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 Discussed in this episode:

• Anna’s relationship with feminism
• The journey of building E3 Radio from side hustle to full-time gig
• How Anna continues to honor Black women of history in her work
• Why Anna avoided calling out queerness in the beginning of E3
• How all of Anna’s intersecting identities affect how she shows up in the world and in her work
• Navigating the early days of licensing music and being ahead of the technological curve
• Breaking barriers as a Black woman in the podcasting space
• What kept Anna going in the early days of speaking into the void
• Treating every episode or project like it’s “the” episode or project that gets a “yes”
• The virality of sitting-on-the-toilet videos
• The importance of relationships in funding, and generally in growing a business — and why every high school should teach networking
• Never giving up and continually putting yourself out there as the key to growth and success
• Learning to pitch for funding
• Making financial preparations for leaving corporate and starting her business
• Why Anna’s mantra is “have the confidence of a mediocre white man”
• Adjusting revenue models based on market demands to create sustainability
• Learning to be fluid with what a business can be, and thinking before acting on new ideas
• The problem of podcast search engines and how those marketing failures are excluding so many diverse voices from the space
• Anna’s mission to change podcast discoverability for marginalized audiences

Resources mentioned:

• • Rustin on Netflix
  • TechRise and YouTube channel
  • Fifth Star Funds
  • Chicago Independent Media Alliance
  • Black HIV in the South podcast
  • Second Sunday podcast
  • “Profit First” by Michael Michalowicz
  • “The Big Leap” by Gay Hendricks
  • Urban One study on flagging of Black culture podcasts
  • Affinity Community Services

Becky Mollenkamp:

Hello, thank you for joining me. I’m excited for our chat.

 

Anna DeShawn:

I’m excited too. What up, Becky?

 

Becky Mollenkamp:

Good. Well, first, ask everyone about their relationship with feminism and always say it does not have to be one that’s a great relationship or it can be. So tell me about your experience or relationship with feminism.

 

Anna DeShawn:

I never used the word ‘feminism’ until I got to college. And I realized how much of a feminist I’ve been my entire life. I remember in high school, I was voted student board president. And one of the first things I did was request that the cheerleaders also cheer for the women’s basketball team. And we got it passed, and from that point on, the cheerleaders cheered for us as well as them. And that was probably one of the most feminist things I probably could have ever done without the language of being called a ‘feminist’ ever in my life. I’ve always been about equity, and equality, and fairness. And that’s just shown up in all of my work for as long as I can remember. So for me, being a Black feminist is probably at the core of so much of the work that I do.

 

Becky Mollenkamp:

Definitely, because everything I was reading about you talks about intersectionalism and the idea of, you know, making sure that we are looking at all identities and bringing visibility to all identities, which is really what I was most excited to talk to you about because that’s, I think the crux of what you’re trying to do is shine a light on people who don’t always get the light shined on them. And I think it’ll be interesting to take people through your journey of E3 and The Cube, starting these things, from start to now. Because from what I could tell anyway, you started the first project, E3, long before you were full-time working on it. You were doing the 9 to 5 thing, working for other companies while building these things on the side. And I think that happens so frequently. And yet those kinds of stories, I don’t think get told a lot. There’s all these stories that make it sound like you’re supposed to just go all in and start this thing overnight. And if you can’t, then there’s something wrong, which is so clearly not true. So I would love if you could start by telling us about that journey for you because I believe you started E3 radio in 2009. And from what I could tell, it didn’t look like you were full time on it until maybe ‘21. So take us through that like decade or more of building while also still having to work a 9 to 5 and pay the bills. How did that process look for you?

 

Anna DeShawn:

People thought I was doing E3 radio full-time for many years. And they were like, I was like, no, it’s a passion project. I do this on nights and weekends. And they were like, ‘What? What do you do during the day?’ It was really funny. I had the idea for E3 radio in college, actually. I attended Drake University. 

 

Becky Mollenkamp:

So did I, by the way.

 

Anna DeShawn:

I had the idea at Drake because I was learning about these Black women and their storie, and I was like, why haven’t I heard about these people before and how can I fix this? I am always, when I look back over my life, I’ve always been solutions-oriented. Not so much concerned. There is always gonna be a problem, but how do we solve the problem? And so at that time I thought I was gonna create a college radio network. That’s how this started. I was going to create PSAs about these Black women, about other people that folks should know. I was going to send them to college radio stations and get an underwriter. That was the model. Honestly, I think it’s still a great model. I just stood at…I had the capacity because there’s so much turnover in college radio. And advisors aren’t advisors. They’re just people who give their names so that there could be a college radio station. They are inundated into that day to day. And so every time I was in college and then I went on and got my master’s, anytime there was a project like if you started a business or if you had this idea, it was always E3. I took E3 from a campaign that I had in undergrad to run for student activities board president, where I said I would educate and empower and enlighten the student body through these programs we were going to put on. I didn’t win. I got into a runoff, which was great. But the E’s just always stuck with me. So honestly, when I got out of school, got my first corporate job, I was like, you know what? I can’t get anybody to play my PSAs, so how about I just start my own show and play my own commercials? And so in November of 2009, like you said, Becky, I did. I started E3 radio and my own show called the Anna DeShawn Show. And I’m almost certain I was talking to myself. Okay. Clear about that. And so for the next decade, it has been E3 radio. It was about telling our stories. It was about playing our music. It was about amplifying our work. Because there were so many queer artists who were doing great music, great work, couldn’t get amplification. The industry wants you to be a certain way, sing to a certain type of person. And there’s so many people who didn’t want to conform to that. But that left them indie, and that left them often unpaid and underbooked. And we wanted to fix that. I started taking on other shows who also fit our demographic. I was producing a lot of shows, and I just love radio. I love the relationship between a radio DJ and their audience. It is so much more authentic and intimate than anything you get on television. And I’ve just always really loved that. Now in corporate, I was also in the space. I was in the streaming media space. So I was never too far away from the work that I was doing. But as everybody listening knows, COVID was a mood, okay? And I hit a breaking point during COVID. And I was like, you know, it’s just time for me to leave corporate and try to make this thing happen full-time. And it was around that time, into 2019, we had this idea of how do we remain relevant was really the question. How do we remain relevant as a radio station as people’s listening is changing, people are going more on-demand, people aren’t tuning in at a certain time to listen to anybody. How do we remain engaged with our listeners? And I was clear we needed an app to make it easier for people to listen. And then it became a question of maybe it’s podcasting. Maybe that’s the next evolution of the work we’re doing. And so that’s the path we went down. And the Qube, the name of the actual platform is born out of E3 radio. The Qube does not exist without E3. So mathematically, E to the power of 3 is to cube something. It hit me in the shower. And I was like, yes. Now we turn this C into a Q, make a hella queer, we’ll have exactly what we need. And so that’s how the cube was born. And been on this journey now 2, 3 years of building this podcast platform, creating content and with the whole goal of amplifying Black, Brown, people of color voices in the podcasting space.

