By Amber Heintzberger
Portraits by Maddy Falkowitz
As a young adult, Brett Shear-Heyman spent about 15 years moving around and trying to find out where she fit in the horse world. “It took me a while,” said Brett, now 38, who credits a support system of family, close friends and a few professionals for keeping her best interests at heart.
These mentors kept asking Brett when she would start her own business, but she kept working for other people and trying new 
things. “After I moved back to Virginia in November of 2019 and spent a year working for another professional, in November of 2020 I decided it was time to take a shot at doing my own thing,” Brett said. “I started out on a freelance basis: I had a few clients with private farms and I was riding for a few professionals in the area. Then, I started cultivating private clients. Then, I was very lucky to be introduced to the owners of Dolcetto Farm and I was able to move the business there this past March. I’m very grateful to be at this facility. I’m an old face because I grew up around here and I’ve been in the area for a while, but a new face as an independent professional and business owner.”
The facility is located about three miles from the Upperville show grounds in Virginia, with both indoor and outdoor arenas, and she and her husband live less than 15 minutes away in Middleburg. “It’s quiet and has lots of turnout, and the horses are happy and healthy,” Brett said. “I have a great guy, Victor, who helps me at home and my friend Sue helps on the road. This is a team sport, and having a great team makes all the difference—whether it’s the team that keeps the farm going, the group that helps get you to the ring, the professionals who give you advice or set jumps for you, or the ones you’re out clapping for. You have to build your team, from your vet and farrier to your bookkeeper or marketing girl. I like to spend time making sure my relationships are good, and that I treat people right and play nice in the sandbox! That’s really important to me.”
Penny Leigh LLC
Brett met her husband, whom she describes as non-horsey but very supportive, in St. Louis, Missouri, when she was working at a barn there. They’ve been married four years and together eight and a half years. He works for Mercedes-Benz in the dispatch department and is a former Marine. “He’s done a lot of things and has wonderfully followed me around the country doing this thing that I’m totally enamored with and want to be really good at,” Brett said affectionately.
Brett’s business focuses on teaching, training, lessons and sales for hunter-jumper clientele. She loves to develop young horses and has had some nice investment horses over the years. “We’re a boutique program; I want the horses and clients to get as much attention as necessary,” she said. “I want to keep it small and focused and have the ability to put my hands on the horses every day.”
Recently Brett has developed a circle of professionals that are influential in her life, including Louise Serio, Otis and Robin Brown, Tom and Tracy Brennan, Guy and Tiffany Cambria and Sarah Booker. “They’ve all been varying degrees of support, resource, professional advice, cheerleader and ground crew,” Brett said. “Truly the list of people who support me is much longer, but I think we would run out of print space! They’ve all helped me with the horse I’m developing currently.”
Brett said her business name, Penny Leigh LLC, started as a joke as she used to call her dog, a dachshund, Penny Leigh Long Dog, and when she needed a business name, she came up with Penny Leigh LLC. “My husband looked at me like I was crazy; it started as a joke, but neither of us could come up with anything better,” she said. “So Penny Leigh LLC became the business name. It’s a little bit of a brand. We lost our dog Penny Leigh just this year at age 15, but we have a new puppy, Piper Leigh, so we kept with the PL.”
Margaret Rizzo McKelvy, owner of Mythic Landing Enterprises, LLC, which helps manage Brett’s business and PR, said, “When Brett called to tell me that she was going to start Penny Leigh LLC, I was practically jumping up and down with excitement for her. Brett has been there for me in every moment of building my own business, and I was so happy to return the favor to help her launch her business.”
She added, “Brett is exactly what the horse world needs right now. She’s honest, no-nonsense, and most importantly, she puts the horses first. She remembers what it’s like to be a horse crazy kid just wanting a chance to ride. And she knows that anyone’s competitive success can only come by building a partnership with your horse.”
