Women and Work
The workplace can feel very different for women than for men. Women often feel they have to prove themselves, that they’re evaluated by how they look, or that their opinions are not respected. They feel Mom Guilt for leaving their kids while they pursue a career and worry about taking a job that fuels their passion instead of their pocketbook. We examine these real life challenges of women who are climbing the corporate ladder, growing their own business, and navigating the complex juggle of work and family. We explore how women like you can make work fit your life, not the other way around.
Women and Work
49: Critical Elements for Entrepreneur Success Beyond Passion
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
That’s something Anna DeShawn, Founder of E3 Radio and The Qube, learned as she built a media platform focused on telling stories from the LGBTQ community—especially Black and Brown voices often overlooked by mainstream media.
Along the way, she faced industry barriers, changing political climates, and the realities of entrepreneurship. Instead of forcing a path that didn’t feel right, she embraced what she calls “the power of the pivot.”
Anna shares why creating your own lane can sometimes be the most powerful response to being left out of traditional ones—and how relationships, creativity, and resilience helped her turn storytelling into a full-time career.
What’s the biggest career pivot you’ve ever made?
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#WomenAndWork #ThriveAndFlourish #EntrepreneurJourney #WomenInMedia #CareerPivot
The power's in the pivot every single time. Life does not have to be hard. I don't want to have the struggle story, okay? There will be bad things that happen, period. Like that is life. I have never had something good happen and there wasn't this current underneath of some type of trial or tribulation happening at the same exact time. This is what life looks like. I think it is how we deal with it, how we move in it, right? How we find a way to stay even, keel in it all, right? I am a person of faith. I'm really grounded in my faith. I feel like it is all gonna work out just as it should. And so here is me figuring out how to do and be and live in that.
SPEAKER_00Welcome to Women and Work, the show where we take an inside look at how women are overcoming our own unique challenges as we nurture our careers, businesses, and families. I'm Diane Mocha, founder and CEO of the Mom Sub Childcare app. And I want you to know that work can fit your life. Our guests show you the way they've done it. Today I'm with Anna Deshaun, founder of E3 Radio and the Cube. E3 Radio is an online radio station playing queer music and reporting on queer news for the past 15 years. TheCUBE is a search engine to discover, listen, and support black and brown podcasts. Anna is also the host of the AMBI award-winning podcast Queer News, where she preserves the stories of her community. Anna, thanks for being here.
SPEAKER_01I love it. I'm glad to be here. Thanks for having me, Diane.
SPEAKER_00Awesome. Well, we know media is a tough industry to survive, especially that long. So I want to know what unique challenges do you think you had to overcome specifically because of the groups you identify with, or even the identity people put on you?
SPEAKER_01It's a good question that I get fairly often, but the times we're living in right now, it's not like the times of 15 years ago. It feels today that it's even more important for us to preserve and tell the stories of those who are most underrepresented and honor their stories and amplify them in the ways in which we can. So I think if I'm presented with any unique challenges, it's the fact that the world and where we are right now in this moment, as we're having this conversation, is just so much different than it was 15 years ago. From me doing research on a story, and now everybody's removed their about us pages. They've removed their faces and their names from their websites for fear of retribution to the ongoing political attacks and legislation against the T, right? In our community and our trans siblings. So there's a lot of unique challenges that I'm facing right now that I didn't have to deal with 15 years ago when I had this bright idea to start a queer radio station.
SPEAKER_00Wow. So you feel it's harder now to be an out trans person than it was 15 years ago.
SPEAKER_01I'm gonna speak for the and I'm and I'm not gonna speak for the trans community, but okay, I do believe that because of the legislation, because of these constant and persistent and calculated and correlated, okay, and well-funded uh attacks on the trans community, it's it's absolutely more difficult. And you know, we're living in a time where they can't even get passports, right? That align with how they show up in the world. I mean, this is something, a privilege so many of us don't even have to think about. I mean, they are having to think about if they can go to the bathroom when they in a space, when they go out to eat. These are things we don't have to think about. And because of the political attacks, it's absolutely impacted how we interact with each other every day, right? The culture, right? And so, yeah, it's it's a different world we're living in right now.