 

Becky Mollenkamp:

Take me back to the college part. You said there were, you were learning about these women that you wanted to feature, these Black women. I’m assuming you mean inside of the radio space. Who were you talking about? And have you been able to do that? Even though this isn’t that original vision exactly?

 

Anna DeShawn:

I have, I have, in my content creator work. Women like Ella Baker, right, who no one ever talks about, but it’s so incredibly important and critical to the civil rights movement. Anybody listening, if you haven’t seen Rustin on Netflix, go watch Rustin. I was so happy to have seen her depicted in Rustin, because The March on Washington and the Civil Rights Movement does not happen without Ella Baker traveling the country at a time where it was not safe to travel the country. Also really doing deep dives on women like Shirley Chisholm, and Fannie Lou Hamer, and these other just significant Black women who were doing absolutely everything but were never in the front, right? Dorothy Height. I mean, these women, they were incredible. They weren’t just in the kitchen, child, okay? They were leading, but just never with the cameras in front of them. And so in my work as a content creator, I found myself making PSAs during Women’s History Month about them, right? I found myself during Black History Month choosing to do stories about Black women during Black History Month and not just around all the Black men that we hear so much about. I find myself on Martin Luther King’s birthday, I never talk about Dr. King. I always talk about Coretta because there is no Dr. King without Coretta. It doesn’t happen without her, quite literally. She introduced Rustin to Dr. King, which means there’s no March on Washington because Rustin is the March on Washington, right? So these are the choices that I make in my work and I do it because it’s so necessary because other people aren’t. And so I will say that, yes, I have found ways to do it and incorporate their stories and amplify who they are. And that actually brings me a lot of joy.

 

Becky Mollenkamp:

Just hearing you talk about it brings me joy. I love it. And admittedly, I have some learning to do because the first person you mentioned, I don’t know. And so I’m definitely going to go watch that on Netflix. And I will link to it for people who want to see it as long as it’s still available, which will be great. And that’s really inspiring. And it makes me think about your mission. Because I know that the mission is really, again, about amplifying voices that don’t get that opportunity to be heard. And yet these are the voices of the people who are making stuff happen. They’re the ones who are at the front of leading all sorts of incredible movements that eventually us white ladies sometimes get around to saying like, let me follow along. And then suddenly let me co-opt this and make it mine. And then the visibility goes to the wrong place and it’s infuriating. And so it’s so exciting that your mission is all about how do we amplify these voices? Even more specifically, I think your focus again, because you said, let’s make that C a Q to make it hella queer, is also really specifically around Black and Brown queer women. I think Black and brown queer people, women maybe more specifically. And so before we go into the building of the business, tell me a little bit about why that matters to you personally, because I’m going to guess it’s related to your own personal story too.

 

Anna DeShawn:

Growing up as a Black woman in America, you just quickly realize all the inequities that exist just because you exist. And it has nothing to do with anything other than patriarchy and power. And so I found myself constantly just wanting to dismantle all of it, just tear it down, build it back up into something that actually makes sense and that is equitable, right? And so in my work that has always been at the heart of it. And it’s funny, Becky, at the beginning of E3 Radio, there was no rainbow in it, okay? If anybody finds the logo from the beginning of this, it was purple, it was purple. And I had an associate years ago telling me, Anna, you should just make it queer. Everything you do is queer. You should just make it queer. And I was like, I don’t want it to be queer because once it’s queer, no one’s gonna see anything else. And I also wanna focus on my Blackness. And I also you know, I also want to focus on all these other folks. And so I fought that for a really long time, a really long time. And then after a while, I started looking at all the content and I was like, it’s so queer. You can’t fight what it is and what it wants to be. And it was at that point that I decided to actually fill in the whole tower with the rainbow and just lean into what it actually is. So I will say that it wasn’t an easy decision. And even today, you know, with our work, I can say that we’re building a network for Black and Brown folks, for child, all they hear and see is me and they think queer, which is fine. We are in there too, and that’s at the heart of our Qube original content that we produce. And I’m all these things at once. And I choose not to rank one higher than the other because they all make up exactly who I am. And at various points in my life, people would want me to choose, in this space I am Black, in this space I am a woman, in this space you are queer. And in all of these spaces, nobody wants to hear about all my other identities. But if I’m gonna talk, I can’t help but bring all of them into this space because I find that in all of these spaces, they have their own biases, you know, their own hierarchies. And I’m just like, y’all, we all got the same problems. Nobody’s is worse than anybody else’s. It’s all just bad. And we don’t make progress in our own silos. It just doesn’t happen. We can only make progress together. And so that’s what I have, that’s just where I’m at today, is that I choose not to show up as parts of myself anymore. I just choose to show up as all of who I am. And that has been a journey in and of itself.

 

Becky Mollenkamp:

Friend, you say that you didn’t identify as a feminist for a long time and you just gave a whole word on intersectional feminism. I mean, that is what it is, right? It is that like, we can’t pull apart and parse out our identities. It is the whole of those identities that make us who we are and all of those things, we have to fight for all of them if we actually want anything that resembles equity and equality. So that was beautiful. Thank you for sharing that. I’m so glad I asked.

 

Anna DeShawn:

I’m glad you did too.

 

Becky Mollenkamp:

Yeah, it was great. Let’s talk about building the business. So at first you started as internet radio because this was back in 2009, which podcasting I’m sure existed but was not what it is now. It was far more in the beginning stages and more of this like, what is this podcasting thing, right? So you started as internet radio, which was new also, was this new way of thinking about radio. Traditional radio we know is now kind of dying. People don’t listen as much. They listen to satellite radio, internet radio, and podcasts. The way people listen has changed. But you start as internet radio. And one of the first things I thought about was you were young, just out of college, doing this thing. And my understanding of radio is like, there’s a lot of money involved in getting rights to music, to play it, and that sort of thing. How did you navigate that piece of it? Was it about just finding musicians who were like, I just want any kind of airtime and I’m willing to put your music out? Or did you just sort of skirt the rules? Or like, what did that look like?

