We were lucky to catch up with Kyle Olson recently and have shared our conversation below.

Kyle, looking forward to hearing all of your stories today. Looking back on your career, have you ever worked with a great leader or boss? We’d love to hear about the experience and what you think made them such a great leader.

Who’s the best boss I’ve ever had? I’ve had some good ones – but Matt Hensley takes the cake. He’s someone who truly gets it. Maybe it’s because we both hail from Wisconsin, but it felt like we were on the same wavelength right from the start, sharing values that made us a great team.

I’ve had my fair share of tough gigs, but the projects I’ve worked on with Matt? They were something else. We dealt with the biggest of names, complex logistics, and the kind of travel that turns your suitcase into a home. It’s the kind of hard that teaches you what you’re made of. To say it was challenging would be an understatement.

On set, when the stress levels rise, you really start to see who people are — Hollywood is full of colorful characters, and not all of them are easy to handle when the pressure’s up. But my little trick for getting by is that I always try and find a reason to laugh. Because at the end of the day, we’re making TV shows, not solving world peace. What other industry would you find yourself coordinating a last-minute llama cameo or pacifying a diva parrot insistent on a trailer bigger than the lead actor’s?

Matt has an uncanny ability to not just partake in these moments of levity but to elevate them. He was right there with me. He had this knack for turning a laugh into the best medicine for on-set stress. He didn’t just lighten the mood; he made the toughest times feel like a scene out of a sitcom. His laughter wasn’t just about fun, though; it was a sign of trust and validation – and that meant everything.

Working with Matt, I always find myself actually looking forward to the challenges, because I knew we’d tackle them with a good dose of humor. It’s that kind of working relationship that turns a job into something you can’t wait to get back to, day after day. And in my opinion – that’s the hallmark of not just a boss, but a true leader.

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.

I am a TV/film producer – but really, I consider myself a storyteller. I just love telling a story no matter what the medium.

As a kid, the spell was cast. Trips to Disney World weren’t just rides and cotton candy; they were my first taste of magic. Especially the Disney MGM Studios and Universal—back then, it wasn’t just about being in a movie; it was about the craft of creating one. And boy, did that bug bite me hard. I knew I had to be part of that story-making alchemy.

Fast-forward to LA, where my journey took a serendipitous turn. Teaching film to high schoolers after hours, I caught the eye of the American Red Cross. Initially hesitant, I soon discovered this gig would put me right where I dreamed: the hallowed grounds of studio lots. There, among the giants of Disney, Universal, and Paramount, I found mentors who lifted the curtain to the industry I longed to join.

Then, in a twist that felt like a scripted moment, I taught a private class to none other than Tyra Banks. Our chat about breaking into the biz led to her offering me a golden ticket—an opportunity on ‘America’s Next Top Model.’ Just like that, I was in the door. From there, it’s been a climb, a wonderful, relentless climb. I’ve had a hand in bringing to life an array of stories – in a myriad of roles. Recent projects include ‘Barbie’, ‘House of the Dragon’, and ‘Masters of the Air.’

One project that really marked a pivotal moment in my career was ‘The Last Signal.’ It’s a documentary about two World War II veterans who reunite for the first time in 70 years after their inaugural voyage on navy ship LST-218. That piece of history didn’t just win an Emmy; it won hearts, and in many ways – that was the most satisfying part.

Podcasting is my latest frontier—another stage for storytelling. ‘love & justice’ delves into the chilling murder mystery of Ashleigh Love, earning its stripes among listeners and critics alike. The series became a Top 25 Apple podcast and was nominated for a prestigious WEBBY Award in 2023; nominated in a category alongside Tom Hanks. It was also named as one of Biography’s Top 15 Best True Crime Podcasts of all time.

And now, ‘Kyle on the aisle’ is my latest journey, peeling back the curtains of Hollywood’s untold stories. It’s fresh, it’s exciting, and if my gut’s right, we’re just getting started. There’s a whole lot more to come, and I’m just warming up!

What’s the most rewarding aspect of being a creative in your experience?

The most rewarding aspect? It’s the rush—the unparalleled high of creation and connection. Being in this industry is akin to chasing a particularly intoxicating kind of dragon. You’re always seeking that next moment of elation, that next breakthrough where your vision comes to life and resonates with an audience.

Each project is a new adventure, a fresh canvas where ideas morph into stories that have the power to move, to entertain, to provoke thought, and even to inspire change. The journey from conception to the final reveal is exhilarating; it’s full of ups and downs, twists and turns, but the destination? It’s electric.

When you see the spark in someone’s eyes as they engage with your work, when you hear the discussions it ignites, the emotions it evokes—there’s nothing quite like it. It’s a feeling of shared humanity, of having reached out and touched the soul of another through the language of creativity. And when the lights come up, and the audience carries a piece of your story with them, that’s when you know you’ve not just told a story, but you’ve woven it into the fabric of someone else’s experience.

This connection, this shared heartbeat between creator and audience, is the most potent drug for any artist. It drives you to push boundaries, to explore new horizons, and to return to the creative well again and again. It’s a cycle of renewal and discovery that I find myself grateful to be ensnared in—it’s the kind of addiction that gives more than it takes, leaving both the creator and the beholder richer for the experience.

Is there a particular goal or mission driving your creative journey?

Driving my creative journey is a dual ambition: to make those closest to me—my family and friends—feel a sense of pride in the work I do, and to leave an indelible mark on the landscape of storytelling. While my roots in South Milwaukee are an integral part of who I am, they serve more as a steady compass than a constant beacon. I aspire to take the resilience and grounded perspective that my upbringing has given me and channel it into creating stories that resonate on a universal scale.

I strive to illuminate the untold tales, the narratives that linger in the shadows, waiting for their moment in the spotlight. I’m drawn to stories that haven’t yet been seen or heard — the ones that challenge perspectives, that offer a fresh lens on the world, and that, perhaps, might have remained whispers if not for the chance to be told.

Every script I write, every scene I shoot, and every podcast I record, I’m guided by the aspiration to push beyond the familiar horizon, to explore the uncharted territories of human experience. It’s about crafting work that speaks to the curious, the open-hearted, and the adventurous spirit in us all.

Contact Info:

• Website: www.KyleCOlson.com
• Instagram: @HollywoodTinman
• Linkedin: https://www.linkedin.com/in/kyle-olson-a19a186/
• Twitter: @HollywoodTinman
• Other: www.kyleontheaisle.com www.loveandjusticepodcast.com

Image Credits
Willy SanJuan, Tracie Hunter, Marcus Taplin, Shelby Carol Cude