Becky Mollenkamp (00:00)
All right. Because these replays will be available to you end of day each day. So if you can't be here for a session, don't worry, you'll get your replay. again, the upgrade bundle is just to get all those amazing extra goodies that people threw out, but the replays are included with your general admission tickets. So you won't miss anything. people are coming in because we're just at that half hour mark, so make sure I get people in for that. and so, Anna. Hello.

Thank you for being here. So Anna is an OG FPC member, helped, you know, start one of the original fifteen, I think, to get this thing off and running. And then Anna got too big and busy for us. I totally got it.

Anna DeShawn (00:41)
That is not true. About the big part. Busy, yeah. Yeah, I missed you all. I follow the emails though.

Becky Mollenkamp (00:48)
And we miss you. We hope we get to see you back. But everybody's it's Anna, we haven't seen you in a while. Because your show and you are just out there and doing it and like showing up in all the places and taking off and just opportunities abound. And obviously, when we see that from the outside, we think, how does it all happen? So that's what we're gonna talk about today. Before we get too far into that, though, let's start with like your origin story. Tell us what your show is, also what E3 Radio is, because that's outside of the podcast, how those things kind of relate in.

Came about. How long have you been doing this?

Anna DeShawn (01:20)
100%. and once again, Becky, thanks for having me. It's good to be here with like-minded folks just trying to make a difference wherever we can, right? Anna Deshaun, pronouns, anything respectful is amazing. I just from South Shide of Chicago. Always wanted to be in broadcasting. My parents put me in broadcast camps when I was a kid. I remember going to Bradley University for a journalism camp and cutting tape and telling stories. Robin Roberts is my North Star. Anyone know her? Let me know. Okay. Love to meet her.

Wouldn't have to do anything else for the rest of my life.

Becky Mollenkamp (01:52)
I don't know how this hasn't happened yet. I'm still in shock, but Maggie it's good.

Anna DeShawn (01:56)
I can't even tell you how many times I've come this close. It's been like this close on a number of times. but I'm just waiting because when it happens, it's gonna be so perfect and so divine. And then just catch me on the other side, friends. I'm just gonna hang it all up. That'll be all I need to do. went to school for radio television production, journalism, multicultural studies, got my master's in communications.

And took an untraditional route when I realized that maybe a mask presenting person is not going to be on air talent. Ended up really falling in love with radio. And I decided that that was the way I wanted to go. Also decided I couldn't do small markets because I needed to come back home to Chicago ASAP. I had spent four years in Des Moines, Iowa at Drake University and then went to Ithaca, New York for another two years.

where all of that mess with Cornell is happening, and decided I could not go the traditional, you know, journalism broadcast route. So I came home, got corporate jobs in communications to my parents' surprise, and have been doing that work ever since. And when I in 2009, I started E3 Radio, which is my online radio station where we're playing queer artists all day long. And from that work

I started a podcast called Queer News. We're in our fifth season now, and that falls right in alignment for when I quit corporate America. And so I decided to take a step out on faith during COVID, like so many other folks. If the world's gonna start over, why not me too? And I've been on this wild roller coaster ride ever since. And and a roll wide roller coaster ride is what it is.

Becky Mollenkamp (03:47)
So you have the Queer News, which is your podcast, and then E three radio, which is like the umbrella that has your podcast and others inside of it, right?

Anna DeShawn (03:58)
Not at the moment. No. So there's two entities. So E3 Radio is the radio station and Queer News lives there. And then I have another company called the Cube, where we produce other podcasts and those podcasts live there. that entity, the goal is to be the dopest search engine for black and brown podcasts.

Becky Mollenkamp (04:18)
Can you, while I ask the next question, drop your links in the chat as well, or maybe also state them out loud for people watching the replay? Because obviously we've got Stephanie saying, hey, how do I how do I listen? I want to listen. Because you have constant programming. It's like it's an online radio station with E3 radio where there's all constant programming between the podcast part and then music and other stuff. So what made you want to do that part? Cause you start did you start with the podcast or did you start with E3?

Anna DeShawn (04:44)
I started with E3 and it started with a show called the Anna Deshaun Show in November of 2009 with an organization called Gender Just that doesn't even exist anymore, child. so it started there and and then I began producing other shows that were a part of E3. We were on Blog Talk Radio, if anybody remembers Blog Talk Radio. and I love radio. I still love radio. You're ahead of

Becky Mollenkamp (05:12)
Podcast. You're ahead of the curve on podcasting. Two thousand nine. That was really early.

Anna DeShawn (05:16)
It was really early. We had an RSS feed at that time because it was all online. And it was just a there was a need. And I and I at the time I wasn't interested in necessarily doing just LGBTQ content. I actually have a had a conversation with a homie and we talk and laugh about it today. Cause she was like, Anna, we need a queer radio station. I was like, I don't want to do that. Because the moment people hear queer, everything else goes out the window. I got like all these intersections that I wanted to amplify. And she was like, no, Anna, we really do need one.

And I was like, nah. And so back then my logo didn't even have a rainbow in it. It was just white and purple. And then I started doing the show and I realized everybody was queer. No matter what I thought I was gonna be doing, everybody I had on that show was queer. And it became evidently clear that that's exactly what I needed to be doing. And so then I filled in my radio tower logo with the rainbow, and we just been queer ever since.

Becky Mollenkamp (06:10)
And now that so you've been doing queer radio or queer news, sorry, for quite a while now too. Yeah. And I know you have both things going on, so it some of this is gonna overlap on the opportunities and that you've created, because I don't want to say they're just coming to you that you've been creating. It it overlaps with both things. But what role has the podcast played specifically? Like how much of what you do is on the podcast versus like the radio piece?

Anna DeShawn (06:37)
It's not even even. It can't even equate in this moment. here's to being able to build something that's financially stable where I can invest in somebody being a program manager for the station piece and who can invest time in the music part. Cause there was a point in my life where I listened to a lot of music and a lot of independent music, but that is not where I'm at in this moment. And so the podcast has really taken off. it's taken me to places I would have never thought.

