Welcome to the very first installment of our Equestrian Entrepreneurs series, where we spotlight the diverse stories of equestrian professionals building businesses rooted in their passion for horses. We’re starting with Ashley Tolton, a retired professional rider and trainer turned full-time equestrian artist. Based in a small town in Eastern Oregon, Ashley runs Ashley Tolton Art, where she creates sophisticated oil paintings that celebrate the beauty, tradition, and deep connections found within the equestrian sport.
Ashley’s journey is a blend of horsemanship, artistry, and entrepreneurship. We had the chance to sit down with her to learn more.
To start, please introduce yourself and tell readers a little about your business. Where are you located and what do you specialize in?
My name is Ashley Tolton and I’m an equestrian and oil painter. My equestrian focused business is really a celebration of the bonds we form with our horses, the traditions found within our sport, and the beauty that can be found in those everyday moments. I live in Oregon, USA, but ship paintings all over the world. I specialize in oil painting and in pieces that not only capture the physical presence of the horse, but also their individual characters. I work with clients and collectors who share a deep appreciation for the equestrian lifestyle — who value craftsmanship, tradition, and the artistry of timeless pieces. Whether you’re commissioning a custom portrait or selecting a limited edition fine art print, my goal is to create meaningful work that reflects the refined traditions of the equestrian world and elevates any interior with quiet sophistication.
How did your journey with horses begin? Do you come from a riding background, and how has that influenced your art?
It’s funny, my background with horses is a little complex. No one in my immediate family was involved with horses in any way. However, my great grandfather was a cowboy, an adventurer, and a famous American West artist who created the most incredible equine sculptures. So to some extent, horses and art are in there somewhere. I was the typical “born horse crazy” kind of girl. I have literally never known a time in my life when I wasn’t absolutely enamored by them. My parents were very supportive in my riding career, so I started taking lessons at the Stanford Red Barn when I was very young and the rest just kind of evolved from there. I had a wonderful junior career, I became an assistant trainer, eventually opened up my own barn and that lifelong relationship with the equestrian world is undeniably what influences every single brushstroke of mine.
What first inspired you to start painting and creating as a business?
Art was one of those things that I always did. I was really good in school and learning always came really easily to me, so I frequently got bored. I was the kid that got in trouble for drawing horses all over their homework and school notes. With that, I actually went to college and got my degree in Pre-Veterinary Medicine, since science was and still is a huge passion of mine. However, when it came down to applying for vet schools, I realized my true passion was actually working with horses and so I became an assistant trainer. Long story short, in 2018, I was riding a very young colt and had a really bad fall that injured my spine. Though I’m fine now and fully healed, that fall made me reflect on the longevity of what I was doing. It inspired me to look into other careers that would allow me to ride and show my own horses, but not have my income dependent on it. That’s where the idea to start Ashley Tolton Art came from. My love for horses and equestrian sport (and those occasional vet bills) are what keep me motivated and in love with the job, every single day.
What do you feel sets your artwork apart in the equestrian and western art world?
I feel like what sets me apart, and all artists for that matter, is that we inevitably have our own voice. We all see the world in a unique way. For me, I find that I’m very much drawn to the way light and shadows play with the form of the horse. I’m fascinated by the slight abstractions I can create by focusing on things like the horse’s braids, or the stunning display of musculature as a horse is jumping a 1.60m fence. I tend to gravitate towards minimalistic and sophisticated styles that really show off the beauty of our equine athletes.
As an entrepreneur, what business lessons have been most valuable to you in running an art studio?
I think the most valuable lesson I’ve learned is just not to give up. It’s so much like riding where, on a daily level, you may not feel like you’re making much progress, but when you step back and look back over a year to two-year period, you realize that leaps and bounds have been made. So I guess persistence and unyielding optimism.
What tools, systems, or software do you rely on to keep your art business organized and growing?
So many! First and foremost, I actually heavily rely on other photographers, so shout out to Morgan Froment, Madeleine DB, Shelby Phillips, Nicole Schultz, SAS Equestrian, Ashley Neuhof, and so many more who have so graciously allowed me the use of their photos as references. I work with a lot of photographers to help me get photos of client horses, in the instance where I’m not able to travel and take the photos myself. Other software I rely on would be Adobe for streamlining photo editing and client signatures, Apple Products which allow for easy sharing and it’s what I use to see my references as I paint, and Squarespace because they have a great and easy platform that looks professional and is so easy for clients to use.
Who’s on your team — do you have anyone who helps with marketing, logistics, or the day-to-day side of things?
Right now, I’m a one-woman show, which can get so crazy at times! In the future, I would love to hire a team, but for now, I enjoy knowing all aspects of my business.
We know every day looks different as an artist. Can you describe what your favorite type of day looks like?
My favorite type of day would always start with a cappuccino. During this time, I answer emails, I post on social media, and just take some time to connect with the world. I then go out and ride my horse, where I lose all sense of time, but it usually takes me a few hours. Then I would head inside and make some super fresh and delicious meal, which then sets me up for a great day of painting. I like to spend 5-6 hours in the studio, just getting lost in the creativity. By evening time, I clean up, go outside and take my dogs on a walk, do one final check on the horses and do any chores for them, come in, hang out with my husband and eat some great food. That’s a pretty great day to me :).
What has been the biggest challenge in growing your art business, and how did you overcome it?
I think one of the biggest challenges was that I don’t have any degree or training in marketing or advertising. Though I come from a savvy business family and I’m very comfortable with the bones of running and operating a business, I’m naturally a pretty introverted person, so learning how to market myself and the psychology behind business marketing was an enormous learning curve. We don’t have TV in our house, so the first few years of my business I’m not even joking, I spent two hours a night learning about SEO, web design, human psychology, marketing techniques, social media strategies, photography, video editing… you name it, I was obsessively learning about it.
