On a recent trip to Dubai, amateur rider Sasha Khursheed Said reconnected with a long-lost relative, uncovering a piece of equestrian family history. Her great-grandfather, she learned, was the veterinary inspector at the Renala Khurd Redmount Stables, a breeding farm that produced top-tier cavalry horses in pre-Partition India. 

“Had you asked how I got into horses prior to that trip, I’d have told you I was just drawn to them,” she said. “But discovering this legacy confirmed what I’ve always felt: They’re in my DNA.”

And perhaps it’s her equine heritage that has kept Said fighting her way back into the saddle over the decades. 

Said grew up in Norfolk, Massachusetts, a first-generation American with a rich Japanese and Pakistani heritage. But as one of only two non-white students in elementary school, she often felt like an outsider. 

From the time she learned to talk, she was asking for “horse” and begging to ride. By 5 she was taking up-down lessons at a local farm. Horses, as they do for so many of us, gave her a safe space to be herself.

Her desire to do more quickly outgrew basic instruction. She idolized Karen O’Connor, Bruce Davidson and Phillip Dutton and wanted to be an eventer, but there weren’t any eventing programs in her area. So she began riding at Woodlock Farm, a competitive hunter/jumper and dressage barn where she could improve her skills and start competing. 

But without owning a horse, which simply wasn’t in the cards, she felt her riding plateau. She knew she needed to find a way to spend more time in the saddle, so she negotiated to lease a horse at the barn in exchange for mucking stalls, tacking and turning out five days a week.

But as Said entered high school, she began to realize that her small town couldn’t match her desire to expand her boundaries and set herself up for future success. She convinced her parents to let her investigate prep schools, and she secured admission to the prestigious Deerfield Academy. There weren’t many stables near her school, so Said put her riding on hold during the academic year and picked it back up on summer breaks at home.

During those formative high school years, while she was at home academically, she felt like a fish out of water with her classmates. At a school of 600, she was one of only four South Asian students, and most of her classmates were from an entirely different level of privilege and access. She was determined to find her place—on her terms. 

Around the same time, Said started to notice increasing discomfort in her upper back, but she chalked it up to a combination of hours spent studying and being a three-season athlete. 

During the summers, she reconnected with horses by taking jobs grooming and teaching beginner lessons at local farms. 

“Even when I wasn’t riding regularly, I was still very much in love with horses,” she said. “They’ve always been my happiest place on earth.”

But in college at Brown University (Rhode Island), as she threw herself into rowing and her finance degree, juggling multiple part-time jobs while working toward a 4.0 GPA, she realized something about the horses she loved so much.

“It was too hard to be around horses on a limited basis but not be able to totally devote myself to it,” she said. She decided to step away from horses until she had the time and money to go all-in.

After graduation, she entered the world of finance, looking for work that offered the greatest intellectual challenge for the biggest paycheck. When colleagues asked why she chose to work in hedge funds, her answer was simple: She wanted to make a positive impact, and she wanted to be able to afford returning to the horse world.

As an outdoor enthusiast, she found New York’s “concrete jungle” challenging. Almost daily she biked from her Upper West Side apartment through Central Park, stopping to feed treats—sometimes sugar cubes she’d surreptitiously pocket at meetings—to the carriage horses. She wished, on those days, that there was a way she could pursue horses and her career simultaneously.

In New York, she promised herself that she’d put her nose to the grindstone to reach financial independence as fast as possible so that she could ride again in the way that she longed to. When she traveled, she’d allow herself to dip her toes back into horses, resulting in riding experiences that ranged from galloping across a beach in Bali to doing passage on a Lusitano at a classical dressage school in Portugal. 

After four years in the city, the neck and back discomfort she’d begun noticing in high school had escalated into near-constant pain. She saw multiple orthopedic specialists but none could identify anything physically wrong. Most doctors believed that her pain was caused by a combination of job stress and sitting at a desk 10-12 hours a day. 

Said decided to leave her job and move back to Boston, thinking she could spend some time with her family while focusing on finding the source of her undiagnosed pain. She tackled her next chapter with purpose: She spent little time at a desk, exercised daily, did physical therapy, yoga, meditation and Pilates. She saw multiple specialists and researched heavily. But orthopedists, rheumatologists, neurologists, endocrinologists, and even psychiatrists all told her they couldn’t see a reason for her pain; it was probably just stress, they said. 

At age 29, after a year in Boston focused on her health, Said accepted the fact that she needed to find a way to move forward. Pain and suffering, she came to conclude, were not one and the same, and she refused to let pain define her. She decided to return to the business world and created a plan to network all over Boston. Although her job search was significantly challenged by the 2008 financial crisis, which had frozen Boston’s traditional investment jobs, she eventually found her way into the city’s booming biotech industry.

