In this episode, James Kennedy sits down with Neil Geary, fractional CFO and partner at SeatonHill Partners, to unpack what happens when big entrepreneurial vision meets real-world financial reality. Drawing on a career that started as a Coast Guard - licensed boat captain and evolved through family offices, hospitality, and large-scale real estate development, Neil shares how “captain’s thinking” - planning, diligence, and safety - translates into better decisions for founders and investors.

From rescuing a beloved but loss-making New England “trophy” hotel and restaurant, to helping a Midwestern multifamily developer level up into a $67M ground-up project, Neil shows how the right CFO can turn chaos into a clear course - without killing the entrepreneurial spark that made the business work in the first place.