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Making Space for Pride: An Interview with Anna Deshawn

We had the honor of interviewing Anna Deshawn. She is the amazing creator behind the online radio show E3. The show self identifies as an “authentically-edgy radio streams from a queer point of view”. 

Anna started E3 because she saw the need for a platform for people who’s voices weren’t being heard, to tell their stories and display their music. As a business who deeply identifies and supports the LGBT community, we couldn’t wait to hear Anna’s thoughts about how being a part of this community has shaped her and her radio show. 

We highly suggest you check out E3. You can find them here.

All right,  let’s get started. Anna, What is your gender and sexual identity and or expression? 

I identify as a black queer woman from the south side of Chicago.

What does being a black queer woman from the south side of Chicago mean to you? 

What does it mean to me? I’m proud of that, right? I’m proud of who I am, I’m proud that I can like stay in the skin that I’m in and be who I am. It means to me that my parents probably migrated here during the great migration. My mother did from Mississippi and miss my dad is from Chicago, my sister helped take care of it’s like another mother. It means that I’m proud of where I’m from and I’m proud of who I am. And none of my identities are more important than any of my other identities. And so that’s why it’s really important for me to really claim all of them. Because certain spaces will try to make one more important or make one less important than the other. So being a black, queer woman says a lot about who I am and my values.

Oftentimes we talk about identity, and we talk about in such left and right. I think it’s so intersectional. No one’s shared life values are going to be the same.

Absolutely. Totally agree.

So, how do you live your identity? In your day-to-day life? Does it manifest itself in the clothes you wear; or do you feel that there’s a certain way you like to do business?

I definitely have a way in which I choose to live. I choose to live in a very authentic way. I choose to live from a very social justice lens. My approach to leadership, I believe, is driven by the fact that I think that the most marginalized should be heard first. And I believe in collaboration and groupthink. I think that all derives for me and my identities.

The fact that I know that we are not always looked upon to be called leaders or to be promoted or to be heard. We are not often heard, and not heard enough. The way in which I can live my life and conduct my own business, do my radio show, do my podcast, and speak, comes from a place of allowing those who are not heard, to be heard. Because when they win, we all win.

It’s not a for me, it is not a top-down approach. For me, it’s a “let’s start where the people are”, and work our way up. People are solid, and everybody else is going to be fine. I think that things that you go through live in these identities and American culture in American society. If you are striving to be a healthy person, you’ll do things in a particular way to get the results, that actually equals some type of equity and justice in the world. So that’s how I approach it.

You talked about your radio show. What do you do for work? I know you wear a lot of hats and we want to hear all about them.

Yeah. I coined myself as a digital media artist and social entrepreneur. I would define myself in the work I do. I am the founder and CEO of E3 radio, an online radio network and curated from a career point of view. Playing career independent music and high rotation.

I have my own podcast on and it’s got a word, where I’m just talking about my perspective, everything black, queer, and beautiful. I talk about things that I care about, that I think other people in my communities care about. I am the board president of Affinity Community Services which serves black, LGBTQ people with a particular focus on black women. It has been doing so for 24 years and the community has been a pillar, legitimately a pillar, and at the table, to make sure our voices are heard, when we are normally not. I think those three things solidify who I am; they speak to who I am this speak about what I care about. And what really moves me.

So how do you think your identity influences the work you do specifically in your business? You say that there is a lot from the queer voice, so to speak. How you do that and why does it matter?

It matters because you need a platform. You know, you do those identity tests and it tells you like who you are. I did one recently and it came back that I’m a structural person. I find that an interesting one, because I’m a Virgo. So I know, I like things in a particular order.

But then also, because things that I do come from a place of “what can we do to create a platform that’s going to actually sustain something?” How can we create something that’s not just for a one-on-one, some type of solution? Or how can we affect many, and that is really how I operate.

E3 came about because I wanted to play my own commercials. And I couldn’t find any radio stations that played the commercials I wanted to play. My solution to that was creating my own radio station. I’m always thinking about how we create platforms, there are people who need to be heard. That is always my frame of mind and the frame of my topics. I think that’s how you actually affect change in society.

Media is extremely powerful. I’ve always loved media, I love what media can do if it’s used for good. And you give people an opportunity to speak who not heard, you can truly some real change because people tell their stories. And storytelling is how we survive. No one remembers what happens to them when they were two, you remember what your mama said you did when you were two, you know what I mean? It’s those stories that really drive who you become.