Discovering her Passion
Though she had a typical suburban American upbringing, Brett was lucky to start riding at age 5 thanks to her mom’s interest in horses. Her mother owned an old, blind dressage horse that she rode with two whips to guide the horse. Brett and her sister took lessons at a nearby riding school, leased ponies and started showing at a low level.
It was around age 14 that she started showing at a few rated hunter shows each summer and discovered her true passion—but it would be a few years before she could completely focus on horses, or compete seriously, because her parents insisted on school taking priority. “We came from an academically motivated family and even when I had been admitted to college, I wasn’t allowed to skip a day of school to horse show, which I appreciate now, but not when I was a kid!” Brett said. “We would do this local series called UpCo Horse Shows and I worked hard to be really good at that. When I was introduced to ‘A’ shows I was in trouble; that was where my heart was.”
Resigned to the student life, Brett was a working student for most of her Junior career. “I was always the one climbing up in the trailer, packing equipment, and I learned to braid when I was young and did that to pay the bills starting around 15 or 16,” she said. “I still braid my own professional horse when the schedule allows, and I’ll braid students’ horses if needed. The braiders called last week and couldn’t make it, so I climbed up and braided a horse for my client.”
Brett grew up in Montgomery County, Maryland, and after graduating from high school she hoped to take a gap year and ride before college. Her mom told her that would be fine, but if she did that, Brett would have to pay for college herself—so off to college she went, settling on American University in Washington, D.C. so that she could continue to ride. She buckled down and got a degree in print journalism after three and a half years, then focused on becoming a professional.
“My parents were supportive and said if I could keep gas in my car, food in my mouth and a roof over my head, I could give it a shot,” she said. “Every time I made a job change, they’d ask if I wanted to do something different, but I just kept going. You just have to keep showing up; you have to keep putting on the costume and walking in the ring and showing up. Of course, everybody wants to have fancy horses and wealthy backers, but you also have to pay your dues. So I just keep showing up.”
Finding Her Way in the Horse World
At age 23, Brett spent three months in France. “I had the opportunity to go abroad, but I was a little bit of a chicken,” she said. “I knew if I went to Europe, I’d have to step up my game and be a little braver. When you don’t have the language skills to ask them to put a placing rail out, you just deal with it! I speak no French, so I had dictionaries everywhere and my motto was, ‘Over, under, through.’ They gave me a bunch of young horses to teach to jump courses, I got the job done and then I came home.”
Today, Brett pays it forward by sharing her experiences with her students and employees. Sue Jarboe, traveling groom with Penny Leigh LLC, said, “Being able to work with Brett has been an invaluable experience. Brett’s dedication to the horses, her clients, her staff and the sport as a whole is inspiring—she truly embodies horsemanship at its best. The experiences I’ve had over the past year have been exciting and educational, and I will carry them with me wherever my life with horses takes me.”
In addition to basing at her farm in Virginia, Brett’s business heads south to Ocala in the winter to compete at the World Equestrian Center. Her business caters to a range of clients, currently including a group of Juniors and adult amateurs. Last year, she was trainer to the Zone 3 Children’s Hunter 14 & Under Champion and the WIHS Regional Hunter Grand Champion, as well 
as being awarded the Professional Sportsmanship Award at the Maryland Horse & Pony Show.
Brett’s career has been shaped around working with horses who were “a little different.” She was once told she rides the “hard ones” better than she does the “easy ones,” but she loves having a small business with the time and space to honor each individual horse. “I’d love to be jumping a Grand Prix or taking a horse to Derby Finals by the time I’m 40, but I’ve learned those kinds of targets can be disheartening,” she said. “Life is going to offer you certain things and you have to do the best you can with what you have. I called myself the ‘Island of Misfit Toys’ at one point because I had horses that were quirky or impatient and I’d do the best I could to make them happy and set them up doing jobs that they’re suited for. I spent my time giving them the tools to be successful, and the same for my clients.”
For more information, visit pennyleighllc.com and follow on Instagram @pennyleighllc
Photos by Maddy Falkowitz, maddyfalkowitz.com and on Instagram @msf.photographyy
