What Makes a Family Business Last Across Generations | The Family Biz Show Ep. 125

What Makes a Family Business Last Across Generations

Episode 125 of The Family Biz Show delivers one of the most grounded and insightful family business leadership stories in recent memory. Hosted by Michael Palumbos, a seasoned financial advisor for family business owners, this episode features Domenic Cortese of Cortese Construction Services—a second-generation leader actively transitioning a thriving company to the third generation.

Through honest family business conversations, this episode explores the real mechanics behind longevity: trust, governance, wealth discipline, and intentional succession. These are not theoretical lessons. They are lived leadership legacy stories that show what it truly takes to move a family business to new generation leadership without breaking relationships or momentum.

Immigrant Roots and the Foundation of Trust

The Cortese story begins in the early 1950s when Domenic's father and uncle immigrated from Italy and built a construction company from nothing. Their partnership was rooted in deep family enterprise relationships, marked by absolute trust—even when conflict was present. Their dynamic illustrates a critical truth often discussed by any experienced family business advisor: trust does not require harmony, but it does require commitment.

These early family enterprise stories laid the groundwork for a business that would survive multiple transitions. Yet, as Domenic explains, the same trust that fueled growth also created governance challenges—highlighting why family governance and trust must evolve as businesses grow.

Succession Is About Choice, Not Obligation

One of the most impactful family business conversations in the episode centers on Domenic's cousin, who never wanted to be in the business. Rather than forcing participation, Domenic sought outside guidance from a family business succession planning advisor, creating a dignified exit that preserved both family harmony and business health.

This moment underscores why family business legacy planning is inseparable from personal fulfillment. A strong family business advisor understands that continuity fails when individuals feel trapped. Addressing family dynamics in succession early is one of the most effective forms of family business continuity planning.

Architecting a Family Enterprise That Can Adapt

When Domenic assumed leadership, he didn't simply inherit the business—he rebuilt it. By exiting seasonal concrete work and expanding into remodeling, he demonstrated thoughtful family business strategy rooted in core competencies. This approach to architecting a family enterprise allowed the company to maintain family enterprise momentum without reckless risk.

Rather than chasing growth, Domenic focused on designing family business continuity, proving that sustainable scale comes from discipline. This mindset mirrors how sophisticated family business family office structures think about long-term enterprise value.

Letting Go of Control to Build Real Leadership

A defining theme in this episode is Domenic's decision to move away from founder-centric control. Learning to trust non-family leaders became essential to sustaining momentum in family business operations. Today, key non-family roles support quality, operations, and growth—demonstrating how trust in family business extends beyond bloodlines.

This shift reflects best practices in family office explained frameworks, where governance systems protect culture while empowering professionals. Any family business family office advice worth following emphasizes this balance.

Preparing the Family Business for the New Generation

Now transitioning ownership to his three children, Domenic offers a real-world case study in multi-generational continuity. Equal ownership, clear expectations, and accountability—such as shared liability for company assets—reinforce mature family enterprise relationships.

Domenic's focus on separating sibling roles from business roles directly addresses common family business trust issues. These intentional structures support family business continuity strategy and reduce emotional decision-making, a lesson any family business succession planning advisor would endorse.

Wealth Discipline and the Family Office Mindset

Throughout the episode, Michael Palumbos—speaking from his experience as a financial advisor for family business owners—highlights the importance of separating personal wealth from business dependency. Domenic's disciplined approach to family business wealth management, including real estate investing and gifting strategies, reflects a true family business family office mindset.

This approach ensures founders can step back without fear, a cornerstone of effective family business wealth management advisor guidance and long-term family office legacy planning.

Grandchildren, Values, and Legacy Beyond the Balance Sheet

Looking ahead, Domenic emphasizes preparing grandchildren through earned responsibility, humility, and philanthropy. These practices reinforce legacy continuity planning and sustain family business momentum across generations.

By introducing philanthropy early, the Cortese family uses values as a training ground for leadership—an often overlooked yet powerful aspect of family enterprise stories that truly last.

Why This Episode Matters

Episode 125 stands out because it connects governance, wealth, and relationships into one cohesive narrative. It offers clarity on family business legacy planning, real insight into family enterprise relationships, and practical guidance from both a business owner and a trusted family business advisor perspective.

For anyone navigating succession, governance, or wealth transitions, this episode explains—clearly and honestly—what makes a family business last across generations.