It's open doors and that weren't opening with just the radio station. And it became clear also where people were going. People treat radio differently than they did back in 2009, right? Like people like to just listen whenever they want to listen. No one's tuning in at a certain time to catch, you know. When I was growing up catching Tom Joyner or Doug Banks or some of these other iconic radio folks, that's just not how people listen. So the transition to podcasting was necessary.

And then and now the podcast is just taking off on

Becky Mollenkamp (07:40)
Which is great 'cause that's what I really want to focus in on. So that's if people want to know more about E3 radio, check it out. I'm sure Anna would answer questions, but let's the goal is really to think more about podcasting because that's who we have in the room as podcasters. And you absolutely thank you. And Rachel so lovingly also put that in, which I appreciate. her support. Yes. you reluctantly started the podcast or started a podcast and reluctantly took the direction it's going that it's gone in now.

What changed when you made that shift, when you went from sort of Anna Deshaun to queer news?

Anna DeShawn (08:13)
Just the intentionality behind it. It's so, you know, the radio piece was great. And so when I quit corporate, I actually started a show called Anna Deshaun and Friends. And I was going live every Monday morning for about three or four hours. And I was playing queer artists and I was doing queer news, but it stopped bringing me joy. And it wasn't getting the results that I wanted. And I'm never gonna stay doing something that's not working. Like we ain't we aren't we're not doing that here. We're gonna pivot, change, figure out what's working.

And experiment, right? Because it's okay to fail. Failure is cool. We're good with that. We've been through therapy, healthy Virgo here. Okay. So it's cool to fail and then move on to the next thing. And that's what happened with that radio show. I ended up going to two podcasting conferences, Podfest and Afro's and Audio. I left both of those conferences. Like, I'm gonna take the segment that I enjoy the most that I think is most unique and turn that into a podcast. So the queer news I was doing on the radio show.

That's how the podcast was born. and so that's what happened. It came out of a pivot and it's probably been the best pivot I've ever made to be honest.

Becky Mollenkamp (09:22)
And that's so two thousand nine is when you sort of started all this. When did when was career news as we know it now? When was it sort of

Anna DeShawn (09:28)
Twenty twenty one?

Becky Mollenkamp (09:30)
Okay. And then FPC started like twenty twenty three or four and you were one of those original folks. And at that time, like I think you were you were always busy and doing a lot. But I feel like the amount that has shifted just even in these last like two, three years has been amazing.

So first of all to say it takes time. Yes. Right. And because I think that was something that came up in the first session, this sort of like, how long does it take to build the community? When I feel like I'm speaking to Noah on the crickets thing that so many people are familiar with when they start. So can you talk a little bit about the first few years and did you ever have that feeling? Was it like, is anyone gonna listen? When did you start to notice some momentum and a shift?

Anna DeShawn (10:11)
I still had that feeling. Are you kidding me? I just did a live the other day. I think it was me and them and like two people. I'm glad those two people decided to talk a little bit. No, I I still have that feeling. For me, it is about consistency. Like every rep matters. So every time I do an interview with somebody, I'm becoming a stronger interviewer, right? Every time I'm connecting with somebody, I'm making another connection. And so for me, it is it is about reps. so

No, I still talk to nobody sometimes. I'm sure people, there are things people cannot find that they might even be looking for even in this moment. And it and it takes time because as you all have probably noticed since y'all started y'all podcasts, and probably I'm assuming most here are audio first podcast. The audio, the podcast engines that you're hosting on, whether it's lipson, Spotify for podcasters, captivate, all of the hosting, they aren't built to help you be found. They are not built.

To be discovery engines, there is nobody pushing your podcast out to other podcasters, right? Your podcast gets posted and then you got to do the rest of the magic. And that is what makes podcast growth so tough and challenging, is because the there is no like organic search or discovery engine in those platforms, right? And so the the last couple of years, there was some intentionality around me moving and well posting to YouTube first.

So every time I post a lipstick, it automatically posts to YouTube. Also being more intentional about doing videos that honestly I don't like to do. I don't like doing them videos. I would love to never have to do a video. I wish I could just do my podcast. People would listen and love it. And then I would never have to, but that's not the case. So posting the short videos about the content that we're doing on the podcast has been a game changer and doing it consistently.

is what's so important there and recently transitioning back to doing interviews. So when I first started in 2009, it was always interviews. Always. I was always interviewing people. And the internet makes the world small. And sending DMs to people and asking they'd be on the show and people responding is really how I grew the show in the beginning. But when I started queer news, it became about reporting on the stories and it became less about interviewing people.

but during these interviews has gotten me back into the groove of being in conversation with people. And that just it just helps grow your show. They're gonna share it and now with Instagram and collaboration posts, YouTube and the collaboration feature now on YouTube. YouTube's related like video options, short to long form has also helped tremendously. So

pivoting, expanding. I can just keep doing that to try to figure out how we grow because the audio part, it hasn't grown the way YouTube has grown, right? And it and honestly, it never will unless they change how they choose to host or show up in the podcasting space. Right. so those are things that have that have helped me grow.

Becky Mollenkamp (13:27)
Yeah, because the search is like you said, it's not built for actual discovery. In fact, it's almost impossible to get found. I mean, it takes a lot of work. well, okay. So obviously opportunities have been come I I hate saying coming because you're working for those opportunities. So I don't want to be like, these things are just falling on your lap. You're working hard to create opportunities, but I want people to know, like, you're like

I'm seeing you everywhere. Like you, first of all, you got to go to the Democratic National Convention, right? And be a part of that and the media there. And I want to talk about that. I've seen you've been on Under the Desk News, which obviously has a huge audience, and that's gotta be great. But these things don't just come out of nowhere. So before we get to like how those things came up, I want to go back to sort of even what are some of the things that you notice? I mean, you've talked about a few things, but I know like you were doing years ago, you did some listening parties, and that was something you had tried. I know you were trying to get out and speak in more college campuses.

