Michael Bosstick on How to Build and Leverage an Audience

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1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show that solves entrepreneurs' toughest problems. I'm Jason Pfeiffer, Editor-in-Chief of Entrepreneur Magazine, and each week I take a problem that you're probably dealing with and get tactical solutions from people who have been there and solved that. So let's get solving. If I've learned anything from working in media for the past two decades, it is this. If you're just trying to sell content, you are dead. D-E-A-D, dead. Why? Because content is hard to monetize. It's hard to distribute. It's hard to get and hold people's attention.

2:13And it requires constant new, new, new, new. Every day, something new. Imagine having a business where your product needs to change every day. like reinvented from scratch, and you're never 100 % sure if your audience will like the thing that you made today versus whatever they liked yesterday. This is a crazy business. Why would anyone get into this business? I ask people that all the time when they talk about media, but that is why I have long been fascinated by Dear Media. Dear Media is technically a podcast company, but it thinks it's much bigger than that. Dear Media is, on the front surface, the largest female podcast network probably in existence, but we say that the Trojan horse into media was audio.

2:56This is Michael. I'm Michael Bostic. I am the founder and CEO of Dear Media. And Michael's thesis is this. Don't think of podcasts as the end goal. Think of podcasts as the starting point. Because if a podcast host develops a big following, then they can build a huge business on top of themselves, and Dear Media can help them do it and profit alongside them. Some of the best businesses are selfish businesses in a way. My wife, Lauren, and I started a podcast in 2016 called The Skinny Confidential, Him and Her Show. And it was just an audio show. There was no video component. There was no social element.

3:33There was no short form. It was just straight up long form audio. And we joined a company and quickly realized that they were underserving the ability for us to scale the way we wanted to. So when we left, we said, hey, these things are not just audio shows. They're shows. They need to be video. They need to be short form. They need to be long form. They need to be audio. They need to be in newsletters. They need to be on blogs. They need to be syndicated across every relevant digital media platform. And they're really just the launchpad to do a lot more, not just in media, but beyond in commerce and live events and books and streaming and you name it.

4:06So we kind of set out to build that space. And by the way, I was actually just on that podcast that Michael and his wife, Lauren, host. It is called The Skinny Confidential Him and Her Show. You should go check it out. I was on just a couple of weeks ago. It was a really great episode. Great time talking with them. I'm very impressed with how they run it. So Dear Media is their articulation of that big idea he just shared. And they're doing it at scale, not just for themselves, but for others in the creator economy too. They identify talent who can draw an audience and then help them build out that foundational show, you know, the podcast, that's also video in short form and blogs and all that, and then help them strategize the bigger picture.

4:46How does the show become a larger business platform? Where do products fit in? What about other forms of media? And in turn, Dear Media then becomes a place for talent to scale exponentially. It has 100 shows, making it a full creator economy ecosystem. And I wanted to know, what does that look like strategically? What process are they going through to look at someone with a podcast and say, okay, you could do this and then this and then this and then build out a brand that is far larger than just some podcast ever could be. And so that is what Michael and I are talking about today. If you are interested in the creator economy or just how to scale media or how to think differently about monetizing attention, this is a great conversation.

5:29We go deep into how media works and he walks me through some case studies from inside the world of dear media. And that is all coming up after the break. All right, we're back. I'm talking to Michael Bostic of Dear Media about turning people and their podcasts into full-blown brands and businesses. And I started by asking him, why audio? Of all the ways to build a name and a foundation today, why does he still believe that podcasts are a great platform for that? Well, the spoken word is one of human beings' oldest forms of communication. It's how we tell stories. It's how we connect with people.

6:10It's how we get our points across. It's how we learn things. And so I think innately, people are just receptive to this medium in general. They want to listen. They want to hear. I think it's one of the only places you can truly get to know creators and people that are speaking on a mic because you can curate content here on a blog or on a 60-second short form video content or 15 minute cut down edited version. But when you start talking on a mic week after week, day after day for long periods of time, you can really have deep conversations and you really start to learn how someone thinks, how they feel, why they think the way they think, why they feel the way they do.

