In this installment of our Equestrian Entrepreneur series, we are spotlighting Geoffrey Hesslink, a horseman and trainer behind Hesslink • Williams, based in Wellington, Florida. Geoffrey has built a program rooted in thoughtful horsemanship, clear communication, and a deeply hands-on approach to both horse care and rider development across the Hunters, Equitation, and Jumper rings.
Geoffrey’s story is one of taking early risks, learning through experience, and building a program shaped by intention, care, and a deep respect for both horses and riders. His path reflects a thoughtful approach to horsemanship and business, grounded in the values that continue to guide Hesslink • Williams today.
To start, please introduce yourself and tell readers a little about your business. Where are you located and what do you specialize in?
Hi! My name is Geoffrey Hesslink. I was born and raised in Shelburne, Vermont, and I operate my business, Hesslink • Williams, out of Wellington. We prioritize the care, management, and training of students and their horses in the Hunters, Equitation, and Jumper rings.
How did you get started in the horse industry and what led you to launch Hesslink • Williams?
I began riding horses at the age of 9. I do not come from a horse-oriented family at all, so it was all very foreign to me and my family. I grew up playing a number of sports, all of which I took very seriously, but none of which I truly loved, until I got on a horse for the first time. I was and still am an avid animal lover, and the rush and love I have for working with horses is what gives me purpose.
I grew up riding and showing competitively in the Hunters and Equitation all over the country. I knew this is what I wanted to do in my life, but since I was young and came from a middle-class family, being successful at the top of the sport felt unattainable.
When I aged out of my junior years, I made the difficult decision to pass up a full scholarship to university so I could continue making connections and using my existing results to further my career as a professional. I worked for a few different farms for a number of years in my early twenties. I enjoyed all of them thoroughly, but I always had this nagging feeling that I knew how I would do things, or what I would do differently, if I had my own stable.
A few years later, with the support and encouragement of my partner Brendan Williams, we took a leap of faith and launched our business in 2018. It was definitely scary, but in the end it was the best decision we ever made.
What do you feel sets your program apart in the competitive equestrian world?
I think our program has a lot of value for a few reasons. Number one, I am very hands-on. I like to ride, lunge, and work with every horse in my stable so I know how they are, what they need, and the best way to bring out their peak performance in the show ring. I take horse care, management, and preparation very seriously, and I am a huge part of not only making those plans, but executing them.
The second thing I have always felt is a gift of mine is my ability to communicate. I grew up as a very visual and literal learner, so some trainers worked better for me than others. I try to give clear, concise, thoughtful training tips, and with that I really try to give my riders confidence. I needed a lot of positive encouragement to bring out the best in me, so I try to keep everything light while still advancing and growing in a sport that is very difficult.
Running a successful training business takes more than horsemanship. What business lessons have been most valuable to you?
I was brought up with a father who specialized in business and handling money, and I have him to thank for the ability to manage everything. What I think has earned trust from clients and riders throughout the years is transparency. I have always tried to be an open book when it comes to how much things cost and what to expect when riding, showing, and budgeting, not only for buying a horse, but maintaining it at a top level and protecting its value.
That said, I have been so blessed with amazing supporters throughout my career, which has allowed me to acquire and ride some incredible horses, and for that I am very thankful.
What tools, systems, or software do you rely on to keep your business running smoothly?
Right now, I keep most of my organizing on paper and in Google Docs, with QuickBooks for billing and sending invoices. We also use video technology programs so we can monitor and have eyes on our horses and stables at all times.
Who is on your team? Do you have people who help with the day to day, and what roles are most important?
When I started my business, my one slogan was that I wanted to do what I love, riding horses, with people I love. Over the years I have really tried to gather the strongest group of individuals around me who truly are the reason for all of my success. There are too many to list, but to name a few:
- Bethany Lee has been by my side since the very beginning of our business. I am lucky enough to have her assist me with coaching, riding, preparing, and managing my horses, but most of all I am lucky to call her a friend. She knows exactly what I need before I know.
- Sabrina Fox has managed my stable for the last few years and I could not do it without her.