W you are somebody who's been thinking outside the box from the beginning and trying to think about what are all the ways I can approach this that aren't just relying on, hey guest, I hope you share my show or I'll post on social media and hope people find it. And I don't mean that as a slight to any of us because that's what most of us do, because that's just kind of what we're told. but you've been thinking about what else? What else? Like I feel like that's always been the way you show up is kind of thinking like, what else? What else could I try? I haven't thought about this, what about that?

And I think it's b really been working for you. So what are some of the earlier examples of that? What are some the first things you started to notice like, mm, this is something that seems to be making a difference? Like what moved the needle earlier on?

Anna DeShawn (15:02)
Is really understanding that it's a business. Right. So it's funny, I just heard a content creator say, You can grow followers all day, but do you have a business model? Because the followers is not gonna get you paid. and so I've when I quit corporate, I needed to survive. I just want y'all to know I got an expensive wife, okay? A needy dog who don't eat normal dog food, okay. And

Got a mortgage I need to pay, so I can't live on just a dream of being great here. I'd actually need to bring in money. And ending my corporate career in sales was the best preparation I had for actually being able to survive this moment because being a creative is great. I'm I will always have another idea that is going to come to me when I sit in my prayer corner in the morning. Okay. I I have lovely ideas.

But how am I gonna make it make some money for me while also doing good in the world? I always consider myself a social entrepreneur. I'm not somebody who's just trying to feed on the capitalism of it all. But I need money so that I can use it as a tool so I can keep doing my work. And I'm living at a time where we all know we in the Trump administration. This it's crazy out here. Money, the defunding of diversity, equity, and inclusion. my whole podcast is called Queer News. When I got into the business, business side of this podcast and work.

And understanding how advertisers are finding podcasts to advertise on and these algorithms and these AI tools that they're using. Queer is like a bad word. Child, they can't run their ads on things that get dinged. My podcast was getting dinged all over the place because queer was a bad word. Right. There was no way any of those better helps or anybody else is on the top. Neandies, these people were ever gonna advertise on my podcast for fear, right?

It was going to get a ding. And so when you get to understanding how that whole business side of podcasting works, I was clear that I needed to make up my own rules, understanding the value of my own audience. I'm reaching queer folks, certain age, certain demographic. They have incredible value to any advertiser, right? and so being able to figure out how I'm going to sell my podcast, and it's never been just about selling ads on the podcast.

Is it been about the podcast? Is it been about social media? These are packages, child. you wanna send a note on the newsletter? it is about a package, not just one thing, because I'm not getting a million listens on a podcast episode. That is not my reality.

Becky Mollenkamp (17:39)
And just to clarify quickly, the CPM model that's mostly used in advertising for media, which is cost per million, is or well, cost per thousand, actually, is what the is cost per thousand is for every thousand downloads, typically you get like a do ten dollars. And I think that's actually a super generous CPM, honestly. So, like for most people, most of us, most indie podcasters, that model just doesn't work for us. We can't rely on advertising. Meandies and those like you have to have an a

giant audience to reach that kind of level that most of us won't. And so you've been exploring what does it look like to look at sponsorship from a different way.

Anna DeShawn (18:13)
a hundred percent always from the very beginning. Like, can we sell you a whole package? So because people have to see a message like 10 times to take an action. So if I send it in my newsletter and then put it on the podcast for this month, right? And run it every month. And then I do a video about it on my socials. People who are fans of the show and of the work, they'll see it multiple times. And then maybe there's a potential for them to take an action, right? I also got great advice from a homie who is still doing like

commercial radio. And she was like, Anna, you gotta look at yourself like a local radio station when it comes to advertising. And that for me was also a light bulb because oftentimes we are thinking we want to reach everybody nationally. I mean, that's the power of the internet. We can reach everybody everywhere. But there's also power in just saying, I'm focusing on Chicago. And I can then leverage the relationships that I've built here at home.

To say, hey, do you want to buy an ad for 200 bucks? Because that's gonna help me cover this bill I got, right? Like, help me cover hosting, you know, for X number of time. That's what I'm thinking. But I have a better chance of leveraging a relationship I got here at home with a small business than I do trying to say I'm here for everybody, everywhere. And so that has been a game changer for me as well, because I'm outside.

For me, it is all about relationships. Even when it talks about growing this podcast, and you talk about the DNC. child, I cried that day. That first day I was at the DNC, I cried. I called my wife, I said, What am I doing here? Okay, I am a solo person with my my tripod and my phone and my mic, and I'm surrounded by CNN and MSNBC, and they have camera people, even

larger social media stars who've got their producer, their assistant, somebody working camera. And I was there by myself. And my wife got me right on together. We we thank her for that. But it I I definitely had a whole moment when I sat there because it was just all kind of overwhelming to be in that space. But it was also a great experience. It was a wonderful experience to be there when Kamala decided, you know, when she accepted the nomination. And so to be there.

At the United at the United Center for that moment, it was huge.

Becky Mollenkamp (20:35)
Well how did that invitation come about?

Anna DeShawn (20:38)
So I how did that invitation come about?

How did I get to the DNC?

Becky Mollenkamp (20:45)
It's been so long now. I mean I'm sure it was relationship.

Anna DeShawn (20:47)
Yeah. You could apply.

Becky Mollenkamp (20:51)
Mm, okay.

Anna DeShawn (20:52)
You could apply to be at the DNC and I applied. and let me tell y'all, I apply to a lot of stuff and don't get it. so I applied and I got a credential for it. And and that was fantastic.

Becky Mollenkamp (21:05)
Is that where you met is it V who does under the desk news? I thought

Anna DeShawn (21:09)
It is because other

Becky Mollenkamp (21:10)
that was Is that where you met them or how did that relationship start?

Anna DeShawn (21:14)
No, that was TikTok. That was all TikTok. So I I was posting on TikTok, V post on TikTok, V started following me. And then of course I was already following V, like the other million people that follow V. Or more. And they would comment sometimes on my content. But then I ended up getting an opportunity to go to the Victory Institute. and if no one's familiar, they help LGBTQ candidates from around the country get prepared to run for office.

