
Wealth of Wisdom
Welcome to the Wealth of Wisdom podcast with your hosts Tom McCullough and Keith Whitaker. This podcast is an audio companion to the book, ‘Wealth of Wisdom: The Top 50 Questions Wealthy Families Ask’ written by Tom and his co-author Keith Whitaker. The book features insights from more than 50 of the world’s top thinkers and practitioners in the family wealth field and each podcast episode features an interview with a different contributor to the book.
Latest episodes

Jan 27, 2025 • 51min
Assessing Your Family's Financial and Family Management Needs
In this episode of the Wealth of Wisdom podcast series, Keith Whitaker speaks with Scott Hayman and Tom McCullough, co-founders of Northwood Family Office. Scott and Tom share the inspiring story of how Northwood was founded and how the company has evolved over the last two decades. At the heart of this episode is an in-depth discussion of Northwood’s Family Self-Assessment Tool, featured in Wealth of Wisdom. Tom and Scott explain how this 52-question framework helps families identify strengths and gaps in areas such as investments, estate and tax planning, family education, and succession planning. They also share valuable insights on how couples and families can use the tool to foster dialogue, gain clarity, and improve the probability of meeting their long-term goals.

6 snips
Jan 14, 2025 • 57min
Enhancing Family Wealth Conversations
Keith Whitaker, co-author of ‘Wealth of Wisdom’ and head of Wise Counsel Research, shares his expertise on enhancing family wealth conversations. He highlights the five dimensions of 'family capital'—human, legacy, relational, structural, and social—offering tools for effective legacy planning. Key discussions include strategies for sensitive family topics like prenuptial agreements and establishing ground rules for constructive family meetings. Keith emphasizes the significance of emotional aspects alongside finances, advocating for balanced wealth management and stronger family dynamics.

Nov 4, 2024 • 50min
Achieving New Insights and Possibilities through Generative Dialogue
In this episode, Michelle Osry discusses how she used Otto Scharmer's Generative Dialogue framework to help a stuck family improve their communication. The framework includes four conversational fields, from Politeness to Flow, each representing a different level of conversation depth. By applying this framework, families can navigate difficult conversations and achieve a state of flow where new possibilities emerge, fostering lasting success across generations.

Aug 12, 2024 • 42min
Learning From Your Money History and Writing a New Story
Jill Shipley, an expert on how financial history shapes behaviors, explores the deep-rooted influences of our past money experiences. She discusses the need for personal reflection to uncover and rewrite our money narratives, emphasizing open family conversations about values and wealth. Jill addresses the emotional complexities of inherited wealth and encourages a shift in perspective towards philanthropy. By promoting dialogue and understanding, she advocates for healthier financial attitudes and a more generous mindset.

Jul 30, 2024 • 56min
How Powerful Are Your Questions?
Ian McDermott, an advisor to wealthy families and author, joins Tom McCullough to discuss the transformative power of questions. They emphasize how re-framing questions can stimulate positive thinking and enhance communication. The conversation explores strategies for shifting from problem-focused to outcome-oriented discussions, fostering collaboration and emotional validation. Ian shares insights on leveraging community resources and the importance of humility in professional settings, offering valuable guidance for families navigating complex challenges.

Jul 16, 2024 • 40min
Helping Families Move Up the Philanthropic Curve
In this podcast episode, Leslie Pine explores the world of family philanthropy and introduces the TPI Philanthropic Curve, a tool to assess philanthropic journeys. She outlines the six levels of the curve, emphasizing the importance of strategic giving, impact measurement and collaboration, and inspiring families to reflect on their philanthropic aspirations and potential for positive change.

Jun 11, 2024 • 48min
Is Your Infrastructure Resilient?
In this episode, Natasha Pearl highlights the importance of personal and administrative infrastructure for wealthy individuals and their advisors. Using the example of "Mr. Bluebird," she illustrates how a lack of infrastructure can lead to financial and personal challenges. Natasha provides a seven-step plan to help identify and address infrastructure deficiencies, emphasizing the value of resilient infrastructure in wealth preservation and quality of life.

May 31, 2024 • 40min
Developing a Family Wealth Education Plan
In this episode, we delve into Dr. Kirby Rosplock's insights on developing a family wealth education plan, highlighting the journey from financial parenting to engaging adult family members with innovative learning strategies. Discover the transformative approach to preparing generations for wealth stewardship, ensuring the sustainability and growth of family legacies through tailored educational frameworks.

Apr 24, 2024 • 42min
Finding an Advisor Who Will Help Your Family Thrive for Generations
Kathy Lintz and Ned Rollhaus discuss the importance of choosing the right advisor for family prosperity. Topics include aligning advisor services with family goals, navigating complex financial decisions, understanding family dynamics, choosing advisors based on needs and fee structures, guidelines for selecting wealth advisors, prioritizing family discussions, and ensuring advisor alignment with family requirements.

Apr 3, 2024 • 43min
Democratizing Family Decision-Making
In this engaging podcast episode, co-host Keith Whitaker and Barbara Hauser explore the concept of democratizing family decision-making to avoid conflicts and foster fairness within families. Drawing on her extensive experience, they discuss the importance of transparency, accountability, and participation as key principles for successful family governance, sharing real-life examples of how these principles transformed family dynamics and decision-making processes.
Remember Everything You Learn from Podcasts
Save insights instantly, chat with episodes, and build lasting knowledge - all powered by AI.