Sep 18, 2008

Rider Profile - Jonathan Holling

Meet Jonathan Holling. He’s a trainer based in Ocala, Fl. Jonathan, along with his wife Jennifer, runs Willow Run Eventing, a beautiful facility with multiple barns, an indoor arena, and a rolling cross country course. “Thank God for Jenn. Anyone who knows us will tell you that the business wouldn’t run without her”, says Jon.

(Above: Jon with wife Jenn and young son Caiden.)

Jonathon started riding when he was a toddler. He would ride his pony all over town, while his mom ponied them with a lunge line. As he got older, he started riding more seriously. He started showing, and was pretty good. Although Jon participated in many sports, riding was the one he enjoyed the most, and was the most competitive at. According to Jon, who is very competitive by nature, that was the reason he stuck with riding; he hated to lose, and he was only average at all the other sports.

When Jonathon was in his senior year of high school, it started to become obvious that he wanted his life to evolve around horses. He just wasn’t sure what exactly he would do. He thought about being a blacksmith, and even did it for a summer. He opted out of going to college, and instead got his first advanced horse. Soon after, Jon got the opportunity to be a working student for Peter Gray. He worked for Peter for two years, and then rode under Peter for another year. Even after starting his own business in Wisconsin, Jon still wasn’t sure where his riding career was headed. Although he wanted to ride and teach, he didn’t know then what level he would come to be at today. Jon said that thanks to all the support he receives from his coaches, his parents, and especially his wife, he’s finally getting a good start on his career, both in training and competing. When asked if he was living his dream, there was no question about it. “100% yes. It is my nature to always want to be more successful, but I am absolutely living the dream.”

(Jon & Lion King – aka “Simba”. Josh Walker photo.)

As far as who’s made a difference in his riding, and in his life, Jon has a long list. His parents made the biggest contribution by supplying him with the one thing that every rider needs to be successful: the horses. When Jon showed his parents that he was serious about making eventing his living, his parents bought him his first advanced horse. Ever since then, they’ve owned horses in Jon’s barn, including Tell You Why. Tell You Why was one of Jon’s early Rolex mounts. Currently, they own Downtown Harrison, an amazing four year old that Jon hopes will be well known in a few years. Of course, providing Jon with horses only came second to the faith and support his parents showed him. “When I did not make the Pan Am team in 2007 I was very upset. My Dad’s first words to me were not sorry but instead he told me how proud he was of me and that I was the only Holling to ever make it so close to represent our country at a major international championship.”

After Jon’s wonderful parents comes his wife, Jenn. She keeps Jon grounded, but she also encourages, and she knows exactly when to do both. Jon said that he can’t even begin to list all the wonderful things about his wife.

Next are his coaches. Jon has ridden with many trainers over the years. Anne Jennings was his first coach, and gave Jon much of his basic training and horsemanship. Already mentioned was Peter Gray, who still influences the way that Jon rides, and they way he runs his farm. Jon was also taught by Jimmy Wofford for several years, and he tries to use as much of that knowledge as he can. Jon is now riding with David O’Connor, where’s he’s been riding for the past three years. Jon said that he’s really benefited from David’s guidance. “David and Karen are such great horsemen that it’s hard not to learn just by being around them.”

I also asked Jon the same question regarding his horses: How did they help, and what did they teach him? His answer was typical for a true horseman; he’s learned something from every horse he’s ever sat on. Jon’s first event horse, Guinness, hated ditches and water, and was tough to get around a cross country course. Jon doubts he would make Guinness do the same job today, but he did learn a lot from the difficult horse. He learned how to be strong, but still supportive of his horse. Jon also mentioned that Tell You Why was a great horse, the epitome of a good boy. He taught Jon that heart is the most thing an event horse can have. Lion King, or Simba around the barn, is one of Jon’s current upper level horses, and has given Jon most of his international experience. Jon calls him Captain Consistent. He says that Simba’s made him a better rider at every phase, just by giving him miles at the upper levels, not to mention being pretty competitive, too. Direct Merger taught Jon the most, in the least amount of time. He taught Jon that he could take a difficult horse, and still be competitive on him. “All it takes is faith and patience. Unfortunately the biggest lesson he taught me is that life is not fair and that even when things are going horribly I am capable of picking myself up and continuing on.”

(Jon & Direct Merger. Josh Walker Photo.)

