Founders

Caldwell Heritage was founded by Jim and Jamie Caldwell with a shared belief that businesses and real estate should be owned with a long-term perspective — not built for a quick exit, but stewarded with care for future generations.

Together, they established Caldwell Heritage as a family holding company focused on acquiring, operating, and investing in exceptional businesses and real estate throughout Florida. Their vision is rooted in stewardship, integrity, disciplined decision-making, and creating enduring value for employees, customers, business partners, and the communities they serve.

Jim brings more than 30 years of experience in construction, facilities management, operations, and entrepreneurship. Throughout his career, he has built and operated service businesses, led construction and facilities organizations across large multi-state portfolios, and developed extensive expertise in the trades, real estate, acquisitions, and business operations. He holds a Master's degree in Organizational Leadership and an MBA with a concentration in Real Estate.

Jamie has been an integral part of the Caldwell Heritage journey from the beginning. She previously worked in the roofing industry and helped build and operate the family's earlier business, gaining firsthand experience in customer service, administration, and the day-to-day realities of running a growing company. After the birth of their children, she chose to devote herself full-time to raising and homeschooling their children, cultivating faith, character, responsibility, and a strong work ethic — principles that continue to shape the culture and long-term vision of Caldwell Heritage.

Beyond her work with Caldwell Heritage and raising their children, Jamie also serves on the board of Girls With Confidence, a nonprofit organization dedicated to building confidence and character in girls and boys. Her service reflects the Caldwell family's belief that investing in people and strengthening communities is just as important as building successful businesses.

Together, Jim and Jamie believe that successful businesses are built on trust, lasting relationships, disciplined stewardship, and a genuine commitment to serving others. Rather than pursuing rapid growth at any cost, Caldwell Heritage seeks opportunities where thoughtful ownership, operational excellence, and long-term investment can create value that endures for decades.

Their vision is to build a family enterprise that will serve communities, provide meaningful opportunities for others, and remain a source of strength and stewardship for generations to come.