6:44And so I just think that it is such a great way to build trust and engagement with that end consumer or that end audience. And so that's why we chose. And it also, I think in your answer there, you're reflecting this really interesting shift that I don't know if enough people are fully appreciative of. But let me tell you this interesting moment that I had as a guy who bridges these two worlds, traditional media and creator economy in some way. Okay, so years ago, we had Gary Vee on the cover. And this might have been 2017. I don't even know. and i thought that that story when it went online was gonna blow up and you know what it didn't and that is not because gary v is an uninteresting guy he's a very interesting guy but the more i thought about it the more i realized that the reason that story didn't blow up is because people get all the gary v that they need directly from gary v like they didn't actually need an intermediary to tell them about Gary V.

7:51They're getting him all the time. He's got a podcast. He's got every other thing. And what you're identifying is really that the more in which a person can develop a direct channel to their audience, the more invested those people are in that person. And then those audiences, consumer interests will just shift to whatever's directly coming from the person instead of what is coming through what is perceived to be an intermediary. So if you build the business in a way in which it feels like it's coming from that person, then the audience is much more motivated to engage. Yeah, 100%. And someone like me who does not come from traditional media platforms and had no background in media or in entertainment, 30 years ago, it would be next to impossible for me to do what I do now with my wife and reach the audience that we reach, right?

8:43I think like this medium in particular and the way that you're able to engage and reach that end person right away cost effectively basically afforded me the business that I have now and the living that I have now. And one of the things that I do running Dear Media as a CEO is that is a great pitch for people that do come from traditional media. What I tell celebrities or creators or people that come from reality TV is like, this is your mouthpiece that you control without any producers, without any kind of person in between, without any editing, without any filter, you can speak directly to this audience in the way that they or you see fit in a one-to-one way without having a bunch of people in the middle.

9:23All right. I'm excited to dig into some of the examples of how you build people's brands because what you just said there is at once true, but dot, dot, top, right? Which is to say that you're telling these creators, these celebrities, be authentic. And a thing that I think a lot of people who are trying to live in the creator economy to understand the creator economy, the thing that they get frustrated by, frankly, I think is hearing over and over again, well, it's just about authenticity. But in truth, it is really about authenticity plus strategy. And the strategy is often very hidden from people.

10:02But that is what you guys excel at. And so I'd be very interested in hearing you articulate how you start to craft that strategy. And then maybe we can dig into a case study or two about how you actually execute it. Sure. Yeah. I think the advice on being authentic was maybe relevant five or six years ago was like when people were starting to get into this and it's like, hey, it's not curated any longer. You have to kind of let the walls down. It's not scripted. Yes, you got to be authentic. I think now, I think if somebody came to me and they were like, well, I'm planning on not being authentic.

10:31I would say that's probably not the best place to start. It's kind of like someone saying, I want to work for you. And what are your qualities? Well, I work hard. It's like, well, that should be - Yeah, that's table stakes. Kind of like - It's table stakes. Yeah. So table stakes is authenticity, but you're right. I mean, when Lauren and I started this medium in 2016, it was very easy to stand out. I mean, hell, back in those days, people would look at me and say, what is a podcast and what are you doing? And I remember we used to create video graphics that you could put on social media platforms with a screen share or like a screen record showing where on your phone the podcast application was.

11:04Like it's that purple icon, you click it. Early days, it was a lot easier to stand up a show like ours with very little competition. It was like, you know, the Tim Ferriss's, the Rich Rolls, the Joe Rogan's, the serials, you know, early days of this medium is very hard to monetize. And now, you know, it seems everybody has a podcast, which is great for me and everybody is jumping into the medium, but it requires a lot more strategy now, right? Like you have to come in with a real perspective. You know, you have to come in with something that's different. Yes, you have to be authentic to yourself and give your audience a little bit more of an inside look on who you are and what you're really passionate about.