 

Anna DeShawn:

Well, in the beginning, it was impossible to play music over the internet without being a traditional radio station because the platforms that existed, the origin point was a physical brick-and-mortar studio. So when I realized that, I was like, oh, that’s fine. I’ll just start a show. So the beginnings of E3 radio was talk radio. And so we would just do a lot of, I did hundreds of interviews, right, with artists and leaders in the space. Once the technology caught up with the world, then these other opportunities were able to exist where we could play music and we could do talk. And it was in those times, then we had to go out to the ASCAPs and the BMIs and pay for being able to play people’s music. And honestly, because our listenership isn’t as large as like a traditional radio station, it’s not that expensive to pay for licensing with these companies. And it keeps you from getting sued, which is far cheaper than going out here and being rogue. And so really it was me waiting on the technology to catch up with what we were doing.

 

Becky Mollenkamp:

Another example of a Black woman leading the way of something that’s new, right? I love it. And sort of setting the tone for what’s to come. That’s scary, though, for people to take that kind of chance on something new.

 

Anna DeShawn:

I don’t know if I get a thrill from it. I don’t know if I get a thrill from it, Becky, I don’t know what my problem is. But yes, it is. I guess I’ve always liked the good challenge. No one knew how to listen. No one knew how to listen. Similar to what I experienced today when people don’t know how to listen to a podcast. I mean, there’s plenty of people who still don’t know how to listen to a podcast. We just dropped a new one a couple of months ago called Second Sunday. And one of our hosts, he sent in a text, he said, I did not expect that I would have to be teaching people how to listen to a podcast. He sent a screenshot where he actually circled the play button for somebody and everything. I mean, this is what we do. Oftentimes Black and Brown folks, we consume a lot, but there’s certain things that we just don’t know how to get into, right? Because the medium hasn’t catered to us. Podcasting is one of those mediums. Podcasting has been a white man’s game for the last 15 years. And it’s only recently that people began to invest their time and energies in trying to market and reach Black and Brown audiences. I would say it starts with sports. I would say it starts with big music stars, right? But at the end of the day, there’s a lot more of us who are interested in a lot of other things. And so we are, we’re sort of embarking upon this new thing in this space. And so we still doing a lot of teaching, and we’re still overcoming a lot of tech barriers, right? And some of these other challenges that other communities just don’t have to deal with.

 

Becky Mollenkamp:

Which a big one of those is visibility, search, being able to find content. But we’ll get to that, because that is like at the crux of your mission. Before that though, you said when you started, you’re pretty sure you’re talking to yourself, no one’s listening. And I think so many people can relate to that who have founded businesses, who’ve started podcasts, who’ve done whatever, and they feel like they are yelling into a void. There’s no one there listening. And for so many people, they quit, they give up. They say, this isn’t working. They don’t give it much time or they give it some amount of time and say, nevermind, clearly people don’t want this thing or whatever. What kept you going?

 

Anna DeShawn:

It’s because people kept telling me that they loved it. People were like, and I love what you’re doing. And honestly, I don’t know if people really understand how much that means to me or to other creators out here in the space. And anytime anybody says that to me, I tell them how much that means to me because it does. Because when you’re in this space of media entertainment, where anything less than a million downloads don’t bring you no money in a significant way, it’s tough to figure out how to monetize a good idea, how to monetize a good thing, a necessary thing, where the product is you. And you don’t even like talking to yourself because you were raised not to talk about yourself. Okay. There’s no way around it in this media and entertainment space and having to settle into that. So what keeps me going is that people have found value in the word. People have invested their money and time into the work that I’m creating. And that gives me the inspiration and the energy, truly the energy to wake up and keep trying to break through that next barrier. And I feel I’m a very spiritual person. I’m very grounded in my spirituality as this Black queer kid. And I feel like there’s these divine moments that happen that I just cannot explain. And it’s almost as if God was like, what you forgot? I got you. If you just keep going, you’ll be just fine. And so I have one tattoo on my whole body, which everybody thinks is wild, but it says, trust your faith. And I remember that every time I’m in a tough spot, that I am not alone in this, that my ancestors, you know, the people who’ve come before me have got my back. And there’s, as long as I’m paying attention and tapped in, I will see that divine moment every single day, whether it’s in a conversation, when I’m looking at the clock and something, I’m like, oh, that happened at that time? That is not an accident. So there’s these reminders that also happen to me that tell me, you’re doing good, kid. You’re on the right path. Just keep pressing. You know?

 

Becky Mollenkamp:

Well, and you’re inspiring me today and I’m sure others. And I think you’re up to something like 6,000 monthly listeners, maybe more. And, but there was a time when it was far less, I’m sure. And I’m sure you have your sights on it being far more. But one thing I heard you say that I have said to people many times is imagine if I had those 6,000 people in person in front of me in a room. I would be like, oh, this is a lot of people, right? And even if it was 60 people in a room or six who were there saying, I want to hear you. I want to hear what you have to say. You would be so excited, and honored, and privileged to be able to do that. Yet somehow we let all of these metrics and numbers, the million downloads keep us from putting our gifts out into the world. And so I love that you put it that way because I think that’s so valuable. So you think about those 6,000 people that are listening.

 

Anna DeShawn:

Every day because all we ever need is one yes. I am always constantly fighting for the next yes on this journey, because all I need is one person to say this is brilliant. And I take pride in every single episode, because what if it’s that one episode that one person is listening, and that one person that wants to say yes, right? I can’t give myself the benefit of the doubt. Right now as we’re recording, I’m at episode 199. And I’m thinking about what the 200th episode will look like for Queer News. And I could totally slack off on this 200th episode. I can say, I’m not gonna do no sound design. I’m just gonna talk it to a mic and make it hella artsy or something. And, or do some type of remembrance thing, or maybe not do anything. Maybe it’s just an episode where I say thank you. But I could miss out on the opportunity for that yes. Because what if that’s that episode that someone taps into and what if they don’t listen to anything else? I’m always thinking about how I show up in the world with my art and my work and making sure that I’m giving it everything I’ve got in that moment. Cause that’s the best I can do. And I just refuse to do anything less than that. And so that’s where, yeah, that’s where I’m at with the work.

