By Jessica Grutkowski
Portraits by Evelyn Szczepanek
Rachel Truair spent her entire adolescence chasing her dream of “going pro,” and when it finally happened, she realized it wasn’t her destiny. Growing up in Austin, Texas, Rachel experienced horses for the first time at age 5 at a local summer camp. “I fell off and cried, but the instructor told me I wasn’t a real horseman until I had fallen off 10 times,” she said. “Her logic made sense, so I got back on.”
Despite being a self-described “wimpy kid,” the challenge of learning to ride horses was appealing and Rachel began taking weekly lessons at Switch Willo Stables. “When I finally got my driver’s license, I drove to the barn and asked to work in exchange for more lessons. I expected to paint jumps, but to my surprise, I was offered a working student position,” she said.
Rachel worked closely with professional Kelly Lorek, and nannied for a client’s daughter, then-5-year-old Megan Bifano. The Bifanos lived in a local equestrian subdivision, but kept their horses at Switch Willo while the facility there was under construction. “I loved my job. Every day I thought to myself, This is going to be my career. I couldn’t wait to work with horses,” Rachel said.
Throughout high school, Rachel continued working at Switch Willo and counted down the days until she could be at the barn full time. “I graduated early, and didn’t plan on attending college,” she said. “Everyone said I was ruining my life, but I didn’t care—I had made up my mind.”
Out of school, Rachel worked for Jim and Joan Henson at Foxglen Farm in Argyle, Texas. “I was happy at Foxglen, but the Bifanos approached Kelly and I with an amazing opportunity to run Madrone Ranch Stables, the newly completed facility in their subdivision,” she said. “Kelly managed the riding and training, and at 20 years old, I was running a full 40-stall community barn. It was surreal.”
Rachel felt accomplished, but isolated. “I lived in a tiny efficiency apartment under the hay barn, and all my friends were in college,” she said. “I had succeeded—but it didn’t feel that way, and I was scared to admit I had made the wrong choice.”
Fate Changes Course
While Rachel mentally struggled to process her emotions, her body physically forced her to take a break. “I had severe back pain and could hardly move,” she said. “My doctor said I had two herniated discs and told me to find a new job.”
Rachel sought out the advice of an executive career coach, who told her to think outside the box. “I had never considered anything other than horses. She had me apply for the first job that seemed interesting,” she said.
Rachel interviewed for a corporate pet relocation service start-up. Little did she know that day would change her life forever and launch her marketing career. “It was like being a wedding planner, but for pets that were traveling. I stayed for nine years,” she said.
Rachel went back to school at night, and earned an undergraduate degree from St. Edwards in Austin. She also secured an MBA from The University of Texas at Austin. That’s where Rachel met her husband, who coincidentally also took a circuitous route to getting his college degree. They married in the Adirondacks, and have a home on Saranac Lake where they spend several weeks each summer.
Rachel’s life was falling into place, but she could no longer ignore her back pain. “My husband pushed me to get artificial disc replacement surgery. After 10 years of chronic pain, I woke up pain free. I was happy in my work and home life, but I missed riding.”
Too nervous to get back in the saddle just yet, Rachel connected with horses in the safest way she could—the internet. She tuned into equitation finals, hunter derbies and Grand Prix—all from the comfort of her laptop. “I thought about posting marketing tips, but mostly enjoyed the equestrian content,” she said. “I posted a few videos for fun.”
On TikTok, Rachel cleverly tapped into current trends and adapted them to the equestrian community. “I made one called the ‘Big Eq starter pack,’ and another titled, ‘What your saddle says about you,’” she said. “They went viral, and people were like, ‘Who is this person?’ I made some new friends and loved being part of the conversation.”
More than ever, Rachel yearned to be back in the horse world—but was scared to fall off and hurt her back. “I considered being an owner,” she said. “I crowdsourced on Facebook regarding costs to campaign a derby prospect on the A-circuit, and began saving.”
Finding Her Way Home
In November 2021, Rachel purchased her first investment horse, Diaronimo, or Nimo for short, with the help of professional Kalli Smith at Texas-based Monarch Stables. “I sent Nimo to Wellington that winter to gain experience,” she said.
Rachel hadn’t planned on riding again, but her husband insisted that she needed a saddle. “I got rid of all my riding gear when I was burnt out,” she said. “The new saddle led to a new helmet, and boots—the works.”
When Nimo returned to Texas, Rachel decided to hack him for fun. “My trainer asked if I wanted to jump a few,” she said. “I thought, Maybe I want a horse for myself!”
