Most professionals think high-net-worth clients choose advisors based on credentials, performance, or technical brilliance.

They are wrong.

In this episode, Dave Lorenzo sits down with two of the most trusted dealmakers in the family-enterprise and advisory world, Harry Cendrowski and John Alfonsi of Cendrowski Corporate Advisors, to expose what actually drives trust, loyalty, and long-term relationships with wealthy families.

This is not a fluffy conversation about “relationship building.”

It is a behind-the-scenes look at how elite advisors operate when real money, real families, and real legacy are on the line.

You will hear why high-net-worth relationships fail when professionals approach wealthy clients as “targets” instead of human beings with emotional, generational, and identity-level stakes involved. 

John explains why even a perfectly executed financial plan can collapse if you ignore the emotional side of exits, litigation, or succession. Harry reveals how trust is built not through salesmanship, but through consistency, generosity, and genuine curiosity about a client’s life, not just their balance sheet.

They also break down the invisible mechanics of elite advisory relationships, including why asking better questions beats delivering smarter answers, how to communicate complex ideas without losing credibility, and why wealthy families judge you as a reflection of themselves.

The conversation moves into generational shifts, showing how millennial and next-generation wealth holders think differently about risk, exits, and advice, and why advisors who fail to adjust will quietly be replaced by those who do.

If you work with business owners, wealthy families, or aspirational high-net-worth clients, this episode will challenge many of your assumptions about what “expertise” really means and why most advisors never get invited into the inner circle.

This is a masterclass in how real trust is built at the highest levels of the market.