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Meet Jill Regalado of Wanderlust Pony Services

Today we’d like to introduce you to Jill Regalado.

Hi Jill, thanks for sharing your story with us. To start, maybe you can tell our readers some of your backstory.
I spent the beginning part of my career on the AA hunter jumper circuit. I was primarily working in Wellington, Florida and Lexington, Kentucky, with some of the best national and international riders. Fast forward to 2021, Wanderlust Pony Services launched in Charleston after my first son was born. Wanderlust has evolved over the years, I started just body clipping horses and free lance teaching here and there. Now Wanderlust has a barn family of its own, we have put down roots at Ivy Bridge Stables in Ravenel and we are continuing to grow!

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
I always tell my clients that progress with horses is not ever linear, and I think that parallels most things in life. Growing my business has not been a linear track. I had to take time to create my brand and reputation. Having a barn full of lovely clients does not just show up because one day you decide it should. At the end of 2024, three years after starting my business, I had enough clients to move into a facility of my own. This was going to be it- this is what I always wanted, renting my own farm, things will be done my own way. BUT this moment wasn’t just about me anymore, I have two young boys and a husband who are also supporting this dream of mine. When my year lease was coming up, it was obvious that my work life balance was not where it needed to be and it was time for a change. Now making this decision was hard, it almost felt like giving up on that dream, like a failure. However, what I have learned most about this entrepreneurial journey (and life in general) is that it takes a village. You can’t do it all on your own, even though us perfectionists out there do our darndest. Having the right people around you, believing in the same dream, and also some luck will make the biggest impact on setting yourself up for success. Progress might not look like that idealistic linear track that you originally envisioned, but that does not mean that there is not another, even better opportunity waiting.
I moved to Ivy Bridge Stables with one client. We are now on our way to filling up the barn. It just takes that one leap of faith to spark the right opportunity.

We’ve been impressed with Wanderlust Pony Services, but for folks who might not be as familiar, what can you share with them about what you do and what sets you apart from others?
I specialize in training horses and riders for hunter/jumpers. I am grateful to be based at Ivy Bridge Stables. To train successful horses I think it is imperative for them to be able to be horses too. These horses are not machines we’re working with, so I love for my horses to get as much turn out as possible, have access to proper forage and be able to change up routine whether we are working in the jump ring, out in the grass field, cool down in the covered or do some trot sets out on the bridle path around the farm. This facility really sets up versatile options for a horse to be happy.

We also just hosted our annual Wanderlust Derby Cup! This was a small horse show for our barn family as well as some friends! First was our informal Hunt and Go Derby, with competitors from 3′ to crossrails, then some flat classes, kid leadline and finally our most special class of the day- the Granny Leadline. It was really important to me to create an event that was welcoming for green horses and green riders. Missy Roades was our judge for the day. Missy also left feedback for horse and rider on the scorecard so everyone walked away with more than just a ribbon. This sport can feel exclusive, so making an inclusive and positively constructive event was the priority. We all started doing this because we love horses and the community it creates, so that was really what this event was about. Come join us next year!

Can you talk to us a bit about the role of luck?
I think that the word luck has a dismissive tone to it. Like saying, oh that person just got that opportunity because they were lucky, just by chance happened to be in the right place at right time.
I think that the real luck shows up when you show up for yourself. You take that risk to put yourself out there in that right place at the right time. You do the extra hours, the extra prep, so when that opportunity finally manifests you are ready to show them all you got.
So yes, I am lucky to be in the position I am now with my family, great clients and some lovely horses. I am genuinely grateful that I worked so hard to give myself the chance at this life I have now.
As far as bad luck, that just keeps you humble.

Contact Info:

  • Website: www.wanderlustponyservices@gmail.com
  • Instagram: @wanderlust_pony_services
  • Facebook: wanderlust pony services

Person riding a horse inside an arena, waving, with a child standing nearby, and a white fence in the background.

Four people standing outdoors on grass, with trees and a fence in the background, smiling and posing for a photo.

Child riding a white horse over a jump in an outdoor arena, with trees and a fence in the background.

Person riding a horse over a jump in an outdoor arena, with trees in the background.

Horse and rider jumping over obstacle in an outdoor arena with trees in background.

Two children sit on horses, with two women standing beside them holding the horses' reins, in an indoor riding arena.

Three women stand around a white cart decorated with pink flowers outdoors, with a fence, trees, and a yellow sign in background.

Person riding a horse inside an indoor riding arena, with another person standing nearby holding the horse's reins, and vehicles outside visible through windows.

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