Today’s episode is different. My guest isn’t an exited founder but she’s someone we all need.
Amy Castoro helps families have honest conversations about wealth—the kind most of us were never taught to have.
She shares practical tools from her firm’s 50 years of experience advising some of the wealthiest families in America.
Her work focuses on the emotional side of money—how we build trust, protect our closest relationships, speak openly, and prepare the next generation to handle wealth well.
We talk about raising children with money and how to rethink our own relationship with it after a successful exit.
It’s one of the most useful conversations I’ve had. Amy’s views challenged my own.I hope it helps you as much as it helped me.
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00:01:59 Amy’s Background & Work with the Williams Group
00:03:30 Why 70% of Families Fail at Wealth Transition
00:05:18 Trust, Communication & Heir Preparedness
00:08:18 How Early Should Kids Be Taught About Wealth?
00:10:31 Age-Appropriate Conversations About Philanthropy
00:13:17 Creating Motivation Without Financial Desperation
00:16:23 Responding to Kids Asking About Inheritance
00:20:35 Involving Children in Wealth Management Early
00:22:33 Teaching Kids to Say “No” & Handle Peer Pressure
00:26:44 Skills Young Heirs Often Feel They Miss
00:29:09 Should Children Be Encouraged to Be Entrepreneurs?
00:32:28 What If the Family Came into Wealth Late?
00:36:04 First Family Meeting: What to Discuss
00:37:28 Re-engaging the “Unmotivated” Youngest Child
00:40:29 Coaching vs. Therapy in Wealth Transition
00:41:41 Families with Young Kids: How to Start Early
00:44:33 Relationship Skills & Communication Patterns
00:47:06 Why the Skills That Build Wealth Won’t Transition It
00:48:20 Balancing Entrepreneurship & Parenting Post-Exit
00:50:39 Modeling Purposeful Wealth, Not Just Growth
00:54:36 What Successful Families Say the Purpose of Wealth Is
00:56:49 Defining Family Values Around “Education”
00:58:41 Reconciling Different Values in the Family
00:59:50 Allowance Strategies in Wealthy Families
01:01:38 Knowing When to Shift from Parent to Mentor
01:03:28 Creating & Living a Family Mission Statement
01:06:06 New Program: Next Gen Leaders
01:07:25 Common Mistakes Families Make Around Wealth
01:10:34 Should Families Hold Regular Meetings?
01:12:37 The #1 Shift Families Must Make for Success
01:13:38 Amy’s Recommended Books on Family Wealth
01:15:15 Final Thoughts: Preparing the Family for the Assets
