OTTB on Tap

In this RRP Trainer Chronicles update from OTTB on Tap, we sit down again with dressage trainer Harley Whittaker of HW Dressage in Kirkwood, Pennsylvania to hear the latest on her 2025 RRP Makeover partner, Juancho (“Jack”). Harley shares the ups and downs of Jack’s first dressage show experience, why she’s choosing to keep him in dressage as his primary discipline, and what kind of home she sees for him after the Makeover.

Beyond Jack’s journey, Harley gives us an inside look at her training business, the horses currently in her barn, and even a recent appearance she made on JJ Tate’s podcast. She offers a practical training tip for green horses and OTTBs—breaking down how she adjusts her approach between Jack, a Thoroughbred gelding, and Navy, a young warmblood mare.

We also dive into Harley’s passion for rider fitness, exploring how her six-day-a-week gym routine translates into better feel, empathy, and effectiveness in the saddle. Harley explains how fitness outside the barn supports her students too, and shares advice for riders looking to get started on their own programs.

With the Makeover countdown on, Harley reflects on the biggest lesson Jack has taught her (“expect the unexpected”) and looks ahead to more off-property practice before they head to Kentucky.

Whether you’re an OTTB owner, dressage enthusiast, or rider wanting to balance horse training with personal fitness, this conversation with Harley is packed with insights and inspiration.

In this installment of RRP Trainer Chronicles, an OTTB on Tap Original Series, we catch up with returning trainer Chelsey O’Brien as her 2025 RRP Makeover journey takes shape. This year, Chelsey is retraining two very different OTTBs—each with their own story and style.

✨ Peppy (JC name: The Pepsodent Show) has stepped into the hunter ring, showing the elegance Thoroughbreds can bring to the discipline. His second Makeover division is still undecided, but one thing is certain—he’ll be available for adoption through Pastured Place after the competition, ready to shine in a new home. ✨ Fuzzy Wuzzy, her fiery mare “built like a French Bulldog,” is tackling barrels and ranch work—proving that OTTBs can excel in Western arenas just as much as English ones.

Chelsey opens up about how she decided which disciplines fit each horse, the obstacles they’ve faced along the way, and how she balances her roles as a trainer, breeder, and mom. She also takes us behind the scenes at the Virginia Thoroughbred Association Yearling Futurity, where she proudly presented homebred colts and fillies just a year after foaling them out.

With her philosophy of striving to be 1% better every day, and her belief that training is an art form, Chelsey shares one of her go-to OTTB training tips that listeners can put into practice.

If you love stories of OTTB versatility, retraining insights, and the heart behind the Retired Racehorse Project Makeover, this episode is a must-listen.

We’re back with Stephanie Parkot for round two of her RRP Trainer Chronicles journey—and wow, what a summer she and her OTTB Sterling Honor (by Honor Code, from New Vocations) have had. From tackling a Mounted Police Clinic with her son to braving the atmosphere of the Erie County Fair Hunter/Jumper Show, Stephanie shares the highs, the challenges, and the big takeaways as she and Sterling prepare for the 2025 RRP Makeover.

Noise sensitivity, buddy sour moments, show-ring chaos—Sterling has tested her patience in all the classic OTTB retraining ways. But he’s also shown just how much heart Thoroughbreds bring when given a chance. Stephanie breaks down what’s working, from earplugs to confidence-building hacks, and why figuring out her horse’s “comfort zone” has been such a game-changer.

And remember that mounting block dance from her first episode? That’s now a success story. Stephanie walks us through how she taught Sterling to stand still for mounting—a small detail with huge safety implications for any OTTB rider.

As always, Stephanie keeps it real about balancing family life, motherhood, and horse training, sharing how a supportive husband, a training log, and even a backyard-built water obstacle are helping her get ready for Kentucky. With her trademark “flexible consistency” and a clear focus on progress over perfection, she’s proof that the road to the Makeover is just as rewarding as the event itself.

Photo by Megan Pattern

In Part 2 of our candid conversation with Shannon Riley of Infinity Sport Horse, we go beyond the arena to talk about the challenges many riders face but few openly discuss—body image, online criticism, and the mental health toll of working in the equestrian world. Shannon shares what led her to speak out, how she’s learned to protect her peace, and why creating a healthier, more inclusive space matters for the next generation of professionals.

But it’s not all heavy—Shannon also dives into her practical approach to retraining Off-Track Thoroughbreds. She shares how she transitions OTTBs from track to sport, her go-to groundwork and under-saddle exercises, and how she gauges a horse’s potential as a confidence-builder or upper-level competitor. Whether you’re a rider, trainer, or OTTB fan, her tips are grounded, real-world, and designed to meet horses where they are.

