Wealthyist E81 |What Do I Want This Money to Do? From Accumulation to Intention with Deanna Tillisch

In this episode of Wealthyist (from Annex Wealth Management), host Deanne Phillips sits down with Deanna Tillisch, a longtime philanthropy and community leader who previously ran the Northwestern Mutual Foundation and led the United Performing Arts Fund for nearly a decade. The conversation explores the pivotal shift many wealthy individuals and families eventually face: moving beyond “How do I build and protect wealth?” to the more intentional question, “What do I want this money to do?” Tillisch distinguishes between simply leaving money (often by defaulting to familiar organizations) and leaving a true intention or legacy. The latter requires strategic, multi-generational planning, due diligence, family conversations, and collaboration with advisors and attorneys. She notes that effective philanthropists typically start with a clear “why”—whether rooted in personal experience (such as her own daughter Casey’s disability and the creation of Casey’s Fund, which supports arts accessibility and has raised far more than expected by telling a genuine story) or by identifying a systemic need (such as education gaps). Sophisticated donors go beyond writing checks: they volunteer, join boards, involve family, meet beneficiaries, and build relationships so they can see impact during their lifetimes. The discussion addresses psychological barriers common in wealth (including “bag lady syndrome” and fear of getting it wrong or losing control), the value of giving while alive rather than only through an estate, focusing deeply on a few organizations instead of spreading gifts widely, the balance of donor guidelines versus micromanagement, and the choice between perpetual endowments and spending down for urgent needs. Tillisch also covers passing values (not just causes) to the next generation through role-modeling and involvement, and how visible recognition can serve as a useful endorsement that inspires others. In a rapid-fire segment, she advocates giving while alive, focusing on fewer organizations deeply, public giving, a mix of permanent and spend-down approaches, and teaching children responsibility by example. The episode closes on the idea that a meaningful legacy is one whose impact you can witness and help sustain while you’re still here—turning accumulated assets into values, stories, and lasting change.