Building Highly Engaged Facebook Groups that Grow Themselves with Dana Malstaff

#15: Dana Malstaff, founder of Boss Mom, shares what she’s learned from organically growing the Boss Mom Facebook group to over 45,000 members.

She also tells us her secret to keeping group members highly engaged and explains the biggest mistakes she sees people make when starting their own Facebook groups.

Check out Boss Mom at

Episode Transcript

Ep. 15: Building Highly Engaged Facebook Groups that Grow Themselves with Dana Malstaff

Dana: I have a choice for you. Either you can go and you can spend six hours doing this breakout session and then you're up to plan and figure it out and you know, I need you to be smart. I need you to look good. Or you get to go to a party. You'd go, well, professionally, it'd be great to go to this breakout session, but you'd be excited about the party because the party sounds fun, but you have no obligation to be the leader, to be smart, to teach everybody. But we start Facebook groups and we think I have to be the provider of content and that's not actually really what Facebook groups are for. Granted, there's absolutely a place for you to teach and give content for sure, but it's less often than you would think. And it's more about being in a club or you're hanging out and having coffee with friends but behind the scenes, that's more of what people want is the inside scoop.

Josiah: That was Dana Malstaff, Founder of Boss Mom, and in this episode she shares what she's learned from organically growing the boss mom Facebook group to over 45,000 members. She also tells us her secret to keeping group members highly engaged and explains the biggest mistakes she sees people make when starting their own Facebook groups. Dana is a brilliant entrepreneur and content strategist and I learned a ton from this conversation and I'm sure you will, too. So let's jump in.

Announcer: You're listening to the Content Heroes podcast where entrepreneurs, marketers, and creatives share how they build profitable businesses on their own terms by creating content online. And now your host Josiah Goff.

Josiah: Welcome to Content Heroes everyone. I'm here with Dana Malstaff, the Founder of Boss Mom. And I'm really excited about this conversation today because we're going to be talking about building a community through Facebook groups as well as a lot of other stuff. So Dana, thanks so much for being on the show.

Dana: Thank you for having me. I'm pumped to be here.

Josiah: Great. So let's get started with your origin story and just tell us a little bit about how you got started and the and how you founded Boss Mom.

Dana: Yeah. So I quit my job and everybody went out and got me drunk and then I got pregnant. I was married. It was my husband. We'd been trying and we hadn't actually been able to have a kid cause I had 14 hour days. He had 14 hour days. I was a director at a patient advocacy place from the marketing side. And he was in the commercial banking sort of side. Yes. We both work long hours, wasn't able to have kids. There was a shift in the company I was in or the husband and wife that had started the company were getting a divorce. So there's this big upheaval happening. And so I decided, hey, I'm gonna go and get a different job. Went to go get a different job, couldn't find anything that I really loved. And a mentor had put it in my ear like, you should be a consultant. You could make really great money being a consultant. So I decided to go out on my own and we had been making really great money. So we had a bunch saved up and we were like, yeah, let's do this. And then I immediately get pregnant. I mean obviously I could tell you like when I was in fourth grade, you know my family was like the MacGyver duct tape family. So really from a boss mom perspective, the origin story was I basically conceived a business in a baby like in the same 20 hours. And I joke that if anybody can't like handle, that's too much information that you're definitely not gonna be able to have a business. A business is very messy and very intimate and I basically had no idea what I was doing. My, like to be good at things. So it was very emotionally devastating to not know what I was doing and to not even have a clue about where to figure out. Like a lot of times you go, Oh, I'll just go to school and learn this thing. I got lucky. My entire college education was useful cause I was a broadcast journalism major. So I was able to, you know, I know how to be on video and I know how some, you know, graphic design and some of those things, which is really useful. But when it came to like running a business, I had no idea, nothing I'd learned in school was helpful at all in that area. And I just had to start figuring things out and then failing and then changing my mind and then trying to figure things out and then convincing somebody to pay me and then not knowing why they paid me. So I had no idea how to replicate it, you know what I mean? You're like, this is awesome. I have no idea how to do it again. I did that for two years, still felt really alone and isolated. Like I didn't have my people. We moved out to San Diego from Columbus and all of a sudden I realized people in San Diego, they're entrepreneurs and they're mom entrepreneurs and oh these are my people and this is going to be great. And I was still trying to figure out what I was doing and I got hooked up with a couple people in a mastermind, one of which was Azul Terronez, who's a book coach. And he just said, Hey, if anybody here wants to write a book, I'll give you guys an amazing discount. And I was like, I've always wanted to write a book. Thought it was going to be about content strategy cause that's what I've always known and been good at. And it turns out that Boss Mom was what I really wanted to write. So there's a lot of times where people tell me, I don't know if I should write a book. And I'm like, if you can't figure out your brand, like if you can't figure out what you stand for, if you can't figure out what your opinions are and what you really care about, then a book is a great place to start because it helps you hone in on what's the legacy I want to leave? Like what do I want to be known for? What do I care most about that other people understand? And it wasn't content strategy. Even though I love teaching that. Like the legacy was that you're a smart, beautiful, brained woman who has a lot of value to add in the world and part of that value isn't just being a mom and it's okay that you feel that way. Like it's okay that you're yearning to figure out what being a woman means again, after you've been married and have kids because you were thrown into this, I mean, you know, you've got a wife and kids. Once that family unit happens, like what does being an individual mean is something that I think we totally gloss over in the world. And it really is something that we grapple with. Like I'm a father and a husband and a human being outside of itself. How do I get all three of those things to feel whole without feeling like I'm taking away from each other, which is where the guilt comes from and that's where Boss Mom was. So I said, you know, the best way I can help these women find their value again and be a part of the world and show their kids that doing something we enjoy isn't life draining or that we don't have go to work in order to make money to do things we like that it can all be one life that we lead, is I can teach them how to create online businesses that grow so that they can have flexibility with their time with their family. Because schools are not built for both parents going to work like kindergarten is three hours and school gets out at one or 3:00 PM like none of it's rational. None of it's built, none of it's built for two working parents, you know, so how do we, how to create a system where women feel like they can contribute with their brain and impact people outside of their family and be there for their kids when they want to be there. That's the ultimate goal. That allows me to do what I'm really good at and do what I'm really passionate about together. And thus Boss Mom was born and now we just boss mom the heck out of everything because you know, why wouldn't you?