- Ian Curry has been our farrier since the launch of our business. I could not imagine doing this without him. I was always taught a horse is nothing without its feet, and he constantly makes sure my horses’ feet are in top shape.
- Kristen Darragh, Tiffany Marr, and Cailin Drexler have been our vets since the beginning. I have had so many amazing animals with great stories, and I owe it all to the incredible group of people supporting them.
We know every day looks different as an entrepreneur. What does your favorite kind of day look like?
I am so lucky to be able to do many amazing things in my life. One of the best parts of having this as your life and job is being able to travel the world and have incredible experiences, while also pursuing horses.
My favorite day usually takes place at home, at either our summer or winter base. I really enjoy working with and trying to improve or teach my horses at home, whether that is flatting, trail riding, or jump schooling. I try to keep a nice balance between work and personal life, so after work I will usually try to get a workout in. My personal favorite is SoulCycle. After that, ideally, I am eating at a nice restaurant with close friends or enjoying time at home watching TV or cooking.
What has been the biggest challenge in scaling your business, and how did you overcome it?
One of my biggest personal challenges has not been internal or involving my personal stable. I have struggled greatly over the years to feel accepted and supported by my peers, many of whom are quite a bit older than I am. I think my decision to not go to university and pursue this instead was a newer choice for my generation, so I was one of the few who decided to do it. It was risky, but it really paid off for me in the end.
For a long time, I felt looked down on, and I felt a constant sense of people wishing me to fail. Being physically younger also made me feel like an outcast and very alone.
Over the years, I have done a lot of work and I am content in the fact that I do this for myself, for the horses, and for the people around me that I love. Everyone in life, and in this sport especially, has an opinion about what everyone else is doing. I think you have to do what makes you happy. I know what I am here to do and how I want it done, and I am extremely grateful to everyone who has given me the opportunity. I feel so lucky to have the people and horses in my life that I do, and that is success and happiness for me.
What do you think is the difference between being a great horseman and being a successful equestrian entrepreneur?
I think being a great horseman and a successful entrepreneur are very different things, and one of the hardest parts of life is balancing them. I always put my horses and their happiness first, but running our business and working with clients is a huge part of my life.
Communicating with horses is second nature for most riders at the top, however people skills are so important when working with clients and running a business. I have always felt that the relationships we have with our clients are what set our business apart, and what help me give confidence to my riders.
Was there a moment where you took a big risk? How did it turn out?
I feel like the biggest risk I took was in the early stages of my business. I always had a vision and a dream of how I wanted things run and what I would do if I was in charge of a stable. I could see it, almost taste it, but I had no idea how to get there and I definitely did not have the financial backing to do so.
Taking the first step, leaving my steady paying job where I could rely on a salary to put food on the table, was scary. There was no handbook and no directions on how to start, and no one who helped me prepare for what I needed or the team I had to create. It took a lot of trial and error and learning in the beginning, but ultimately I was able to create and pursue my vision exactly how I had it in my head.
What has been your proudest moment as a trainer and business owner so far?
I have been lucky enough to have many proud moments. I have been able to help many talented riders accomplish their goals, whether Hunter, Equitation, or Jumper oriented. Watching them grow and develop as riders and horsemen is very rewarding. The feeling of being a team, working hard toward a goal, and accomplishing it is so rewarding.
But personally, I get choked up even writing this. Watching my younger students grow up and blossom into the successful, confident, strong, passionate young adults they are brings tears to my eyes. I would like to think I played a small part in shaping them into the special people they grow up to be. Watching them continue to succeed in their own riding careers, while balancing college, new jobs, and life struggles with poise and confidence is what really makes me feel full.
Are there standout horses, clients, or wins that shaped your journey in a special way?
I designed my business from the beginning to be able to work with the people and families that I wanted to, ones that became our family. Working together to find the best horses for them, and training those horses with their kids, is such a rewarding process.
All my clients have been so special and I will hold a special place in my heart for all of them. The Swani family will always mean a lot to me, mostly because they took a chance on me when I was out with a broken leg and believed in me from the start. They still own some of the most wonderful horses in the country, and are a huge part of our life.
