Lauryn Bosstick’s Playbook for Monetizing a Community

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show in which entrepreneurs do what entrepreneurs do best, solve unexpected problems in their business. We were completely wrong. And I'm just like, it's not selling. It was like, we have to start from scratch. I'm Jason Pfeiffer, the editor-in-chief of Entrepreneur Magazine.

1:58You've heard this advice many times before. To build a great brand, you have to build a great community. But this raises a kind of chicken and egg question. Do you build the audience first or do you build the brand first? Lauren Bostic has a clear position on this. I would start by building an existing audience. because this is a model she has proven out well. Lauren launched a blog called The Skinny Confidential in 2011 when she was in college, and it developed a huge following. Then she drove that audience to a podcast called The Skinny Confidential Him and Her Podcast, which has since gotten 400 million downloads.

2:41That success led her to co-found Dear Media in 2018. It's a podcast network that pioneered the idea of using podcasts as a springboard for talent to build multi-million dollar brands. And now Dear Media has more than 80 top-rated shows. And then in 2021, she launched the beauty and wellness brand, The Skinny Confidential, just like the blog and the podcast, same name, because she was continuing to build upon that same audience's attention and engagement. Her success certainly speaks for this strategy. The product launches that she has for the Skinny Confidential Beauty brand are huge. They have this mouth tape that sold 200 ,000 units in 2024.

3:23And if you don't know what mouth tape is, which also I did not, stay tuned. We'll get to it. Sunscreen sold 10 ,000 units in one day. Their ambassador program has 21 ,000 members in it. So you can see why Lauren is bullish on going content first and then product later. I think everyone is used to seeing it done the opposite way. And the reason it's going to be easier for someone like me is because I flipped it on its head. I built the audience first and the content first and the tactical takeaways first. And then I had a sale. But that's not to say it's easy or fast. Content is a slow, methodical game, and not every founder feels like they have something to say or that they even want to be in the content game.

4:14So that's what we're going to talk about today on Problem Solvers. I wanted to dig in on how Lauren thinks about audience building and then brand building on top of that audience. And, well, very unexpectedly, we also got into some of the surprising ways that she now manages life with nearly 2 million Instagram followers and a cell phone that is constantly blowing up. I will give you a hint. It involves feet. I will go to a foot spa. This is like the honest truth and I will respond for two hours. Boy, for your sake, I hope you're listening to this episode at a foot spa. I wish I was making this episode at a foot spa.

4:50Anyway, all coming up after the break.

4:56All right, we're back. I'm talking with Lauren Bostic, founder, of the best-selling beauty brand, The Skinny Confidential, about building an audience and then monetizing that audience. So let's just jump in. I said to Lauren, look, if you were advising a small brand right now that doesn't already have the audience that you have, how would you tell them to start? And here's what she said. So what most brands do is they launch a brand and then from the brand, they try to get the audience. And that's a really different thing. And I think what you're going to see now with a lot of entrepreneurs and influencers and brand builders is you're going to see people first building the audience and first creating the content and then doing the sale.

5:40And so what I did that I think set me up to have product is that I really harnessed in on the audience and the community for, gosh, eight years. I focused on that and then I launched products. So I already had the audience. So what I would do now in this landscape right now is first I would do the give give ask model. So I would totally get the audience community excited about my content. I would give them tons of value, whether it's through a podcast or a blog or a book, whatever it is. And I would really focus on each member of the community. And then I would launch a brand later. I think people hear these headlines like Poppy sold for a billion dollars.

6:28It's like they don't see the behind the scenes of how long that actually took. My advice would be to be the three little pigs and be the one that's building the house of brick. It's slow, meticulous. It's really watering the community. And then from there, then have the sale and the product later down the road instead of doing it how most people do it, which is product first and then community. I think the reason that a lot of people do product first is because product is what they know. They got into the business because they have a product in mind. And I work with a lot of, as I know you do, small consumer packaged goods founders.

7:07And I think a lot of them would hear what you just said and say, okay, but I don't really know what I have to say to an audience. I just know what I want to build for that audience. And if you're saying build the audience first, then the thing that is your product is your words and your ideas. So where does that even begin for someone who isn't a natural audience builder? I think if you're not a natural audience builder and you just want to launch product, that's one thing. But you can't expect to have a huge community on day one then. You're going to have to simultaneously water that. If you don't have any interest in building a community or you don't have a point of view and you don't want to get on social media, that's one thing.