Josiah: Oh I love it. So when you were making that transition from, you said you had done consulting and you started to write a book, what did that transition look like into the boss mom space? Like how was that brand born and what did that look like in the beginning?

Dana: It was messy, like most great things are, I do what I recommend for everybody, which was something that I had done in corporate. And then with my book coach we kind of was using his advice and we sort of married it together is to go ask. Like a lot of what my background and training in question-based selling and facilitation and all of these things is, and I used to literally put together and run focus groups is one of the things I would do back in previous jobs. And I was a journalism major. So I got a degree in asking questions. And that's all we did is I went out and I started asking everybody, what do you think? I hired a copywriter and we brainstormed 25 names and we narrowed it down to four and I went out to other people's communities online in Facebook groups, and I said, which one do you guys like? And tell me why. And we had hundreds upon hundreds of women tell us they liked boss mom, which was my least favorite, by the way. I know Stephen King always says, "you kill your darlings", which is basically anything you think is brilliant, the market generally is going to have no idea what you're talking about or care. So usually that's the first thing. You can literally, every book cover I've had, podcast covers pictures of me where I'm like, Hey, we're about to do a new mailer. Like which picture do you guys always, the one that I like is dead last, you know? And it's good to know that and it's good to be like, okay with that. So yeah, I just went out and I asked, tell me what cover you want, tell me what tagline. They helped me come up with a tagline for the book. And in the effort of getting them to actually, I call decision support, like give me decision support and do market research at the same time, they started to buy into the idea so I didn't have to say this is what my brand is about. Please love me. I said I need to make some decisions about this thing I'm making. I don't know exactly what it is but I love if you would help me figure out what it is. And in doing so everybody got excited about it and then I said, well now that we were going to have this book, why don't we make this group and we'll all hang out there. Several hundred people went over and did that. Basically when we've got to like a hundred, which is really quickly, I'd go and do a dance party. Lives had just started cause I remember I started on Periscope and then moved over and then all of a sudden Facebook was doing lives for all the people that think Facebook lives just always existed. I'm aging myself. We do a dance party and to be honest, every single content creator and entrepreneur and leader, some of it is figuring out as you go, if you try to enter into anything, a romantic relationship, a friend relationship, a business relationship, a business building, anything thinking that you have to have all the answers in order to get started or get it to work, it will fail every single time because a relationship is relating and business is people, which means we have to ask questions, find out what people want, understand what they're going through, understand you know who they are and the kind of people that are connected to you and that resonate with you. It's a give and take. I always say like in business we need to find room to play because instead of feeling like we're putting something out and it's failing, if you're playing, then failure is not really a part of playing. Failure is something you do when you're trying really hard and it doesn't work. When we learn to play, then we're just playing around. We're just putting some Legos together and seeing what we come up with and all of a sudden something's brilliant and you're like, well, I'm going to make that again. Like that's what content should be like. It should be a collaborative effort. And so if you're going off and trying to figure it all out and then impose it upon people, it's going to be a lot harder to get everybody excited about it. Than if you let them help you build it and then that way you don't have to have all the answers with what a fricking load off. If somebody told you you want to have a really successful business, you don't have to have all the answers. You just have to start trying and seeing what works and then recognize the 20% that works and run with it. And the moment you start seeing the 20% or the 80% that doesn't, but you let it go fast, like you let it go fast and you spend more time on the things that work. I mean, that's the other thing I always tell people, do not fall in love with your own content. Don't do it because the second you do it, it's like any relationship where you're like, yeah, but it's good enough so let's just stay in it. There's an opportunity cost to loving your content that's not working. Like just recognize it for what it is. Set it free into the world. And like Elizabeth Gilbert said, ideas are like things that want to attach themselves to people and it will leave you if you're not serving it. Let that go and somebody else who is going to do well with it is going to come up with the idea and it may work for them, but like set it free. If you love it, set it free. That's what I say.