11:42Those are table stakes. But as it relates to strategy now, we're really thoughtful on what the go-to-market strategy looks like, what the guesting looks like. You know, we get down and figure out what is the studio, what's the cover art. We figure out what positioning, what brands, what does this thing actually want to be turned into down the road? Is it a product line? Is it a live events business? Is it going into a streaming show? What is the end goal for that creator? And then we really jump in with production support saying like, hey, how do we make this, how do we indicate that this is a project that you're taking very seriously, that is not a side business or a side channel.

12:19This is like a very big focus for your brand or your business. And then, yeah, we put a lot of stuff in place. Happy to get as grand as you like. Oh, yeah, I'd like to. First of all, what you just said there is super interesting. And I want to unpack one point of it before we move forward, which is the distinction that you were drawing between the benefits of being an early mover in this space and what is required now. Everybody who has an interest has at least 20 different podcasts to listen to, which means that if you are not entering a market, whatever it is, podcasts, newsletters, social, with a really clear articulation of the thing that you are doing for a hyper-specific audience, like what utility do you serve in their world, then there is just simply no way to break through.

13:06It's like it's a niche game now, not a wide game. First of all, do you think I'm right about that? I think you're 100 % right. It's funny. I wear kind of two hats every day in my world. I wear the hat as a host where I'm doing a show that you've been on. You did great on, by the way, where I get to talk to people all the time and there's an entertainment element and there's being curious and there's carrying a show and making sure that's in. And then the other hat that I really spend most of my time wearing is running Dear Media as a CEO. And part of that job requires me to be very intentional and specific about who we sign and the talent we work with and the dollars that we put up against those new shows or those new properties.

13:45And I will tell you, and without naming too many names, that we've met a lot of really big entertainers or celebrities or creators over the years that have huge platforms and other mediums that just don't translate into this medium. And it's nothing wrong with them. It's just, it doesn't just, just because maybe you have a big blog or a big Instagram account doesn't mean that you are right for carrying a long form talk show. Just because you've done well in one area of media doesn't mean that necessarily, maybe you're used to being interviewed and now you've got to be the interviewer. It's a different thing.

14:22I actually feel a little bit more uncomfortable doing this because I'm so used to interviewing people. I think I'm a better interviewer than an interviewee, if that makes sense, just because I have more hours and repetitions. First of all, the difference to me for what it's worth about being a host versus being a guest is that being a guest is far less predictable. You don't exactly know what the host is going to say. You don't know what direction it's going to go in. You almost have to carry more optionality in your head at the same time. So when I'm on your show and you guys are asking me a question, like I'm flipping through my head as fast as possible.

14:58Like, what's the right answer to this? What direction do I go? What story do I tell? Whereas if I'm the host, I know that I'm basically in control. I can drive it. It's like it's an easier role in many ways. So I'm curious what you look for. Let's leave aside like talent. Let's just say somebody's good on mic. What are you looking for to say this is somebody that we can build around? I'm looking for somebody first and foremost with a point of view. And I know that's broad, but they have to have a strong point of view. they have to feel a certain way about something whatever they're passionate about and they have to really kind of like stick to those convictions we've done we've you know at this point we have 100 shows but we've probably over the years have signed 200 you know like some make it some don't and what i've found the ones that don't really make it are the ones that kind of play the middle of the road it's like they're not really opinionated they don't really have a point of view they're kind of playing it safe they kind of you know whichever way the wind's blowing so first and foremost like what's your point of view and it doesn't have to be a point of view that we agree with.

15:56It just has to be a point of view. Then I think you have to be an entertainer. It's important to realize that you are doing a show that is for the purposes of either educating, inspiring, or entertaining someone. So you have to have that thing. I don't know how to describe it, but everybody knows what we're talking about. Someone that has that thing where you can look and be like, oh, that person's going to be someone. And then I think beyond that, it's someone that has a very long outlook on what they want to happen in success. Meaning like if someone comes to the door and they says, Hey, I want to do this for five or 10 episodes.

