it. And so I left over the year, and I basically restarted everything from scratch. Again, I canceled, like all the subscriptions on my, you know, trying to like, decide to say what do I, you know, just like trying to deal with the admin of canceling someone or others? Or how do I manage it, how to import them into goals. They’ll just cancel them all and use it as an excuse to start over. 

So I started from zero, and that was around March. I was slow the first few months. This is so depressing. But you know, it’s gonna right now. I’ve not quite reached my first 10k month, but I’m almost there, it’s awesome. Not thinking are all but like thinking that, but, so I’m quite happy with that. And I think it’s only going up and up at the moment. So it’s slowly because consistently getting, you know, if I get to say one to three subscribers a day, so you know, it won’t take long to me to get to where I’m at. And it’s pretty cool. Actually, it’s going mostly for subscriptions. 

But I’m also introducing like company subscriptions. So I’ve got like four company sponsors, which has been pretty nice. I’m trying to like build a balance of relationships. So it’s not just members and I’m trying my best to probably do what I’ve always done best is, like collaborate with members. And so few things going on behind the scenes, but like one of them is like a community curriculum that I’m working with a guy called James, and we’re gonna open source it. We’re gonna, like, have the basic foundations of it being open source. We’re gonna do it in public. And I’ve just been searching other GitHub sponsors for it. So we’re gonna, like, see if people sponsor it as a way to make money from it. And part of that is like, we can reimagine, like, what communities are supposed to be about. 

And at the moment, like, as much as I love, like the creative economy, I feel like all the communities are very much focused on the creators at the top. They’re the ones that actually benefit and say yes, to community members can talk there, and they have some voice. Really, it’s like, it doesn’t trickle the economy. It doesn’t trickle down the members. And obviously, like the past year or so it’s been like, what’s crazy about the Web3 in Dallas and all that. I don’t personally subscribe to that. But like, I do believe in the idea of sharing what you make in community with community. So I think there’s other ways of doing it, not necessarily on sharing revenue, working on stuff together. You know, all these kind of things. And that’s what I’m excited.

Arvid Kahl  51:31  

I love that. I guess that sounds like you take the core principles of why families work so well, supposedly work so well, because people collaborate. They have built meaningful long term relationships with each other, which they trust each other, right? That and you transport that into a bigger scale of a community. And you keep those core functionalities as your focus, instead of thinking about, like how to make the most money off from or from this community is how do you empower them the most, that is very much aligned with what I love, which is helping people help themselves and others. So I’m really, really grateful that you’ve been sharing all of this with me today. 

And people who are listening, I will take a much closer look at what you’re going to be doing in Rosieland with your community, curriculum and all that stuff. That sounds very exciting to me to also, you know, help foster community around the people that follow me and do stuff. In my circle of vision. Where can people find you? Where can people learn more about what you do? And then hopefully you sponsor and subscribe to your things?

Rosie Sherry  52:37  

Yeah, so Twitter, I’m rosiesherry on Twitter, and rosieland, probably the best places, which is rosie.land. You can subscribe there. You can be a free subscriber. Greg can sponsor it.

Arvid Kahl  52:53  

Yeah, it’s freemium, right? You went to the freemium? That was nice. Yeah, very inclusive. I love that. Well, yeah, we have a community of different means, right? That’s kind of why I also go into, like, purchasing power parity pricing for my stuff. And we have to get everybody like, be the tide that lifts all the boats, right? And I think that’s who you are, as well.

Rosie Sherry  53:15  

I think that’s part of it. You know, one thing that I didn’t touch upon is like, I didn’t commit to that. I think I coined that term, feeling community acquired a lot of terms of the first two years. And it’s only because like, no one thinks about these kind of things in community. It’s all kind of like, no one’s been trying to innovate. 

So it’s like, when I see why this like an indie world, or startup world or business world or something, I stick like community on it, or I stick like other terms on it. And it becomes a thing, but it becomes a thing because there’s a wait for people to actually understand and premium community is. One of them is like, it’s partly free, it’s probably paid, there’s a mix in it. Where it’s like a lot of people just talk in terms of, well, it’s free, or it’s paid. And so having a language basically is important for us.

Arvid Kahl  54:10  

Yeah, the way we talk about things as to where we understand them, and then make them a reality in the world, right? That is a great idea, generally a good idea to take terms from one industry and just like mix and match them with one from another or field. And then see if it’s feasible, if it even makes sense, or what comes of it. Freemium community, I love that. What a nice, nice idea of being both inclusive and having a way to monetize. So it’s the perfect way of like building a business and a community at the same time. 

Thank you so much for joining me here today. That was a really nice conversation. Thank you for being on and that’s it for today. Thank you for listening to The Bootstrapped Founder podcast. You can find me on Twitter @arvidkahl, ARVID KAHL and you’ll find my books here too, sold in The Embedded Entrepreneur and my Twitter course, find your following there as well. If you wanna support this podcast and me, please go to ratethispodcast.com/founder and leave a rating and review, if you can find the time. It would be an amazing and very helpful gesture. Thank you so much for listening, and have a wonderful day. Bye bye!

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