Josiah: Oh I love that. What you said about play, because the times in my career and in my business when I've gotten the most frustrated, the most burnout is when I took the fun and like took the play and de-prioritize that and said, okay, this is what we gotta do. And just gotta you know, grin and bear it and push forward and then you just start losing traction. But if you treat everything as well, what you talked about, play and an experiment, there is no failure. You're just learning as you go. And it's a much more collaborative process. And one of the things, one of my mentors says that always sticks with me is if I feel bad that means I'm miscreating. And I love that cause it's anytime I start to feel bad then I can take a step back and say, okay, what am I trying to create that is not aligned with who I am or that I'm not having fun with? And then I just start pulling those things out of my life.

Dana: Yeah.

Josiah: Let's dig into the process that you have for building that community. And I have to admit, I have a bit of an ulterior motive. So like we talked about a little bit before the call classic entrepreneur. I had, you know, a hundred different goals at the beginning of starting Content Heroes and like we're going to do all this stuff. And then like I launched a podcast and launch, you know, Facebook community, and it's going to do all these things and very quickly realized that, you know, if any of them is going to work and do well, I have to focus. And so I started the podcast. I really want it to be a community for online content creators. I started the podcast and I started the Facebook group at the same time. And then just quickly realized that like, I did not have the bandwidth to really focus on both of those things at the same time. And so I chose, let's focus this quarter, we're gonna focus on the podcast, make sure that that process is down, that we're consistently putting out content and booking people on the show and that we're delivering things of value. And then in this quarter, I feel like we've got that down pretty well. And so in this quarter I've started to shift my focus on, okay, how can I really start to maximize that and to amplify it and build that community? So a lot of these questions I'll probably ask for myself as well as the audience but how do you start and getting people to engage in the community when you have, you know, I think right now our Facebook group is just under a hundred people.

