Becoming An Event Operations Unicorn with Kesha Moore
If you need someone who can walk into any room (or roll into it!) and make an 8,000-person event run like clockwork, Kesha Moore is your person. And if you need someone who will tell you the honest, unfiltered truth about the events industry, single motherhood, hustle culture, and why you absolutely need to sleep when the baby sleeps? Also, Kesha Moore.
This week on The Chaotic Middle, I sat down with Kesha Moore, founder of Rolling with Kiki, event operations unicorn (her LinkedIn's words, and they are correct), mentor, comedian, and one of the most genuinely joyful humans to ever grace this podcast.
Based in Raleigh, North Carolina, Kesha has spent more than 20 years leading full life cycle meeting and event operations, from corporate conferences to global summits, all while navigating single motherhood, disability, autoimmune challenges, and a world that wasn't always built with her in mind.
She's still standing. She's still rolling. And she is absolutely the GOAT, her 21-year-old son confirmed it.
How You Fall Into a Career You Were Born For
Kesha didn't go to school for events. Nobody handed her a roadmap. She fell into it, the way a lot of the best people in any industry do, by accident, curiosity, and a whole lot of saying yes.
It started at Blue Cross Blue Shield of North Carolina, where she took a temp job that had nothing to do with events. She kept asking her manager to let her plan one. Finally, the manager agreed.
Her first event was a family day for 8,000 people. Food, rides, games, face painting, bands, Tai Chi, and fireworks.
"At the end of it, it was like, oh my god, I can do this. So that kind of started my journey."
She kept finding her way back to events through every job she held. She was always the one volunteering to plan something, always the one who could walk into a room full of chaos and turn it into something that worked. After more than two decades of doing it for everyone else, she finally decided to do it for herself.
Rolling with Kiki was born, named, in part, because Kesha uses a mobility scooter to get around, and because, honestly, who doesn't want to be rolling with Kiki?
"I am everyone's favorite big black disabled event planner. And the name just kind of stuck."
Single Mom, Full-Time Career, Zero Rulebook
Kesha's son was born in 2005, right in the middle of a career that required long hours and frequent travel. Being a single parent in an industry that doesn't slow down for anyone is not for the faint of heart, and Kesha is the first to say she didn't have a manual for it.
What she did have was remote work, a strong support system, and a son who somehow turned out to be one of the most grounded, even-keeled humans she knows.
"He mentioned like, 'Mom, I'm so glad you're the first person I see when I wake up in the morning. You're the first person I see when I walk through the door.' Just being here — that mattered."
Building community around herself made the difference between surviving and thriving. And when her son got old enough to understand that travel was how mama kept the lights on, he became one of her biggest supporters.
Now he's 21, still lives at home, calls her the GOAT, and laughs at her jokes. By any measure, that's a win.
Anti-Hustle Culture Is Not a Vibe
If you are waiting for permission to stop grinding yourself into the ground, consider this your sign. Kesha Moore, event operations unicorn, is firmly, loudly, and unapologetically anti-hustle culture.
"I am very anti-hustle culture. I do not subscribe to girl boss, hustle, fake it till you make it, any of those things. I'm almost 50. I am tired."
And she means it, not just philosophically, but physically. Kesha lives with lupus and mobility challenges that require her to work with her body instead of against it. Five years ago, what she thought was COVID turned out to be blood clots in her lungs. She spent two weeks in the hospital. Her mobility challenges began there.
"If you do not take care of your body and make those stops, your body will stop for you."
She was honest that even after that health scare, it took time to actually slow down. She came back part-time, then full-time, then right back to 14 and 15-hour event days like nothing had happened. The lesson didn't land immediately. But it landed.
Now? She takes a nap at 2 pm if she needs one. She tells her clients that if they think they need her after 9 pm on an event day, they don't. She uses AI for administrative tasks, so her energy goes where it matters. And she is medicated – proudly, loudly, and with a t-shirt that says "Talk to Jesus and a trained professional."
"If you want 100% full throttle Kiki, you have to let Kiki take a nap."
Running Events with a Disability: The Real Talk
Managing events that run 14+ hours a day with an autoimmune condition and mobility challenges requires a level of planning and self-advocacy that most people don't see behind the scenes.
