Bill Woodson, Co-Head & Managing Director of Cynosure Wealth Advisors

Todd Rich sits down with Bill Woodson, Co-Head & Managing Director of Cynosure Wealth Advisors for a thoughtful conversation on the purpose behind wealth, the evolution of family offices, and the personal experiences that shaped Bill’s worldview. Bill reflects on a childhood shaped by constant relocation, the discipline he built working through college, and an early career that moved unexpectedly from investment management to public accounting and eventually into the family office ecosystem. Throughout the discussion, he offers insight into the complexities wealthy families face, why coordination and governance can be as important as investment considerations for many families, and how trust and communication form the core of constructive advisory relationships. He also shares the motivation behind his book on family offices and the educational initiatives he is helping build to professionalize the field.

They discuss:
• How early life experiences and working through college shaped Bill’s discipline and confidence
• Lessons from public accounting that informed his transition into family office leadership
• The core challenges wealthy families face and why coordination across advisors is often missing
• The interpersonal and governance dynamics that define successful family office environments
• Bill’s purpose-driven work developing educational programs and contributing to broader societal impact through family offices

Topics:
00:00 – Introduction
03:00 – Early Life, UC Irvine, and Entering the Investment World
09:15 – Lessons from Public Accounting and Working with Founders
12:30 – Silicon Valley and Building a Multifamily Office
15:00 – Entering Private Banking at Merrill Lynch
18:45 – Trust, Delegation, and Personality Dynamics
20:30 – The Societal Good of Family Offices
23:00 – Writing The Family Office
27:30 – Best Practices and Governance Across Generations
29:30 – The EQ Requirements of Family Office Leaders
33:00 – Choosing Between MFOs, SFOs, and RIAs
34:20 – Behavioral Patterns Among New Wealth vs. Multigenerational Wealth
36:00 – Joining Cynosure Wealth Advisors
41:30 – Investment Philosophy and Alternatives
45:00 – The Great Wealth Transfer & Philanthropy Trends
47:30 – Building Academic Programs at Stanford and Chicago Booth
49:30 – The Origin and Impact of First Graduate
52:30 – Closing Questions