 

Becky Mollenkamp:

You need to package up a series of pep talks and sell them. Because if I had you in my ear every day, and maybe I’ll just make it myself, take this little clip and make it for myself, to remind myself, because yes! But it is so easy to coast or to sort of forget or get down or whatever. And to be able to have that reminder of this could be the thing. You don’t know which thing is gonna be the thing because how many times do we have examples of that in our lives where you’re like, whoa, this random moment happened that I wouldn’t have known, I couldn’t have made happen. You gotta be prepared.

 

Anna DeShawn:

Every, every time. And the internet will give that to you all the time. Okay, so I’m a big TikToker and the most random videos go takin’ off into the ether. I could put work into a video and I think it is going to be the video. Okay, this is a great video. You know, this is good. Nothing, okay, nothing. The most random videos go takin’ off into the ether because they resonate with people. You just don’t know. You just don’t know. So I think, you just don’t know. So I think the best thing you can do is just keep showing up as your best self every single day and then you’ll find yourself getting the yes and that rocket ship to take you off somewhere else. I mean that’s just it.

 

Becky Mollenkamp:

Yeah, my most viral TikTok video is one I recorded while sitting on the toilet. Had I known it would be the most viral video, I might not have done it. You just don’t know.

 

Anna DeShawn:

And Becky, you should have kept sitting on the toilet. You know what I mean? Just keep doing toilet videos and keep building your audience. 

 

Becky Mollenkamp:

But then if I tried, it wouldn’t have worked. 

 

Anna DeShawn:

It wouldn’t have worked. It would not have worked. Yeah.

 

Becky Mollenkamp:

Okay, let’s talk money. You are part of TechRise. Is that still true?

 

Anna DeShawn:

Ah, yes. I mean, part of it, I don’t know what that means, but I am a participant of TechRise in the P33 program. Mm-hmm.

 

Becky Mollenkamp:

Which is an incubator in Chicago where you are for Black and Latinx tech founders. And I’m curious about how you made your way into that program because I know those incubators can be incredibly powerful. In fact, I believe it’s where you did your first pitch competition and won $20,000 to help you develop the app that you’re talking about for Qube. So how did you get involved in that? And what has it meant for your business?

 

Anna DeShawn:

Relationships, I cannot say relationships more on this pod. Everything is a referral. Everything is a referral. I hate that networking is not a class. It needs to be a class in every high school, every university. No one should leave school not knowing how to build and cultivate relationships. I got connected to TechRise and P33 because I got connected to a PR person because I was looking for a PR agency to help get the word out about the Qube. I got connected to Kendra and Kendra was like, you should be connected with P33 and this program they get called TechRise. I mean, it was literally a referral to a referral to a referral that got me to even know TechRise existed. And she was like, I’m gonna get you a meeting with the person that runs it. Okay. I ended up with a meeting with Desiree. She told me all about it. She told me how to apply and I was like, oh, this sounds wonderful. And so I did, I applied. I got in to do a pitch competition. It was great. I didn’t win. The cool thing about TechRise is that they can invite you back, and they did. So they invited me back and then the second time I won. And then I got invited to, because I won I could then enter myself into the grand finale. I didn’t get it the first time. Then I was still in the cycle to be able to go back the next year. I did, I got in, and then I got to pitch on the big stage last year. But let me tell you, it is about continually putting yourself out here. And I think that that’s the part that gets really hard for people, is that once you put yourself out there, and you are so incredibly vulnerable every single time, it’s hard when you keep getting the nos. Where somebody says, not you today. But let me tell you, when you keep doing it and you get all the nos, that’s what makes the yeses so freaking sweet. So every time at TechRise, it was a no, and then it was a yes. And I think that is the story of our life, is that you will get absolutely more nos than you will get yeses, but the yeses will reverberate so long. TechRise last year, people still come up to me, I mean, even just a couple weeks ago. It was like, I recognize you. I was like, you do? I don’t think we’ve met. And they were like, did you do TechRise? I was like, I did do TechRise. It was like, I loved your pitch. I did not win that pitch competition. Do I think I had the best pitch? I do. But did I win? No. And I realized that it is not about the pitch, it is about what resonates with the judges. It has absolutely nothing to do with you. And so my pitch just didn’t resonate with the judges, but it resonated with so many people in that audience that they still come up to me and talk to me about it. And it was the most devastating loss I’ve ever had. But it has also been one of the biggest wins that I’ve ever had. So TechRise is beautiful. They do these weekly pitch competitions. You can win up to $20,000. Some of them are $25,000. They’re really thoughtful about them. There’s some of them that are specifically neighborhood-based, and specifically underrepresented communities. Like one week it could be, you know, Inglewood founders. Another week it’s women founders, women and non-binary founders. Another week it is Black founders, Latinx founders. And it’s just really beautiful. And if you are ever thinking about doing a pitch competition, their whole YouTube is just full of amazing pitches. And everyone does it a little different and everybody’s approach is a little different, but you can get just so much information around how to do a pitch, and then also what questions judges are going to ask you at the end of a potential pitch. Because you can practice the pitch all day, but if you ain’t practicing how to answer the questions, then you’re not practicing, you’re not doing the full practice that’s needed. So yeah TechRise was a beautiful experience I’m actually about to make a video about it, and encourage people to actually donate to the situation there because we need places like that, that are providing significant capital, significant capital to small businesses for not having to do a whole lot of work, you know?

 

Becky Mollenkamp:

Yeah, did you learn about the pitching process through your experience with TechRise or on your own? Because that would have, I’m assuming, was a pretty new experience for you and it’s not easy.

 

Anna DeShawn:

It’s not easy because you got to do it in like four minutes. I think TechRise is four minutes to try to tell the whole story in four minutes, y’all. It’s a mood. I learned how to pitch probably from YouTube. And then also at Fifth Star Funds here in Chicago is our first investor. They wrote us our first check. And so they were also very helpful and instrumental because it’s a VC, but it’s founded by all founders. And so all these founders are also fundraising. They also are pitching people all the time. And so they helped me a ton because they stay pitching. And so between them, and YouTube, and advisors, I was able to pull together what I thought was a good pitch. And it keeps getting refined all the time. I also had a pitch coach for this last time. I actually got a pitch coach and that was amazing. And this pitch coach was a white woman and that was even great because she didn’t understand anything I was talking about. She didn’t even know what BIPOC meant, okay? And I said, this is good because there’s gonna be other people who don’t know what BIPOC means. So what are you hearing and how can I better tell this story to relate to as many people as I can? So it was actually, I’ve gone through many stages of the pitch process, and learning how I do a pitch well, but this last time when I had a pitch coach, it really helped a lot.