SPEAKER_00So, has that impeded your ability to make a living? Because this is one way you bring income in for yourself and you know, your family. Uh, is this your main source of income? Has it affected your ability to make a living?
SPEAKER_01Chile. Five years ago, I had the bright idea, okay, to go out and do this full-time. I was one of those COVID folks that said, this is a wonderful time to reset my life. And so this is, it's what I do full-time. I run my two media companies, and this is how I sustain my life, and it's absolutely impacted me. But as it has impacted so many other media outlets, because we're living in a time where folks' funding is cut, right? Um, AI is scrubbing words like LGBT and trans and uh, you know, anything else having to do with anything cultural or anything having to support those who are underrepresented. It's it's all under attack right now. And so it absolutely impacts the bottom line of things. And at the same time, people want to be informed. Yeah. This is a time where people are not looking to hide under a rock and pretend like nothing is happening around them. And so on the same coin, right? I also have increased listenership. I have people who are more engaged because people want to be informed. So chilling, you know, pick your evil today, I guess.
SPEAKER_00And you mentioned AI. You know, I've heard women talk about, you know, the bias that exists in society and in the realm of what's out on the internet as creeping into AI because that's, like you said, what it scrubs. And I wonder if you feel like AI is a mirror and that mirror isn't necessarily what we want, or if if you think that there's ways and and people working with it are trying to avoid that. So that it's a reset where it's um more inclusive. You know, what do you think in your interactions and what you're hearing from other people in the way that AI is affecting your community?
SPEAKER_01Let's be clear. I'm a tech geek, okay? I love technology. I think technology is how we help to move things forward. And, and, and, and we need to have some regulations around what AI can and cannot do. We also need to think about the impacts AI is having on the environment, especially where they are building these data centers that are mostly being built in black and brown communities, right? In poor communities that will absolutely impact the health and well-being of black and brown folks in those areas, right? And that's being unregulated in this moment. And I think that we have to be more savvy. I had a media colleague talk once, and it just was like a light went off. She was talking about how when there were newspapers, it was very clear where the hard news section was, and then you went to the opinion section and you knew those were folks' opinions, and then you went to the cartoon section and you do it, and then you went to the sports section, right? It was very clear how we were delineating information. And now we're at a time where you don't know what is fact-checked. There's anything being fact-checked? Is this actually the truth or not? Right. And so AI just makes it all the more complicated, especially when it comes to media and people who are doing the work on the ground, who are going out and getting the interviews, who are doing their own research, and then you have these little bots scrubbing your work on the internet and then taking it and using it and not crediting you, right? There are lots of problematic scenarios we can bring up as it pertains to AI, including the fact that those who build it, right, often do not represent folks of color. And so, how does that play itself out as someone is using AI? So there's lots of problematic things as it pertains to this particular technology. And I think there's a lot of benefits. I think there's a lot of ways that uh society can benefit from AI. We've been using it predictive text for how long? Since that little clip, that little paper clip was in Word. Okay, there's been predictive text, there's been iterations of AI, just not the way in which we see it today. But I think we do need to really be critical thinkers around how we use it and how we consume it.
SPEAKER_00Mm-hmm. I want to know about your journey, you know, as somebody in this community and and as a person in the world, you know, when you were uh young and thinking about what you wanted to do with your future, you know, did you have a grand plan? Did you say, I'm gonna go to college, I'm gonna get this degree, I'm gonna get this job, then I'm gonna maybe start my own business? Did you just kind of fall into things, you know? Uh and how did the groups that you identify with impact that in any way if they did?
