From Founder to Exit: How Each Generation Builds and Sells a Business Differently with Peter Cifichiello

From Founder to Exit: How Each Generation Builds and Sells a Business Differently with Peter Cifichiello

In this episode, Jon Sheppard sits down with Peter Cifichiello, Partner at Casner & Edwards, LLP, to explore how different generations build, grow and ultimately exit businesses. Together, they examine why succession planning is about far more than legal documents or financial transactions. It's about understanding the people behind the decisions. Drawing from his extensive experience advising founders, family businesses and closely held companies, Peter shares how each generation approaches entrepreneurship, leadership, risk and long-term planning through a different lens. The conversation explores how life stage influences decision-making, why founders often struggle to transition leadership and how generational perspectives can either create friction or become a strategic advantage. Jon and Peter also discuss business succession, founder identity, organizational evolution, communication and the importance of aligning family, leadership, and ownership goals. Whether you're building a company, preparing for an exit, or helping guide the next generation of leaders, this episode offers practical insights into navigating change with intention.

The Human Side of Legal Work: Parenthood, Identity and Professional Growth with Nicole Suriano

In this episode of The Generationality of Work, Jon Sheppard welcomes Nicole Suriano (Leydon), Paralegal at Brandon J. Broderick, Attorney at Law, for a thoughtful conversation about parenthood, professional identity, workplace culture and personal growth in today's legal profession. Nicole shares her perspective on balancing career development with family life while navigating the evolving expectations of a multigenerational workforce. Together, she and Jon explore how leadership, emotional intelligence, flexibility, accountability and authenticity influence employee engagement and organizational success. Listeners will gain practical insights into leadership, workplace culture, employee engagement, burnout prevention, generational expectations and the human side of professional growth in modern organizations.

The Myth of Succession: Why Most Family Firms Drift and Don’t Actually Transition with Marc Landow

In this episode of The Generationality of Work, Jon Sheppard sits down with Marc Landow, Partner at Landow and Landow Architects, to explore the realities of succession planning inside a family business that has successfully operated for more than a century and is now in its third generation. Together, they examine why succession is often misunderstood and why many family firms drift rather than intentionally transition leadership from one generation to the next. Marc shares personal reflections on growing up within a successful family business and the responsibility that comes with inheriting opportunities created by previous generations. The conversation explores leadership, accountability, credibility and the importance of earning trust regardless of title or family connection. Marc discusses how intentionality, work ethic and leading by example have shaped his approach throughout a 30-year career, while also highlighting the challenges family businesses face in balancing legacy with adaptation. Listeners will gain valuable insights into succession planning, multi-generational leadership, organizational culture and what it truly takes to build a business that lasts across generations.

Multigenerational Client Service Teams - How Generational Diversity Strengthens or Fractures Client Service Outcomes with Michael Kaufman

In this episode of The Generationality of Work, Jon Sheppard sits down with Mike Kaufman, Partner at Kaufman Organization, to explore how multi-generational client service teams can either strengthen or challenge business outcomes. Drawing on decades of experience in New York real estate, Mike shares his perspective on how different generations approach decision-making, risk and client service. The conversation highlights the contrast between traditional, process-driven industries and newer, more creative and fast-moving sectors such as technology and AI. Younger professionals often bring innovative ideas, energy and access to capital, while more experienced professionals contribute critical judgment, industry knowledge and an understanding of long-term consequences. This episode underscores the importance of bridging generational gaps within client service teams. When organizations successfully integrate innovation with experience, they position themselves to deliver stronger outcomes, better manage risk and create lasting client relationships. The discussion reinforces that generational diversity is not a challenge to overcome, but a strategic advantage to be harnessed.

Compensation, Transparency & Fairness - Why Compensation Silence Breeds Mistrust and How Transparency Builds Confidence with Mark Shore

In this episode of The Generationality of Work, Jon Sheppard is joined by Mark Shore, President of Atlas Consulting Services, to explore the evolving role of compensation in today’s workplace. The conversation goes beyond salary to examine how compensation, including benefits, serves as a reflection of an organization’s values, priorities and overall culture. Mark shares insights on why forward-thinking firms are treating compensation as a strategic tool rather than a transactional necessity. He discusses how a lack of structure, communication and leadership alignment around compensation can lead to confusion and mistrust, particularly in multi-generational work environments where expectations and perspectives vary widely. The episode also highlights the critical role leadership plays in designing and supporting compensation strategies, rather than leaving them solely to HR to implement. Ultimately, this discussion underscores that transparency and intentionality in compensation are key drivers of trust, engagement and long-term organizational success.