Story by Kaitlin Hill
Photo by Phelps Group

With a banner show jumping career and successful training programs in Wellington, Florida, and her hometown, New Albany, Ohio, Ali Wolff has certainly made the most of her quarter-century on horseback. And she shows no signs of slowing down.

The young rider, who will turn 30 in July, has represented the United States in competitions worldwide with her string of mounts, racking up impressive prizes along the way.

In June 2018, Wolff and her longtime partner, Casall, won the Upperville Jumper Classic CSI4*, her first international grand prix victory and a professional high point. As a trainer, Wolff’s wins take shape in the accomplishments of her students and in the top-tier care of their horses. Wolff reveals the challenges and triumphs of her career and her plans for the future in the following Q&A with Middleburg Life.

ML: You started riding at such a young age. How did you get your start?

AW: It’s funny, our family laughs in confusion about how I even decided to start riding because no one in my family really rode, especially not competitively. I guess I have to give credit to the local fairs and zoos because I would always beg my parents to go on the pony rides.

What has been the most challenging part of transitioning from amateur to professional?

I think the most challenging part was getting people to accept me as a professional and transitioning out of the amateur stereotype. Typically, amateurs buy their own horses without the interest of selling them again for profit, but to keep them and compete on. So it was hard to break that mold and convince people this was now my business instead of my hobby.

What is your favorite part of competing?

I am competitive by nature so I like to compete in anything and everything. But my favorite part might be the thrill, that adrenaline rush you get before going into the ring. It’s a mix of nerves, excitement and anxiety, and the feeling after when you know you have put in a good round, the satisfaction that everything you have done leading up to now was worth it.

Tell me a little bit about your facility in Wellington.

It’s actually a really exciting time for us in Wellington now as we have just sold our house and farm, and have bought a new piece of property to build a barn on. We will build a 20-stall barn with a decent outdoor ring and about 10 paddocks. Of course, we are hoping to be done before the start of Winter Equestrian Festival (WEF), but you never know when building in Wellington.

What is your favorite part of being a trainer?

I used to think I got relatively nervous before entering the ring to compete, but being a trainer and sending your student in is a whole new level of nerves! My favorite part about being a trainer is the excitement of seeing your student be successful in the ring and come out with a big smile.

What would you consider your greatest career success?

At first, I was inclined to write down successful classes or accolades I have won, but if I really think about it, I find my greatest success to be the ability to connect with a horse and form a successful partnership. I am not the greatest catch rider, but I think my strengths lie with the ability to take a horse, put it into our management program, work with it, and transform it into a top show jumper.

\What would you say to other young women interested in taking up the sport?

The best part about this sport in the United States is that it is dominated by women at the lower levels. The higher you climb, the fewer women there are competing at the top level. I consider this an exciting challenge, and I would hope that type of challenge would entice others with the same passion for this sport!

When you’re not riding, training, or running your business – what do you enjoy doing most?

I love being home with my family and doing family activities. I also love to go on adventures with my boyfriend, Ed, who is also my business partner, whenever we can find time to get away from the horses and do normal things.

What are your plans for the future? One year? Five years? Ten years?

I am still learning how to balance my business between training and riding, but for my future riding plans, I would like to keep striving to make the Top 30 riders in the world, and to remain an active member of team events. As a trainer I would like to continue training clients that have a serious passion for this sport, and who strive to be better every day.

This article first appeared in the May 2019 issue of Middleburg Life.