Claiming Our Power in Media at Dream Con’s Fireside Chat with Issa Rae and Roxxy Haze

Black Nerd Problems descended upon Dream Con this summer, covering the widely known Black and Brown-centric convention for the first time. Packed with activated booths, indie creators and artists, niche or out-of-this-world swag and loot, the feeling was right at home. For the most part. Heavily streamed by every content creator you can imagine, it was a playground for the Blerd and every minute recorded and live. Clearly, built this way by its founders Mark, Affiong “Aff”, Leland, Desmond “Des”, Ben, Dylan “Dyl” and newest member John of the viral sensation RDC (Real Dreams Change the world).

HIGHKEY VIBES 

The vibes were vibing – take that how you will. Every moment there was a chance to meet creators you know and love, be the creator you know you can be, and answer the question: ‘do I want to be a content creator?’ All with the common ground of nerdom. Well, almost all. Some clout chasers were found roaming the floors working real hard to create those toxic environments these sort of conventions exist to eliminate. You can’t catch’em all! But all in all, if you came with a good crew, you had a good ass time. 

What stood out more than anything was the dedication to provide a space to own your nerdom authentically. Whether you love making strange voices for cartoons, cosplaying however you interpret a character, making Viltrumite push-up videos, ranking the best rappers, or spitting poetry for the nerd community, there was a place to do whatever TF it is you do. Blerd ladies in tech, financial advisement, gaming the YouTube algorithm, voicing animated alien creatures in front of a live audience. Everything had a home at Dream Con. 

HIGHKEY IT’S ISSA RAE!

Even the OG awkward Black girl herself, Issa Rae, pulled up to talk about how she continues to expand the world of awkward Blackness in modern media. Issa Rae has been a force in the industry since The Misadventures of an Awkward Black Girl first captured our attention and Insecure turned our heads. She’s expanded the way we believe Black media can be and how we write Black characters, allowing them to be full humans. Not perfect, not likeable, not a stereotype of hood or gangster, but more authentic and, of course, hilarious and cringy. 

Issa sat down with host and personality Roxxy Haze at the Dream Con fireside chat. Roxxy brought her unique style and had us laughing and learning the whole time. Roxxy and Issa’s chemistry was comfortable and familiar, which had the thousands of attendees feeling part of the kiki. Roxxy had Issa elaborate on her journey to bring together her media networks through Hoorae Media, Raedio, Ensemble, and Color Creative. 

Issa Rae’s media consortium is built as a hub for filmmakers, writers, and creators of all kinds. Making a space for creators of color to thrive. Raedio hosts everything from podcasts to music and film and TV music supervision. Color Creative is a production and training company for mentorship, exposure, and management of your filmmaking career. Ensemble, the newest of Issa Rae’s ventures, opens up access and new routes into the creator economy. Boasting “Our mission is to make the creator economy more equitable for creators from historically underrepresented communities.” 

It’s only fitting that Issa Rae’s pursuits seek to bolster the careers of content creators in the online space. Speaking on her indie web series beginning, she reminisces on the fear that almost kept her from releasing her breakout project Awkward Black Girl. 

Issa Rae: Where is the Black Liz Lemon? Talking about how there’s a character on 30 Rock played by Tina Fey, and they were looking for… They were like, “There are all these quirky, white women. Where are the perky Black women?” And she said quirky Black women, and my show is called Awkward Black Girl.

I was like, ‘Oh my God, somebody’s gonna see this article, and they’re gonna make this happen, and this is what I’ve been sitting on for a long time. Let me just do it. I don’t have any money but let me just hit my best friend up to shoot it for me, and let me just, you know, hit up people that I knew from school to star in it.’

And then it was the journey to hit upload. Like, I had done it, and you know, editing it all night, and I was like, ‘The internet is so fucking scary.’ And once I uploaded, at that time I was doing my brother’s show. I was editing, directing, producing their series, and I would see their internet comments, and they would be like, “Y’all are really suck.”

“Wow, it’s not me yet.” And so, I was like, “Yeah, what if they say, ‘Bitch, you suck?’” Get over it. ‘Cause the fear of someone else beating me to the idea was bigger than not releasing it or some internet comment calling me whack. 

Roxxy Haze: That’s… I thank you for that. Like legit, I think fear keeps a lot of us from getting where we need to get to, and I’m glad you overcame that fear because we now get to experience all the dope stuff that you’re doing, so thank you.

HIGHKEY MICRODRAMA

Never letting anything get in the way, not even yourself is how Issa continues to produce across entertainment mediums. She goes on to describe “what would be more scary than the world having access to the group chat,” and the soap operatic drama that would ensue. This is where her new venture into TikTok micro-dramas begins. If you don’t know what a micro-drama is: it’s short snippets of a dramatic narrative story split up over multiple posts on TikTok, reels, stories, and any short-form platform. They are wildly popular and keep you coming back for more to see the story unfold over each minute post. If you ask me, that is truly full circle. From YouTube shoestring budget to fully funded micro dramas. Issa said – why not? Why not explore every realm of media and give a space for all of us to play out the crazy scenarios that live rent-free in our heads. 