As far as horses go, I have had too many amazing horses to count. Trademark, Drumroll, Spoken, Paisley Park, and Monarchy are some of the greats that will go down in history for me. All of them brought me so many firsts and gave both their owners and me so much of themselves. I will be forever indebted to them.
A win that was very special for me was winning the 2014 USET Talent Search Finals. I grew up feeling that competing and being successful in the Equitation division was so out of reach, so being able to put in the work and win a major Equitation championship gave me the confidence to believe in myself. After that I felt like, wow, I actually might be good enough to do this. Maybe I do have a place in this sport.
What achievement are you most excited to share with the equestrian community right now?
My biggest achievement thus far has been the ability to continue to pursue the sport I love so dearly and call it my job. I hope that my story can help inspire someone, or give another person the confidence to chase their horse dreams no matter how unattainable they think they are.
Who do you admire most, inside or outside the horse industry, and why?
Right now I really look up to a dear friend of mine, Lillie Keenan. I grew up riding with her and know her closely. What she has done and accomplished for herself is remarkable. Her passion and love of the sport and her drive to represent her country is admirable. I still get to work with her closely and I feel grateful to know her and watch the process.
Where do you see Hesslink • Williams in the next 3 to 5 years?
Hopefully in the exact same place. I am so happy with the group of people and horses I have right now. I really love my job and look forward to helping and caring for the horses and riders we have currently.
My dream is to one day own my own farm, whether that is up north or in Florida, so maybe that will be my wish for the next five years.
What is one thing you wish more people understood about the business side of being a professional trainer?
I do not think people truly understand how hard it is to operate a full-time showing stable. Horses are animals and need 24/7 attention and care. It is hard to grasp how much they need from us to be able to continue to perform, stay healthy, and stay happy.
What keeps you inspired and motivated outside of the ring?
Outside of the ring, I have an amazing group of close friends, and I really look forward to being able to spend time with and celebrate with them.
Health and fitness also motivate me, so I try to work out at least once a day in addition to riding. I want to be the best version of myself in and out of the ring. Working out has been an outlet and stress relief for me, so I really try to prioritize it.
What advice would you give to young trainers or entrepreneurs who want to follow in your path?
I would encourage them to trust their gut and believe in themselves. I lacked a certain level of confidence that took me years to build. Hard work is a must. Opportunity will always arise for hard workers, and that does not just mean on the back of a horse. Continue to learn and grow as a rider, in horse care and management, and in business skills.
For fun, what is one ritual, habit, or superstition you never skip on a busy show day?
I have quite a few, to be honest. One thing I always do before showing is eat a banana. I have struggled with nerves and the mental side of this sport since I was a little kid, and years ago I was lucky enough to participate in the Horsemastership Training Session, previously known as the George Morris Excellence Clinic. There I learned from mental skills coach Tonya Johnson that the potassium in bananas can help reduce that “butterflies” feeling in your stomach. Ever since then, it has become a ritual for me before competition.
Over the years I have developed the skills to channel and use my nerves to my advantage, but I still keep this superstition for the mental side. Another thing I am superstitious about is ties. I have lucky ties, and I color-coordinate ties for days of the week or for bigger classes.
Geoffrey’s story is a reminder that building a meaningful equestrian business takes courage, clarity, and an unwavering commitment to both horses and people. From taking early risks to creating a program grounded in thoughtful horsemanship and strong relationships, Hesslink • Williams reflects the kind of intention that leaves a lasting impact on riders and horses alike.
You can learn more about Geoffrey’s work and follow his journey on Instagram at @geoffreyhesslink, and keep up with the Hesslink • Williams program at @hesslink.williams.
This is just the beginning of our Equestrian Entrepreneurs series. If you know someone whose story we should highlight, we would love to hear from you. Send nominations to hi@maremediaco.com.
Photography courtesy of Geoffrey Hesslink. Images by Shelby Phillips and Mackenzie Clark.
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