Black List: Kyra Kyles, writer, creator, public speaker, entrepreneur

Kyra Kyles

 
Kyra Kyles is a multi-platform senior-level media executive, a public speaker on issues of diversity and representation, and an award-winning writer.
 

Journalist
Kyra, former EBONY Editor in Chief / Senior Vice President, Head of Digital Editorial, is a decorated multimedia journalist, TV personality, content producer and humor writer who originally joined the historic Black-owned brand as a Senior Editor for JET magazine in 2011 before jet-setting over to run the site, its all-digital form as an app, and eventually EBONY.com and the media mothership itself.

Prior to those roles, Kyra worked for the Tribune Company’s millennial outlet, RedEye, where she achieved unprecedented levels of audience engagement for projects including a WGN-TV nightly pop culture / humor segment called The Kyles Files, an interactive music competition for indie artists, The Track Off, and the mother of all mumblemouth rapper mockeries: Ringtone Rap Project.

 
Multiple award recipient
Kyra has been named to the Folio magazine Top 100 media executives WVON and Ariel Capital’s Top 40 Under 40 Game Changers and Chicago Defender’s 40 Under 40 to Watch lists.

She won the coveted Jones-Beck Award from the Tribune for her work turning a humble public transit column, “Going Public,” into must-read material and an ongoing TV segment on then-Tribune sister stations.

 
Speaker
A staunch opponent of whitewashing and mansplaining, this diversity and digital expert speaks on that very topic for international venues including as WOKE Entrepreneur Conference, Social Media Week, Digital Strategy Innovation, the 21 Summit (formerly known as the Blavity EmpowerHER Summit), the inaugural Haiti Tech Summit, and the A3C Music Conference.

 
Entrepreneur
In addition to a 20-plus year journalism career, Kyra co-owns a production company, Myth Lab Entertainment.

Myth Lab’s Human Resources sci fi series, a puppet-populated send-up of the ruthlessness of corporate America won Kyra and her sister Kozi, who created the concept, an LA WEBFEST Award, a number of industry write-ups and the opportunity to work with a guy you might know as the most beloved, though totally not real, TSA agent in the known world, Lil Rel Howery.

The sequel to that series Human Resources: Cubicle Creepshow, debuted in March of 2018, this time matching up workplace horror stories with monster movie classics.

 
Volunteer
Not one to laze about, Kyra is former two-time President of the National Association of Black Journalists-Chicago chapter; a board member for acclaimed indie streaming service kweliTV; a board member for streaming service PLATFORMZ, and serves on the board of advisors for Dream on Education.

She also is a tutor for the Mercy Home for Girls in the South Side of Chicago.

 
Wildcat
Last, but not least, this media move-maker is a proud alum of the esteemed Northwestern University Medill School of Journalism where she earned two degrees in four years as part of an accelerated master’s program.

 
OVERTIME OF DEATH (WEREWOLF PARODY) | CUBICLE CREEPSHOW

 
 

What was your first break? My first big break as a writer occurred when I was a senior in Northwestern University’s Medill School of Journalism. I was in an accelerated master’s program and so we got to attend classes mostly in downtown Chicago and because of this, many media luminaries dropped by as guest speakers because it was much more convenient than coming to the campus in Evanston. One of our lecturers, Jim DeRogatis, then at the Chicago Sun-Times, visited one of our classes and talked about NWA. As the likely sole hip-hop enthusiast in the room and disagreeing with a few of his points about my “Straight Outta Compton” faves, I spoke up about something that Jim said about problematic lyrics and themes. Okay, I spoke out a few times. Animatedly. Not too long after, I received a call from my professor and thought I’d gotten myself into some hot water by having such a spirited dialogue with a guest, but it turned out that Jim wanted to invite me to write rap reviews for the Sun-Times. I ended up graduating with bylines from a respected Chicago publication and the opportunity to put a spotlight on deserving Chicago talent. I continued that mission further along in my career as a reporter and pop culture columnist at the Tribune RedEye where I then launched a digital-to-print talent competition called The Track-off.
 

Worst thing that ever happened to you to remind you that you are Black? I NEVER need a reminder that I am Black, though unfortunately, some have gone to great pains to make me feel my “otherness” even when it isn’t relevant. One of the most memorable of those occasions took place in high school when one of the teachers, most likely as an act of inspiration, asked us to go around the room and reveal where we had gotten into college. Here I am, one of the top students and taking AP courses, yet I vividly recall a White student giggling when I said I’d been admitted to institutions including Yale, University of Chicago and my eventual alma mater of Northwestern University. He even had the audacity to remark “affirmative action at its finest. Mind you, he happened to be one of the lowest-performing students in the class. There is nothing wrong with affirmative action and in fact, it’s sad that deliberate efforts to keep Blacks out of higher learning is why it exists. Still, I remember thinking how scornful and nasty he sounded and it was impressed upon me that we are so often doubted in our abilities. I did remind him of his own sorry GPA and that affirmative action students weren’t what was keeping him out of top colleges.