Still casually riding, Rachel saw no harm in scrolling through Facebook sales posts. “A horse named Winchester caught my eye, and I became obsessed. I decided to message his owner,” she said. “Winchester was in Georgia at an Arabian barn, looking for a second career after being imported to do the Big Eq.”
Rachel was a little nervous to tell Kalli about her Facebook find, but luckily, she saw his potential too. “I was happy that my instincts were correct, and she agreed to come try him with me,” she said.
Rachel learned the horse’s barn name was Chester, and during the trial she asked the girls watching to take her photo. They said, “Larry, put your ears up!” Rachel said, “I thought his name was Chester!” The girls giggled and said, “It is, but we think he looks more like a Larry.” Rachel agreed and the name stuck: Chester became Larry, and he headed to Texas.
In 2022, Rachel competed as an adult amateur for the first time at the Pin Oak Charity Horse Show. “Here I was in the Long Stirrup Division, terrified, on a horse who could probably do the course without me,” she said. “My plan was to jump the first fence, and then leave the ring. But the first jump felt so good, I kept going.”
Rachel calls Larry her heart horse. “He’s huge with a personality to match. He can be spooky, but in a gentle, ‘big goofy gelding’ way,” she said. “He is particularly offended by white flowers. I always bring a stash I made for him to the warm-up ring.”
Eventually, Rachel sold Nimo and purchased Douglas De Riverland, a tall, dark brown Selle Franҫais. “We competed in the Low Adult Hunters last winter in Wellington, and it was a dream come true,” she said. “My goal is to get back to the 3’ Adult hunter and equitation divisions one day.”
Amateur Dreams
In her current role as chief marketing officer at Simpro Software, Rachel is able to enjoy horses in a way she wasn’t previously able to as a Junior. “I always dreamed of showing at the Wellington Equestrian Festival (WEF) and Kentucky Horse Park (KHP),” she said.
Rachel remembers hearing stories about the Bougainvillea-covered barns in Wellington as a working student. “The first year I showed at WEF, it was a ‘pinch me’ moment,” she said. “The ringside palm trees, tropical flowers and stunning horses with impeccable turnout—it was like winning a blue ribbon before entering the ring.”
Competing at the Kentucky Horse Park has always also been a bucket-list venue for Rachel, ever since she visited Lexington at age 12 with her father and best friend for BreyerFest. “We brought our model horses on the airplane—complete with shipping wraps and blankets,” she said. “Last summer on the way to show at KHP, I had a flashback and thought, My 12-year-old self would have been so proud.”
During the winter months, Rachel boards her horses at Epic Stables in Wellington, Florida, which is run by international show jumper Chris Pratt and his wife, Jen Pratt, a half-sister to Megan Bifano (now Kay)—the little girl Rachel used to babysit in Texas. “It’s a full-circle moment being reconnected with the Bifanos,” Rachel said.
When her schedule allows, Rachel travels alone to Wellington a week early to practice. “I have to admit, being down there without kids and just the horses feels like a spa retreat! The Pratts take excellent care of me and the horses,” she said.
A Balancing Act
Rachel’s husband and children—Pendleton Grace and Theodore—travel as a family to watch her compete in Florida and Kentucky at least one week each season. “My husband’s birthday is in March, and I think he’s spent more of them at WEF Week 11 than he would like to admit!” she said.
Rachel and her family enjoy spending time in Wellington and Lexington, especially. “I could see ourselves living there one day,” she said. “My daughter is obsessed with sweeping and cleaning stalls. My son prefers the machinery and emergency services at the show grounds. We always hit the beach for some family time.”
It’s a delicate balance between Rachel’s executive position, equestrian goals and motherhood. “What I’ve learned is that adult life requires constant reevaluation,” she said. “As a Junior, I always thought riding meant staying in one place, with one trainer. But as an adult, I learned every year brings different goals, experiences and trade-offs. And that’s OK.”
With both of Rachel’s children now in elementary school, their lives are busier, and so is Rachel’s work. “The company I work for has doubled in size since I started, and this summer I decided to move my horses back to Switch Willo Stables in Austin,” she said. “My horses get weekly pro rides, but I also get to just go out and groom, tack up and ride casually. It’s only 10 minutes away from my house, and I love that. The kids love spending time with Sugar Snap, their miniature pony.”
According to Rachel, surrounding yourself with flexible, supportive trainers is key. “The sport should bring joy,” she said. “We’re spending time, money and energy—and often time away from our families—so it has to be something that can evolve with us.”
Follow Rachel on Instagram @racheltruair and TikTok @rtruair
Photos by Evelyn Szczepanek, www.esequinephotography.com