SPEAKER_01Yeah, I always had a plan. I'm a Virgo, okay? Through and through, all the way down to my bones. I was very clear about it all. Went straight through school, undergrad, master's work, all the degrees. Um, I stopped at the PhD part because I was like, I don't know if I'm ready to write a dissertation about one particular thing in this moment. And um it's played out the way that I thought it would. All that being said, life be life, and we pivot quickly, right? We learn from our mistakes and our failures, and then we improve. And so, yes, I'm doing exactly what I thought I would be doing. I created a path for myself in which I thought I could be successful. I decided not to go the traditional broadcast journalism route because I didn't see people that looked like me on television. I still do not see people who look like me on television. And I decided to craft my own path. That is not um what I had in mind when I was 10 or 12, but telling stories, reporting about what's happening in the world, absolutely. Robin Roberts is my North Star. And if I ever get an opportunity to meet her, she might be the one person who I don't have any words for. I might just be standing there nodding and smiling. And hopefully I got somebody next to me that loves me enough to pinch me real quick. So maybe a word comes out. But yeah, I've always wanted to tell stories. I've always wanted to report. I've always um, it's always just been in who I who I am. I remember my my parents, they actually put me in a journalism camp even before I was in high school, um, learning how to cut tape. It's just, it's just always been, I've always been very clear that this is what I wanted to do.
SPEAKER_00Mm-hmm. And it's a tough field, I know. I spent uh 15 years at a CBS station as a reporter. And during that time, I think I saw some more people from, you know, that were underrepresented become more represented. I think there was sort of, I wouldn't call it a quota, but you know, when one of this type of person left, you know, a lot of times the station would replace with one of that type of person. But maybe, you know, and then if another type of person left, it wouldn't necessarily be open and, you know, to everybody and the best candidate. You know, that was just my perspective. I don't have any data on that particular. But, you know, you mentioned that you're you love tech and you're kind of a techie person. So at any point, when were you frustrated about media and feeling like, you know, uh as this kind of a person, maybe it's gonna be an uphill battle and maybe I should do this instead. Although tech, of course, is dominated by a lot of white men too.
SPEAKER_01Let's be clear, okay? I'm a queer, I'm a black, queer woman, okay, growing up on the south side of Chicago. And when I speak about seeing people who look like me on television, it's not just about black folks and it's not just about women. It is about queer folks too. Queer folks whose identity centers around being masculine of center, right? I wear suits. Do you see y'all tell me when you've seen a woman on a woman on television wearing a masculine suit, it just does not happen, right? Because the male gaze is still important uh for ratings, right? And so, yeah, I mean, I think I've been frustrated. Uh it deterred me in college and undergrad from television. It's why I pivoted to radio. No one had to be concerned about what I looked like, how I presented, or even have a thought about that. All you had to do was listen to my voice and be all right. And it proved that that's exactly where I needed to be. And and I enjoyed it more, honestly, probably because at that age, at 18, you it's just it was just like a lot more comfortable for me. And so with the work that I'm doing now, video is now important even for radio. And so here we are, um, out here being a content creator, and as people have told me, be a possibility model for others so that they know that they could do it too and be successful at this as they define what success means for them.
SPEAKER_00And speaking of others, when people are listening to your story and they hear that you had this certain plan and you changed it and pivoted because of what you felt were, you know, barriers as well as what aligned with what you wanted to do. Do you recommend that to people? That, you know, at a certain point, do you, you know, do you really want to keep hitting your head against the wall if maybe there's a door open over there and you could go in the room and end up on the other side of the wall, right? Through a different door.
SPEAKER_01Absolutely. The power is in the pivot every single time. Life does not have to be hard. Um, I don't want to have the struggle story, okay? There will be bad things that happen, period. Like that is life. I have never had something good happen, and there wasn't this current underneath of some type of trial or tribulation happening at the same exact time. This is what life looks like. I think it is how we deal with it, how we move in it, right? How we find a way to stay even keel in it all, right? I am a person of faith. I'm really grounded in my faith. I feel like it is all gonna work out just as it should. And so here is me figuring out how to do and be and live in that. But life, life does not have to be hard or difficult. I find that when things actually come pretty easy, it feels right, things align, stuff just falls into place. It just becomes like, you know, like you playing Tetris, it just sort of all begins to fit and weave, right? And I and when I'm working, truly, and I find that let's just use Tetris as the analogy here. You turning and twisting, and things just keep blocking, and you just keep things just keep building up until you lose. Yo, I'm probably not supposed to be doing this right now. Not that I'm not supposed to ever do it, or maybe not ever revisit it, but maybe this is just not the right time. I do believe we can have everything, but we probably can't have it all at once.