So if you're queer, you want to run for office, they have like trainings and all these things you can prepare for. And then they give you the resources to help run for office, federal, local level, all the types of things, school boards, everything. And so they were having their normal convening. I got asked to go there and work the red carpet and do interviews. And I got to meet V in person there. And it was so dope because if if you've seen any of my content, I always start with family. And so when they saw me, they were like, family. And I was like,

Man, it was a whole moment. So V is fantastic. And they've always said, like, Anna, if you need anything, you need to come on the show. If you need me to cross collaborate on a sub stack, I'm here for it. And honestly, that has been my experience with content creators out here who are really trying to change the world in their own way. Folks have been really supportive and kind.

Becky Mollenkamp (22:40)
And has that relationship well, first of all the Democratic the DNC and that event and then also this new relationship newer relationship you've established with B and Under the Dust News and being on Under the Dust News to do some commentating and whatnot. What has that done? Has that made a shift in your own listenership? Are you noticing differences from those kinds of bigger relationships?

Anna DeShawn (23:03)
Yeah, ch you gotta be what is it? What are you? What's the good word here? validity. the show that you're like legit. So when you're independent, you don't have a brand behind you that people trust. You have to become the trusted brand. And then other people's brands that they trust, then they trust you. That's the sort of the game we play here. so as an independent person without a

major network to back me and say no, we've all verified that this person is good. When I connect with a person like V, who has a huge audience, yes, but who is also a trusted source, then folks begin to trust me. Like that's how this works. And so yeah, absolutely. V being on V's lives have helped grow my reach and my audience. I'm also I'll say this, I'm clear about my goal in all of this.

Which is to be a queer news correspondent, to be somebody that folks go to when they're looking for queer news information. And so being a guest on V show allows me to be a queer news correspondent for V, because V covers everything. They are queer. Yeah. But V covers po politics. Which

Becky Mollenkamp (24:17)
Right. Which is which is everything.

Anna DeShawn (24:20)
is everything. Right. and so for example, I also got an opportunity to be on City Cast, Chicago, which is a news.

Podcasts here, and they actually are across the country. they're a daily newsletter and a daily podcast. So I'm the queer one. I'm one of the queer ones, but I do queer all the time. So I'm a queer news correspondent now on City Cash Chicago. And so my hope is that to continue to grow the show and my profile. So one day I'll be on CNN and be like the queer news contributor on a CNN situation. Or do I want that anymore? Child, it's sketchy out here.

Becky Mollenkamp (24:57)
Okay. Somewhere.

Anna DeShawn (24:57)
I know. but

to be somebody that folks can trust about this particular new like news and community is one of my goals. So collaborating with folks who are in that space or who are reaching that audience is the goal.

Becky Mollenkamp (25:17)
Well, politics girl does CNN and we need we need good folks on CNN to fight the battles if you're able to do it. So who knows? But well CNN's changing ownership and it's not good. But anyway. We'll have to get too much into that, Stephanie, but you can read about it. New ownership and and same

Anna DeShawn (25:34)
Mainstream media.

Becky Mollenkamp (25:35)
Yeah, it's all problematic. okay. Thank you, because what I'm hearing from you is relationships. Relationships, relationships, relationships. Which again, we talked about in the last

session with Andrea Jones, who's talking about building community. And it's all about those relationships, which I think we get really focused on download numbers, but each person presents some real opportunity for relationship and collaboration and expansion. I also hear from you just again, it's this creative thinking of thinking about local, thinking about what can I apply for, where can I reach out? Who can I talk to instead of sort of this like if you build it, they will come sort of scenario. What

Anna DeShawn (26:13)
said that. Was that just in the movie?

Becky Mollenkamp (26:16)
I think so. Was that from was that from the Yeah, that's it. Which is

Anna DeShawn (26:18)
Build a dreams.

Becky Mollenkamp (26:22)
speaking of Iowa. this is actually how Anna and I met because we both went to Drake, me much before Anna, but anyway. and I reached out 'cause I'm like, hey, we're both Drake alone. Anyway, okay, but I still I feel like we're talking a lot about now and I I'm looking for some more like just practical tactical things that you remember doing over these last few years leading up to some of this.

That 'cause I mean, as an example, the listening parties. Did they work? Did they not work? What did you take from that? Were there other things that you can also point to, like specific activities that you did that you say, that really moved the needle?

Anna DeShawn (26:58)
yeah. I I went in debt. Are we ready to talk about good debt? Because I talk about that. because I had to invest in myself. Now when I left corporate, I had set up the plan and I saved all the money and all that good stuff. And it went really, really fast. And one, but one of the things I knew I had to do practically was connect with all the people who I felt like were building community with folks who I wanted to be part of their audience. Like I needed them to be part of my audience. So

I began to research everybody in the podcasting space who was making moves and building community because I wanted to connect with them. So that included the Black Podcasters Association. You got Lauren and Ariel on. that included places like Afros and Audio. at the time there was BIPOC podcast creators. they've since disbanded. There was she podcasts at a time. I feel like she might be coming back.

Becky Mollenkamp (27:52)
Yeah, L C has already spoken inside of F P C and Jessica is speaking in like a month inside of F P C so yeah.

Anna DeShawn (27:58)
Okay, yes,

she podcasts. and so I intentionally connected with the creators of those spaces to share what I was doing, to share what I was interested in doing and building relationships with them because people protect their communities. So you can't just be up in here posting a bunch of stuff and think that that that's gonna fly. You have to build relationships with the folks who are creating. So that was the first tangible thing when I quit corporate, was I did my market research and I wanted to connect with the people who were making moves.

and that's exactly what I did. And the next thing I did was I went to the conferences that were happening so I could connect with them in IRL because and this was during COVID. So child, people knew me because I had a mask on with my logo, and I was just I was just everywhere connecting with people in real life and also applying to speak at those conferences. and then I got accepted to speak at those conferences. So podcast movement. it was funny. The first time I got accepted to speak there.

I was in the last slot of the last day, the day that everybody is already flying to go home. And all and the friends I had made, they stayed to hear me speak that day. and so that was another thing I did showing up at the conferences and applying to speak and networking there. That was huge. And I and I did that. This was the first year I haven't done the whole conference circuit. Money is tight.