What do you think is the difference between being a talented artist and being a successful creative entrepreneur?
Well, I don’t think they have to be mutually exclusive by any means. I know artists come with the stereotype of being emotional and only inspiration driven, so they’re therefore a little flakey. Though I definitely know artists like that, I’m almost the complete opposite. Science, business, numbers, analytics are all things that come easily to me and I had to learn to be a talented artist. But as far as the difference would go, I don’t think they have to be that different.
Both are creative, both involve learning and problem solving. Being an entrepreneur maybe requires a little bit more left brain and requires more social skills, whereas the creation of art requires a bit more right brain and is usually a bit more isolating. To be an artist you need to be in tune with your creative side and disciplined. To be a successful entrepreneur, I think it helps to be able to take the emotion out of things, while also remembering that you are a customer service based industry that requires social skills, discipline, and great communication.
Was there a moment where you took a big risk — maybe a show, a commission, or launching a new collection — and how did it turn out?
I think the decision to start this business in general was a big risk. I broke all the rules. I had saved up money, but I wasn’t working another job for supplemental income, I don’t even think I was that great of an artist when I started, and I knew nothing about marketing and social media. I had so much to learn and so much growing I needed to do, but all in all, showing up daily to learn and improve incrementally, got me to where I’m at now and I wouldn’t change it for the world!
What has been your proudest moment as an artist and business owner so far?
There have been a few markers that really stand out to me. There have been a few instances where artists I really look up to have engaged with my work and that was incredible. I have some unbelievably supportive clients, as well as some high profile clients that I’m incredibly grateful for. There have been some riders that I really look up to that have enjoyed the paintings I did of them and that always feels so incredibly special. And of course, every time I hit a new top sale item, it feels great and very validating, though it’s definitely not about the money. No one moment stands out, but there are a lot of really special small moments that I cherish.
Are there particular works, shows, or commissions that hold a special place in your story?
I have this one piece that I did in 2022 that initially stands out to me. It was the piece that I felt like things started to click. It was by far my most accomplished piece up to that point and it was the marker that I was getting a hang of this art thing. The other work that stands out would be this series I did in 2024. It was a small series of five 9″x12″ paintings, but it was the moment I decided to change my business to solely equestrian art. It was the first time I felt like I really honored what it was that I wanted to be creating and it was the moment that I allowed myself the space to accept that I just am “that crazy horse girl” that never grew out of drawing horses, and that’s okay.
What achievement are you most excited to share with the equestrian community right now?
I have three paintings that I finished earlier this year that I believe are my most accomplished to date. Though they can be found on my website and Instagram, they’ll be going with me to the Sunshine Series at the Desert International Horse Park in November and I’m so excited for people to be able to see them in person. More often than not, even with the best photo, social media doesn’t do the artwork justice, so it feels like a special opportunity to be able to present them to the public.
Who do you admire most — whether in the art world, the horse world, or beyond — and why?
I admire horsemanship the most. I admire people who are unabashedly willing to put the horse first. There are so many talented trainers and riders out there, but I admire when it goes so much deeper than that. I love when people are willing to do the research and truly learn the ins and outs of good horse care and training.
Where do you see your art and business heading in the next 3–5 years?
Hopefully just onwards and upwards. I want to do right by the clients who have stuck with me from the beginning, I would love to get even bigger clients, I would love to create some large scale pieces for people, and of course I’d love to just continue to hone my skills and continue pursuing my own style and voice in my art.
What’s one thing you wish more people understood about the business side of being a professional artist?
That it takes so much more time and care than maybe they even realize. When you buy a piece of art, you are paying for the years, the hours, the failed attempts, and the triumphs that all led us to this point. But I also want people to realize how truly special investing in art can be. Not just from the artist perspective, but historically as well. There are paintings that have lasted 500+ years. Photos may be lost or forgotten or left on a hard drive, but a painting is a true keepsake and one that has enormous historical significance and I think that’s pretty cool.
What keeps you inspired and motivated outside of painting?
Horses and travel. Horses on the daily provide me with endless inspiration and connection to the sport. I’m so lucky to be able to go walk outside and play with my horse whenever I need a break or an emotional reset. Then I also try to travel when I can. It’s an important mindfulness practice for me. I don’t really travel to resorts, I travel for experiences and lessons on culture. I always come back feeling refreshed, inspired, and grateful.
What advice would you give to other equestrian creatives who want to turn their art into a business?
Just do it! Start now, start small, start slow, just start. You can figure out the details along the way. I’m not saying to just forsake your savings and blow everything you have on it… have a strategy and a game plan, do your homework on the business beforehand, but nothing is stopping you. You don’t have to have all the answers to start, especially if you start small and slow.
For fun: do you have any rituals or habits that help you get into a creative flow before you start painting?
Kind of. Similarly to visualizing your course before you go into the show ring. I usually spend the morning visualizing my artwork — how to approach it, where to start, how I’m going to put brush marks down, etc. Also, when in doubt, I’ll just make myself go sit in the studio surrounded by art. If I need a minute to get in the zone, I literally just sit on the floor and look at the art around me and that settles me enough to get into the zone.
Ashley’s story is a reminder of how much passion and creativity shape equestrian businesses today. You can explore more of her work at ashleytoltonart.com and be sure to follow her on Instagram at @ashleytoltonart.
This is just the beginning of our Equestrian Entrepreneurs series. If you know someone whose story we should highlight, send nominations to hi@maremediaco.com.
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