I developed a friendship with Bob Brennan while we were serving time together at the federal prison in Fort Dix, New Jersey. By then, I had already been incarcerated for 14 years, and Bob had recently transferred to Fort Dix. From our first encounter, it was clear that he didn’t fit the typical prison mold. He exuded an aura of leadership that was rare in such an environment.
Bob’s background was extraordinary. He had been the founder and CEO of several companies, including First Jersey Securities. His real-world experience in building businesses and leading teams intrigued me, and I knew I could learn a great deal from him. For someone like me, who had spent his entire adult life in prison, the opportunity to gain insights from a successful business leader was invaluable.
Over the years, I had read numerous biographies of influential figures and business leaders. Books like The House of Morgan, The Road Ahead, and Titan offered me theoretical insights into how the world of business worked. But spending time with Bob allowed me to bridge theory with practical wisdom. Through our conversations, I gained a deeper understanding of the CEO mindset, including how to value companies, develop strategies, and work toward clearly defined goals.
Bob and I collaborated on several writing projects. His candor and constructive feedback helped me improve as an author. He taught me lessons on focus, resilience, and the importance of setting measurable objectives—skills that were essential for someone preparing to reintegrate into society after years of incarceration.
When Carole entered my life, Bob played a significant role in supporting us. We coordinated our visiting schedules so that I could introduce her to him. Although Bob couldn’t attend our wedding, which was presided over by the local mayor in the prison’s visiting room, he made a thoughtful gesture. He reached out to a friend and asked him to do something special for Carole. Neither Carole nor I knew this friend, yet Bob’s friend arranged for a courier to deliver an envelope containing $2,000—an incredible act of generosity and goodwill that remains deeply appreciated.
In 2024, I had the privilege of reconnecting with Bob during a visit to Florida, and I look forward to seeing him again. He has since published a memoir titled Brennan: The Record Stands, which I highly recommend. The book details his remarkable life, from building major businesses to cultivating friendships with some of the world’s most powerful figures, including Presidents, Popes, and CEOs of global companies.
Prison is a microcosm of the world. During the 26 years I served, I encountered many individuals to avoid, but I also found people who accelerated my learning and preparation for success upon release. Bob Brennan is one of those people, and I am profoundly grateful for his friendship and mentorship.
Self-Directed Learning Question:
- “Who in your environment can inspire or guide you, and how can you build a meaningful relationship that accelerates your growth?”