I needed to stay at home and reevaluate how I was making money just because of the huge disinvestment. And so this is the first year I haven't done the whole circuit of the traveling to a podcast movement or traveling to an Afros and audio or

Any of the other ones that resonate that's happening now in October. so that was another tangible thing that I did.

Becky Mollenkamp (29:50)
When you look at your listenership numbers over time, what are the activities that you think you can most relate, like directly relate to listenership? Is it being on being in other pe getting in front of other people's audiences, something like under the desk news? Is it about s being at events and those people listening to your show, like guesting on other people's podcasts? I don't what do you think are the things that actually

When you look at your numbers you say, I think this is actually what's bringing in the most listeners.

Anna DeShawn (30:20)
Well, another tangible thing I did was apply to awards. And so, you know, the one of the first big bumps I saw was when I won the AMB for queer news in 2023. That was like one of the biggest jumps I ever had. Right. And so I also intentionally applied to award shows because if you get even if you don't win, if you get nominated, those lists are published. They're SEO associated to those lists. People send press releases out about those award shows. So even if you don't necessarily win, there are

Are winning elements to that moment that you can still gain a lot of value from. And it also adds to just like the validity of your show. There are hundreds of thousands of podcasts, but then you can begin to say, I'm a you know, award nominated, this nominated, even if you didn't win, nominated matters, right? and so that was another thing that I saw really bumped up like listenership from the audio perspective.

Guesting is the next thing for sure. I went on this podcast. What is that podcast called? Something gay. It's totally not my audience. It's a whole bunch of like 40, 50-year-old white gay men. And they and they caught me on a Saturday. And I was heated that morning. They caught me so I was not centered at all before went on that show. And I probably got the biggest jump in listenership.

after the ambies after being on their show. And I was thinking to myself even earlier this year, like I should go back on that show. I wish I could remember the name of it. But I actually had people messaging me saying I heard you on this show and now I'm starting to listen to your podcast. so guesting on other people's stuff is another big way.

Becky Mollenkamp (32:05)
Yeah.

And first the award thing I want to say 'cause a couple of people have s asked a few things or said a few things about that. One, sometimes y these award things you're paying to apply. And that paying is so that because they have money that goes into their whole you know

creating the awards and hosting a thing and you know getting judges and all the stuff, right? And marketing it. But it is interesting to think about. They also, some of these awards that are really established have been around a long time, they do have that SEO. So even if it's not about winning, it's about the the what is that called when you have like, God, I hate paramenopause. But like by association, where you get, you know, notoriety not notoriety because it's bad, but you know publicity by association. Anyway, somebody

Anna DeShawn (32:49)
Free PR. Yeah, and so they are expensive. Yeah. So

you have to choose.

Becky Mollenkamp (32:59)
And that you're talking that investing in yourself and thinking about that. And Candace, who's a member has also like recently won an award and what you know, is backing up what you said. Yeah, it's that SEO bump. So sometimes I think we look at those awards, we think, You want me to pay? Forget it. I don't need your recognition. Screw you. But you're actually what if you switch your thinking about it and think, No, I'm paying for your SEO, I'm paying for the publicity, which then can help to relate to audiences, which is great. And then being on other shows is something we definitely encourage inside of FPC, obviously as well.

Anna DeShawn (33:29)
Yeah, definitely it's definitely a line line up in your budget. And it's definitely something that you have like know when the early bird is and do the early. Like I just missed the early for the Ambies and it was on my calendar. I'm real mad at myself about that. But I'm still gonna apply to the Ambies. it's the one award show that I will apply to every single year. You have to be a member of the podcast academy. They set it up like the Emmys. It's like winning an Emmy for the podcasting space. Yeah. So the Ambies are one that I will always apply to. But

There's also so many others that if you catch them early on, they won't be as expensive.

Becky Mollenkamp (34:03)
As you mentioned, Black Po Black Podcasters Association, I know they do awards and there are others as well that you can just search

Anna DeShawn (34:09)
Sure.

Becky Mollenkamp (34:11)
podcast awards and you'll find some. And most of them, if you research, you can find when their application period is. So that's great for you to share. I wanna I so those are things that have really helped you start to grow your audience. I wanna talk about because Stephanie also asked about this disinvestment around

your key sort of search words and the things that you have built this audience around, which in some ways I would think the leaning into that very specific audience has been incredibly helpful for you. And I think you would probably say that it's given you some direction on and and like the you're known for, like you are this person, right? So that helps you stand out. And even in this time where there is that disinvestment, along with that comes more conversation where you become that go-to person for those conversations. So there's some upsides to it.

The downside is the financial side of that. And so I want to talk a little bit about pre-2024 and a lot of what we were saying with disinvestment and then post that. because you mentioned creating like bundles, like sponsorship opportunities. What have those looked like for you? What has worked to bring get some of those people in and actually, like you said, paying money? Cause for a lot of us, that's what you know, we'd we'd like to make some money, whether it's high getting clients who find us through our shows or saying, hey, sponsors.

Come help me offset some of these costs or maybe even make some money. What work to get them on? And then we can talk about the like what's been changing.

Anna DeShawn (35:35)
So you just gotta you make a list. I'm a Virgo. There's an Excel list for everything in my life. You really do have to take inventory, true inventory of your contact list, whether it's just opening your phone and literally looking at people and saying who owns a business here or who's looking maybe who to also promote, and doing true just sales work. It is about reaching out and

not being mad about a no, which is really hard. Like I hear no so much. That's why I got a prayer corner for real. Because you you can it's easy to begin to question yourself. but this is my full time thing. And so I know for like I have to make 10 asks to get a yes. Right. So and the tip pretty

Becky Mollenkamp (36:28)
That's

Anna DeShawn (36:29)
good. It's still pretty good. Yes.

