By Laura Scaletti
Portraits by Kacy Brown
Kacy Brown Photography
They say what happens in Vegas stays in Vegas. For Jenny Cunningham, a 2012 trip from Ireland to Vegas for her 21st birthday was just the beginning of her American story.
It was during that trip that Jenny met Zach, her now-husband. “I was finishing college and had no real plans on what I wanted to do in life. When I met Zach and he lived in Florida, I said, ‘Why don’t I come to Florida for the summer and see what happens?’” Jenny said. “I did that and never went back home to Ireland! About four months into living in Florida, I shipped over my horse, George, and started getting into the horse world in the States.”
Moving from her small town of Mullingar, Ireland, to Orlando, Florida, was definitely a culture shock for Jenny. “The cost difference and just the overall management of horses and clients was a huge shock to me. But I quickly adjusted and made lots of friends here,” she said.
A show jumper since her earliest days, Jenny decided to make another life change in 2019 and began pursuing dressage full time. Aboard her trusty High Adult Amateur jumper, Bingo, who also had zero dressage experience, Jenny entered the dressage arena. “I trained Bingo up to competing at the Prix St. Georges level. This was such a huge accomplishment for me, as it proved you can successfully switch disciplines with the same horse,” Jenny said.
Irish Roots
Growing up in Ireland, it was only a matter of time before Jenny found her way into the saddle. That happened at age 8, thanks to a best friend with a pony. “I thought I would try it, and I was instantly hooked. Having horses in Ireland growing up is something special. Horse riding is just so much more accessible than here in the U.S.,” Jenny said. “Horses are such a huge part of the culture and most people keep their horses at home.”
Once Jenny expressed an interest in horses, her dad went all in. “He has always loved horses and bought a farm down the road from our house. We renovated the stables there and built an arena,” she said.
In her early riding days, Jenny gave it up for a few months. “I got scared the first time my trainer made me canter. Looking back now, it makes me laugh a lot because it’s been my constant obsession ever since I got comfortable with cantering,” she said. “Some of the best times in my life were just galloping through the field and feeling like nothing else mattered.”
After school, Jenny and her best friend would get dropped off at the barn to ride and hang out with their ponies. Regardless of the weather, the girls would spend hours enjoying their ponies and living their best horse-girl lives.
It wasn’t until Jenny moved to the United States that she realized how self-sufficient she was at competitions when she was younger. “I didn’t have a trainer to go to horse shows with; I did everything myself. It’s a bit wild to know as a 13-year-old kid I was left to make my own decisions on pretty big tracks,” Jenny said. “It really made me a better rider, for sure. I had to learn very fast to make quick decisions and how to troubleshoot problems with the horses.”
Jenny had a lot of success in national classes around Ireland and traveled to Scotland and Wales to compete. She always brought home ribbons thanks to her dad providing her with a large string of jumper ponies. “I competed at the highest level with my pony Huntington, who was my dream pony. He took me around courses I wouldn’t even dream of doing now,” Jenny said. “It’s hard to believe these ponies can jump so big.”
Switching Gears
Jenny was a diehard jumper rider until her trainer suggested she give dressage a go. “I took a few lessons, did some research, saw Valegro on a YouTube video and instantly thought, Maybe I could do that. I became obsessed with how horses can move in such amazing ways, while the rider looks like they are hardly doing anything,” she said. “Within a few weeks, I had Bingo dressed up as a dressage horse and we began our dressage journey.”
Jenny immediately fell in love with Bingo, who was initially purchased as a jumper investment horse. “A week or so after he was imported, we were offered a pretty big sum of money for him, but I knew he was something special and wanted to hang on to him. We jumped at all the big events around Florida and had so much fun before deciding to switch rings,” she said.
Jenny admits she misses flying around the jumper ring. “I miss the excitement of potentially winning the class depending on how brave I was willing to go in the jump-off. That rush of adrenaline when you start the course and everything goes silent is so magical,” she said.
At the beginning of their dressage journey, Jenny and Bingo took lessons, but not regularly. “I would take what I learned in the lesson, apply it and practice for weeks before our next one. There was a lot of trial and error at the beginning. I’d watch YouTube videos and then go out and see if I could replicate what I watched on Bingo,” she said.
Used to the jumper life, Bingo tried to jump out of the arena at his first dressage show. “On the way back to the hotel that day we laughed, thinking he’s just not meant to be a dressage horse. The next day my trainer told me Bingo could be a dressage horse. We decided to change his warm-up and he had the most beautiful round at Training level. He got a score of 77%, up from 58% the day before, and won the highest score of the whole weekend,” Jenny said. “That’s when I was determined to reach the highest levels.”
Part of what made the transition to dressage easier is the fact that Bingo is a quick learner. “Once something clicked with him, he got it and didn’t need to relearn it the next day. I never had to drill or push him too hard; he was always game to try something new,” Jenny said.
Jenny and Bingo won nearly all the competitions they entered when they first started trotting down the centerline. “He found the lower-level stuff very easy and enjoyed showing so much that it was honestly just a joy. He is a dream horse in every way and always gives 100,000% each ride,” she said.
Unfortunately, in 2019, Bingo was off for five months because he was not quite right on the right-lead canter. After the vet determined the cause and treatment plan, Jenny decided if she wanted to pursue her goals of getting to the higher levels she’d have to make a change.