We also explore what mentorship looks like in her program and why she believes her greatest success stories are the riders she’s helped launch into their own careers.

If you’ve ever struggled with confidence in the saddle—or wanted to build a barn culture that values growth over perfection—this episode is for you.

👉 Missed Part 1? Be sure to go back and listen to S2 E31, where Shannon shares her early journey with OTTBs, how she built Infinity Sport Horse, and the personal turning points that shaped her career.

Photo Credit: Liz Crawley Photography 2025

In this episode of OTTB on Tap, we sit down with Shannon Riley of Infinity Sport Horse for Part 1 of a powerful two-part conversation. Based in Aiken, South Carolina, Shannon is a professional eventer, OTTB trainer, and resale specialist known for her thoughtful, honest approach to developing sporthorse prospects.

Shannon shares how her early love of horses—and her first Thoroughbred—set her on a path that would eventually lead to the founding of her training and sales business. From formative experiences with mentors and milestone competitions to the devastating personal loss that pushed her to rebuild her life in Aiken, Shannon reflects on the moments that shaped her as a rider and horsewoman.

She also opens up about her early struggles with imposter syndrome—something both Niamh and Emily can relate to—and the advice she’d give to anyone battling self-doubt while building a career in horses.

We explore Shannon’s deep connection to Off-Track Thoroughbreds: why she’s drawn to retraining OTTBs, what makes them such versatile athletes, and how she evaluates prospects for resale or upper-level competition. Plus, get a behind-the-scenes look at how she runs Infinity Sport Horse and what green flags she looks for when selecting a Thoroughbred for sport.

Whether you’re a first-time OTTB owner, a resale-focused rider, or someone building a training program from the ground up, this episode offers inspiration, real talk, and actionable insight.

👉 Stay tuned for Part 2, where Shannon opens up about rider fitness, body image, online criticism, and how she’s mentoring the next generation of equestrian professionals.

Photo Credit: Liz Crawley Photography 2024

Farrier Jason Hillman CF, based in Chester County, PA, joins OTTB on Tap to tackle one of the most debated topics in Thoroughbred aftercare: hoof health. Jason shares insight into Thoroughbred feet, OTTB hoof care, and the real factors that impact long-term soundness, drawing from his experience working with a large Thoroughbred client base and retraining his own OTTBs.

In addition to being a trusted farrier in the Mid-Atlantic, Jason is also an event rider. He competes his supermare Cruisewithbrandon and is preparing his warhorse gelding Kingsville for the 2025 Retired Racehorse Project Thoroughbred Makeover, where he’ll compete as a team with his mother, June Hillman—a past guest on the podcast and lifelong Thoroughbred advocate.

From radiographs and shoeing cycles to common concerns like thin soles, weak walls, and negative palmar angles, Jason breaks down what matters most when managing OTTB hooves. We also explore modern tools like glue-ons, frog support, wedges, and flat pads—plus when to use them (and when not to).

You’ll hear:

• What to expect post-track and how to set your horse up for success
• Tips for high/low syndrome, moisture management, and fly season
• Why farrier-owner communication is essential—and how to build it
• Listener-submitted questions on PPEs, bell boots, and hoof hacks

Whether you're retraining your first OTTB or working with seasoned sport horses, this episode offers real-world hoof care advice from someone who lives it in and out of the saddle.

Virginia-based trainer Chelsey O’Brien returns to OTTB on Tap as she gears up for the 2025 Retired Racehorse Project Thoroughbred Makeover—this time with two OTTBs and twice the determination. Representing the nonprofit Pastured Place, Chelsey introduces us to The Pepsodent Show (“Peppy”), a charismatic 5-year-old gelding by VE Day. With a name that throws it back to the golden age of radio—The Pepsodent Show was a wildly popular 1930s–40s comedy series hosted by Bob Hope, not unlike today’s podcasts—Peppy brings brains, athleticism, and a big personality to the table.

Chelsey is also retraining her personal mare, Fuzzy Wuzzy, a powerful 4-year-old by Palace, for the barrels and possibly ranch work. In this candid episode, she walks us through how she juggles training two very different OTTBs, her role as a Pastured Place ambassador, and what it means to advocate for Thoroughbred aftercare as both a horsewoman and a mom.

