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Wealth of Wisdom

The Top 50 Questions Wealthy Families Ask


About the Authors


Tom McCullough is Chairman and CEO of Northwood Family Office

Tom has spent over 35 years in the wealth management/family office field, initially in senior executive roles with RBC Wealth Management. Tom co-founded Northwood Family Office in 2003 and it has become one of the leaders in its field. Northwood has consistently been recognized as the ‘#1 independent family office in Canada’ by Euromoney in its global private banking survey.

Tom is a frequent speaker on issues relevant to families of wealth and is the co-author of Family Wealth Management: 7 Imperatives for Successful Investing in the New World Order. He is an Adjunct Professor and Executive-in-Residence at the University of Toronto’s Rotman School of Management, and is a faculty member in Rotman’s Family Wealth Management program for families of wealth. He is also a Fellow of the Family Firm Institute (FFI) and holds an Advanced Certificate in Family Business Advising from FFI.

Tom holds an MBA from the Schulich School of Business at York University, as well as the CIM (Chartered Investment Manager) and CIWM (Certified International Wealth Manager) designations, and is a registered Portfolio Manager. He is actively involved in a wide range of philanthropic and community activities, in Canada and the developing world. Tom is also the board chair of The Bentway Conservancy, a new 1.75 km urban public park and performance space underneath Toronto’s Gardiner Expressway.


Keith is President of Wise Counsel Research

Keith has consulted for many years with leaders of enterprising families, helping them plan succession, develop next generation talent, and communicate around estate planning. With a background in education and philanthropy, he enables family leaders to better understand their values and goals as well as to have a positive impact on the world around them. Family Wealth Report named Keith the 2015 “outstanding contributor to wealth management thought-leadership.”

Keith holds a Ph.D. in Social Thought from the University of Chicago and a BA and MA in Classics and Philosophy from Boston University. He serves on the board of directors of the National Association of Scholars.



Dirk Jungé
Chairman, Pitcairn Company

SECTION 1 – Thinking Through What Matters Most

Chapter 1 – Are You Wealthy?

Patricia Angus
CEO and Founder, Angus Advisory Group LLC

Chapter 2 – What Are the Most Important Factors in Living Well?

Scotty McLennan
Lecturer in Political Economy, Stanford Graduate School of Business

Chapter 3 – What Are the Key Considerations in Crafting Your Legacy?

Thayer Willis
Wealth Counselor

Chapter 4 – What Does Passing on Values to the Next Generation Really Look Like?

Ellen Perry
Founder and Managing Partner, Wealthbridge Partners

Chapter 5 – How to Think Through Using Resources That Exceed My Personal Needs?

Paul Schervish
Professor Emeritus of Sociology, Boston College

Chapter 6 – Does Family History Matter?

Heidi Druckemiller
Senior Consultant, The Winthrop Group

SECTION 2 – Planning Thoughtfully

Chapter 7 – Is It Worth Having a Financial Plan?

Scott Hayman
President, Northwood Family Office Ltd.

Chapter 8 – What Is the Right Balance Between Saving and Spending in Retirement?

Meir Statman
Professor of Finance, Santa Clara University

Chapter 9 – How Do You Start a Family Conversation About Prenuptial Arrangements?

Charles Collier
Senior Philanthropic Advisor, retired, Harvard University

Chapter 10 – How Can You Preserve a Beloved Family Vacation Home or Estate?

Jamie Forbes
Founder, Forbes Legacy Advisors

Chapter 11 – How Can You Prepare for Longevity and Mental Incapacity Among Family Members?

Patricia Annino
Partner, Rimon PC

Chapter 12 – How Do You Prepare for a Good Goodbye?

Kathy Wiseman
Co-Founder, Navigating Systems

SECTION 3 – Investing Wisely

Chapter 13 – How Can You Make Sure Your Portfolio Lines Up with Your Actual Goals?

Ashvin Chhabra
President, Euclidean Capital

Chapter 14 – What Return Should You Expect from Your Investments?

Christopher Brightman
Chief Investment Officer, Research Affiliates

Chapter 15 – What Should Your Asset Allocation Be?

Jean Brunel
Managing Principal, Brunel Associates

Chapter 16 – Does Investing Have to Be Complicated?

Robert Maynard
Chief Investment Officer, Public Employee Retirement System of Idaho

Chapter 17 – How Should You Understand and Deal with Investment Risk?

Howard Marks
Co-Chairman and Co-Founder, Oaktree Capital

Chapter 18 – What Is the Most Useful Definition of Risk for Family Investors?

James Garland
Former President, The Jeffrey Company

Chapter 19 – Is Active Management Still Worthwhile? – I

Charles Ellis
Investment Consultant

Chapter 20 – Is Active Management Still Worthwhile? – II

Randolph Cohen
Senior Lecturer, Entrepreneurial Management, Harvard Business School

SECTION 4 – Raising the Rising Generation

Chapter 21 – How Do You Raise Responsible, Independent, and Productive Children (versus Entitled Trust Fund Babies)?

