Name: Cassandra Armento-O’Neill
Age: 50
Hometown: Loxahatchee, Florida
Occupation: Lawyer and coffee shop owner

Though she grew up riding hunters and jumpers, it was a trip to a Morgan show that changed Cassandra Armento-O’Neill’s life.

After graduating from Skidmore College (New York) with a double major in English literature and political science and before heading to law school, Armento-O’Neill worked briefly as an advertising account executive for the Northeast Equine Journal. She attended the Morgan show to present an award on behalf of the magazine, and there she met Dan Burgess, who was running a coffee cart at the show.

She and Burgess started dating, and she quickly became immersed in the coffee world. While at law school, she helped expand his business, Burgess & Clark Coffee Company, from the mobile cart and one shop in Manchester, New Hampshire, to five cafés and the mobile cart, which she started taking to bigger horse shows throughout New England.

“We had the retail stores, the coffee business going to horse shows, and I was in law school, all at the same time,” said Armento-O’Neill, who had sold her amateur-owner hunter and stopped showing herself before starting law school.

Now Armento-O’Neill is a busy amateur who travels the hunter/jumper circuit as both a competitor and the owner-operator of a popular coffee stand—who somehow finds time to practice law on the side.

Cassandra Armento-O’Neill brings her Anonymous Coffee shop to shows across the East Coast, including the Hampton Classic (New York). Photo Courtesy Of Cassandra Armento-O’Neill

She missed the experience of being astride a horse, so the day after she passed the Massachusetts bar exam, she had a horse on trial at the Vermont Summer Festival.

And even after she and Burgess parted ways, she continued to expand the coffee cart business.

When she became engaged to her husband Patrick O’Neill years later, she changed the name of the company to Anonymous Coffee, dismissing her friends’ suggestions that she call it “Cassandra’s Coffee,” saying, “I’m not that person. I like to keep to myself. I want to be anonymous.”

Anonymous Coffee has become a mainstay at shows like the Winter Equestrian Festival (Florida). Armento-O’Neill got her start there at the nearby Littlewood showgrounds in 1997, talking her way into the big show by the end of the circuit. Now she spends from August to April in Wellington, serving customers at the Palm Beach International Equestrian Center.

She and her team caravan to other major shows on the East Coast circuit, setting up their carts at venues including Lake Placid, the Hampton Classic (New York), the Pennsylvania National, Capital Challenge (Maryland) and the Great Lakes Equestrian Festival (Michigan).

Armento-O’Neill schedules showing her adult jumper Balounist JSF (Balou Du Rouet—Balla’Laika JSF) around her coffee job, and these days she only competes in Wellington and Traverse City, Michigan.

“The coffee company does take up a lot of time and effort and energy,” she continued. “It can be very difficult to put on the show hat and go straight to the ring. … I’m very competitive and want to focus on my riding and showing, but it’s also very important to me that the coffee business maintains its quality and service. When I am showing at the same show that I’m serving coffee at, I make sure that I have enough help, get enough sleep and have proper training care for the horse.”

She faces a challenge familiar to many amateurs: A busy work schedule means there’s not much time to get in the ring.

“The first time I showed at WEF [this year], I hadn’t shown since I was at Traverse City [Michigan],” Armento-O’Neill said. “The first time back in the show ring after seven-plus months is really hard. I struggled with that, and we had problems the first couple times. I’m super rusty, the horse is really spooky; I walk into a 1.10-meter class like I own it, and I don’t own it at all.”

Despite the rusty start, Armento-O’Neill hit her stride within a month or two, winning a low adult amateur jumper class with “Luca” during the Equestrian Sport Productions Spring I (Florida) under the guidance of trainer Blair Willmer.

“I took a year to find that one, and I’d fallen in love with the Balou du Rouet line,” she said. “He looks like a draft horse, but he’s quite bloody and very spooky and animated. He’s very funny. This horse is the reason we fall in love with horses.”

Cassandra Armento-O’Neill competes Balounist JSF in the adult jumper division when she’s not running Anonymous Coffee or working as a lawyer. Anne Gittins Photo

A Day In The Life

When she’s working in Wellington, Armento-O’Neill stays busy.

She rises before dawn to feed her horses, then heads to the show grounds to open the coffee shop. It opens at 6 a.m., but she or another employee has to be there by 5:30. She works until about 10:30 a.m. then heads home to ride her horses before returning to the coffee shop. After they close up at 5 p.m., she’ll go shopping for the next day’s coffee shop supplies, then come home, take care of the horses, make dinner, and, finally, bake muffins and other pastries for three hours. Armento-O’Neill supplies all the baked goods for the shop.

When WEF shut down a week early in 2020 thanks to COVID-19, Armento-O’Neill stayed open with permission from management.

“The grooms and the people that are stuck here are going to need their banana, their muffins, their coffee,” she said. “Even if there were only 50 people on the show grounds, we needed to take care of them. When push comes to shove, people in this sport are going to have each other’s backs.”

Outside of WEF—where she takes a 12-week break from lawyering—Armento-O’Neill works on about six legal projects a year. She is a member of the Massachusetts and Vermont bar associations.

“I’m not doing litigation and trial work,” she said. “If someone called me and said, ‘I need to form a syndicate,’ I’d say, ‘When do you need it?’ I’ve done a little arbitration, which is kind of fun. I like the creative side of it, like finding venture capital for people. I’m an entrepreneur at heart.”

“This horse is the reason we fall in love with horses,” said Cassandra Armento O’Neill of Balounist JSF. Photo Courtesy Of Cassandra Armento-O’Neill

Why She Does It

There’s no question what the busiest day of the year is for Armento-O’Neill: The day of the Dover Saddlery/USEF Dover Hunt Seat Medal Finals at the Pennsylvania National.

On that day, Armento-O’Neill opens around 4:30 a.m. ready to serve a never-ending line of bleary-eyed riders, parents, grooms, staff and trainers.

While she’s worked the show since 2007, there is one year that sticks out: In 2016, a West Coast trainer came to the back of Armento-O’Neill’s trailer when she had a huge queue of customers needing caffeine. She internally rolled her eyes, thinking this woman was trying to cut the line, but instead the trainer handed Armento-O’Neill a $100 bill. The trainer told Armento-O’Neill that she knew what a tough day it was for the coffee team, but that their efforts were appreciated and that she wanted to cover drinks for anyone who didn’t have cash.

Thanks to that trainer, Armento-O’Neill was able to buy drinks for people throughout the week, including a group of teenagers who sang the national anthem before the grand prix class. Armento-O’Neill, a former singer herself, was thrilled to be able to treat them to milkshakes after their performance.

“That is why I do this,” she said. “I feel like my stupid little business has really carved itself out as a place that everyone knows and likes and feels respected. It is a little component of this world, but it is all I can do.

“This business has allowed me to get on a first name basis with many superstar riders. I regularly serve idols like Laura Kraut, Shane Sweetnam, Paul O’Shea, Rodrigo Pessoa, Anne Kursinski and the like. The take-away is that the horse industry is one place where it all coexists together for the good of the sport and the well-being of the animals. I feel fortunate to have a small role in it.”

Do you know an amateur with a cool story? Email Lindsay Berreth at lberreth@coth.com for a chance to be featured.