 

Becky Mollenkamp:

I think you did an Indiegogo fundraising campaign at some point also. So what is all the money, like what does that process look like for you, as far as fundraising? And I wanted to ask about, cause I believe you’re now moving into a new phase of pitching and looking for funding, but up until this most recent, like where you’re at now, what has the funding looked like for you? What’s that process been? How much of it was on your own, self-funded, or through something like an Indiegogo versus like investments?

 

Anna DeShawn:

Yeah, leading up to leaving corporate, because I had thought about leaving corporate for a really long time, I was saving my money, right? I was listening to all the advice from all the people who have done it before, have three to five months of savings for monthly expenses in the bank. So living very lean, leading up to the time I was gonna quit. I didn’t know when I was gonna quit, but I just wanted to be prepared for when it felt like it was time. At one point in my journey, I would say, I’m leaving this day, this time, I’m gonna be out. That never happens. And I got some great advice from another founder, they were like, that ain’t gonna work. They’re like, they told me, you’re just gonna know when it’s time and you’re gonna have everything ready and it’s gonna be right. And that’s exactly how that all happened. And so I had savings, I pulled my 401k because there’s a certain amount of time you need just to figure it out and make a whole lot of mistakes. And you need time to do that without having to be so bogged down by not being able to pay your bills, because there’s no way you can focus on dreaming if you are focusing on survival. Those two things are very hard to live at the same exact time. And so I did that. I had that already saved. And then I did the Indiegogo in 2020, which is wild to say to fundraise during COVID. People thought I was nuts. Because I told them I wanted to raise $70,000 because based upon the budget and the talks I was having and scoping out the project, that’s how much I was gonna need. But I’m doing this in the middle of COVID. And so we did. And what happened was, at the same time I was doing my Indiegogo, I’m part of the Chicago Independent Media Alliance, CIMA, C-I-M-A, and it’s a collection of local independent media organizations here in Chicago. There’s about 60-something of us represented, and we do an annual fundraiser, and it happened to happen at the same exact time. And this year, CIMA had matching donors. And so what happened was I had lined up people to give $500, $250, somebody was giving a thousand dollars directly to us. But if they gave to CIMA, then that was going to be doubled and then tripled. And so I was like, don’t y’all get it as Indiegogo? I need y’all to go over the CIMA and give over there so that your donation is doubled and tripled. And so what happened was I did that for a select number of people, and then I had everybody else give to the Indiegogo because I didn’t want to confuse everybody, but I knew I could make direct asks to certain people. And that’s what happened. That’s how we were able to raise $70,000 in 2020. And what I learned is, you know money go fast in this tech business and it wasn’t enough. But I will say that decades long of building E3 Radio is how I was able to build an audience and it’s also how I was able to build trust in my community, and it’s also how I was able to raise that amount of money. It is not something that happens overnight. There is no such thing as overnight success. And so that was the beginning. From there, we were able to get our first check from Fifth Star Funds, which is a VC here in Chicago, who’s supporting Black and Brown founders in tech. So they wrote us our first check for $25,000. And then from there, it has been about how can we monetize the work that we’re doing? Everything is an experiment. I learned that in one of the accelerators I was in, SCCC accelerator, Tiffany Michael, everything is an experiment. And that’s how I approach and look at my work today. Every time I’m doing something new, well it’s an experiment, it could go wrong, it could go bad. We expect experiments to fail, right? We as people don’t expect to fail, but failure is part of the process and it’s about just failing forward. And so I do, I look at everything as an experiment. Let’s see how it goes, time. It keeps me balanced.

 

Becky Mollenkamp:

I don’t know if you are just perfectly built for this entrepreneurial life, or if you developed into the perfect fit for this entrepreneurial life, but I love so much of what you’re sharing because I think it’s so important for people who are behind you on this journey to hear that, one, I hear so much belief in self. If you don’t believe in yourself, no one else is going to. If you don’t believe in what you’re building, no one else is going to. So much about not quitting. You know, you finished second or you didn’t win the thing, and then you did it again and you got it or you didn’t do it again, and you kept trying, right? The never giving up stuff is so important too. And then that piece around, I wanna frame what you said about you can’t dream when you’re just trying to survive. This idea of it taking time and there aren’t overnight successes because I think too much of what is out there in a lot of the, let’s be honest, mostly white men and white women who are out trying to make money on helping people grow businesses, it’s so much smoke and mirrors that’s making people believe that if they can’t do it immediately, if they aren’t instantly successful, that they aren’t doing it right. And so then that makes them wanna quit. So I’m curious, do you feel like you were just, like it’s just the way you sort of have always moved through the world, or have you had to hone these sort of skills and beliefs?

 

Anna DeShawn:

It’s both. I feel like I’ve inherently always been this way. At the same time, I was raised to do all the things. You go to school, you get good grades, you get a good job, right? I was also raised in a very religious, rule-oriented household, okay? And it has proven me, it has proven to work for me, okay? But at the same time, it does not align with the typical creative, like this is the opportunity for you to think outside the box. That doesn’t, there was, no, we were in boxes, okay? And you did exactly what you were supposed to do and be successful. But at the same time, I would always do something like drive people to want to vote in favor of having cheerleaders cheer at girls basketball games, okay? So I was always also this person who was always fighting also against what someone said was normal or right. And so I feel like that has always inherently been in me. And I’ve also always wanted to learn so much of things I did in the beginning, where it was me researching. You know, you say start a business and you think it’s hard, it’s a piece of paper. It’s like, it’s like two pieces of paper, go get an EIN number and go do some LLC paperwork. Ta-da, you’ve got a business. It is not rocket science, you know what I mean? And so then it’s sort of all these other myths begin to dispel once you realize, oh, that’s not the hard part. There’s no barrier here. That’s the easy, we can do this, we can do this over and over again. Oh, and then I also began just learning from other white people, truly white men who are out here. I was like, oh, you just failing and people just still give you millions of money, huh? Millions of dollars, got it. I think I can do this. And so, you know, part of my mantra right now is just to treat life like a mediocre white man would. I find that there is gonna be a lot of success for me in that. They ask for more. They demand what they feel like they need. They apply for things they are not qualified for all the time. Like the research shows us that women don’t apply unless they feel like they can meet every single point on that job description. And the data shows us white men, they will apply if they just meet one. They don’t, they not trying to apply and fit all, right? But this is how we were taught. And so I am to answer your question, I think it is both. It is something that was inherently in me. And then it’s also something that I have learned. I have gone out and looked for people who have been successful, who have done what or been where I want to go and seeing how they function. And I just soak it all in. And I keep the things that are for me and I leave the other things behind.