Another time, and this is very casual, but I was at an after-work party with a fellow journalist, who is White, and one of her friends came up, introduced himself and started telling me this convoluted story about how uncomfortable he was at a “plantation-themed” party he attended some years back. I asked him how he got to THAT topic, versus talking about (I dunno) our shared profession, current movies, favorite TV shows, or even the weather. I never got a straight answer but I think you get my point.
 

Best thing to ever happen to you to remind you that you are Black? Every day I am blessed to be Black. We are truly resilient human beings who come from even more resilient generations who paved the way for us to be here. My mother lived during a time where there were “colored balconies” in theaters and rules against Black people trying on clothes in department stores because other customers wouldn’t want to touch them afterward. A friend’s grandfather used to tell us stories of crossing the street in the South to avoid racist Whites who would seek confrontation. Segregation and in-your-face discrimination isn’t as distant in the past as some would like us to think. That’s why, in the words of Issa Rae, I am rooting for everybody Black. I think it’s important for us to understand that such a thing is necessary to even come close to compensating for the obstacles and challenges we face simply because of systemic racism. So many opportunities are delayed for us, and for no good reason, so when we get them, we should collectively celebrate without a hint of hesitation.
 

Work you are most proud of? I am proud of my 20-year journalism/speaking career as well as several purely creative indie projects I’ve been involved in, including the Web series I co-produced/directed/wrote with my sister, writing partner and BFF Kozi Kyles. We launched “HR the Series” Seasons 1 and 2 using our own money, resources, imaginations and by finding some of the most talented people possible. The concept, which is like “The Office” meets “Outer Limits,” was born out of a fever dream Kozi had after witnessing some horribly handled layoffs. A few years later, we were able to bring that first iteration of her vision to life with custom-made puppets and even a cameo with now-Hollywood champ and one of my favorite RedEye interviewees of all time, Lil Rel. It was affirming to win acclaim and awards for our efforts, plus it’s always more fun to succeed when you do it with someone you love and respect.

I am also very proud of the editorial work I’ve done over the years examining the intersection of race, class, gender and pop culture. Coming up, my next project that I’m “pre-proud” of is a non-fiction book that centers, and will hopefully provide valuable insights about, the experience of being a Black woman in America. It’ll be a healthy serving of Black History blended with our contemporary racial situation, so please stay tuned for that!
 

How has the business changed since you broke in? Journalism has changed in that there is a lot more audience engagement and crowd participation. When I started, we’d be living in fear of e-mails or letters from readers. Now, there’s this instantaneous editorial board on platforms like Twitter. I don’t mind the instant feedback though because, despite the occasional tendency toward a mob mentality, it keeps the industry honest and cognizant of their biases. Hearing different voices, especially if they are not on staff in a newsroom, is critical to improving the editorial product. As I often say to brands who want to operate like it’s the 1950s, #DiversifyOrDie.
 

Trapped on an island, what essentials must you have? My creative essentials would be my laptop, solar-powered laptop battery, my phone, some WiFi and my Kindle. I may bring a few physical copies of books too. I tend toward thrillers/sci fi in my preference for reading and writing, so I’d love to have Octavia Butler, Stephen King, Shirley Jackson and Ray Bradbury with me. I’m also in literary love with the recently released “My Sister’s a Serial Killer” by Oyinkan Braithwaite. I’d take some Jordan Peele scripts along as well.
 

If you had a time machine, what would you say to your past self? I feel that I’ve followed my passions to a large degree, which is great, but there are certainly times I let what an employer needed delay my path. I think I would have chosen to take some sabbaticals and do some more independent projects along the way. However, through my company with my sister (Myth Lab Entertainment) I’ve been able to establish an outlet for independent initiatives as well as work on projects like my upcoming books in the fiction and non-fiction categories.
 

If you could have a one-on-one with anyone who would it be? And why? There are so many people to have a one-on-one with and it almost pains me to choose one. I’ve met other Black content creators I admire, such as Issa Rae, Kenya Barris and Ava DuVernay, during my work as Editor-in-Chief at an iconic African American magazine.

I’d also love to sit down with the surrealist genius known as Terence Nance. I am transfixed by his work, including HBO’s “Random Acts of Flyness” and he is another individual who presents a nuanced portrayal of Black life and the hypocrisies we are forced to face and overcome.

 
To see the up-to-date Reel Black List, click here.