HIGHKEY BARRIER BREAKING

In an industry where gatekeeping is the foundation of success, Issa works to remove those barriers as best she can from her elevated position. She sees a thread and begins to sew a new pattern for everyone to be woven in. Issa Rae’s mentorship allows leverage and keen insight into navigating an industry that’s more difficult than most. 

Issa Rae: To be honest. When I first started uploading, like my first series, it was still YouTube, just posting it via Facebook. Not a lot has changed; it’s just it wasn’t monetized back then. I think that’s the difference now, is that people can– this is literally a job for a lot of people. And for me it was just like, okay, I posted it, now I still gotta figure out how else to make money.

And there are just more brand opportunities now. It’s a legitimate business. It felt like more sidelined when I was there, and even when I would meet people in Hollywood, they would just be like, “Oh, your little videos. I love your little videos.” Always put little in front of it. 

But now everybody’s trying to rush to this space and trying to figure it out because, you know, Hollywood has such a limited slot for TV shows or films.

So in some ways the more things change, the more they stay the same. And it’s just about having an understanding of how to break through with originality. Because a lot of people are doing the same things online, and I think there’s such a huge opportunity to just blow people away by doing something completely different.

Roxxy Haze: That is an interesting point. I forgot 2011 was just posting for the love of the game. It was. Just posting to do it. 

Issa Rae: For fun. 

Roxxy Haze: That’s cool. Before everybody else saw the vision, what did success look like to you, and what would you say to creatives, and I know it’s a lot out here today, who are in that stage right now?

Issa Rae: I mean the vision right is literally I love to create, that’s it. 

You know at some point I was wrapped up in a really big deal for Warner and HBO, and that was amazing, and I loved working with them, but that meant that I couldn’t do– that I could only create for them. If they said no to something, then it was no. Like, my shit just wouldn’t get made. And so now I have a, a looser deal, more of a first look with Paramount, and that’s been a really amazing relationship. It means I can go anywhere, and it also means that I have the flexibility to create things online, which is why I’m able to, you know, experiment on the fictional side with micro-series and the like.

So success to me looks like building and being able to have direct access to an audience and not having someone in the middle kind of telling me, “Yes, this is great for our audience,” or, “This is not great for our audience.” And to be able to just directly serve who I wanna serve is really exciting to me. While also being able to, like, literally make something on the web that, that has eyeballs that resonates with people, while also being able to still create my TV passion project and my film passion project.

So the success is balance and just being able to make whatever I want. 

Roxxy Haze: I think that’s a super powerful statement, especially for a lot of people out here that feel like, you know, sometimes you feel like you have to get in with the industry or something like that in order to create or put a project out.

But with social media, it has kinda eliminated the need for that. You can just directly create to your audience. So y’all make your stuff!

Issa Rae: Make your stuff, and also I think the best part of Hollywood is the marketing arm. Like, that marketing arm…To get plugged into that machine is just a different beast.

When I think about, even the best creators get millions and millions of views, the difference is still that way that a marketer knows how to package you, and the press, that combination is what takes you to the next level and it boosts your awareness. And so if you can find a way to make sure that you’re investing in marketing dollars, or you’re investing in an expert or just being creative about how you put yourself out there for that larger awareness.

Or if you do get approached by a Hollywood situation like that, what you own is priceless and they can’t replicate. But the best thing they’re good for is being able to get you on them billboards, get you on those, get the interest in talk shows or whatever the like is.

It’s just amplifying what it is that you do, and I would say that’s the benefit. 

Roxxy Haze: Thank you. I am taking notes. 

HIGHKEY LESSONS LEARNED

The road does not come without the pitfalls, and Roxxy Haze asks Issa about those moments that taught her how to move forward stronger and smarter. 

Roxxy Haze: What’s one lesson you learned the hard way?

Issa Rae: One hard lesson that I learned? There’s a couple. I mean, it’s too many, but anytime I have waited for something to figure itself out without just acknowledging it head on, it only gets worse…As soon as I felt it in my gut that something was wrong, something wasn’t a fit, something was afoot. If I didn’t act on it at the time, it just became significantly worse. So in those moments, whether it’s like, “I don’t think this is the right person to invest in my project. I don’t think this is the right actor. I don’t think this is the right collaboration.” Whatever it is, listen to your gut, and make sure that you at least have the conversation with yourself. You at least weigh the pros and cons because it will get worse.

It will not figure itself out and you’ll regret it, especially if it’s an idea that you love. 

And I guess I said the other thing is there’s also a preciousness we have about our own work. I’ve seen and worked with a lot of creators who are very, very rigidly specific about their vision and so much so that it doesn’t leave any room for collaborators, especially those who can make their project happen. So I’d say it’s really important to find the balance between what is the core that you want to keep and protect that at all costs…

If there are at least three core tenants that you’re protecting, then you have to figure out what else is valuable and what else you can live with, because in working with someone larger, you will have to compromise. It’ll be inevitable. And I’ve seen too many creatives get stuck on that. And then the vision is never realized. So I would just think about what you want to protect.

An inspiring conversation from some of the best in the entertainment game. Those who attended Dream Con and the fireside chat that day left feeling fortified and capable. At least moved to exist authentically and just make our shit!

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