7:52But if you do have it in you, I would recommend zoning in on the medium that works for you. So I think it's really important to be incredibly self-aware of what medium works for you. For me, I was born to talk on a mic. I came out with a mic in my hand. And I don't even mean like from a video perspective. I mean from talking. So a podcast to me is like the right medium. Some people want to be behind the scenes. I'm seeing a lot of really, really cool women right now on Substack. They're creating huge community on Substack and they're creating a name for themselves. And to me, if I'm that girl on Substack, I already have a book planned two years down the road.

8:33From the book, I already have a podcast planned. From the podcast, I already have a brand planned. I already have a product planned. You can take a Substack if you're a really great writer and you like being behind the scenes and don't like being on video. And you can content market to create a really fabulous brand. I think what I see right now is that there's a lot of influencers that will launch stuff, but they don't have the brand in mind. I think what I would advise is have the brand in your mind. So you're building a brand, but you're launching your own personal brand to get the community first.

9:07If you don't want to do that, then by all means, launch product and focus in on that. But it is going to be harder to sell, especially in this day and age, without having a community and an audience first. Something that you said in that answer really jumped out to me, which was to have a point of view. You said you need that point of view, which, of course, is what audience building is based on. People aren't just attracted to you because you're a random person. They're attracted to you because you have something to say that really connects to them. And I think that is something that founders are often lacking.

9:45They know the product that they have and they know the problem that they're trying to solve, but they haven't exactly thought about their own personal point of view and how that can connect to an audience as well. It's something I often encourage founders to do, which is to draw a line between what is the problem that your product is solving and who is it solving that problem for to How can you solve a version of that content for that same audience with content? And I'd love to hear you unpack that a little bit more about how to find that point of view and how to find a point of view that connects to an audience and then maybe create the kind of feedback loop that helps you refine what you're saying to really maximize that connection to the audience.

10:27Yeah, I think, Jason, to your point, like people are scared to have a point of view. because it's been a time where a point of view can get you in big trouble. But I think the pendulum is swinging when it comes to a point of view. I think if you don't have a point of view, you're going to get eaten alive. If you're just playing neutral in every scenario, to me, that's boring. I don't want to go to a dinner party with someone like that. And I don't want to have them on the podcast. And I'm just being radically honest. I think people want people in this day today to show up as who they are. Personally, I think everyone has a point of view.

11:05It just depends if you want to share it publicly or not. If you don't want to share it publicly, I think that's fine. Double down on the product and make the product bigger than you. And it doesn't have to be about you. But if you do want to build a community and you do want to build a personal brand, I think that's going to become more and more popular. You do have to have a point of view. And to me is how do you find it? I think everyone has it in them. It's like an essence. I think you have to sit down and really think about what you want to stand for. There's a great book by Donald Miller called A Brand Story.

11:38Building a story brand. Yeah, a classic. You can apply that to a personal brand too. So you could build a brand story. It requires work. I think where maybe there's like a disconnect is people think you just wake up with it one day. I think that you have to really refine it and whittle it and figure out what you really want to double down on and what you don't. And again, you have to find the medium that you're comfortable to share the point of view. So if you're not comfortable on video, don't go on Instagram stories. If you're more comfortable behind a screen typing, go on Substack. There's so many different mediums that can fit with personalities.

12:15I think a good place to start is figuring out what that medium is for you. And a good way to do it is there's a book by Robert Greene called Mastery. It's a fantastic book to figure out what you're a master in. I also think like asking your parents and thinking about what you really liked when you were little. What are the things that you were gravitating towards, whether or not they made you money? Asking your childhood friends, like, what do they remember about you? To me, that's a good place to start. But it definitely requires some work, like a brand story and really refining it and branding your own point of view.

12:50How did you decide or figure out what your point of view was? And I don't mean just that you had things to say, but how did you define what the Lauren point of view is? I think I say what I mean and I mean what I say. And I'm not afraid to just be who I am. And I didn't realize that was maybe different until I started to put myself out there on social media. I've said this in so many interviews, but I know I'm not for everyone. I'm totally okay with that. I'm really fine with that. I've been like that since I was little. And I think just like talking about things that people won't talk about. I've talked about everything from vagina steaming to birth control to non-toxic products to boob jobs to plastic surgery.

13:43I've interviewed all different kinds of people from every different walk of life, from Chelsea Clinton to Ivanka Trump. I think where my point of view is, is I try to create a nonjudgmental space to hear other people's opinions, which allows me to express mine. And it started with a blog. But when I built the blog, I knew I was building a brand. And when the podcast space blew up, that was something I gravitated towards more even than the blog because I love to talk. And it made sense to have these conversations in a nonjudgmental neutral space, whether or not I agree with the guest. I don't agree with every guest.