This is a true story. My mama said at six, I stood up, in the middle of collecting fried chicken and saying that Dr. King was a black man, and the white people killed him. I felt that passionately when asked to do my Easter speech. And that’s what I stood up and said.

The story I’ve been told about that is that I’ve always cared about justice because I’ve always cared about the other person and the right thing being done. I don’t remember doing that, but it’s the story that I’m told.

We’re able to tell the stories that matter, if you’d like to share them from an authentic place, I believe that we can affect change. Because when people know you they treat you differently. When people love you, they treat you differently, and people only make a true change when someone they know is affected. Right? People care about cancer because people in their family have been affected by cancer, people care about multiple sclerosis, because people in their families have been affected by multiple sclerosis, sickle cell, diabetes. I mean, anything you could think of, people care when their worlds are affected. Media can affect people’s worlds. Media has the power to affect people’s worlds in a very impactful way. And I want to do that. I want to change people’s perceptions of what black queer people look, feel, think, and do in the world.

What do you think is the biggest issue facing the LGBT community? And how do you think that business and social enterprises can address these issues?

Oh, Darien…

I really wish that our readers could see the look on your face.

There is no “1 biggest issue” and let me tell you why, because we live at the intersections. These issues are connected. So if I start with the most marginalized, we’re going to start with black trans women being murdered at it at a ridiculous rate, and those being unsolved murders.

And then when I think about black trans women, I’m also thinking about street economics and thinking about the criminal justice system. I’m thinking about how they’re treated, the atrocities that are created in those places when they are misgendered placed in the correct facilities, and when they don’t have hormone treatments. So I’m thinking about all of those injustices, which then continued to lead me to places of the lack of employment. That leads me to poverty, which leads me to what people have to do to survive. Right. And if we’re not starting with that place being the biggest issue, we will I mean, I if we don’t start making those particular connections in those in that particular way, this community (The LGBT) community will continue to do will eat away at itself. When I say that, I mean, we recently just had the racist incident in Progress bar, right. Beatniks. Right?

So, How can business owners address these issues?

I think they have to be held accountable? Right. I think the city of Chicago has to hold businesses accountable for what they are practicing when they have racist behaviors, homophobic behaviors. I believe there should be repercussions to your business, there should be repercussions against your record. I think they should be repercussions because of the liquor license that you have, like the success of your business, is based upon you being an equal opportunity. 

How do you affirm that? So one thing that we always talked about at D.M. Burton is being authentic as a business and the message that you’re sending across? How do we say “We’re open to everyone.”. What what does being open everybody mean? 

I think your marketing represents who you are. If you serve in black, brown, queer, and trans people your marketing shows that. You’re showing black and brown, queer and trans people, you know, this is intentional. I have to intentionally put in there I’m gonna have a black lesbian. If I am looking for black lesbians I have to intentionally write that. If I’m looking for lesbians, I write lesbians and there will be white lesbians that show up. I have to be intentional about who I’m trying to reach.

Business owners, you have to just be intentional. For example, Sidetracks’ audience is mostly white gay men. But those owners and the managers, they are open and affirming and they give back to organizations on the south side. They give back to affinity Community Services, they open their doors for other community-based organizations, that can’t afford to be in their space, technically. And they do that from a very authentic place. Everybody knows Sidetracks is an open and affirming place, not because that’s their key audience their primary audience. It’s not. But they do things to give back to the point where people know that Sidetracks is a cool place to be, that I can go there no matter who I am and be okay. I can’t say that about other places in Boystown.

Wow. Wow. I love that, I think that being intentional is something that more people need to understand. Often times when we are doing shoots I am thinking about so many different things and if we are checking all the boxes. 

But you know, you want to check your box because your boxes we’re not checked.


If I’m coming from a place of privilege, and I’m a white gay man living in a society, I’ve never had to. I have to intentionally think about checking boxes because my box is always checked. Right? So that’s why we need people of color, black and brown folks in positions where they’re making these decisions, where they’re able to shift the narrative of what this cannon and media looks like. And so that’s why I continue to pursue platforms and to create platforms that are for us. So that I can shift the narrative.

Wow well, thank you so much for taking the time to talk to me! 

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