Jake Michalson

I spent over 20 years in transportation, logistics, towing, and vehicle operations, so I bring a firsthand understanding of the risks business owners face every day. I focus on insurance solutions for high-liability and recreational businesses, with attention to detail, accountability, and the ability to problem-solve under pressure.

My background in fleet safety, equipment handling, and regulatory compliance gives me a practical perspective on liability and operational risk. That experience combined with 50 years of insurance knowledge at Leavitt Recreation and Hospitality means I know how to build long-term relationships and provide dependable guidance tailored to each client’s needs.

I grew up in Sturgis, South Dakota, and still value the hardworking, community-minded spirit of this area. Outside of work, I enjoy rebuilding cars, hunting, fishing, trap shooting, cross-fit, and spending time with my wife and three children.