Lisa Barry’s pretty familiar with big events—she’s groomed at some of the biggest.

For many years, Barry picked up extra cash by grooming for friends at three-days like the Rolex Kentucky CCI****, Bromont International (Quebec) and The Dutta Corp. Fair Hill International (Md.). She was working for the O’Connor Event Team when she met Canadian four-star rider Jessica Phoenix in 2007. Phoenix came to train with the O’Connors before the Pan Amerian Games (Brazil), and the two hit it off.

“She’s like my sister now,” said Barry, 29. “We had gone to the Virginia Horse Center for their spring event, and she was talking about the Pan Ams and how she didn’t have any help. On a whim, I was like, ‘If you need help, I’m happy to go with you.’ ”

Barry traveled with Phoenix to most of her international events for several years, including the Alltech FEI World Equestrian Games (Ky.) in 2010. She helped out another Canadian rider, Stephanie Rhoades-Bosch, when she went to the Mitsubishi Motors Badminton Horse Trials CCI**** (England) in 2010 as well.

“I was trained by the best at Karen and David’s, and [Jessica] could trust that the horses were in good hands,” she said. “It was a cool experience to be a part of each part of the sport. To be behind the scenes as a groom as well as being a rider is pretty rewarding.”

But now Barry is on the way to stepping out from behind the scenes into the spotlight herself. She’s aiming for her own first four-star at Rolex. An essential stop on that road is this weekend’s Cloud 11-Gavilan North LLC Carolina International CIC*** (N.C.). And her mount for this quest is a tiny, opinionated sportscar of a horse nicknamed “Peanut.”

Seven years ago, Barry took a huge gamble when she purchased F.I.S. Prince Charming and imported him from New Zealand after just seeing a video. With no luck finding a prospect in Europe, Barry had called up her friend, four-star eventer Donna Smith, who assured her the gray gelding would be a good fit after having taken him around his first few events. 

“It certainly took me a few years to figure him out because he’s quite a difficult horse to ride—pretty hot and sensitive. But he’s such a phenomenal jumper that I kept at it, and he’s become like my best friend,” said Barry. “He’s probably the coolest horse I’ve ever sat on.”

Doing Her Time Learning

Barry grew up near Pittsburgh, Pa., and became a working student for the O’Connors as a teenager after meeting Karen in a clinic when she was 8 years old. 

She competed at the North American Junior and Young Riders Championships in 2002 and 2005 before deciding to make a go at being a professional, all while under the O’Connors’ tutelage.

Barry got her first taste of the advanced level with Kenzo de la Roque, a Selle Francais gelding (Papillon Rouge—Vania De La Roque, Grand Venuer) that she imported as a one-star horse.

They finished eighth in the CCI*** at Jersey Fresh (N.J.) in 2011 and were prepping for Rolex in 2012 when the gelding pulled a suspensory that never quite healed right, so she retired him.

“He was pretty phenomenal and gave me so much confidence at the level and a lot of experience,” said Barry. “He was pretty instrumental in getting my career started at the upper levels. He suffered from a muscle disease called PSSM [Polysaccharide Storgae Myopathy] and when he was competing with me, he literally could not have grass or hay, and his diet was extremely restricted. Otherwise he would tie up really badly.”

Enter Peanut

While Barry was campaigning Kenzo, she was bringing along a spunky Peanut, who turned out to be a lot smaller than Smith had described. The New Zealand Thoroughbred, by His Royal Highness, had raced and brought along some race horse habits, but Barry forged ahead. Peanut was very sensitive to Barry’s balance in the saddle in the beginning, so she took her time and didn’t compete him at all the first year she had him.

“I feel like I’m riding a pony when I’m up there,” she said. “I think he’s probably 15.2, maybe. He’s such a tiny horse that he would overreact to certain things if he felt like he was off balance.

“We worked a lot on keeping things quiet and stretching. It took years before he could start to settle, and once he started to settle we could progress from there. He was so talented that I just stuck with it. All the good ones they say are tough,” Barry said.

Once they found an understanding, the pair moved up the levels with the help of Peanut’s “honest and straightforward” work ethic.

