Who says you have to wait until you’re grown up to earn money doing what you love? If riding horses or ponies is your passion, there are many ways you can earn a little extra cash to pay for whatever you want—new books, video games, tack, or even a horse.
Two sets of siblings are sharing how they work with their moms to do just that. Whether it’s helping to ride a horse that their mom is training, or taking a timid pony and getting him used to kids, the Robertson brothers and Taylor sisters are equine entrepreneurs that love to spend their spare time at the barn and in the saddle.
Robertson Boys in Florida
As fourth-generation equestrians, Saer (age 12) and Flynn (age 10) were practically born in the saddle. Their dad is Brody Robertson, an internationally renowned jump builder and course designer. Their mom, Jen Robertson, grew up showing Arabians and competes nationally as a hunter/jumper rider.
Both boys started showing in lead-line, but it didn’t take long before they took over the reins. After Jen purchased a couple of Miniature Horses from a sale that needed a new home, she asked the boys if they wanted to try their hand at training them. It was their first chance to train their own ponies, and after Jen posted their progress on social media, there was interest in buying them.
“There was a girl who was paralyzed from an accident, so I figured the proceeds of selling the two Minis could go toward her medical bills,” explains Jen. “Those two sold within 10 minutes of me posting them on social media. Then I had more people ask for trained ponies, so I talked to the boys about this being their project at the farm.”
Saer and Flynn jumped at the chance. They work as a team with their mom on each new training prospect: Jen finds the ponies and purchases them, then helps with first rides and instruction. Flynn does most of the riding, and Saer puts together videos to advertise the ponies and to show off some tricks.
“Sometimes their videos get a little ridiculous,” says Jen. “They wanted to bring a pony into the house and play the piano with her. I just let it roll.”
“I like working with my mom and brother,” says Flynn. “Mom picks out the ponies and asks if we think we can ride them. We’ll say yes—I don’t remember a time we’ve said no.”
Each purchased pony or Miniature Horse gets a full veterinarian workup, with dental and farrier work usually needing to be done. The Robertson boys will take their time getting to know each pony, riding on the flat for a couple of weeks before introducing it to cross-rails. They try to ride every day after school to prepare not only for horse shows, but to sell the ponies.
“They’re both very good about their schoolwork,” says Jen. “Sometimes I’ll have to push them to the barn to ride because we’ve got a show to prepare for, but they’re very good about getting their barn work and schoolwork done.”
The boys are taught about the cost to care for a pony and the cost of horse shows by using the money made from each sale. Saer treats himself to a new video game, while Flynn puts most of his into savings for the future.
“It makes going to shows more affordable when they sell a pony,” says Jen. “That’s how I afford to show myself.”
Taylor Girls in Texas
On the western side, sisters Finley (13) and Evie (11) take a different approach to the family training business. Inspired by their mom, Hope, who takes in training horses for both western and English riding, Finley and Evie decided they wanted to help out more around the barn.
“Captain was the horse that made me want to start working with horses like my mom,” says Finley. Captain was a Miniature Horse who was purchased by a first-time horse owner family and became difficult to handle right away. Something drew Finley to the bay gelding immediately.
“I was determined to help him trust again,” she recalls.
Hope loves to see how her two daughters approach horses differently. She says Finley has a more natural feel to working with horses and can understand what is needed. This allows her to do the work on her own (with mom’s guidance) and learn alongside the horse. Evie, on the other hand, is a good reader of horses with insecurities, and likes to handle the horses as a secondary trainer alongside her mom.
“They are two very different kiddos, but I feel that they both are very aware of what they bring to each horse,” says Hope.
While Evie works alongside her mom on client horses, Finley will work with her own project horse to prepare for sale. Their parents use it as an opportunity to teach them about finances and responsibilities. Hope covers most of the major bills, but makes sure Finley knows how much money is coming in and going out. When it comes time to sell, Finley does her own research and helps her mom come up with a price and social media post to advertise the sale.
Evie is paid in special dates with her mom or dad for being helpful during a training session. Finley saves her money and has yet to really splurge on any big purchases. And while the money is nice, each sale can be difficult to manage for the kids.
“We talk about how it’s bittersweet when a horse moves on, but we make the most out of the experience,” says Hope. “We will talk about how the horse is going to a family to make them happy as well, and how it feels good to be a part of his training. She can look the owner in the eye and say, ‘You have the best horse in the world. You’re pretty lucky.’”
This edition of “Equine Entrepreneurs” about siblings who train appeared in the March/April 2025 issue of Young Rider magazine. Click here to subscribe!
