Long before Olivia Cliver ever jumped a grand prix or competed in an FEI World Cup qualifier, her sights were set on a different goal: She wanted to take her off-the-track Thoroughbred gelding, My Mitch, to the advanced level of eventing and compete at the North American Young Rider Championships. 

“When I was a kid, I saw Rolex [Three-Day Event] one year on TV, and I was like, ‘I want to go do that,’ ” she said. Cliver, whose horse showing career began in the hunter rings at local shows in Texas and New Mexico, spent six years immersed in the eventing world, working for the likes of Olympian Mike Huber, Tik and Sinead Maynard, and Heather Morris to improve her skills. 

While they did make it to the advanced level, after missing her opportunity at Young Riders due to a torn rotator cuff, Cliver started to question whether she wanted to remain in the eventing world. 

“When I sold My Mitch, I realized that I only followed my eventing dreams because I had a horse that I really loved and trusted,” she said. “The thought of doing cross-country [at that level again] did not intrigue me anymore. I’m not normally a nervous rider, and I just started to pick up that cross-country was making me anxious. So I thought, ‘OK, let’s regroup—how do I make riding grand prix happen?’ ”

Her pivot back to show jumping has paid off: Cliver, 31, now uses the skills she learned in eventing to navigate five-star grand prix tracks and FEI World Cup qualifiers. 

“I think the bravery, [jumping fences] with speed, and being comfortable jumping things on angles were the three biggest skills I learned from eventing,” Cliver said. “It was a hard adjustment at that level, going from eventing to show jumping. The difference in eventing and show jumping is that in the cross-country, it’s big, tricky and challenging, but you have more times in between fences to regroup and organize. Whereas in show jumping, it’s all technical, and it all happens very quickly, so you don’t have a lot of time to regroup. Also, the rails fall down [in show jumping]!”

After backing away from the eventing world, Cliver moved back to Midland, Texas, married her husband, Carlos Flores, and started her training and sales business, On The Mark Equestrian.

“There’s such a need in this town for a quality program,” Cliver said, who grew up in a non-horsey family and got her start with horses when her grandmother gave her a hobby horse as a young child. 

“I was that kid years ago when I first started riding—we didn’t have a program like mine back then; my mom and I traveled all over so I could ride in hunters, 4-H, polo, whatever. I wanted to start my own business here in order to give back to my community in that way.” 

Most recently, she and her grand prix partner, Connor 69, achieved back-to-back wins at the Pin Oak Charity Horse Show circuit in Katy, Texas, topping the $50,000 Southern Way Farm Grand Prix on April 5 and the $100,000 Hildebrand Family Grand Prix on April 12. Cliver also won the Tom Pickard Sportsmanship Perpetual Award. 

“I cannot believe how far ‘Connor’ and I have come,” Cliver said. “We’ve definitely had our setbacks along the way, but he’s been more than we ever thought.”

Four years ago, Cliver went on a horse shopping trip in search of a grand prix horse for herself, with the goal of competing in her first FEI grand prix classes. After trying 20 other horses, Cliver sat on Connor—and the connection was instant. Although Connor is 17.1 hands and Cliver is a petite 5’5”, Connor’s size did not intimidate her. 

“Everyone felt like Connor needed a kinder, softer, ‘take the pressure off’ ride,” Cliver said. She gathered a group of owners: Sonja Register, Becky Young, Sarah Philpy and Laura Johnson, together to purchase the then 8-year-old Holsteiner bay gelding (Connor 48—Brandy, Contender). Shortly after, Cliver began mapping out a plan for their success. 

“I wanted something that we could go all the way with; if I had Connor, I wanted to do it right,” she said. “Connor has all the scope in the world, so it was more the question of ‘will this partnership work?’ 

“Connor has two personalities,” she added. “He is the kindest horse, but he can also be a little difficult and stubborn, which makes him a great competitor. But I think all of the 1.60-meter horses have that little quirkiness about them.”

When Connor first arrived at her barn, Cliver quickly realized she had some retraining to do.

 “At first, Connor was constantly on the defense; he would have a huge overreaction to things sometimes,” Cliver said. “There were so many things Connor was particular about: He’s very ‘stranger danger.’ He likes his people at all times, he hates water on the ground, and he doesn’t like the wash racks because he doesn’t like water. So we had to figure out how to take the pressure off of him while earning his trust.

“One day Connor escaped, and my two grooms had him cornered on the bridle path,” Cliver said. “Connor was just running back and forth charging at them; he was scared and a bit overwhelmed about being in a new situation with new people. I quickly ran out with a cookie—when I worked for Tik, he had always taught me about being aware of our body language around the horses. And that was a lot of it [with Connor]; I always thought about how can I come at him from a very neutral place, so he knows I’m not threatening? That day, I just turned my body completely sideways, didn’t look at him, held my hand out, and I just played the retreat game. As soon as I was taking slow steps toward Connor and he would stop and look at me, then I would retreat and walk away. And then he would be like, ‘Wait, why are you walking away from me? You’re not coming at me?’ Then I was eventually able to get Connor to come to me. He ate the cookie, and then I put the halter on him, and I took him back to his stall. We had a couple of grooms whose eyes became wide open to how you can be nice to horses and that they will respond well.”

