Fifty Years of Living It: James Roland

Dean Castelhano sits down with longtime friend and business leader James Roland at 2nd Floor Studios for a conversation on grit, family legacy, and making the leap from big business to small business. From starting out at New York Life to becoming a Rockwall home builder, James shares five decades of lessons in relationships, problem-solving, and passion for the work.

This episode of Small Business, Living It isn’t about quick wins or financial shortcuts — it’s about the people and principles that make success sustainable. James talks about honoring family history, navigating capital markets from both sides of the table, and why retirement doesn’t appeal when you truly love what you do.