And it's hard to be vulnerable in that way all the time, but that is what this work requires. And so, you know, even pre 2024, it was really about it's just relationships, like who owns a business, who am I already supporting, who am I already telling stories about, who am I already talking about, who am I already reading, who am I already wearing, where am I already going that I'm already investing money into? Like.

I'm going to the gym. Can't the gym buy an ad? Yo, I'm paying to go here. Can you can you pay to, you know, for a couple of ads on the show? just really just take an inventory of that and doing sales 101 type of work is what has helped me. I will say post 2024, last couple of years, especially and then post-COVID, adding IRL plays.

to the packages helps tremendously. It's really challenging to sell digital only. Digital only is a tough sale, no matter what. So being able to say, I'm doing this listening event, would you like to be, you can add in that as a sponsorship opportunity, or I'm doing this meetup event, adding that as a sponsorship opportunity where they can say or feel like people touched a flyer or, you know, or felt like they saw their brand in real life.

Adding that to my packages has helped a lot.

Becky Mollenkamp (38:03)
Well, and I because Candace was asking I think she understands it's in real life, but I'm curious what kinds of things you've been able to do, if that's events, if it's something else. But but it it you just mentioned one thing I also want to touch on, which is the packages, because you were sort of saying take inventory and I think it's so important to be able to clearly communicate what they get for sponsorship, exactly what's involved, right? So that because I think many people don't even think that out.

It's just like, put your ad on my show. And it's like, okay, what does that mean? How long? How often? For how long? How many episodes? You know, and then also what else? Because an ads one thing, but what else could you bundle that with? Right? Can you put it on the website? Do you have a newsletter? Are you gonna do some social media posts? In your case, maybe you're doing something in real life where you mention them or an event like this where you mention a sponsor. So thinking through what your package actually is is really important. And what are the in real life kinds of components that you have worked?

That that have been appealing for sponsors in your area, for anyone who's doing in real life stuff.

Anna DeShawn (39:00)
Yeah, y'all, ever since these storms, my internet has been messed up. hopefully y'all can still hear me. Yeah. All right. so the IR, the in real life stuff have been the listening events. So I have an event called the podcast salon that I host where we take a creator, we take silent headphones, they give me clips of their podcast, we listen to them as a community and then we talk about them in real life. people have

Loved our podcast salons. We then took the podcast salon and put it on vinyl, which is really, really dope as a way to preserve our stories. so people have really liked those. and that has been my primary IRL event are the salons. I've been really trying not to overdo, like I've really been trying to give myself time to try something for a little bit.

And then if it's not working, then pivot, but the salons have been working. And so my goal has been to try to do it once a quarter with some type of level of consistency. And so that's what I leaned into. At one point I did a college tour, but that was child before 2024, and that's when money was okay. so I did like a six tour stop with the salons, DC, did I do Atlanta?

Denver. and so I did that and that was fantastic too. And I did an activation like a podcast movement one time for the for our work. and so sponsors like getting behind that type of stuff.

Becky Mollenkamp (40:40)
Yeah. And then do you send reports to sponsors afterwards, after an engagement with a sponsor? Stephanie wanted to know.

Anna DeShawn (40:47)
yeah. Yeah. I send them an after action report. Some people want a proof of run, is what some folks will call it. Like what day did it run? How many people got it? How many people listened? The reach. yes, absolutely. We send that report.

Becky Mollenkamp (41:02)
And then also Stephanie wants to know if you ever had an in an IRL kind of event where very few people showed and what did that do with with a sponsor? Was that how did that go? Yeah.

Anna DeShawn (41:12)
Yeah, all time.

I'd be having to go back to church where two or more gather. Okay. we made it. In fact. yeah, yeah, absolutely. And so I go back to the sponsor and I just tell them the truth. This is how many people showed up. you know, it's not as many as we hoped. Would you like to carry over and sponsor another event where we'll get more reach?

You know, and honestly, that was probably when I was doing just the radio part before the podcast started, that's what would give me the most anxiety, was like, what if we don't hit the numbers? You know, like what if I promise one thing and it don't it don't go? Right. And that would keep me in a hold where I wouldn't pitch myself the way that I should have. and that was just me not being able to see the full picture of this thing and understanding the value of my audience.

And understanding that when you build a relationship with somebody that you're selling and they've purchased something, then let's be in communication every step of the way about what's happening. And then let's if we don't hit the numbers, let's figure out what we can do to make sure you can hit your numbers, you know.

Becky Mollenkamp (42:21)
And frankly, for a lot of advertisers or sponsors, I have a feeling just that level of communication and that level of care probably goes a very long way. Right. Because I think there's many people who aren't doing that. And so they just move on to the next thing. If you're even showing up and talking afterwards and trying to say, like, how do we continue this relationship in a way that would work better for you? That's huge.

Anna DeShawn (42:43)
And I'm actively doing that right now. We had I had someone approach me, was listening to the show, and she's bought advertisements from me. one campaign was probably like fifteen K that she bought, and it garnered a little it garnered some traffic, but her prices are kind of high. So not it didn't really convert. And then she bought another package. We tried something else and for like half of that, and it worked a little, but still no conversion. And so she's back again.

We're gonna do a smaller amount, but do a much more targeted approach for who she's looking for. and now we'll see how this one goes. But we have talked it through every step of the process. what and we found what works. When I talk about it, it works. When she sends me a video of somebody else talking about it, it don't work as well, right? having

Having her put together some type of discount code that will encourage people to try her out or give her a free trial because they don't know who she is just yet has also been able to work. and so we have we're on our third time. She's about to yeah, purchase another package. And so we'll see how this one works, right? But truly it has been about building like a true relationship with her and communicating along the way.

And if something's not working, like giving her an extra this or an extra that, it don't hurt me at all to run another newsletter or to put her out in another show.

Becky Mollenkamp (44:19)
That keyword you just said, building keywords or building a relationship. And that was really a theme from the first session today. I think will probably continue to be a theme tomorrow because even if you're not trying to build, you know, because Anna, your build your approach, your goals are different than what a lot of people in this room may have as a goal. Some people may share your goal. They want to be the go-to voice for something, right? But

Or and or they want to build sponsorship dollars. There's other people in the room who are well, I just really want to get an audience so that they buy my stuff from me, right? Or just so that I continue to nurture that audience so that, you know, they continue to either be in my membership or whatever it is. Those are all different goals, but at the heart of all of those goals, the way I think that we all want to show up is that relationship component of that. If you're building relationships, it works for any of those goals. I I would imagine you agree with that.

