What Makes a Family Business Last Across Generations

What actually makes a family business survive across generations?

For Domenic Cortese of Cortese Construction Services, it was never just about revenue growth or expanding operations. It was about building a culture strong enough to outlast the founders, preparing the next generation without entitlement, and creating systems that preserved both family relationships and business continuity.

In this episode, Domenic shares the remarkable story of how his father and uncle immigrated from Italy with nothing, built a concrete business from scratch, and created a foundation that would eventually evolve into a thriving second- and third-generation construction company. He opens up about the difficult lessons learned from working inside a family business, the dangers of forcing succession, and how gifting ownership, leadership development, and open communication helped position the company for long-term success.

Michael and Domenic also discuss sibling ownership dynamics, preparing grandchildren for stewardship, avoiding founder bottlenecks, and why many family businesses fail when entitlement replaces earned responsibility. This conversation offers practical insights for family business owners, next-generation leaders, and advisors focused on preserving both legacy and relationships.

Succession Planning Next Generation Leadership

“When they’re in this building, their first connection with their brother and sister is business partner… not sibling.”

Domenic Cortese

Key Takeaways

➜ A lasting family business requires earned responsibility, not entitlement.
Domenic emphasizes that every generation must earn its place inside the company. Starting at the bottom helps family members develop humility, credibility, and respect for the business.

➜ Succession planning works best when family members choose the business willingly.
One of the biggest turning points in the company’s history came when Domenic helped his cousin exit the business rather than forcing continuation. Preserving relationships mattered more than preserving ownership structure.

➜ Founder mentality can limit long-term growth.
Domenic learned that trying to do everything himself nearly burned him out. Building leadership teams and trusting specialists became essential for scaling the business beyond the founder bottleneck.

➜ Family communication becomes more complex with sibling ownership.
As the third generation stepped into leadership, Domenic noticed how quickly siblings can blur the line between family roles and business roles. Clear communication and governance became critical.

➜ Preparing future generations starts long before ownership transfer.
The Cortese family intentionally introduces grandchildren to work ethic, stewardship, and accountability at a young age. Their philosophy focuses on contribution before privilege.

Guests Appearing in this Episode

Domenic Cortese
Second-generation leader of Cortese Construction Services, Domenic Cortese helped transform his family’s construction company into a thriving multi-generational business while preparing the third generation for leadership and ownership.