Dana: Yeah. Well, one of the biggest things is if you're building it right, it shouldn't feel like it's a project you have to dedicate to. One of the biggest things I say is that in Facebook groups, the biggest I think mistake people often make is they think they have to be the teacher. They have to be kind of like the prophet, so to speak. The person that stands up in the front, you know, that says, here's what you need to know. It becomes burdensome for you because you have to show up all the time. Imagine if someone said, okay, I have a choice for you. Either you can go and you can spend six hours doing this breakout session and you have to plan and figure it out and that, you know, I need you to be smart. I need you to look good like this. You know or you get to go to a party, right? He would go, well, professionally, it'd be great to go to this breakout session, but you'd be excited about the party because the party sounds fun. But you have no obligation to be the leader, to be smart, to teach everybody. People don't have to walk away from the party feeling like they got something really educational you, but we start Facebook groups and we think I have to be the provider of content and that's not actually really what Facebook groups are for. Granted, there's absolutely a place for you to teach and give content for sure, but it's less often than you would think and it's more about being in a club, something you'd talk about in a book club or you're hanging out and having coffee with friends, behind the scenes, that's more of what people want is the inside scoops. If you're doing things on your podcast and you want to go into the Facebook group, you can be like, look, I was recording this and I had someone came up with this question and I've, I want to discuss it in this group. Like this is a good place to dig in deeper. So you can even take things from your podcast and go into the group and say, let's talk about this thing. So the first thing is, is taking yourself out of a teaching role and putting yourself in as a facilitator role. A group is a place that you facilitate, which means what you want is for other people to have conversations. And the biggest challenge with Facebook groups is that people don't know what to have conversations about. So part of what you have to do is with the questions you ask in the group is you start to train the people that are coming into your space on what to ask and what to do in your group. So that's the biggest thing is because I bet you they're a ton of content creators, even the people that are in your group right now that have questions and ideas that they could totally post in your group, but your group doesn't come to mind because they're not exactly sure how do to use your group? So when there's uncertainty, when there's not boundaries, when there's not good guidance on this is exactly what you do in my group and this is how you can find it beneficial, then you just lose opportunities because people don't think of you, right? And Seth Godin always says you want to be first to mind, right? It doesn't matter if you're first to market, it matters if you're first to mind. So we've got to condition your group. So the best way to get started is to come up with a series of question and we call it like a buzz plan of what conversation do you want to start? Right? You know, if we're talking content strategy, it's an awareness campaign, right? What do we want people to be aware of? Do you want people to start thinking about, like if we're talking about engagement and you know, this episode's going to be coming out, then maybe you want to start having this conversation of how do you actually get people engaged with your content, right? So then you go, okay, if I want people to start getting engaged with content and we're all content creators, what questions can I ask - Simple for people to answer, right? Cause that's one of the other big mistakes is you go in and you ask these esoteric questions that involve a lot of time. And people are on their phone, they're on the go, they're in the middle of dropping their kid off at swim practice. Right? Or like having happy hour with friends and they see something come up. And if it's not immediate, if it's not a yes, no question. So I remember a colleague who posted something about, Oh, just the end of the year. And they said, Hey, you know, does anybody feel like 2019 was just a building block for 2020 and how did that make you feel? And they came to me and they're like, no, but it was like crickets. Nobody cared. I said, I asked that same question only in my group. I said, are you scared or excited for 2020? And that was it. Are you nervous? Are you nervous or excited? For 2020 we had hundreds of people because all it required them to say was nervous or excited and then a certain percentage of people had more to say about it. And then that's where I started conversation. So I think what we think is in a group, we have to ask these really deep questions, but the simple questions create engagement and then the deeper conversation happens in the comments within those conversations. It's the same way Instagram works is that you simplistically want to get people engaged. So for you, you might just ask questions in the group, are you big course or small course people? Like one of the easiest example is in a, you know, in a group it says, are you zero, you know inbox or 10,000 inbox person, who are you? People then can say, Oh, I'm that person. I identify with that. Right? Who creates small courses or big courses, right? Who are my podcasters? Who are my Instagrammers? Like what do you prefer? How do you take an information, read, watch, listen. And people will start to tell you and we ask all those questions in our space, depending on what we're trying to understand or what conversation we're trying to start. So if I'm going to be promoting somebody who has a course on blogging, then I'm going to go in and I'm going to start asking about who are my bloggers, you know, of all the people who consider themselves bloggers, if you're a blogger, do you run ads or not? Right? And what does that look like? Like who here has more than one authority plot? Like who here is a blogger and a ______? And then tell me what the blank is. And then Facebook thinks your special because they're answering. And now more of the people in your group organically start to see more of the content. And that's when Facebook starts going, Oh, we should invite other people to this group because it's interesting and more people are seeing what you have and then they start seeing what you're asking. So they start to get an understanding of what they can ask and then they start asking questions. So it's way less of, don't post motivational quotes, don't teach them things, ask questions. If all we did was ask good questions to start conversation and then the conversation was within the comments of the posts, everybody would have really vibrant Facebook groups. We're all just trying too hard. That's the thing. We all are way over complicating the whole process and it's becoming exhausting and then they think it's hard. It's really not. People want to talk about themselves, you just have to make it easy to get started. That was my rant. That felt like a lot of a rant.

Josiah: I love it. No that's so great. Cause I definitely, I definitely overthink the questions and I'm like, I could probably spend like 20 minutes just like, okay, how do I phrase this elaborate question that gets them to start talking about? And then like by the time I'm done with that, I'm like, Oh this, this isn't fun. I love that. Make it easy for them to answer. And just in the comments, if they want to dig in more, we can, we can have a deeper conversation. But yeah, I think about that in my, in my own groups, like I see someone ask like a really elaborate question. I'm like, I don't have time for that. I'm just going to keep scrolling. So that's totally true. So you mentioned a buzz plan.