Anna DeShawn (45:12)
a hundred percent. And when a business like if this one person I'm talking about chooses not to buy an ad for me, we still gonna be cool because she's in she's locked into the work. Like she's still somebody who's listening to the podcast, she's still somebody who's sharing the work. She's just not buying an ad. So she's she's still somebody who I have a relationship with and she might very well refer me to somebody else who she thinks might be a better fit for my audience. You know? so

It has.

Becky Mollenkamp (45:43)
Don't discount the relationships. Yeah.

Anna DeShawn (45:46)
I just can't overstate just how important the relationship.

Becky Mollenkamp (45:50)
And I see Christy asks it wasn't really a question, but I'm gonna turn it into one because you know, she's talking about wanting to grow her listener listenership to make more sales for her programs. And it's been a struggle to grow the show. And I just I know you've been at this a really long time. And this came up earlier again too, where it's just like shouting to the void, is is this gonna move the needle? How long do I give it? in my opinion, it is about.

Cons sticking with it. Consistency doesn't have to mean you have to show up every Tuesday at nine o'clock. It can. But it means that you're you you stay with it. You keep planting the seeds and you don't quit when it gets hard or when no one's there because eventually it starts to pay off. But it's you have to have that faith and belief that it will. But I'd love to hear you're speaking to it because I've seen you. Like I've had the the privilege of being able to see, at least in the beginning, a little more inside, and now from a little more of the outside, because you've been busy, which I I'm not.

Criticizing. I get it. but I've been I've been watching you, you know, I've seen the growth and the reach and the impact. So what would you just say to somebody who's feeling that same thing of like, it's a struggle to grow?

Anna DeShawn (46:56)
Yeah. So I I would say to that is pivot. So I also do consulting with folks. And so people who are not doing this full time, I just like to approach it differently because if you're looking to sell your programs, podcasting is just one piece of this puzzle, right? If the podcast isn't helping you grow, then maybe there's another way you want to show up that the podcast can then supplement. Right. So I feel like content creation is a wonderful way to sell a program.

and then you can send folks to your podcast and really hear you go deeper, right? I feel like podcasting is a deep relationship. When people are listening to you in their ears, there is a level of trust that you're building, and those people want to be locked in for 30 minutes, right? But there are other ways you can show up, and the podcast helps supplement that. So if you're a great writer, right? I think I've been consulting folks. Maybe you pivot to Substack.

And then you embed a podcast episode that's talking about the subject that you're talking about on Substack, if you're a writer, because Substack is meant it can be a place for you to grow, right? if you like being on video, then you should be on YouTube. You should be on YouTube. I also think here is a great place to talk about audience. I am very clear about who my audience is, like my persona for my people. I know who they are.

at one point they used to have names, but I don't remember the names of my personas anymore. But you really do need to know who your audience is because they probably are not at a podcast conference. Right? They could be at a financial services conference or a leadership conference, or I don't know, maybe you got a hobby and it's just like my homie Lisa, she's a she has a podcast called Stitch Please and a platform on Insta called Black Women Stitch. All she talks about is sewing.

So she goes to sewing conferences, right? and hobbyist conferences, and that's where she finds her people. Like you you really have to go to places and be clear about your audiences and then go to where the audience is. so I go to all the queer things. I'm going to the queer conferences, I go to creating change, which is the largest LGBTQ advocacy conference in the country. That's where I can connect with national people because people don't come to Chicago for real, for real.

So right.

Okay, okay, valid. but the queers, you know, they Cali or New York or, you know, Atlanta, DC, you know. So but going to these national conferences give me a chance to connect with them, right? And to build that type of relationship and then have them on my show. And then we follow each other on social, right? There's just like these steps that we all take to to build those relationships. But just being super clear on your audience and then

Super clear, there's other ways to reach them outside of your pod. Like I do my podcast once a week, but I'm doing this full time. I can rec I recommend to folks all the time to do a series, right? Do a four-part series on a specific topic that maybe is connecting to your current business offering. So then you can go on social and build an audience on an Instagram or TikTok or Substack.

And then be you know what, I got this really dope podcast episode about this. And and you know, or or something like that. I recently I moved to Substack this year. When did I move? June? I moved to Substack.

Becky Mollenkamp (50:35)
Yeah, I thought it'd been longer than that, but okay.

Anna DeShawn (50:37)
No, yeah, no, it was just in June, which is wild because it feels like it should be longer than that. I moved the cube to Substack a long time ago. I actually moved queer news just in June. So I moved our newsletter 620 people. I looked the other day and we were at 1500. So we've more than doubled on Substack. And one of the things that worked for me there was like lists and these guides I started doing.

to build audience, right? And that's driving people back to the podcast because now they get a newsletter every Monday or Tuesday about my podcast. So I changed my approach to also to building my audience in a different way.

Becky Mollenkamp (51:20)
Well,

and that's another key thing I think from listening to you for people is this experimentation. Like bring that attitude of curiosity and being like an experimenter and be willing to try things because you're trying things and some of those things work. Some of them don't. Like you said, failure is fine, but some of them do. Nadine wanted to know if it's true that the magic happens after at least a hundred episodes. I mean, I would say at least, but what do you think?

Anna DeShawn (51:43)
Yeah, that's such a long time. but I and I also think like the more specific you are, the faster the magic can happen. I think a good example are the homies who have I can see their face right now. 77 flavors. A podcast here in Chicago called 77 Flavors. It's there's 77 community areas in Chicago, and they go to every neighborhood and do history and do like a restaurant situation and

broadcast from there. They took off like right away because they were so specific. They have no struggle story at all. It cracks me up. So I think the more specific you are, the faster those hundred, you know, that takeoff moment can happen.