16:30And I want to make a bunch of money because I saw somebody else doing it. Like we're typically like, Hey, we're not the right fit. If somebody comes and says, I want to speak to this audience because I think this audience deserves this. And then one day it's going to turn into this or that. And this is the way I'm going to get there. That's what we keen into because we want to be helpful partners along the way. And obviously it's great to produce a successful podcast and monetize it in the way podcasts and vodcasts are monetized. But really like we're interested in what does the brand look like in four, five, six, seven, eight, nine, 10 years down the road.

17:01And that's what we're looking for. From a network perspective, we have a ton of data, right? We have a hundred shows, we see what's working, we see what's not working, and we're really in tune with the audience. So we may look around and say, okay, doing really well in pop culture, doing really well in health and wellness. Hey, guess what? Our audience, a lot of them are becoming new moms. We don't really have enough in parenting. Who's the best in parenting and what topics can we cover? Now we're saying, okay, what does financial literacy look like for the audience that we serve, which is primarily that millennial woman?

17:33And so we're able to go through the data and see categorically what we're missing. And then we go and try to find the best person in that space with the strongest perspective that wants to build a long-term brand. So here is something you sort of said, but I wonder if you would double click on if I put it in front of you, which is hyper specific value to a target audience that's underserved, which is something you said, but let me give you the example that's in my head. And that's Lenny, Lenny Ruchiski of Lenny's newsletter. But what's really interesting is at this point, Lenny's newsletter, for those who don't know, it's like the largest business newsletter on Substack.

18:11Lenny's newsletter has crossed the million subscriber mark, which is insane. But the way he did it was that he launched a thing for product developers. Like it was so hyper specific. And once he earned their trust, he was able to ask, well, okay, well, what else are they interested in? And eventually he got to the place where he's kind of a broader business publication at this point. But he started in this really specific niche way that I don't know anybody would have ever said, oh, yeah, Lenny, you can build like a million subscriber newsletter off of product developers, but they could. So I'm wondering with you, if you guys think the kind of niche and expansion like that, right?

18:52Like new moms is one thing, but then maybe also like new moms in their 20s who live in the Midwest is like another thing, right? Or like something that's like really specific. and then you get like a wedge in as a creator and then try to expand from there. Do you approach it like that? Yes. And this may offend some people, but my eyes glaze over when I start a new meeting with a talent or their agent and they say, hey, I'm going to be the next version of like a Joe Rogan. I'm going to be the next Mel Robbins. And like, I can be, and listen, I understand the comparison because these two people that I mentioned have tremendous success in the space.

19:27But what I always tell them is like, those people are already those people and they're already huge and they're doing well. what I try to push people towards when they come through the doors of Dear Media is like, what is the niche? And start there. And then over time, as you build the audience and they get more interested, then expand into different categories. Like Lauren and I have said for probably a decade on our show, it's an upside down triangle. It starts very narrow. In our case, it started as building a brand and a business online and taking audience questions. And for the first 30 episodes, just answering those.

19:57And then over time, yes, we introduced more of our relationship and we introduced more of guests. And then we kind of, now we're in so many different categories, it's insane, but that's a thousand episodes in. In the beginning, it was very narrow, very niche. And I think that's still in any online medium, the best way to stand out. I think if you're coming in to the internet in any kind of door and your strategy is to go wide and reach everyone, you're going to end up reaching no one. Right. Yeah, it's true. If anybody is listening to your show, they would be insane to try to copy your format.

20:27Your format that makes no sense as a new show. One day it's wellness, the next day it's business, the next day it's like, there's no way you could do that. It's talking to too many audiences. You can only do that by earning that audience over time. Yeah. And you're a hundred percent right. And what happens when you earn that audience over time is they may say, hey, like we get feedback all the time. It's like, I would have never chosen to listen to this person. It wasn't, you know, something that I thought I'd be interested in, but because we've listened to you or watched you for 10 years. We want to see why you found it interesting to talk to this person.