 

Becky Mollenkamp:

There is a lot of gatekeeping and issues that create barriers that make it difficult sometimes to, and you can have the confidence of the mediocre white man, but you can’t always have all of the resources or access to the rooms. And you’ve talked about some of that and how you have found your way into those spaces. I want to talk a little bit more about the access in a second. But before I just want to tie a knot around the finance piece, which is where are you at with the app? And I know you’re now moving into this next phase of like heading out to Silicon Valley to really do that next sort of degree of pitching. Where are things at for you now and what’s next?

 

Anna DeShawn:

Well, now I’m figuring out how we actually monetize this and in a sustainable way. So we’ve landed good deals, right? So part of last year, what I thought was gonna be our revenue models where we’re gonna license our podcasts out to some major networks that need Black and Brown queer content, right? We do that, we do it well. So let’s license and distribute that content out there, and then next would be advertising, a then events and grants. The licensing worked. We were able to license two of our pods to major networks. Black HIV in the South is with Urban One. And then we have Second Sunday that is with PRX for two years. Wonderful. The licensing is great. The ad revenue never came because selling Black and Brown queer content is not something that those sales departments know how to do really well. Ta-da, big surprise, right? Well, what you think is gonna be residual income quarter over quarter, it just has not come. It also takes time to grow an audience in the podcasting space to equate to significant revenue that’s gonna keep coming in. So that was a reality that you learned. That’s part of the experiment, right? And then you begin to adjust accordingly. So that’s been successful and, right? Advertising has been great. I have to go the local route. I treat it like I treat radio advertising, going to small businesses, people in my communities that want to reach the audience that I want to reach. I am not at a place where a traditional podcasting CPM model works for me. And for people that don’t know, it’s cost per mile. Every mile is a thousand listeners. So people only get paid, the average cost is 15 to $30 for a CPM. Imagine how many listeners you got to get if you have $15 CPM, every thousand listens to actually make any significant income. So to be at scale, that’s the only way that CPM works. So I have to look at our listenership. I have to look at our social media reach. I have to look at our newsletters. I have to look at podcast membership. We got to get creative out here in these streets to be sustainable. And even then, sometimes it’s not enough. So financially, we’ve been doing good. We break even because I just keep reinvesting everything into the business. And I actually just got a good recommendation on Profit First, a book that someone recommended that I read, it’s a good one, Becky, okay, on how I can continue to improve that side of my business acumen to be a sustainable business out here in the streets. But I think that we’re onto something really special. My goal is just not to quit before we hit the moment. It is so easy. People offer me jobs all the time, and I can’t tell you how lovely a steady paycheck would be. I would love to put my bills back on autopay. I was living a good life in my Zone of Excellence. Then I went and read “The Big Leap,” which is a book I’d recommend anybody reading.. And when Gay Hedricks talks about the Zone of Genius and I’m like, I want to work in my Zone of Genius every single day and strive for that. And, and so I’m standing the fight. Let me tell you, my affirmation book keeps me grounded. Every morning. I journal, I do things to keep my mental health sane so that I could be out here in the world, pitching myself, putting myself out here, tapping into my networks so that we can be sustainable. This next phase is just an extension of that. This VC funding is just an extension of that. I feel like we have to get this type of funding to get the access that we need to make the connections that we need to be the number one podcasting app for people of color. That’s the only way that this works.

 

Becky Mollenkamp:

And I’m happy that you told me that you are doing things to protect your mental health, to keep yourself grounded and sane, because this is hard. And what you’re doing is very difficult. It’s all consuming. Like you said, you’re pouring money back into the business and not into your own bank account. Like it’s very challenging. It’s challenging to sustain yourself, to try and maintain relationships outside of just work. And so it’s so important that we care for ourselves. So I’m really glad to hear that you are. And I can also understand why you’re getting lots of job offers because spending any amount of time listening to you, I would wanna hire you too. 

 

Anna DeShawn:

I’m a great employee.

 

Becky Mollenkamp:

You probably could be a great employee, but I feel like you are meant to be an entrepreneur. But that’s gotta be challenging when people are saying, I’ll give you a job and it’ll pay you well and you can be sustained. I mean, at so many points in your story, I hear places where it would be easy for you to quit, it would be easy to give up. And I’m just really impressed that you keep at it. I mean, good for you.

 

Anna DeShawn:

Oh, Becky, I am amazed that I keep at it. I looked up and I was like, we’re three years into this. You know that we have defied the odds already on a full-time basis. You know, I tell people we talked about E3 Radio starting in November of 2009, and it was a passion project. It is far different to do it full time. It’s far different, leaving a six-figure job to come do something that is not guaranteed to make you absolutely anything. And when you’ve got responsibilities like a partner, an expensive wife, okay, a dog, a mortgage, a mother who’s aging and needs support, father who’s aging, all these things are factors where you’re like, gosh, some stability right now would be really great. At the same time, the possibilities of this thing really just fuel me in so many ways when the things are getting tough. There is an amazing opportunity, I truly believe that, in reaching this audience in the podcasting space. And I wanna be the person that ushers it in because I feel like I can do it well. And all I need is a few people to tell me, yes, they believe in me and they believe in this. And I think we can do something really, really special. Do I know what that looks like in its totality right now? I don’t. And I think that that’s one thing that I’ve also learned in this journey is to be open to all the possibilities of what something could be. And I get this question a lot, like, what do you do with all the ideas you have? Because creatives, we got thousands of ideas, thousands of things we wanna do. And I tell people all the time, I just sit on it now. I used to move on them real fast and I’ll do something, because it’s like a new relationship, you get really excited in the beginning, everything’s lovely, and then you get tired of it. Now I just sit on ideas and I just keep them in a list and then I’ll share a couple and then people give me more ideas. Oh, what about this? What? It could be this. I, and I think it could be this. And people tell me what they think the Qube could be all the time. They’re like, Oh, it’s like the Netflix of podcasts. That’s cool. Never thought of it that way. Not how I ever saw it. It could be that. It could be something that’s a part of all these other platforms so that they can be more inclusive. Does that still meet the mission? Like what is the mission? So I think we come up with these ideas, and then we think that that’s the only way it could be. But there’s so many ways for this dream or this vision to manifest itself in the world and the Qube could just be the conduit to all of it. So I’ve also just been remaining open to how this actually shows up in the world.