Speaking of Lion King, we’ve all been wondering what his absence means. Well, Jon said that Simba’s doing great. He was scheduled for Rolex back in April, but ended up catching an odd virus a couple weeks before the event. He took a while to get completely over it, and as a result missed the entire spring three day season. However, he’s now back in work, and aiming for Fair Hill in the fall.

With this year’s Olympics still fresh in everyone’s minds, I couldn’t help but be curious. I asked Jon if, with this year’s Games behind us, he’ll want to try for a spot on the team next time in London. Jon is looking forward to both the World Championships in 2010 and the Olympics in 2012. “I am currently restocking my barn with some exciting new horses for both competitions.” I can’t wait to see who he produces in the next couple of years. Downtown Harrison, perhaps? But, as we all know, the life of an upper level rider isn’t all championships and international competitions. At Jon’s very first US training session with George Morris, Jon was riding Simba. Other team members in the lesson were Darren Chiacchia, and Karen and David O’Connor. “Let’s just say I was not the star that day. It was very humbling, but I have to say the next day went much better.” Hearing that Jon was humbled by George Morris makes me feel so much better about failing to show my dressage coach a proper leg yield!


(Right: Jon & Simba)

I asked Jon if he had any advice for up and coming eventers. I really liked his answer. He said that the first thing you have to do is to ask yourself if you really want to do this. “That may sound like a simple question to answer, but you might be surprised. Put yourself in a good (not easy) working student program for at least two years. Approach it like school. If you drop out, it’s not for you. That’s nothing to be ashamed of, but if you can’t hack a couple years slogging around as a working student, you are not cut out for this world. If you make it, congrats. Now the tough part starts. Be determined and you will eventually succeed. If you’re no good at the books, marry up like I did and get a smart husband or wife!” Amen, Jon!

While we were on the subject of up and comers, I asked how life as a new dad was treating him. Jon said that being a dad in the single greatest thing he has ever done. He said that everything people told him about parenthood is true; except the good stuff is so much better than they told him, and the bad stuff isn’t so bad – yet. He hopes that Caiden will want to ride, at least enough that the whole family can enjoy their life at the barn together, although the thought of watching him play sports sounds fun too. Jon said “I only hope he has the drive to be successful in life, whatever that means to him.” What’s Jon’s favorite part of the life he leads? “There are so many great things in my life; right now it is the ability to spend most days with my wife and son.”


So there he is, Jonathon Holling. Trainer, instructor, husband, dad. He leads a busy life, but it’s a rewarding one. The life of an eventer isn’t always easy, but Jon has showed us that if you have the heart, courage, and the support of people who love you, we can push on. We should all be so lucky; to be surrounded by family, friends, and the horses we love.

Dec 20, 2024 Sponsor

“Happy Horse Equals Happy Judge”: Ask An Expert with Dressage Judge Peter Gray, Brought to You by Ride iQ

Ride iQ’s popular “Ask An Expert” series features professional advice and tips from all areas of the horse industry. One of the most-downloaded episodes is an expert session with Peter Gray, an accomplished dressage judge and Olympic eventer. He has recently judged at events like the five-star at the Defender Kentucky Three-Day Event, and he served on the ground jury at the 2022 FEI World Eventing Championships in Pratoni, Italy. His background as a competitor in the Olympic Games riding for Bermuda and as a coach and selector for the Canadian eventing team adds depth to his understanding of the sport.

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Dec 18, 2024 Association News

USEA Office Closed for Holidays

The USEA office will close at 5:00 p.m. EST on Friday, Dec. 20, 2024, and will reopen again on Thursday, Jan. 2, 2025. The USEA staff will return emails and phone calls when the office re-opens on Thursday, Jan. 2, 2025 or at their earliest convenience.

Dec 18, 2024 Interscholastic

Start Planning for the 2025 USEA Intercollegiate & Interscholastic Eventing Championships at Stable View

After the success of the first annual USEA Intercollegiate & Interscholastic Eventing Championships at Stable View in Aiken, South Carolina, members are not going to want to miss the second edition in 2025! Barry and Cyndy Olliff, owners of Stable View, and their team are gearing up for an even bigger and better event in the coming year. If you are a current or prospective member of the Intercollegiate Eventing Program or the Interscholastic Eventing League, be sure to block off the weekend of May 3-4, 2025 to attend these exciting Championships.

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