Life, Values & Legacy: Our Chat with Bekah O’Shea

Bekah O’Shea shared their story and experiences with us recently and you can find our conversation below.

Good morning Bekah, we’re so happy to have you here with us and we’d love to explore your story and how you think about life and legacy and so much more. So let’s start with a question we often ask: What are you being called to do now, that you may have been afraid of before?
I’m being called into creative direction like never before—to highlight other artists, honor the modern West, and create spaces where people can shine in their truest, most authentic light. It’s a big leap from the comfort of my small studio, but this season feels larger than me. So I’m choosing courage over comfort and stepping forward.

Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Bekah O’Shea, a Montana-based designer newly stepping into the role of Creative Director—expanding my practice from the workshop to immersive storytelling. I founded Ride Free Montana, where I create heirloom leather goods alongside my husband on our family ranch. I’m also the co-owner of House of Cow Bella, a fashion house blending timeless craftsmanship with untamed artistry, and a co-producer of Coup de Rouge—a fashion and fine-art experience highlighting Western and Indigenous artistry in a way we hadn’t seen before.

Whether I’m hand-cutting leather in my workshop or working on large-scale creative productions, I’m drawn to work that feels real and rooted. I’m passionate about telling stories through fashion, imagery, and experiential moments—honoring Montana, the West, and the people who continue to shape it.

Great, so let’s dive into your journey a bit more. What’s a moment that really shaped how you see the world?
If I had to choose a single moment that shaped the way I see the world, I couldn’t—because it wasn’t just one. It’s been a series of defining moments that all led me to the same truth.

I grew up with a brother who battled childhood leukemia, and watching him face something so big with such overwhelming positivity left a permanent mark on me. Years later, when my own four-year-old daughter was diagnosed with Type 1 diabetes, I found myself confronting a fear I couldn’t outrun—the fear of not being able to fix it for my children. I knew it would be a long road, one I couldn’t shield her from. It taught me to slow down, appreciate every moment, and stop taking anything for granted.

Then, being diagnosed with cancer myself years later brought all of those lessons back to the surface—louder, clearer, more urgent. It was another reminder to keep a positive mindset, to trust God, and to release the fear and worry we hold so tightly. Each of those moments, woven together, has shaped how I walk through the world today: with gratitude, with courage, and with a deep belief that faith and perspective are what carry us through life’s hardest chapters.

It wasn’t just health that tested us. My family also lost our home in a catastrophic wildfire, which stripped everything down to its most basic truth. In a matter of moments, the things we spend so much time accumulating were gone. What remained were the people we love, the community that showed up, and the realization that what matters most in life has nothing to do with things—and that we can’t control everything, no matter how hard we try. Releasing fear and allowing God to guide us will always be at the forefront of how I walk through life.

When did you stop hiding your pain and start using it as power?
I stopped hiding my pain and began using it as power when I realized I had nothing to lose. Facing death and watching a child fight through serious health challenges changed everything. Pain stopped being something I hid and became something I carried forward with purpose. It taught me that fear is optional—and that real power lives in believing in what’s possible. Dream big. Go for it. The greatest loss is never taking the chance at all.

So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. Is the public version of you the real you?
Yes—1000%. The public version is me. I don’t know how to be anything but real.

Like anyone who’s lived a full life, I’m made up of many chapters. Each phase has shaped me and brought me to where I am now. I’ve moved through so many seasons that it took time to understand what my art even was.

I live on a ranch, I’ve moved all over the country, and my career has shifted from respiratory therapy to running a metal art business to leatherwork. I’ve lived in different places, different decades, and different styles—from ’90s grunge to Western with a little Boho mixed in. All of it is self-expression. None of it feels separate.

My work reflects that mix. I love blending influences, breaking rules, and sharing different ways of doing things—whether that’s through fashion, art, or the stories I put into the world.

Okay, so let’s keep going with one more question that means a lot to us: What is the story you hope people tell about you when you’re gone?
If I’m remembered for anything, I hope it’s for my faith in Jesus and the daring to dream big, trust Him, and follow what He placed on my heart. I hope people remember that I lived out on a limb—and invited others to come along—so we could all experience more joy, purpose, and freedom doing what we were created to do.

Contact Info:

• Website: https://Ridefreemontana.com
• Instagram: @ridefreemontana
• Facebook: Ride Free MT
• Other: @coupderouge
  @houseofcowbella

Image Credits
Michelle Falkenstine
Heidi Martincic
Duncan Vezain
Scarlette Bourne
Whitney Fay
Madison Pretty Eagle
Aspen Running Crow
Jovi Rosselotte
Stacy Michael
Mercedes LeAnn
Gena Burghoff