 

Becky Mollenkamp:

Again, such an important part of successful entrepreneurship. I hope people are paying attention. What I’m hearing though, is the thing that doesn’t change and the thing that keeps you in it, is the why. That’s what you’re grounded in and that’s what keeps you going and all those times you could jump off, it’s the why. And so that’s what I wanna talk about last because I think it’s, even though it’s the most important piece, I think getting it to last because, and this is perfect, it’s, what has kept you in it? It’s the why, and what is the why? And I’m taking this from your Ambi Awards speech. By the way, congratulations, you won the Ambi Award for, I think it was Best DIY Podcast, which it was funny in your speech, you said something like the threshold was under $3000 an episode that people were spending and you’re like, well, I’d love to have a $3000-an-episode budget. And I’m like, well, wouldn’t that be nice? Me too, my budget is $50 if that.

 

Anna DeShawn:

I’ll tell you too. They actually changed that this year, which I’ll take, I’ll, I’ll take credit for that $1,000 or less.

 

Becky Mollenkamp:

OK, so you said there’s a lot of people making content that people cannot find, that you want to tell the stories of queer folks, and Black and Brown queer folks, and that you’re here to tell those stories because they deserve to be heard and amplified. And I think that that, to me, sounds like what is the heart of it. And then I also saw somewhere that you had said, what you’re basically creating with the Qube, or the intention, is to create an ecosystem to create the change we wanna see in the world. And that changes, we want these voices to be heard. Why aren’t they? What is wrong, currently, not like the obvious sort of glaring thing in the room aside, which is the racism, the sexism, the homophobia, all the things that exist within our society as a whole, but more specifically, around the podcast search engines, the way people actually go about finding podcasts to listen to, how has that created or exacerbated these problems that exist?

 

Anna DeShawn:

Yeah, because they aren’t marketing to Black and Brown people. They’re barely marketing to women, right? And when large companies don’t do that from the beginning, marginalized groups get further marginalized, right? So there’s an assumption, if there’s an assumption in the boardroom that group of people aren’t listening, that they aren’t invested in the marketing needed to reach those groups of people. And so, when this goes on for the last decade, then those audiences then aren’t tapped in. They don’t know that this medium is also for them. And people can create great work, but if they don’t have an audience to reach, then what’s happening because media and entertainment is totally fueled by advertising dollars. There was a study done recently by Urban One’s podcast network about search engines and how language that Black people use was being flagged as inflammatory or wrong. And so their podcasts weren’t being boosted to get the visibility, because they thought that it was sort of like defamatory or something like that, right? But it’s just how we talk. It’s just a word, just words that we use in just our regular vernacular that are getting flagged. And so these types of things that are happening are preventing content by Black and Brown creators to be found. But this is also like, this is when we talk about the systemic things in all these spaces that prevent growth. Because there was no, I don’t know for a fact, but I’m just gonna assume there were no Black and Brown people in the room when they were developing those rules on what language was acceptable and what language was not. I’m assuming there weren’t Black and Brown people in the room when they were building these platforms around who’s listening, how they were serving a podcast who they think you should be listening to. And so when we are not in those rooms, when we’re not represented, then it will represent whoever was in that room. This is what we know for sure. And this is why representation is so incredibly important. We are here. We do want to listen. We just need to know there’s stuff out here for us to listen to, that there are black that there are women talking about things women want to listen to. That there are Latinx people out here creating content for Latinx folks in all the different languages and all the different dialects that I can now listen to. But if people, if the marketing dollars aren’t behind it to push that narrative, then no one will know.

 

Becky Mollenkamp:

They may have been in the room, but they probably weren’t the decision makers, right? Because even if you’re in the room, if you don’t have the power in the room, then what does it do? It makes me think of a recent experience I had on Threads, where I posted white men are the problem. Just a sentiment. I don’t know. I also think it’s a truthful sentiment, but okay. And it was taken down twice. I reposted it, again taken down as hate speech. And yet I recently had a response to something I posited calling me a cunt, that wasn’t removed. That’s not hate speech, right? Like that’s okay. And there’s many other examples of that people have, but these are the sorts of things that are happening, right? And when you look at, I use Apple because I’m an Apple person, and so when I go into my Apple podcast to look for what’s out there, it is incredibly difficult, I have found, to find new content beyond the certain things that Apple has decided to highlight. And you know, that’s, yeah, Joe Rogan, maybe people like him. But I also wonder how much of that kind of success is due to the fact that his kind of content as a white man is what’s really featured, right? Is it because people love him that much or is it because it’s so fucking hard to find anything else to listen to? You know, if somebody hasn’t told you, it’s hard to find anything.

 

Anna DeShawn:

That’s it. Discoverability sucks. The data shows us when it comes to podcasting, it’s Google search and then it’s word of mouth. Those are the top two ways. Apps, last report I saw were at the bottom of the list. So if you aren’t Googleable, if you don’t have the time or the budget to create transcripts for every podcast, for all your show notes, if you aren’t doing searchable things on Google, you won’t be found. If your audience isn’t huge, then who’s word of mouth, who’s spreading the word about you? Right? And what I think is the biggest opportunity with podcasting is to fix it before it gets too large of a problem to fix. Right? The work to fix the film industry has been decades on decades on decades on decades of work to try to fix all of the wrong that happened in the film industry and continues to happen. Television, same thing. Radio is different because they knew that Black people wanted to listen to Black people on the radio. And so they put Black people on the radio to talk to what they would call urban audiences. That was really easy to do. Then they started to create conservative stations because conservatives wanna listen to more conservative radio and liberals wanna listen to liberal radio. And so radio is a little bit different. And I think podcasting is an extension of radio and in that it is different. And there has yet to be an investment in those marginalized audiences. And I want to change that.