She secured a position at a biotech family office. Over the next four years she helped launch their biotech fund, and was responsible for building its U.S. venture capital group and digital health strategy. At 33, she helped launch a growth equity fund.

“Although I took a pay cut to get that job, that was the first time I felt I was finally on my way to achieving true financial independence,” Said said. “I was learning that sometimes if I’m patient enough, the exact right thing presents itself. But at that point, I was still waiting for horses to come back in my life.”

“I was learning that sometimes if I’m patient enough, the exact right thing presents itself. But at that point, I was still waiting for horses to come back in my life.”

Sasha Said

In 2019 she joined LetsGetChecked, a company she had invested in because she strongly believed that at-home diagnostics would play a huge role in making health care more accessible for all patients. She was leading the company’s commercial team when the coronavirus pandemic hit, and overnight the company’s test became a necessity for industries, health care professionals and patients everywhere. 

But her pain was growing worse than ever before, and she struggled sometimes even to sleep or breathe. So she called in a work favor and eventually ended up seeing Dr. Dean Donahue, who—after nine months of specialized diagnostics—diagnosed her with thoracic outlet syndrome, a condition where compression of the blood vessels and nerves between the neck and shoulder causes a variety of muscle pains and weaknesses.

She’d need a series of major surgeries, she learned, to make space in the thoracic outlet: Surgeons would remove two muscles on each side of her neck, her first ribs, both attachments to her pec minor, and part of her C7 transverse process in a vertebrae in her neck.

All surgery comes with risk, and Said was understandably anxious. She began reading and researching about the procedure and recovery. One source suggested meditating on what you believe is your life’s greater purpose before going in to surgery.

Despite being out of the saddle for over two decades at that point, horses were the first thing that came to mind.

“I’d put this block in my brain that I don’t have money or time to ride,” she said. “But it’s what I’d been working toward my whole life.”

“I’d put this block in my brain that I don’t have money or time to ride. But it’s what I’d been working toward my whole life.”

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Sasha Said

She made a promise to herself: If I survive this surgery, I’m going to ride.

So she researched barns in her area and eventually set up a visit Orchard Hill Equestrian Center, where trainer Caroline Teich ran an eventing program. Said’s surgeries were successful, and after almost a year of recovery, she was ready to schedule her first lesson at Orchard Hill.

“Caroline had me start on a Thoroughbred named Smartie, and I fell in love with him immediately,” she said. “He was 23, but he loved to go. He brought me back to riding, and I still tear up thinking about him.”

Because of her increased strength and body control post-surgery, she felt like a stronger and more effective rider in her early 40s than she had been in her teens.

After six months, Said was ready to take on novice, and it was time to move on from Smartie. Said didn’t want to let him go, but a horse named I DunNo was coming up for lease, and Teich thought they’d be a good match. 

Said wasn’t sold on dun “Dudley” right away. At 40, and having recently undergone two major surgeries, she didn’t want to get hurt. And Dudley was spooky.

But she decided to give him a chance, and that first winter, Said took Dudley to Florida with her trainer. They took it slow, getting to know each other, and Dudley learned to trust his new rider.

“Over time I recognized the potential beneath his fear,” Said said. “He wasn’t genuinely naughty, just legitimately afraid of everything. I like to think I had the right amount of empathy and compassion to work through his fears and be his source of confidence.”

Within their first year together, they were competing at training level. By the next year, they advanced to modified—an achievement no one expected from Dudley.

“We’ve had tremendous success together, but there were steps forward and steps back,” Said said. “It took time to figure out his quirks. He threw me so many times, but thankfully an air vest is like landing on a cloud!”

In the winter of 2025, Dudley needed some time off; their Florida season was over before it started. He’s expected to come back to full work soon, but his owner, who recently graduated from college, is ready to sell him. And while Said loves him dearly, she has dreams that are bigger than what’s fair to ask Dudley to do.

“Our last show together was Waredaca in October, and we couldn’t have ended on a higher note,” Said said of the Waredaca Classic Three-Day Event (Maryland), which offers beginner novice through preliminary level horses and riders a rare opportunity to compete in a traditional long-format three-day event, including dressage, roads and tracks, cross-country and show jumping—and two formal horse inspections. “Those modified cross-country jumps were the most challenging we’ve faced, and he ate them up. I’m bonded to this horse for life, and I’m so thankful for that.”

The pair also earned a special long-format accolade: best dressed at the horse inspection. Said had Dudley groomed so his dun coat shone like precious metal, and herself wore a beautiful Indian kurta for the jog.

“Representation matters,” she said. “And I feel strongly that there’s not enough diversity in the horse world. Having my cousin and my mom there to see me ride for the first time ever while honoring our shared heritage was particularly meaningful.”