Rising Stars: Meet Rebecca Kassner / Kyla Helton of Cincinnati

Today we’d like to introduce you to Rebecca Kassner / Kyla Helton.

Hi Rebecca Kassner / Kyla Helton, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
One of the things that makes Chadderbox Podcast special is that it connects us with our listeners who share our enthusiasm, especially when those around us might not. It’s all about building a welcoming community of free thinkers who can share their opinions in a safe space. Kyla and I really envisioned a place where we can all take a break from reality to connect, learn, and laugh together.

Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Like most creative journeys, ours hasn’t always been smooth—but every challenge has shaped us in meaningful ways. We’ve run into unexpected tech hiccups, juggled scheduling struggles, and had to shift our posting days more than once to find a rhythm that truly works. There were moments of trial and error—testing different formats, exploring a range of topics—but through it all, we’ve stayed anchored in our passion and curiosity. What’s been most rewarding is learning what really resonates with our Chadderbox community. We’re still evolving, but every step has brought us closer to our purpose: having conversations that matter, spark thought and invite connection.

As you know, we’re big fans of you and your work. For our readers who might not be as familiar what can you tell them about what you do?
Kyla and I co-host the Chadderbox Podcast, and honestly — it’s a little bit of everything we love. We talk about topics that genuinely interest us, whether it’s pop culture, personal growth, weird internet rabbit holes, or things people are thinking about but not always saying out loud. We’re both artists at heart, so storytelling and honest conversations are a huge part of what drives us.

What makes Chadderbox different is how real it is. We don’t pretend to have it all figured out — we show up as ourselves, and we let the conversation flow naturally. Sometimes we go off track, sometimes we get deep, sometimes we laugh way too hard — but it always comes back to connection and curiosity.
I’m really proud of how far we’ve come.

When we started, we were figuring things out as we went — and in many ways, we still are — but we’ve grown so much in our confidence, our voice, and our purpose. We’ve built something that feels true to us, and that’s something I wouldn’t trade for anything.

Can you talk to us about how you think about risk?
When it comes to risk-taking, we try to lean into it — especially when it feels true to who we are. At Chadderbox, we’re not afraid to explore topics that might feel a little unconventional, layered, or even uncomfortable. We know not every episode will land with everyone, and that’s okay. The goal isn’t to play it safe — it’s to spark curiosity, challenge perspectives, and start conversations people might not be having otherwise.
Starting the podcast itself was a risk — putting our voices out into the world without knowing who would listen or how it would be received. But that leap taught us so much about trusting ourselves, taking creative chances, and letting things evolve as they’re meant to.
To us, risk isn’t about being reckless — it’s about being brave enough to try something new, even if the outcome isn’t guaranteed. And honestly, that’s where most of our growth has come from — not from playing it safe, but from being willing to take the leap.

Contact Info:

• Instagram: https://www.instagram.com/chadderbox.podcast/
• Youtube: http://www.youtube.com/@ChadderboxPodcast
• Other: https://open.spotify.com/show/6SloAe8pQ9L9CSQ2vB6meQ?si=Gqr3FaDERZW8N5vO68PCig