Cliver also quickly discovered that turnout was an issue for Connor, and she had a small paddock built for him so he could spend more time outside. “I wanted to let him be a horse as much as we could,” Cliver said. 

But six months into their partnership, she still struggled to get Connor to stay out by himself. That was when Cliver had another idea: She went in search of a miniature horse to be Connor’s constant companion. 

“When I told his owners that I was going to try to get him a mini, they were like, ‘This is going to go one of two ways: he’s either going to be obsessed with it, or he’s going to hate it,’” Cliver said. 

Apples, a 5-year-old gray mini mare, immediately became Connor’s best friend. Apples lives in the same stall as Connor and sometimes accompanies him to horse shows, but she also is comfortable being left at home while Connor travels to FEI shows. 

“Connor loves Apples; it’s the cutest partnership,” Cliver said. “It’s a nice balance: I can take him away from the mini pony, and Apples has been the most perfect thing ever because she likes him, but she’s not obsessed with him. If I take Connor away from her, she’s not screaming for him in his stall. But you cannot take Apples from Connor. If he gets left in his stall and Apples gets pulled out, the whole barn is going down.” 

As Cliver and Connor’s partnership strengthened, Cliver began working with October Hill Farm Sporthorses, located near Weatherford, Texas. Over the past three and a half years, they have helped her develop Connor and bring him up from the smaller grand prix ranks to World Cup qualifying classes. Both barns attend many of the same show circuits throughout the year together. 

“October Hill has helped shape me into the rider and competitor I am today, and I will always be grateful for that,” she said. “One saying that’s stuck with me is, ‘learning by doing.’ You can’t expect to win the first time you move up; you just have to do it, learn from it, and trust that with time and good rounds, the results will come. It taught me to give myself grace and just keep showing up.”

In September 2023, Cliver and Connor clinched their first national grand prix win in the $30,000 Brownland Grand Prix (Tennessee). The week prior, Cliver had dislocated her kneecap and torn the medial patellofemoral ligament in her left leg in a fall from a different horse, and she had been unsure if she could compete with Connor at all. 

“I didn’t ride for the entire week leading up to the grand prix,” she said. “[October Hill trainer] Nico Gamboa rode Connor for me during the week, and then I got on Connor the Friday before the grand prix. I couldn’t even get on him; the knee injury was so painful.

“It was kind of funny; I’ve had so many setbacks in my life that my mom and I always talk about, ‘Focus on the donut, not the hole,’ because I’ve had a lot of stupid things happen to me,” Cliver added. “[When I hurt my knee], I was also preparing for World Cup season—after Brownland, we were going to a bunch of different shows in the fall for World Cup qualifying classes. I couldn’t believe I had gotten injured right at that time, but we made it work.”

Cliver didn’t allow the acute injury to halt her fall season; she and Connor went on to place second in the $78,000 1.50m FEI Grand Prix Qualifier Welcome at the 2023 Sacramento International World Cup Week (California) and then finished seventh in the $226,000 FEI Longines FEI Jumping World Cup CSI4*-W at the 2023 Las Vegas National Horse Show. The pair also competed in their first five-star grand prix last fall and hoped to compete in their second five-star grand prix during the 2025 Thermal circuit, but an abscess kept them from that goal. 

“Things get going, and then we have a stupid setback like that,” Cliver said. “Such is life, but it’s frustrating! After that, I was determined to make Pin Oak successful for us. I’m a firm believer that the comeback is always greater than the setback as long as you keep chipping away at it.” 

But then a week prior to this year’s Pin Oak, Cliver reinjured her knee again. “I was shutting a drawer with my bad knee, which doesn’t sound like a big deal at all, but I dislocated that kneecap again,” she said. “I was frustrated—I had told all of Connor’s owners that this was going to be our year at Pin Oak—but I was determined to make this work. I used kinesiology tape on my knee [for the class] and I was like, ‘It’s not going to keep me down.’ It’s a weird injury; it’s really painful at times.” 

Although surgery was suggested, Cliver has tabled that, for now, in favor of physical therapy. 

“We never really have an off-season for our sport anymore,” she said. “It’s hard.” 

For the remainder of 2025, Cliver has her eyes set on competing Connor in several more World Cup qualifying classes with her ultimate goal being to qualify for the 2026 FEI Longines World Cup Final that will be held in her home state, in Fort Worth. Cliver also has been campaigning a second grand prix horse, a 12-year-old Westphalian gelding named Interactive Mortgage Cayjano, owned by Johnson Equine LLC. Her plans are to market him and then hopefully purchase a 7- or 8-year-old to develop up through the jumper ranks. 

Although Cliver has transitioned disciplines within the horse world, she has dedicated her life to the sport she loves. Since Cliver graduated high school, she has had a running joke with her stepdad, Mark Philpy, who is her biggest supporter.

“Originally he wanted me to go to college, and so I made a deal with him that I was going to take one gap year in between high school and college for the horses,” she said, “but now we’re on gap year 13!”