Thoroughbred Horse breed – 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.

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Connect with Shaun Peterson:

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

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The Thrill of the Race: Insights from Andrew Offerman (Ep. 56)

By Harnessing-Your-Wealth | June 4, 2025

Billy Peterson and Cade Peterson discuss the current state of horse racing with Andrew Offerman, Senior Vice President of Racing at the New York Racing Association. They discuss the excitement surrounding major races like the Belmont Stakes, the challenges of hosting events at alternate venues, and the importance of engaging younger audiences through influencers and educational initiatives. The discussion also touches on the emotional highs and lows of racing, the economic impact of the industry, and the need for transparency and integrity in the sport. Andrew shares insights on how to get involved in horse racing, whether as a fan or an owner, and the efforts being made to simplify betting for newcomers.

Takeaways

The Belmont Stakes is a significant event with a unique history.
Hosting major races at alternate venues presents challenges.
Horse racing is experiencing a resurgence in popularity.
Influencers can attract a new audience to the sport.
Every race win is a special experience for participants.
Youth engagement is crucial for the future of racing.
The economic impact of horse racing is substantial.
Transparency and integrity in racing are essential.
There are various pathways to get involved in horse racing.

About our Guest:

Andrew Offerman | SVP, Racing and Operations

As Senior Vice President of Racing and Operations, Andrew Offerman is responsible for the leadership and oversight of racing functions at NYRA including the development, planning, and execution of NYRA’s stakes program, marquee events and live racing offerings at Aqueduct Racetrack, Saratoga Race Course and, when complete, the new Belmont Park. Additionally, he oversees several of NYRA’s general frontside operating departments including mutuels, parking, programs, security and cleaning.Prior to NYRA, Offerman served as Senior Vice President of Racing Operations at Canterbury Park in Shakopee, Minnesota. In this role, he was responsible for the direct oversight of Canterbury’s racing office, wagering, track maintenance, security and other operational departments supporting live and simulcast racing operations. Offerman holds an advisory and governance position with the University of Arizona Race Track Industry Program (RTIP) Advisory Committee and previously served in similar capacities with the Thoroughbred Racing Associations of North America (TRA); American Quarter Horse Association (AQHA) Racing Committee, and the Thoroughbred & Quarter Horse Breeders’ Fund Advisory Committees of the Minnesota Racing Commission. A native of Minneapolis, Offerman earned an M.S. degree from the University of Arizona Race Track Industry Program (RTIP) and holds a B.A. from Gustavus Adolphus College.

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NYRA: Andrew Offerman