How Courtney Despos Built Skeyo After Leaving the Corporate World

For Courtney Despos, the outdoors has never been just a place to visit. It has always been part of who she is. From childhood road trips between snow-covered mountains and sun-soaked coastlines to competitive snowboarding and days spent fly fishing, her life has been shaped by a deep connection to adventure. Today, that connection has evolved into something bigger: Skeyo, an outdoor gear company born from a simple idea and a desire to make the adventures she loves easier to protect.

But her path to entrepreneurship wasn't a straight line down the mountain. With a degree in physical therapy, Despos graduated in 2008 and spent years climbing the corporate ladder in Alaska, eventually becoming a corporate vice president by 2014. Still, the traditional path never fully satisfied her desire for independence or her appetite for adventure.

In 2016, following the loss of her father, Despos stepped away for a roughly year-long sabbatical, trading office routines for fly shops, guiding and river days. The experience was transformative, but she eventually returned to corporate life for stability. Motherhood reshaped her thinking further: as her son, Braxton, grew older, she began mapping out a plan to become work-optional by the time he turned 18, with the freedom to chase outdoor experiences on her own schedule. That vision would become the foundation for Skeyo.

An Idea Born From a Common Outdoor Frustration

The concept behind Skeyo began taking shape in 2022, emerging from conversations with a friend about products designed to protect outdoor equipment. Despos started researching the market and quickly noticed a gap. While outdoor enthusiasts had plenty of options for transporting their gear, there was little available that addressed the specific challenges of protecting equipment mounted outside a vehicle.

One image in particular helped crystallize the problem: a ski rack with skis wrapped in bedsheets.

It was a familiar workaround, but one that highlighted an obvious opportunity. Why weren't there purpose-built products designed to protect skis and snowboards while they were mounted outside?

In early 2023, Despos took her research online, searching Reddit and other resources for anything that resembled the product she envisioned. She found very little that matched her idea. The more she researched, the more convinced she became that there was room for something different.

Skeyo was incorporated in 2023, turning an idea into a legitimate business venture. The goal was simple: gear tough enough to handle the weather and the road, built specifically to protect skis and snowboards mounted outside a vehicle, so riders could stop worrying about their equipment and get back to the mountain.

For Despos, however, the mission has never been about simply selling bags.

"I'm not in love with bags, but I am in love with protecting the adventure and ways to do that."

Ski and snowboard equipment are just the beginning. Her long-term vision is to expand into other sports and create products that help people spend less time worrying about their gear and more time enjoying the experiences that matter.

When the Unexpected Changes Everything

Just as Skeyo was beginning to take shape, Despos experienced an unexpected setback that would ultimately give her business a different kind of momentum.

In 2024, while snowboarding at Mammoth Mountain, she broke both of her ankles. The injury dramatically changed her ability to travel, get outside and pursue the activities that had always been central to her life. Recovery forced her to slow down and reconsider what came next.

Looking back, she sees the accident as a turning point. What initially felt like an interruption became an unexpected opportunity to focus on Skeyo's research and development. It was another reminder that life can change overnight, sometimes redirecting an entire journey.

Then came another unexpected gift: a challenging winter season.

The poor snow conditions of the 2025–2026 season turned out to be a blessing in disguise. As the first production run of Skeyo ski and snowboard bags arrived, extensive testing revealed that the products weren't meeting the company's quality standards. Despite multiple rounds of sampling and development, Despos estimates that roughly 70 percent of the bags were falling short of her standards.

For a new company, that could have been a devastating setback. Instead, Despos chose to see it as an opportunity to get things right.

Rather than rush an imperfect product to market, she went back to the drawing board. Version two has now arrived at the warehouse, bringing the company closer to the quality and performance standards she envisioned from the beginning. She is also exploring ways to repurpose the materials from the first production run into practical, sustainable products rather than letting them go to waste.

For Despos, building a business means being willing to make difficult decisions, even when they involve starting over.

Finding Momentum in the Outdoor Community

One of the most encouraging moments in Skeyo's development came during REI Outside Days, in Denver this past May of 2026. There, Despos had the opportunity to introduce the concept to outdoor enthusiasts and see their reactions firsthand.

What stood out wasn't simply that people liked the products. It was how surprised they were that something like this didn't already exist.

That response reinforced the market opportunity she had identified during her early research. The problem was real, the need was familiar, and outdoor enthusiasts immediately understood the value of a purpose-built solution.

It also reinforced something Despos has come to appreciate about the outdoor industry: the strength of its community.

Building a business can be isolating, particularly when navigating manufacturing challenges, product development and the uncertainty of launching something new. Yet she has found tremendous encouragement from other founders who are willing to share advice, offer support and help one another navigate the inevitable challenges.

She believes those relationships are essential to long-term success.

"Your network is your net worth," she says, emphasizing the importance of recognizing which bridges need to be built and which ones may need to be burned.

It's a philosophy shaped by experience, both in the corporate world and in the outdoor community. Success isn't just about having a good idea or creating a great product. It's also about surrounding yourself with people who understand the journey and are willing to help you move forward.

A Different Definition of Success

If her younger self could see the life she is building today, Despos suspects she would be speechless. Growing up, she imagined a fairly traditional path: pursue a career, climb the corporate ladder and become a successful business leader. She accomplished much of that, reaching an executive position at a relatively young age.

But her definition of success has evolved.

Watching her father retire early helped shape her desire for financial independence and the freedom to choose how she spends her time. Now, rather than measuring success solely through professional titles or corporate accomplishments, she sees it through the experiences she can create, the time she can spend outdoors and the opportunities she can give herself and her family.

Her journey has also brought her full circle on the slopes. After years of snowboarding, and a significant injury at Mammoth, she has recently transitioned back to skiing. Beaver Creek remains her home mountain, a place that connects her childhood memories with the person she has become.

Looking toward the next decade, Despos hopes to play a role in making outdoor experiences more accessible and convenient through thoughtful product innovation. She wants Skeyo to grow beyond its initial offerings, continuing to identify overlooked problems and develop solutions that protect the equipment people rely on to pursue their passions.

Ultimately, her story is about more than leaving corporate life to launch an outdoor brand. It's about recognizing when a different path is calling, having the courage to pursue it and understanding that even the unexpected detours can lead somewhere meaningful.

From physical therapy offices in Alaska to fly-fishing rivers, corporate boardrooms, mountain slopes and the warehouse where Skeyo's next generation of products is taking shape, Despos has built a life around adaptability and adventure.

And while the next chapter is still unfolding, the next concrete step is already underway: with version two bags now at the warehouse and available online, one step closer to the company she set out to build.

Learn more about Skeyo and shop its gear at skeyooutdoors.com.