SPEAKER_00Mm-hmm. Mm-hmm. Yes. And we hear that a lot from women who are mothers and have careers, and you know, they're supposed to be doing it all, but they're like, you can't really do it all and have it all at the same time. And, you know, you talk about the the power of pivot, which is is is very um insightful because when you're an entrepreneur, that's that's part of it. And so I wonder how you've been able to monetize what you're doing, because there are so many who would like to work full-time, you know, doing what you do, um, sharing stories. And it is not easy. What are some of the secrets that you can share? What are some of you know the things that you've done to build this path of being able to do this for a living?
SPEAKER_01I think you have to be very clear about your audience. I think you have to be very, very, very clear about who you are looking to reach and what stories you want to tell. Because once you're clear about the audience that you want to talk to, then you can actually build that audience. You can meet them where they're at. This is not a situation where, like, you build it and they will come. Please do not believe that. Uh, you will build it and then you need to go find the people. Okay. Um, so those are two things that I feel like I've done really well over the course of my career is I'm very clear that I am telling the stories of LGBTQ folks, and I am deeply passionate about telling those of black and brown folks within the queer community. And those are the stories that I that I central and I focus on and that I care deeply about. I think the next thing for someone to be successful is to really think creatively. Yes. Every like, every listen, every view matters. Yes, of course. And we have to be creative about how we go about selling that. And so if you really want to be a full-time entrepreneur, this cannot just be about passion. This can't just be about knowing your why. Both of those are important. It also has to be about can you sell something? Because you have a mortgage to pay, you got bills. I'm sure you have a way that you like to live. And in order for that to actually happen, you have to be able to sell yourself. You have to be able to sell your product. And so, what does that look like? For me, that looks like campaigns. Um, I I can sell you podcast ads all day, but I find it much more effective to do multi-touch campaigns. So, do you have a newsletter? Do you have a social media presence? Do you, you know, have your podcast presence? Do you have a YouTube presence? Think about the ways in which you can sell these campaigns. Are you doing events? Yes. Can you sell sponsorships? You really do have to think creatively about how you sell and how you actually bring in money so that you can survive. This entrepreneurship is not for everybody. And when folks tell me, and I want to be like you, I say, uh-huh. I know it look cute on the internet, but there's a lot of sacrifice that comes into choosing to take this path. And there's a lot of failure that you have to be okay with and understanding how you pivot from those failures. So I think those are the things that have helped me to be successful, as well as having really, really amazing mentors, really amazing people in my life who support me, who guide me, who point me in the right direction and relationships. Relationships are everything. They're the beginning and end of it all. And so if you're not good at making money and building relationships, I would not advise this way of life.
SPEAKER_00And how did you find some of those mentors? Did they just happen into your life? Did you, you know, put in effort to seek out people who were maybe ahead of you, who were where you wanted to be, or who you just felt could relate to you and no one else around you, you know, really could?
SPEAKER_01Oh, yeah. Some I searched out, some are already in my life. Um when I first embarked upon being serious about the podcasting industry five years ago, and when I began to think about building the cube and solving this problem of finding black and brown content inside of this particular space, one of the first things I did was go to Google and find who was already here. Who was already here, who looks like me, who's using language like I use. I want to meet and know these people, you know. Um, and that's exactly what I did. And I made calls, I sent emails, I showed up at conferences. I wanted to find my people. And that was the that was the first thing on the docket. And out of that came a couple of mentors. Out of that came a whole lot of friends and a whole bunch of relationships. And that is really where for me, I've been able to really be successful because you need people speaking your name in rooms, speaking your name in rooms you are not in. You cannot be everywhere, and you cannot be everything to everybody. And so having a sponsor, which is a word that so many of us are not familiar with, but you need sponsors, folks who are down and willing to speak your name in rooms you are not in, so that you can get the jobs and the opportunities you never even dreamt about. That has been the game-changing part of my whole journey.