Dana: So here's the biggest thing. If this is the only thing, everybody listening that's a content creator pulls away from this, is that most people, their problem is that they confuse the market. So what everybody is taught is that more content is better. And so we sit there and we brainstorm a year of content. Anybody who says they brainstormed a year of content, I tell them that most of it's going to fail because you can only get 90 days of content to really know what the market wants. And if you're planning out a whole year and then that means you're not actually listening to anybody. And you're not listening to trends and you're not listening to what's happening in the world. Like you have to be a good listener to be a good content creator. So I like to say 90 days of content in advance. The buzz plan, the reason we called it the buzz plan and it's based off of in content strategy, what we would call an awareness campaign. Like you're building something to build, you're building awareness of an idea. So online, when I say people are confusing the market, it's because when you talk about content, you could talk about courses, you could talk about, you know, video, you could talk about audio, you could talk about the tech side, you could talk about the sub strategy side. There's a million things you can talk about. If the only thing people know you for is just content that's too broad and people don't know, then when to recommend you, what to get excited about and the odds of them buying whatever you want to sell. When it comes time to sell something specific, they're not going to have been nurtured enough to feel FOMO for missing out on that. So a buzz plan, help set a conversation. It's just a simpler, less business-y way of saying an awareness campaign. Cause an awareness campaign says, Hey, I want you guys to start talking about how like for instance, you know, one of my friends does podcasting and has something where it teaches people how to get their virtual assistant to pitch you on podcasts. Right? So the conversation we wanted to start wasn't the conversation of you should be pitched on podcasts because his audience is thought leaders. So the conversation needs to be that if you want to be a leader, then other leaders have to talk about you. That's the conversation we want. Because if you truly believe that the only way for you to be a leader is for other leaders to talk about you, which is to be featured like we're doing right now, you're featuring me as if I'm someone who's worth listening to, right? Then if that's the only way to be a true leader, then all of a sudden prioritizing getting featured comes up to the very top of your list, which is one of the criteria of getting someone to buy is prioritizing the problem, right? Cause we all buy gym memberships we never use, and we all talk about dieting we never do, right? And we all say we're going to launch that thing we never launched. So we have to prioritize it for them. So a buzz plan helps bring the idea to the forefront of their brain. So when you start talking about the thing you're gonna sell or the thing you're going to do, then everybody goes, Oh my gosh, that's exactly what I've been thinking. I've been meeting. And they don't realize that you're the one that brought that the topic up. Right? So it's not just about asking any question or talking about anything, it's about seeding the idea with them. You know what I mean? Seeding the idea that if you're going to be a leader, other people have to feature you. And, and finding ways to talk about that and make that a conversation. That's what we mean by buzz. And so when you're looking at your calendar and what you want to put out into the world, you don't just brainstorm ideas that maybe have good key word, you know, search and good SEO. We also say, what conversation do I want to start this quarter? What do I want people buzzing about and talking about? And then I can come in and have the answer to that conversation and now all of a sudden I can be seen more as an authority and a leader and people feel like they already needed that thing and now I'm answering a problem that they've made a priority for themselves. Does that make sense?

Josiah: Yeah. That's fantastic. I love it.

Dana: And nobody's doing it. That's the problem. Nobody's doing it. Everybody do it more.

Josiah: Awesome. Well Dana, I know we're coming up on the hour here. Thanks so much for being on the show. Before we hop off here, can you just tell everybody where they can find you online?

Dana: Yeah, yeah. So if you go to we're just opening up a shop, I'm sure by the time this comes out so you can get the buzz plan and other things. You can get to our Facebook group. We also have a boss dad spotlight, so for any of our, which you'll have to come on the show for any of our boss dads. You can go and listen to interviews you do with dads. And then we have the boss mom podcast and we have all the good juicy stuff right there. We make it super easy. So that's the easiest way to find us. And then for all of the moms out there, we've got the boss mom Facebook community. We just hit 45,000 but it's still really intimate and amazing. And we have women that say that's the only group they hang out in because we really want to be a catalyst for women. To kind of get their identity and that feel valued in the right way and get that appreciation loop that's needed so you can find us there.

Josiah: Oh, that's so great. Well, I feel like we could talk all day, so we'll have to have you back on the show and other time, but thanks so much for being on the show today. I really appreciate it.

Dana: Thanks for having me.

Josiah: Hey everyone. Thank you for listening to the Content Heroes podcast. I just wanted to take a second and let you know that we have some amazing guests planned for the coming weeks. So if you haven't already, go ahead and hit subscribe so you can make sure to catch every episode. And if you enjoyed today's episode, go ahead and leave a five star review to help make it easier for other content creators to find and enjoy the show. Lastly, I'd like to invite you to join our Content Heroes Facebook community where you can connect with other online content creators to share, learn, grow, and have fun. To join the group, just visit once again, that is

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