From groundwork and restart strategies to hauling, first shows, and building mental fitness, Chelsey shares thoughtful advice for anyone bringing along an off-track Thoroughbred. She also reflects on how organizations like Pastured Place and The Western Thoroughbred are changing the landscape—making OTTBs more visible and accessible in both English and Western disciplines.

This episode is part of the RRP Trainer Chronicles, an OTTB on Tap Original Series spotlighting the trainers and Thoroughbreds preparing for the Retired Racehorse Project Makeover. Whether you're considering an OTTB for barrel racing, competitive trail, eventing, or the Thoroughbred Makeover, this episode is packed with inspiration and practical takeaways from a trainer who's all heart—and all in.

OTTB on Tap is 100% independently produced by two horse girls who love Thoroughbreds and great storytelling. If you enjoy the show, you can support us through Buy Me a Coffee at buymeacoffee.com/ottbontap. Every bit helps us keep the mics on and the stories flowing. 🐎💛

In this RRP Trainer Chronicles episode of OTTB on Tap, we sit down with adult amateur eventer, longtime Thoroughbred advocate, and sporthorse breeder Amanda Chance, who’s making her Retired Racehorse Project Makeover debut in 2025 with a true warhorse—an off-track Thoroughbred with over 50 starts (he raced a whopping 100 times!)

Known for her candid blog and podcast Breed.Ride.Event., Amanda brings a unique perspective to the OTTB world—combining her eye for conformation with real-world experience restarting Thoroughbreds for second careers in eventing and sporthorse disciplines. She shares what it’s like retraining a seasoned racehorse, how her breeding background shapes her OTTB evaluations, and why she believes more adult amateurs should take the leap into Makeover territory.

We talk about selecting her RRP partner, how his extensive racing career impacts his retraining, and the mental and physical adjustments involved in transitioning a veteran OTTB. Amanda also offers advice for first-time RRP trainers, her favorite sporthorse traits in Thoroughbreds, and how she keeps the journey fun, even when progress stalls.

Whether you're a fellow OTTB owner, eventing enthusiast, adult amateur, or curious about the Thoroughbred Makeover, Amanda’s story is one you won’t want to miss.

Trigger Warning: This episode includes discussion of substance use and mentions of suicide. If these topics are sensitive for you, please listen with care. Resources and support links are included at the end of the episode description.

Ramon Moya didn’t grow up in the saddle—but the first time he sat on a Thoroughbred at 18, everything changed. Now a graded stakes-placed jockey and viral content creator, Ramon has made a name for himself both on the racetrack and online, where his point-of-view body-cam rides and honest behind-the-scenes footage are drawing thousands of new eyes to the world of horse racing.

In this candid, heartfelt interview, Ramon shares what it’s like to ride at speed, cut weight to make race conditions, and build trust with each individual horse he works with. He also opens up about his battle with addiction, getting clean, and his mission to educate others about the realities—and the beauty—of life on the track.

Ramon's passion for Thoroughbreds on and off the track shines through and even though he grinds it out with daily 4am wake up calls, he feels he never works a day in his life while riding.

Whether you’re in it for the Thoroughbreds, the grit, or the humanity, this is an episode that lingers long after listening.

If you or someone you know is struggling, please know you’re not alone.

• National Helpline for Substance Use Disorders (SAMHSA): 1-800-662-HELP (4357) — Free, confidential help 24/7.
• 988 Suicide & Crisis Lifeline: Dial 988 — 24/7 support for anyone in distress.
• PDJF (Permanently Disabled Jockeys Fund): pdjf.org — Support for jockeys, including mental health and addiction recovery services.
• The Jockeys' Guild: jockeysguild.com — Advocacy and wellness support for active and retired jockeys.

Welcome back to RRP Trainer Chronicles, an OTTB on Tap Original Series following the riders and retrainers headed to the 2025 Thoroughbred Makeover. In this episode, we’re talking dressage, Thoroughbreds, and that all-important seat with Harley Whittaker of HW Dressage in Kirkwood, Pennsylvania.

Harley didn’t grow up in a horsey family, but she’s built a thriving training business rooted in thoughtful, individualized care—and a belief that OTTBs absolutely belong in the dressage ring. She introduces us to her Makeover partner Juancho (aka “Jack”), shares what she looks for in a dressage prospect, and walks us through the early days of training a horse fresh off the track.

We chat about visualization, confidence-building, ulcer prevention, and why pulling back is not the answer. Whether you’re new to OTTBs, curious about dressage, or just here to root for a great horse and rider team—you’ll love this candid and inspiring conversation.