About

Jessup’s journey has been shaped by faith, personal drive, and a passion for charting his own path. Growing up in a small Kansas town, he was surrounded by hard-working people who showed up every day, and worked with pride. Those early lessons instilled a deep respect for effort, integrity, and drive. By the age of sixteen, his work ethic had already set him apart, earning him a full-time management role at a fast-food chain and putting him on track to run his own store. Had his parents not talked him out of it, Jessup likely would have taken the offer. Instead, he stepped into a season of exploration, balancing college, service in the National Guard, and work at a national retailer while quietly trying to determine where his path would take him.

One day, a chance meeting changed the course of Jessup’s life forever. Two businessmen came to his job to shop, but seeing Jessup’s drive, they offered him a career in finance. Jessup accepted the offer and spent the next eight years not only discovering the world of finance and how to serve his clients best, but also discovering his own value, purpose, and path. When Jessup entered the financial industry, he saw an opportunity to guide people through some of the most important decisions of their lives. He learned the business thoroughly, built strong relationships, and became a trusted leader within an established firm. Though the next step into leadership made sense to some, Jessup, through faith and self-reflection, came to a defining realization: fulfillment does not come from titles or inevitability, but from obedience to purpose. He chose to step away and forge a path of independence, where he could truly control his own life and help his community do the same.

Leaving the established path and founding Waymaker Legacy allowed Jessup to step fully into independence, serve clients with clarity and conviction, and lead in a way that honors his faith, his family, and his purpose. Jessup brings experience, discipline, and integrity into every client relationship, helping families protect what they’ve built and move forward without fear.

Raised in a small Kansas town where hard work and integrity were a way of life, Jessup’s journey has been driven by faith, discipline, and a desire to chart his own path. After an early start in leadership and a season balancing college, the National Guard, and working full time, a chance meeting with two businessmen opened the door to a career in finance—one that shaped his purpose over the next eight years. Though success and advancement were within reach, Jessup realized true fulfillment comes from obedience to purpose, not titles, and chose independence over the expected route. Today, through Waymaker Legacy, he serves families with clarity and conviction, helping them protect what they’ve built and move forward without fear.