 

Becky Mollenkamp:

Clearly it matters to you enough to stick with it. And so that why is so important. And I think it’s important for people to hear that when you’re building a business, if you’re starting something by yourself, you’re starting from the ground up, if it’s a passion project, it’s not going to be easy. It just isn’t. There isn’t that overnight success. It’s not easy to build a business, certainly not one that’s profitable, that grows. And to stay in it, it better be something you really care about, that you better be really passionate about.

 

Anna DeShawn:

And I tell people all the time, when you’re introducing yourself, you should lead with your why, not your what. And we’ve always been taught to lead with the what. What are you doing? I’m interested in amplifying underrepresented voices in media and right now that’s showing up in podcasting. That’s what I’m interested in. What it is or how it manifests itself, that’s something else. But can we connect on the why? I think everybody should practice introing themselves with the why and not the what.

 

Becky Mollenkamp:

There was more I wanted to ask you about. Quickly say, you had done a tour last Fall around the US doing these immersive listening experiences. So basically people would listen to brief excerpts of podcasts with headphones on in community, take the headphones off and discuss. And it sounds like that went really well. You loved that. It’s a very different approach to, because podcasting is this thing that we think of as a solitary experience. And yet, how often do you wanna be like, oh my God, that thing I just listened to, I need to tell someone about it. And if you don’t have someone to tell about it, it’s like, ah, so we go to social media or wherever. So I think it’s brilliant, I love it. And now from what I understand, you’re getting ready to do the same thing in 2024, hopefully to colleges and universities. So can you just like very briefly tell me about those experiences and why you wanna do that?

 

Anna DeShawn:

Yeah, I had this idea a few years ago. Like literally I saw a homie who throws parties and she had a silent headphone party. I was like, oh, that’d be great to listen to podcasts that way. Because podcasts should be heard surround sound, noise-canceled. You can hear all the sound design. Like there’s so much that goes into making a beautiful podcast, and you lose it and the speaker, okay. You just lose it. And I had that idea. And I said, Oh, I’m going to use that. I got her connect, it wasn’t until last year that I actually connected with that person. And I was like, I would love to be a partner and use your silent headphones to do this silent headphone listening with podcasts. He’s like, I ain’t never heard nobody doing that before. I was like, I know, but I think it could work. And I was like, I want to try it out, run this experiment, and I’d love to partner with you on it. He’s like, let’s do it. And so it has just been amazing. We went, we did six different activations—Brooklyn, Manhattan, Denver, we did two in Denver, did one here in Chicago, went to Maryland a couple times—and it was just amazing. Everybody sitting in silence but laughing at the same times, right? Or about ready to cry at the same time, depending on the audio. And we played the trailers from all of our pods and then we will talk about them. How did people feel? How did it resonate with you? What did you think? And I just loved every moment of it. And we were in a season where people are tight on money, things are really feeling impossible sometimes when it comes to inflation, interest rates, all these things that are happening. And so I was like, I don’t need nobody to come to me. Let me just go to the people. Because what I know for sure is that word of mouth is still the strongest thing we got. People wanna get to know you as a person, no matter how much you wanna try to take you out of your business, you are your business. And business is personal. I don’t know who said business wasn’t personal. Sound like a white man thing. Business is very personal. And it is my livelihood. And so people need to get to know me in order for them to get to know this podcast. And so I just felt like it was the best way to do it. And it was brilliant. I freaking loved every moment of it, connecting with new people in new cities, expanding our audiences. The first time I left Chicago to do this work. And I’ve just found so many benefits from it. And I wanna keep it going at colleges and universities with young people who are inundated with so many messages and they listen to podcasts, but I bet they are not talking about them in the community. And so how can we create these fun spaces to do that? And so podcast on campus, let’s go.

 

Becky Mollenkamp:

Last thing, Robin Roberts. What is it? I see everywhere you talk, look, immediately you’re like, ooh. You’ve been in love with Robin Roberts your whole life, you say, and that if you were ever to meet her, you would probably be speechless, which I see. So tell me what is it? I mean, I think Robin’s amazing, but tell me what it is for you that really just does it.

 

Anna DeShawn:

I grew up a gym rat. My dad’s a Hall of Fame coach. I was in the gym all day. We spent our evenings watching ESPN and she was the only Black woman on there. She was the only Black woman on ESPN. She would be on ABC Sports. She was interviewing everybody. She was everywhere. And the more I learned about her, I just felt more connected. My mom is from Mississippi. Her people are from Mississippi and she made it to New York City. You know what I mean? And then just for her to recently come out, I mean, we all felt it, you know what I’m saying? But for her to finally come out about her relationship and who she is, it just felt like there was such a great connection there and she is just such an inspiration. And I always, always felt that she never got her just due, that she never got the roses and the flowers that she so deserves for her decades long groundbreaking work in journalism. And that’s the goal. She is the model for that, in my opinion. And I just, I would love to be able to sit down and talk to her about all the things—love, identity, work. And I’ve gotten so close to meeting her on a couple of occasions, but I know when it happens, it’s gonna be so perfect that I’m gonna breathe, and try not to faint, and maybe ask a question. But I just think she’s just really, really brilliant. And she’s been so vulnerable with her struggles and with her life in the public. And that is very hard to do when you’re on the number one morning program in the country, you know, and I think she’s just a testament. I think she’s opened a lot of doors for a lot of people and, and I just freaking love her. So thank you for asking.

 

Becky Mollenkamp:

Okay, the last, very last thing, I said that was the last thing, but the actual last thing is I would love to hear about a nonprofit that you support that we can shine a light on.

 

Anna DeShawn:

Absolutely easy work. Affinity Community Services, they are a Black, LGBTQ-led org on the South Side of Chicago serving Black LGBTQ folks and women in particular for the last 27 years.

 

Becky Mollenkamp:

I will be making a donation as a way to say thank you for your time today and encourage everyone else to do the same. There is no way that you listen to this episode and don’t feel some kind of way. Probably very inspired, hopefully very motivated to stay with it. So thank you so much. And we’re going to record right after this, three tips for DIYing or getting started in podcasting because I know so many people, we know how many people have podcasts, but also how many people want one and haven’t done it yet, and maybe it’s fear of just what does it take to get started? And so we’re gonna talk about three tips for doing that. So if you wanna hear those, make sure you subscribe to the newsletter, which is in the show notes. And thank you so much. I can’t tell you how much I love this episode.

 

Anna DeShawn:

Thank you, Becky, this has been dope.