We’re excited to introduce you to the always interesting and insightful Jonathan Giles. We hope you’ll enjoy our conversation with Jonathan below.

Jonathan, appreciate you joining us today. If you could go back in time do you wish you had started your creative career sooner or later?

I think sometimes it’s easy to look back and say what if…

When I was graduating from college, I interviewed with Cartoon Network for their internship program. To this day, it’s one of the best interviews I’ve ever had. The recruiter and I—total vibes. At the end, she asked, “If there was any other job you could do, what would it be?”

I instantly blurted out, “I would write for Saturday Night Live!” I didn’t plan to say it. I’m not even sure I’d seriously considered it as a real option. It just came out.

Years later, I’ve come to realize that your passion or dream job isn’t always the “right” answer in a job interview—but like I said, we were vibing. I thought it was a safe space. [laughs]

Turns out, she had been a page at 30 Rock when she was younger, and because it had been such a formative experience for her, she told me she wasn’t going to hire me for that internship—or at least, that’s what she said—because she wanted me to chase that dream of writing for SNL. That sounded nice… but at the time, I had no idea how to even begin.

It wasn’t until ten years later—after doing stand-up, performing improv, and exploring sketch writing—that I crossed paths with individuals at NBC who were truly passionate about discovering and developing underrepresented creative voices. Thankfully, they believed in me and selected me to participate in the NBC Talent and Development Initiative.

The rest is kind of history. But all that to say: you can spend your life looking in the rearview mirror, wondering what if. Personally, I think the windshield is much bigger—and what’s ahead matters more than what’s behind.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

II’m a storyteller at heart—whether through scripted content, live performance, or immersive experiences. I write, produce, and develop work that explores identity, duality, power, and joy—often through a lens that centers around Black and underrepresented voices.

Although my professional career began in late night and variety television, I’ve always been drawn to genre-bending, emotionally rich storytelling—the kind that lives somewhere between the surreal and the deeply human. Think Watchmen, Lovecraft Country, Stranger Things, Everything Everywhere All At Once.

When I first started taking meetings as a writer, I’d often get asked, “But you do stand-up… how did you write this deep, emotionally moving story?” I didn’t always know how to answer that. But over time, I realized that even in comedy, what interests me most—what’s at the heart of every punchline—is the question: How did this make me feel? And why?

Comedy, to me, is a universal language—it connects us through joy, but often through pain too. I think that’s what sets my work apart: the balance of heart and edge. Storytelling that’s fearless but grounded, playful but purposeful. I’m most proud of building a creative practice that’s both honest and vulnerable.

That belief is part of what inspired my latest project, REPENT—a comedy storytelling show where performers confess the hilarious secrets they’ve been dying to tell. Our first show debuts May 8th in Atlanta, and I can’t wait for folks to see what we’re building here in the South.

Whether you’re a collaborator, a client, or a curious viewer, my goal is the same: to make work that moves you.

How about pivoting – can you share the story of a time you’ve had to pivot?

Absolutely. I think that’s something we’re all experiencing right now, no matter the industry. Whether you’re a writer, musician, actor, running a lawn care service, or working at an ad agency—we’re all just trying to figure it out.

For me, the Writers’ Strike was incredibly tough. We were already coming off the heels of COVID, where so many writing jobs and opportunities I’d been pursuing were suddenly put on indefinite hold. And just as things started to pick back up, the strike hit—and honestly, it kind of broke me. No lie. [laughs]

But in hindsight, I think it’s exactly what I needed. It forced me to take a hard look at what I truly wanted—not based on what the industry was telling me to chase, but based on what actually brought me joy. That clarity is what inspired me to move back home to Atlanta. To plant roots.

I started my company Nice To Meet You Productions, because I wanted to build something meaningful in the city that really has my heart. I’ve met some amazing creative collaboraters here and, in our own way we all have expressed a desire shine a light on the incredible talent and community that makes this city great. ‘Cause Atlanta got something to say!

Don’t get me wrong—I’m not getting Ryan Coogler offers (yet). But I’m having fun, I’m building community, and I’m excited about where we’re headed.

How can we best help foster a strong, supportive environment for artists and creatives?

Go support live shows! Did I mention I have one every second Thursday? Our first is May 8th here in Atlanta! Tickets are at www.repentstories.com [laughs]

Here’s what I won’t do: I’m not going to talk down about content creators or stand-up comics who post crowd work clips or lean into social media. Criticizing how other people express their creativity is tired. Platforms like Instagram and TikTok have made it easier than ever to discover new voices that align with your personal taste and worldview—and that’s powerful.

But I also think that’s where society gets stuck. The algorithm can trap us in bubbles. Unless it’s in the comment sections, we don’t have to engage with people who challenge our perspective. We end up surrounded—digitally and sometimes physically—by folks who look, think, and act just like us. That limits us.

One of the best things we can do is spend time around people we may not completely agree with—and just listen. Not to debate, not to change minds, but to understand where someone else is coming from. That kind of empathy is at the heart of great storytelling—and a healthy society.

And hey, even if you don’t walk away seeing eye to eye… they might still offer you a beer and a ride on their boat.

Contact Info:

• Website: https://www.repentstories.com
• Instagram: https://www.instagram.com/repentstories
• Other: If allowed a second instagram account www.instagram.com/jgileswrites

Image Credits

Photographers: Annie Elizabeth, Greg Feiner, Lola Scott and Sam Spitalny,