Continuing a Legacy
Cailin first learned about starting colts from her grandfather, who preferred buying horses that hadn't been handled or raising his own.
Cailin’s foundation in horsemanship was shaped by her late grandfather, Bill Dew—an innovative, no-nonsense horseman from Tennessee known for his honesty, knowledge, and high standards. He taught by example, urging her to trust her own judgment and respond to the horse in front of her, not a prescribed method. "Do what the horse needs," he’d say, "... not what a book tells you."
Though Bill had a passion for showing Tennessee Walking Horses, his support for Cailin grew when she became drawn to the American Quarter Horse and the western disciplines. Even though the style of riding had changed, Bill never abandoned his hands-on, adaptive style of horsemanship and encouraged Cailin to do the same. His sureness made him seem stubborn, but it wasn't until adulthood that Cailin could recall how flexible he truly was.
"Grandpa kept a barn full of 16-plus-hand Tennessee Walkers. When I was a child, they were too big for me to saddle and mount on my own. I wasn't a child who asked for things, but I REALLY wanted a pony so I could have some independence. It wasn't too long before Grandpa came home from a sale with a stock trailer full of ponies. We spent countless hours working those little guys together. A lot of them had to be restarted, they were pretty ornery. I got to pick one out for myself, and the rest would be improved upon and sold. He really expected me to work diligently with them. As I got a little taller we bought quarter horses and paints and learned about western show horses together."
After Bill suffered a life-altering stroke in 2012, Cailin joined her grandmother Beverly and her parents, James and Tammy, to keep the family horse farm, Glen Oaks Equestrian Center (Glen Carbon, IL) running and his legacy alive and is now joined by her husband, Tim who has a knack for quiet stockmanship. The influence of her loving and resilient family continues to guide her work today, driving a style of horsemanship rooted in observation, adaptability, and accountability.
Challenging Breed and Discipline Norms
Cailin riding a 3-year old warmblood filly in her first 30 days under saddle in preparation for a career as a show jumping horse.
Cailin’s professional career began in a Thoroughbred colt-starting program that challenged convention. Despite the breed’s reputation for being “hot,” the operation consistently produced calm, confident colts—prepared not only for the racetrack, but for life beyond it.
"We started those thoroughbreds like any good riding horse: gentle, thoughtful, and willing. They learned to lead with quality, gallop, and break from the gate without losing their patience—They ran only when asked which really pleases exercise riders who are accustomed to bothered colts who get scared easily and might even run off."
That experience fundamentally reshaped Cailin’s standards for horsemanship across breeds and disciplines. Like grandpa said, "A horse is a horse".The environment also opened doors to opportunities with sports medicine veterinarians working on Thoroughbred and Standardbred racehorses, western performance horses, and more. While she has a special love for cow horses . she continues to work with many breeds and starts colts in preparation for a variety of disciplines.
Lessons from Mentors Beyond Horsemanship
Cailin and dear friend/mentor, Barbra Schulte, at Art of the Cowgirl in Wickenburg, Arizona. Art of the Cowgirl is a foundation and expo that promotes mentorship amongst women in the western arts.
Drawn back to the show ring in cow horse competition, Cailin returned to western performance with a clear goal: pursue excellence without sacrificing partnership. With few local resources, she sought mentors who proved that top-level results come from trust, patience, and respect for the horse.
"My mentors have something very special in common - They work just as hard on their own personal growth as they do on their horsemanship. Their example convinces me that true mastery is as much about character as skill. As Grandpa, my first mentor would say 'I know you love horses, but there is much more to life than horses'."
Those lessons shaped a simple philosophy: Work on yourself, practice on the horse.
" I am so grateful that my life with horses has brought the most authentic, generous, and talented people into my life who continue to set an example for what self-discovery and a life well lived can look like."
Success, in her approach, is measured not only by results but by the process of getting together with the horse. Every step forward is a step taken together.
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Lauren Brooks, Client
"The honesty, passion, and authenticity Cailin brings to her training are truly special. Working with her has been a game-changer, and I hope others get the opportunity to experience her approach and dedication the way I have."
Chris Brazzle, Client
"Cailin is a calm and confident young woman with a passion for helping the horse and its human understand how to effectively connect and communicate with each other. "
Wendy Thibodeaux, Client
"The reason I chose Cailin Messer to be our trainer is her calm but direct techniques. The changes in my horse and I are directly related to Cailin's skills as a trainer and being the right trainer for the two of us."