SPEAKER_00Wow. And you know, there are some people that are either nervous about reaching up to people that are, you know, that they see as, wow, that person is so much more successful, or they maybe see them as a competitor. Well, if I'm gonna start this and they're already doing it, you know, then how are they gonna view me? How do I view them? So, how did you get past that? And what do you think about, you know, reaching out to those who may feel to some like competitors?
SPEAKER_01I don't even believe in competition. So I don't even know how to, I can't even answer that one. There, I know capitalism tells us about competition. You make a burger, I make a burger, who's got the best burger? Chile. Okay, um, I don't care. Your burger is your burger. You made that burger, that burger is unique to you, okay? If people like you, they're gonna stick with your burger. And guess what? There's enough people to enjoy everybody's burgers. Like I think I think that's my philosophy, and it always has been. Also, like I said, I'm grounded in faith. So what God has for me is for me. It is not gonna miss me. And honestly, anything that is not for me, it will miss me. It will fly right by. And then maybe in 10 years, I'll be able to Back and say, Oh, I'm glad that missed me. Even if I'm sad in the moment that it did. That is how I approach this entire journey. You cannot be stuck on the plan that you have outlined for yourself. I'm telling you right now, as a Virgo, speaking to you as someone who loves order, okay, and who always has a plan. I'm also clear that it is only a guide. It is only a guide, period. Life does whatever it wants to do. And um, that has really truly been my philosophy. I don't believe in competition. My voice is mine. And if you enjoy how I deliver and report on the news in which I am, you will come back for it. Uh and whatever opportunity sale uh award that is meant for me to have, I'm gonna have it. And just like that. And I also think there's enough for everybody. There is absolutely enough, an overabundance for absolutely everybody in every way, shape, form, and fashion. You can think about abundance. There's plenty of it. So I don't I don't approach life or business, you know, in those other ways. What a waste of energy.
SPEAKER_00That's a beautiful perspective. I I I love that. You mentioned campaigns, and I want to understand when you build these campaigns, are these campaigns that you're building around your brand and then sort of bringing in collaborators and other people who can be part of all the different pieces? Or do you actually have, you know, some sponsors that you help them build campaigns and you do some marketing for them as part of your monetization strategy?
SPEAKER_01Yeah, those sales campaigns, marketing campaigns, usually folks are coming to me wanting to leverage our platforms that are built. And so we figure out what their goals are, right? What they're trying to accomplish in this moment. Are they looking for clicks? You know, are they trying to drive um traffic to a particular page? Are they looking for more views? Are they looking for brand awareness? And then we can build a campaign and choose the right channels for those for those messages to actually live. And so we work with our clients um in a pretty white glove service type of way on these campaigns to really develop something that'll work well for them.
SPEAKER_00Nice. And so, where do you see your future? Do you think that this moment that we're in that you said is kind of precarious for you and the people in your community is gonna change, that the pendulum's swinging and it's and it's gonna swing back. And and over the course of history and time, that it will get better. Because if you look back 50 years ago, I would think we're a lot better from your, and I don't want to speak for you, but sure seems like from the outside, you know, the people in in the different communities that you serve are better now than 50 years ago in terms of the opportunities and and the perceptions.
SPEAKER_01Well, I think right now we're living in a reckoning, right? There's just this is just another time for another reckoning in America. I think that's what we're living through right now. I do think that um I'll say this. I did an interview with Nadine Smith, who is the executive director of Equality Florida. She's absolutely brilliant. And on the show, she she gave me this analogy about the slingshot. And she says that there's comes times where the slingshot, every time you just feel like everything is being pulled backwards. Everything that has been worked for, fought for, people have died over, okay, is just being removed. And when I think about that as it pertains to my communities and all the intersections in which I live, we could talk about the Civil Rights Act, we can talk about voter suppression, we can talk about redlining, we could talk about uh trans trans rights, we could talk about LGBTQ rights, everything, all the cases right now in the Supreme Court that they are going to deliver decisions on come this spring, right? Slingshot, just going back and back. And what she says is that eventually, though, eventually, the slingshot, you let it go. And when you let the slingshot go, you end up further along than when you were when you first got started. And so I really do believe that is the case. I think there's gonna become a point where that we let the slingshot go. And everything that's happening right now, we will repeal, that folks will find some type of footing on what equity and equality actually mean in this country, that people won't be stripped away from their families in this moment. Um, I think that will happen. I think one thing we don't account for is just the pain and the trauma and everything that you hold in your body and in your family and in your lineage because of moments like this in American history. And um, this moment is not the end, but I do think in my own reflection, some of this reckoning is very necessary. Because I think a lot of people got very comfortable. Um and I think that America's anti-black sentiments become very evident when black folks are not on the front line of the role, right? But when you see what's happening in Minneapolis, when you think about a Renee Good and Anthony Pready, um I think folks wake up then. Yeah. I think that's when people wake up. So we'll see how this all unfolds. Um, but I do think that we're in a moment that creatives can thrive, right? Music can thrive, people creating and building things can thrive because people want alternate versions of what um is happening right now.
