Seeing the Underdog: How Ryan Sassmannshausen Measures Success by a Horse’s Potential
- Lindsey Oaks
- 5 days ago
- 3 min read
1/28/2026, Wellington, FL - For Ryan Sassmannshausen, success has never been defined by a single ring, a specific height, or a predetermined outcome. Instead, it lives in the quiet moments—the ones where a horse finally relaxes, figures something out, and steps into the version of itself it was always meant to be.
“I genuinely don’t care what ring they end up in,” Ryan says. “I just want to see them become the best version of themselves.”
It’s a philosophy that has shaped his career as a rider, trainer, and horseman, and one that runs through every corner of Kinvara Farm, the family-run operation he shares with his mother Janet and his brothers. With farms spread across multiple states and a program that includes young horses, sale horses, and top-level competition mounts, Kinvara is a large, complex operation. But at its heart, it remains deeply personal.
Letting Horses Tell the Story
Ryan has built a reputation for seeing potential where others might overlook it. He openly admits he’s drawn to underdogs—horses that may have been misunderstood, mislabeled, or written off too soon.
“I love the ones that have been through a little bit,” he says. “The horses that maybe didn’t fit somewhere else or got upside down in the wrong program. If you give them time, consistency, and listen to them, they’ll tell you exactly what they want to be.”
That listening has paid off again and again.
One of the clearest examples is Rosalita—a mare originally imported as a jumper prospect. While others debated her future, Ryan felt it immediately.
“She didn’t want to be a jumper,” he recalls. “She was a hunter. She just had that brain.”
Developed patiently through the young hunters, Rosalita went on to become a dominant derby horse under Ryan, winning the majority of the international derbies she contested. But her story didn’t end there. After being sold, Rosalita became a once-in-a-lifetime partner for a young rider, Hazel McLean, going on to win Junior Hunter Finals, claim championships at the Royal Winter Fair, and earn Horse of the Year honors in Canada.
For Ryan, those moments matter just as much—if not more—than the ribbons he won himself.
“It’s one thing to win on them,” he says. “But watching a horse go on and make someone else a star? That’s everything.”
Selling Horses of a Lifetime
Ryan often jokes that he’s not in the business of selling horses—he’s in the business of selling horses of a lifetime. It’s why so many of his clients come back, and why he’s fiercely protective of the horses he develops, especially those he’s bred himself.
“I care where they go,” he says simply. “I want them to be loved. I want them to have a job that suits them.”
That mindset means resisting the urge to force a horse into a role it doesn’t want. Some become hunters instead of jumpers. Some turn into equitation horses when their resumes suggest otherwise. Others surprise everyone after being passed over entirely.
“There’s nothing better than being wrong in the best possible way,” Ryan laughs. “You think you know what they’re going to be—and then they show you something even better.”
A Family Operation, Modernized
With more than 80 horses, multiple farms, and team members spread across the country, running Kinvara Farm requires precision and communication. That need—born directly out of day-to-day barn life—is what led Ryan to create Questri, a barn management app designed specifically for the American equestrian industry.
Originally built to solve his own problems—tracking veterinary records, farrier schedules, daily tasks, and horse show logistics across locations—Questri has grown into a powerful, customizable tool now used by barns across the U.S.
“We built it the same way we build horses,” Ryan explains. “Slowly, thoughtfully, and with constant feedback. The app adapts to the barn—not the other way around.”
True to form, Questri isn’t about flashy promises or rapid expansion. It’s about making professionals’ lives easier, giving them back time, and allowing them to step away from the barn without things falling apart.
“If I can do my billing in five minutes from my couch and actually go to dinner,” Ryan says, “that’s a win.”
The Common Thread
Whether he’s developing a young horse, matching a rider with their perfect partner, or refining a piece of software, Ryan’s approach is remarkably consistent: pay attention, don’t rush, and let potential lead the way.
“Horses don’t need to be forced,” he says. “They need to be understood.”
It’s a simple philosophy—but one that has shaped countless careers, created unforgettable partnerships, and proven that sometimes the greatest success stories come from the horses no one expected.
And for Ryan Sassmannshausen, that’s exactly the point.
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