A Wealth Advisor's Philanthropy Wake-Up Call

In this conversation, Tony talks about what it actually takes to move philanthropy from obligation to intention — why the standard "know your client" framework falls short, what advisors are still afraid to ask, and how the most meaningful giving rarely begins with a check. He also shares the personal experience that reoriented his entire relationship with generosity, and what he believes is at stake as the wealth management profession faces a generational reckoning. This is a candid, behind-the-bar conversation about perspective, legacy, and what it means to serve a client well across every stage of their wealth journey. Tony Guinane spent more than two decades managing wealth for some of the most successful families in the country before co-founding Dial Square Private Wealth with approximately $1.2 billion in client assets.