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In this special 100th episode of Take It To The Board, we’re excited to welcome back our very first guest, James Donnelly. When host Donna DiMaggio Berger first sat down with James in 2021, he was leading Castle Group, one of Florida’s largest community association management firms. Now, they reunite to reflect on the extraordinary journey James has taken since selling the company. Together, they explore the motivations behind his decision, the carefully crafted four-year succession plan that ensured Castle’s continued success, and the passion projects that are now shaping his next chapter.

Throughout the episode, James and Donna dive deep into the realities of the acquisition process, offering insights that business owners and industry leaders alike will find invaluable. They discuss the advantages of planning a sale from a position of strength and the importance of developing a leadership team that can thrive independently. Their conversation also examines how the association management industry has evolved—especially in response to the challenges posed by COVID-19 and the Surfside tragedy.

Despite growing consolidation in the industry, James and Donna share an optimistic outlook on opportunities for entrepreneurs. They note that no single company has captured more than a small share of the market, leaving ample room for innovation and growth. They also discuss James’s investment in the future of the field through the James Donnelly Property Management program at Nova Southeastern University, a “farm system” designed to cultivate new talent.

The episode concludes with a meaningful discussion about the personal values that guide James’s life—stretch, smile, live, and give—a daily mantra that he uses to balance his ongoing industry involvement, philanthropy, and upcoming book on life principles. With warmth, insight, and mutual admiration, James and Donna deliver a compelling conversation that celebrates past accomplishments while looking forward to the future, making this milestone episode both thought-provoking and deeply inspiring.

Conversation Highlights:

• The increasing complexity of the community association industry in the wake of COVID-19, the Surfside tragedy, and new legislation
• Key challenges and growth opportunities facing the industry today
• The most unexpected part of Castle Group’s sale process
• James’s practical advice for business owners thinking about selling
• Insights for leaders weighing whether to remain active or begin stepping back
• The passion projects and new ventures James is currently pursuing

Related Links:

• Podcast: Royal Service with James Donnelly, Founder & CEO, Castle Group