Becky Mollenkamp (52:28)
Yeah, and I think that's something that can be hard because we kinda sometimes I think we wanna be something for everyone. Sort of like you were saying in the beginning, like I don't wanna I don't wanna box myself into this. but that boxing in has proven itself for you anyway to be really beneficial. Alicia wanted to second what you said about Substack, great place to grow email lists. V said we partnered with a queer fan convention out in California about the beginning of twenty twenty five, grown each other's audiences hugely. That's amazing. This partnership, this relationship thing. I'm gonna take us off of

spotlight real quick. I'm still there. there. so that we can see each other if anybody wants to ask any other questions. Because I know I've been asking a lot, but we still have some time and I want to make sure if you guys have specific questions after hearing some of Anna's story and some of the things that have been working, I know you've been sharing in chat.

Anna DeShawn (53:14)
I saw this question about do ad buys stay on the podcast.

Becky Mollenkamp (53:16)
Yeah, sorry about that, I missed that.

Anna DeShawn (53:18)
yeah, in my podcast they do. But that's because I'm on lipson and I'm on a version that doesn't allow you insert audio. I have other podcasts hosted on Captivate, where you can do inserts on Captivate with like a basic version, and so they don't have to stay.

Becky Mollenkamp (53:38)
Yeah, I we ha it transistor also has dynamic ad insertion, so it's something to consider. Any other questions for Anne?

Anna DeShawn (53:49)
And I was trying to keep up with the chat, y'all, but y'all was making fans.

Becky Mollenkamp (53:51)
Good.

Buzzsprout also has dynamic. Yeah, there's a lot of wow, Lipson, you have to have a crazy number of downloads per episode to get Well, that's I mean, maybe it's because Lipson I think is or was anyway a lot less expensive, but those lower tiers then you know, that lower price point comes at that cost, I guess. Of not having those options. But moving can feel like a real pain. But I I made that switch from lipson to transistor a few years back and I'm glad I mean I get a private podcast feed now also include and then

dynamic ad and social shit. But it is more money, you know. But then also I host like five or six podcasts and it's all included in the prize. Anyway

Anna DeShawn (54:28)
Yeah.

I'm I'm I'm probably moving from Lipson just because of that.

Becky Mollenkamp (54:32)
What if you moved a transistor let me I'll send you my affiliate link.

Anna DeShawn (54:35)
Okay. I probably moved to Captivate because I already got.

Becky Mollenkamp (54:36)
Always happy for somebody to use my affiliate link.

all right, well I go. Elsie's over there. anything else? All right. Yeah, you're awesome. Thank you. It's so nice to see you again because it's been a while.

Anna DeShawn (54:49)
great to be here.

Becky Mollenkamp (54:50)
Yeah. So thank you. go ahead, Nicole. Can I ask a fun question? I love fun questions. Have you gotten to wear that really awesome orange suit you bought for the BET Awards? Is it in the closet?

No no no no. It there's gonna be a place for it, Anna, I'm confident. I think about the suit every once in a while.

Anna DeShawn (55:07)
Thank you, my friend. backstory here. I applied to do the red carpet for the BT Awards. And I got accepted to do the red carpet, went out and bought a suit, had my whole ready to go. And then I got an email saying, actually, no, actually, no, you don't have a spot at the VT Awards. And come to find out that they did that, they rescinded their offer to a lot of people after they had accepted folks. It was really, really messy boots.

situation. and so Cole is part of the Q crew. and she saw that I had a suit because I had shared the shared that with the

Becky Mollenkamp (55:45)
Well that reminds though it's so good. I remember This is such a good suit. You gotta wear it somewhere. Well it reminds me though that you do have an option of where you could wear it. Maybe because you have to wear purple. But tell everybody about this weekend because I we've I you you've said something about that. I almost forgot to mention it. You've got the purple ball or whatever it's called.

Anna DeShawn (56:01)
facts. So this is one way I've been raising money for a while, but it's called our Purple Tie Affair. It's our twelfth one. It's a concert, a silent auction. I started on my 30th birthday to raise money for my favorite nonprofits. And so for a decade I raised money for other folks. we took a year off, and then last year I started raising money for ourselves amidst all the things happening in the world. and so it's happening Saturday, October the third at Sidetrack, six to nine.

Frenchie Davis is coming to headline who is Grammy nominated. American Idol, The Voice, Broadway, Brent, all the things. So she's gonna sing us down at a band. I got a revenue strategist this year. I know those people existed. so she's pushing me to do other things, which has been great. And if y'all wanna participate in the silent auction, you totally can. It's a it's online. So if you want to, you can.

Becky Mollenkamp (56:58)
Where to go? Don't put the link in the chat but also say it for anybody who's watching replay.

Anna DeShawn (57:03)
Yeah, so the silent auction. it's g the URL's kind of long. Gallupid. Yeah, gallubid.com slash purple tie twenty twenty-six. Perfect. and then we also have a donation page, set up an account on give butter dot com slash purple tie twenty twenty-six and

There is of course another link in case somebody is in Chicago and wants to come through and you free on Saturday. And

Becky Mollenkamp (57:34)
Yeah.

Anna DeShawn (57:37)
you can use the this group can use the code FAMALY and get $10 off the ticket.

Becky Mollenkamp (57:44)
Family. Stephanie's in Chicago, but I don't know if she'll be able to go. but that's awesome. Thank you for that. I want to make sure I'm mindful of everyone's time. So thank you for being here. I saw Candace said we all get to need to get to meet Nick Robinson, and hopefully we all will. I hope everyone has time in the breakout session or the space in between our sessions tomorrow to get to know anyone you didn't get to know today. so make sure you come back, same place, same stuff tomorrow, same link, even just to keep it all as easy as we can.

So you'll come back for the first session with Rachel Lee about websites. We'll do another round of breakouts to get to know each other. And then we will have our final session with Lauren and Ariel. thank you, Anna. You are amazing. I really appreciate you showing up today.

Anna DeShawn (58:26)
Yeah, I'm glad I could be here. It's really, really great to see y'all.