Still Climbing After All these Years

Stephen Sullivan (Humanities, ’88)

Braced against the elements, Stephen Sullivan (Humanities, ’88) was two weeks into an 18-day expedition up 20,308-foot Mount Denali when he was hit by seventy-mile-per-hour winds doing their best to dislodge anything not attached to the mountain. There was talk of bailing, but Sullivan and his team were resolved to finish what they had started. After hunkering down at 17K Camp for two days, they were eventually able to climb the final 3,000 feet.

Back in the real world, Sullivan couldn’t shake the wonder he felt in those high places, and he began to consider a deeper sense of purpose. He’d been entrenched in the ski-and-climbing-bum dance for most of the eight years since he graduated from Fort Lewis College. After the climb, his managerial role at Skinny Skis outdoor retail shop in Jackson Hole, Wyo., lost its sheen. So, he quit and turned his attention to designing and developing high-quality, eclectic outdoor apparel. Backed by $20,000 drained from his Skinny Skis 401K, Sullivan looped in his buddy and business partner Brian Cousins, and in 1997, the two launched Cloudveil.

“When you take those lessons learned in the mountains to heart, it changes the way you navigate decisions and partnerships,” says Sullivan. “I didn’t have my MBA or a trust fund, and I didn’t care about failing because I had nothing to lose. I’m a scrappy dude. I figured it out.”

Seven years later, Cloudveil sold for an undisclosed amount to Sport Brands International and later to Spyder. Sullivan continued to run the company, and even tried to buy it back once, but after being in “the private-equity hamster wheel” for many years, it was time to move on. He signed a year-and-a-half non-compete clause and spent time outside with his wife, Anna, and their three kids. He took a break. Kind of.

Sullivan learned a lot with Cloudveil, including “how to measure the hell out of everything.” He envisioned a better way to navigate the outdoor retail business. So, mere days after his non-compete clause expired in 2011, he launched a direct-to-consumer, analytically driven, outdoor apparel company dubbed Stio, which is Gaelic for “Stephen.”

Ten years after its inception, Stio is three times the size of Cloudveil and is growing at 50 to 60% per year. The Stio team, now over 100 employees, has not only produced award-winning outerwear but is also a three-time recipient of Outside Magazine’s “Best Places to Work” in 2018, 2019, and 2020.

“One of my strengths in my business life is that I’m good at identifying talent, hiring the best, staying out of their way, and letting them do their thing,” says Sullivan.

Though Sullivan was raised by two professors, he was far more interested in playing in the mountains. Thankfully, he got accepted to one Colorado institution that ticked both the outdoor recreation and academic boxes, and enrolled at Fort Lewis College in 1983. He worked at Pine Needle Mountaineering throughout his time as a student at FLC, which offered him his first glimpse into the outdoor retail world.

When he wasn’t working, he spent the better part of his time in Durango’s classroom of the great outdoors. The San Juan Mountains served as the backdrop for countless running, cycling, fly-fishing, and skiing forays with a group of cronies that still meets for annual trips around the world. He also took a kayak class with Dolph Kuss in the newly hatched Outdoor Pursuits program. After the course, a buddy took him on the upper Animas River. Sullivan recalls swimming—a lot—and he hasn’t been back in a kayak since.

Back on campus, Sullivan served in student government and took a hodgepodge of history, political science, and art courses, and one rogue business class, graduating with a Humanities degree. In those days, students were required to take multiple semesters of writing composition courses, which Sullivan credits for learning to write well, a skill that has served him throughout his life.

“There’s something different about going to school in the mountains,” says Sullivan. “There are a lot of lessons to be learned there. I don’t think I could’ve ended up in a better place or gotten a better education. The attention from and access to professors is outstanding. They’re always trying to move you forward as an individual. I still reflect often on lessons learned from my time in Durango.”

After graduation, Sullivan moved to Boulder, Colo., and worked at a snowboard retail store before moving to San Francisco for a brief stint climbing the corporate ladder. In 1989, an FLC pal, Scott Richards, visited over Thanksgiving and told Sullivan he was moving to Jackson, Wyo. On the freeway to work, Sullivan couldn’t shake the vision of endless powder days structuring his time instead of city commutes. These musings made him miss his exit, twice. The next day, he quit his job, wired Richards $500 for a down payment on the first-month’s rent, packed his VW bug with everything he owned, and drove to Jackson.

Thirty years later, Sullivan is one of Jackson’s most prominent community leaders, currently serving as a board member for the Jackson Hole One Fly Foundation and Center Management, Inc. He’s also a frequent panelist and lecturer in the outdoor recreation industry and serves as a business mentor for several companies.

When he’s not working, volunteering, or shuttling his kids to youth sporting events around the West, Sullivan is still playing hard in the mountains or working on his ranch. He sleeps really well and keeps dreaming dreams inspired by high places.