Wilson Gillespie: 'I am the richest man I know'

Wilson Gillespie (second from right) with friends in Whitefish, MT

Wilson Gillespie dreamed of working as a buyer for Neiman Marcus after college, and he beat out 900 other candidates to earn a job with the Dallas-based retail giant. So how did the 2011 Lake Highlands High graduate and Bell Boy end up in Whitefish, Montana hand-making custom furniture and spending every free moment on the ski slopes?

Gillespie went to Texas A&M University with lofty plans to study Adam Smith, John Maynard Keynes and other learned economists. Instead, he found his time there “a total snooze fest, oversaturated with useless graphs and numbers that have no application in the real world.”

Gillespie earned a coveted summer internship at Neiman’s his junior year and worked alongside accomplished students from Harvard, Stanford, Notre Dame and Vanderbilt. He was coming off academic probation and prepping to graduate a semester behind his Aggie classmates. His boss offered him a full-time job and a compliment: she appreciated his “laid back sense of professionalism.”

After graduation, Gillespie started work in the ladies’ shoes buying office overseeing most of the Paris fashion houses. Two weeks later, he was googling ski towns and planning to move.

“I hated sitting at a desk,” he remembers. “I started asking myself, ‘Is this really it? Because if so, I want nothing to do with this.’”

Gillespie needed reconstructive surgery on his torn ACL, so he delayed his departure for the slopes. He continued working for Neiman’s, focusing on physical therapy and squirreling away cash. His therapist, also a graduate of LHHS and Texas A&M, was impressed with his dedication and his progress. When she heard he was headed for the mountains of Colorado or Utah, she told him there’s no place like Whitefish, Montana.

Gillespie took her advice and packed everything he could fit into his two-door soft top Jeep Wrangler. He’d found a furnished room on Craigslist but didn’t have a job or know a soul.

“My 68-year-old landlady, Linda, was a product of the hippie era. She smoked a ton of weed and drank prosecco by the bottle. She went to bed at 5 p.m., so I had the house to myself every day after work. She was going through a divorce, so I doubled as her roommate and in-house therapist.”

Gillespie arrived in October, and his plan was to earn a free ski pass by working the lifts when they opened in December. He took a roofing job in the interim, though he had no construction experience. He was the only person on the crew with a high school diploma.

“I absolutely loved it. It was 70 degrees and sunny every day my first month, and I could just do mindless labor without a care in the world. We primarily worked on luxury custom homes, which meant big and high. My favorite part was running around the roof of a third floor, balancing while carrying stacks of shingles.”

Gillespie’s boss, James, appreciated his work, so he promised a ski pass if he’d keep his construction gig. James pulled a few strings and had an all-access ski pass ready for pick up later that week.

“My philosophy was just to say yes to everything and fully immerse myself in every new experience I could,” Gillespie says. “(During college) I said no to things all the time and stayed in a certain comfort zone. I hated that side of me in retrospect, and I wanted to go all-in on Montana.”

Gillespie says he was “clueless” on the construction site, and his coworkers ribbed him every time he made a mistake. James lived up to his reputation for being a hard driver, and no one believed Gillespie could survive both the wrath of James and roofing in Montana winters.

“I wanted to prove everyone wrong more than anything,” says Gillespie. “I loved the thrill of strapping into a harness at the top of the roof and rappelling myself with one hand while I shoveled snow off the roof with my other. It was some serious cowboy (stuff), and it made me feel alive.”

Gillespie later took a job with a prestigious art gallery while he continued skiing, fishing, biking, snowmobiling and backpacking with the friends he’d made in Whitefish. He now works for Espenson Furniture, an artisan woodworking shop crafting one-of-a-kind items for homes and offices.

“Working with my hands is ideal,” says Gillespie. “My own personal hell is sitting at a desk all day, followed by having my work email on my cell so people can reach me when I’m home.”

Gillespie loves his new environment and says he’s never questioned his decision to relocate.

“The joy of Whitefish is the people. I am convinced that no one works full time or knows what day it is. My roommate once said, ‘Whitefish is where people in their 20s go to retire.’ My friends are the baddest dudes you’ll ever meet and consistently impress me on and off the mountain. Anything I have achieved or accomplished in my time here, I owe to the people around me. I love my friends and what we get to do here. I’m the richest man I know.”