SPEAKER_00Yes, people are definitely grasping for, you know, kind of how to think about it all and and and move forward. And that's a very hopeful view. And I love that you share that. And I want to get a little personal and think about your own journey and the things that you've learned, because you've you've grown so much, right, from the time you first had this plan to where you are now after all the twists and turns. And if you think about going back and changing one thing in your life, knowing then what you know now, what would that change be?
SPEAKER_01Oh gosh, I don't think I'd change anything. You change something. Y'all seen the movies, you change something, you mess everything else up.
SPEAKER_00Yeah, that's that's what we see from Hollywood. I don't know.
SPEAKER_01I don't know. Hollywood told me that once you try to change one thing, then you can go back in time and change something. Is there anything you regret? I don't live with regrets. I don't live with regrets. I just think that I'm doing exactly what I'm supposed to be doing. Now, I make mistakes. We've definitely had failures. You know, when I think about the journey of the cube, you know, when we first, when I first started this five years ago, I I the biggest, the I had the biggest vision for this thing. And I just knew people would love it. And I just knew it would take off. And and I fumbled it, you know, developers didn't work out. We ran out of money. I'd be out tabling and the the platform would be down because the person didn't do their job. And, you know, it was just we fumbled the bag in that moment. And so no regrets in all of this because today we're coming back with such a focused vision, you know, learning I've learned from all those errors. And now we're coming back in this moment and at this particular time, and we're gonna build it, and it's gonna be even better than I imagined then. So, Diane, no, I don't live with any of that stuff. And I'm just really grateful, right, for the failures. And I, and that's something that I would not have ever said five years ago. Five, five years ago, I wouldn't have even thought failure was a real thing. But I'm very clear it's real. It's very real, and it's something we should embrace and not be afraid of. And the I was in a cohort, because y'all, that's what founders do. Okay, we stay in a cohort or an accelerator. And I had someone bring to me that we had this thing we have to read, and it was saying how entrepreneurship is really a great experiment. And this reading really just opened me up to think about life, not just life, but this work as an experiment. Because in experience, in it, in when you're doing an experiment, it's expected that something's gonna fail. That you have a control, right? And you have these variables. And if something don't work, just change the variables, right? You're just constantly experimenting, constantly iterating. And the moment I heard that and light bulb went off, I just felt free. I felt so free to feel all I wanted to, so that we can actually get to where we're going.
SPEAKER_00Well, beautiful. And you know what? I'm sure your words are gonna help some other people to know that they can get where they want to go. And I thank you for all that you shared on today's episode of Women and Work. If you were inspired by today's story, remember to share with a friend, leave a review, and subscribe to meet our next amazing guest. If you or anyone you know is struggling with child care challenges, check out MomSub's free webinar that guides families through the steps to find and keep trusted, reliable childcare at momsub.com slash webinar. That's momsub like a substitute mom. You can connect with momsub on Instagram, TikTok, Facebook, or LinkedIn. Our mission is for you to discover what you want in life, pursue it with intensity, reach out for help when needed, and fulfill your dream, reducing your stress, guilt, and self-criticism, and increasing your calm, confidence, and clarity along the way. Remember, your career, your choices, and your success are yours to define. So keep pushing boundaries and spreading your love and encouragement to other women who need it.