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The Cycle of the Gift: Family Wealth and Wisdom


Praise for The Cycle of the Gift

"A generous spirit and crystal-clear values are the foundation that protect a family from spiraling into dysfunction and entitlement. The Cycle of the Gift is the perfect blueprint."
—Charlotte B. Beyer, founder and former CEO, Institute for Private Investors

"This is a remarkable book. It truly helps illuminate the issues and breakthrough conversations that families can have around giving to their children and grandchildren."
—Charles W. Collier, former Senior Philanthropic Advisor, Harvard University

"The authors have given the reader much to consider–the spirit of giving, the desired effect when making gifts, and the function of the gift over the form. Like Family Wealth, this book puts a spotlight on the most important questions for family members to contemplate when making gifts and offers the potential for completely different outcomes from the experience."
—Sara Hamilton, founder and CEO, Family Office Exchange

"With thoughtfulness and clarity based on a multi-discipline collaboration of considerable expertise, the authors challenge readers to mindfully consider the dynamics that occur between a gift giver and the recipient. The Cycle of the Gift is an invaluable resource for both individuals and the advisory community."
—Dr. Lee Hausner, Managing Director, First Foundation Advisors

"The Cycle of the Gift is a must-read for affluent families. It deals with one of the most difficult and profound issues: how much should I gift and what process should I follow? It provides powerful insights to help family members become mindful givers and receivers."
—Mel Lagomasino, CEO, GenSpring Family Offices

"This extraordinary book is a gift. Its contribution is helping us understand the complete cycle of any gift. The true gift of this book and of its writers is turning awkward situations and even pain . . . into joy!"
—Thomas R. Livergood, CEO, The Family Wealth Alliance

"The best learning comes when a book is able to take something that you do and consider important, and guides you to step back and look with fresh eyes.The Cycle of the Gift takes the process of gifting, a foundation of all society, and takes us on a journey to understand its deeper nature."
—Dennis Jaffe, Saybrook University

"These well-versed authors offer a golden blend of technically astute practical guidance and the foundational spiritual and classical knowledge of wisdom, discernment, and counsel."
—Paul G. Schervish, Professor and Director, Center on Wealth & Philanthropy, Boston College

"Families with wealth face a great and persistent challenge: how to give to children and grandchildren in ways that enhance their lives rather than create dependency. The Cycle of the Gift faces this challenge squarely with sound and prudent counsel. If leaving a legacy is important to you, this is a must-read."
—James P. Steiner, President, Abbot Downing, a Wells Fargo Business

James E. Hughes Jr., Esq., is a resident of Aspen, Colorado, and a retired attorney. Jay is the author of Family Wealth: Keeping It in the Family, and of Family–The Compact Among Generations, and numerous articles on family governance and wealth preservation as well as a series of "Reflections" which can be found on the Articles section of his website He was the founder of a law partnership in New York City and has spoken frequently at numerous international and domestic symposia. He is a member of various philanthropic boards and a member of the editorial boards of various professional journals.

Dr. Susan E. Massenzio is a psychologist and founding Associate of Wise Counsel Research Associates, a think-tank and consultancy. Susan has extensive experience consulting to senior executives, leadership teams of Fortune 500 companies, and heads of family businesses. Susan served for many years as the senior psychologist for John Hancock Financial Services, a senior vice president at Wells Fargo Family Wealth, and professor and program director at Northeastern University. Susan is a member of the Collaboration for Family Flourishing.

Dr. Keith Whitaker is an educator and founding Associate with Wise Counsel Research Associates, a think-tank and consultancy. Keith has many years' experience consulting with advisors to and leaders of enterprising families. Keith served as a managing director at Wells Fargo Family Wealth, where he founded the innovative Family Dynamics Practice. He has also served as a researcher at the Center on Wealth and Philanthropy, a private trustee, a director of a private foundation, and a philosophy professor at Boston College.

Preface xv

Acknowledgments xix

Introduction xxv

Chapter 1 The Elephant in the Room 1

Grandparents’ Checks 2

When Giving Becomes an Opportunity 4

Chapter 2 The Spirit of the Gift 7

Where the Spirit Leads 11

The Who of Giving

Chapter 3 Becoming a Wise Giver 17

Know Thyself 18

How Much? 21

Guilt and Remorse 24

Nothing Too Much 26

Chapter 4 Receiving Wisely 29

A Bad Investment? 30

The Psychological Stages of Giving 32

Giving and the Work Ethic 36

Not Yet 39

Meteors and Resilience 41

Investing in Recipients 44

Chapter 5 Spouses 47

Learning from Yourselves and Each Other 47

Three-Step Process 48

Blended Families 50

Prenuptial Discussions 51

Fiscal Unequals 54

Chapter 6 Grandparents 57

Grandparents’ Great Opportunity 57

Involving Parents 58

Grandparents and Philanthropy 61

Chapter 7 Trustees 67

The Choice of Trustee 67

The Type of Trustee 69

The Relationship between Beneficiary and Trustee 69

A Regenerative Role 74

Chapter 8 Elders 77

Intergenerational Dynamics 78

Growing Elders 79

The Work of Elders 81

The How of Giving

Chapter 9 Control versus Freedom 87

The Myth of the Free Gift 87

Cui Bono? 88

The Giving of Accounts 90

Letting Be 92

Chapter 10 Fair versus Equal, Separate versus Together 97

The Balancing Act 98

Pot Shots 100

Flourishing 102

Promises 103

Chapter 11 Giving Outright, via Loans, or in Trust? 107

Options 108

Sharing the Spirit 108

Making Loans Work 109

Why Trusts? 110

The Family Bank 113

Form versus Function 115

The What and Why of Giving

Chapter 12 What Families Give 121

Homes 121

Business Interests 125

Values 131

Rituals 134

Reputation 136

Chapter 13 The Why of Giving 141

Why Not 142

The Family Tree 144

Giving Thanks 146

About the Authors 151

Index 155