Joby Holland

Raised in rural Southeast Missouri, Joby developed a passion for the outdoors
at an early age. Whether working alongside his father farming, hunting,
fishing, he learned the values of hard work, conservation, and respect for
nature. Those early experiences created a lifelong appreciation for wildlife
and the outdoors that continue to shape his personal and professional life.

Before his time with Open Season Properties, Joby dedicated 32 years to
public education, including 27 years as a school administrator and 17 years as
a superintendent. He also spent a decade coaching high school basketball,
mentoring young athletes and developing future leaders. He holds a
Doctorate in Educational Leadership from Saint Louis University.

Outside of his education career, Joby’s true passion has always been hunting
and the outdoors. For decades, he has hunted whitetail deer and turkey
throughout the Midwest while gaining extensive hands-on experience
managing habitat, developing food plots, evaluating recreational properties,
and improving land for wildlife.

That experience naturally led him to Open Season Properties, where he
combines his passion for the outdoors with a lifelong commitment to serving
others. As a licensed Missouri real estate agent specializing in hunting,
recreational, farm, and rural properties, he understands that buying or selling
land is about much more than acreage—it’s about investing in a lifestyle,
protecting an investment, and creating a legacy.

His connection to the land is deeply personal. His great-great-grandfather
settled 160 acres in Ripley County, Missouri, and that farm remained in the
Holland family for more than a century. That heritage gave him a lasting
appreciation for the memories, traditions, and opportunities that land creates
for generations.

Whether helping buyers find the perfect hunting property, farm, recreational
retreat or assisting landowners in maximizing their property’s value, Joby is
committed to providing honest guidance, clear communication, and
exceptional service, while building lasting relationships based on trust and
positive results. His goal is to make every buying, selling, or investing
experience successful, seamless, and rewarding.