20:59And so you kind of, that's what happens, but you're a hundred percent right in the early days. If you had some of the, I mean, we had a conversation one time with a woman that was kidnapped by the Somali pirates and rescued by CL team six. It's a very interesting episode. It did very well. The audience loved it. But if I said, Hey, I'm going to launch a business podcast and that's going to be episode seven, people would say like, what are you talking about you know what i mean and so again like this is a decade in but early days i always say like what are those first 10 episodes look like and who are they serving the more niche the better honestly in my opinion right because at that point what the product has become is your sensibility like that's what you're describing there people are like well i'd like to see what lauren and michael found interesting about these people because at this point the reason i'm listening is because i trust them but at the very beginning it can't be about you it has to be about the thing you serve.

21:47Yeah. And we take the same approach with Dear Media, to be honest, that my thought with Dear Media is that, let's take show specifically, like I may win Jason's ear or eyes because I introduce you to a business podcast. But as you start to gain trust of the platform of Dear Media, just similar how Netflix does, you might also like, or YouTube does, right? Then you might see that pop culture or wellness. You're like, you know what? Because I trust this company and what they serve me already, maybe I will take a chance on those others. And that's how we think about serving new content to our audiences.

22:19Like, what are we kind of missing and how do we gain their trust in the first place? All right. Then you said this one other thing that I want to double click on as a means of getting into a case study, which was that you said that you're also thinking about what this can become at the very beginning, which is really interesting. And I think not something that a lot of people think about. So you're trying to game out a roadmap of sorts at the start of something. So maybe could you pick a show or a personality with a show and talk to me about how you would have forecast that at the beginning and then what you actually did to get there?

22:54Yeah. So I'll pick on my show first and then I'll pick on another show that we produce. Just because it's an easy example to pick on myself. So when Lauren and I started our podcast, It's Getting Confidential, at the time, and this is how old we are now. We thought that more listeners would equate to more blog readers, right? We're like, oh, if people listen to the podcast, they're going to go into the blog. And what we envisioned was by increasing the blog traffic, that would one day get us more eyeballs to then eventually get more clicks to a product line that she eventually did launch, right?

23:29And we thought, okay, the more traffic, the more engagement, the more trust, the better that we'd be able to build our own brand and our own product line. And with that product line, we'd be able to have our own kind of like media business and consumer brand, which we ended up doing. Little did we know that kind of like it flipped the other way and the podcast became the thing that then led to the product line. But there was always a roadmap with her and I saying that we want to be more than just media. In our case, we wanted to launch a consumer brand. We wanted to be investors, which we are now in many other brands.

23:55We wanted to have a platform like Dear Media, where we could help other creators and invest in their brands. But it started, there was never an intention with her and I to say like, we just want to be podcasters. As a matter of fact, we never even cared about monetizing the podcast for the first two or three years. It was really just a hub to do the other things. And so I think that intentionality and that North Star led us to be able to then create Dear Media, to work with other talent, to help them start their brands, to invest in her consumer brand, which Dear Media was a lead investor, and then have her product line.

24:27In relation to that, we work with, there's a show called The Toast. When we started working with them, we found a phenomenal show. we thought, okay, they could do more with video. They had ambition to launch their own business, which is in this case is called Spritz Society. It's a canned cocktail. Dear Media and Lauren and I both invested in that. The network helped stand it up and support it. They're doing more in live all the time. So that's another example of like, there was more than just serve. Of course we sell their ads and we're their media partner, but how can we also help them build their own business?

24:56As we think about other creators, the way that we talk to them is we say, okay, in success, when this show works, what else do you want to do? I've seen so many businesses lose creators or celebrities to other platforms because they're not saying, hey, let me be your first stop. When you want to go build that business, or you're looking for an investor, or you want to take your show on the road, or you want to write that book or create that TV show, they typically go outside of their partner into somewhere else and kind of start from square one. So for us, we say from the beginning, like in success, we want to be your first stop.