Featured Pro: Diana Conlon of Olive Hill Sporthorses

Diana Conlon of Olive Hill Sporthorses in Lexington, Kentucky started riding horses before she could walk. Her lifelong commitment and focus on equestrian sports transformed into a viable profession. Today, she owns and operates Olive Hill Sporthorses, a premier sales and training program in Lexington.

Diana Conlon and PDR Pinion. Photo: Shawn McMillen.

Her horses and riders show at everything from local to rated shows in Kentucky, the surrounding areas, and across the country. Diana also serves on the Kentucky Hunter Jumper Association (KHJA) board of directors, as well as giving back to the sport in various other ways.

She was surrounded by equestrian experiences growing up in the Bluegrass state and spent much of her youth showing locally. Her parents insisted on college, so she chose an animal science degree at the University of Kentucky. While there, she started riding on their equestrian team and had many opportunities to show.

Diana was also introduced to the business side of equestrian sports as a working student while at the University of Kentucky, and this opened the field up for her to become a professional trainer. “After I graduated, as far as I was concerned, I had no other option except to ride horses,” she says.

Going Pro

The singular focus on riding horses helped Diana become a well-respected competitor and trainer. Her active pursuit of learning experiences developed her into a well-rounded professional. Diana credits watching people at the top of the sport, and the different perspectives she gained by working for different people.

“I never wanted to pursue anything else; all I wanted to do was ride,” she adds. “My focus has always been on the horses. In college, I worked for different people too, it all happened naturally. Step by step, I made my way into being a professional.”

After graduation, Diana was working for a private farm in Lexington. “My first job was with a guy that managed shows, and he also bred and showed Quarter Horses, and that was a huge education in horsemanship,” Diana says. “After that, I started working at a private farm that focused on A-circuit hunters and took my first trip to Europe to ride and buy horses. I value all people for different reasons, everyone you surround yourself with has a different impact on your life.”

When a local hunter/jumper trainer that Diana worked with decided to re-locate, she was given the opportunity to move into her facility and was able to start her own business – Olive Hill Sporthorses.

The horses also impact riders and professionals, just as the experiences working with different professionals and parts of the industry did. Diana has been fortunate to ride and train many top jumpers along the way. Wondergirl was the first horse she bought for herself and went on to compete in national Grand Prix events with. Since then, many special horses have come through the doors at Olive Hill

Olive Hill Sporthorses

Diana slowly built upon the existing business, and it continued evolving. She bought the property on the north side of Lexington in 2017, had a barn and indoor built, and moved in on Labor Day of 2017. Olive Hill Sporthorses is conveniently located only 10 minutes from the Kentucky Horse Park. There are two barns at the end of the tree lined driveway with 34 stalls total, large indoor and outdoor rings, ample turnout, and amenities such as a heated viewing room, tack rooms, and multiple wash stalls.

The outdoor arena at Olive Hill Sporthorses. Photo courtesy of Diana Conlon.

Today, Olive Hill Sporthorses has showing clients, sales, and training horses instead of the large lesson program she started with. “I like the path the business is on,” Diana reflects. “Of course, you always want better horses, more competitive and higher-level horses, more sale and training horses, and I also want the people riding with me to be highly competitive riders.” She’s steadily accomplishing all those goals.

The barn at Olive Hill Sporthorses in the morning. Photo courtesy of Diana Conlon.

Being an equestrian professional comes with challenges and rewards, but Diana takes it all in stride. Training is an easy and natural thing for her, and Diana adds that Olive Hill Sporthorses has a great group of clients and horses.

Hacking out at Olive Hill Sporthorses. Photo courtesy of Diana Conlon.

Any challenges are easily offset by the rewards of training horses and riders. Diana enjoys seeing their progress. “I love working with young horses, developing, and selling them. Being able to figure out horses’ personalities and figuring out the right training program for them is also rewarding.”

For example, PDR Pinion, bred and owned by Palmer Divide Ranch in Colorado, is quirky and had a hard time fitting in at previous barns. Diana figured him out and they get along well. He was jumping 1.00m when he arrived at Olive Hill Sporthorses and now is a Grand Prix horse. Figuring out how to make him successful was a rewarding process for her. Wondergirl is also still in the barn, now owned by one of Diana’s clients, but before she sold Wondergirl, the pair competed in national grand prix events.

Working in the indoor arena. Photo courtesy of Diana Conlon.

Training horses professionally is a marathon, not a sprint. Diana encourages other trainers to take breaks and time for themselves. Equestrians can easily work 24/7. But taking a day or afternoon off helps the mental game and allows you to be 100% when you are at the barn. On the riding side, Diana notes that it’s important to have people on the ground helping and to bounce ideas off of.

Olive Hill Sporthorses riders congratulate each other on a good round. Photo courtesy of Diana Conlon.

Her parting advice to riders is, “It’s okay to make mistakes. A lot of riders want everything to be perfect, it’s not. Make mistakes, learn from them, and realize that making progress isn’t a linear track. Don’t focus on the perfect distance or position. The goal is to get better but if you are too focused on being perfect it’s hard to make that progress.”

To see the current horses that Olive Hill Sporthorses has listed for sale be sure to visit her ProEquest profile!