55 - Aging Brilliantly: Redefining Work and Legacy in Family Enterprises
Navigating Growth, Leadership, and Legacy in Family Business: Insights from Jerry Cahn of Vistage Worldwide
In this episode of the Growing Up B2B Podcast, host Ed Delia speaks with Jerry Cahn, Vistage Chair, Strategist, and Mentor at Vistage Worldwide, Inc., about the evolution of leadership, succession, and purpose in modern family businesses. Drawing from his background in psychology, law, and entrepreneurship, Jerry shares timeless lessons on aligning values, embracing external perspectives, and redefining what legacy means in a world where leaders are living—and contributing—longer than ever. This episode offers actionable insights for founders, next-generation leaders, and executives dedicated to leading with both strategy and heart.
Leading with Perspective: Experience, Legacy, and Lifelong Impact
Jerry’s career path is a masterclass in multidimensional leadership. From his early work in psychology and healthcare policy to running corporate wellness programs and tech ventures, each phase shaped his understanding of how people, systems, and strategy intersect. As a Vistage Chair, he now helps CEOs and executives think beyond their company’s bottom line—focusing instead on purpose, sustainability, and the personal growth that fuels effective leadership. His philosophy centers on “age brilliance,” the idea that leaders should continue contributing meaningfully well into their later years, redefining retirement as renewal rather than retreat.
One of Jerry’s core messages for family businesses is the importance of outside perspectives. Too often, legacy companies rely solely on internal experience, which can limit innovation and self-awareness. Through peer advisory groups like Vistage, leaders gain the rare opportunity to receive candid feedback and challenge their assumptions in a judgment-free environment. Jerry also emphasizes that observing team interactions—rather than simply listening—can reveal deeper patterns that unlock growth. This reflective approach helps family-run organizations navigate emotional dynamics while maintaining professionalism and shared purpose.
Finally, Jerry advocates for long-term adaptability and open dialogue about succession. He encourages leaders to move beyond rigid retirement timelines and outdated hierarchies, instead cultivating mentorship, transparency, and lifelong engagement. By integrating personal development with business planning, leaders can strengthen not only their companies—but the generations that follow.
About Jerry Cahn
Jerry Cahn is a seasoned strategist, psychologist, and educator serving as a Vistage Chair, Mentor, and CEO Advisor at Vistage Worldwide, Inc.. With a Ph.D. in psychology and a J.D. in law, Jerry combines human insight with strategic acumen to help leaders achieve both personal and organizational growth. Through his work with Vistage and his Age Brilliantly initiative, he empowers executives to expand their leadership impact, rethink retirement, and build legacies grounded in purpose, balance, and lifelong learning. Connect with him on LinkedIn.
About Vistage Worldwide, Inc.
Vistage Worldwide, Inc. is the world’s leading CEO peer advisory organization, helping business leaders make better decisions, achieve better results, and lead more fulfilling lives. With a global network of over 45,000 members, Vistage provides confidential peer groups, expert coaching, and thought leadership that drive professional and personal growth for leaders across industries.
Links Mentioned in This Episode
Key Episode Highlights
The power of diverse experience in shaping visionary leadership
Why family businesses thrive when they invite external perspective
How to challenge inherited assumptions that limit innovation and growth
Redefining aging, retirement, and legacy for modern leaders
Practical steps to build a values-driven, future-ready organization
Conclusion
In this episode of the Growing Up B2B Podcast, Jerry Cahn reminds leaders that growth and legacy are deeply intertwined. By combining diverse experiences, seeking objective feedback, and redefining what it means to lead across generations, family business executives can ensure their impact extends far beyond their tenure. True success, as Jerry notes, comes from aligning personal purpose with organizational vision—creating a legacy that evolves, inspires, and endures.
Explore Ed Delia’s website to learn more about leadership strategies for family businesses and B2B growth. If you’re a B2B leader with insights to share, apply to be a guest on the Growing Up B2B Podcast here.