“The thing we’ve struggled with the most is the flatwork,” said Barry. “Once we got the jumping under control, that was easy for him. He really loves it. Now we’re just perfecting those details on the flat and trying to keep him quiet.”

The diminutive gelding tackles every cross-country course with boldness and courage, and his FEI cross-country record with Barry is unblemished.

Watch Barry and Peanut attack the 2014 Jersey Fresh CIC*** (N.J.) course.

“He’s tiny, so at the three-star level it’s like looking up at the big tables, but he attacks it,” she said. “He just loves it out there, and because he’s small, it’s like riding a little Ferrari. Turning is easy, and he’s very straightforward to offsets and narrows and corners. He picks up the line and finds the flags.”

Barry was prepared to go to Rolex a year ago, but a few niggling issues rerouted them to the three-star at the Jaguar Land Rover Bromont CCI*** (Quebec), where they finished second.

“I actually think it was a blessing in disguise because I feel like he’s ready now, and I’m ready in my head,” she said. “It’s something that makes me a little nervous, but I’m very respectful of how difficult it is, and I’m hoping we can have a really good week, but I trust my horse, and I think we’re ready.” 

Barry’s planning on using the Carolina International as a fitness run for Peanut before heading to the CIC*** at The Fork (N.C.) before Rolex.

“Kentucky’s a big deal, so I want to make sure he’s as fit as he can be and nothing better than to run them, so I’m certainly going to go out and be careful with him—not necessarily push for time or anything, but I’ll use the hills and the course to evaluate where he is with his fitness and give him a couple of good, deep breaths,” she said. 

Making Ends Meet

Barry has been out on her own for years after working for the O’Connors, but she still keeps in touch, renting a barn out of their facility in The Plains, Va., in the warmer months and staying at her family’s 5-acre farm in Ocala, Fla., just down the road from them in the winter.

“[Karen’s] been a mentor of mine for so long, and she’s family now,” she said. “She’s known me since I was a child and dealt with all sorts of facets of my life and my growing up and becoming an adult. She’s kind of like a second mom to me. It’s really great to have an incredible eventer and horsewoman as a coach and be that close to me as well. She knows when I need my hand held or when I need my butt kicked.”

Barry’s grooming background has been essential for her, since she takes care of her group of horses mostly on her own. She also picks up the odd photography job to nurture a lifelong passion.

She was the O’Connors’ official photographer when she was based with them and still enjoys taking photos at weddings and for equestrian magazines when she can.

When she’s not riding, Barry fills some evenings by stuffing envelopes to help her parent’s advertising agency fulfill direct mailings and to supplement her income.

“A couple of summers ago I was a little under the weather and needed to get off my feet. I couldn’t ride as much and stand teaching to make money , so my dad came up with this idea that I could do mail fulfillment for his clients,” she said. “The clients had been paying major mailhouses to do mail fulfillment, and it was basically an exorbitant amount of money.

“It’s sort of a mind-numbing thing, but I can do it at night and sit and watch a movie,” she continued. “Last week my mom and I did 10,000 pieces, which is a little insane—the most we’ve ever done. On a daily basis, I have about 50-200 pieces, which is pretty simple to get through. It’s become a bit bigger than I think we anticipated, but it’s become a good way to supplement some income, especially when the season is slow. We do this as a family—I don’t have any owners right now. It’s helpful to have a bit of a back-up for vet bills and entries and stuff like that.” 

Barry also fulfills her passion for breeding by bringing along her family’s homebreds, all out of their foundation mare, Rajacon’s Rose (Consul—Raja’s Lucky Lady, Northern Raja), a Dutch Warmblood-Thoroughbred.

She starts the young horses and sells some. She’s currently campaigning Rosie’s Little Miss Liberty, an 8-year-old mare by Consul, at the two-star level.

“She was awesome from the first day I got on her,” she said. “She’s always had a little bit of a hump in her back—she threatens to buck but doesn’t actually go through with it. I’m the only person to have really ridden her. I’ve put all the work into her, so to take a thought in our head about having a baby and picking a stallion, up to the two-star level is absolutely incredible. It’s so rewarding to me to be able to have that kind of relationship with her, knowing that it really came from the beginning.”