14:21Just because I have them on the platform doesn't mean I agree with them. And just talk it out and hear what they have to say. There's no agenda being pushed. It really is a place to have honest conversation. And that's exactly how it started on the blog. Lauren, that's great and powerful advice. I want to put it next to something that I've thought about for myself, which feels like it could be in contrast, though I don't think it actually is. but I want to hear what you have to say about it, maybe how you marry the two. So when I got the job as editor-in-chief of Entrepreneur Magazine, it was really the first time that I was in any kind of public space and people were treating me like I was supposed to be a public person in some way.

15:03And I saw that as an opportunity, but I honestly did not know what to do with it. And I wasn't all that comfortable putting myself out publicly because who am I? Why does anyone have any interest in what I have to say? And then I came up with this idea that I call the 5 % character. And the 5 % character is this. I feel like, Lauren, you, me, everyone who's watching or listening to this, we are all 100 % people, 100%. But 100 % is not exactly relevant to the people that we want to reach. There are all sorts of things that we wake up in the morning thinking about, feeling that are not relevant to our audience.

15:34And so what would it mean to identify the 5 % of me that is most relevant to my audience and then just live that, almost create a character out of that. It's focused. It's intentional. And then once you think about it, you can start to think, well, OK, if I treat it like a character, then how does that character talk? How does that character think? How does that character move? What is the attitude of that character? Is that an optimistic character? Is it a pessimistic character? Is it an approachable character? Is it a too cool for you character? Over time, I developed this character version of me.

16:07And it's kind of me. It's a version of me. But it's not all of me. And I have found that to be really useful. But I also, when I tell it to people, they often tell me, well, that feels like the exact opposite of the advice that I usually hear, which is to be authentic and put yourself out there and people want to connect with you. And what you're describing, Jason, is like some kind of slightly inauthentic performative thing. But I'll tell you that it has worked for me and it has allowed me to wrap my head around it. How do you react to what I've just described? Have you done a version of that with yourself, even as you do this thing that you just described, which is you understand that you're not going to be for everyone.

16:47You've always been very comfortable sharing yourself. You are leveraging a brand that is all about authenticity. But is there a craftedness that you're thinking about for yourself just to give yourself almost a sense of coherence about who you're putting out into the world? I look at every single interaction in my life since I was little as I'm going to be on stage. I agree with you. I think that I want to show up and I want to perform. And whether that's on a podcast or a dinner party or an interaction at school with a mom, I like to turn it on. I also have another side of me that likes to completely be a recluse and be relaxing at home reading a book.

17:28But I'm more like you. I feel like what I do for a living is perform. So like I do feel like you need to bring your whole personality to it. I approach my job like a high performance athlete. When I am on and it is time to go, I want to show up 100 % effective, efficient, sparkly, whatever it is. And to do that, I have to have the opposite of that, which is like retreating, recharging, reading, meditating, walking, working out. I really approach it like an athlete. When I am home, I am preparing to go perform. So I'm actually swayed way more towards you. That doesn't mean I'm not authentic in the performance.

18:15Like the same person that you get here, you're going to get on my couch on a Friday night. But I definitely think to do what you and I do, there's definitely a performance aspect to it. And I try to refine the performance aspect in every interaction, whether I'm in an Uber or whether I'm having like an interaction in the hallway. I think there's always room to work on your craft in certain little spaces like that. As far as what you're saying, I also think how you approached it with like your 5%, it's like an octopus. Your octopus can have other tentacles and you can grow other tentacles. But what you just said about the 5 % is like the head, that's the brand.

18:55So I think starting there is really, really smart. And if I were to define what your point of view is, I think one of the things that's so cool about what you do is you're a practitioner of entrepreneurs. You've had access to all these incredible experts and people, and you've probably gotten your PhD in entrepreneurs. And that's unique. Not everyone has that. So do I think it's a performance? Yeah, it's a performance. I don't think that I'm, you're not going to get the same person when I'm like waking up in the morning. Yeah. That's interesting. What you just said there about me, which I appreciate is that was a consumer driven insight I felt at the very beginning of this for me, which is that as I was going out into the world, the kinds of questions that people were asking me were pattern matching questions.

19:44You meet so many entrepreneurs. What are the common traits of successful entrepreneurs? And after hearing enough of that, I came to this realization, which is that the questions that people ask you are actually them telling you what they perceive your value to be to them. And so if you take that seriously, then you start to think, OK, then I can build a product, even if that product is me, around what the perceived value is. So if people think I'm a guy who has access to lots of people like you, Lauren, who are incredible at what they do and can share their insights with me, then I'm actually the guy who just can process that and give people patterns.