The first change was to buy a horse property and bring Bingo home, where he lived for two years. “I wanted full control of what he ate, how long he went out and everything else in-between. It was a game changer,” Jenny said.
The second change was beginning to train with Laura Graves. “At my very first lesson with her, she asked what my big goal was for Bingo. I kind of laughed and said a Prix St. Georges horse. She said he could definitely be a Prix St. Georges horse,” Jenny said. “I left on such a high that day because Laura believed in us.”
Moving Forward
From that first lesson with Laura on, Jenny was determined to make her dressage dreams come true. “Training with Laura really changed my mindset. I used to focus a lot on what we weren’t very good at in the ring, rather than focusing on all the things we were great at,” Jenny said. “She taught me to forget about what others think and just go out there and do what I need to do.”
This partnership has enabled Jenny to flourish. “I think we both work really well together. We talk through any problems, come up with solutions and stay very much on the same page with everything,” Jenny said. “I’m really enjoying the journey of training with her.”
In 2023, Jenny walked into her first Prix St. Georges class aboard Bingo. “Putting on a tailcoat and being on a horse that I fully trained myself was a moment that I will never forget. The week before the show our four-time changes weren’t confirmed at all, but I wanted to give it a go anyway. He exceeded expectation and got all his changes the first time in the show ring,” she said.
The 2025 show season will be the last season before Jenny retires Bingo. “We’ve had so many wins together, and they have always been fun, but to be honest I just love riding him every day. Some of my favorite moments together are during the warm-up days at the shows, because we’re just relaxed and enjoying the atmosphere together,” she said. “I know that may sound cheesy but it’s the truth. I just enjoy doing life together with Bingo.”
As Bingo winds down his show career, Jenny’s journey with her horse Charmie is just beginning. Imported from Germany two years ago, he’s forward and sensitive, which is the complete opposite of laidback Bingo. “He was actually bred to be a show jumper, but is too much of a chicken to jump, so his previous owners switched him to dressage,” she said.
Unlike Bingo, who would walk through fire for Jenny, Charmie requires a bit of hand holding from his rider. “He really relies on the rider for his confidence. It’s been a big challenge for me, but I just continue to give him all the support I can. It took me a while to win him over, but now he neighs at me when he hears my voice,” she said. “He’s a very exciting horse. I’m looking forward to getting out this season and seeing what we can do together as a team!”
Jenny hopes to compete in the Prix St. Georges with Charmie this year, with the goal of competing in a CDI by the end of the year. “Charmie has so much talent and is so willing. I’m taking each day as it comes, but my end goal is to reach the Grand Prix level with him and get on the Irish team,” she said.
Flipping and Fashion
When she’s not at the barn, Jenny can be found working for Zenn Properties, flipping houses. “When I first moved here, Zach said he wanted to flip houses. I didn’t know what I wanted to do at 22, so I said, ‘Let’s give it a go.’ After the first few houses went so well, I was hooked,” Jenny said.
Jenny notes there are a lot of similarities between training horses and flipping houses. “Both can be very unpredictable. The houses I buy are in a very rundown state and every day something will pop up and issues will arise. I’ve made lots of mistakes along the way, but I’ve just learned to accept whatever situation I’m in and come up with a plan to get to the other side of it,” she said.
At the end of the day there is nothing more rewarding than hearing a buyer tell Jenny that they’ve found their dream house. “That definitely makes all the hard work worth it. It’s not always easy, but having my own company has given me the opportunity to ride my horses and do what I love most. For that I’m always grateful,” Jenny said.
Jenny has also combined her passion for beautiful things, fashion and horses on her Instagram account jcdressage_. “It was something that interested me for a while and Zach told me he’d get all the camera equipment and help me make content if it was something I really wanted to do. One day I decided to give it a go and figured if it didn’t take off in a few months, we could sell all the photo equipment,” she said. “It really took off and we’ve kept on going.”
Much like her first days in the dressage world, Jenny started with very limited knowledge about content creation. In fact, she had never edited a photo or video. Now, creating content is a part-time job. “Coming up with ideas is the hardest part. In the evenings I’m writing out ideas and seeing what brands I have to create videos for. Everyone wants big engagement, so I have to prep the night before we go shoot with a full plan of the shots we need,” she said. “I’m extremely lucky Zach is so good behind the camera and is as invested in the quality of the content as I am. There’s no way I could run my account without him!”
When Jenny was starting her account, she decided to reach out to LeMieux to see if they wanted to collaborate on some content. “I didn’t have many followers at the time but had started to post quality photos and videos. I was so shocked when they responded yes and said they wanted to work with me. I couldn’t believe a big brand like that would want to send me items to put in a post,” Jenny said.
Working with equestrian brands and engaging with fellow equestrians makes Jenny smile every day. “It’s been the most fun journey and continues to grow each day. I still have to pinch myself when I see with whom I’ve worked and that they love the content I put out,” Jenny said.
Jenny may wear many hats these days, but she wouldn’t want it any other way. “I’m enjoying flipping houses, making content and training my horses,” she said. “I’m looking forward to continuing all these endeavors. It’s very rewarding.”
For more information, follow Jenny on Instagram @jcdressage_
Photos by Kacy Brown, kacybrownphotography.com
