Racetrack – Harnessing Your Wealth

From Jockey to Top Trainer: Jason Olmstead’s Winning Formula (EP. 70)

By Harnessing-Your-Wealth | December 16, 2025

In this exciting 70th episode of Harnessing Your Wealth, host Billy Peterson interviews Jason Olmstead, a prominent horse trainer. Jason Olmstead grew up surrounded by horse racing, with his grandparents training racehorses. His family’s roots in the industry laid the foundation for his future career. “I fell in love with it from day one,” Jason recalls, reflecting on his childhood. Jason shares insights on training philosophies, the significance of soundness in horses, and the loyalty of quarter horse owners. Jason’s training career has been marked by impressive achievements. His ability to maintain long-term relationships with clients has been a key factor in his success. “What I’m most proud of is we still train for a lot of the same people that we originally trained for that gave us our first chances,” he shares. This loyalty and dedication to his clients and their horses have fostered a supportive community around his training stable.

Takeaways

Harnessing Your Wealth is about more than just money.
Jason Olmsted’s journey in horse racing began with his grandparents.
The importance of family support in a racing career.
Quarter horses often have more loyal owners than thoroughbreds.
Building relationships with riders is key to a successful stable.
Learning from mistakes is part of the training process.
Fear of failure can drive success in competitive environments.
The next generation of riders is essential for the future of racing.

About our Guest:

After a successful career as a jockey, Jason transitioned to training, a move that seemed almost inevitable. Jason Olmstead and his wife Amber own Circle JA Racing Ranch in Pryor, Okla. He had the most Quarter Horse wins of any trainer here in 2023. Jason grew up in horse racing. His grandfather was a trainer and all he ever wanted to do was be a jockey. He has the honor of winning the AQHA Racing’s 2021 Blane Schvaneveldt Champion Trainer award. Jason and Amber Olmstead are among the Class of 2022 inductees into the Canterbury Park Hall of Fame.

More about Jason Olmstead:

Resources & Previous Episodes of Interest:

Connect with Billy Peterson:

Connect with Cade Peterson:

Connect with Shaun Peterson:

Peterson Wealth Services: Shaun Peterson
LinkedIn: Shaun Peterson
shaun@petersonws.com
801-475-4002

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From the Racetrack to Business Owner with Kip Didericksen (Ep. 19)

By Harnessing-Your-Wealth | September 19, 2023

Few journeys are as exhilarating and transformative as those of a jockey.

The rush of adrenaline during races and the intricate partnership between humans and horses all come together to tell a story of talent, perseverance, and passion.

In this episode, Kip Didericksen, a renowned former jockey shares his journey from the race tracks to being a business owner, highlighting how the value of hard work and strategy contributed to his success. He also talks about memorable horses and people, and the races that taught him valuable lessons.

Kip discusses:

His childhood as a member of a racehorse family and how he idolized jockeys
The talent level and competition among jockeys at Los Alamitos
His standout horses and the trainers who supported him
A look back at his most successful season when he was the leading rider and won multiple races
His experience of being treated poorly by a fellow jockey and how it motivated him to always help others
And more!