20:20And I leaned very much into that with my 5 % character, so to speak. And so it's cool to hear you re-articulate that back to me. I want to take all of what we've talked about now and put it into that next phase of practice, which is you took this incredible audience, you've built tremendous brands with it, But you've got this Skinny Confidential Wellness and Beauty brand that was also built off of this audience that you have. And so I'd love for you to take me into how you think about this moment of introducing the brand to you. You said earlier, you build the audience first and then you introduce the brand.

20:59So how does that plug in in a way that excites people, that makes it feel like a natural extension of the enthusiasm that they already have for you? and where they're ready to participate. Yeah, I think I thought about it since I launched the blog 14 years ago. And I thought about what the product would be and what the brand would be. And I crowdsourced my audience, not for money, but for their opinion. I think of my audience as so invested in the development of the product that by the time that it's launched, they feel like they've been a part of every step of the way. And that's exactly what I did.

21:33So I knew I was going to launch product right when I launched the blog. and it took probably like nine years to launch it. And over that time, I could see what they were into. I could check my analytics. I talked to them every day in DMs. I would answer like 200 emails a day. I would respond to tweets. I was in the field with them. I wasn't like, I'm up here and you're down here. I was in it. And what were you waiting for over the course of nine years? What is the moment that you're looking for for launching? I was looking for what the right product was. If you've seen a lot of influencers, they just launch product and white label it.

22:09And so that's not what I wanted to do. I wanted to be very purposeful and thoughtful with what I was launching and why. The why is huge. And there wasn't a product that felt like it was sticky until the ice roller. The ice roller was really sticky. It felt very in line and synergistic with the brand. and the audience's feedback was like they were so excited, but there were so many pain points about the ones on the market. So I found a problem. I disrupted it. I made it better. I made it more beautiful. And I made it, I wanted it so when they got it in the mail, it exceeded their expectations. Like I didn't want them to get something and be like, oh, this wasn't as good as the picture.

22:54It needed to be better. So with that, it took four years to build the ice roller. took a long time. I was dealing back and forth with the product and the packaging and making it right for the audience. And I knew that once I launched a product, that there was going to be a tumbleweed of momentum. And I had to focus on that. So I had to have ideas after that and set myself up. So it was a very like long play. And now we've had the product line for four years. and every single product we've launched has been something that seamlessly integrates into the audience's routine and all we care about is that it's better than what's on the market and it's more beautiful so you want it out on your vanity so we just launched toilet paper everyone who is not in the community was confused by that but the people that have been following along were not confused at all i created something that is clean it's non-toxic it doesn't disrupt your endocrine system, your hormones.

23:55It's something every single person uses. It's a daily habit. And I made it pretty. It comes in pink. It's wrapped in pink. The box is luxurious and it's clean for you and your family. And it's something I'm passionate about. And I've been talking about non-toxic living. Basically, I was able to connect with the audience on a day-to-day basis and get their feedback in real time from colors to textures to their opinion. And they've essentially helped me build the product line. And that takes time. Does that take systems as well? You've got a large audience. So if you're in there in the weeds, responding to people's DMs, that's a lot of DMs.

24:31Is there a system that you have for tracking that, for identifying patterns? What are you doing? I was in my DMs for seven years every day responding. I've really watered the community. But after seven years, and you know this with what you do, you start to have to say no to get to the next level and to scale the business. So I said yes to everything for so long, and I was so available and, you know, screenshotting and asking questions and watching content and et cetera, et cetera. And then it gets to a point where it's like, okay, now I need to say no. So the systems that I have now look very different than the systems that I have then.

25:11If you're starting out, I would tell you to get in the weeds, get in the minutiae, do every single job in your business. I would tell you to hire someone to manage your time and really be looking at every single minute of your day and where you're allocating energy and if you're executing. But now my life has changed. It's like it has to be a priority for me to do it. If it's a no or a maybe, I won't do it anymore. I still, of course, connect with the community as much as I can. There's not like an AI bot in my DMs. I connect with them and answer them. And I also have hired people who work in the skinny confidentials DMs to make sure their questions are getting answered.

25:53But the systems are what get you to the goal. So a lot of people will have goals, but they don't have systems. You have to have systems to get you there. And that helps you execute. To me, a goal is just an idea. It's a flight dream. When someone tells me a goal they have, I'm like, OK, what are you doing to get there? So systems to me are one of the most important thing. And whether that's someone running your calendar, whether that's doing the Ivy Lee method every single day, whether it's putting an hour on your calendar to read every night, I don't everyone's systems look different. But I definitely have systems with every single thing I do.