Jill Shipley
Partner, Cresset Family Office

Chapter 22 – How Can You Help Children Thrive in a World Focused on Success?

Suniya Luthar
Professor of Psychology, Arizona State University

Nina Kumar
Product Manager, IBM Watson Health

Chapter 23 – How Much Money Should You Leave Your Children, and When?

Peter Evans
Principal, AFGO Associates

Chapter 24 – How Do You Start a Family Conversation About Financial Inheritance?

Charles Collier
Senior Philanthropic Advisor, retired, Harvard University

Chapter 25 – How Can You Avoid the Negative Impacts of Giving Money to Family Members?

Lee Hausner
Clinical Psychologist, Business Consultant

Chapter 26 – How Can Your Family Encourage Financial Literacy in Every Member?

Coventry Edwards-Pitt
Partner and Chief Wealth Advisory Officer, Ballentine Partners

Chapter 27 – How Can Families Support Both Individuality and a Shared Dream?

Kelin Gersick
Co-Founder, Lansberg, Gersick & Associates

SECTION 5 – Making Shared Decisions

Chapter 28 – What Are the Best Ways for a Family to Make Decisions Together?

Barbara Hauser
Barbara R. Hauser LLC

Chapter 29 – How Can You Improve Family Communication?

Jennifer East
Founder, Onida Family Advisors Inc.

Chapter 30 – What Are Practical Tools for Building Healthy Families?

Christian Stewart
Founder, Family Legacy Asia

Chapter 31 – What Is the Point of Family Enterprise Governance?

Katherine Grady
Partner, Lansberg, Gersick & Associates

Ivan Lansberg
Co-Founder, Lansberg, Gersick & Associates

Chapter 32 – Should You Have a Family Meeting?

Mary Duke
Family Advisor, Wise Counsel Research

Chapter 33 – How Can You Best Manage Conflict in Your Family?

Blair Trippe
Managing Partner, Continuity Family Business Consulting

Chapter 34 – Should You Stay Together as a Family or Go Your Separate Ways?

Doug Baumoel
Founding Partner, Continuity Family Business Consulting

SECTION 6 – Combining Family and Business

Chapter 35 – How Can You Engage Your Children in the Management of Your Family Wealth or Business?

Dennis Jaffe
Family Consultant

Chapter 36 – How Can Your Family Develop Leaders Ready to Face the Many Challenges of Business and Family?

Greg McCann
Founder, Principal, McCann & Associates

Chapter 37 – How Can You Ensure the Success of Your Successors?

Dean Fowler
President, Dean Fowler Associates

Chapter 38 – Why Is Family Unity So Important and How Can You Achieve It?

Andrew Hier
Senior Advisor and Partner, Cambridge Family Enterprise Group

John Davis
Founder and Chairman, Cambridge Family Enterprise Group

Chapter 39 – What Are the Signs You’re Losing Control of Your Family Business?

Josh Baron
Co-Founder and Partner, Banyan Global Family Business Advisors

Rob Lachenauer
Co-Founder, Partner and CEO, Banyan Global Family Business Advisors

Chapter 40 – Can a Family Stay Together After the Operating Business Is Sold?

Alex Scott
Chairman, Applerigg Limited

SECTION 7 – Giving Well

Chapter 41 – What Is the Difference Between Charity, Philanthropy, Strategic Philanthropy, and Impact Investing?

Ellen Remmer
Senior Partner, The Philanthropic Institute

Chapter 42 – How Can You Encourage Generosity in Your Family?

Alasdair Halliday
Philanthropic Advisor, Harvard University

Anne McClintock
Executive Director, Harvard University Planned Giving

Chapter 43 – How Do You Engage Children and Grandchildren in Philanthropy?

Lisa Parker
President, Lawrence Welk Family Foundation

Chapter 44 – How Can You Wisely Develop a Long-Term Strategy for Your Philanthropy?

Barnaby Marsh
Co-Founder, Saint Partners

SECTION 8 – Seeking Sound Advice

Chapter 45 – What Types of Advisors Should You Consider?

Susan Massenzio
President, Wise Counsel Research Associates

Chapter 46 – How Can You Find Trustworthy Advisors?

Philip Marcovici
Consultant, Retired Lawyer

Chapter 47 – How Can You Avoid the Next Bernie Madoff?

Stephen Horan
Managing Director, Credentialing, CFA Institute

Robert Dannhauser
Head, Private Wealth Management, CFA Institute

Chapter 48 – Should You Choose a Single-Family Office or a Multi-Family Office?

Kirby Rosplock
Founder, Tamarind Partners

Chapter 49 – How Do You Choose a Good Trustee?

Hartley Goldstone
Consultant, Executive Coach, Wise Counsel Research

SECTION 9 – Facing the Future

Chapter 50 – What Does the Future Hold for Families with Significant Wealth?

James Hughes
Wise Counsel Research

Chapter 51 – How Can You Chart Your Own Path, No Matter What Everyone Else Says You Should Do?

Fernando Del Pino
CEO/CIO, Myway Investments

Chapter 52 – How Do You Balance Family Stability with Resilience Over the Generations?

James Grubman

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