Before every event, Kesha starts taking immune-support supplements two weeks in advance. She gets the latest vaccine booster a month before traveling so her body can acclimate. She masks in airports without exception — something about recycled airplane air, she says, and she's not wrong. She washes her hands. She prays. And then she shows up and does the job.
"It's not only about making sure I don't get anything. It's also about making sure I don't give anybody anything."
She's also learned to advocate for her boundaries in a space that can be relentless. She's up at 4 am to get ready for a 7 am call time. She has muscle relaxers ready for when her body starts screaming. And she has set a firm, non-negotiable cutoff: after 9 pm, call Jesus or 911. Kesha is unavailable.
The scooter, by the way, does not mean she doesn't get tired.
"Tired is tired. I don't care if I'm sitting, standing, rolling, flying, whatever."
Paying It Forward: Mentorship and Representation in the Events Industry
Here's a statistic that stopped the conversation cold: only 13% of people in the hospitality industry are Black. Of those, only 8% are women.
Kesha knows those numbers. And she's doing something about it.
Through the Annabelle Project and Beyond the Ballroom, Kesha mentors young Black women who are transitioning from college into the events and hospitality industry. She gives them what she didn't have: someone who looks like them, who's been in those rooms, who will tell them not just what the textbook says but what actually happens when the CEO is yelling, the catering director is frustrated, and the AV tech is about to walk out.
"The book is going to tell you about crisis management. But it's not going to tell you what to do when you've got the CEO yelling at you and the catering director is mad and the AV tech is done. Those are the types of things you won't find in a textbook. That's where I come in."
She describes herself as her mentees' fairy godmother, giving them the real deal on what it means to step into an event space as a Black woman, because that experience is specific, and it matters.
She was mentored, unofficially, by Joan Eisenstein, someone she calls the godmother of the events industry, with 50-plus years in the business. The impact of having someone like that open a door for her is not lost on Kesha. She can never repay that. But she can pay it forward.
"How dare I not do that for the next person? I can never pay Joan back. But I'm going to pay it forward."
And her philosophy on the scarcity mindset that sometimes shows up in leadership spaces — the fear that someone else's success dilutes your own? She's not having it.
"If anything, it strengthens it. I need to pave the way to make it easier for the next person who looks like me."
Just Be a Good Human Being
One of the most quotable moments in this entire conversation came near the end, when Kesha summed up her entire life philosophy in four words:
"Just be a good human being. And if you can't be, stay home."
She doesn't care about your background, your identity, or your credentials. If she can help you, she will. If her skills and gifts can serve you, whether in events, business operations, or mentorship, she's going to use them. Because they weren't given to her to keep to herself.
That's the kind of energy that changes rooms. And industries. And the people lucky enough to be in conversation with her.
Answering the Chaotic Questions
At the end of every episode, I ask each guest the same three questions. Here's how Kesha answered:
If you could go back and talk to your 2005 self, what would you tell her?
"Leave now. I was in an abusive marriage and tried to stay for the sake of the baby. Leave now. It's not going to get any better."
A new mom comes to you for advice. What's the first thing you tell her?
"Sleep when the baby is sleeping. Do not fall into the 'clean while the baby sleeps' trap. Lay your tail down, too. And throw away What to Expect When You're Expecting — use it to level out a table leg. Every woman is different. Every baby is different."
What do you hope your son remembers about you as his mom?
"That I never gave up. I may have paused a couple of times, but I never gave up. And that I loved him. Every choice I made, it always had his best interest at heart."
Where to Find Kesha
You can find Kesha and learn more about Rolling with Kiki at rollingwithkiki.com and reach her by email at hello@rollingwithkiki.com. She's also on LinkedIn under Lakesha Moore, DES, and she'd like you to include those initials, because she earned every single one of them.
Ready to Hear More Stories Like This?
If you couldn’t tell by listening, Kiki and I had an absolute blast. She is the type of person that you just can’t help but laugh around. Her energy is infectious and her ambition is straight-up inspiring. I can see why she’s so good at her job. Who wouldn’t want to roll with Kiki?!
If this conversation inspired you, you're going to love The Chaotic Middle Podcast, where we feature real stories from real people navigating the beautiful mess of work, life, motherhood, and everything in between.
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